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. 2011 Jan 26;16(2):1070–1102. doi: 10.3390/molecules16021070

Table 1.

Compounds isolated from Bidens pilosa L.

N°. Name Alternative name Structure Plant part Country Ref.
Aliphatic natural products
Saturated unbranched hydrocarbons
1 heneicosane CH3(CH2)19CH3 AP Tanzania [44]
2 dodosane CH3(CH2)20CH3 AP Tanzania [44]
3 tricosane CH3(CH2)21CH3 AP Tanzania [44]
4 tetracosane CH3(CH2)22CH3 AP Tanzania [44]
5 pentacosane CH3(CH2)23CH3 AP Tanzania [44]
6 hexacosane CH3(CH2)24CH3 AP Tanzania [44]
7 heptacosane CH3(CH2)25CH3 AP Tanzania [44]
8 octacosane CH3(CH2)26CH3 NF Taiwan [91]
AP Tanzania [44]
9 nonocosane CH3(CH2)27CH3 NF Taiwan [91]
AP Tanzania [44]
10 triacontane CH3(CH2)28CH3 NF Taiwan [91]
AP Tanzania [44]
11 hentriacontane CH3(CH2)29CH3 NF Taiwan [91]
AP Tanzania [44]
12 dotriacontane CH3(CH2)30CH3 NF Taiwan [91]
AP Tanzania [44]
13 tritriacontane CH3(CH2)31CH3 NF Taiwan [91]
AP Tanzania [44]
Saturated unbranched alcohols
14 2-butoxy-ethanol CH3(CH2)3OCH2CH2OH EP Taiwan [85]
15 tetracosan-1-ol CH3(CH2)22CH2OH AP Tanzania [44]
16 hexacosan-1-ol CH3(CH2)24CH2OH AP Tanzania [44]
17 1-octacosanol CH3(CH2)26CH2OH AP Tanzania [44]
18 1-hentriacontanol CH3(CH2)29CH2OH NF Taiwan [91]
Saturated unbranched carboxylic acids
19 tetradecanoic acid myristic acid CH3(CH2)12CO2H AP Tanzania [44]
20 hexadecanoic acid palmitic acid CH3(CH2)14CO2H AP Tanzania [44]
21 octadecanoic acid stearic acid CH3(CH2)16CO2H AP Tanzania [44]
22 eicosanoic acid arachidic acid CH3(CH2)18CO2H AP Tanzania [44]
23 docosanoid acid behenic acid CH3(CH2)20CO2H LF not stated [84]
Unbranched aliphatic carboxylic acid esters
24 2-butenedioic acid graphic file with name molecules-16-01070-i001.jpg AP China [121]
AP China [102]
25 (Z)-9-octadecenoic acid oleic acid graphic file with name molecules-16-01070-i002.jpg AP Tanzania [44]
26 (E)-9-octadecenoic acid elaidic acid graphic file with name molecules-16-01070-i003.jpg LF not stated [84]
27 (Z,Z)-9,12-octadecadienoic acid linolic acid/linoleic acid graphic file with name molecules-16-01070-i004.jpg AP Tanzania [44]
EP Taiwan [85]
28 (Z,Z,Z)-9,12,15-octadecatrienoic acid α-linolenic acid graphic file with name molecules-16-01070-i005.jpg EP Taiwan [85]
29 (Z,Z)-9,12-octadecadienoic acid, ethyl ester ethyl linoleate graphic file with name molecules-16-01070-i006.jpg EP Taiwan [85]
30 (Z,Z,Z)-9,12,15-octadecatrienoic acid, methyl ester methyl linolenate graphic file with name molecules-16-01070-i007.jpg EP Taiwan [85]
31 (Z,Z,Z)-9,12,15-octadecatrienoic acid, ethyl ester ethyl linolenate graphic file with name molecules-16-01070-i008.jpg EP Taiwan [85]
32 (Z)-9-octadecenoic acid, 2-butoxyethyl ester 2-butoxyethyl oleate graphic file with name molecules-16-01070-i009.jpg EP Taiwan [85]
33 2-butoxyethyl linoleate graphic file with name molecules-16-01070-i010.jpg EP Taiwan [85]
34 (Z,Z,Z)-9,12,15-octadecatrienoic acid, butoxyrthyl ester 2-butoxyethyl linolenate graphic file with name molecules-16-01070-i011.jpg EP Taiwan [85]
Acetylenic hydrocarbons
35 1,7E,9E,15E-heptadecatetraene-11,13-diyne heptadeca-2E,8E,10E,16-tetraen-4,6-diyne graphic file with name molecules-16-01070-i012.jpg NF China [99]
36 1,11-tridecadiene-3,5,7,9-tetrayne graphic file with name molecules-16-01070-i013.jpg RT not stated [2]
37 1-tridecaene-3,5,7,9,11-pentayne pentayneene graphic file with name molecules-16-01070-i014.jpg LF not stated [2]
NF Egypt [86]
38 5-tridecaene-7,9,11-triyne-3-ol graphic file with name molecules-16-01070-i015.jpg NF Egypt [86]
39 2,10,12-tridecatriene-4,6,8-triyn-1-ol graphic file with name molecules-16-01070-i016.jpg PNS not stated [51]
40 2,12-tridecadiene-4,6,8,10-tetrayn-1-ol 1,11-tridecadiene-3,5,7,9-tetrayn-13-ol graphic file with name molecules-16-01070-i017.jpg RT not stated [2]
NF Egypt [86]
41 2,12-tridecadiene-4,6,8,10-tetraynal 1,11-tridecadiene-3,5,7,9-tetrayne-13-al graphic file with name molecules-16-01070-i018.jpg RT Germany [122]
42 2,12-tridecadiene-4,6,8,10-tetrayn-1-ol,1-acetate 1,11-tridecadiene-3,5,7,9-tetrayne-13-acetate graphic file with name molecules-16-01070-i019.jpg RT not stated [2]
43 (5E)-1,5-tridecadiene-7,9-diyn-3,4,12-triol graphic file with name molecules-16-01070-i020.jpg AP China [100]
44 (6E,12E)-3-oxo-tetradeca-6,12-dien-8,10-diyn-1-ol graphic file with name molecules-16-01070-i021.jpg AP China [100]
45 (E)-5-tridecene-7,9,11-triyne-1,2-diol 1,2-dihydroxy-5(E)-tridecene-7,9,11-triyne graphic file with name molecules-16-01070-i022.jpg EP Taiwan [78]
46 (E)-6-tetradecene-8,10,12-triyne-1,3-diol 1,3-dihydroxy-6(E)-tetradecene-8,10,12-triyne graphic file with name molecules-16-01070-i023.jpg EP Taiwan [77]
EP Taiwan [65]
EP Taiwan [78]
47 (2R,3E,11E)-3,11-tridecadiene-5,7,9-triyne-1,2-diol safynol graphic file with name molecules-16-01070-i024.jpg NF Egypt [86]
NF China [99]
48 5,7,9,11-tridecatetrayne-1,2-diol 1,2-dihydroxy-trideca-5,7,9,11-tetrayne graphic file with name molecules-16-01070-i025.jpg EP Taiwan [77]
EP Taiwan [78]
49 (R)-3,5,7,9,11-tridecapentayne-1,2-diol (R)-1,2-dihydroxy-trideca-3,5,7,9,11-pentayne graphic file with name molecules-16-01070-i026.jpg AP Japan [71]
50 (4E)-1-(hydroxyl-methyl)-4-dodecene-6,8,10-triyn-1-yl-β-D-glucopyranoside 2-β-D-gluco-pyranosyloxy-1-hydroxy-5(E)-tridecene-7,9,11-triyne graphic file with name molecules-16-01070-i027.jpg AP USA [54]
EP Taiwan [75]
EP Taiwan [123]
EP Taiwan [65]
EP Taiwan [49]
LF Taiwan [124]
51 (4E)-1-(2-hydroxy-ethyl)-4-dodecene-6,8,10-triyn-1-yl-β-D-glucopyranoside 3-β-D-gluco-pyranosyloxy-1-hydroxy-6(E)-tetradecene-8,10,12-triyne graphic file with name molecules-16-01070-i028.jpg AP USA [54]
AP China [102]
EP Taiwan [75]
EP Taiwan [123]
EP Taiwan [65]
EP Taiwan [49]
LF Taiwan [124]
AP China [100]
52 3-hydroxy-6-tetra-decene-8,10,12-triynyl-β-D-gluco-pyranoside β-D-gluco-pyranosyloxy-3-hydroxy-6E-tetradecene-8,10,12-triyne graphic file with name molecules-16-01070-i029.jpg EP Mexico [53]
53 1-(hydroxymethyl)-4,6,8,10-dodeca-tetrayn-1-yl-β-D-glucopyranoside 2-β-D-gluco-pyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne , cytopiloyne graphic file with name molecules-16-01070-i030.jpg EP Taiwan [49]
EP not stated [82]
LF Taiwan [124]
54 2-O-D-glucosyltrideca-11E-en-3,5,7,9-tetrayn-1,2-diol graphic file with name molecules-16-01070-i031.jpg LF Brazil [61]
55 (R)-1-(hydroxy-methyl)-2,4,6,8,10-dodecapentayn-1-yl-β-D-glucopyranoside 2-β-D-gluco-pyranosyloxy-1-hydroxytrideca-3,5,7,9,11-pentayne graphic file with name molecules-16-01070-i032.jpg AP China [102]
AP Japan [71]
56 1-[[(carboxy-acetyl)oxy]methyl]-4,6,8,10-dodeca-tetraynyl-β-D-glucopyranoside graphic file with name molecules-16-01070-i033.jpg AP Japan [125]
57 (4E)-1-[[(carboxy-acetyl)oxy]-methyl]-4-dodecene-6,8,10-triynyl-β-D-gluco-pyranoside graphic file with name molecules-16-01070-i034.jpg AP Japan [125]
58 (4E)-1-[[(carboxy-acetyl)oxy]-ethyl]-4-dodecene-6,8,10-triynyl-β-D-gluco-pyranoside graphic file with name molecules-16-01070-i035.jpg AP Japan [125]
59 (5E)-5-heptene-1,3-diyn-1-yl-benzene 1-phenylhepta-1,3-diyn-5-en graphic file with name molecules-16-01070-i036.jpg EP Taiwan [85]
60 7-phenyl-2(E)-heptene-4,6-diyn-1-ol graphic file with name molecules-16-01070-i037.jpg RT not stated [2]
AP China [100]
61 7-phenyl-2(E)-heptene-4,6-diyn-1-ol-acetate graphic file with name molecules-16-01070-i038.jpg RT not stated [2]
RT Brazil [50]
RT Brazil [52]
62 7-phenyl-4,6-heptadiyn-2-ol (-)-pilosol A graphic file with name molecules-16-01070-i039.jpg EPAP TaiwanChina [85]
[100]
63 7-phenylhepta-4,6-diyn-1,2-diol graphic file with name molecules-16-01070-i040.jpg AP China [100]
64 1,3,5-heptatriyn-1-yl-benzene 1-phenylhepta-1,3,5-triyne graphic file with name molecules-16-01070-i041.jpg LF not stated [2]
LTC not stated [97]
AP Tanzania [44]
AP China [121]
EP Taiwan [85]
RT Brazil [52]
AP China [100]
65 7-phenyl-2,4,6-heptatriyn-1-ol graphic file with name molecules-16-01070-i042.jpg LF not stated [2]
AP China [100]
66 7-phenyl-2,4,6-heptatriyn-1-ol-acetate graphic file with name molecules-16-01070-i043.jpg LF not stated [2]
67 5-(2-phenylethynyl)-2-thiophene methanol graphic file with name molecules-16-01070-i044.jpg AP China [100]
68 5-(2-phenylethynyl)-2β-glucosylmethyl-thiophene graphic file with name molecules-16-01070-i045.jpg AP China [100]
Simple aromatic hydrocarbons
Simple phenols
69 1,2-benzenediol pyrocatechin graphic file with name molecules-16-01070-i046.jpg EP Japan [87]
70 4-ethyl-1,2-benzenediol pyrocatechol graphic file with name molecules-16-01070-i047.jpg EP Japan [87]
71 dimethoxyphenol graphic file with name molecules-16-01070-i048.jpg RT Japan [87]
72 4-ethenyl-2-methoxy-phenol p-vinylguaiacol graphic file with name molecules-16-01070-i049.jpg EP Japan [87]
73 2-hydroxy-6-methylbenzaldehyde 6-methyl-salicylaldehyde graphic file with name molecules-16-01070-i050.jpg EP Japan [87]
74 benzene-ethanol 2-phenyl-ethanol graphic file with name molecules-16-01070-i051.jpg EP Taiwan [85]
Simple aryl aldehydes
75 4-hydroxy-3-methoxy-benzaldehyde vanillin graphic file with name molecules-16-01070-i052.jpg AP Japan [87]
76 3-hydroxy-4-methoxy-benzaldehyde vanillin, iso graphic file with name molecules-16-01070-i053.jpg LF Japan [87]
Simple benzoic acids and their homologues
77 4-hydroxy-benzoic acid p-hydroxybenzoic acid graphic file with name molecules-16-01070-i054.jpg EP Japan [87]
78 2-hydroxy-benzoic acid salicylic acid graphic file with name molecules-16-01070-i055.jpg ST/RT Japan [87]
79 3,4-dihydroxy-benzoic acid protocatechuic acid graphic file with name molecules-16-01070-i056.jpg EP Japan [87]
80 4-hydroxy-3-methoxy-benzoic acid vanillic acid graphic file with name molecules-16-01070-i057.jpg AP Uganda [110]
RT Japan [87]
81 3,4,5-trihydroxy-benzoic acid gallic acid graphic file with name molecules-16-01070-i058.jpg EP China [126]
Phenylpropanoids
Simple phenylpropanoids
82 3-(4-hydroxyphenyl)-2-propenoic acid p-coumaric acid graphic file with name molecules-16-01070-i059.jpg EP Japan [87]
83 2-methoxy-4(2-propen-1-yl)-phenol eugenol graphic file with name molecules-16-01070-i060.jpg LF/RT Japan [87]
84 3-(4-hydroxy-3-methoxyphenyl)-2propenoic acid ferulic acid graphic file with name molecules-16-01070-i061.jpg EP Japan [87]
85 3-(3,4-dihydroxy-phenyl)-2-propenoic acid caffeic acid graphic file with name molecules-16-01070-i062.jpg EP Japan [87]
AP Japan [62]
86 3-propyl-3-[(2,4,5-trimetoxyphenyl)-methoxy]-2,4-pentanedione 3-propyl-3-(2,4,5-trimethoxy)benzyloxy-pentan-2,4-dione graphic file with name molecules-16-01070-i063.jpg LF India [90]
Coumaric and caffeoyl esters
87 3-(3,4-dihydroxy-phenyl)-2-propenoic acid, ethyl ester caffeate, ethyl graphic file with name molecules-16-01070-i064.jpg NF Taiwan [127]
EP Taiwan [65]
EP Taiwan [78]
88 2-[[3-(3,4-dihydroxy-phenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-2-methyl-butanoic acid d-erythronic acid, 2-O-caffeoyl-2-C-methyl graphic file with name molecules-16-01070-i065.jpg LF Japan [88]
89 2-[[3-(3,4-dihydroxy-phenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-2-methyl-butanoic acid,methyl ester d-erythronate, methyl 2-O-caffeoyl-2-C-methyl graphic file with name molecules-16-01070-i066.jpg LF Japan [88]
90 3-[[3-(3,4-dihydroxy-phenyl)-1-oxo-2-propenyl]oxy]-2,4-dihydroxy-2-methyl-butanoic acid,methyl ester d-erythronate, methyl 3-O-caffeoyl-2-C-methyl graphic file with name molecules-16-01070-i067.jpg LF Japan [88]
91 4-(acetyloxy)-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-2-hydroxy-2-methyl-butanoic acid graphic file with name molecules-16-01070-i068.jpg NF Japan [70]
92 3-(3,4-dihydroxyphenyl)- tetrahydro-4-hydroxy-4-methyl-5-oxo-3-furanyl ester-2 propenoic acid 3-O-caffeoyl-2-C-methyl-D-erythrono-1,4-lactone graphic file with name molecules-16-01070-i069.jpg LF Japan [88]
93 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4,5-trihydroxy-cyclo-hexanecarboxylic acid chlorogenic acid graphic file with name molecules-16-01070-i070.jpg AP Japan [83]
EP Taiwan [79]
AP Japan [62]
94 4-[[3-(3,4-dihydroxy-phenyl)-1-oxo-2-propen-1-yl]-oxy]-1,3,5-trihydroxy-cyclo-hexanecarboxylic acid 4-O-caffeoylquinic acid graphic file with name molecules-16-01070-i071.jpg AP Japan [83]
95 3,4-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-oxy]-1,5-dihydroxy-cyclohexane--carboxylic acid 3,4-di-O-caffeoylquinic acid graphic file with name molecules-16-01070-i072.jpg AP Japan [83]
EP Taiwan [79]
EP Taiwan [75]
EP Taiwan [65]
96 3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-oxy]-1,4-dihydroxy-cyclohexane-carboxylic acid 3,5-di-O-caffeoylquinic acid graphic file with name molecules-16-01070-i073.jpg AP Japan [83]
EP Taiwan [79]
EP Taiwan [75]
EP Taiwan [65]
97 3,4-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-oxy]-1,5-dihydroxy-cyclohexane-carboxylic acid 4,5-di-O-caffeoylquinic acid graphic file with name molecules-16-01070-i074.jpg EP Taiwan [79]
EP Taiwan [75]
EP Taiwan [65]
98 3-[4-[[6-O-[3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-β-D-glucopyranosyl]-oxy]-phenyl]-2-propenoic acid β-D-p-coumaric acid, 4-O-(6-O-p-coumaroyl-glucopyranosyl) graphic file with name molecules-16-01070-i075.jpg LF Japan [89]
99 3-[4-[[2-O-acetyl-6-O-[3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-β-D-glucopyranosyl]-oxy]-phenyl]-2-propenoic acid β-D-p-coumaric acid, 4-O-(2-O-acetyl-6-O-p-coumaroyl-glucopyranosyl) graphic file with name molecules-16-01070-i076.jpg LF Japan [89]
AP China [121]
Coumarins
100 6,7-dihydroxy-2H-1-benzopyran-4-one esculetin graphic file with name molecules-16-01070-i077.jpg NF Egypt [86]
Flavonoids
Aurones
101 2-[(3,4-dihydroxy-phenyl)-methylene]-6-hydroxy-3(2H)-benzofuranone sulfuretin graphic file with name molecules-16-01070-i078.jpg AP China [102]
102 2-[(3,4-dihydroxy-phenyl)-methylene]-6,7-dihydroxy-3(2H)-benzofuranone aurone, (Z)-6,7,3’,4’-tetrahydroxy; maritimetin graphic file with name molecules-16-01070-i079.jpg AP China [102]
103 2-[(3,4-dihydroxy-phenyl)-methylene]-6-(β-D-glucopyranos-yloxy)-7-hydroxy-3(2H)-benzofuranone aurone, (Z)-6-O-β-D-glucopyranosyl-6,7,3',4'-tetrahydroxy; maritimein graphic file with name molecules-16-01070-i080.jpg LFAPLF Japan [89]
China [102]
China [59]
104 2-[(3,4-dihydroxy-phenyl)-methylene]-7-(β-D-glucopyranos-yloxy)-6-hydroxy-3(2H)-benzofuranone aurone, (Z)-7-O-β-D-glucopyranosyl-6,7,3',4'-tetrahydroxy graphic file with name molecules-16-01070-i081.jpg LF Japan [89]
105 6-[(6-O-acetyl-β-D-glucopyranosyl)oxy]-2-[(3,4-dihydroxy-phenyl)-methylene]-7-hydroxy-3(2H)-benzofuranone aurone, (Z)-6-O-( 6-O-acetyl-β-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxy graphic file with name molecules-16-01070-i082.jpg LF AP Japan [89]
China [102]
106 6-[(3,6-di-O-acetyl-β-D-glucopyranosyl)-oxy]-2-[(3,4-di-hydroxyphenyl)-methylene]-7-hydroxy-3(2H)-benzofuranone aurone, (Z)-6-O-(3,6-di-O-acetyl-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxy; bidenoside A graphic file with name molecules-16-01070-i083.jpg LF China [59]
107 6-[(4,6-di-O-acetyl-β-D-glucopyranosyl)-oxy]-2-[(3,4-di-hydroxyphenyl)-methylene]-7-hydroxy-3(2H)-benzofuranone aurone, (Z)-6-O-(4”,6”-diacetyl-β-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxy graphic file with name molecules-16-01070-i084.jpg LF not stated [128]
AP China [121]
AP China [102]
108 2-[(3,4-dihydroxy-phenyl)-methylene]-7-hydroxy-6-[(2,4,6-tri-O-acetyl-β-D-gluco-pyranosyl)-oxy-3(2H)-benzofuranone] aurone, (Z)-6-O-(2”,4”,6”-triacetyl-β-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxy graphic file with name molecules-16-01070-i085.jpg LF not stated [128]
AP China [121]
109 2-[(3,4-dihydroxy-phenyl)-methylene]-7-hydroxy-6-[(3,4,6-tri-O-acetyl-β-D-gluco-pyranosyl)-oxy]-3(2H)-benzofuranone aurone, (Z)-6-O-(3”,4”,6”-triacetyl-β-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxy graphic file with name molecules-16-01070-i086.jpg AP China [121]
AP China [102]
110 2-[(3,4-dihydroxy-phenyl)-methylene]-7-hydroxy-6-[[6-O-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-β-D-glucopyranosyl]oxy]-3(2H)-benzofuranone aurone, (Z)-6-O-(6-O-p-coumaroyl-β-D-glucopyranosyl)-6,7,3',4'-tetrahydroxy graphic file with name molecules-16-01070-i087.jpg LF Japan [89]
Chalcones
111 1-[2-(β-D-gluco-pyranosyloxy)-4-hydroxyphenyl]-2-hydroxy-3-(3-hydroxyphenyl)- 2-propen-1-one chalcone, α,3,2’,4’-tetrahydroxy-2’-O-β-D-glucopyranosyl graphic file with name molecules-16-01070-i088.jpg AP China [102]
112 1-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-2-propen-1-one butein graphic file with name molecules-16-01070-i089.jpg AP China [102]
113 3-(3,4-dihydroxy-phenyl)-1-(2,3,4-trihydroxy-phenyl)-2-propen-1-one okanin graphic file with name molecules-16-01070-i090.jpg LF China [59]
114 3-(3,4-dihydroxy-phenyl)-1-[3-(β-D-glucopyranosyloxy)-2,4-dihydroxyphenyl]-2-propen-1-one okanin 3’-O-β-D-glucoside graphic file with name molecules-16-01070-i091.jpg LF Germany [129]
LF Germany [130]
FL Germany [109]
115 3-(3,4-dihydroxy-phenyl)-1-[4-(β-D-glucopyranosyloxy)-2,3-dihydroxyphenyl]-2-propen-1-one okanin 4’-O-β-D-glucopyranoside; marein graphic file with name molecules-16-01070-i092.jpg FL Germany [109]
LF Japan [89]
116 okanin 4’-O-β-D-(6”-O-acetylglucoside) graphic file with name molecules-16-01070-i093.jpg FL Germany [109]
117 1-[4-[(4,6-di-O-acetyl-β-D-glucopyranosyl)-oxy]-2,3-dihydroxy-phenyl]-3-(3,4-di-hydroxyphenyl)-2-propen-1-one okanin 4’-O-β-D-(4”,6”-diacetyl)-glucopyranoside graphic file with name molecules-16-01070-i094.jpg AP China [121]
118 okanin 4’-O-β-D-(2”,4”,6”-triacetyl)-glucoside graphic file with name molecules-16-01070-i095.jpg LF Germany [129]
119 okanin 4’-O-β-D-(3”,4”,6”-triacetyl)-glucoside graphic file with name molecules-16-01070-i096.jpg AP China [121]
120 1-[2,3-dihydroxy-4-[[6-O-[3-(4-hydroxy-phenyl)-1-oxo-2-propenyl]-β-D-glucopyranosyl]oxy]-phenyl]-3-(3,4-dihydroxyphenyl)-2-propen-1-one okanin 4’-O-β-D-(6”-trans-p-coumaroyl) glucoside graphic file with name molecules-16-01070-i097.jpg LF Germany [129]
121 okanin 4’-O-β-D-(4”-acetyl-6”-trans-p-coumaroyl)-glucoside graphic file with name molecules-16-01070-i098.jpg LF Germany [131]
122 okanin 4’-O-β-D-(2”,4”-diacetyl-6”-trans-p-coumaroyl)-glucoside graphic file with name molecules-16-01070-i099.jpg LF Germany [131]
123 okanin 4’-O-β-D-(3”,4”-diacetyl-6”-trans-p-coumaroyl)-glucopyranoside graphic file with name molecules-16-01070-i100.jpg LF Germany [131]
124 okanin 4’-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside] graphic file with name molecules-16-01070-i101.jpg FL Germany [109]
125 okanin 3’,4’-di-O-β-D-glucoside graphic file with name molecules-16-01070-i102.jpg FL Germany [109]
126 1-[3-(β-D-gluco-pyranosyloxy)-2,4-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-2-propen-1-one okanin 4-methyl ether-3’-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i103.jpg LF Germany [130]
AP China [102]
127 okanin 4-methyl ether-3’,4’-di-O-β-(4”,6”,4’’’,6’’’-tetracetyl)-glucopyranoside graphic file with name molecules-16-01070-i104.jpg AP China [100]
128 chalcone, 2’,4’,6’-trimethoxy-4-O-D-glucopyranosyl-dihydro NF LF China [59]
Flavanones
129 2-(3,4-dihydroxy-phenyl)-2,3-dihydro-7,8-dihydroxy-4H-1-benzopyran-4-one okanin,iso graphic file with name molecules-16-01070-i105.jpg LF China [59]
130 2-(3,4-dihydroxy-phenyl)-2,3-dihydro-8-hydroxy-7-[(2,4,6-tri-O-acetyl-β-D-gluco-pyranosyl)oxy]-4H-1-benzopyran-4-one okanin 7-O-β-D-(2”,4”,6”-triacetyl)-glucopyranoside, iso graphic file with name molecules-16-01070-i106.jpg AP China [121]
Flavones
131 5,7-dihydroxy-2-(4-hydroxyphenyl)- 4H-1-benzopyran-4-one apigenin graphic file with name molecules-16-01070-i107.jpg AP Tanzania [44]
AP China [100]
132 7-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one apigenin 7-O-glucopyranoside graphic file with name molecules-16-01070-i108.jpg AP Tanzania [44]
133 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one luteolin graphic file with name molecules-16-01070-i109.jpg AP Tanzania [44]
AP China [121]
AP China [102]
AP China [100]
AP Vietnam [132]
134 2-(3,4-dihydroxy-phenyl)-7-(β-D-gluco-pyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one luteolin 7-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i110.jpg AP Tanzania [44]
135 5,7-dimethoxy-6-(5-methoxy-6-methyl-4-oxo-4H-pyran-3-yl)-2-phenyl-4H-1-benzopyran-4-one 5-O-methylhoslundin graphic file with name molecules-16-01070-i111.jpg AP Uganda [110]
Flavonols
136 3-(β-D-gluco-pyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)- 4H-1-benzopyran-4-one astragalin; kaempferol-3-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i112.jpg AP China [102]
137 kaempferol 3-(2,3-di-E-p-coumaroyl-α-L-rhamnopyranoside) NF AP Vietnam [132]
138 2-(3,4-dihydroxy-phenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-3,6-dimethoxy-4H-1-benzopyran-4-one axillaroside graphic file with name molecules-16-01070-i113.jpg AP China [100]
139 5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3,6-di-methoxy-4H-1-benzopyran-4-one centaureidin graphic file with name molecules-16-01070-i114.jpg EP Taiwan [74]
140 7-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one centaurein graphic file with name molecules-16-01070-i115.jpg AP Japan [83]
EP Taiwan [79]
EP Taiwan [74]
141 eupatorin, iso NF NF China [99]
142 2-(3,4-dimethoxy-phenyl)-7-(β-D-glucopyranosyloxy)-3,5-dihydroxy-8-methoxy-4H-1-benzopyran-4-one graphic file with name molecules-16-01070-i116.jpg NF Japan [70]
143 7-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxy-4H-1-benzopyran-4-one graphic file with name molecules-16-01070-i117.jpg NF Japan [70]
144 isorhamnetin 3-[O-α-L-rhamno-pyranosyl-(1-2)-β-D-glucopyranoside] NF AP Vietnam [132]
145 7-[(6-deoxy-α-L-mannopyranosyl)oxy]-3-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one luteoside graphic file with name molecules-16-01070-i118.jpg AP China [100]
146 luteolin 3-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i119.jpg AP Tanzania [44]
147 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3,6-di-methoxy-4H-1-benzopyran-4-one quercetagetin 3,6,3′-trimethyl ether graphic file with name molecules-16-01070-i120.jpg AP China [100]
148 quercetagetin 3,7,3’-trimethyl ether-6-O-β-glucoside graphic file with name molecules-16-01070-i121.jpg AP China [100]
149 7-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one jacein; quercetagetin 3,6,3′-trimethyl ether-7-O-β-glucoside graphic file with name molecules-16-01070-i122.jpg AP Japan [83]
EP Taiwan [79]
AP China [100]
150 2-(3,4-dihydroxy-phenyl)-3,5,7-trihydroxy- 4H-1-benzopyran-4-one quercetin graphic file with name molecules-16-01070-i123.jpg AP China [102]
LF China [59]
EP China [133]
151 2-(3,4-dihydroxy-phenyl)-3-(β-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one quercetin 3-O-β-D-galactoside; hyperin; hyperoside graphic file with name molecules-16-01070-i124.jpg AP Tanzania [44]
AP Japan [83]
NF China [99]
AP Japan [62]
LF China [59]
EP China [133]
152 2-(3,4-dihydroxy-phenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one quercetin 3-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i125.jpg AP Tanzania [44]
LF Japan [89]
AP China [102]
AP Japan [62]
153 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-1-benzo-pyran-3-yl-β-D-glucopyranosiduronic acid quercetin 3-O-β-D-glucuronopyranoside graphic file with name molecules-16-01070-i126.jpg AP Tanzania [44]
AP Japan [83]
154 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranosyl]oxy]-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy- 4H-1-benzopyran-4-one quercetin 3-O-robinobioside graphic file with name molecules-16-01070-i127.jpg AP Japan [83]
EP Taiwan [79]
156 7-(β-D-glucopyranos-yloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-4H-1-benzopyran-4-one quercetin 3,3’-dimethyl ether 7-O-β-D-glucopyranoside graphic file with name molecules-16-01070-i128.jpg RT Brazil [134]
RT Brazil [52]
RT Brazil [135]
157 7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-methoxy-4H-1-benzopyran-4-one quercetin 3,3’-dimethyl ether 7-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside graphic file with name molecules-16-01070-i129.jpg RT Brazil [134]
RT Brazil [52]
158 7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-4H-1-benzopyran-4-one quercetin 3,4’-dimethyl ether-7-O-rutinoside graphic file with name molecules-16-01070-i130.jpg AP China [121]
AP China [102]
159 2-(3,4-dihydroxy-phenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one isoquercitrin graphic file with name molecules-16-01070-i131.jpg AP Japan [83]
AP China [102]
Terpenoids
Sesquiterpenes
160 3,7,11,11-tetramethyl-bicyclo[8.1.0]undeca-2,6-diene bicyclogermacrene graphic file with name molecules-16-01070-i132.jpg LF Brazil [46]
161 4,11,11-trimethyl-8-methylenebicyclo-[7.2.0]undec-4-ene E-caryophyllene graphic file with name molecules-16-01070-i133.jpg LF Brazil [46]
162 1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene germacrene-D graphic file with name molecules-16-01070-i134.jpg LF Brazil [46]
163 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-cyclohexene Z-γ-bisabolene graphic file with name molecules-16-01070-i135.jpg LF Brazil [46]
164 decahydro-1,1,4-trimethyl-7-methylene-1H-cycloprop[e]-azulene β-gurjunene graphic file with name molecules-16-01070-i136.jpg LF Brazil [46]
165 2,6,6,9-tetramethyl-1,4,8-cycloundeca-triene α-humulene;α-caryophyllene graphic file with name molecules-16-01070-i137.jpg LF Brazil [46]
166 δ-muurolene graphic file with name molecules-16-01070-i138.jpg LF Brazil [46]
167 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethylidene)-naphthalene selina-3,7(11)-diene graphic file with name molecules-16-01070-i139.jpg LF Brazil [46]
Diterpenes
168 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-ol phytol graphic file with name molecules-16-01070-i140.jpg EP Taiwan [85]
169 3,7,11,15-tetramethyl-2-hexadecenoic acid phytenic acid graphic file with name molecules-16-01070-i141.jpg EP Taiwan [85]
170 3,7,11,15-tetramethyl-2-hexadecenyl ester-heptanoic acid phythyl heptanoate graphic file with name molecules-16-01070-i142.jpg LF not stated [84]
Steroids
171 campestrol graphic file with name molecules-16-01070-i143.jpg AP Tanzania [44]
172 phytosterin-B NF NF Taiwan [112]
NF Egypt [86]
173 stigmast-5-en-3-ol β-sitosterol graphic file with name molecules-16-01070-i144.jpg NF Taiwan [91]
AP Tanzania [44]
EP Taiwan [85]
174 β-sitosterol glucoside graphic file with name molecules-16-01070-i145.jpg NF Egypt [86]
175 5α-stigmasta-7-en-3β-ol graphic file with name molecules-16-01070-i146.jpg EP Taiwan [85]
176 5α-stigmasta-7,22t-dien-3β-ol graphic file with name molecules-16-01070-i147.jpg EP Taiwan [85]
177 stigmasta-5,22-dien-3-ol stigmasterol graphic file with name molecules-16-01070-i148.jpg NF Taiwan [91]
AP Tanzania [44]
LF not stated [84]
EP Taiwan [85]
Triterpenes
178 lup-20(29)-en-3-ol lupeol graphic file with name molecules-16-01070-i149.jpg NF Egypt [86]
179 lup-20(29)-en-3-ol, acetate lupeol acetate graphic file with name molecules-16-01070-i150.jpg NF Egypt [86]
180 olean-12-en-3-ol β-amirin graphic file with name molecules-16-01070-i151.jpg NF Egypt [86]
181 5,9,13-trimethyl-24,25,26-trinoroleanan-3-ol friedelan-3β-ol graphic file with name molecules-16-01070-i152.jpg AP Tanzania [44]
182 5,9,13-trimethyl-24,25,26-tri-noroleanan-3-one friedelin; friedelan-3-one graphic file with name molecules-16-01070-i153.jpg AP Tanzania [44]
183 2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene squalene graphic file with name molecules-16-01070-i154.jpg AP Tanzania [44]
LF not stated [84]
EP Taiwan [85]
Tetraterpenes
184 β,β-carotene β-carotene graphic file with name molecules-16-01070-i155.jpg LF not stated [113]
Porphyrins
185 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexa-decen-1-yl ester-(15S,16S)-10-ethenyl-5-ethyl-1,16,18,20-tetrahydro-6,11,15,22-tetramethyl-18,20-dioxo-15H-9,12-imino-21,2-metheno-4,7:17,14-dinitrilo-pyrano[4,3-b]azacyclo-nonadecine-16-propanoic acid aristophyll-C graphic file with name molecules-16-01070-i156.jpg LF Taiwan [90]
186 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl ester-(2S,18S,19S,20bR)-13-ethenyl-8-ethyl-2a,18,19,20b-tetrahydro-20b-(methoxycarbonyl)-9,14,18,24-tetra-methyl-4H-12,15-imino-3,5-metheno-7,10:20,17-dinitrilo-1,2-dioxeto-[3',4':3,4]-cyclo-pent[1,2b]aza-cyclo-nonadecine-19-propanoic acid bidenphytin A graphic file with name molecules-16-01070-i157.jpg LF Taiwan [90]
187 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexa-decen-1-yl ester-(2S,18S,19S,20bR)-13-ethenyl-8-ethyl-2a,18,19,20b-tetrahydro-2a-hydroxy-20b-(methoxy-carbonyl)-9,14,18,24-tetramethyl-4H-12,15-imino-3,5-metheno-7,10:20,17-dinitrilo-1,2-dioxeto[3',4':3,4]-cyclo-pent[1,2-b]-azacyclononadecine-19-propanoic acid bidenphytin B graphic file with name molecules-16-01070-i158.jpg LF Taiwan [90]
188 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl ester-(3R,4S,21R)-14-ethyl-21-hydroxy-21-(methoxycarbonyl)-4,8,9,13,18-penta-methyl-20-oxo-3-phorbinepropanoic acid (132R)-132-hydroxy-pheophytin a graphic file with name molecules-16-01070-i159.jpg LF Taiwan [90]
189 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl ester-(3R,4S,21S)-14-ethyl-21-hydroxy-21-(methoxycarbonyl)-4,8,9,13,18-pentamethyl-20-oxo-3-phorbinepropanoic acid (132S)-132-hydroxy-pheophytin a graphic file with name molecules-16-01070-i160.jpg LF Taiwan [90]
190 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexa-decen-1-yl ester-(3R,4S,21R)-14-ethyl-13-formyl-21-hydroxy-21-(methoxycarbonyl)-4,8,9,18-tetramethyl-20-oxo-3-phorbine-propanoic acid, (132R)-132-hydroxy-pheophytin b graphic file with name molecules-16-01070-i161.jpg LF Taiwan [90]
191 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl ester-(3R,4S,21S)-14-ethyl-13-formyl-21-hydroxy-21-(methoxycarbonyl)-4,8,9,18-tetramethyl-20-oxo-3-phorbine-propanoic acid (132 S)-132-hydroxy-pheophytin b graphic file with name molecules-16-01070-i162.jpg LF Taiwan [90]
192 (2E,7R,11R)-3,7,11,15-tetramethyl-2-hexa-decen-1-yl ester-(3S,4S,21R)-9-ethenyl-14-ethyl-21-(methoxy-carbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid pheophytin a graphic file with name molecules-16-01070-i163.jpg LF Taiwan [90]
Nitrogen and Sulphur-containing Natural Products
193 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione caffeine graphic file with name molecules-16-01070-i164.jpg AP Uganda [110]
194 thymidine graphic file with name molecules-16-01070-i165.jpg NF China [99]
195 1-(2-thienyl)-ethanone 2-acetyl-thiophene graphic file with name molecules-16-01070-i166.jpg RT Germany [122]
Carbohydrates/ disaccharides
196 heptanyl 2-O-β-xylofuranosyl-(1→6)-β-glucopyranoside graphic file with name molecules-16-01070-i167.jpg EP Taiwan [79]
Miscellaneous
197 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione α-tocopheryl quinone graphic file with name molecules-16-01070-i168.jpg EP Taiwan [85]
198 7-O-(4”,6”-diacetyl)-β-D-glucopyranoside NF LF China [59]

AP, Aerial part; LF, Leaf; ST, Steam; EP, Entire plant; FL, Flowers; RT, Root; SD, Seed; LTC, Leaves of tissue culture; PNS, Part not specified; NF, Not found.