Chemical constituents isolated from the roots and rhizomes of Smilacina japonica

Phytochemical investigation of the roots and rhizomes of Smilacina japonica A. Gray led to the isolation of 16 compounds, including six steroidal saponins (1-6), one amide (7), one fatty alcohol (8), one steroidal sapogenin (9), two flavones (10-11), one glycoside (12), one phenol (13), one aliphatic acid (14), and two sterols (15-16). All of these compounds were isolated for the first time from the roots and rhizomes of S. japonica while compounds 1-13 were identified for the first time from the genus Smilacina, of which compounds 9, 11, and 13 were isolated from the Liliaceae family for the first time. Furthermore, the isolation of compound 9 was reported for the first time in plants. Their structures were identified by spectroscopic methods and compared previously published data. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents from Lespedeza cuneata G. Don (Leguminosae)

Phytochemical investigation of Lespedeza cuneata led to the isolation of seventeen compounds including three steroids (β-sitosterol 1, β-sitosterol-6′-linolenoyl-3-O-β-d-glucopyranoside 3, and β-sitosterol glucoside 13), nine flavonoids (quercetin 4, kaempferol 5, isovitexin 8, hirsutrin 9, nicotiflorin 10, vitexin 11, astragalin 12, trifolin 14, and isorhamnetin 17), two phenolics (benzyl-β-d-glucopyranoside 7 and homovanillyl alcohol 16), one carotenoid (loroxanthin 2), one lignin (7R,8S–dihydrodehydrodiconiferyl alcohol 15), and one hexose (pinitol 6) on the basis of their spectroscopic data. Among these compounds, 2, 3, 7, 15 and 16 were reported for the first time from the genus Lespedeza. The taxonomic significance of these isolated compounds was also summarized.     

Phytochemical and chemotaxonomic studies on Pteris wallichiana J. Agardh

A systematic phytochemical investigation of Pteris wallichiana J. Agardh resulted in the isolation of twenty compounds, including five sesquiterpenes (1–5), six flavonoids (6–11), seven phenolic acids (12–18) and two fatty acids (19 and 20). Their structures were deduced from MS, NMR and ORD data. This is the first report of compounds dehydropterosin B (2), (2R,3S)-pterosin C (4), (2R,3R)-pterosin L (5), apigenin (6), luteolin (7), luteolin-7-O-glucoside (10), caffeic acid (13), vanillin (14), 3,4-dihydroxybenzaldehyde (15), chlorogenic acid (17), 3,5-dicaffeoylquinic acid (18), suberic acid (19) and azelaic acid (20) from P. wallichiana and of compounds 15, 19 and 20 from the family Pteridaceae. Furthermore, a chemotaxonomic study of the isolates was performed.     

Chemical constituents from Caragana tangutica

Phytochemical investigation of Caragana tangutica Maxim. resulted in the isolation of ten flavonoids, melilotocarpan A (1), medicarpin (2), maackiain (3), 2-(2′4′-dihydroxyphenyl)-3-methyl-6-methoxy benzofuran (4), cajanin (5), formononetin (6), 7,3′-dihydroxy-5-methoxy isoflavone (7), texasin (8), 2′,4,4′-trihydroxy chalone (9) and bolusanthin III (10), as well as one aromatic acid, p-ethoxy benzoic acid (11). Compounds 1, 4, 9, 10 and 11 were isolated for the first time from the genus Caragana. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the roots of Fallopia multiflora var. Ciliinerve

Phytochemical investigations on the roots of Fallopia multiflora var. Ciliinerve led to the isolation of eighteen compounds, including six chromones [2-methyl-5- carboxymethyl-7-hydroxychromone (1), 2-methyl-5-methylcarboxymethyl-7- hydroxychromone (2), 2,5-dimethyl-7-hydroxychromone (3), 2-methyl-5-hydroxymeth-yl-7-hydroxychromone (4), 2-methyl-5-carboxylicacid-7-hydroxy-chromone (5), and 2,5-dimethyl-7-hydroxychromone-7-O-β-D-glucopyranoside (6)], three lignans [Isolariciresinol (8), 5-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxole (9), and isolariciresinol-9-O-β-D-xylopyranoside (10)], four anthraquinones [physcion-8-O-β-D-glucopyranoside (11), emodin-8-O-β-D-glucopyranoside (12), Rhein (13), and Chrysophanol (14)], three isobenzofurans [5,7-dihydroxy-isobenzofuran (15), 5-methoxy-7-hydroxy-isobenzofuran (16), and 5-methoxy-isobenzofuran-7-O-β-D-glucoside (17)], one phenolic acid [2,5-diacethylhy-droquinone (7)], and one pyran [Zanthopyranone (18)]. Among them, compounds 1, 3, 6, 13 and 14 were reported from F. multiflora var. Ciliinerve for the first time, compounds 2, 8, 10 and 15–17 were isolated from the genus Fallopia for the first time, and compounds 4, 9 and 18 were isolated for the first time from Polygonaceae family. Furthermore, the isolation of compounds 5 and 7 were reported for the first time in plants. Their structures were identified by spectroscopic methods and compared with those previously published. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents from the aerial parts of Ajania fruticulosa

The isolation and identification of sixteen compounds extracted from the aerial parts of A. fruticulosa have been reported in the present study, including eight flavonoids (1, 2, 3, 4, 5, 6, 7 and 8), three terpenoids (9, 10 and 11), two sterols (12 and 13), one lignan (14), one fatty acid (15) and one fatty acid ethyl ester (16), wherein six compounds (2, 3, 4, 5, 10 and 14) have been isolated from A. fruticulosa for the first time. Furthermore, among the identified compounds, three compounds (6, 7 and 11) have also been reported for the first time in the genus Ajanin and three compounds (8, 15 and 16) have not been isolated and reported from other plants of the family Asteraceae. In addition, the chemotaxonomic significance of these compounds was discussed.     

Phytochemical and chemotaxonomic studies on the stems and leaves of Schisandra chinensis (Turcz.) Baill

A comprehensive phytochemical investigation of the stems and leaves of Schisandra chinensis (Turcz.) Baill. resulted in isolation of seventeen compounds, including five lignans: meso-dihydroguaiaretic acid (1), licarin-A (2), pregomisin (3), gomisin A (4), acutissimanide (5), three phenylpropanoids: 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol (6), 2-methoxy-4-(2-propenyl) phenyl β-D-glucopyranoside (7), erigeside 2 (8), six sesquiterpenoids: 7′-hydroxy-abscisic acid (9), burmannic acid (10), (3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (11), 3-Cyclohexene-1,2-diol, 4-(3-hydroxybutyl)- 3, 5, 5-trimethyl- (12), (−)-loliolide (13), (3Z,5R,8R,11R)-Caryophyll-3-ene-5,8,15-triol (14), one monoterpenoid: (6R,3Z)-6,7-dihydroxy-3,7-dimethyl-2-octenoic acid (15) and two other compounds: methyl shikimate (16), 4-Hydroxydodec-2-enedioic acid (17). Their chemical structures were confirmed through NMR, HRESIMS and comparison with the data in the literature. This is the first report of compounds 5, 6, 8–15, 17 from the family Schisandraceae and compounds 2, 16 from the genus Schisandra. Furthermore, we performed a chemotaxonomic study of the separated compounds.     

Chemical constituents from the aerial part of Peganum multisectum

Phytochemical investigation of the aerial part of Peganum multisectum led to the isolation of thirteen compounds, including seven alkaloids (1–5, 7 and 12), two sterols (6 and 10), one phenylpropanoid (8), one lignanoid (11), one megastigman (9), and one phenol (13). Their structures were identified by spectroscopic methods like UV, IR, MS and NMR, and in comparison with the published data in the references. Among them, compounds 10, 12 and 13 were firstly obtained from genus Peganum. The chemotaxonomic significance of these compounds was also discussed, which revealed the relationships between P. multisectum and some other species of genus Peganum.     

Phytochemical constituents of leaves and twigs of Elaeagnus umbellata

A phytochemical study of the leaves and twigs of Elaeagnus umbellata Thunb. has led to the isolation and identification of 12 compounds, including two flavonoid coumaroyl glycosides (1 and 2), two simple phenolic compounds (3 and 4), one coniferyl alcohol derivative (5), one monoterpene (6), two pairs of enantiomeric neolignans (7a/7b and 8a/8b), and a pair of enantiomeric sesquineolignans (9a/9b). The structures of these compounds were elucidated through the analysis of their MS, ECD, and 1D/2D NMR spectra as well as comparison with previously reported data. This is the first time that 1 and 2 have been isolated from this species, and the first time that 5, 6, 7a, 7b, 8a, 8b, 9a, and 9b have been identified in the Elaeagnaceae family.     

Chemical constituents from the roots of Elephantopus scaber L.

A chemical investigation of the roots of Elephantopus scaber L. led to the isolation of thirteen compounds, including four sesquiterpenoids (5, 6, 7, 8), two phenols (1, 2), three triterpenoids (9, 10, 11), two caffeoylquinic acids (3, 4), one alkaloid (12), and one sterol (13). Among these molecules, compound 2 (2-butenoic acid, 3-methyl-[4-(1,5-dimethyl-4-hexenyl)-3-hydroxyphenyl] methyl ester) was identified for the first time from this species, while compounds 1 (curcuphenol) and 12 (patriscabratine) were isolated for the first time from the genus Elephantopus.     

Phytochemical and chemotaxonomic study on Piper pleiocarpum Chang ex Tseng

The phytochemical study of Piper pleiocarpum Chang ex Tseng led to the isolation of eighteen compounds (1–18), including ten lignanoids, galbelgin (1), (+) sesamin (2), denudatin A (3), hancinone (4), (7S,8S, 3′R)-Δ^8'-3,3′,4-trimethoxy-3′,6′-dihydro-6′-oxo-7.0.4′,8.3′-lignan[(2S,3S,3aR)-2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propenyl)-6(2H))-benzofuranone] (5), (−)-(7R,8R)-machilin D (6), (1R,2R)-2-[2-methoxy-4-((E)-prop-1-enyl)phenoxy]-1-(3,4-dimethoxyphenyl)propyl acetate (7), piperbonin A (8), machilin D (9), 4-methoxymachilin D (10), one amide alkaloid, Δ^α,β-dihydropiperine (11), six polyoxygenated cyclohexenes, ent-curcuminol F (12), uvaribonol E (13), ellipeiopsol A (14), 1S,2R,3R,4S-1-ethoxy-2-[(benzoyloxy)methyl]cyclohex-5-ene-2,3,4-triol, 3-acetate (15), (+)-crotepoxide (16), (+)-senediol (17), and one benzoate derivative, 2-acetoxybenzyl benzoate (18). Their structures were established by spectroscopic data and by comparison with the literature. All the compounds were firstly isolated from P. pleiocarpum, while ten compounds 6–7, 9–10, 12–15, 17–18 were isolated from the genus Piper and the family Piperaceae for the first time. The chemotaxonomic significance of these compounds was also discussed. The isolation of compounds 6–7, 9–10 may be used as chemotaxonomic markers for the genus of Piper.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

Chemical constituents from the aerial sections of Ajania potaninii

Nineteen compounds were isolated from Ajania potaninii, including one sulfur paraffin (1), one monoterpene (6), one lactone (3), one aliphatic acid (15), two sterols (8 and 10), one triterpenes (13), one alkaloid (18), eleven flavonoids (2, 4, 5, 7, 9, 11, 12, 14, 16 and 17) and one cyclic amide (19). All of these compounds were obtained from A. potaninii for the first time. This is the first report of N-nonanemercaptan (1), 3-hydroxy-5-decanolide (3), cirsiliol (5), 1,2,4-trihydroxy-p-mentane (6), 6-methoxytricin (7), eriodictyol (11), pectolinarigenin (12), 3,3′-di-O-methylquercetin (14), tetradecanoic acid (15), lappaconitine (18) and 1,1′,1″,1‴,1‴'-tricontane lactam (19) from the genus Ajania. The occurrence of compounds 18 and 19 in A. potaninii warrants further study.     

Phytochemical investigation of Millettia dorwardi Coll. et Hemsl

The first phytochemical investigation on the vine stems of Millettia dorwardi Coll. et Hemsl led to the isolation of ten flavonoids (isoafrormosin 1, formononetin 2, afrormosin 3, padmakastein 4, liquiritigenin 5, 4H-1-Benzopyran-4-one,7-hydroxy-5,8-dimethoxy-3-(4-methoxyphenyl)-isoflavone 6, 4H-1-Benzopyran-4-one,7-hydroxy-3-(3-hydroxy-5-methoxyphenyl)-6-methoxy 8, 4H-1-Benzopyran-4-one,6-methoxy-3-(4-methoxyphenyl)-6,4′-dimethoxyisoflavone 9, irisolidone 10, prunetin 11), one heterocycle (5-5′-dibuthoxy-2-2′-bifuran 7) and one new isoflavone glycoside (4H-1-Benzopyran-4-one,5-hydroxymethyl-3-(4-methoxyphenyl)-6-β-d-glucopyranoside-isoflavone 12). Their structures were determined by extensive analysis of their spectroscopic data. Among them, compounds 4, 6–10, 12 were for the first time isolated from this genus. The chemotaxonomic importance of these compounds was also summarized.     

Chemical constituents from the fruits of Rhus typhina L. and their chemotaxonomic significance

This work describes the isolation and characterization of twenty-nine compounds from the fruits of Rhus typhina L., including eleven flavonoids (1–11), eleven phenols (12–22), two pentacyclic triterpenes (23–24), two organic acids (25–26), one lumichrome (27), one courmarin (28) and one pyrimidine (29) on the basis of their spectroscopic data. Compounds apigenin (1), daidzein (4), orobol (5), 3′, 5, 5′, 7-tetrahydroxyflavanone (6), naringenin (7), butein (8), (-)-catechin (9), quercetin-3-O-α-L-(3″-O-galloyl)-rhamnoside (11), 2-hydroxybenzoic acid (13), 4-hydroxybenzaldehyde (14), vanillin (15), methyl 3,4-dihydroxybenzoate (16), 3,5-dihydroxybenzamide (18), tyrosol (19), caffeic acid (20), 3-(2,4,6-trihydroxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one (21), phlorizin (22), friedelin (23), oleanolic acid (24), 4,4-dimethyl-heptanedioic acid (25), anthranilic acid (26), lumichrome (27), scoparone (28) and uracil (29) have not been recorded before in this plant. This is the first report on the occurrence of compounds 4–7, 9, 11, 13–14, 16, 18–21, 25–29 from the genus Rhus. Moreover, the chemotaxonomic significance of these isolated compounds was also summarized.     

Chemical constituents from Laggera pterodonta

A phytochemical investigation on the aerial parts of Laggera pterodonta resulted in the isolation and identification of fourteen compounds, including six sesquiterpenoids (1–6), five flavonoids (7–11), one lignan (12), and two pyrrole alkaloids (13, 14). Among them, compounds 1–3, 7–9, and 11 are the characteristic class of secondary metabolites of L. pterodonta. Compounds 4 and 5 were firstly isolated from L. pterodonta and this is the first report of the presence of compounds 6, 10, and 12 from the genus Laggera. Pyrrole alkaloids 13 and 14 may serve as potential chemotaxonomic markers for L. pterodonta and could be used to distinguish among species of Compositae.     

Phytochemical and chemotaxonomic study on Pholidota pallida lindl

Phytochemical investigation of Pholidota pallida Lindl. led to the isolation of eleven compounds 1–11 (coelonin 1, lusianthridin 2, flavanthrin 3, batatasin-Ⅲ 4, 3′,5-dihydroxy-2-(4-hydroxybenzyl)-3-methoxybibenzyl 5, gigantol 6, 3-[2-(3-hydroxyphenyl) ethyl]-2,4-bis[(4-hydroxyphenyl) methyl]-5-methoxyphenol 7, hydroxytyrosyl butyrate 8, (24R)-ethylcholest-5-en-3-ol-7-one 9, taraxerone 10, friedelin 11) including three phenanthrenes 1–3, four bibenzyls 4–7, one hydroxytyrosyl 8, one steroid 9 and two terpenoids 10–11. The structures of these compounds were elucidated by spectroscopic analyses. This is the first report of isolation of compounds 1–11 from Pholidota pallida and compounds 5 and 8–11 within genus Pholidota. Compound 8 is a new natural product, isolated from a natural source for the first time. Furthermore, the chemotaxonomic significance of the isolates was also discussed.     

Phytochemical and chemotaxonomic study on Berchemiella wilsonii (Schneid.) Nakai

Phytochemical investigation of the aerial parts of Berchemiella wilsonii (Schneid.) Nakai (Rhamnaceae) led to the isolation of four flavonoids (1–4), three phenolic acids (5–7), two megastigmane derivatives (8–9) and one triterpene (10). The structures of these compounds were elucidated as taxifolin (1), (−)-epicatechin (2), quercetin 3-O-a-l-arabinopyranoside (3), vitexin (4), methyl p-hydroxycinnamat (5), 3,4-dihydroxybenzoic acid (6), 2-hydroxy-4-methoxy-3,6-dimethyl benzoic acid (7), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (6S,9R)-roseoside (9) and lupeol (10) on the basis of NMR spectral data and comparison with literature values. These results are the first chemical constituent data of the genus Berchemiella, and the chemotaxonomic significance of these compounds is discussed.     

Renoprotective chemical constituents from an edible mushroom,Pleurotus cornucopiae in cisplatin-induced nephrotoxicity

Pleurotus cornucopiae (Pleurotaceae) is an edible and medicinal mushroom widely distributed in Korea, China, and Japan. The MeOH extract of the fruiting bodies of P. cornucopiae showed renoprotective effects against cisplatin-induced kidney cell damage. Chemical investigation of the MeOH extract led to the isolation and identification of 12 compounds including noransine (1), uridine (2), uracil (3), (3β, 5α, 6β, 22E, 24S) -ergosta-7, 22-diene-3, 5, 6, 9-tetrol (4), (22E,24S)-ergosta-7,22-diene-3β,5α,6β-triol (5), (22E,24R)-ergosta-8(14),22-diene-3β,5α,6β,7α-tetrol (6), cerebroside B (7), (2R) -N- [(1S, 2R, 3E, 7E) -1- [(β-d-glucopyranosyloxy) methyl] -2-hydroxy-8-methyl-3, 7-heptadecadien-1-yl] -2-hydroxy-heptadecanamide (8), cerebroside D (9), nicotinamide (10), 1,2-bis(hydroxymethyl)-4,5-dimethoxybenzene (11), and benzoic acid (12). Among them, compounds 1 and 11 were isolated as naturally occurring products for the first time, though they were reported as synthetic products in previous papers. All of the compounds (except 8 and 11) abrogated cisplatin-induced LLC-PK1 cell damage in a dose-dependent manner. Of special note, compounds 2, 5, 6, and 12 ameliorated cisplatin-induced nephrotoxicity to 80% of the control value at 10 μM. The protective effects of compounds 2, 5, 6, and 12 were mediated via the deactivation of JNK-caspase 3 apoptotic cascade. This study is the first to demonstrate that the chemical constituents of P. cornucopiae display renoprotective effects against anticancer drug-induced damage in kidney cells.     

Chemical constituents from Anemone vitifolia Buch.-Ham. (Ranunculaceae)

A phytochemical investigation of Anemone vitifolia (Buch.-Ham.) led to the isolation of twelve compounds, including six lignans (1–6), four benzoic acid esters (7–10), one norsesquiterpenoid (11) and one lactone (12). The structures of these metabolites were established on the basis of detailed spectroscopic analysis, as well as comparisons with the data available in the literature. Among them, compounds 10 (dimethyl 2-(benzoyloxy)succinate) and 12 (4-hydroxy-5-methyl-γ-butyrolactone) were isolated for the first time as natural products. Compounds 1 and 11, compounds 2, 3, 5–7 and 9, and compounds 4 and 8 were isolated for the first time in family Ranunculaceae, genus Anemone and A. vitifolia respectively. The chemotaxonomic significance of the isolated compounds was discussed.