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. 2014 Oct 30;19(11):17478–17535. doi: 10.3390/molecules191117478

A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp.

Qing Xia 1,, Huazheng Zhang 2,, Xuefei Sun 1, Haijuan Zhao 1, Lingfang Wu 1, Dan Zhu 1, Guanghui Yang 1, Yanyan Shao 1, Xiaoxue Zhang 1, Xin Mao 1, Lanzhen Zhang 1,*, Gaimei She 1,*
Editor: Derek J McPhee
PMCID: PMC6271249  PMID: 25361420

Abstract

Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, a traditional Chinese medicine, popularly used for complementary cancer therapy. GTs are lanostane-tetracyclic triterpenes. They have been reported to possess anti-tumor, anti-inflammation, antioxidant, antimicrobial and blood fat reducing effects. To date, 316 GTs have been found and their similar chemical structures have proved difficult to elucidate. This paper compiles 316 naturally occurring triterpenes from Ganoderma based on the literature published through January 2013 along with their structures, physiological activities and 13C-NMR spectral data.

Keywords: Ganoderma, triterpenes, chemical structure, 13C-NMR data, bioactivity

1. Introduction

Ganoderma lucidum (Leyss. ex Fr.) Karst, a medicinal fungus called “Lingzhi” in China, is one of the most highly regarded medicinal fungi in the world. It is ranked as rare and precious in the ancient Chinese medical encyclopedias “Shen Nong’s Ben Cao Jing” and “Ben Cao Gang Mu”. The main Lingzhi-producing regions are East China, Southwest China and the provinces of Hebei, and Guangxi. It can be used in the prevention and treatment of various types of disease, such as cancer, hepatopathy, arthritis, hypertension, neurasthenia, debility, etc. Its the most attractive characteristics are its immunomodulatory and antitumor activities [1,2,3,4,5,6,7,8]. Ganoderma contains many bioactive natural components, including triterpenes (GTs), polysaccharides, proteins, and unsaturated fatty acids. The triterpenes and polysaccharides are deemed to be the primary bioactive compounds of Ganoderma.

Kubota isolated ganoderic acid A and ganoderic acid B from Ganoderma lucidum (FR.) KARST in 1982 [9]. Since then, more than 316 triterpenes have been isolated from the fruiting bodies, spores, gills, and mycelia of many Ganoderma mushrooms. This total was derived from our investigation of the references. As reported, the majority of GTs exhibit a wide range of biological activities, including antitumor, anti-HIV-1, antihypertensive, antiangiogenic, immunomodulatory, antiandrogenic, antihepatitis B, antioxidant, anticomplement, and antimicrobial activities [10,11,12,13]. All GTs are tetracyclic triterpenes. Their chemical structures are more complex than those of other lanostanes, owing to their highly oxidized state. Generally, GTs contain 30 or 27 carbon atoms, and some have 24. The numbers of substituents as well as the positions increase the structural complexity. In this paper, all 316 triterpenes are listed. In accordance with the number of carbon atoms and their molecular features, they can be divided into different structural groups. The 13C-NMR data of those triterpenes, elucidation of the compounds’ structures and their bioactivities are discussed. We aim at providing a useful and fast way for identifying GTs. Finally, possible trends and perspectives for future investigation of these mushrooms are also included.

2. Ganoderma Triterpenes

Triterpenes are widely distributed in traditional Chinese medicines. Their structures are considered to be derived from the acyclic precursor squalene. More than 20,000 triterpenes have been isolated and identified from Nature, including squalene, lanostane, dammarane, lupine, oleanane, ursane, and hopane structure types [14,15]. The Ganoderma triterpenes belong to the lanostane triterpenes (Figure 1).

Figure 1.

Figure 1

A prototypical lanostane triterpenoid skeleton.

Most of them contain 30 or 27 carbon atoms. A few have 24 carbon atoms. These compounds possesses the same skeleton, namely a trans configuration of rings A/B, B/C, C/D and and 10β, 13β, 14α, 17β substituents. Moreover, substituents are always found at the C-3, 7, 11, 12, 15, 22, 23, 24 and 25 positions of the parent nucleus.

On the basis of the substituent groups and double bonds in the same position, they are classified into different types. Compounds 1221 (Figure 2, Figure 3, Figure 4, Figure 5, Figure 6, Figure 7, Figure 8, Figure 9, Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16, Figure 17, Figure 18, Figure 19, Figure 20 and Figure 21) possess 30 carbon atoms. Among them, 137 (Figure 2) contain double bonds between C-8 and C-9, a keto group at C-23, and substituent groups at C-3, 7, 11, 12, 15, 25. In this figure, compounds 1, 3, 4, 7, 8, 1114, 17, 18, 20, 25, 26, 28, 31, 32, 34, and 35 possess β-hydroxy groups at C-3, and the others possess a keto group, except 3β-oxo-formyl-7β, 12β-dihydroxy-5α-lanost-11,15,23-trioxo-8-en(E)-26-oic acid (21) with a formyl located at the C-3 position. Compounds 2, 3, 917, 1923, 25, 27, 31, 3436 have hydroxy groups at C-7, and furthermore, 19, 20, 22 have α-configurations. What’s more, compounds 1, 4, 18, 24, 26, 2830, 32, 33, and 37 have a carbonyl at C-7. In this group, C-11 mainly has a carbonyl substituent except in ganoderic acid Df (27) with a β-hydroxyl at this position. The majority of these compounds do not have any substituents at C-12, while compounds 1, 4, 24, 25, 28, 29, 31 possess β-acetyloxy and compounds 21, 3537 possess β-hydroxyls. All of these compounds display carbonyls or β-hydroxyls at C-15. As to other configurations, both α- and β-C-21, 17β (compounds 516, 21, 2830, 35) and 20 α-configurations can be found in this group. Carboxyl, formyl, ethanoyl or butyryl moieties can be found at C-25, most commonly carboxyl. These compounds have extensive biological activities.

Figure 2.

Structures of compounds 137.

Figure 2

Cpd R1 R2 R3 R4 R5 R6 R7
1 β-OH =O =O β-O-Ac =O α-CH3 COOBu
2 =O β-OH =O H α-OH α-CH3 COOBu
3 β-OH β-OH =O H =O α-CH3 COOBu
4 β-OH =O =O β-O-Ac α-OH α-CH3 COOH
5 =O H =O H α-OH β-CH3 COOH
6 =O H =O H α-OH β-CH3 COOCH3
7 β-OH H =O H α-OH β-CH3 COOH
8 β-OH H =O H α-OH β-CH3 COOCH3
9 =O β-OH =O H α-OH β-CH3 COOH
10 =O β-OH =O H α-OH β-CH3 COOCH3
11 β-OH β-OH =O H =O β-CH3 COOH
12 β-OH β-OH =O H =O β-CH3 COOCH3
13 β-OH β-OH =O H α-OH β-CH3 COOH
14 β-OH β-OH =O H α-OH β-CH3 COOCH3
15 =O β-OH =O H =O β-CH3 COOH
16 =O β-OH =O H =O β-CH3 COOCH3
17 β-OH β-OH =O H α-OH α-CH3 COOCH3
18 β-OH =O =O H α-OH α-CH3 COOCH3
19 =O α-OH =O H α-OH α-CH3 COOCH3
20 β-OH α-OH =O H α-OH α-CH3 COOCH3
21 O-CHO β-OH =O β-OH =O β-CH3 COOH
22 =O α-OH =O H α-OH α-CH3 COOH
23 =O β-OH =O H =O α-CH3 COOH
24 =O =O =O β-O-COCH3 =O α-CH3 COOEt
25 β-OH β-OH =O β-O-COCH3 =O α-CH3 COOCH3
26 β-OH =O =O =O =O α-CH3 COOH
27 =O β-OH β-OH H =O α-CH3 COOH
28 β-OH =O =O β-O-Ac =O β-CH3 COOH
29 =O =O =O β-O-Ac =O β-CH3 COOH
30 =O =O =O H =O β-CH3 COOH
31 β-OH β-OH =O β-O-Ac =O α-CH3 COOH
32 β-OH =O =O H =O α-CH3 COOH
33 =O =O =O H α-OH α-CH3 COOH
34 β-OH β-OH =O H α-OH α-CH3 COOH
35 β-OH β-OH =O β-OH =O β-CH3 COOH
36 =O β-OH =O β-OH =O α-CH3 COOH
37 =O =O =O β-OH =O α-CH3 COOH

Figure 3.

Structures of compounds 3870.

Figure 3

Cpd R1 R2 R3 R4 R5 R6 R7 R8
38 =O β-OH =O H =O α-CH3 H COOH
39 =O β-OH =O H α-OH α-CH3 H COOH
40 β-OH β-OH =O β-O-Ac =O α-CH3 H COOH
41 β-OH H =O β-O-Ac α-O-Ac α-CH3 H COOH
42 =O =O =O H =O α-CH3 β-OH COOH
43 β-OH =O H H H β-CH3 H COOH
44 =O OH =O H =O α-CH3 OH COOH
45 =O =O H H H α-CH3 H CHO
46 β-OH =O H H H α-CH3 H CHO
47 =O β-OH =O H α-OH α-CH3 β-OH COOH
48 =O α-OH =O H α-OH α-CH3 β-OH COOH
49 β-OH β-OH =O H =O α-CH3 β-OH COOH
50 β-OH =O =O H =O α-CH3 β-OH COOH
51 β-OH β-OH =O β-OH =O α-CH3 β-OH COOH
52 β-OH =O =O β-OH =O α-CH3 β-OH COOH
53 β-OH β-OH =O H =O α-CH3 H COOH
54 =O H =O H α-OH β-CH3 H COOH
55 =O α-OH H H H β-CH3 H CHO
56 α-O-Ac α-O-Ac H H α-OH β-CH3 H COOH
57 =O =O =O H H α-CH3 H CHO
58 =O =O H H H α-CH3 H CH2OH
59 α-O-Ac α-O-CH3 H H α-OH β-CH3 H COOH
60 =O =O α-OH H H α-CH3 H COOH
61 =O =O β-OH H H α-CH3 H COOH
62 β-OH =O H H H α-CH3 H CH2OH
63 β-OH =O H H H α-CH3 H CHO
64 =O =O H H H α-CH3 H COOH
65 =O α-OH H H α-O-Ac α-CH3 H COOH
66 β-OH β-OH =O H α-OH α-CH3 β-OH COOH
67 β-OH H =O H α-OH α-CH3 β-OH COOH
68 =O β-OH =O H α-OH α-CH3 H CHO
69 =O H =O H α-OH α-CH3 β-OH COOH
70 α-O-Ac α-OH H H α-O-Ac β-CH3 H COOH

Figure 4.

Structures of compounds 7184.

Figure 4

Cpd R1 R2 R3 R4 R5
71 α-O-Ac α-OH α-O-Ac β-CH3 ξ-O-Ac
72 α-O-Ac α-O-Ac α-OH β-CH3 ξ-O-Ac
73 α-O-Ac α-O-CH3 H β-CH3 ξ-O-Ac
74 α-O-Ac α-O-CH3 α-OH β-CH3 ξ-O-Ac
75 α-O-Ac α-OH α-OH β-CH3 ξ-O-Ac
76 α-OH α-O-CH3 H β-CH3 ξ-O-Ac
77 α-O-Ac α-OH H α-CH3 β-O-Ac
78 β-O-Ac =O H α-CH3 β-O-Ac
79 β-OH =O H α-CH3 β-O-Ac
80 =O α-OH α-O-Ac α-CH3 β-O-Ac
81 =O α-OH H α-CH3 β-O-Ac
82 =O α-O-CH3 H α-CH3 β-O-Ac
83 α-O-Ac α-OH α-O-Ac α-CH3 β-O-Ac
84 α-O-Ac α-O-CH3 α-O-Ac α-CH3 β-O-Ac

Figure 5.

Structures of compounds 8598.

Figure 5

Cpd R1 R2 R3 R4 R5 R6 R7
85 β-OH =O β-O-Ac =O β-CH3 =O COOH
86 =O β-OH H =O β-CH3 ξ-OH ξ-COOH
87 =O β-OH H =O β-CH3 =O ξ-COOCH3
88 =O β-OH H α-OH β-CH3 =O COOH
89 β-OH β-OH H =O β-CH3 =O COOH
90 β-OH β-OH H α-OH β-CH3 =O COOH
91 =O β-OH H =O β-CH3 =O COOH
92 =O β-OH β-O-Ac =O β-CH3 =O COOH
93 =O =O H =O β-CH3 =O COOH
94 =O =O H α-OH β-CH3 =O COOH
95 β-OH =O H =O β-CH3 =O COCH3
96 β-OH =O H α-OH β-CH3 =O COCH3
97 β-OH =O H =O β-CH3 =O COOH
98 β-OH β-OH β-O-Ac =O α-CH3 =O COOH

Figure 6.

Structures of compounds 99105.

Figure 6

Cpd R1 R2 R3 R4
99 β-OH β-OH H α-OH
100 =O =O H =O
101 =O =O β-O-Ac =O
102 β-OH =O β-O-Ac =O
103 β-OH β-OH β-OH =O
104 =O β-OH OH =O
105 β-OH =O OH =O

Figure 7.

Structures of compounds 106110

Figure 7

Cpd R1 R2 R3 R4 R5 R6 R7 R8
106 =O =O H α-OH β-CH3 ξ-OH =O COOH
107 β-OH β-OH H =O α-CH3 β-OH ξ-OH ξ-COOH
108 =O β-OH H =O α-CH3 β-OH ξ-OH ξ-COOH
109 β-OH β-OH β-OH =O β-CH3 β-OH =O COOH
110 β-OH β-OH =O =O α-CH3 ξ-OH =O COOH

Figure 8.

Structures of compounds 111116

Figure 8

Cpd R1 R2 R3 R4 R5
111 =O =O α-CH3 α-OH CH3
112 =O α-O-Et β-CH3 ξ-OH CH2OH
113 =O =O β-CH3 ξ-OH CH2OH
114 =O α-O-CH3 β-CH3 ξ-OH CH2OH
115 β-OH =O β-CH3 ξ-OH CH2OH
116 β-OH =O α-CH3 α-OH CH3

Figure 9.

Structures of compounds 117123.

Figure 9

Cpd R1 R2 R3
117 β-OH α-COOH CH2OH
118 α-O-Ac CH2O-β-D-xylosyl CH3
119 α-O-COCH3 α-COOH CH3
120 =O α-COO-β-D-glucopyranosyl CH3
121 α-O-Ac α-COOH CH3
122 =O α-COOH CH3
123 β-OH α-COOH CH3

Figure 10.

Structures of compounds 124126.

Figure 10

Cpd R1 R2
124 H COOH
125 H COOCH3
126 β-O-Ac COOH

Figure 11.

Structures of compounds 127130.

Figure 11

Cpd R1 R2 R3 R4
127 β-OH β-OH H =O
128 =O =O β-OH α-OH
129 =O β-OH H =O
130 =O β-OH α-OH =O

Figure 12.

Structures of compounds 131133.

Figure 12

Cpd R1 R2 R3 R4
131 β-OH =O H β-CH3
132 =O β-CH3 α-OH β-CH3
133 =O =O H α-CH3

Figure 13.

Structures of compounds 134 and 135.

Figure 13

Cpd R1 R2
134 α-OH β-CH3
135 =O α-CH3

Figure 14.

Structures of compounds 136139.

Figure 14

Cpd R1 R2 R3 R4
136 β-O-Ac β-OH =O COOH
137 β-O-Ac =O α-OH COOH
138 β-O-Ac β-OH =O COOEt
139 =O =O α-OH COOEt

Figure 15.

Structures of compounds 140141.

Figure 15

Cpd R1 R2 R3
140 =O =O β-OH
141 β-OH α-OH =O

Figure 16.

Structures of compounds 142145.

Figure 16

Cpd R1 R2 R3 R4 R5 R6 R7 R8 R9
142 =O =O =O H α-OH β-CH3 =O H COOH
143 =O =O =O H α-OH β-CH3 =O H COOCH3
144 =O =O =O =O =O β-CH3 =O H COOH
145 H H H H H α-CH3 H ξ-CH3 =O

Figure 17.

Structures of compounds 146147.

Figure 17

Cpd R
146 CH2
147 α-CH3

Figure 18.

Structures of compounds 148155.

Figure 18

Table 6.

Ganoderma triterpenes 156196 in Figure 19.

No. Compound Name Source Ref.
156 15-Hydroxy-ganoderic acid S
(15α-hydroxy-3-oxo-5α-lanosta-7,9(11),24(E)-trien-26-oic acid)
G. lucidum (fruit bodies) [35]
157 3α, 16α-Dihydroxylanosta-7,9(11),24-trien-21-oic acid G. applanatum (fruit bodies) [69]
158 3α, 16α, 26-Trihydroxylanosta-7,9(11),24-trien-21-oic acid G. applanatum (fruit bodies) [69]
159 Ganoderic acid S1 G. lucidum (fruit bodies) [73]
160 Ganoderic acid SZ
(3-oxo-lanosta-7,9(11),24(Z)-trien-26-oic acid)
G. lucidum (fruit bodies) [74]
161 5α-Lanosta-7,9(11),24-triene-15α-26-dihydroxy-3-one G. concinna [75]
162 Ganoderic acid Me (3α, 15α-diacetoxy-5α-lanost-7,9(11),24E-trien-26-oic acid) G. lucidum (cultured mycelial mat) [41]
163 Ganoderic acid Mf (3α-acetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid) G. lucidum (cultured mycelial mat) [41]
164 Ganodermenonol (26-hydroxy-5α-lanosta-7,9(11),24-trien-3-one) G. lucidum (dried fruit bodies) [76]
165 Ganodermadiol (5α-lanosta-7,9(11),24-triene-3β, 26-diol) G. lucidum (dried fruit bodies) [76]
166 Ganodermatriol (5α-lanosta-7,9(11),24-triene-3β, 26,27-triol) G. lucidum (fruit bodies) [77]
167 Ganodermic acid S (lanosta-7,9(11),24-trien-3β, 15α-diacetoxy-26-oic acid) G. lucidum [78]
168 Carnosodione (26,27-dihydroxylanosta-7,9(11),24-trien-3,16-dione) G. carnosum (fruit bodies) [79]
169 Canoderol B ((24E)-5α-lanosta-7,9(11),24-trien-3,26-diol) G. lucidum [23]
170 Ganoderic acid Mk (3α, 22-diacetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid) G. lucidum (mycelia mat) [43]
171 Ganoderiol B (15α, 26,27-trihydroxy-5α-lanosta-7,9(11),24-trien-3-one) G. lucidum (fruit bodies) [77]
172 Ganoderic acid T ((22S, 24E)-3α, 15α, 22-triacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid) G. lucidum (cultured mycelia) [80]
173 Ganoderic acid S ((22S, 24E)-22-acetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (cultured mycelia) [23,80]
174 Ganoderic acid R ((22S, 24E)-3α, 22-diacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid) G. lucidum (cultured mycelia) [80]
175 Ganorbiformin G G. orbiforme [46]
176 Lanosta-7,9(11),24-trien-3β, 15α, 22β-triacetoxy-26-oic acid G. lucidum [81]
177 Lanosta-7,9(11),24-trien-15α-acetoxy-3α-hydroxy-23-oxo-26-oic acid G. lucidum [81]
178 Lanosta-7,9(11),24-trien-3α, l5α-diacetoxy-23-oxo-26-oic acid G. lucidum [81]
179 Lanosta-7,9(11),24-trien-3α, 15α-hydroxy-23-oxo-26-oic acid G. lucidum [81]
180 Lanosta-7,9(11),24-trien-3α-acetoxy-15α, 22β-dihydroxy-26-oic acid G. lucidum [81]
181 Ganodermic acid T-N (3β-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (mycelia) [82]
182 Ganodermic acid T-O (3β-acetoxy-15α-hydroxy-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (mycelia) [82]
183 Ganodermic acid T-Q (3β-oxo-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (mycelia) [82]
184 Compound 10 G. orbiforme [46]
185 Ganoderic acid P ((22S, 24E)-15α, 22-diacetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (cultured mycelium) [50]
186 Ganoderic acid Q ((22S, 24E)-3α, 22-diacetoxy-15α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) G. lucidum (cultured mycelium) [50]
187 Ganoderic acid Jc (15α, 23-dihydroxy-3-oxo-5α-lanosta-7,9(11),24-trien-26-oic acid) G. sinense (fruit bodies) [47]
188 Ganodermatetraol (3β, 15α, 26,27-tetrahydroxy-5α-lanosta-7,9(11),24-triene) G. sinense (fruit bodies) [47]
189 5α-Lanosta-7,9(11),24-triene-3β-hydroxy-26-al G. concinna [75]
190 Ganoderiol F (26,27-dihydroxy-5α-lanosta-7,9(11),24-trien-3-one) G. lucidum (fruit bodies) [39]
191 26,27-Dihydroxy-5α-lanosta-7,9(11),24-triene-3,22-dione G. lucidum (basidiocarp) [83]
192 26-Hydroxy-5α-lanosta-7,9(11),24-triene-3,22-dione G. lucidum (basidiocarp) [83]
193 Ganodermic acid P1 (lanosta-7,9(11),24-trien-3α, 22β-diacetoxy-15α-hydroxy-26-oic acid) G. lucidum (mycelia) [84]
194 Ganodermic acid P2 (lanosta-7,9(11),24-trien-15α, 22β-diacetoxy-3β-hydroxy-26-oic acid) G. lucidum (mycelia) [84]
195 Lanosta-7,9(11),24-trien-3β, 15α, 22-triacetoxy-26-oic acid G. amboinense (fruit bodies) [85]
196 16α-Hydroxy-3-oxolanosta-7,9(11),24-trien-21-oic acid G. applanatum (fruit bodies) [69]

Figure 19.

Structures of compounds 156196.

Figure 19

Cpd R1 R2 R3 R4 R5 R6 R7 R8
156 =O α-OH H β-CH3 H H COOH CH3
157 α-OH H α-OH α-COOH H H CH3 CH3
158 α-OH H α-OH α-COOH H H CH2OH CH3
159 =O H H α-CH3 H H COOH CH3
160 =O H H β-CH3 H H COOH CH3
161 =O α-OH H α-CH3 H H CH2OH CH3
162 α-O-Ac α-O-Ac H β-CH3 ξ-H2 H COOH CH3
163 β-O-Ac α-OH H β-CH3 ξ-H2 H COOH CH3
164 =O H H α-CH3 H H CH2OH CH3
165 β-OH H H α-CH3 H H CH2OH CH3
166 β-OH H H α-CH3 H H CH2OH CH2OH
167 β-O-Ac α-O-Ac H β-CH3 H H COOH CH3
168 =O H O β-CH3 H H CH2OH CH2OH
169 β-OH H H β-CH3 H H CH2OH CH3
170 α-O-Ac α-OH H β-CH3 ξ-O-Ac H COOH CH3
171 =O α-OH H α-CH3 H H CH2OH CH2OH
172 α-O-Ac α-O-Ac H α-CH3 β-O-Ac H COOH CH3
173 α-OH H H α-CH3 β-O-Ac H COOH CH3
174 α-O-Ac H H α-CH3 β-O-Ac H COOH CH3
175 =O H H α-CH3 β-O-Ac H COOH CH3
176 β-O-Ac α-O-Ac H β-CH3 β-O-Ac H COOH CH3
177 α-OH α-O-Ac H β-CH3 H =O COOH CH3
178 α-O-Ac α-O-Ac H β-CH3 H =O COOH CH3
179 α-O-Ac α-OH H β-CH3 H =O COOH CH3
180 α-O-Ac α-OH H β-CH3 H H COOH CH3
181 β-OH α-O-Ac H β-CH3 H H COOH CH3
182 β-O-Ac α-OH H β-CH3 H H COOH CH3
183 =O α-O-Ac H β-CH3 H H COOH CH3
184 =O α-O-Ac H α-CH3 β-O-Ac H COOH CH3
185 α-OH α-O-Ac H α-CH3 β-O-Ac H COOH CH3
186 α-O-Ac α-OH H α-CH3 β-O-Ac H COOH CH3
187 =O α-OH H α-CH3 H OH COOH CH3
188 β-OH α-OH H α-CH3 H H CH2OH CH2OH
189 β-OH H H α-CH3 H H CHO CH3
190 =O H H β-CH3 H H CH2OH CH2OH
191 =O H H α-CH3 =O H CH2OH CH2OH
192 =O H H α-CH3 =O H CH2OH CH3
193 α-O-Ac α-OH H β-CH3 O-Ac H COOH CH3
194 β-OH α-O-Ac H β-CH3 O-Ac H COOH CH3
195 β-O-Ac α-O-Ac H α-CH3 β-O-Ac H COOH CH3
196 =O H α-OH α-COOH H H CH3 CH3

Figure 20.

Structures of compounds 197213.

Figure 20

Cpd R1 R2 R3 R4 R5 R6
197 β-OH H α-CH3 24,25 24,25 CHO
198 β-O-Ac H α-CH3 OAc OH CH2-O-Ac
199 =O H β-CH3 24,25 24,25 CHO
200 =O H β-CH3 24,25 24,25 CH2OH
201 β-OH H α-CH3 α-OH OH CH3
202 =O H β-CH3 α-OH H CH2OH
203 β-OH H α-CH3 OH OH CH2OH
204 =O H α-CH3 OH OH CH3
205 β-OH α-O-Ac β-CH3 H H COOH
206 =O α-OH α-CH3 24,25 24,25 COOH
207 α-OH α-OH β-CH3 24,25 24,25 COOH
208 β-OH α-OH β-CH3 24,25 24,25 COOH
209 α-O-Ac α-O-Ac β-CH3 24,25 24,25 COOH
210 =O H α-CH3 OH OH CH2OH
211 =O α-OH α-CH3 24,25 24,25 COOH
212 =O α-OH α-CH3 24,25 24,25 CH2OH
213 β-OH H α-CH3 24,25 24,25 COOH

Figure 21.

Structures of compounds 214219.

Figure 21

Cpd R1 R2 R3
214 α-OH α-OH α-OH
215 β-OH α-OH β-OH
216 α-O-Ac α-O-Ac α-OH
217 β-O-Ac α-O-Ac α-OH
218 α-OH α-OH β-O-Ac
219 β-OH α-OH β-O-Ac

Compared with the compounds in Figure 2, compounds 3870 in Figure 3 possess double bonds between C-24 and C-25, and have a hydroxy or no substituent at C-23, instead of a carbonyl. Some other substituents are also found at C-3, 7, 11, 12, 15, 23, 25. In this group, lucialdehyde C (46) displays strong antitumor activity and ganoderic acid β (53) reveals great anti-HIV-1 protease activity. Compounds 7184 (Figure 4) get an acetate substituent at C-22 and no substituent at C-11. Meanwhile, compounds 8598 (Figure 5) have double bonds at C-20(22) and keto groups at C-11. From all the listed structures, we can clearly identify compounds 99105 in Figure 6 by the carboxymethyl substitution at C-25, carbonyl substituent at C-11, a keto group at C-23, and β-configuration of C-21. Compounds 106110 are assigned to the same group owing to the methyl at C-20, carbonyl substituent at C-11, and carboxyl at C-25. Lucidumol A (111), ganoderiol C-H (112115), and ganoderitriol M (116) differ from the others on account of the hydroxy at C-24 and C-25. As is shown in Figure 9, Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17, compounds 117123, 124126, 127130, 131133, 134135, 136139, 140141, 142145 and 146147 possess extremely similar skeletons. Because of their distinctive skeletons, 148155 are listed independently. There are no double bonds between C-8 and C-9 in compounds 156221, and two double bonds at C-7(8) and C-9(11), respectively. Among the compounds above, ganoderic acid Jc (187), ganoderiol F (190), and 15α,26-dihydroxy-5α-lanosta-7,9,24(E)-trien-3-one (212) showed remarkable antitumor activity. Significant anti-HIV-1 protease activity has been expressed in ganoderic acid S1 (159) and ganodermic acid T-Q (183). Compounds 156196 (Figure 19) have the same skeleton with substituents at C-3, 15, 16, 20, 22, 23, 25 and double bonds at C-24(25). In this group, 3α, 16α-dihydroxylanosta-7,9(11),24-trien-21-oic acid (157), 3α, 16α, 26-trihydroxylanosta-7,9(11), 24-trien-21-oic acid (158) and 16α-hydroxy-3-oxolanosta-7,9(11),24-trien-21-oic acid (196) possess a hydroxyl at C-16 and carboxyl at C-20. Compounds 197213 (Figure 20) have the same position of substituents. They possess an α- or β-configuration at C-21. The majority have double bonds between C-24 and C-25, except some with hydroxyl, acetoxyl or no substituents at C-24 and C-25. Compounds 214219 (Figure 21) have a hydroxy or acetoxyl at C-22, while epoxyganoderiol B (220) and C (221) (Figure 22) possess an epoxy at C-24(25). Compounds 222266 have the basic skeleton of 27 carbon atoms. Furthermore, they are also subdivided into different groups due to the difference of substituents and position of double bonds. The C-8(9) double bonds are the same in compounds 222260 (Figure 23). 4,4,14α-Trimethyl-5α-chol-7,9(11)-dien-3-oxo-24-oic acid (261) and ganoderic acid Jd (262) (Figure 24) get two double bonds at C-7(8) and C-9(11), respectively. Compared with the compounds in Figure 22, compounds 263266 in Figure 25 have hydroxy substituents at C-29. Compounds 267287 are divided into different groups on account of their characteristic skeletons. We list the structures of compounds 288307 successively, in consideration of the number of substituents and the substituents’ complicated positions. Fornicatin B(308), G(309), A(310), H(311) and australic acid (312) are 3,4-seco-trinorlanostane triterpenoids. In addition, compounds 313316 only have 24 carbon atoms. The names, corresponding plant resources and references of the compounds are compiled in Table 1, Table 2, Table 3, Table 4, Table 5, Table 6, Table 7, Table 8, Table 9, Table 10 and Table 11.

Figure 22.

Structure of compounds 220221.

Figure 22

Cpd R1
220 β-OH
221 =O

Figure 23.

Structures of compounds 222260.

Figure 23

Cpd R1 R2 R3 R4 R5 R6 R7 R8
222 β-OH β-OH =O H =O α-CH3 H COOBu
223 =O β-OH =O H =O α-CH3 H COOBu
224 β-OH β-OH =O H =O CH2 20,21 COOH
225 =O β-OH =O H =O β-CH3 ξ-OH COOH
226 =O =O =O β-O-Ac =O β-CH3 H COOCH3
227 =O β-OH =O H =O CH2 20,21 COOH
228 =O β-OH =O H =O CH2 20,21 COOCH3
229 β-OH β-OH =O H =O α-CH3 H COOH
230 =O =O =O β-O-Ac =O β-CH3 H COOH
231 β-OH =O =O β-O-Ac =O β-CH3 H COOCH3
232 =O =O =O H =O β-CH3 H COOCH3
233 =O OH =O H =O α-CH3 H COOEt
234 β-O-CHO β-OH =O OH =O β-CH3 H COOH
235 =O β-OH =O H =O β-CH3 H COOH
236 =O β-OH =O β-OH =O β-CH3 H COOH
237 β-OH β-OH =O β-OH =O β-CH3 H COOH
238 =O =O H H H α-CH3 H COOH
239 β-OH β-OH =O β-O-Ac =O α-CH3 H COOH
240 β-OH β-OH =O β-O-Ac =O α-CH3 H COOCH3
241 =O β-OH =O H α-OH α-CH3 H COOCH3
242 β-OH =O =O H =O α-CH3 H COOH
243 =O =O =O O-Ac =O β-CH3 H COOCH3
244 β-OH =O =O O-Ac =O β-CH3 H COOCH3
245 =O =O =O α-OH =O β-CH3 H COOCH3
246 β-OH =O =O β-OH =O β-CH3 H COOCH3
247 β-OH α-OH =O H α-OH β-CH3 H COOCH3
248 β-OH β-OH =O H =O α-CH3 H COOCH3
249 =O β-OH =O β-OH =O α-CH3 H COOBu
250 =O β-OH =O H =O α-CH3 H COOCH3
251 =O =O =O β-O-Ac =O α-CH3 H COOH
252 =O =O =O β-O-Ac =O β-CH3 ξ-OH COOH
253 =O =O =O H =O β-CH3 ξ-OH COOH
254 β-OH =O =O β-O-Ac =O β-CH3 ξ-OH COOH
255 β-OH β-OH =O H =O β-CH3 ξ-OH COOH
256 β-OH β-OH =O β-O-Ac =O β-CH3 ξ-OH COOH
257 =O =O =O H =O α-CH3 H COOH
258 β-OH β-OH =O H =O α-CH3 H COOCH3
259 β-OH =O =O β-O-Ac =O α-CH3 H COOH
260 =O β-OH =O H =O α-CH3 H COOH

Figure 24.

Structures of compounds 261262.

Figure 24

Cpd R1 R2
261 =O H
262 =O α-OH

Figure 25.

Structures of compounds 263266.

Figure 25

Cpd R1 R2 R3
263 β-OH H β-CH3
264 =O H β-CH3
265 =O β-OH β-CH3
266 β-OH H α-CH3

Table 1.

Ganoderma triterpenes 137 in Figure 2.

No. Compound Name Source Ref.
1 n-Butyl ganoderate H (n-butyl 12β-acetoxy-3β-hydroxy-7,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) G. lucidum (fruit bodies) [16]
2 Butyl ganoderate A G. lucidum (fruit bodies) [17]
3 Butyl ganoderate B G. lucidum (fruit bodies) [17]
4 Ganoderic acid α (12β-acetoxy-3β, 15β-dihydroxy-7,11,23-trioxo-5α-lanosta-8-en-26-oic acid) G. lucidum (fruit bodies) [18]
5 Ganolucidic acid A G. lucidum (gill surface) [19]
6 Methyl ganolucidate A (methyl 15α-hydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) G. lucidum (gill surface) [19,20]
7 Ganolucidic acid B G. lucidum (gill surface) [19]
8 Methyl ganolucidate B G. lucidum (gill surface) [19,20]
9 Ganoderic acid A (7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oic acid) G. lucidum [9,21]
10 Methyl ganoderate A (methyl 7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) G. lucidum [21]
11 Ganoderic acid B (3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oic acid) G. lucidum [21]
12 Methyl ganoderate B (methyl 3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate) G. lucidum [9,21]
13 Ganoderic acid C (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oic acid) G. lucidum [21]
14 Methyl ganoderate C G. lucidum [21]
15 Ganoderic acid D (7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oic acid) G. lucidum [21]
16 Methyl ganoderate D G. lucidum [21]
17 Methyl ganoderate C2 (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) G. lucidum (gills) [22]
18 Methyl ganoderate K G. lucidum (gills) [22,23]
19 Compound B8 G. lucidum (gills) [22]
20 Compound B9 G. lucidum (gills) [22]
21 3β-Oxo-formyl-7β, 12β-dihydroxy-5α-lanost-11,15,23-trioxo-8-en(E)-26-oic acid G. lucidum (fruit bodies) [24]
22 Ganoderic acid B8 G. lucidum (fruit bodies) [25]
23 Ganoderic acid C1 G. lucidum (fruit bodies) [25]
24 12β-Acetoxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acid ethyl ester G. lucidum [26]
25 3β, 7β-Dihydroxy-12β-acetoxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid methyl ester G. lucidum [27]
26 3β-Hydroxy-7,11,12,15,23-pentaoxolanost-8-en-26-oic acid G. lucidum (fruit bodies) [28]
27 Ganoderic acid Df (7β, 11β-dihydroxy-3,15,23-trioxo-5α-lanosta-8-en-26-oic acid) G. lucidum [29]
28 Ganoderic acid H G. lucidum (gill surface) [30]
29 Ganoderic acid F (12β-acetoxy-3,7,11,15-pentaoxo-5α-lanost-8-en-26-oic acid) G. lucidum (dried fruit bodies) [31]
30 Ganoderic acid E (3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oic acid) G. lucidum (dried fruit bodies) [31]
31 Ganoderic acid K G. lucidum (fruit bodies) [32]
32 Ganoderic acid AM1 G. lucidum (fruit bodies) [32]
33 Ganoderic acid J G. lucidum (fruit bodies) [32]
34 Ganoderic acid C2 (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanosta-8-en-26-oic acid) G. lucidum (gills) [22]
35 Ganoderic acid G (3β, 7β, 15β-trihydroxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid) G. lucidum (dried fruit bodies) [31]
36 7β, 12β-Dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8-en-26-oic acid G. lucidum [26]
37 12β-Hydroxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acid G. lucidum [26]

Table 2.

Ganoderma triterpenes (3870) in Figure 3.

No. Compound Name Source Ref.
38 Ganoderic acid GS-1 (7β-hydroxy-3,11,15-trioxolanosta-8,24(E)-dien-26-oic acid) G. sinense (fruit bodies) [33]
39 Ganoderic acid GS-2 (7β, 15α-dihydroxy-3,11-dioxolanosta-8,24(E)-dien-26-oic acid) G. sinense (fruit bodies) [33]
40 Ganoderic acid GS-3 (12β-acetoxy-3β, 7β-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid) G. sinense (fruit bodies) [33]
41 Ganoderic acid AP2 (12β, 15α-diacetoxy-3β-hydroxy-11-oxolanost-8,24(E)-dien-26-oic acid) G. applanatum (fruit bodies) [34]
42 23S-Hydroxy-3,7,11,15-tetraoxolanost-8,24E-diene-26-oic acid G. lucidum (fruit bodies) [32]
43 7-Oxoganoderic acid Z (3β-hydroxy-7-oxo-5α-lanosta-8,24(E)-dien-26-oic acid) G. lucidum (fruit bodies) [35]
44 Ganoderic acid LM2 ((23S) 7β,-dihydroxy-3,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid) G. lucidum (fruit bodies) [36]
45 Lucialdehyde B ((24E)-3,7-dioxo-5α-lanosta-8,24-dien-26-al) G. lucidum (fruit bodies) [25]
46 Lucialdehyde C ((24E)-3β-hydroxy-7-oxo-5α-lanosta-8,24-dien-26-al) G. lucidum (fruit bodies) [25]
47 Ganoderic acid γ ((23S)-7β, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
48 Ganoderic acid δ ((23S)-7α, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
49 Ganoderic acid ε ((23S)-3β, 7β, 23-trihydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
50 Ganoderic acid ζ ((23S)-3β, 23-dihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
51 Ganoderic acid η ((23S)-3β, 7β, 12β, 23-tetrahydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
52 Ganoderic acid θ ((23S)-3β, 12β, 23-trihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid) G. lucidum (spores) [37]
53 Ganoderic acid β (3β, 7β-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid) G. lucidum (spores) [38]
54 Ganolucidic acid E (15α-hydroxy-3,11-dioxo-5α-lanosta-8,24E-dien-26-oic acid) G. lucidum (fruit bodies) [39]
55 Ganoderal B (7α-hydroxy-3-oxo-5α-lanosta-8,24E-dien-26-al) G. lucidum [40]
56 Ganoderic acid Ma (3α, 7α-diacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (fruit bodies) [41]
57 Lucialdehyde D (3,7,11-trioxo-5α-lanosta-8,24-diene-26-al) G. pfeifferi (fruit bodies) [42]
58 Ganoderone A (5α-lanosta-8,24-diene-26-hydroxy-3,7-dione) G. pfeifferi (fruit bodies) [42]
59 ganoderic acid Mi (3α-acetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (mycelial mat) [43]
60 11α-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acid G. lucidum [26]
61 11β-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acid G. lucidum [26]
62 Lucidadiol (5α-lanosta-8,24-dien-3β, 26-dihydroxy-7-one) G. lucidum [44]
63 Lucidal (5α-lanosta-8,24E-dien-3β-hydroxy-7-on-26-al) G. lucidum [44]
64 Ganoderic acid DM (3,7-dioxo-8,24(E)-dien-lanosta-26-oic acid) G. lucidum (cultured fruit bodies) [45]
65 Ganoderic acid V G. orbiforme [46]
66 Ganolucidic acid γa (3β, 7β, 15α, 23-tetrahydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid) G. sinense (fruit bodies) [47]
67 Ganolucidate F (3β, 15α, 23-trihydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid) G. sinense (fruit bodies) [47]
68 Lucialdehyde E (7β, 15α-dihydroxy-3,11-dioxo-5α-lanosta-8,24-dien-26-al) G. lucidum (spores) [48]
69 Ganolucidic acid D G. lucidum (spores) [37]
70 Ganoderic acid W G. lucidum (fruit bodies) [41]

Table 3.

Ganoderma triterpenes 7198 in Figure 4 and Figure 5.

No. Compound Name Source Ref.
71 Ganoderic acid Mb (3α, 15α, 22-triacetoxy-7α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (fruit bodies) [41]
72 Ganoderic acid Mc (3α, 7α, 22-triacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (fruit bodies) [41]
73 Ganoderic acid Md (3α, 22-diacetoxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (fruit bodies) [41]
74 Ganoderic acid Mg (3α, 22-diacetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (mycelial mat) [43]
75 Ganoderic acid Mh (3α, 22-diacetoxy-7α, 15α-dihydroxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (mycelial mat) [43]
76 Ganoderic acid Mj (22-acetoxy-3α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) G. lucidum (mycelial mat) [43]
77 3α, 22β-Diacetoxy-7α-hydroxyl-5α-lanost-8,24E-dien-26-oic acid G. lucidum (mycelial mat) [49]
78 Ganorbiformin B G. orbiforme [46]
79 Ganorbiformin C G. orbiforme [46]
80 Ganorbiformin D G. orbiforme [46]
81 Ganorbiformin E G. orbiforme [46]
82 Ganorbiformin F G. orbiforme [46]
83 Ganoderic acid O ((22S, 24E)-3α, l5α, 22-triacetoxy-7α-hydroxy-5α-lanosta-7,24-dien-26-oic acid) G. lucidum (cultured mycelium) [50]
84 7-O-Methylganoderic acid O ((22S, 24E)-3α, l5α, 22-triacetoxy-7α-methoxy-5α-lanosta-8,24-dien-26-oic acid) G. Lucidum (cultured mycelium) [50]
85 12β-Acetoxy-3β-hydroxy-7,11,15,23-tetraoxo-lanost-8,20E-diene-26-oic acid G. lucidum (fruit bodies) [32]
86 23-Dihydroganoderenic acid D (7β, 23ξ-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic acid) G. applanatum (fruit bodies) [51]
87 Methyl ganoderenate D (7β-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic acid methyl ester) G. applanatum (fruit bodies) [51]
88 Ganoderenic acid A ((20E)-7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8,20-dien-26-oic acid) G. lucidum (dried fruit bodies) [31]
89 Ganoderenic acid B ((20E)-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8,20-dien-26-oic acid) G. lucidum (dried fruit bodies) [31]
90 Ganoderenic acid C ((20E)-3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8,20-dien-26-oic acid) G. lucidum (dried fruit bodies) [31]
91 Ganoderenic acid D ((20E)-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8,20-dien-26-oic acid) G. lucidum (dried fruit bodies) [31]
92 12β-Acetoxy-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20-dien-26-oic acid G. lucidum [26]
93 Ganoderenic acid F (3,7,11,15,23-pentaoxo-5α-lanosta-8,20E-dien-26-oic acid) G. applanatum (fruit bodies) [52]
94 Ganoderenic acid G (15α-hydroxy-3,7,11,23-tetraoxo-5α-lanosta-8,20E-dien-26-oic acid) G. applanatum (fruit bodies) [52]
95 Methy ganoderenate H (methyl 3β-hydroxy-7,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate) G. applanatum (fruit bodies) [52]
96 Methyl ganoderenate I (3β, 15α-dihydroxy-7,11,23-trioxo-5α-lanosta-8,20E-dien-26-oate) G. applanatum (fruit bodies) [52]
97 Ganoderenic acid H G. lucidum (fruit bodies) [32]
98 12β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanosta-8,20-dien-26-oic acid G. lucidum [26]

Table 4.

Ganoderma triterpenes 99123 in Figure 6, Figure 7, Figure 8 and Figure 9.

No. Compound Name Source Ref.
99 Methyl ganoderate D (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) G. lucidum (fruit bodies) [53,54]
100 Methyl ganoderate E (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) G. lucidum (gills) [54,55]
101 Methyl ganoderate F (methyl 12β-acetoxy-3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oate) G. lucidum (gills) [56]
102 Methyl ganoderate H (methyl 3β-hydroxy-12β-acetoxy-7,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) G. lucidum (gills) [30,56]
103 Methyl ganoderate G (methyl 3β, 7β, 12β-trihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate) G. lucidum [20]
104 Compound C5 G. lucidum (gill surface) [30]
105 Compound C6 G. lucidum (gill surface) [30]
106 Ganoderic acid AP3 (15α, 20ξ-dihydroxy-3,7,11,23-tetraoxolanost-8-en-26-oic acid) G. applanatum (fruit bodies) [34]
107 23-Dihydroganoderic acid I (3β, 7β, 20,23ξ-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic acid) G. applanatum (fruit bodies) [51]
108 23-Dihydroganoderic acid N (7β, 20,23ξ-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid) G. applanatum (fruit bodies) [51]
109 20-Hydroxylganoderic acid G G. lucidum (fruit bodies) [57]
110 Ganoderic acid I G. lucidum (gills) [22]
111 Lucidumol A ((24S)-24,25-dihydroxylanost-8-ene-3,7-dione) G. lucidum (spores) [38]
112 Ganoderiol C (7α-ethoxy-24,25,26-trihydroxy-5α-lanost-8-en-3-one) G. lucidum (fruit bodies) [39]
113 Ganoderiol D (24,25,26-trihydroxy-5α-lanost-8-en-3,7-dione) G. lucidum (fruit bodies) [39]
114 Ganoderiol G (24,25,26-trihydroxy-7α-methoxy-5α-lanost-8-en-3-one) G. lucidum (fruit bodies) [39]
115 Ganoderiol H (3β, 24,25,26-tetrahydroxy-5α-lanost-8-en-7-one) G. lucidum (fruit bodies) [39]
116 Ganoderitriol M ((24S)-lanosta-7-oxo-8-en-3β, 24,25-triol) G. lucidum (fruit bodies) [58]
117 Sinensoic acid (3,26-dihydroxy-5-lanosta-8,24E-dien-21-oic acid) G. sinense (fruit bodies) [59]
118 Tsugarioside B (3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-d-xyloside) G. tsugae (fruit bodies) [60]
119 Tsugaric acid A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid) G. tsugae [61]
120 Ganosinoside A (3-oxo-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside) G. sinense (fruit bodies) [47]
121 Tsugarioside A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside) G. tsugae (fruit bodies) [60]
122 3-Oxo-5α-lanosta-8,24-dien-21-oic acid G. resinaceum (fruit bodies) [62]
123 3β-Hydroxy-5α-lanosta-8,24-dien-21-oic acid G. tsugae (fruit bodies) [60]

Table 5.

Ganoderma triterpenes 124147 in Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17 and Ganoderma triterpenes 148155 in Figure 18.

No. Compound Name Source Ref.
124 3β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid G. lucidum (fruit bodies) [63]
125 3β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid methyl ester G. lucidum (fruit bodies) [63]
126 12β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid G. lucidum (fruit bodies) [63]
127 Methyl ganoderate I G. lucidum [20,22]
128 Methyl ganoderate AP (methyl 12β, l5α, 20-trihydroxy-3,7,11,23- tetraoxo-5α-lanost-8-en-26-oate) G. applanatum (fruit bodies) [52]
129 Methyl ganoderate N (Methyl 7β, 20-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) G. lucidum (fruit bodies) [64]
130 Methyl ganoderate M (methyl 7β, 12α-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) G. lucidum (fruit bodies) [64]
131 Ganoderiol E (3β, 26,27-trihydroxy-5α-lanosta-8,24-dien-7-one) G. lucidum (fruit bodies) [39]
132 Ganoderiol I (15α, 26,27-trihydroxy-5α-lanosta-8,24-dien-3-one) G. lucidum (fruit bodies) [39]
133 Ganoderiol J (26,27-dihydroxy-5α-lanosta-8,24-dien-3,7-dione) G. sinense (fruit bodies) [47]
134 Epoxyganoderiol A (24S, 25S-epoxy-7α, 26-dihydroxy-5α-lanost-8-en-3-one) G. lucidum [40]
135 Ganoderone C (5α-lanosta-8-ene-24,25-epoxy-26-hydroxy-3,7-dione) G. pfeifferi (fruit bodies) [42]
136 3-O-Acetylganoderic acid B (3β-acetoxy-7β-hydroxy-11,15,23-trioxolanost-8-en-26-oic acid) G. lucidum (mycelia) [65]
137 3-O-Acetylganoderic acid K (3β-acetyloxy-15α-hydroxy-7,11,23-trioxolanost-8-en-26-oic acid) G. lucidum (mycelia) [65]
138 Ethyl 3-O-acetylganoderate B G. lucidum (mycelia) [65]
139 Ethyl ganoderate J G. lucidum (mycelia) [65]
140 Applanoxidic acid G (15β, 20-dihydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid) G. applanatum [66]
141 Applanoxidic acid H (3β, 12α, 20-trihydroxy-7α, 8α-epoxydioxo-5α-lanosta-9(11),16-dien-26-oic acid) G. applanatum [66]
142 8β, 9α-Dihydroganoderic acid J G. lucidum (fruit bodies) [57]
143 Methyl 8β, 9α-dihydroganoderate J G. lucidum (fruit bodies) [57]
144 Ganosporeric acid A (3,7,11,12,15,23-hexaoxo-5α-lanosta-8-en-26-oic acid) G. lucidum (spores) [67]
145 24ξ-Methyl-5α-lanosta-25-one G. applanatum (fruit bodies) [68]
146 3α-Carboxyacetoxy-24-methylene-23-oxolanost-8-en-26-oic acid G. applanatum (fruit bodies) [69]
147 3α-Carboxyacetoxy-24-methyl-23-oxolanost-8-en-26-oic acid G. applanatum (fruit bodies) [69]
148 Fornicatin C ((3β)-3-hydroxy-18(13→12β)-abeo-lanosta-13(17),24-dien-18-oic acid) G. fornicatum (fruit bodies) [70]
149 3-Epipachymic acid (3α-acetoxy-16α-hydroxy-24-methylene-5α-lanost-8-en-21-oic acid) G. resinaceum (fruit bodies) [62]
150 3β, 15α-Diacetoxylanosta-8,24-dien-26-oic acid G. lucidum (mycelia) [71]
151 Tsugaric acid C ((24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid) G. tsugae (fruit bodies) [60]
152 Ganoderic acid V1 ((24E)-3β, 20ξ-dihydroxy-7,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid) G. lucidum [72]
153 Tsugaric acid B (3α-acetoxy-16α-hydroxy-24ξ-methyl-5α-lanosta-8,25-dien-21-oic acid) G. tsugae [61]
154 Methyl ganoderenate E (7β, 12β-dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate) G. lucidum (fruit bodies) [64]
155 8β, 9α-Dihydroganoderic acid C G. lucidum (mycelia) [65]

Table 7.

Ganoderma triterpenes (197213) in Figure 20.

No. Compound Name Source Ref.
197 Lucialdehyde A ((24E)-3β-hydroxy-5α-lanosta-7,9(11),24-trien-26-al) G. lucidum (fruit bodies) [25]
198 Ganoderiol a triacetate (3β, 24,26-triacetoxy-5α-lanosta-7, 9(11)-dien-25-ol) G. sinense (fruit bodies) [86]
199 Ganoderal A G. lucidum [23]
200 Ganoderol A G. lucidum [23]
201 Lucidumol B ((24S)-lanosta-7,9(11)-diene-3β, 24,25-triol) G. lucidum (spores) [38]
202 Ganodermanontiol (24,25,26-trihydroxy-5α-lanosta-7,9(11)-dien-3-one) G. lucidum (spores) [67]
203 Ganoderiol A (5α-lanosta-7,9(11)-dien-3β, 24,25,26-tetraol) G. lucidum (fruit bodies) [77]
204 Ganodermanondiol G. lucidum (fruit bodies) [87]
205 Ganoderic acid X (3α-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) G. amboinense [88]
206 Ganoderic acid TR G. lucidum [89]
207 Ganodermic acid Ja (lanosta-7,9(11),24-trien-3α, 15α-dihydroxy-26-oic acid) G. lucidum (mycelia) [84]
208 Ganodermic acid Jb (lanosta-7,9(11),24-trien-3β, 15α-dihydroxy-26-oic acid) G. lucidum (mycelia) [84]
209 Ganodermic acid R (lanosta-7,9(11),24-trien-3α, 15α-diacetoxy-26-oic acid) G. lucidum [78]
211 15α-Hydroxy-3-oxo-5α-lanosta-7,9,24(E)-triene-26-oic acid G. lucidum [26]
212 15α, 26-Dihydroxy-5α-lanosta-7,9,24(E)-trien-3-one G. lucidum [26]
213 3β-Hydroxy-5α-lanosta-7,9,24(E)-trien-26-oic acid G. lucidum [26]

Table 8.

Ganoderma triterpenes (214221) in Figure 21 and Figure 22.

No. Compound Name Source Ref.
214 3α, 15α, 22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
215 3β, 15α, 22β-Trihydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
216 3α, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
217 3β, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
218 22β-Acetoxy-3α, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
219 22β-Acetoxy-3β, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acid G. lucidum (mycelia) [71]
220 Epoxyganoderiol B (24S, 25S-epoxy-26-hydroxy-5α-lanosta-7,9(11)-diene-3-one) G. lucidum [40]
221 Epoxyganoderiol C (24S, 25S-epoxy-5α-lanosta-7,9(11)-diene-3β, 26-diol) G. lucidum [40]

Table 9.

Ganoderma triterpenes (222260) in Figure 23.

No. Compound Name Source Ref.
222 Butyl lucidenate N G. lucidum (fruit bodies) [17]
223 Butyl lucidenate A G. lucidum (fruit bodies) [17]
224 20(21)-Dehydrolucidenic acid N (3β, 7β-dihydroxy-11,15-dioxo-25,26,27- trinorlanosta-8,20-dien-24-oic acid) G. sinense (fruit bodies) [33]
225 20-Hydroxylucidenic acid A (7β, 20ξ-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid) G. sinense (fruit bodies) [33]
226 Methyl lucidenate D (methyl 12β-acetoxy-3,7,11,15-tetraoxo-5α-lanost-8-en-24-oate) G. lucidum (fruit bodies) [53,54]
227 20(21)-Dehydrolucidenic acid A (7β-Hydroxy-3,11,15-trioxo-25,26,27-trisnorlanosta-8,20(21)-dien-24-oic acid) G. lucidum (fruit bodies) [90]
228 Methyl 20(21)-dehydrolucidenate A (methyl 7β-hydroxy-3,11,15-trioxo-25,26,27-trisnorlanosta-8,20(21)-dien-24-oate) G. lucidum (fruit bodies) [90]
229 Lucidenic acid N (3,7-dihydroxy-4,4,14-trimethyl-11,15-dioxo-5-chol-8-en-24-oic acid) G. lucidum (dried fruit bodies) [91,92]
230 Lucidenic acid D (12β-acetoxy-4,4,14α-trimethyl-3,7,11,15-tetraoxo-5α-chol-8-en-24-oic acid) G. lucidum (dried fruit bodies) [31]
231 Methyl lucidenate E G. lucidum (gills) [54]
232 Methyl lucidenate F G. lucidum (gills) [23,54]
233 Ethyl lucidenates A (ethyl 7β-hydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oate) G. lucidum (fruit bodies) [93]
234 3β-Oxo-formyl-7β, 12β-dihydroxy-4,4,14α-trimethyl-5α-chol-11,15-dioxo-8-en(E)-24-oic acid G. lucidum [24]
235 Lucidenic acid A (7β-hydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oic acid) G. lucidum (dried fruit bodies) [94]
236 Lucidenic acid B (7β, 12-dihydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oic acid) G. lucidum (dried fruit bodies) [94]
237 Lucidenic acid C (3β, 7β, 12-trihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oic acid) G. lucidum (dried fruit bodies) [94]
238 4,4,14α-Trimethyl-3,7-dioxo-5α-chol-8-en-24-oic acid G. lucidum [26]
239 Lucidenic acid P (3β, 7β-dihydroxy-12β-acetoxy-25,26,27-trinor-11,15-dioxo dioxolanost-8-en-24-oic acid) G. lucidum (fruit bodies) [95]
240 Methyl lucidenate P G. lucidum (fruit bodies) [95]
241 Methyl lucidenate Q (methyl-7β, 15α-dihydroxy-25,26,27-trinor-3,11-dioxolanost-8-en-24-oate) G. lucidum (fruit bodies) [95]
242 3β-Hydroxy-4,4,14-trimethyl-7,11,15-trioxochol-8-en-24-oic acid G. lucidum (fruit bodies) [28]
243 Methyl lucidenate D2 G. lucidum (gill surface) [30]
244 Methyl lucidenate E2 G. lucidum (gill surface) [30]
248 Methyl lucidenate N (methyl 3β, 7β-dihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oate) G. lucidum (fruit bodies) [96]
249 t-Butyl lucidenate B (t-butyl 7β, 12β-dihydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oate) G.lucidum (fruit bodies) [96]
250 Methyl lucidenate A G. lucidum (fruit bodies) [93]
251 Lucidenic acid D2 G. lucidum (fruit bodies) [95]
252 20-Hydroxylucidenic acid D2 ((20ξ)-12β-acetoxy-20-hydroxy-3,7,11,15-tet-raoxo-25,26,27-trisnorlanost-8-en-24-oic acid) G. lucidum (fruit bodies) [90]
253 20-Hydroxylucidenic acid F ((20ξ)-20-hydroxy-3,7,11,15-tetraoxo-25,26,27-trisnorlanost-8-en-24-oic acid) G. lucidum (fruit bodies) [90]
254 20-Hydroxylucidenic acid E2 (12β-acetoxy-3β-hydroxy-7,11,15-trioxo-25,26,27-trisnorlanost-8-en-24-oic acid) G. lucidum (fruit bodies) [90]
255 20-Hydroxylucidenic acid N ((20ξ)-3β, 7β, 20-trihydroxy-11,15-dioxo-25,26,27-trisnorlanost-8-en-24-oic acid) G. lucidum (fruit bodies) [90]
256 20-Hydroxylucidenic acid P ((20ξ)-12β-acetoxy-3β, 7β, 20-trihydroxy-11,15-dioxo-25,26,27-trisnorlanost-8-en-24-oic acid) G. lucidum (fruit bodies) [90]
257 Lucidenic acid F G. lucidum (gills) [22]
258 Methyl lucidenate C G. lucidum [26]
259 Lucidenic acid E2 G. lucidum (fruit bodies) [95]
260 Lucideric acid A G. lucidum [26]

Table 10.

Ganoderma triterpenes 261280 in Figure 24, Figure 25, Figure 26, Figure 27, Figure 28, Figure 29, Figure 30 and Figure 31.

No. Compound Name Source Ref.
261 4,4,14α-Trimethyl-5α-chol-7,9(11)-dien-3-oxo-24-oic acid G. lucidum (dried fruit bodies) [73]
262 Ganoderic acid Jd (15α-hydroxy-3-oxo-5α-lano-sta-7,9(11)-dien-24-oic acid) G. sinense (fruit bodies) [47]
263 Methyl lucidenate H (methyl 3β, 7β-dihydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-11,15-dioxo-5α-chol-8-en-24-oate) G. lucidum (fruit bodies) [64]
264 Methyl lucidenate I (3β-hydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-7,11,15-trioxo-5α-chol-8-en-24-oate) G. lucidum (fruit bodies) [64]
265 Methyl lucidenate J (3β, 12β-dihydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-7,11,15-trioxo-5α-chol-8-en-24-oate) G. lucidum (fruit bodies) [64]
266 Methyl lucidenate Ha G. sinense (fruit bodies) [47]
267 Colossolactone I ((22S)-3-β-hydroxylanosta-8,24-dien-26,22-olide) G. colossum [97]
268 Colossolactone II ((22S)-1,3-β-dihydroxylanosta-8,24-dien-26,22-olide) G. colossum [97]
269 Colossolactone D G. colossum (fruit bodies) [98]
270 Colossolactone E G. colossum (fruit bodies) [98]
271 Colossolactone F G. colossum (fruit bodies) [98]
272 Colossolactone G G. colossum (fruit bodies) [98]
273 Ganosporelactone A G. lucidum (spores) [99]
274 Ganosporelactone B G. lucidum (spores) [99]
275 Ganosinensin B (ganodermanontriol 24-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)-2-oxo-ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9-dienate) G. sinense (fruit bodies) [100]
276 Ganosinensin C (ganodermanontriol 24-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9- dien-ate) G. sinense (fruit bodies) [100]
277 Ganodermacetal (methyl 7β, 15α-isopropylide-nedioxy-3β-hydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) G. amboinense (fruit bodies) [85]
278 Methyl ganoderate A acetonide (methyl 7β, 15α-isopropylidenedioxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) G. lucidum (fruit bodies) [16]
279 Applanoxidic acid A (15α-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid) G. applanatum [101]
280 Applanoxidic acid B (3β-hydroxy-7α, 8α-epoxy-12,15,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid) G. applanatum [101]

Table 11.

Ganoderma triterpenes 281287, 288307, 308311, 312, 313315, 316 in Figure 32, Figure 33, Figure 34, Figure 35, Figure 36, Figure 37, Figure 38, Figure 39 and Figure 40.

No. Compound Name Source Ref.
281 Applanoxidic acid C (20-hydroxy-7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),16-dien-26-oic acid) G. applanatum [101]
282 Applanoxidic acid D (3β, 20-dihydroxy-7α, 8α-epoxy-12,15,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid) G. applanatum [101]
283 Lanosta-7,9(11),24-trien-3-one15,26-dihydroxy G. zonatum Murill. [27]
284 Lanosta-7,9(11),24-trien-26-oic,3-hydroxy G. zonatum Murill. [27]
285 Ganoderic acid Y ((24E)-3-ol-5α-lanosta-7,9(11),24-trien-26-oic acid) G. zonatum Murill. [27]
286 Applanoxidic acid E (15β-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid) G. applanatum [66]
287 Applanoxidic acid F (7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),20E-dien-26-oic acid) G. applanatum [66]
288 Ganosinensin A (ganodermanontriol 26-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)-2-oxo-ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9-dienate}) G. sinense (fruit bodies) [100]
289 Colossolactone III ((22S)-3β, 19-epoxy-lanosta-8,24-dien-26,22-olide) G. colossum [97]
290 Colossolactone IV ((22S)-A,B-dihomo-19-nor-4-oxalanosta-8,24-dien-26,22-olide) G. colossum [97]
291 Colossolactone VIII ((22S, 23R)-A,B-dihomo-19-nor-15-β-acetoxy-23-hydroxy-4-oxa-3-oxolanosta-1,8,19,24-tetraen-26,22-olide) G. colossum [102]
292 Austrolactone ((23S, 25S)-12α, 23-epoxy-3β, 15β, 20α-trihydroxy-7,11-dioxo-5α-lanosta-8,16-dien-23,26-olide) G. australe [103]
293 Ganolactone B (3β, 7β-dihydroxy-11,15-dioxolanosta-8-en-24→20 lactone) G. sinense (fruit bodies) [86]
294 Ganolactone (7β-hydroxy-3,11,15-trioxo-lanosta-8-en-24→20s lactone) G. lucidum (fruit bodies) [104]
295 Colossolactone B G. colossum (fruit bodies) [98]
296 Colossolactone C G. colossum (fruit bodies) [98]
297 3α-(3-Hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5α-lanost-8-en-21-oic acid G. resinaceum (fruit bodies) [62]
298 Colossolactone A G. colossum (fruit bodies) [98]
299 Methyl ganosinensate A G. sinense (fruit bodies) [56]
300 Ganosinensic acid A G. sinense (fruit bodies) [56]
301 Ganosinensic acid B G. sinense (fruit bodies) [56]
302 Tsugarioside C (3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside) G. tsugae (fruit bodies) [60]
303 Ganorbiformin A G. colossum (fruit bodies) [46]
304 Colossolactone V ((22R)-3,4-seco-19,22-diacetoxy-4-hydroxylanosta-8,24(Z)-dien-3,26-dioic acid 3-methyl-ester) G. colossum (fruit bodies) [102]
305 Colossolactone VI ((22R)-3,4-seco-19,22-diacetoxy-4-hydroxylanosta-7,9(11),24(Z)-trien-3,26-dioic acid 3-methyl ester) G. colossum (fruit bodies) [102]
306 Colossolactone VII ((22S)-3,4-seco-19-acetoxy-4-hydroxylanosta-8,24-dien-26,22-olide 3-methyl ester) G. colossum (fruit bodies) [102]
307 Furanoganoderic acid (21,23-epoxy-15α-hydroxy-3,7,1l-trioxo-5α-lanosta-8,20(21),22-trien-26-oic acid) G. applanatum (fruit bodies) [52]
308 Fornicatin B (7β-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-4(28),8-dien-3,24-dioic acid) G. fornicatum (fruit bodies) [105]
309 Fornicatin G (7β-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-4(28),8-dien-24-oic-3-acetyl ester) G. cochlear (sporophore) [106]
310 Fornicatin A (4, 7β-epoxy-28-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-8-en-3,24-dioic acid) G. fornicatum (fruit bodies) [105]
311 Fornicatin H (4, 7β-epoxy-28-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlansta-8-en-3,24-diester) G. cochlear (sporophore) [106]
312 Australic acid ((20Z, 23R, 25R)-15α-acetyl-7α, 8α-epoxy-12-oxo-3,4-seco-5α-lanosta-4(28),9,20(22)-trien-23,26-olid-3-oic acid) G. australe [103]
313 Lucidone A G. tsugae [107]
314 Lucidenol G. tsugae [107]
315 Ganosineniol A G. sinense (fruit bodies) [47]
316 8α, 9α-Epoxy-4,4,14α-trimethyl-3,7,11,15,20-pentaoxo-5α-pregnane G. concinna [75]

Figure 26.

Structures of compounds 267268.

Figure 26

Cpd R
267 H
268 β-OH

Figure 27.

Structures of compounds 269272.

Figure 27

Cpd R1 R2 R3
269 α-H β-H β-OH
270 α-H β-H β-O-Ac
271 α-H β-OH β-O-Ac
272 ξ-OH H β-O-COCH3

Figure 28.

Structures of compounds 273274.

Figure 28

Cpd R
273 =O
274 β-OH

Figure 29.

Structures of compounds 275276.

Figure 29

Cpd R
275 =O
276 H

Figure 30.

Structures of compounds 277278.

Figure 30

Cpd R1 R2
277 β-OH COOH
278 =O COOCH3

Figure 31.

Structures of compounds 279280.

Figure 31

Cpd R1 R2
279 =O α-OH
280 β-OH =O

Figure 32.

Structures of compounds 281282.

Figure 32

Cpd R
281 =O
282 β-OH

Figure 33.

Structures of compounds 283285.

Figure 33

Cpd R R2
283 α-OH COOH
284 =O CH2OH
285 β-OH COOH

Figure 34.

Structures of compounds 286287.

Figure 34

Cpd R
286 α-OH
287 =O

Figure 35.

Figure 35

Figure 35

Structures of compounds 288307.

Figure 36.

Structures of compounds 308309.

Figure 36

Cpd R
308 COOH
309 COOCH2CH3

Figure 37.

Structure of compounds 310311.

Figure 37

Cpd R1 R2
310 COOH COOH
311 COOCH3 COOCH3

Figure 38.

Figure 38

Structure of compound 312.

Figure 39.

Structures of compounds 313315.

Figure 39

Cpd R1 R2
313 =O =O
314 =O OH
315 α-OH CH2OH

Figure 40.

Figure 40

Structure of compound 316.

3. 13C-NMR Data of Ganoderma Triterpenes

The reported GTs 13C-NMR data are shown in Table 12. For compounds 5, 7, 22, 23, 28, 3134, 36, 37, 54, 55, 59, 89, 95, 97, 98, 110, 112, 114, 121123, 130132, 146, 147, 154, 159, 169, 195, 199, 200, 206, 211213, 235237, 240, 245247, 250, 251, 257260, 265, 283285, 313 and 314 have no 13C-NMR data reported or cannot be researched.

Table 12.

The 13C-NMR spectural data of compounds 1316 except those which have no reported 13C-NMR data.

NO. 1b) 2b) 3b) 4b) 6b) 8b) 9b) 10b) 11b) 12b) 13b) 14b) 15b) 16b) 17b) 18b) 19b) 20b)
C1 33.4 35.7 35.0 33.1 35.1 34.4 35.7 35.6 34.8 34.8 35.0 34.7 35.7 35.7 34.6 34.3 34.8 34.2
C2 27.5 34.5 27.9 27.2 34.2 28.0 34.4 34.4 27.6 28.3 28.0 28.2 34.3 34.3 27.8 27.7 34.1 27.3
C3 77.5 217.1 78.5 77.3 217.7 78.7 208.4 208.7 78.3 78.5 77.5 78.2 217.5 217.5 78.2 77.5 217.8 78.5
C4 40.6 46.8 39.0 39.0 47.0 39.0 47.0 46.7 38.8 39.0 38.9 38.6 46.8 46.8 38.6 40.2 47.2 39.1
C5 51.5 49.0 49.3 51.2 51.7 51.8 49.2 48.8 49.2 45.7 49.5 49.1 49.0 49.0 49.1 49.8 45.2 47.7
C6 36.8 29.3 26.7 36.6 18.7 17.4 29.2 29.1 26.6 27.8 27.6 27.8 27.7 27.8 28.2 36.5 27.9 28.0
C7 199.1 69.1 67.1 199.0 29.6 30.4 69.1 68.9 66.9 67.0 69.5 69.5 66.4 66.3 69.5 205.3 66.7 68.0
C8 151.9 159.1 157.1 145.6 163.2 162.9 159.6 159.5 156.8 155.0 159.6 158.0 157.8 157.8 158.1 154.6 159.3 158.8
C9 145.9 140.5 142.9 151.7 138.6 140.0 140.6 140.1 142.7 142.9 142.2 142.0 141.3 141.3 141.9 149.8 140.0 141.6
C10 39.3 38.2 38.8 40.3 37.1 37.8 46.8 46.8 38.6 45.4 38.9 38.6 38.3 38.3 38.5 38.9 38.0 38.6
C11 194.2 199.6 198.0 193.9 198.1 198.3 200.0 199.7 197.9 200.0 201.2 199.8 197.6 197.6 199.9 201.3 199.1 199.4
C12 79.3 51.9 50.5 79.1 51.7 52.1 51.9 51.8 50.3 51.0 52.3 52.0 50.2 50.2 51.9 52.3 51.8 52.2
C13 48.1 47.0 45.5 47.9 46.8 47.2 38.2 38.0 45.4 38.8 47.4 47.1 45.0 45.0 47.1 48.0 46.4 46.1
C14 58.7 54.1 59.6 58.5 53.6 53.5 54.2 54.1 59.4 58.5 54.4 54.0 59.4 59.4 54.0 52.8 53.4 53.5
C15 205.9 72.7 217.7 66.2 72.9 73.0 72.6 72.4 217.5 207.5 72.4 72.4 216.6 216.4 72.5 72.1 72.4 72.3
C16 38.1 36.7 41.1 38.0 38.6 38.7 36.2 36.3 40.9 41.0 35.9 36.2 41.0 41.0 36.1 36.3 37.8 37.8
C17 44.9 48.4 45.8 44.6 48.7 48.7 48.3 48.2 45.6 49.2 48.5 48.1 45.7 45.8 48.1 48.2 49.0 49.0
C18 12.3 17.5 17.6 12.1 17.2 17.1 17.4 17.3 17.4 17.2 17.2 17.1 17.7 17.7 17.1 17.4 17.5 17.3
C19 18.1 19.5 18.7 17.9 19.0 19.0 19.6 19.4 18.5 17.6 19.6 19.5 18.2 18.2 19.6 17.6 17.5 17.3
C20 29.6 32.8 32.1 29.4 32.6 32.5 32.8 32.8 32.0 32.1 33.0 32.7 32.0 32.0 32.7 32.4 32.5 32.5
C21 21.8 19.7 19.8 21.5 19.4 19.4 19.4 19.7 19.6 19.8 19.7 19.6 19.6 19.7 19.6 19.5 19.3 19.3
C22 48.6 49.9 49.4 48.5 49.6 49.7 49.8 49.7 49.0 49.3 50.0 49.8 49.0 49.1 49.7 49.5 49.6 49.6
C23 207.7 208.6 207.9 206.1 208.3 208.3 217.3 217.4 207.6 215.9 210.0 208.5 207.5 207.6 208.7 208.2 208.3 208.3
C24 46.8 46.9 46.8 46.6 46.8 46.8 46.7 46.8 46.6 46.9 46.9 46.7 46.6 46.8 46.7 46.8 46.9 46.9
C25 34.9 35.0 35.1 35.1 34.7 34.6 34.8 34.8 34.6 34.9 35.0 34.7 34.5 34.7 34.6 34.7 34.7 34.7
C26 175.9 176.0 175.9 181.0 176.2 176.1 27.4 27.5 180.3 26.8 178.5 176.2 180.3 176.1 176.3 176.1 176.2 176.4
C27 17.3 17.3 17.3 17.1 17.1 17.1 180.1 176.3 16.9 176.2 17.2 17.1 16.9 17.1 17.1 17.1 17.1 17.1
C28 28.1 27.5 28.4 27.8 -- -- -- -- -- -- -- -- -- -- -- -- -- --
C29 15.7 20.9 15.6 15.5 -- -- -- -- -- -- -- -- -- -- -- -- -- --
C30 21.5 19.8 24.6 21.2 27.8 28.3 17.0 17.2 28.2 15.5 28.3 28.2 27.0 27.0 28.2 27.8 27.6 28.2
OCOCH3 Bu1' Bu1' CH3CO C31 C31 C31 C31 C31 C31 C31 C31 C31 C31 C31 C31 C31 C31
170.4 64.8 64.8 170.2 20.6 15.7 20.8 20.8 15.5 24.5 15.9 15.7 20.8 20.8 15.7 15.4 20.5 15.8
OCOCH3 Bu 2' Bu 2' CH3CO C32 C32 C32 C32 C32 C32 C32 C32 C32 C32 C32 C32 C32 C32
21.0 30.9 30.9 20.9 18.8 18.8 19.8 19.7 24.4 18.7 19.5 19.4 24.7 24.7 19.4 20.3 21.1 21.1
N-BU1' Bu 3' Bu3' OCH3 OCH3 COOCH3 COOCH3 COOCH3 COOCH3 OCH3 OCH3 OCH3 OCH3
64.8 19.3 19.3 51.9 51.8 52.0 51.7 51.9 51.9 51.9 51.9 51.9 51.9
NO. 21b) 24b) 25b) 26b) 27c) 29b) 30b) 35c) 38b) 39b) 40b) 41b) 42d) 43b) 44a) 45b) 46b) 47c)
C1 34.5 33.9 34.4 34.5 35.4 37.4 37.2 35.2 35.6 35.7 34.4 33.8 34.0 34.8 36.0 35.4 34.8 35.2
C2 24.0 33.6 27.4 28.4 34.7 34.1 34.6 27.6 34.4 34.5 27.4 27.5 33.5 27.4 34.5 34.3 28.8 33.9
C3 79.9 215.1 78.2 78.4 221.0 214.9 215.4 78.0 216.8 218.0 78.2 78.5 215.5 78.0 215.9 214.6 78.0 218.6
C4 38.0 46.8 38.6 40.7 47.2 46.9 47.0 39.1 46.2 47.0 38.5 38.8 38.7 39.0 47.0 47.2 39.8 46.4
C5 49.2 50.8 49.1 53.0 45.7 51.0 50.9 49.8 48.8 49.0 49.1 51.3 49.7 49.9 48.7 50.4 50.7 48.3
C6 26.6 37.4 36.7 37.8 28.1 33.7 33.8 27.4 27.6 29.2 26.6 17.3 36.8 36.6 28.8 37.1 36.7 28.1
C7 66.1 198.6 66.2 201.1 67.1 198.6 199.4 67.0 66.3 69.2 66.2 29.3 199.6 199.1 66.0 198.0 199.0 68.2
C8 157.4 149.8 155.8 151.9 161.8 149.9 149.8 157.3 157.8 159.2 155.9 161.5 146.1 138.9 159.7 139.8 138.9 160.4
C9 141.6 145.9 142.9 153.6 140.2 146.1 146.8 143.1 141.2 140.6 142.0 140.1 149.0 164.9 140.9 162.6 164.7 139.6
C10 37.5 39.2 38.5 42.4 38.4 39.4 39.3 38.9 38.2 38.2 38.5 37.5 46.4 39.8 38.4 39.4 38.9 37.6
C11 199.3 194.1 192.0 195.0 72.0 194.1 199.4 200.3 197.7 200.1 192.1 191.6 199.8 23.7 198.2 23.8 23.6 200.3
C12 77.9 78.9 79.5 199.8 52.4 79.0 48.9 78.4 50.1 52.0 79.8 80.1 48.5 30.2 50.9 30.1 30.2 51.5
C13 51.9 47.6 49.6 62.2 47.6 47.7 43.9 52.4 44.9 46.9 49.9 51.5 56.8 45.0 45.2 45.0 45.0 46.3
C14 60.3 58.7 60.6 61.3 54.1 58.7 57.2 60.9 59.3 54.1 60.5 53.9 43.5 47.8 59.0 47.8 49.0 53.7
C15 216.8 205.6 216.2 207.5 201.0 205.5 207.0 217.8 218.1 72.9 216.4 74.6 207.8 32.0 217.0 28.7 27.5 71.6
C16 38.3 37.8 37.9 40.8 35.3 37.8 39.8 38.6 41.2 36.7 37.3 33.6 39.9 28.8 42.0 31.8 32.0 35.6
C17 45.7 44.3 45.2 40.7 49.5 44.5 44.3 46.6 46.7 48.7 46.1 48.6 44.4 49.0 46.8 49.0 49.9 48.5
C18 12.0 12.0 12.0 13.5 17.8 12.1 16.0 12.3 17.7 17.4 13.4 12.3 15.4 15.8 17.8 15.9 15.3 16.6
C19 18.8 18.7 18.6 18.6 17.9 18.7 18.6 19.1 18.2 19.6 18.6 19.0 18.4 18.4 18.2 17.9 18.4 18.9
C20 28.7 29.4 28.2 33.8 33.2 29.5 32.1 29.1 35.5 36.2 35.5 34.1 32.9 36.2 33.9 36.2 36.3 33.1
C21 21.3 21.6 21.9 20.4 19.5 21.6 19.8 21.8 18.2 18.5 20.8 19.7 19.7 18.6 19.8 18.6 18.6 19.0
C22 48.3 48.4 47.9 50.2 50.0 48.4 48.8 48.7 34.5 34.8 33.1 33.7 42.8 34.8 43.8 34.7 34.8 42.9
C23 208.1 207.6 207.4 211.1 210.7 207.3 207.6 210.3 25.6 25.9 26.5 26.3 65.4 25.9 66.5 26.0 26.0 65.9
C24 46.1 46.6 46.6 48.0 47.2 46.4 46.5 46.9 144.1 145.3 143.2 144.2 144.4 145.6 145.0 155.2 155.3 143.2
C25 34.2 34.7 34.6 36.6 37.4 34.6 34.6 35.4 127.0 127.2 127.1 127.2 126.9 126.6 128.8 139.2 139.2 128.4
C26 180.5 175.6 176.1 180.7 179.0 180.8 180.9 178.8 171.2 172.0 171.0 172.7 169.0 172.4 170.7 195.3 195.3 170.2
C27 16.9 17.1 17.1 18.0 17.4 16.9 16.9 17.3 12.1 12.3 12.1 12.0 12.7 12.0 13.4 9.2 9.2 12.3
C28 27.9 27.6 28.0 28.7 27.8 -- -- -- 24.7 19.7 24.1 28.2 27.0 25.0 27.0 25.4 27.5 27.0
C29 16.4 20.3 15.4 16.6 20.7 -- -- -- 26.9 27.6 28.1 15.7 19.9 27.5 20.8 21.4 15.8 20.1
C30 23.0 20.7 24.0 24.9 21.4 27.6 27.6 28.4 20.7 20.9 15.4 19.8 20.0 15.3 25.1 24.9 25.0 19.0
C31 CH3CO CH3CO C31 C31 C31 CH3CO 12-COCH3
161.0 170.2 170.4 20.4 20.3 15.8 170.1 170.5
CH3CO CH3CO C32 C32 C32 CH3CO 12-COCH3
20.9 20.9 20.8 21.0 23.5 20.7 21.0
OCH2CH3 OCH3 OCOCH3 15-COCH3
60.7 51.9 170.2 170.6
NO 48c) 49c) 50c) 51c) 52c) 53b) 56b) 57b) 58b) 60b) 61b) 62b) 63b) 64b) 65b) 66a) 67a) 68a)
C1 34.9 35.7 33.6 34.4 33.2 34.7 30.1 35.0 35.3 34.8 34.5 34.7 34.6 35.4 35.2 35.5 35.2 35.2
C2 34.3 28.0 26.9 27.1 26.7 27.6 23.3 34.1 34.3 34.6 34.4 27.3 27.3 34.4 34.3 29.0 28.9 34.1
C3 219.5 78.7 77.2 78.0 76.8 78.3 77.3 215.5 214.6 214.4 214.9 77.8 77.8 214.6 217.2 77.6 77.9 218.4
C4 46.6 39.7 39.0 38.4 40.0 38.8 36.2 46.9 47.2 47.5 47.4 38.8 38.8 47.2 46.6 39.3 39.7 45.9
C5 45.3 50.0 50.8 49.0 51.2 49.1 40.5 49.8 50.4 50.8 51.6 49.7 49.8 49.0 44.8 49.9 52.4 48.6
C6 27.7 27.6 36.2 26.5 36.4 26.6 26.1 37.1 37.1 37.5 37.2 36.5 36.5 37.2 28.4 28.8 30.9 28.8
C7 66.6 67.7 199.9 66.2 199.5 66.8 70.0 201.3 198.1 199.4 199.8 199.0 198.9 198.0 66.2 69.4 17.9 68.6
C8 160.9 158.4 148.6 156.6 146.2 156.9 131.1 151.5 139.6 142.1 139.7 138.9 138.8 139.6 134.8 160.5 164.8 159.8
C9 139.7 143.9 151.8 142.0 151.0 142.7 145.1 149.8 162.7 158.7 160.6 164.8 164.6 162.8 140.1 141.3 139.8 140.3
C10 37.9 39.4 40.4 38.1 38..8 38.6 38.3 38.8 39.4 40.1 39.7 39.7 39.7 39.4 38.1 39.1 38.3 37.5
C11 200.1 200.1 200.1 199.5 201.4 198.0 21.4 201.8 23.8 65.8 67.2 23.6 23.5 23.8 20.8 200.1 198.6 199.8
C12 52.0 51.2 49.6 78.2 77.6 50.3 31.2 51.2 30.1 44.6 42.7 30.0 30.1 30.2 31.2 52.9 52.9 51.6
C13 47.0 46.4 44.2 51.7 49.5 45.3 45.8 46.7 44.9 47.6 43.4 44.8 44.9 45.0 45.3 47.6 47.4 46.2
C14 53.4 60.3 57.0 60.1 57.5 59.3 52.1 48.7 47.8 48.1 48.9 47.7 47.7 47.8 51.2 54.7 54.0 53.7
C15 71.7 218.5 209.0 217.4 207.6 217.9 72.4 31.9 31.9 32.6 31.9 31.9 31.9 28.7 76.4 72.4 72.1 72.1
C16 37.5 42.0 45.6 36.8 36.7 41.1 39.7 27.43 28.7 27.9 28.7 28.7 28.7 31.9 36.4 37.5 39.6 36.2
C17 49.7 47.2 42.7 46.2 45.5 46.1 48.8 49.1 49.0 49.7 48.1 48.9 48.9 50.5 49.3 49.5 49.9 47.5
C18 17.3 17.6 15.9 11.9 10.6 17.4 16.3 16.9 15.9 16.9 17.3 15.7 15.7 15.9 16.6 17.4 17.0 17.0
C19 17.5 18.8 17.6 18.6 17.6 18.4 17.7 17.9 17.9 19.2 19.5 18.2 18.2 17.9 17.3 19.9 19.4 19.3
C20 33.5 34.0 33.1 28.5 29.4 35.5 36.2 36.1 36.2 36.0 36.2 36.1 36.1 36.2 36.2 34.6 34.4 35.9
C21 19.2 20.0 19.3 22.0 21.3 18.2 18.4 18.3 18.7 18.4 18.6 18.6 18.5 18.4 18.2 20.2 19.9 18.4
C22 43.3 43.7 40.4 41.3 41.8 37.4 34.7 34.5 35.9 34.6 34.6 35.8 34.7 34.7 34.6 44.5 44.4 34.4
C23 66.4 66.8 65.9 67.0 66.5 25.6 25.8 25.92 24.5 25.8 25.8 24.4 25.9 25.9 25.9 67.0 66.9 26.0
C24 142.4 144.2 142.8 142.7 142.2 143.9 145.2 154.6 126.8 145.3 145.3 126.8 155.1 145.5 144.9 145.4 145.4 156.3
C25 130.2 129.6 128.8 129.3 129.0 127.5 126.8 139.4 134.4 126.8 126.7 134.3 139.1 126.5 126.7 128.7 128.7 138.6
C26 172.0 171.2 170.8 170.8 175.0 172.3 172.4 195.2 69.0 172.7 172.7 69.0 195.3 172.5 171.2 170.8 170.8 194.4
C27 13.1 13.1 12.6 12.8 12.6 12.1 12.0 9.2 13.6 11.9 11.9 13.5 9.0 12.0 12.1 13.5 13.5 9.2
C28 27.5 28.6 27.5 27.9 27.4 28.1 27.2 27.44 25.4 25.1 25.1 24.9 24.9 25.0 26.5 28.8 28.9 20.8
C29 20.5 16.1 15.3 15.2 15.2 15.4 22.7 20.3 21.4 21.6 21.8 27.3 27.3 25.9 21.2 16.7 16.7 27.5
C30 21.0 24.9 21.6 22.9 20.1 24.4 17.9 25.87 24.9 25.3 24.9 15.2 15.2 21.4 20.1 20.2 19.8 19.1
COCH3
171.9
COCH3
21.9
NO. 69c) 70b) 71b) 72b) 73b) 74b) 75b) 77b) 78b) 79b) 80b) 81b) 82b) 83h) 84b) 85b) 86b) 87b)
C1 34.9 30.3 30.3 30.1 30.2 30.3 30.3 30.3 34.5 34.8 35.2 35.3 35.3 31.3 30.0 33.3 35.9 35.6
C2 34.0 23.3 23.3 23.3 23.4 23.2 23.3 23.3 23.8 27.4 34.2 34.3 34.3 24.3 23.3 27.3 34.5 34.2
C3 219.6 77.5 77.5 77.3 77.6 77.3 77.5 77.6 79.6 77.9 217.2 217.4 217.4 77.7 77.2 77.4 216.7 216.4
C4 46.8 36.3 36.3 36.2 36.4 36.5 36.4 36.3 37.8 38.9 46.6 46.7 46.7 37.2 36.3 39.1 47.0 46.7
C5 51.3 40.1 40.0 40.5 40.4 40.1 40.5 40.2 49.9 49.8 44.7 45.0 45.0 40.8 39.6 51.2 49.2 48.8
C6 18.4 27.4 27.4 26.0 22.4 21.3 28.1 28.9 36.4 36.6 28.4 30.0 23.3 28.5 21.3 36.5 27.9 27.6
C7 29.3 66.5 66.5 69.9 76.5 76.3 66.8 67.0 198.6 198.9 66.1 66.7 76.1 67.1 75.9 198.5 66.5 66.2
C8 165.1 133.9 133.8 131.1 134.3 132.8 134.5 135.6 138.9 138.8 134.6 136.4 135.3 141.7 142.9 145.8 157.8 157.3
C9 137.9 141.8 141.8 145.0 141.3 143.6 141.7 141.3 164.4 164.6 140.1 139.4 139.5 135.1 132.7 151.9 141.4 141.2
C10 36.8 38.4 38.4 38.3 38.1 38.4 38.1 38.2 39.6 39.8 38.1 37.9 37.8 39.2 38.7 40.5 38.6 38.3
C11 199.1 20.7 20.7 21.2 21.0 20.9 20.6 21.0 23.6 23.6 20.7 21.3 21.0 21.5 21.1 193.5 197.5 196.8
C12 51.6 31.2 31.2 31.2 31.1 31.4 31.7 31.0 30.1 30.1 31.2 31.0 31.1 32.1 30.7 78.5 49.2 48.9
C13 46.4 45.5 45.3 45.6 45.0 46.2 45.7 45.0 44.9 44.9 45.1 45.0 44.9 46.0 45.6 57.8 45.9 45.9
C14 53.3 51.2 51.3 52.1 50.0 52.8 52.4 49.7 47.8 47.8 51.2 49.7 49.9 52.4 51.7 48.7 58.8 58.6
C15 72.0 76.5 76.0 72.2 30.2 72.0 72.4 29.8 31.9 31.9 75.9 29.9 30.1 76.0 75.2 204.6 217.3 216.6
C16 38.1 36.6 36.3 39.3 27.9 37.3 38.1 27.9 28.5 28.5 36.1 27.9 27.8 37.3 37.1 37.6 38.1 37.8
C17 49.0 49.3 45.9 45.5 47.2 46.4 46.4 47.1 45.6 45.7 45.9 47.1 47.2 46.9 45.2 48.9 48.3 49.7
C18 16.7 16.5 16.3 16.2 15.9 16.6 16.4 15.9 15.6 15.6 16.4 16.0 16.0 17.0 16.1 13.3 19.2 19.0
C19 18.6 17.5 17.5 17.7 17.5 17.2 17.3 17.3 18.5 18.4 17.3 17.3 17.4 18.0 17.6 17.8 18.4 18.1
C20 33.1 36.3 39.9 39.5 39.8 39.3 39.5 39.7 39.5 39.5 39.9 39.7 39.7 41.0 39.9 154.7 138.5 153.3
C21 18.8 18.2 12.7 12.9 12.9 13.0 12.9 12.8 13.1 13.1 12.6 12.8 12.8 13.6 12.7 21.1 18.3 21.0
C22 42.9 34.7 74.4 74.6 74.8 74.9 74.7 74.7 74.8 74.8 74.3 74.7 74.7 74.8 74.3 126.0 126.9 124.7
C23 66.0 25.9 31.9 31.7 31.9 31.9 31.9 31.8 31.8 31.8 31.9 31.8 31.8 32.8 31.8 197.8 74.5 197.9
C24 142.4 145.0 138.9 139.1 139.6 139.1 139.1 139.4 139.4 139.4 138.8 139.6 139.5 140.0 139.1 47.5 37.2 47.7
C25 129.5 126.8 129.5 129.3 129.1 129.3 129.3 129.2 129.0 129.0 129.5 129.2 129.0 130.2 129.3 34.4 34.5 34.8
C26 171.5 172.2 172.0 171.7 172.1 172.0 171.4 172.4 171.3 171.2 171.9 172.0 171.7 172.9 172.2 180.2 179.8 176.3
C27 12.7 12.0 12.3 12.3 12.3 12.3 12.4 12.3 12.3 12.3 12.3 12.3 12.3 13.1 12.3 17.0 16.0 17.2
C28 27.5 27.4 27.4 27.2 27.3 27.3 27.4 27.4 27.4 27.4 26.5 26.5 26.5 -- -- 27.9 27.3 27.0
C29 20.2 21.9 22.0 21.9 22.2 22.0 21.9 22.0 16.3 15.3 21.2 21.3 21.3 -- -- 15.5 21.0 20.8
C30 18.7 20.2 20.2 18.0 25.6 18.5 19.2 26.3 25.1 25.0 26.1 26.1 25.4 28.2 27.3 21.3 24.8 24.7
OCOCH3 COCH3 COCH3 COCH3 COCH3 COCH3 CO 3-OC- 22-OC- 15-OC- 22-OC- 7-OCH3 C31 C31 C31 OCH3
170.9 170.9 171.9 171.1 170.9 170.9 170.9 OCH3 OCH3 OCH3 OCH3 55.8 22.6 22.2 170.3 51.9
OCOCH3 COCH3 COCH3 COCH3 COCH3 COCH3 CO 170.8 170.6 170.5 170.7 C32 C32 C32
21.4 21.4 21.7 21.6 21.5 21.4 170.7 21.1 19.0 20.5
NO. 88c) 89c) 90b) 91b) 92b) 93h) 94h) 96h) 99b) 100b) 101b) 102b) 103b) 104b) 105b) 106b) 107b) 108b)
C1 35.5 34.8 34.8 35.6 35.1 34.9 35.2 34.5 35.7 37.3 37.5 36.6 34.6 35.2 33.4 35.0 35.1 35.9
C2 34.3 27.7 27.8 34.2 34.1 34.7 33.9 27.9 34.3 34.7 34.1 27.3 27.6 34.3 27.4 33.9 28.0 34.5
C3 217.4 78.3 78.1 216.5 215.9 213.3 213.0 77.0 217.5 217.2 214.8 77.3 78.3 216.8 77.5 215.4 78.6 216.8
C4 46.7 39.0 38.8 46.8 46.8 46.8 46.3 40.4 46.8 43.9 46.9 40.4 38.6 47.0 40.3 46.4 39.1 47.0
C5 48.8 49.2 50.0 48.9 49.2 48.5 49.0 50.1 49.0 50.9 51.0 51.4 49.2 49.5 51.5 49.0 49.4 49.2
C6 29.0 26.7 27.6 27.7 27.6 36.1 36.8 36.5 27.8 33.8 33.7 33.2 26.9 27.8 36.8 36.8 26.9 27.9
C7 68.9 66.9 69.4 66.3 65.8 198.4 204.5 205.0 66.3 199.3 198.7 198.7 66.2 65.8 198.8 204.6 67.1 66.5
C8 159.1 156.6 158.8 157.4 156.7 146.9 150.3 149.6 157.8 149.7 149.9 151.6 157.4 158.3 150.5 150.4 156.9 157.9
C9 140.3 142.8 142.0 141.4 141.6 149.5 152.6 154.6 141.3 146.8 146.1 145.7 141.9 140.5 147.1 152.3 142.7 141.3
C10 38.1 38.7 38.8 38.4 38.2 39.5 39.2 38.8 38.3 39.4 39.3 39.1 38.4 37.9 39.2 39.1 38.9 38.5
C11 199.1 198.0 200.0 197.8 191.8 198.1 199.8 200.1 197.6 199.3 194.1 193.9 199.3 199.5 201.6 201.2 198.0 197.8
C12 50.5 49.1 50.8 48.9 78.5 47.8 50.5 51.0 50.2 48.9 79.0 79.1 77.9 78.1 77.5 52.1 51.1 50.9
C13 48.1 46.3 49.3 46.0 50.3 44.8 48.6 49.2 45.0 47.0 47.7 47.9 51.9 51.7 49.8 47.8 46.0 45.7
C14 53.4 58.7 53.5 58.7 59.9 56.8 52.4 52.5 59.4 57.2 58.6 58.4 60.3 60.4 57.9 52.8 59.8 59.8
C15 72.7 216.4 72.5 216.4 215.1 204.9 72.9 72.9 216.4 206.8 205.4 205.5 216.8 215.5 206.0 71.8 217.9 218.0
C16 31.8 37.7 31.6 37.9 38.4 37.1 32.3 32.5 41.0 39.8 37.8 37.8 38.4 38.5 37.9 30.2 36.2 36.4
C17 52.2 49.7 52.4 49.7 50.1 50.8 52.0 52.1 45.8 44.5 44.5 44.7 45.8 45.8 45.3 50.9 50.2 50.4
C18 19.0 18.8 18.8 19.0 14.4 17.5 16.7 15.5 17.7 16.1 12.1 12.1 12.0 12.1 10.9 18.9 19.1 19.4
C19 19.9 18.4 19.7 18.1 18.1 18.4 17.4 17.3 18.2 18.6 18.7 17.9 18.8 18.3 18.1 17.5 18.6 18.4
C20 157.0 153.8 157.3 153.6 154.1 153.6 155.6 155.7 32.0 32.0 29.4 29.3 28.7 28.7 29.5 73.3 73.4 73.3
C21 21.3 21.0 21.3 20.9 20.3 21.5 21.1 21.1 19.7 19.8 21.6 21.6 21.4 21.4 21.3 26.6 26.4 26.3
C22 124.3 124.7 124.5 124.7 126.1 124.6 124.5 124.6 49.1 49.1 48.5 48.4 48.4 48.5 48.9 52.5 48.5 48.5
C23 198.6 197.2 199.6 196.9 197.8 197.2 197.4 197.3 207.6 207.6 207.4 207.4 208.1 208.1 208.1 211.2 74.8 74.8
C24 47.5 47.6 48.1 47.5 47.5 47.6 47.6 47.9 46.8 46.7 46.7 46.6 46.4 46.4 46.6 47.7 36.8 36.8
C25 35.1 34.8 34.8 34.8 34.4 35.1 35.2 35.2 34.7 34.6 34.7 34.6 34.6 34.7 34.7 34.5 33.8 33.7
C26 180.2 180.0 179.0 180.6 180.0 181.2 181.2 175.9 176.1 176.1 176.0 176.0 176.1 176.1 176.1 177.8 178.8 178.8
C27 17.1 17.1 17.3 17.0 17.0 17.0 17.0 17.3 17.1 17.1 17.1 17.0 17.1 17.1 17.1 17.0 16.1 16.1
C28 -- -- -- -- 26.6 27.2 27.0 27.7 -- -- -- -- -- -- -- 27.2 28.4 27.2
C29 -- -- -- -- 21.0 20.3 20.3 18.7 -- -- -- -- -- -- -- 20.2 15.7 21.0
C30 27.5 28.2 28.2 27.0 24.0 20.9 20.7 20.7 27.0 27.6 27.6 27.9 28.1 26.3 28.0 20.6 25.1 25.3
C31 C31 C31 C31 CH3CO CO- C31 C31 C31 C31 C31 C31 C31
20.7 15.5 15.8 20.8 170.6 OCH3 20.8 20.9 20.8 15.5 15.4 21.3 15.6
C32 C32 C32 C32 CH3CO 51.4 C32 C32 C32 C32 C32 C32 C32
19.4 24.4 19.5 24.7 20.6 24.7 20.3 20.4 21.2 23.1 23.3 20.3
NO. 109f) 111b) 113b) 115a) 116b) 117a) 118b) 119b) 120b) 124b) 125b) 126b) 127b) 128h) 129b) 133a) 134b) 135b)
C1 35.9 35.3 35.4 35.2 34.9 35.9 30.2 30.4 36.1 34.6 34.6 34.2 34.9 34.5 35.7 35.2 35.5 35.4
C2 28.4 34.4 34.4 28.9 27.5 28.5 23.3 23.4 34.7 27.5 27.7 27.3 27.8 33.9 34.3 34.3 34.4 34.3
C3 79.2 214.8 214.6 77.1 78.0 77.8 78.1 78.0 216.3 78.2 78.2 78.2 78.4 208.9 217.8 214.9 217.3 214.6
C4 39.9 47.2 47.3 40.1 38.8 39.3 36.7 36.8 47.3 38.6 38.7 38.5 38.9 46.2 45.3 47.1 46.7 47.2
C5 50.5 50.3 49.1 49.6 49.9 50.7 45.3 45.3 51.3 49.3 49.3 49.2 49.2 49.1 49.4 50.2 50.7 50.4
C6 28.4 37.1 37.2 37.2 36.5 18.5 18.0 18.0 19.6 26.0 26.1 26.0 26.7 36.8 27.7 37.0 28.2 37.1
C7 67.7 198.2 198.1 198.7 198.8 26.6 26.0 26.0 26.5 67.1 67.1 66.6 66.9 203.5 66.3 198.2 66.8 198.0
C8 157.3 139.5 139.6 138.9 138.8 134.1 134.0 133.8 135.0 158.0 158.1 158.3 156.6 151.1 157.6 139.4 136.7 139.5
C9 144.2 162.8 162.8 164.9 164.6 134.1 134.6 134.6 133.9 142.2 142.1 142.6 142.3 152.6 141.0 163.0 139.6 162.6
C10 39.8 39.4 39.5 39.5 39.7 37.2 36.9 36.9 37.1 39.1 39.2 38.7 38.7 38.9 38.3 39.3 38.0 39.4
C11 199.4 23.8 23.9 23.8 23.7 21.0 21.0 20.8 21.4 197.4 197.3 192.2 197.8 200.9 197.6 23.8 21.1 23.8
C12 78.7 30.1 30.2 30.5 30.2 30.6 30.8 30.8 29.0 44.3 44.4 75.8 50.7 78.5 50.5 30.0 31.0 30.1
C13 53.3 44.9 45.0 45.2 45.0 44.7 44.3 44.3 45.0 51.4 51.4 54.0 45.7 54.4 46.8 44.8 45.1 44.9
C14 62.7 47.4 47.8 48.2 47.8 49.6 49.9 49.6 49.9 58.3 58.3 59.4 59.7 55.0 59.7 47.7 49.7 47.8
C15 217.4 28.6 28.7 28.3 32.0 27.3 27.5 27.0 31.0 210.9 210.8 209.9 217.7 72.1 216.8 31.8 30.0 31.9
C16 38.6 31.8 31.9 32.7 28.7 29.2 29.7 29.0 27.3 122.4 122.3 122.5 36.1 33.3 36.3 28.6 29.9 28.7
C17 53.9 49.0 50.5 50.6 49.0 47.5 40.6 47.2 47.6 187.6 187.6 187.1 49.3 55.3 49.0 48.8 45.1 49.0
C18 13.8 15.9 16.0 16.1 15.9 16.1 16.1 16.0 16.5 30.9 30.9 26.3 19.0 13.1 19.3 15.8 16.2 15.9
C19 19.5 24.9 17.9 18.3 18.4 19.2 19.0 18.9 18.6 18.5 18.5 18.4 18.4 17.3 18.1 17.8 17.2 17.9
C20 73.8 36.6 36.6 37.3 36.7 48.9 44.9 47.5 48.5 28.6 28.6 29.1 73.0 72.9 72.9 36.0 36.4 36.2
C21 28.3 18.9 18.9 19.3 19.0 178.4 70.2 182.0 175.8 19.4 19.4 18.5 26.7 26.4 26.7 18.5 18.5 18.7
C22 52.3 33.4 33.6 34.5 33.5 33.0 30.7 32.5 33.4 47.6 47.6 47.4 52.7 51.2 52.7 36.0 32.8 32.6
C23 211.5 28.6 28.8 29.1 28.6 26.1 24.7 25.9 26.4 205.8 205.9 206.1 210.4 208.9 210.4 24.2 25.3 25.0
C24 49.4 79.5 79.1 77.1 79.6 124.0 124.8 123.6 124.7 46.1 46.3 46.0 47.7 48.3 47.7 131.4 60.6 60.3
C25 36.2 73.2 73.9 74.8 73.2 136.7 131.4 132.2 131.9 34.4 34.6 34.2 34.5 35.0 34.5 136.7 60.7 60.7
C26 180.2 23.2 67.7 69.3 23.3 67.8 17.7 17.6 25.8 179.9 176.0 180.3 175.9 176.3 175.9 67.4 65.4 65.5
C27 17.8 26.5 20.9 20.1 26.6 13.7 25.7 25.7 17.8 16.9 17.1 16.7 17.0 17.2 17.0 59.8 14.2 14.2
C28 28.9 25.3 25.4 27.9 25.0 -- 27.6 27.6 26.4 28.2 28.2 28.0 -- 27.9 27.0 25.2 26.5 25.4
C29 16.4 21.4 21.4 16.0 27.5 -- 21.8 21.8 21.3 15.5 15.5 15.3 -- 19.6 20.8 21.3 21.3 21.4
C30 23.3 17.9 25.0 25.2 15.3 28.4 24.4 24.3 24.4 33.2 33.2 33.0 28.2 20.7 25.1 24.8 26.1 24.9
C31 C1' Glc C31 C31 C31 CO- CO-
16.2 102.7 C1' 51.9 170.7 15.5 OCH3 OCH3
C32 C2' 95.8 C32 C32 51.4 52.0
24.3 71.9 20.7 24.8
NO. 136b) 137b) 138b) 139b) 140 141 142c) 143b) 144b) 145b) 148a) 149e) 150b) 151g) 152b) 153c) 155b)
C1 34.7 34.8 34.7 34.7 35.9 35.6 37.2 36.3 37.2 39.2 34.1 31.1 35.2 30.5 33.7 30.5 35.9
C2 24.2 24.1 24.2 24.2 33.6 27.6 35.2 34.0 34.5 18.2 28.5 23.6 24.1 24.6 27.4 23.0 33.8
C3 80.2 79.3 80.2 80.2 216.4 78.2 217.5 214.2 214.5 41.3 78.3 77.8 80.8 78.8 77.6 78.2 215.3
C4 37.8 37.9 37.7 37.8 46.0 41.6 49.0 47.8 47.4 38.3 39.4 37.0 37.8 38.1 40.5 36.5 47.7
C5 49.2 49.9 49.5 49.2 40.5 39.1 53.6 52.8 50.9 59.5 52.4 45.8 50.3 46.9 50.8 45.1 54.4
C6 26.7 37.0 26.7 26.7 23.1 22.2 40.9 40.0 33.4 22.3 19.1 18.3 26.3 19.4 36.2 17.7 40.3
C7 66.9 202.8 66.9 66.9 62.4 62.6 215.6 212.8 198.2 32.4 22.5 26.4 18.0 27.3 199.3 25.8 204.8
C8 157.0 154.7 157.0 157.0 63.6 62.8 55.0 54.0 150.0 42.8 51.2 134.7 132.9 135.6 146.8 133.9 46.2
C9 142.8 149.9 142.8 142.8 167.7 158.2 60.4 59.5 149.5 53.1 44.9 134.9 135.4 136.3 151.4 134.3 59.1
C10 38.9 40.1 38.9 38.9 40.5 37.9 38.0 36.5 39.2 37.5 35.7 37.2 37.0 38.4 39.1 36.6 37.5
C11 197.9 199.5 197.9 197.5 130.0 128.7 210.1 207.6 197.0 22.3 27.1 21.0 20.8 22.2 199.8 21.0 207.7
C12 50.4 52.3 50.4 50.4 203.6 78.1 53.7 52.6 192.6 41.5 49.0 29.6 31.1 30.8 49.9 28.6 50.6
C13 45.6 48.1 45.6 45.6 50.2 50.2 51.0 50.0 59.0 42.1 145.2 46.2 44.7 45.8 44.9 45.6 46.2
C14 59.6 53.0 59.6 59.6 64.8 64.4 51.3 49.7 61.0 59.5 47.9 48.8 51.0 51.0 57.2 49.3 54.7
C15 217.6 72.3 217.6 217.6 78.4 204.0 75.5 74.1 203.8 35.6 33.8 43.6 76.0 28.3 207.7 42.1 210.4
C16 41.1 36.5 41.1 41.1 127.2 127.2 39.0 38.4 38.9 30.5 31.3 76.6 36.5 28.7 35.0 76.6 40.2
C17 45.7 48.3 45.8 45.7 167.7 168.9 49.0 47.7 38.3 53.1 137.3 57.3 49.0 48.6 47.8 56.1 44.5
C18 17.6 17.5 17.6 17.6 30.9 31.0 17.1 16.6 12.4 14.6 179.2 17.8 16.1 17.0 17.8 17.0 15.8
C19 18.7 18.0 18.7 18.7 24.7 25.7 13.7 13.1 18.5 18.6 19.7 19.0 19.1 20.0 17.8 21.4 13.0
C20 32.2 32.6 32.2 32.2 72.2 72.2 33.5 32.0 32.2 36.0 35.4 48.7 36.2 49.0 73.9 47.9 32.1
C21 19.9 19.6 19.9 19.9 28.6 28.7 20.0 19.4 23.3 17.9 18.6 178.8 18.2 178.1 26.5 179.7 19.4
C22 49.5 49.5 49.5 49.5 53.9 53.9 50.5 49.6 48.6 35.3 35.1 31.6 34.6 34.3 42.1 32.0 49.1
C23 207.8 208.5 207.8 207.8 208.0 208.7 211.2 208.3 207.3 22.3 23.2 33.2 25.9 32.2(24R) 23.4 24.9 207.7
C24 46.8 46.8 46.9 46.8 48.0 48.2 47.8 46.8 46.5 58.2 125.6 156.1 145.2 76.5(24R) 143.6 33.6 47.1
C25 34.6 34.8 35.0 34.6 34.1 34.5 36.1 34.6 33.6 213.2 131.5 34.1 126.7 150.0(24R) 127.6 155.1 34.5
C26 179.9 179.3 175.8 179.9 180.1 179.6 179.6 176.2 180.3 32.1 25.8 21.9 172.6 110.8(24R) 173.0 106.4 176.2
C27 17.1 17.1 17.4 17.1 16.8 16.9 17.8 17.1 16.8 31.8 17.7 21.9 12.0 18.7(24R) 12.1 18.6 16.7
C28 28.3 17.3 28.3 28.3 24.0 24.6 25.9 25.2 -- 20.3 26.7 27.8 18.2 28.7 27.9 27.3 25.4
C29 16.7 20.3 16.7 16.7 21.7 22.2 21.9 21.2 -- 35.0 16.4 22.0 27.9 22.9 15.5 21.5 20.7
C30 24.5 28.3 24.6 24.5 26.9 27.0 12.8 12.5 27.4 28.7 25.7 16.5 25.3 22.4 24.8 12.7
CO CO OCH3 C31 C31 CH3CO COCH3
171.1 170.9 51.9 20.3 107.0 171.1 171.3
CH3 CH3 C32 CH3CO CH3CO COCH3
21.5 21.4 19.3 21.1 171.1 21.8
NO. 156b) 157d) 158d) 160b) 161d) 162b) 163b) 164 165 166 167 168b) 170b) 171 172b) 173b) 174b) 175b)
C1 36.6 29.8 29.7 36.6 35.8 30.9 30.7 36.6 35.8 35.4 35.3 36.4 30.6 36.9 30.8 29.8 30.5 36.6
C2 34.8 25.7 25.6 34.9 34.8 23.2 23.2 34.8 28.2 28.1 24.1 34.7 23.1 35.0 23.3 25.5 23.0 34.8
C3 216.6 73.8 73.8 216.9 216.6 78.1 78.1 217.0 79.0 80.8 80.6 216.4 78.1 215.2 78.2 76.0 78.0 216.9
C4 47.4 37.2 37.0 47.5 47.3 36.6 36.6 47.4 38.7 38.0 37.4 47.4 36.5 47.5 36.8 37.1 36.4 47.5
C5 50.5 42.8 42.8 50.7 50.4 44.0 44.1 50.7 50.4 50.3 48.8 50.6 44.0 51.0 44.1 43.1 44.0 50.7
C6 23.6 22.6 22.6 23.7 23.6 22.9 22.8 23.6 23.1 24.3 22.7 23.6 22.8 23.9 22.7 27.5 27.5 23.7
C7 121.2 120.6 120.6 119.9 121.0 121.2 121.3 119.8 120.3 120.0 120.9 121.7 121.6 121.6 121.6 120.3 120.2 120.3
C8 141.0 142.0 141.9 142.9 141.0 140.3 140.8 142.8 142.7 142.6 140.0 139.9 140.5 142.1 140.2 142.2 142.2 142.5
C9 144.8 146.0 145.9 144.5 144.7 145.9 146.2 144.5 145.9 145.6 145.5 145.0 146.2 145.4 146.2 145.9 145.8 144.6
C10 37.3 37.1 37.1 37.2 37.2 37.4 37.4 37.2 37.4 37.2 37.2 37.4 37.3 37.6 37.5 37.3 37.1 37.2
C11 116.9 115.1 115.1 117.3 117.0 115.7 115.7 117.2 116.3 116.5 116.0 116.8 115.3 117.3 115.5 115.5 115.5 116.9
C12 38.5 35.3 35.3 37.8 38.5 38.0 38.5 37.8 37.9 37.8 37.9 36.6 38.4 38.9 38.1 37.6 37.6 37.8
C13 44.4 43.9 43.9 43.8 44.3 44.2 44.5 43.7 43.8 43.8 43.9 44.3 44.3 44.6 44.1 43.6 43.6 43.7
C14 52.0 48.5 48.4 50.3 51.9 51.5 52.1 50.3 49.2 49.3 51.2 42.9 52.1 52.6 51.6 50.3 50.3 50.3
C15 74.6 43.4 43.3 31.5 74.6 77.5 74.7 27.9 28.0 27.9 77.2 47.0 74.5 73.7 77.4 31.2 31.3 31.4
C16 40.0 75.1 75.0 27.9 40.1 37.0 40.1 31.4 31.5 31.5 36.8 219.2 39.6 40.5 36.7 22.9 22.8 27.6
C17 48.9 56.2 56.2 50.8 48.8 48.9 48.9 50.9 50.9 50.8 48.7 60.5 45.5 49.4 45.6 47.3 47.3 47.4
C18 16.0 16.9 16.9 15.7 15.9 16.0 16.0 15.7 15.7 15.7 15.8 16.8 15.8 16.5 15.9 15.4 15.4 15.5
C19 22.2 22.7 22.7 22.1 22.1 22.7 22.5 22.4 22.8 22.9 22.7 22.1 22.7 22.2 23.0 22.7 22.4 21.1
C20 35.9 46.9 46.9 36.2 35.8 36.0 36.0 36.0 36.1 36.1 35.8 31.5 39.3 36.3 39.8 39.3 39.3 39.4
C21 18.3 177.2 177.2 18.3 18.3 18.5 18.3 18.4 18.4 18.4 18.0 18.6 12.8 18.7 12.8 12.6 12.6 12.7
C22 34.7 31.9 31.7 35.8 36.6 34.7 34.8 35.9 36.0 35.8 34.5 35.7 74.7 30.0 74.6 74.6 74.6 74.7
C23 25.8 26.0 25.4 26.9 25.4 26.0 25.9 24.5 24.6 24.8 25.8 24.8 31.7 24.7 32.1 31.7 31.8 31.9
C24 145.1 124.3 123.1 147.1 126.6 144.9 145.2 126.9 127.0 128.6 144.9 131.2 139.1 127.6 139.2 139.5 139.6 139.5
C25 126.8 131.2 135.7 125.7 134.6 126.8 126.8 134.3 134.3 137.4 126.7 137.3 129.4 140.8 129.4 129.0 129.0 129.1
C26 172.2 25.7 66.5 172.1 69.0 172.0 172.1 69.0 69.1 66.8 173.0 67.7 172.2 65.5 172.0 172.2 172.3 171.9
C27 12.0 17.7 13.6 20.6 13.5 12.1 12.1 13.6 13.7 59.8 11.8 60.5 12.3 58.6 12.4 12.2 12.2 12.3
C28 17.0 28.7 28.7 25.4 16.9 27.8 27.8 25.3 25.6 25.6 18.2 22.4 27.8 25.7 -- -- -- 25.3
C29 25.4 22.8 22.8 25.3 25.4 22.5 22.7 25.4 27.8 28.2 28.0 25.3 22.5 22.4 -- -- -- 22.5
C30 22.5 26.2 26.1 22.5 22.1 18.2 17.2 22.0 15.8 17.0 16.8 25.7 17.3 18.0 27.9 28.1 27.7 25.5
COCH3 COCH3 AcCH3 COCH3 C31 C31 C31 22-O-COCH3
171.2 170.8 21.1 170.8 22.6 22.5 22.5 170.7
COCH3 COCH3 AcCH3 COCH3 C32 C32 C32 22-O-COCH3
21.4 21.3 21.2 21.3 18.6 25.7 25.6 21.1
NO. 176b) 177b) 178b) 179b) 180b) 181b) 182b) 183b) 184b) 185b) 186b) 187a) 188a) 189b) 190b) 191b) 192b) 193b)
C1 35.4 29.9 30.5 30.6 30.5 35.6 35.3 36.6 36.6 29.9 30.6 36.8 36.8 35.6 36.1 35.8 35.4 30.5
C2 24.2 25.5 23.0 23.1 23.1 27.6 24.1 37.5 34.8 25.5 23.1 35.0 29.2 27.8 34.9 36.5 36.5 23.1
C3 80.7 76.7 78.0 78.1 78.0 78.8 80.7 216.6 216.4 76.1 78.1 215.3 78.4 78.8 216.8 216.5 216.5 78.0
C4 37.6 37.3 36.4 36.5 36.4 38.5 37.4 47.4 47.4 37.0 36.5 47.5 39.8 38.6 47.5 47.6 47.6 36.4
C5 48.9 42.9 43.8 44.0 43.9 48.7 48.9 50.4 50.4 42.9 45.0 50.9 50.1 49.0 50.8 60.7 60.8 44.2
C6 22.8 23.0 22.7 22.8 22.7 22.9 22.6 23.6 23.7 23.0 22.8 23.8 23.9 22.9 23.7 23.8 23.8 22.7
C7 121.3 121.5 121.3 121.4 121.2 121.3 121.0 121.0 121.3 121.5 121.6 121.6 122.5 120.3 120.0 121.8 121.8 121.5
C8 140.0 140.0 140.0 140.6 140.6 140.0 140.6 140.4 140.2 140.0 140.5 142.0 142.4 142.4 142.9 140.1 140.2 140.4
C9 145.8 146.0 145.8 146.1 146.1 145.8 145.7 145.0 144.7 146.0 146.2 145.3 147.4 145.9 144.6 145.1 145.1 146.1
C10 37.3 37.3 37.3 37.3 37.2 37.3 37.2 37.3 37.3 37.3 37.3 37.5 38.3 37.3 37.3 37.6 37.6 37.2
C11 115.9 115.5 115.4 115.5 115.4 115.8 116.0 116.9 116.7 115.3 115.3 117.2 116.6 116.0 117.3 117.0 117.0 115.2
C12 38.0 37.9 37.8 38.3 38.3 37.9 38.3 38.0 38.0 37.9 38.4 38.8 39.2 37.7 37.9 36.8 36.8 38.4
C13 43.9 44.1 44.1 44.5 44.3 44.0 44.2 44.1 43.9 43.9 44.2 44.5 45.0 43.7 43.8 44.5 44.5 43.9
C14 51.3 51.7 51.4 52.2 52.0 51.2 51.8 51.3 51.4 51.4 52.0 52.6 53.0 50.2 50.4 43.1 43.1 52.0
C15 77.0 77.0 77.2 74.6 74.5 77.3 74.5 77.2 76.7 76.9 74.5 73.6 74.2 31.4 27.9 34.9 34.9 74.4
C16 36.6 37.2 37.1 40.1 40.2 36.9 39.8 37.0 36.6 36.7 39.8 40.9 41.0 27.7 31.5 25.0 25.3 39.6
C17 45.4 48.7 48.6 48.8 49.2 48.7 48.7 48.9 45.5 45.4 45.0 50.1 49.8 50.7 50.9 31.6 31.7 45.4
C18 15.7 16.0 15.9 16.0 15.7 15.9 15.8 16.0 15.8 15.8 15.8 16.3 16.8 15.7 15.8 17.0 17.1 15.7
C19 22.8 22.6 22.5 22.7 22.5 22.7 22.7 22.4 22.1 22.7 22.6 22.1 23.6 22.6 22.5 22.3 22.3 22.6
C20 39.6 32.8 32.8 33.0 33.4 35.8 35.8 35.9 39.6 39.6 39.3 34.4 36.8 36.0 36.1 50.8 50.8 39.2
C21 12.6 19.4 19.3 19.6 19.4 18.1 18.1 18.2 12.7 12.7 12.8 20.3 19.0 18.2 18.4 18.7 18.8 12.7
C22 74.4 51.5 51.5 51.9 67.0 34.5 34.7 34.6 74.4 74.4 74.6 44.7 37.3 34.6 36.7 219.3 219.0 74.5
C23 31.9 201.6 201.4 201.8 43.6 25.8 25.7 25.9 31.9 31.9 31.7 67.1 25.1 25.9 24.4 47.1 47.1 31.7
C24 139.0 133.8 133.9 134.1 144.8 144.9 145.0 144.5 139.0 139.1 139.2 145.5 127.9 155.4 131.7 131.4 126.8 139.2
C25 129.2 139.5 139.4 139.3 128.3 126.7 126.8 126.8 129.2 129.2 129.4 128.7 141.3 139.1 136.8 137.4 134.8 129.2
C26 171.3 171.2 171.8 171.0 172.0 172.9 172.9 172.1 171.3 171.6 172.0 170.3 65.8 195.3 67.7 60.2 69.3 172.1
C27 12.3 14.1 13.9 14.1 12.6 11.9 11.9 12.0 12.3 12.3 12.3 13.5 58.8 9.0 60.2 67.9 13.8 12.2
C28 18.4 18.5 18.3 17.2 17.1 18.3 17.0 18.2 25.4 -- -- 25.6 29.3 25.4 25.5 25.5 25.5 17.2
C29 28.1 28.2 27.7 27.8 27.7 28.1 28.0 25.4 22.4 -- -- 22.3 17.1 28.0 22.1 22.6 22.6 27.6
C30 16.9 22.6 22.3 22.5 22.3 15.7 16.8 22.1 18.3 28.2 27.7 18.0 18.6 15.5 25.4 25.8 25.8 22.4
AcCO AcCO AcCO AcCO AcCO AcCO AcCO AcCO 15-O- C31 C31 C1'
171.1 171.0 171.1 170.9 170.7 171.1 170.9 171.2 COCH3 22.8 22.5 170.8
AcCO AcCH3 AcCO AcCH3 AcCH3 AcCO AcCO AcCO 171.1 C32 C32 C2'
170.6 21.4 170.7 21.3 21.2 21.3 21.2 21.4 18.5 17.3 170.5
AcCH3 AcCH3 C3'
21.0 21.6 21.2
NO. 194b) 196d) 197b) 198b) 201b) 202b) 203 204b) 205b) 207b) 208b) 209 210b) 214b) 215b) 216b) 217b) 218b)
C1 35.6 36.1 35.7 35.4 35.7 36.6 36.6 36.5 29.9 30.0 35.5 30.5 36.7 29.8 35.6 30.6 35.4 29.9
C2 27.7 34.4 28.0 22.8 27.9 34.8 28.7 34.9 25.6 25.6 27.0 23.0 34.8 25.4 27.4 23.1 24.2 25.6
C3 78.8 215.3 78.9 80.8 78.9 216.7 78.1 216.9 76.1 76.3 78.3 78.0 217.0 75.8 78.6 78.0 80.7 76.1
C4 38.6 46.9 38.7 37.6 38.7 47.4 39.4 47.5 37.3 37.3 38.3 36.4 47.5 37.2 38.5 36.5 37.6 37.4
C5 48.7 50.5 49.1 49.3 49.1 50.7 49.8 50.3 42.9 43.1 48.5 43.8 50.3 42.9 49.0 43.9 49.0 43.0
C6 22.9 23.2 23.0 24.3 23.0 23.6 23.5 23.7 23.0 23.0 22.6 22.7 23.6 22.8 22.8 22.8 22.9 22.9
C7 121.6 120.1 120.4 120.0 120.2 119.9 121.0 119.9 121.3 121.4 121.0 121.0 119.9 121.2 121.2 121.2 121.2 121.7
C8 139.9 142.1 142.5 142.7 142.6 142.8 143.0 142.8 140.2 140.9 140.5 140.1 142.8 140.6 140.7 140.1 140.2 140.5
C9 146.0 144.2 146.0 146.7 145.9 144.5 146.6 144.5 146.0 146.3 145.9 145.4 144.4 146.1 146.0 145.9 145.7 146.3
C10 37.4 37.0 37.4 37.8 37.3 37.2 37.8 37.8 37.3 37.3 37.1 37.2 37.8 37.2 37.3 37.3 37.3 37.4
C11 115.5 116.7 116.1 116.5 116.2 117.2 116.6 117.2 115.6 115.7 115.5 115.5 117.2 115.4 115.8 115.5 116.1 115.3
C12 37.9 35.3 37.8 37.2 37.8 37.8 38.1 37.2 38.0 38.5 38.2 37.9 37.2 38.3 38.4 37.9 38.0 38.5
C13 43.9 43.8 43.8 43.7 43.7 43.7 44.1 43.8 44.1 44.4 44.0 44.0 43.7 44.2 44.1 44.1 44.1 44.2
C14 51.3 48.3 50.3 50.3 50.3 50.3 50.7 50.7 51.4 52.2 51.6 51.3 50.7 51.9 51.9 51.4 51.4 52.1
C15 76.9 43.3 31.5 26.0 31.5 27.6 28.1 27.9 77.4 74.8 73.9 77.3 27.9 74.2 74.3 77.3 77.1 74.6
C16 36.6 75.0 27.8 31.5 27.8 28.8 31.9 28.7 37.0 40.0 39.2 36.9 28.8 39.8 38.7 37.2 37.2 39.8
C17 45.4 56.2 50.9 50.8 50.9 51.0 51.5 50.9 48.9 48.8 48.7 48.8 51.0 49.2 45.0 49.4 49.4 45.4
C18 15.7 16.9 15.7 16.9 15.7 15.7 16.6 15.7 16.0 15.9 15.5 15.9 15.3 15.7 15.7 15.9 15.9 15.8
C19 22.7 21.8 22.7 22.8 22.7 22.4 23.1 22.5 22.7 22.7 22.4 22.5 22.4 22.6 22.7 22.6 22.9 22.7
C20 39.5 46.9 36.2 36.5 36.5 36.5 37.1 36.6 36.0 35.9 35.6 35.9 36.6 33.3 40.7 33.6 33.6 39.3
C21 12.6 177.2 18.3 18.6 18.6 18.6 19.0 18.6 18.2 18.3 17.9 18.1 18.6 19.3 12.4 19.3 19.3 12.8
C22 74.4 31.8 34.7 32.6 33.5 31.4 34.4 31.5 34.7 34.8 34.5 34.5 31.5 66.5 72.1 67.2 67.2 74.6
C23 31.8 26.0 26.1 27.8 28.7 33.5 28.9 33.5 25.9 25.7 25.4 25.8 33.5 43.4 34.8 43.3 43.4 31.7
C24 138.9 124.2 155.4 76.6 79.6 79.2 77.2 79.6 145.1 145.2 143.3 145.0 79.1 143.6 139.9 144.7 144.7 139.2
C25 129.2 131.1 139.1 73.3 73.2 73.9 74.8 73.3 126.6 127.0 127.0 126.7 74.1 128.6 129.0 128.1 128.1 129.1
C26 171.5 25.6 195.4 68.5 23.6 67.6 69.3 25.5 171.9 172.8 170.5 172.9 67.6 170.3 170.4 171.2 171.2 171.0
C27 12.2 17.6 9.2 20.2 26.5 22.0 20.1 25.3 12.0 12.0 11.7 11.8 22.0 12.7 11.4 12.8 12.8 12.3
C28 18.3 25.4 28.1 28.1 28.1 -- 28.8 23.2 18.5 17.4 16.8 18.3 25.4 17.0 17.1 18.4 18.4 17.3
C29 28.1 22.1 15.8 15.7 15.8 -- 16.0 26.6 28.2 28.2 27.7 27.7 25.4 28.0 28.0 27.8 28.1 28.1
C30 15.7 25.8 25.6 25.5 25.6 25.3 25.9 22.1 22.8 22.8 15.4 22.3 20.9 22.7 15.7 22.4 16.9 22.8
C1' OCOCH3 C31 C31 AcCH3 CH3CO CH3CO CH3CO
171.0 170.64 20.9 171.2 21.2 170.8 170.5 170.6
C2' 170.93 C32 C32 AcCH3 CH3CO CH3CO CH3CO
170.5 171.11 25.4 21.4 21.3 170.6 171.0 21.03
C3' OCOCH3 AcCO CH3CO CH3CO
21.3 20.83 170.7 21.4 21.3
C4' 20.99 AcCO CH3CO CH3CO
20.9 21.29 171.0 21.3 21.4
NO. 219b) 220b) 221b) 222b) 223b) 224b) 225b) 226b) 227b) 228b) 229b) 230b) 231b) 232b) 233b) 234b) 238b) 239b)
C1 35.6 36.6 35.7 35.0 35.8 34.7 35.8 37.4 35.7 36.0 34.8 37.4 36.7 37.3 35.6 34.2 35.3 34.4
C2 27.3 34.8 27.8 27.9 34.5 27.5 34.1 34.0 34.3 34.5 27.6 34.0 27.4 34.6 34.2 23.9 34.3 27.2
C3 78.6 216.8 78.9 78.5 216.8 78.3 216.6 214.8 216.5 215.9 78.3 215.2 77.5 215.3 218.1 79.9 214.7 78.0
C4 38.5 47.5 38.7 38.8 47.0 38.6 46.7 46.9 46.8 46.8 38.6 46.9 40.5 43.9 46.7 37.5 47.2 38.5
C5 48.9 50.7 49.1 49.3 49.1 49.1 48.8 51.0 49.0 48.9 49.1 50.9 51.4 51.0 48.7 49.2 50.4 49.1
C6 22.8 23.7 23.0 26.8 27.8 26.5 27.6 33.8 27.7 29.1 26.6 33.7 33.3 33.9 27.6 26.6 37.1 26.6
C7 121.6 120.0 120.3 67.0 66.5 66.9 66.2 198.5 66.3 65.7 66.9 198.7 198.8 199.5 66.2 66.1 198.1 66.1
C8 140.4 142.8 142.6 157.2 158.1 156.8 157.4 149.7 157.8 159.8 156.8 149.8 151.6 149.7 157.9 157.4 139.5 155.9
C9 146.2 144.5 146.0 142.9 141.4 142.6 141.1 146.2 141.3 140.9 142.7 146.2 146.0 146.9 141.1 141.6 162.7 142.9
C10 37.3 37.2 37.4 38.8 38.4 38.8 38.2 39.3 38.3 38.5 38.8 39.3 39.2 39.4 38.2 37.5 39.4 38.5
C11 115.4 117.2 116.2 198.2 197.9 197.8 196.9 194.1 197.5 198.0 198.0 194.1 194.1 199.4 197.8 199.5 23.8 192.3
C12 38.3 37.8 37.8 50.6 50.4 49.1 49.9 79.1 49.1 49.8 50.3 79.1 79.4 49.0 50.2 78.2 30.1 79.8
C13 44.0 43.8 43.8 45.5 45.1 46.0 45.0 47.6 45.3 45.5 45.3 47.6 48.0 47.0 44.9 51.9 44.9 50.4
C14 51.8 50.3 50.3 59.6 59.5 58.8 59.2 58.6 58.8 58.3 59.4 58.6 58.5 57.2 59.3 60.2 47.8 60.6
C15 74.0 31.5 31.5 218.1 218.2 217.7 215.8 205.8 217.7 215.5 217.5 205.9 206.0 207.3 216.8 217.1 28.5 216.7
C16 39.1 27.9 27.9 41.2 41.3 38.4 35.6 37.4 38.7 39.5 41.0 37.6 37.6 39.9 41.1 38.0 31.8 37.4
C17 45.3 50.9 50.9 46.4 46.5 46.1 49.5 45.2 46.3 46.7 46.1 45.2 45.5 45.2 46.2 46.5 48.9 46.0
C18 15.6 15.7 15.7 17.6 17.9 18.4 19.0 12.0 18.8 19.3 17.4 12.0 12.1 16.1 17.6 12.0 15.9 13.1
C19 22.7 22.5 22.7 18.6 18.3 18.5 18.1 18.6 18.2 18.6 18.4 18.7 18.0 18.6 18.2 18.8 17.9 18.6
C20 39.1 36.1 36.0 35.4 35.4 143.9 85.9 33.0 143.9 145.8 35.1 33.1 33.0 35.4 35.2 31.7 35.9 31.8
C21 12.5 18.4 18.4 18.3 18.2 112.2 25.9 20.1 112.3 111.6 18.0 20.0 20.2 18.3 18.0 20.5 18.3 20.4
C22 74.9 32.7 32.7 30.8 30.9 31.3 34.2 30.1 31.3 31.8 30.4 29.9 30.2 30.8 30.6 29.4 30.8 29.5
C23 31.5 25.3 25.3 31.3 31.3 32.3 27.4 31.6 31.9 32.6 30.7 31.6 31.8 31.0 31.1 31.5 30.9 30.0
C24 137.2 60.6 60.6 173.8 173.8 177.3 175 173.6 175.1 173.2 178.2 178.7 173.7 173.8 173.5 177.8 178.1 178.2
C25 129.9 60.7 60.7 -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
C26 169.9 65.4 65.4 -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
C27 12.3 14.2 14.2 -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
C28 17.1 25.4 28.1 28.4 27.2 24.2 25.0 -- 27.0 27.0 24.4 -- -- -- -- 27.9 25.3 28.0
C29 27.9 22.1 15.8 15.6 20.9 28.1 26.9 -- 20.8 20.9 28.1 -- -- -- -- 16.4 21.4 15.3
C30 15.6 25.4 25.6 24.6 24.9 15.4 20.7 27.6 24.6 25.2 15.4 27.6 27.9 27.7 27.0 23.1 24.9 24.0
CH3CO Bu1' Bu1' C31 COOCH3 C31 C31 C31 C31 C31 COCH3
171.1 64.6 64.6 20.8 51.5 20.4 15.6 20.9 20.7 161.0 170.5
CH3CO Bu2' Bu2' C32 C32 C32 C32 C32 COCH3
20.87 30.9 30.9 20.4 20.8 21.4 20.3 24.6 20.7
NO. 241b) 242b) 243b) 244b) 248b) 249b) 252b) 253b) 254b) 255b) 256b) 261b) 262a) 263a) 264a) 266a) 267b) 268a)
C1 35.6 33.6 34.0 33.3 35.0 35.4 34.0 34.6 33.2 34.8 34.4 36.6 36.8 35.4 36.7 35.3 35.4 73.8
C2 34.3 27.4 33.8 27.4 27.9 34.5 33.6 33.8 27.3 27.6 27.4 34.8 35.0 28.3 27.9 28.9 27.7 39.8
C3 216.9 77.6 214.8 77.5 78.5 215.9 214.9 215.1 77.4 78.2 78.1 216.5 215.3 72.0 70.7 79.3 78.8 75.5
C4 46.8 39.1 46.9 40.5 38.8 47.2 46.9 47.0 40.5 38.6 38.6 47.4 47.4 43.0 43.6 43.1 38.8 40.2
C5 48.8 50.8 51.0 51.4 49.3 49.6 50.9 50.9 51.4 49.1 49.1 50.7 50.9 42.5 44.5 50.2 50.2 49.1
C6 29.0 36.3 37.4 36.7 26.9 28.0 37.4 37.2 36.6 26.6 26.7 23.7 23.8 27.8 34.1 28.5 18.2 17.6
C7 68.8 199.4 198.5 198.8 67.0 66.0 198.4 199.1 198.0 66.0 66.1 119.9 121.6 66.7 200.4 67.0 26.4 26.0
C8 159.2 151.6 149.7 151.6 157.2 158.6 145.6 146.2 151.4 156.5 155.9 142.6 142.0 158.8 152.2 158.0 134.1 134.1
C9 140.3 147.0 146.2 156.0 142.9 140.6 149.6 149.6 145.4 142.6 142.9 144.4 145.3 142.9 147.4 142.6 134.4 137.0
C10 38.0 40.4 39.3 39.2 38.9 38.1 39.3 34.6 39.1 38.9 38.6 37.2 37.5 39.2 40.8 39.1 36.9 44.1
C11 199.6 199.9 194.1 194.1 198.1 199.9 193.3 198.0 193.0 197.0 191.0 117.0 117.2 198.3 199.8 198.4 20.9 25.1
C12 51.8 49.6 79.1 79.4 50.6 78.5 78.6 48.8 78.9 50.2 79.1 37.8 38.7 51.1 49.9 51.1 30.7 32.0
C13 46.6 44.3 47.6 48.0 45.5 51.9 47.9 44.3 48.2 45.4 49.8 43.7 44.5 45.6 44.5 45.6 44.4 44.3
C14 53.9 57.0 58.6 58.5 59.6 60.5 58.9 57.1 58.9 59.3 61.0 50.2 52.6 59.2 57.6 59.0 49.8 50.4
C15 72.6 208.1 205.8 206.0 218.1 217.5 203.8 204.9 203.9 215.7 214.5 27.9 73.6 216.8 208.0 216.7 30.7 31.6
C16 36.6 40.2 37.4 37.6 41.2 37.9 35.4 34.3 35.7 35.7 37.1 31.5 40.4 41.4 40.5 41.5 27.7 28.7
C17 48.5 45.6 45.2 45.5 46.4 46.8 48.8 48.1 49.2 49.5 50.2 50.8 49.3 46.2 45.5 46.3 45.7 46.6
C18 17.3 16.2 12.0 12.1 17.6 12.3 13.0 17.4 13.2 18.8 14.2 15.7 16.4 17.8 16.4 17.9 15.5 16.2
C19 19.4 17.8 18.6 18.0 18.6 18.5 18.7 18.6 17.9 18.3 18.5 22.0 22.1 19.2 18.6 19.2 19.1 15.5
C20 35.7 35.3 33.0 33.0 35.4 31.8 86.4 86.0 86.6 85.9 86.7 36.2 36.1 35.4 35.5 35.3 40.4 40.7
C21 18.1 18.2 20.1 20.2 18.2 20.7 26.1 26.3 26.1 25.9 25.2 18.3 18.4 18.1 18.2 18.0 13.3 13.8
C22 30.0 30.5 30.1 30.2 30.9 30.0 34.5 34.2 34.5 34.2 34.6 29.7 32.0 31.0 31.0 31.0 80.2 80.5
C23 31.0 30.8 31.6 31.8 31.1 32.4 28.0 27.3 28.1 27.5 28.3 30.1 31.9 31.0 31.1 30.9 27.7 28.7
C24 174.3 178.0 173.6 173.7 174.1 173.9 175.6 175.8 175.6 175.9 175.5 178.2 176.4 174.0 174.0 174.1 139.7 140.5
C25 -- 27.8 -- -- -- -- -- -- -- -- -- -- -- 66.6 65.1 -- 128.1 127.8
C26 -- 15.5 -- -- -- -- -- -- -- -- -- -- -- 13.2 13.1 -- 166.6 166.2
C27 -- 21.8 -- -- -- -- -- -- -- -- -- -- -- 24.8 21.6 -- 17.1 18.7
C28 27.4 -- -- -- 28.4 26.5 27.6 27.6 27.9 28.1 28.1 25.4 25.6 -- -- 23.7 27.9 28.2
C29 20.7 -- -- -- 15.6 21.4 20.4 20.3 15.5 15.4 15.4 22.4 22.3 -- -- 64.2 15.4 15.4
C30 19.4 -- 27.6 27.9 24.6 23.5 21.1 21.3 21.6 24.7 24.5 25.3 17.9 -- -- 24.9 24.3 24.9
CO- C31 C31 C1' C1' COCH3 COCH3 COCH3 CO- CO- CO-
OCH3 20.4 15.6 51.9 64.6 170.1 170.1 170.3 OCH3 OCH3 OCH3
51.6 C32 C32 C2' COCH3 COCH3 COCH3 51.4 51.4 51.4
20.8 21.4 30.9 21.0 21.0 21.2
NO. 269b) 270b) 271b) 272b) 273b) 274b) 275b) 276b) 277a) 278b) 279b) 280b) 281b) 282b) 286 287 288b) 289b)
C1 143.7 143.6 144.2 147.9 35.2 35.0 36.6 36.6 35.5 35.2 36.0 35.7 35.7 35.4 36.2 36.1 36.7 29.7
C2 118.0 118.1 118.5 116.7 34.3 28.3 34.8 34.8 29.3 34.3 33.6 27.7 35.4 27.5 33.7 33.6 34.9 22.8
C3 167.1 167.0 166.8 163.9 213.2 77.0 217.0 217.0 78.1 217.2 216.2 78.0 215.7 77.9 216.5 216.0 216.9 77.5
C4 80.5 80.5 80.6 77.5 47.0 38.6 47.5 47.5 40.1 44.8 45.9 41.5 46.0 41.8 46.0 45.9 47.5 36.4
C5 49.0 49.0 49.2 92.6 49.8 49.6 50.8 50.8 50.5 49.4 40.8 39.3 40.7 39.4 39.4 40.7 50.7 47.7
C6 38.7 38.4 37.3 44.1 27.9 27.9 23.6 23.6 27.2 27.2 23.2 21.8 22.9 21.8 23.2 22.7 23.7 20.4
C7 27.6 27.2 27.2 26.8 65.8 66.6 119.4 119.4 71.7 70.1 60.5 58.7 59.1 59.0 62.9 62.6 119.4 25.7
C8 147.6 147.0 149.3 149.5 157.8 156.8 142.8 142.7 158.3 158.3 66.0 71.4 62.1 62.9 64.3 57.6 142.7 137.6
C9 130.5 129.9 131.8 127.6 140.9 143.0 144.4 144.4 140.7 138.7 163.4 165.6 167.6 168.9 164.8 164.8 144.3 128.3
C10 139.1 139.3 140.1 132.9 37.8 39.2 37.2 37.1 39.3 37.5 40.2 37.9 40.8 38.0 40.3 40.7 37.2 39.4
C11 26.9 26.8 67.7 28.0 199.4 200.5 117.3 117.2 200.0 199.7 130.8 128.7 129.8 128.5 130.1 129.7 117.2 22.5
C12 31.4 31.1 42.5 31.1 78.1 79.0 37.7 37.7 53.3 52.1 201.2 200.9 199.8 200.2 202.8 200.5 37.7 31.0
C13 43.7 44.3 43.2 44.3 49.9 50.5 43.7 43.7 40.1 46.9 50.3 54.9 54.5 54.3 53.3 55.0 43.8 44.3
C14 56.4 54.9 55.6 55.1 63.3 63.0 50.3 50.2 53.7 52.9 59.3 62.0 62.8 61.5 60.2 58.8 50.3 50.4
C15 76.2 78.0 77.6 78.4 215.5 215.0 27.8 27.8 71.9 70.8 71.7 209.6 202.8 203.1 76.6 209.5 27.8 31.1
C16 40.6 38.6 38.5 38.4 60.4 60.6 31.5 31.4 33.3 32.5 33.6 38.5 125.2 125.2 39.5 38.3 31.5 27.6
C17 45.6 45.3 45.1 45.7 54.2 54.0 50.8 50.7 49.6 48.9 45.8 43.0 181.6 181.9 48.7 42.9 50.9 45.7
C18 17.3 16.7 18.9 16.8 12.8 13.3 15.7 15.7 18.1 17.6 18.1 18.1 30.3 29.8 19.6 18.1 15.8 15.7
C19 143.0 142.8 141.0 139.4 18.3 19.2 22.0 22.0 20.7 19.6 21.6 18.3 24.9 25.9 21.3 21.6 22.1 104.0
C20 40.0 39.9 39.9 39.8 33.0 33.3 36.4 36.5 33.6 32.7 157.3 154.9 73.0 72.9 158.6 158.6 36.5 40.4
C21 13.4 13.3 13.2 13.3 19.2 19.6 18.5 18.5 20.3 19.8 20.6 20.4 29.5 29.4 20.9 20.4 18.7 13.3
C22 80.0 79.8 79.6 79.7 52.5 52.3 33.1 33.1 50.6 49.9 126.0 126.7 52.9 52.9 126.3 126.8 33.5 80.1
C23 27.8 27.8 27.7 27.7 87.0 87.5 25.8 25.7 209.3 208.5 198.8 198.7 206.2 206.3 199.2 198.5 29.8 27.9
C24 139.6 139.4 139.4 139.3 40.6 40.4 78.8 76.8 47.8 46.9 47.6 47.7 47.8 47.8 47.6 47.6 77.2 139.0
C25 128.3 128.4 128.4 128.4 34.3 34.8 73.6 73.5 36.3 34.8 34.8 34.9 34.5 33.1 33.7 34.9 73.9 128.0
C26 166.4 166.3 166.2 166.2 178.6 179.0 66.5 68.7 178.6 176.4 179.6 179.7 179.9 179.9 180.1 180.2 69.6 166.5
C27 17.1 17.1 17.1 17.1 15.6 15.6 18.1 18.3 18.3 17.3 17.0 17.0 16.9 16.9 17.0 17.0 20.3 17.2
C28 29.0 28.8 28.1 24.9 -- -- 25.3 25.3 29.3 27.8 14.6 17.1 24.8 17.1 21.7 24.8 25.4 23.8
C29 26.3 26.4 26.7 24.8 -- -- 22.5 22.4 17.4 20.8 24.6 25.8 21.6 25.7 24.8 21.7 22.5 25.7
C30 26.6 26.4 25.4 24.4 25.8 28.5 25.4 25.4 20.2 19.8 28.7 28.7 28.7 28.7 28.6 28.6 25.5 23.2
C1' C1' C1' C31 C31 C1' C1' C1' COCH3 C1' OCH3
170.4 170.3 170.1 21.3 16.0 195.5 31.8 102.7 52.1 195.3 55.2
C2' C2' C2' C32 C32 C2' C2' C2' C(CH3)2 C2'
21.4 21.4 21.3 25.2 24.6 127.8 140.6 24.1 102.3 126.6
NO. 290b) 291b) 292b) 293a) 294b) 295b) 296b) 297e) 298b) 299a) 300a) 301a) 302b) 303b) 304b) 305b) 306b) 307b)
C1 27.5 143.8 34.1 35.5 35.7 31.2 28.7 31.3 32.6 57.0 57.0 57.0 30.4 31.0 28.8 28.8 29.7 35.2
C2 27.1 118.0 27.4 28.6 34.2 27.7 28.4 23.6 28.0 36.5 36.5 36.5 23.3 34.6 27.7 25.5 28.3 34.0
C3 177.3 167.0 76.5 77.6 216.4 78.7 179.0 78.3 78.9 216.5 216.5 216.4 78.1 216.6 175.6 174.5 175.5 214.9
C4 74.5 77.8 39.2 49.7 46.8 38.9 75.3 37.0 39.0 47.0 47.0 47.1 36.7 47.1 75.2 75.0 74.8 46.6
C5 55.1 48.9 50.3 49.7 48.9 50.2 47.9 46.0 50.1 55.4 55.4 55.5 45.3 39.7 47.9 48.0 47.8 49.3
C6 33.8 35.8 36.9 28.1 27.6 17.6 23.9 18.4 17.8 29.4 29.4 29.4 18.0 28.8 24.3 21.5 24.8 36.9
C7 27.1 27.1 203.8 66.7 66.2 25.7 26.7 26.3 26.2 68.3 68.4 68.3 25.9 66.2 24.3 117.9 26.0 204.5
C8 139.2 146.0 146.2 158.7 157.5 137.1 143.3 134.4 137.9 136.4 136.3 136.3 133.7 132.9 143.1 134.1 139.6 150.9
C9 121.7 147.0 155.9 142.7 141.2 131.7 126.1 135.1 130.4 154.7 154.7 154.8 134.7 76.3 126.1 141.1 126.1 153.2
C10 91.5 142.8 40.4 39.3 38.3 39.6 45.4 37.3 42.2 48.6 48.6 48.6 36.9 41.4 45.4 42.2 45.7 39.4
C11 33.0 26.3 198.5 198.0 196.8 23.0 20.8 21.2 22.0 83.5 83.6 83.5 20.8 26.2 22.6 120.4 22.5 200.9
C12 30.7 31.1 79.3 50.9 50.1 31.0 31.0 30.8 31.0 37.4 37.4 37.4 30.8 34.2 31.2 39.4 31.2 49.6
C13 44.5 44.3 54.1 45.8 45.1 44.4 44.3 45.0 44.4 45.6 45.6 45.7 44.3 45.2 51.4 43.7 44.1 48.2
C14 50.5 54.9 50.6 59.0 59.3 50.2 51.5 49.9 50.4 62.3 62.4 62.4 49.5 155.0 51.8 49.9 51.4 51.8
C15 30.1 77.8 80.1 215.0 215.8 30.7 31.3 27.5 30.7 215.0 215.3 214.8 27.0 77.5 30.5 31.5 30.8 72.9
C16 27.1 38.5 128.1 36.5 35.8 27.6 27.4 29.4 27.5 41.0 41.1 41.0 28.9 47.9 28.5 26.0 26.6 31.7
C17 45.5 44.8 157.7 49.7 49.0 45.8 45.9 47.7 47.1 46.8 46.9 46.6 47.0 49.7 46.9 47.5 47.8 39.2
C18 15.5 16.7 26.0 18.6 18.1 15.6 15.9 16.4 16.6 17.7 17.7 17.7 16.3 17.2 15.7 16.0 15.8 16.6
C19 41.5 142.8 20.8 19.4 19.1 67.8 67.3 19.1 65.8 18.8 18.8 18.8 19.0 17.0 67.2 61.6 67.2 17.6
C20 40.3 35.8 71.2 86.5 85.5 40.4 40.3 49.1 41.6 35.7 35.9 32.6 47.8 37.8 40.1 40.0 40.2 124.4
C21 13.3 12.8 32.8 25.8 26.0 13.3 13.4 178.5 12.0 18.6 18.7 20.3 175.2 13.3 12.9 12.6 13.3 138.4
C22 80.1 84.0 48.6 27.8 27.5 80.2 80.3 31.9 72.7 31.4 31.9 49.8 32.9 74.6 75.6 75.5 80.1 107.7
C23 27.9 63.6 106.8 34.2 34.2 27.9 27.8 32.8 34.0 31.1 31.8 208.9 123.5 31.6 33.1 33.1 27.3 153.6
C24 139.7 143.8 44.6 176.7 175.9 139.6 139.7 156.0 125.4 174.1 176.1 46.9 132.3 138.5 141.0 140.9 142.9 34.3
C25 128.0 127.7 34.1 -- -- 128.2 128.2 34.3 137.9 -- -- 35.7 155.4 129.8 128.2 128.1 128.0 38.5
C26 166.5 164.0 178.7 -- -- 166.6 166.7 22.0 61.4 -- -- 178.4 106.7 172.0 172.4 171.7 166.3 180.0
C27 17.1 16.8 14.5 -- -- 17.1 17.1 21.9 22.4 -- -- 17.7 17.7 12.5 20.6 20.5 17.0 18.9
C28 32.0 28.5 29.6 25.4 25.0 28.1 33.7 28.0 28.4 27.1 27.1 27.1 27.6 25.8 33.7 33.5 28.7 27.3
C29 25.2 26.6 15.1 16.5 27.0 15.5 26.1 21.9 15.5 18.9 18.9 18.9 21.8 22.0 26.1 25.8 23.8 20.4
C30 24.5 26.6 29.7 28.8 20.7 24.2 24.9 24.5 24.7 20.6 20.7 20.6 24.4 31.4 24.3 24.3 22.5 20.5
CO C1' C1' C1' C1' OCH3 C1' C1' C1' C1'
170.4 171.1 170.7 171.2 170.5 51.4 94.5 170.6 170.5 170.4
NO. 308a) 309b) 310a) 311b) 312a) 315a) 316b) NO. 308a) 309b) 310a) 311b) 312a) 315a) 316b)
C1 32.7 31.8 38.0 36.6 37.1 35.5 32.4 C18 17.7 17.7 18.0 17.8 17.7 17.7 19.6
C2 30.8 30.4 29.6 29.9 30.1 28.8 32.2 C19 22.4 22.4 25.5 24.9 23.0 20.0 16.3
C3 176.5 173.9 176.4 174.7 175.6 77.6 214.1 C20 36.2 36.2 36.2 36.0 139.9 40.1 205.2
C4 146.5 146.4 87.3 86.1 145.0 39.4 47.0 C21 18.5 18.5 18.1 18.1 19.0 17.5 31.2
C5 45.0 45.0 48.0 48.4 44.8 49.9 43.5 C22 31.9 27.7 31.9 31.3 126.3 66.9 26.9
C6 35.5 35.4 32.1 32.5 27.0 29.0 36.7 C23 31.9 32.4 31.6 31.0 75.2 -- 20.3
C7 67.9 67.8 72.9 73.1 61.3 69.5 198.3 C24 176.5 176.5 176.4 174.5 36.8 -- 17.5
C8 165.3 165.7 161.4 161.2 66.5 160.5 66.8 C25 -- -- -- -- 34.3 -- --
C9 137.4 137.1 135.4 135.1 163.0 141.9 68.1 C26 -- -- -- -- 179.0 -- --
C10 41.3 41.2 41.6 41.1 43.8 39.1 37.4 C27 -- -- -- -- 15.5 -- --
C11 200.4 200.4 199.8 200.2 130.0 200.3 200.6 C28 115.6 115.7 71.3 71.3 115.2 28.8 --
C12 52.1 52.0 50.9 50.8 201.1 52.8 46.0 C29 23.4 23.2 25.0 25.3 23.0 16.7
C13 47.3 41.2 45.3 45.2 59.1 47.7 45.5 C30 27.6 27.7 24.5 23.8 15.1 20.2
C14 53.4 53.3 50.9 50.6 51.8 54.5 54.8 CH2O 3-OCH3 OAc
C15 32.4 31.9 30.1 29.3 71.8 72.6 205.9 60.4 51.9 20.7
C16 27.8 32.4 27.2 29.5 31.9 36.6 36.4 CH3CH2O 24-OCH3 169.9
C17 50.1 50.1 50.2 50.0 44.3 45.4 52.4 14.4 51.8

Notes: NO. 1 N-BU 2' 30.8, N-BU 3' 19.3, N-BU 4' 13.9; NO. 2 Bu 4' 13.9; NO. 3 Bu 4' 13.9; NO. 24 OCH2CH3 14.1; NO. 29 OCOCH3 20.9; NO. 41 15-COCH3 21.3; NO.65 15-OCOCH3 21.1; NO. 73 7-OCH3 55.6; NO. 74 7-OCH3 54.5; NO.77 AcCH3 21.4, AcCH3 21.0; NO. 78 3-OCOCH3 21.2, 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 79 22-OCOCH3 21.0; NO. 80 15-OCOCH3 21.1, 22-OCOCH3, 170.6, 22-OCOCH3 21.0; NO. 81 22-OCOCH3 21.1; NO. 82 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 83 AcCH3 21.1, AcCH3 21.3, AcCH3 21.3, CO 170.3, CO 170.3, CO 170.5; NO. 84 AcCH3 21.0, AcCH3 21.6, AcCH3 21.7, CO 170.6, CO 170.1, CO 170.2, OCH3 55.2; NO. 99 COOCH3 51.9; NO. 100 OCH3 51.9; NO. 101 OCH3 51.9, COCH3 20.9, COCH3 170.2; NO. 102 OCH3 51.8, COCH3 20.8, COCH3 170.1; NO. 103 OCH3 51.9; NO. 104 OCH3 51.9; NO. 105 OCH3 51.9; NO. 118 C3' 73.7, C4' 69.7, C5' 63.7, COCH3 170.9, COCH3 21.4; NO. 120 C2' 74.0, C3' 79.2, C4' 71.4, C5' 79.0, C6' 62.5; NO. 127 OCH3 52.0; NO. 138 COO-CH2CH3 60.9, COOCH2CH3 14.4, CO of AcO-C(3) 171.1, CH3 of AcO-C(3) 21.5; NO. 139 COOCH2CH3 60.8, COOCH2CH3 14.4; NO. 145 C24' 6.8; NO. 149 CH3CO 170.4; NO. 150 CH3CO 21.4, CH3CO 21.3; NO. 151 C23 31.8(24S), C24 75.6(24S), C25 149.8(24S), C26 111.5(24S), C27 18.1(24S); NO. 153 C24' 21.5; NO. 167 AcCO 170.8, AcCO 171.0.; NO. 172 AcCH3 21.2, AcCH3 21.4, AcCH3 21.5, CO 170.7, CO 170.9, CO 170.2; NO. 173 AcCH3 21.0, CO 170.6; NO. 174 AcCH3 21.0, AcCH3 21.3, CO 170.6, CO 170.6; NO. 176 AcCO 170.0, AcCH3 21.4, AcCH3 21.3, AcCH3 21.0; NO. 178 AcCH3 21.2, AcCH3 21.2; NO. 184 15-OCOCH3 21.4, 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 185 AcCH3 21.5, CO 170.6, CO 171.2; NO. 186 AcCH3 21.7, CO 170.7, CO 170.9; NO. 193 C4' 20.9; NO. 222 Bu3' 19.3, Bu4' 13.9; NO. 223 Bu3' 19.3, Bu4' 13.9; NO. 226 COOCH3 20.8, OCH3 51.4, COCH3 170.0; NO. 230 COCH3 20.8, COCH3 170.1; NO. 231 OCH3 51.6, COCH3 20.9, COCH3 170.1; NO. 232 OCH3 51.7; NO. 233 C33 60.5, C34 14.2; NO. 243 OCH3 51.6, COCH3 20.8, COCH3 170.0; NO. 244 OCH3 51.6, COCH3 20.9, COCH3 170.1; NO. 249 C3' 19.3, C4' 13.9; NO. 275 C3' 145.2, C4' 34.5 C5' 25.6, C6' 122.1, C7' 136.9, C8' 39.0, C9' 25.6, C10' 125.5, C11' 134.5, C12' 38.7, C13' 13.8, C14' 16.2, C15', 169.0, C1'' 157.1, C2'' 112.7, C3'' 117.3, C4'' 148.2, C5'' 126.0, C6'' 119.8; NO. 276 C3' 133.3, C4' 35.9 C5' 28.5, C6' 124.6, C7' 136.7, C8' 38.9, C9' 27.3, C10' 126.8, C11' 135.8, C12' 69.0, C13' 13.7, C14' 16.2, C15' 172.3, C1'' 128.0, C2'' 149.3, C3'' 114.8, C4'' 151.2, C5'' 116.9, C6'' 117.8; NO. 277 C3' 27.0; NO. 278 CH3 26.4, CH3 23.5; NO. 288 C3' 146.3, C4' 34.6C5' 25.5, C6' 122.1, C7' 136.6, C8' 39.1, C9' 25.5, C10' 125.3, C11' 134.4, C12' 68.6, C13' 13.9, C14' 16.3, C15' 168.3, C1'' 157.0, C2'' 114.9, C3'' 117.2, C4'' 148.1, C5'' 126.1, C6'' 119.8; NO. 291 CH3 21.4; NO. 295 C2' 21.1; NO. 296 C2' 21.1; NO. 297 C2' 46.4, C3' 69.9 C4' 46.1, C5' 171. 9,3'-CH3 28.4, OCH3 51.2, C31 107.1; NO. 298 C2' 21.1; NO. 302 C2' 72.3, C3' 75.9, C4' 69.5, C5' 65.8, COCH3 170.9, COCH3 21.4, C241 25.7; NO. 303 22-OCOCH3 171.3, 22-OCOCH3, 21.2; NO. 304 C2' 20.7, C1'' 170.9, C2'' 21.1, OCH3 51.8; NO. 305 C2' 21.1, C1'' 170.8, C2'' 21.2, OCH3 51.8; NO. 306 C2' 20.7, OCH3 51.4. (a) Measured in C5D5N; (b) Measured in CDCl3; (c) Measured in CD3OD(50%) and CDCl3(50%); (d) Measured in DMSO-d6; (e) Measured in pyridine-d5; (f) Measured in CD3OD; (g) Measured in (CD3)2CO; (h) Measured in C6D6.

As summarized above, a large number of triterpenes together with their potential pharmacological activities are described from Ganoderma. Being inclined to complement the prior reviews, we summarized the triterpenes from Ganoderma. They contain 30 or 27 carbon atoms, including some with 24 carbon atoms. The great majority of the triterpenes possess double bonds on the ring, at C-8 (9), with hydroxy and carbonyl substituted at C-3, C-7, C-11, and C-15 generally. For this type, the carbon atoms mentioned above are usually a characteristic for its structural determination. The 13C-NMR data of hydroxy substituted C-3 appear from 77–80 ppm, while the data of carbonyl substituted increase to 208–218 ppm. As to the double bonds, the resonance of C-8 arises at 131–165 ppm and the C-9 signal arises at 134–165 ppm, fluctuated for the neighbouring substituent groups.

In the other type, with double bonds located at C-7(8) and C-9(11), the resonance of C-7 appears from 119 ppm to 121 ppm, while the C-8 signal increases to 140–143 ppm. The C-9 signal appears at 144–147 ppm, while the C-11 signal moves to 115–118 ppm. C-23 tends to be oxidized to a carbonyl with 13C-NMR signals appearing at 206 ppm to 217 ppm, or to hydroxy with signals in the 65–67 ppm range. When double bonds appear between C-20 and C-22, the C-23 signal will move to 197–200 ppm. Moreover, C-24 and C-25 are sometimes linked by double bonds in some Ganoderma triterpenes. In this case, the 13C-NMR peaks of C-24 appear at 144–156 ppm and those of C-25 appear at 126–140 ppm. According to the compiled 13C-NMR data, this review should provide a useful and fast way for the identification of GTs.

4. The Bioactivities of Ganoderma Triterpenes

4.1. Anti-Tumor Activity

Cancer has been acknowledged as a huge threat to human health and most governments are committed to diminish this threat. The urgent task of finding anti-tumor drugs with high efficiency and low toxicity have drawn countless researchers’ efforts directed to the discovery of lead compounds or bioactive ingredients from nature resources such as Ganoderma. The GTs were extensively evaluated for cytotoxic activities against a series of tumor cell lines. Compounds 45, 46, 164 and 204 showed cytotoxic effects against the tested tumor cell lines. Compound 46 exhibited the most potent cytotoxicity against LLC, T-47D, Sarcoma 180 and Meth-A tumor cells [25]. Compounds 62, 190 and 212 showed strong cytotoxic activities against human Hela cervical cancer cells [26]. According to Cheng’s report, the ganoderic alcohols showed stronger activities than ganoderic acids which implies that a hydroxy group substituted at 26 may be a very important structural feature for cytotoxic activity, however, the more hydroxyl groups there are, the lower the inhibitory activity will be [26]. Compounds 42 and 85 showed cytotoxicity against p388, Hela, BEL-7402, and SGC-7901 human cancer cell lines, with IC50 values in the 8–25 μM range [32]. Compounds 4752 were studied in vitro against Meth-A and LLC tumor cell lines [37]. Compound 187 displayed selective inhibitory activity against HL-60 cells, and compound 131 exhibited selective cytotoxic activity against MCF-7 cells. Compounds 7, 67 and 188 showed the ability to induce hPXR-mediated CYP3A4 expression [47]. Compounds 9, 23, 57 and 68 showed significant cytotoxic activity, with IC50 values of 18.7, 21.4, 16.2 and 20.1 μg/mL, respectively [48]. Compounds 77, 163, 170 and 173 were tested in vitro for their cytotoxic activities against 95D and Hela tumor cell lines with IC50 values ranging from 14.7 to 38.5 μM [49]. Compound 121 showed significant activity against T-24 cells, while compounds 119, 123, showed significant activity against T-24, HT-3, and CaSKi cells, respectively [60]. Compound 297 showed significant cytotoxic activity with an IC50 value of 2.5 μg/mL in the Hep-2 cell line [62]. Treatment of human hepatoma HuH-7 cells with compound 205 caused immediate inhibition of DNA synthesis as well as activation of ERK and JNK mitogen-activated protein kinases, and cell apoptosis. Molecular events of apoptosis including degradation of chromosomal DNA, decrease in the level of Bcl-xL, the disruption of mitochondrial membrane, cytosolic release of cytocherome c and activation of caspase-3 were elucidated. The ability of compound 205 to inhibit topoisomerases and to sensitize cancer cells towards apoptosis meets the criteria of a potential anticancer drug [88]. Compounds 30, 229 and 235 showed significant cytotoxic activities against Hep G2, Hep G2,2,15, and P-388 cell lines [91]. Compound 233 showed cytotoxicity against HL-60 and CA46 cancer cell lines [93]. Biological activity as an anti-tumor promoter was observed for compounds 279282 [101]. Compound 285 showed moderate cytotoxicity against liver cancer and lung cancer cell lines [27]. Compounds 140, 279, 281, 287, 292 and 312 inhibited the viability and growth of the HL-60 cell lines [103].

4.2. Anti-HIV and Anti-HIV-1 Protease Activity

It was reported that compounds 270, 272, 291 and 304306 were inhibitory against HIV-1 protease, with IC50 values for the most potent compounds ranging from 5 μg∙mL1 to 13 μg∙mL1 [102]. Moreover, compounds 190 and 210 were found to be active as anti-HIV-1 agents with an inhibitory concentration of 7.8 μg∙mL1 for both, and compounds 4, 11, 23, 28, 171 and 203 were moderately active inhibitors against HIV-1 protease with a 50% inhibitory concentration of 0.17–0.23 mM [18]. While compounds 5, 53, 201 and 204 showed significant anti-HIV-1 protease activity with IC50 values of 20–90 μM [38]. In addition, compounds 39, 224 and 255 inhibited human immunodeficiency virus-1 protease with IC50 values of 20–24 μM.

4.3. Neurotrophic Activity

A series of reports has shown that Ganoderma triterpenes exhibit neurotrophic activity. Bioassay results revealed that compounds 12 and 261 have nerve growth factor-like neuronal survival-promoting effects, whereas the two compounds mentioned above and compounds 10, 159 and 183 showed brain-derived neurotrophic factor-like neuronal survival-promoting activities [73]. Compounds 1 and 278, exhibiting specific anti-acetylc-holinesterase activity, are being examined as possible drug candidates for the treatment of Alzheimer’s and related neurodegenerative diseases. Compounds 62, 204, 210 and some other Ganoderma triterpenes exhibited moderate acetylcholinesterase-inhibitory activity, with IC50 values ranging from 9.40 to 31.03 μM. These results indicated that these lanostane triterpenes are preferential inhibitors of acetylcholinesterase and may be suitable as drug candidates [16].

4.4. Hepatoprotection

It is also reported that compound 11 showed significant hepatoprotective activity. However, increased doses of compound 11 (up to 10 times) did not further reduce GOT/GPT levels in the serum of the mice [107]. Compound 144 has an activity of lowering the levels GPT in mice with liver injury by CCl4 and GaNI and exhibits hepatoprotective effects [67].

4.5. Antiobesity Activity

In 2010, the inhibitory effect of triterpenes isolated from G. lucidum on adipocyte differentiation in 3T3-L1 cells was reported for the first time [17]. According to a report on the subsequent research, compound 249 reduced the triglyceride accumulation significantly by 72% at 80 μM and it effectively suppressed the glycerol-3-phosphate dehydrogenase activity in the cells. It suppressed the gene expressed of PPARγ, C/EBPα, and SREBP-1c in a dose-dependent manner during differentiation. These findings demonstrate that compound 249 contributes to the inhibitory effect on adipocyte differentiation in 3T3-L1 cells [96].

4.6. Hypoglycemic Activity

The inhibitory effect on aldose reductase was examined for compound 27 and its methyl ester. The results indicated that the IC50 of 27 is 22.8 μM, whereas that of its methyl ester is more than 200 μM, which suggested that a carboxyl group of side chain of compound 27 is essential for potent inhibitory activity because of much lower level of inhibitory activity of its methyl ester. However, the exact reason for the difference in inhibition between compound 27 and its methyl ester remains unclear [29]. Compound 169 was also found to have high α-glucosidase inhibition, with IC50 of 119.8 μM [108].

4.7. Other Bioactivities

Ganoderma has been investigated for other bioactivities. Compounds 45 and 58 were found to exhibit potent inhibitory activity against herpes simplex virus [42]. Compounds 13 and 15 were shown to inhibit histamine release from rat mast cells [21]. In the study on compounds 3 and 156, it was found they both exhibited inhibitory activities against the HMG-CoA reductase and acyl CoA acyltransferase [35]. Another study demonstrated that compounds 44 and 49 exhibited potent enhancement of ConA-induced mice splenocytes proliferation in vitro [36]. It was found that compounds 161, 189 and 316 possess the bioactivity to induce apoptosis in human promyelocytic leukemia HL-60 cells [75]. An investigation on the ability of some Ganoderma triterpenes to inhibit 5α-reductase in rat liver microsomes revealed that compounds 64, 161 and 206 showed the inhibitory activity. Further study suggested that a carboxyl group of the 17β-side chain of compound 206 was essential to elicit the inhibitory activity [89]. The in vitro tests showed that compounds 308 and 310 exhibited modest inhibitory activity against rabbit platelet aggregation induced by platelet activating factor (PAF), and compound 310 also displayed weak inhibition against platelet aggregation induced by adenosine diphosphate (ADP) [105]. The C-3 epimer of compound 172 also exhibited significant antimycobacterial activity against mycobacterium tuberculosis H37Ra [46].

5. Conclusions

Ganoderma triterpenes (GTs) are a class of compounds with various chemical structures and a diverse range of biological activities. Biomedical analysis has shown that triterpenes possess important pharmacological activities and are thought to be potential candidates for drug discovery, but their low abundance, complex procedures of extraction and purification, the difficult preparation of high purity triterpenoids from G .lucidum is currently limited at the laboratory scale. Thus, how to enhance the content of triterpenoids and improve the technology of the extraction and purification of triterpenoids from Ganoderma lucidum is a problem that needs to be solved. We can expect to enhance GT production through the regulation of GA biosynthesis, thus promoting the industrial development of G. lucidum and provide an important resource for the development and application of new antineoplastic, anti-HIV, and other drugs.

Based on the above analysis of structural complexity and functional group variety, it is especially important to prove the structure-function relationships to make up for the inadequacy of this aspect. Although extensive research has been done on this herb, there is still a lot of scope for further research, especially on the mechanisms of biological activity of GTs with emphasis on agents with anti-tumor, anti-HIV, neurotrophic properties. G. lucidum and G. sinense that are recorded in the pharmacopoeia of China in 2010 have been widely applied in China [8]. Their long-standing medicinal history indicates their irreplaceable functions. In further study, researchers may need to pay more attention to the two species, and focus on the active substances such as the triterpenes summarized above. To achieve better quality control, the studies on other species are also important, so that the differences between species can be illustrated clearly. Additionally, more important bioactive constituents should be integrated into the quality control system of Ganoderma. Further experiments including in vitro, in vivo and clinical studies should be encouraged to identify any potential side effects.

Acknowledgments

This work was supported by the National Science-technology Support Plan Project (NO. 2012BAI29B00).

Author Contributions

Qing Xia, Huazheng Zhang, Gaimei She, and Lanzhen Zhang have all been involved in drafting this review. Qing Xia and Huazheng Zhang contributed equally to this work. Xuefei Sun, Haijuan Zhao, Lingfang Wu and Xin Mao discussed the results and commented on the manuscript. Dan Zhu, Guanghui Yang, Yanyan Shao and Xiaoxue Zhang corrected the 13C-NMR data. All authors read and approved the final manuscript.

Conflicts of Interest

The authors declare that they have no competing interests.

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