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

Compilation of Secondary Metabolites from Bidens pilosa L

Fabiana Lima Silva 1,2,*, Dominique Corinne Hermine Fischer 2, Josean Fechine Tavares 1, Marcelo Sobral Silva 1, Petronio Filgueiras de Athayde-Filho 1, Jose Maria Barbosa-Filho 1,*
PMCID: PMC6259624  PMID: 21270729

Abstract

Bidens pilosa L. is a cosmopolitan annual herb, known for its traditional use in treating various diseases and thus much studied for the biological activity of its extracts, fractions and isolated compounds. Polyacetylenes and flavonoids, typical metabolite classes in the Bidens genus, predominate in the phytochemistry of B. pilosa. These classes of compounds have great taxonomic significance. In the Asteraceae family, the acetylene moiety is widely distributed in the Heliantheae tribe and some representatives, such as 1-phenylhepta-1,3,5-triyne, are noted for their biological activity and strong long-wave UV radiation absorbance. The flavonoids, specifically aurones and chalcones, have been reported as good sub-tribal level markers. Natural products from several other classes have also been isolated from different parts of B. pilosa. This review summarizes the available information on the 198 natural products isolated to date from B. pilosa.

Keywords: Bidens pilosa, Asteraceae, natural products, flavonoids, polyacetylenes

Introduction

The genus Bidens (Asteraceae: Heliantheae) comprises about 240 species with cosmopolitan distribution [1]. Many of these species have been investigated chemically to contribute to the classification of Asteraceae [2,3,4]. Interesting relationships within the Heliantheae, as well as its relationship with other tribes have been proposed on the basis of various types of compounds found in the tribe, especially acetylenes, sesquiterpene lactones and flavonoids [4,5]. The interest in these classes of compounds also has gone beyond chemotaxonomy. The biological activities, including antiparasitic, antifungal and antioxidant properties, of the predominant components in the tribe Heliantheae have been widely reported, and the investigation of these species for the discovery of new active compounds has expanded [6,7,8,9,10,11,12].

Bidens pilosa L. (Figure 1) stands out among the species of the genus due to the large number of natural products characterized in it and the biological activities reported for its extracts, fractions and compounds. Therefore, in continuation of our research on bioactive molecules from the various species of the different families cited [13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43], we offer this compilation of the chemical constituents of B. pilosa.

Figure 1.

Figure 1

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Bidens pilosa L.

Bidens pilosa L.

B. pilosa is an annual, erect and ruderal herb originating from South America and now found in almost all tropical and subtropical region countries [44,45,46]. It grows to a height of up to 1.5 m, branching from the base and its yellow flowers have 5-15 mm diameter [44,46].

It is a cosmopolitan herb, considered invasive of annual and perennial crops and widely distributed in disturbed areas and along roadsides in tropical and subtropical climates [46]. Nevertheless, this plant is commonly used in the traditional medicine. In Martinique, the decoction of the whole plant is used for its anti-inflammatory and hypoglycemic effects [47]. Aqueous preparations of the leaves are used by Zulu people for the treatment of dysentery, diarrhea and colic [48]. B. pilosa has been popularly used in China as a herbal tea ingredient or in traditional medicine for treating various disorders, such as diabetes, inflammation, enteritis, bacillary dysentery and pharyngitis [49]. In Brazil, it is widely used as a folk medicine by indigenous people to treat a variety of illnesses including pain, fever, angina, diabetes, edema, infections and inflammation [50,51]. In addition, in the Amazon and regions in the South of Brazil, hydroalcoholic solutions of B. pilosa roots are also regarded as useful in the treatment of malaria [52] and even tumors [53].

Studies of B. pilosa plant extracts have shown it has anti-hyperglycemic [54,55], antihypertensive [56,57,58], antiulcerogenic [45], hepatoprotective [59], antipyretic [60], immunosuppressive and anti-inflammatory [8,61,62], anti-leukemic [63,64], anti-malarial [50], anti-bacterial [48], antioxidant [65,66] and antitumor [67] effects. These proven biological activities have led countries like Brazil to include B. pilosa in the official list of medicinal plants with potential for development of herbal use by the public health system [68].

Because the biological activities of some extracts and fractions obtained from different parts of B. pilosa, several isolated constituents of the plant have been studied, referring to anti-inflammatory activity, immunosuppressive [44,49,61,69,70], hepatoprotective [59], anti-bacterial [44,71], antifungal [71] anti-malarial [50,71,72], anticancer [72], antiparasitic [73], anti-hyperglycemic activities [49,54,70,74,75,76], anti-angiogenic [77,78], antioxidant [79] and cercaricidal [80].

The Phytochemistry of Bidens pilosa L.

B. pilosa has been extensively studied since the early 1900s. Among the classes of compounds reported polyacetylenes and flavonoids, typical metabolite classes in the Bidens genus, predominate [4,81]. These are also the most reported classes of compounds when referring to the biological activities [49,50,54,61,74,75,82,83]. A number of earlier studies also have reported the isolation of sterols [44,84,85], terpenoids [46,85,86], phenylpropanoids [62,83,87,88,89,90] and hydrocarbons [44,85,91].

There have been a few reviews of B. pilosa [6,51,92,93], however the phytochemical data have not included all classes of metabolites. To date almost 198 compounds have been described from this species. These secondary metabolites are listed in Table 1, where they were grouped based on the classification adopted by a standard reference work, the Dictionary of Natural Products [94].

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]
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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.

The order begins with the structurally most simple metabolites, derived from aliphatic natural produts (branched, unbranched, saturated or unsaturated hydrocarbons), and among these, the acetylenes are highlighted. Next the derivatives of simple aromatic hydrocarbons and the phenylpropanoids, in which a C3 substituent is attached to the aromatic unit (C6), form a biosynthetically distinct group of aromatic metabolites. The flavonoids, also considered a large group of metabolites in B. pilosa are subdivided into aurones, chalcones, flavanones, flavones and flavonols. The terpenoids group is divided according to the number of carbons, starting in sesquiterpenes and continuing with diterpenes, sterols, triterpenes and finally tetraterpenes. Finally, porphyrins, nitrogen and sulphur-containing natural products, one disaccharide and miscellaneous compounds are arranged.

Acetylene compounds

The acetylenes are one class of aliphatic hydrocarbons that has a taxonomically interesting distribution pattern in higher plant families; they occur regularly in only five families, namely the Campanulaceae, Asteraceae, Araliaceae, Pittosporaceae and Umbelliferae [95]. Within the Asteraceae family, these compounds are widely distributed in the Heliantheae tribe [2,4]. The genus Bidens is known to produce compounds of this class [5]. They occur in all parts of the plant, often accumulating in roots [96].

To date 34 acetylenes (compounds 35–68) were isolated from B. pilosa (Table 1). The C13-polyacetylenes are the most abundant in the species and among them, ene-tetryn-ene 36 and its alcohol, acetyl and aldehyde oxygenated derivatives 40–42, C13-phenylacetylenes 59–66 and C13-acetylenes with an ene-triyn-diene chromophore 39 are typical constituents within the genus Bidens [2,4,96,97].

The principal representative of the C13-polyacetylenes is 1-phenylhepta-1,3,5-triyne (64). This C13-phenylacetylene is abundant in B. pilosa and is present in leaves, stems and roots of the species [5,73,96,97]. The compound is biologically active and several studies have reported that it strongly absorbs long-wave UV radiation, and the activity is altered upon exposure to light (photo activation) [98].

The occurrence of C17-acetylenes is rare in the genus, being limited to the Hawaiian species of Bidens [4], while one compound (35) was related to B. pilosa grown in China [2,99]. Also, three C14-acetylenes 39,44,46, with one (46) being common in species of genus Coreopsis, and another (44), a new compound, were reported first in B. pilosa [4,51,100].

Another group of polyacetylenes isolated from B. pilosa are the polyacetylene glucosides (PAGs), which are glycosides of polyacetylenes in which a sugar moiety (glycose or rhamnose) is joined to a polyacetylene through an -O- glucosidic linkage. Of even more restricted distribution, these have been reported for only two families, Asteraceae and Campanulaceae. So far 22 PAGs are known, however most of them have been isolated from Bidens species [101].

Studies report the isolation of nine PAGs (50–58) from different parts from B. pilosa. Four compounds (50, 53–55) have the common C13-acetylene linkage to glycoside portion in the C2 position [49,54,61,102], however the glycoside derivates of C14-acetylene have the linkage to the glycoside portion in the terminal portion (52) and C3 (51) [53,54]. Other unusual three PAGs have also been reported for B. pilosa. Two C16-acetylenes (56,57) and one C17-acetylene (58) having an ester in the terminal portion linkage to a carboxylic acid [70].

Phenylthiophenes, classified as C13-acetylene and related compounds [4], are related to only occur in Coreopsis and in Hawaiian Bidens [4,103], however a phenylthiophene 67 and its glycosylate 68 were reported for B. pilosa growing in China [100].

Flavonoids

Flavonoids are the class of compound of higher occurrence in the species and are described as chemotaxonomic markers at lower hierarchical levels of the Asteraceae [104]. According to the Bidens genus, the flavonoid profile of B. pilosa is a complex one that includes aurones, chalcones, flavanones, flavones and flavonols with a wide variety of O-methylation patterns and glycosylations [105], totaling 58 different compounds isolated to date (Table 1).

Anthochlors (aurones and chalcones) are found in a number of plant families, including the Asteraceae. However research indicates that, despite some variations, anthochlors are good markers for the taxonomic subtribe Coreopsidinae (Heliantheae tribe), thus representing the only case in the family Asteraceae in which a certain type of flavonoid is taxonomically diagnostic at the sub tribal level [106].

Species of Bidens typically contain the chalcones butein (3,4,3’,4’-tetrahydroxychalcone, 112), okanin (3,4,2’,3’,4’-pentahydroxychalcone, 113) and their 4’-glycosides [3]. Of the aurones, maritimetin (6,7,3',4'-tetrahydroxyaurone, 102) and sulfuretin (6,3',4'-tetrahydroxyaurone, 101) and their glycosides are commonly found in the genus [107]. These compounds have been reported for B. pilosa [108].

In B. pilosa, the glycosides aurones are frequent in position 6 (103–110) and rare in 7 (104) while the glycosides derived from chalcones (111,114–128)are in the positions 3’ and 4’. Two chalcone glycosides, one in position 2’ (111) and other in 4 (128) were also found to the specie [59,102]. Most of these compounds are acylated with p-coumaric and/or acetic acid on the sugar moiety and are relatively non-polar; however more polar aurones (103,104) and chalcones (111,114,115,124,128), mono- and diglucosides were isolated from aerial parts [109]. Two B-ring methylated chalcones (126–127) [80,100] were also found in the species, but this kind of derivatives is rarely reported in the Bidens genus [3].

Flavones and flavonols identified from members of Bidens are for the most part commonly encountered compounds, i.e., glycosides of apigenin, luteolin, kaempferol and quercetin [105]. B. pilosa maintains that standard, however some flavonols present methoxy substitutent groups at their positions 3, 6, 7, 3’ and/or 4’, as in jacein (149), centaureidin (139) and its glycoside centaurein (140) [74,79]. Among the flavones 5-O-methylhoslundin (135) was reported, a compound previously isolated only from Hoslundia opposite (Lamiaceae) [110]. This unusual compound presents methoxy substituted groups in C5 and C7 and a pyranone derivative at C6.

Other compound classes

Several other compound classes have been isolated from different parts of B. pilosa and are listed in Table 1. Among these, aliphatic hydrocarbon derivatives and simple aromatic hydrocarbons have been reported, although these constituents are rather ubiquitous in plants.Long chain saturated unbranched hydrocarbons between C21 and C33 (1–13) have been isolated of B. pilosa [44,91]. Of the saturated unbranched alcohols, the compound 2-butoxyethanol (14) is the only ether-ethanol, while for the unbranched aliphatic carboxylic acid and ester group, three compounds have ether-ester functions (32–34). The simple aromatic hydrocarbons and simple phenylpropanoid compounds form two small groups of natural products in B. pilosa. In the first, vanillic (80), salicylic (78) and protocatechuic (79) acids and their derivatives are predominant [87], while the phenylpropanoids are represented by coumaric (82), ferulic (84) and caffeic (85) acid. In this group, one new disubstituted acetylacetone (86) was described for B. pilosa growing in India [90].

Also in the phenylpropanoids group, caffeoyl ester derivatives 87–97 are fairly reported for the specie, and some esters formed by the combination of two caffeic acids to one quinic acid (93–97) [79,83] or one caffeic acid to one erythronic acid (88–92) [88]. The only coumarin (100) described for B. pilosa is usually found in other species of the family [86].

Of the mevalonate pathway, several sesquiterpenes (160–167), sterols (171–177) and triterpenes (178–183) have been isolated of leaves from B. pilosa [44,51,86]. The sesquiterpenes reported were characterized by GC-MS [46]. These are divided into mono- and bicyclic, commonly found in leaf extracts from Asteraceae. In the diterpenes, acyclic phytane diterpenoids have been reported; among them phytyl heptanoate (170) is an unusual compound that has an aliphatic chain of seven carbon atoms linked to the terminal acid portion [84].

The most abundant sterols from B. pilosa are stigmasterol (177) and sitosterol (173), which are ubiquitous compounds of plant cell membranes [111]. Stigmasterol derivates (175,176), sitosterol glucoside (174) [85,91] and phytosterin B (172), a phytosterin first isolated in B. pilosa [112] has also been reported. Among the triterpenes, only squalene (183) is an acyclic one. The friedelanes 181,182 and lupeol derivatives 178, 179 are the more common triterpenes reported for B. pilosa [44,86]. Among the tetraterpenes β-carotene (184) is reported to be present in high concentration in young leaves of B. pilosa [113].

Chlorin (=2,3-dihydroporphyrin) and its derivatives – including chlorophyll, pheophytin, chlorophyllin, pheophobide, and many other closely related analogues – are found in most higher plants, algae, and even bacteria [114]. For B. pilosa two new pheophytins (186,187), with peroxide functionalities in ring E were reported, besides another six pheophytins (185,188–192), already known [114].

Only two representatives of the class of nitrogen-containing natural products, one being the nucleoside thymidine (194) are reported [122]. One thyophene (195) was reported from B. pilosa [99]. One disaccharide (196) was isolated from an entire B. pilosa. Also, two miscellaneous representatives were reported, a quinone linked to an aliphatic chain (197) [85] and one compound of unidentified structure (198) [59].

The content of essential oil from flowers, leaves and stems of B. pilosa has been analyzed by GC-MS in China, Japan, USA, Cameroon, Nigeria and Iran [66,115,116,117,118,119,120,136]. In this review, the series of components identified as being commonly found in plants containing essential oils and present mostly in very small quantities are not listed. It is then just a brief comment about the main and unusual constituents. In the species a series of mono- and sesquiterpenes have been detected [66,116,117,118,119]. The major constituents are the sesquiterpenes germacrene-D and β-caryophyllene. Polyacetylenes (36,59,60,64), including 1-phenylhepta-1,3,5-tryin (64) have been identified in root oil and aerial parts [117,119]. A chromone, known as precocene I, isolated from oil of the leaves from B. pilosa also was reported [116].

Acknowledgements

The authors are grateful to CNPq/RENORBIO and CAPES/Brazil for financial support and research fellowships.

Footnotes

Sample Availability: Not available.

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