Chemical Constituents from Fructus Xanthii*

Traditional Uses, Botany, Phytochemistry, Pharmacology, Pharmacokinetics and Toxicology of Xanthium strumarium L.: A Review

“…Moreover, xanthinin ( 11 ), xanthumin ( 12 ), xanthanol ( 13 ), xanthanol acetate ( 14 ), isoxanthanol ( 13 ), xanthumanol ( 16 ), deacetoxylxanthumin ( 17 ), xanthatin ( 18 ), xanthinosin ( 19 ), tomentosin ( 20 ) were isolated from the leaves of X. strumarium [15,16]. Furthermore, other sesquiterpenoids were isolated and identified from the fruits, leaves and aerial parts of X. strumarium , including 8-epi-tomentosin ( 21 ) [17], 11α,13-dihydroxanthuminol ( 22 ), desacetylxanthanol ( 23 ) [18], (2E,4E,1’S,2’R,4’S,6’R)-dihydrophaseic acid ( 24 ) [19], 8-epi-xanthatin ( 25 ) [20], 2-hydroxy xanthinosin ( 26 ) [21], lasidiol p -methoxybenzoate ( 27 ) [18], 1β,4β, 4α,5α-diepoxyxanth-11(13)-en-12-oic acid ( 28 ), 11α,13-dihydroxanthatin ( 29 ), 4β, 5β-epoxyxanthatin-1α,4α-endoperoxide ( 30 ), 4-epi-xanthanol ( 31 ), 4-epi-isoxanthanol ( 32 ), 4-oxo-bedfordia acid ( 33 ) [22], 2-hydroxytomentosin ( 34 ), 2-hydroxytomentosin-1β,5β-epoxide ( 35 ) [20], xanthnon ( 36 ) [21], 6β,9β-dihydroxy-8-epi-xanthatin ( 37 ) [25], inusoniolide ( 38 ) [21], (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmene-9-one ( 39 ) [24], pungiolide E ( 40 ), pungiolide A ( 41 ), pungiolide D ( 42 ) [25], 5-azuleneacetic acid ( 43 ) [21], dihydrophaseic acid sodium salt 4’-O-β -d- glucopyranoside ( 44 ) [26], (3S,5R,6R,7E,9S)-megastigman-7ene-3,5,6,9-tetrol-3-O-β -d- glucopyranoside ( 45 ) [27].…”

“…However, studies have shown that factors such as origin, harvesting time, processing time and temperature have obvious effects on the content of phenolic acid in X. strumarium [58]. Thirteen caffeoylquinic acids (CQA) derivatives were isolated from X. strumarium , including 1,3,5-tri- O -caffeoylquinic acid ( 55 ), 3,5-di- O -caffeoylquinic acid ( 56 ), neochlorogenic acid methyl ester ( 57 ), 1,3-di- O -caffeoylquinic acid ( 58 ), methyl-3,5-di- O -caffeoylquinic acid ( 59 ), chlorogenic acid ( 60 ), 1,4-di- O -caffeoylquinic acid ( 61 ), 4,5-di- O -caffeoylquinic acid ( 62 ), 5- O -caffeoylquinic acid ( 63 ), 1,5-di- O -caffeoylquinic acid ( 64 ), 3,4-di-caffeoylquinic acid methyl ester ( 65 ), 3,5-di-caffeoylquinic acid methyl ester ( 66 ), 4- O -caffeoyl quinic acid methyl ester ( 67 ) [33,34,35,36,37,38]. In addition, in 2017, N-trans-feruloyl tyramine ( 68 ) and 9,9’- O -di-(E)-feruloyl-(-)-secoisolariciresinol ( 69 ) were firstly reported in this plant [39].…”

“…Besides, some other phenylpropanoids were also isolated and identificated from this plan, such as xanthiumnolic A ( 70 ), xanthiumnolic C ( 71 ) [40], 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one ( 72 ) [41], threo-guaiacylglycerol-8- O -4’-(coniferyl alcohol) ether ( 73 ), erythro-guaiacylglycerol-8- O -4’-(coniferyl alcohol) ether ( 74 ), threo-1-phenyl-(4-hydroxy-3-methoxy)-2-phenyl-(4’’-hydroxy-3’’-methoxy)-1,3-propanediol ( 75 ), (1S,2R)-1,2-bis(4-hydroxy-3- methoxyphenyl)-1,3-propanediol ( 76 ), threo-guaiacylglycerol-β-coniferyl aldehyde ether ( 77 ), erythro-guaiacylglycerol-β-coniferyl aldehyde ether ( 78 ) [42], xanthiumnolic D ( 79 ), xanthiumnolic E ( 80 ) [40], ferulic acid ( 81 ) [43], caffeic acid ( 82 ) [36], protocatechuic acid ( 83 ) [19], isovanillic acid ( 84 ) [30], 7-(4-hydroxy-3-methoxyphenyl)-1-phenylhept-4-en-3-one ( 85 ) [28], xanthiazone-(2- O -caffeoyl)-β -d- glucopyranoside ( 86 ) [44], rel-(2α,3β)-7- O -methylcedrusin ( 87 ) [42], caffeic acid choline ester ( 88 ) [38], icariside D1 ( 89 ) [45], 3-methoxy-4-hydroxy-transcinnamaldehyde ( 90 ) [24], methylchlorogenate ( 91 ) [46], icariside F2 ( 92 ), arbutin ( 93 ), coniferine ( 94 ) [45], 3-hydoxy-1-(4-hydroxy-phenyl)-propan-1-one ( 95 ) [47], ω-hydroxypropioguaiacone ( 96 ) [45], caffeic acid ethyl ester ( 97 ) [19], 4-hydroxy-3-methoxycinnamaldehyde ( 98 ) [37], p-hydroxybenzaldehyde ( 99 ) [24], The chemical structures of these phenylpropenoids isolated from X. strumarium are shown in Figure 4.…”

Phytochemical analysis on quantification and the inhibitory effects on inflammatory responses from the fruit of xanthii fructus

“…Among these components, chlorogenic acid and 1,5-dicaffeoylquinic acid were detected as the main constituents (33.56 mg/g and 10.12 mg/g) of X. fructus . Protocatechuic acid and ferulic acid, which have been isolated and analyzed as bioactive compounds from X. fructus ,[ 2 14 15 ] were not detected in this sample.…”

Phenolic Compounds from the Aerial Parts of Malva verticillata and their Anti-diabetic Effect

“…Four phenolic compounds were isolated and identified from the M. verticillata and evaluated for their effects on alloxaninduced PI damage in zebrafish. Four phenolic compounds-benzyl--D-galactopyranoside (1) [16], (-)-secoisolariciresinol-9′-O--D-glucopyranoside (2) [17], transferulic acid (3) [18], and trans-ferulic acid methyl ester (4) [19] were identified by comparison of spectroscopic data with those of the literature. Compound 1 has never been previously isolated from natural sources, but it was previously synthesized using the Fischer method [16].…”