Steroidal constituents of Solanum xanthocarpum

From the extract of the fruits of Solanum xanthocarpum (Solanaceae), five new steroidal compounds were isolated and characterized: 4α-methyl-24ξ-ethyl-5α-cholest-7-en-3β,22ξ-diol (1), 3β,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (2), 3β-benzoxy-14β,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (3), 3β-benzoxy-14α,22ξ-dihydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (4) and 3β-(p-hydroxy)-benzoxy-22ξ-hydroxy-4α-methyl-24ξ-ethyl-5α-cholest-7-en-6-one (5).     

Further constituents of Galianthe thalictroides (Rubiaceae) and inhibition of DNA topoisomerases I and IIα by its cytotoxic β-carboline alkaloids

A new cytotoxic β-carboline alkaloid, 1-methyl-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol (1), was isolated from roots of Galianthe thalictroides, together with the alkaloid 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol (2), the anthraquinones 1-methyl-alizarin and morindaparvin-A, the coumarin scopoletin, homovanillic alcohol, (−)-epicatechin, and the steroids stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, 6-β-hydroxy-stigmast-4-en-3-one, stigmasterol, campesterol, β-sitosterol, and β-sitosterol-3-O-β-d-glucopyranoside. Among the previously known compounds, homovanillic alcohol is a novel finding in Rubiaceae, while 1-methyl-alizarin, morindaparvin-A, scopoletin, stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, and 6-β-hydroxy-stigmast-4-en-3-one is reported for the first time in the genus Galianthe. The cytotoxic β-carboline alkaloids 1 and 2 exhibited potent antitopoisomerase I and IIα activities and strong evidence is provided for their action as topoisomerase IIα poisons and redox-independent inhibitors.     

Phytochemical investigation of Eremostachys moluccelloides Bunge (Lamiaceae)

Phytochemical investigation of the aerial parts of Eremostachys moluccelloides Bunge led to the identification of a new diterpene, 2β,14-dihydroxy −11-formyl- 12-carboxy-13-des-isopropyl-13-hydroxymethyl-abieta-8,11,13- triene- 16(17)- lactone (1), along with the known compounds 12, 18-dicarboxy-14-hydroxy-13-des -isopropyl-13-hydroxymethyl- abieta-8,11,13-triene-16(17)-lactone (2), 5-hydroxy-3′,4′,7-trimethoxyflavone (3), 5-hydroxy-4’,7-dimethoxyflavone (4), luteolin-7-O-β-glucoside (5), verbascoside (6), luteolin 7-O-(6″-O-β-D-apiofuranosyl) -β-D-glucopyranoside (7), chlorogenic acid (8), echinacoside (9), apigenin-7-O-β-D-glucoside (10), p-coumaric acid (11), vanillic acid (12), apigenin-7-O-(6″-E-p-coumaroyl)-β-D-glucopyranoside (13), apigenin-7-O-(3″,6″-E-p-dicoumaroyl)-β-glucoside (14), lamalbide (15), 6β-hydroxy-7-epi-loganin (16), phloyoside II (17) The structures were elucidated on the basis of 1D and 2D NMR spectroscopy, UV, MS and by comparison with compounds previously reported in the literature. Compounds 1–4, 8, 9, 11, 12, 14 have not been reported previously from any species within the genus Eremostachys. Compounds 1–14, 17 were obtained from this species for the first time. The chemotaxonomic significance of the isolated compounds is 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.     

Cucurbitane-type triterpenoids from the aerial parts of Momordica charantia L.

Six new cucurbitane-type triterpenoids (1–6), together with two known analogues (7 and 8) were isolated from the aerial parts of Momordica charantia L. The structures of new compounds were identified as cucurbita-6,24-dien-3β,23-diol-19,5β-olide (1), (19R)-5β,19-epoxy-19-methoxycucurbita-6,24-dien-3β,23-diol (2), (19S)-5β,19-epoxy-19-methoxycucurbita-6,24-dien-3β,23-diol (3), (19R)-5β,19-epoxy-19-isopropoxycucurbita-6,24-dien-3β,23-diol (4), 3β,23-dihydroxy-5-methoxycucurbita-6,24-dien-19-al (5) and (19R)-7β,19-epoxy-19-methoxycucurbita-5,24-dien-3β,23-diol (6), by extensive MS, 1D and 2D NMR spectroscopic technologies. This is the first report of the isolation of tetracyclic triterpenoids possessing a 7β,19-epoxy system, viz., 6, from M. charantia L.     

Bioactive constituents of Helianthus tuberosus (Jerusalem artichoke)

In a cytotoxicity-guided study using the MCF-7 human breast cancer cell line, nine known compounds, ent-17-oxokaur-15(16)-en-19-oic acid (1), ent-17-hydroxykaur-15(16)-en-19-oic acid (2), ent-15β-hydroxykaur-16(17)-en-19-oic acid methyl ester (3), ent-15-nor-14-oxolabda-8(17),12E-dien-18-oic acid (4), 4,15-isoatriplicolide angelate (5), 4,15-isoatriplicolide methylacrylate (6), (+)-pinoresinol (7), (?)-loliolide (8), and vanillin (9) were isolated from the chloroform-soluble subfraction of a methanol extract of the whole plant of Helianthus tuberosus collected in Ohio, USA. This is the first time that diterpenes have been isolated and identified from this economically important plant. The bioactivities of all isolates were evaluated using the MCF-7 human breast cancer cell line as well as a soybean isoflavonoid defense activation bioassay. The results showed that two germacrane-type sesquiterpene lactones, 5 and 6, are cytotoxic agents. While compounds 2, 3, 5 and 6 blocked isoflavone accumulation in the soybean, the norisoprenoid (?)-loliolide (8) was somewhat stimulatory of these defense metabolites.     

Vernoguinamide: A new ceramide and other compounds from the root of Vernonia guineensis Benth. and their chemophenetic significance

The chemical investigation of the roots of Vernonia guineensis Benth. (Asteraceae) resulted in the isolation of a new ceramide, named vernoguinamide (1), together with fifteen known compounds, including three anthraquinones, physion (2), erythroglaucin (3) and emodin (4), three triterpenoids, hop-17(21)-en-3β-yl acetate (5), lupeol (6) and betulinic acid (7), six steroids, vernoguinoside A (8), vernoguinoside (9), β-sitosterol 3-O-β-D-glucoside (10), stigmasterol 3-O-β-D-glucoside (11), stigmasterol (12) and β-sitosterol (13) and three fatty acid derivatives, tetracosanoic acid (14), tricosanic acid (15) and arachidic acid glycerol ester (16). The structure of the new compound as well as those of the known compounds were established by spectrometric analysis including HRESI-MS, 1D and 2D-NMR and by comparison with the previously reported data. Among these compounds, the anthraquinones 2–4 and the triterpene 5 were isolated for the first time from Vernonia genus and compounds 6, 7 and 14–16 were extracted for the first time from the species. The isolated compounds were tested for their antibacterial activity and 3, 8 and 9 were the most active compounds against the tested bacteria. Furthermore, the chemophenetic relationships of the isolated compounds and their significance were also discussed.     

Rothmanniamide and other constituents from the leaves of Rothmannia hispida (K.Schum.) fagerl. (Rubiaceae) and their chemophenetic significance

The chemical investigation of the CH₂Cl₂/MeOH (1:1) extract of the leaves of Rothmannia hispida (K. Schum.) Fagerl. (Rubiaceae) led to the isolation of a new ceramide rothmanniamide (1) and a naturally isolated alkyl cinnamate derivative n-heptadecyl-4-hydroxy-trans-cinnamate (2), along with fifteen known compounds including lupeol palmitate (3), lupeol (4), a mixture of uvaol (5) and erythrodiol (6), ursolic acid (7), 30-nor-2α,3β-dihydroxyurs-12-ene (8), hederagenin (9), stigmast-22-en-3-ol (10), a mixture of β-sitosterol (11) and stigmasterol (12), stigmast-4,22-dien-3-ol (13), stigmasterol 3-O-β-D-glucoside (14), triacontan-1-ol (15), kaempferol 3-O-β-D-glucopyranoside (16) and D-mannitol (17). Their structures were elucidated with the help of MS and NMR data. Compounds 8, 10 and 15 were isolated for the first time from the Rubiaceae family. The crude extract and the isolates were assessed in vitro for their antileishmanial activity against Leishmania donovani 1 S (MHOM/SD/62/1 S) promastigotes and cytotoxicity on RAW 264.7 macrophage cells. Compounds 7 and 8 exhibited a highly potent antileishmanial activity with IC₅₀ values of 0.88 and 1.75 μg/mL, respectively, with good selectivity indexes (SI > 57). The chemophenetic significance of these compounds is also discussed.     

Furanocoumarins from the twigs of Ficus chlamydocarpa (Moraceae)

Two furanocoumarin derivatives, 3-methoxypsoralen (1) and 3,5-dimethoxypsoralen (2), along with nine known compounds, friedelinol (3), 3-oxo-11β-hydroxyoleanan-12-ene (4), lupeol (5), taraxer-3-one (6), a mixture of β-sitosterone (7a) and stigmast-4,22-dien-3-one (7b), ergosterol (8), 9,19-cyclolanost-3-one-24,25-diol (9), oleanan-12-ene-3,11-dione (10), and β-sitosterol 3-O-β-D-glucopyranoside (11) were isolated from the twigs of Ficus chlamydocarpa. Their structures were established by NMR spectroscopic analyses and HRESIMS. The structure of 1 was further confirmed from its single crystal X-ray diffraction. The crude extract, fractions and some isolated compounds were assessed for their preliminary antibacterial activity and cytotoxicity. One of the fractions (FB-B3) exhibited inhibition against the bacterial strain Pseudomonas agarici and induced a remarkable cytotoxic activity toward the human cervix carcinoma cell line KB-3-1 (IC₅₀ 0.166 mg/mL), and compounds 1, 6, and 7 showed moderate antibacterial activity against Bacillus subtilis and Micrococcus luteus.     

New cytotoxic protolimonoids from the stem bark of Aglaia argentea (Meliaceae)

Two new protolimonoid compounds, namely, argentinin A (1) and B (2) along with five known triterpenoid compounds, dammar-24-en-3α-ol (3), 3-epi-cabraleahydroxy lactone (4), (E)-25-hydroperoxydammar-23-en-3β,20-diol (5), mixture of eichlerianic acid and shoreic acid (6a and 6b), and dammar-24-en-3α,20-diol (7), were isolated from the stem bark of Aglaia argentea. The structure of new compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis. All of the compounds were tested for their cytotoxic effects against P-388 murine leukemia cells in vitro. Among those isolated compounds, argentinin A (1) showed the strongest activity with an IC₅₀ value of 1.27 μg/mL (3.05 μM).     

Unusual lipids and acylglucosylsterols from the roots of Livistona chinensis

A 70% ethanol extract from the roots of Livistona chinensis has been investigated, led to the isolation of 18 compounds, including two new 6′-O-acyl-β-d-glucosyl-β-sitosterols, 6′-O-(2″-hydroxyheptadecanoyl)-β-d-glucosyl-β-sitosterol (1) and 6′-O-(icosa-9″Z,12″Z-dienoyl)-β-d-glucosyl-β-sitosterol (2), two new keto esters, ethyl 16-(dodeca-4″′Z,7″′Z-dienyl)-29-oxo-15-(tetradeca-5″Z,8″Z,11″Z-trienyl) triacontanoate (7), and 16-hydroxy-8-oxohexadecyl tetradecanoate (9), a new unsaturated fatty acid, tetracosa-(11Z,14Z,18Z)-trienoic acid (8), as well as a new fatty alcohol, 10-decylnonadecane-1,19-diol (10). The structures of new compounds were elucidated, based on spectroscopic and chemical methods. The antiproliferative activity against four human tumor cell lines (K562, HL-60, HepG2, and CNE-1) was evaluated. Four compounds (1–3, 5) showed potent antiproliferative effects with the IC₅₀ of 10–100 μM. To our knowledge, this is the first report of the occurrence of 6′-O-acyl-β-d-glucosyl-β-sitosterol and 3-O-acyl-β-sitosterol in the genus Livistona. Keto fatty acids and their esters are also rare in higher plant.     

Thiophenes,polyacetylenes and terpenes from the aerial parts of Eclipata prostrata

One new bithiophenes, 5-(but-3-yne-1,2-diol)-5′-hydroxy-methyl-2,2′-bithiophene (2), two new polyacetylenic glucosides, 3-O-β-d-glucopyranosyloxy-1-hydroxy-4E,6E-tetradecene-8,10,12-triyne (8), (5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-β-d-glucopyranoside (9), six new terpenoid glycosides, rel-(1S,2S,3S,4R,6R)-1,6-epoxy-menthane-2,3-diol-3-O-β-d-glucopyranoside (10), rel-(1S,2S,3S,4R,6R)-3-O-(6-O-caffeoyl-β-d-glucopyranosyl)-1,6-epoxy menthane-2,3-diol (11), (2E,6E)-2,6,10-trimethyl-2,6,11-dodecatriene-1,10-diol-1-O-β-d-glucopyranoside (12), 3β,16β,29-trihydroxy oleanane-12-ene-3-O-β-d-glucopyranoside (13), 3,28-di-O-β-d-glucopyranosyl-3β,16β-dihydroxy oleanane-12-ene-28-oleanlic acid (14), 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl oleanlic-18-ene acid-28-O-β-d-glucopyranoside (15), along with fifteen known compounds (1, 3–7, and 16–24), were isolated from the aerial parts of Eclipta prostrata. Their structures were established by analysis of the spectroscopic data. The isolated compounds 1–9 were tested for activities against dipeptidyl peptidase IV (DPP-IV), compound 7 showed significant antihyperglycemic activities by inhibitory effects on DPP-IV in human plasma in vitro, with IC₅₀ value of 0.51 μM. Compounds 10–24 were tested in vitro against NF-κB-luc 293 cell line induced by LPS. Compounds 12, 15, 16, 19, 21, and 23 exhibited moderate anti-inflammatory activities.     

Microbial transformation of neoandrographolide by Mucor spinosus (AS 3.2450)

Microbial transformation of neoandrographolide (1), was performed by Mucor spinosus (AS 3.2450). Ten metabolites were obtained and identified as 14-deoxyandrographolide (2), 17,19-dihydroxy-8,13-ent-labdadien-16,15-olide (3), 3,14-dideoxyandrographolide (4), 7β-hydroxy-3,14-dideoxyandrographolide (5), 17,19-dihydroxy-7,13-ent-labdadien-16,15-olide (6), 8(17),13-ent-labdadien-16,15-olid-19-oic acid (7), 8α,17β-epoxy-3,14-dideoxyandrographolide (8), 8β,17,19-trihydroxy-ent-labd-13-en-16, 15-olide (9), phlogantholide-A (10), 19-[(β-d-glucopyranosyl)oxy]-19-oxo-ent-labda-8(17),13-dien-16,15-olide (11) by spectroscopic and chemical means. Among them, products 3, 5, 6, 8 and 9 were characterized as new compounds. The inhibitory effects of compounds 1–11 on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated and their preliminary structure–activity relationships (SAR) were discussed.     

Phytochemical and chemotaxonomic study on Ziziphus Jujuba Mill. (Rhamnaceae)

Fourteen compounds were isolated from fruits of Ziziphus jujuba Mill., including two flavonoids (1–2), one phenolic glycosides (3), one lignan (4), four phenols (5–8), three alkaloid (9–10, 14), three sesquiterpenoid (11–13). The structures of all the compounds were established by the NMR techniques, as well as by comparison with previously reported data in literature. Compounds 2″-glucosyl-8-C-glucosyl-4′-O-methylapigenin (1), 3′, 4′, 5′-trimethoxycinnamyl alcohol (5), 2-{4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2, 6-dimethoxy-phenoxy}propane-1, 3-diol (6), 1-(4-Hydroxyphenyl)ethane-1, 2-diol (8), (1S, 3S)-1-Methyl-l, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (9), (1R, 3S)-1-Methyl-l, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (10), grasshopper ketone (12), methyl (3R, 5R)-5-methoxy-3-phenylisoxazolidine-5-carboxylate (14) were firstly reported from the genus Ziziphus and the family Rhamnaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

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.     

Inhibitors of sterol biosynthesis. Syntheses of 14α-alkyl substituted 15-oxygenated sterols

The chemical syntheses of a number of 14α-alkyl substituted 15-oxygenated sterols have been pursued to permit evaluation of their activity in the inhibition of the biosynthesis of cholesterol and other biological effects. Described herein are the first chemical syntheses of 14α-ethyl-5α-cholest-7-en-3β-ol-15-one, bis-3β,15α-acetoxy-14α-ethyl-5α-cholest-7-ene, 3β-acetoxy-14α-ethyl-5α-cholest-7-en-15β-ol, 14α-ethyl-5α-cholest-7-en-3β,15β-diol, 14α-ethyl-5α-cholest-7-en-3β,15α-diol, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15α-ol, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15β-ol, bis-3β,15α-hexadecanoyloxy-14α-ethyl-5α-cholest-7-ene, 3β-hexadecanoyloxy-14α-ethyl-5α-cholest-7-en-15-one, 3α-benzoyloxy-14α-ethyl-5α-cholest-7-en-15-one, 14α-ethyl-5α-cholest-7-en-3α-ol-15-one, 14α-ethyl-5α-cholest-7-en-15-on-3β-yl pyridinium sulfate, 14α-ethyl-5α-cholest-7-en-15-on-3β-yl potassium sulfate (monohydrate), 14α-ethyl-5α-cholest-7-en-15-on-3α-yl pyridinium sulfate, 14α-ethyl-5α-cholest-7-en-15-on-3α-yl potassium sulfate (monohydrate), 3β-ethoxy-14α-ethyl-5α-cholest-7-en-15-one, 3β-acetoxy-14α-n-propyl-5α-cholest-7-en-15-one, 14α-n-propyl-5α-cholest-7-en-3β-ol-15-one, bis-3β, 15α-acetoxy-14α-n-propyl-5α-cholest-7-ene, 3β-acetoxy-14α-n-propyl-5α-cholest-7-en-15β-ol, 14α-n-propyl-5α-cholest-7-en-3β, 15α-diol, 14α-n-propyl-5α-cholest-7-en-3β, 15β-diol, 14α-n-butyl-5α-cholest-7-en-3β-ol-15-one, 3β-acetoxy-14-α-n-butyl-5α-cholest-7-en-15-one, bis-3β,15α-acetoxy-14α-n-butyl-5α-cholest-7-ene, 3β-acetoxy-14α-n-butyl-5α-cholest-7-en-15β-ol, 14α-n-butyl-5β-cholest-7-en-3β, 15β-diol, and 14α-n-butyl-5α-cholest-7-en-3β, 15α-diol.     

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.     

Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax

Two new ent-kauren-19-oic acid derivatives, ent-14S*-hydroxykaur-16-en-19-oic acid and ent-14S*,17-dihydroxykaur-15-en-19-oic acid together with eleven known compounds ent-kaur-16-en-19-oic acid, ent-kaur-16-en-19-al, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid, 8R,13R-epoxylabd-14-ene, eudesm-4(15)-ene-1β,6α-diol, (?)-7-epivaleran-4-one, germacra-4(15), 5E,10(14)-trien-9β-ol, acetyl aleuritolic acid, β-amyrin, and stigmasterol were isolated from the stem bark of Croton pseudopulchellus (Euphorbiaceae). Structures were determined using spectroscopic techniques. Ent-14S*-hydroxykaur-16-en-19-oic acid, ent-kaur-16-en-19-oic acid, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid and 8R,13R-epoxylabd-14-ene were tested for their effects on Semliki Forest virus replication and for cytotoxicity against human liver tumour cells (Huh-7 strain) but were found to be inactive. Ent-kaur-16-en-19-oic acid, the major constituent, showed weak activity against the Plasmodium falciparum (CQS) D10 strain.     

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.     

Metabolism of 5β-pregnane-3,20-dione and 3β-hydroxy-5β-pregnan-20-one by Digitalis suspension cultures

Digitalis purpurea normal callus suspension culture is capable of metabolizing 5β-pregnane-3,20-dione (1) to 3β-hydroxy-5β-pregnan-20-one (2), 3α-hydroxy-5β-pregnan-20-one (3), 3β-hydroxy-5β-pregnan-20-one glucoside (7) and 3α-hydroxy-5β-pregnan-20-one glucoside (8). Digitalis purpurea habituated callus suspension culture is also capable of metabolizing 1 to 2, 3, 5β-pregnane-3β,20β-diol (5), (7), (8), 5β-pregnane-3β,20α-diol monoglucoside (9) and 5β-pregnane-3α,20α-diol monoglucoside (11). Furthermore, it was observed that 3β-hydroxy-5β-pregnan-20-one (2) is converted to 7, 9 and 11 by both suspension cultures. At the same time, 1, 3, 5 and 8 were detected in normal callus, while 5β-pregnane-3β,20α-diol (4) and 5β-pregnane-3β,20β-diol monoglucoside (10) were present in the habituated callus culture.