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1.
Huifeng Li Min Ye Hongzhu Guo Yin Tian Jie Zhang Jianping Zhou Yuchi Hu Dean Guo 《Phytochemistry》2009,70(11-12):1416-1420
Biotransformation of 20(S)-protopanaxadiol (1) by the fungus Mucor spinosus AS 3.3450 yielded eight metabolites (2–9). On the basis of NMR and MS analyses, the metabolites were identified as 12-oxo-15α,27-dihydroxyl-20(S)-protopanaxadiol (2), 12-oxo-7β,11α,28-trihydroxyl-20(S)-protopanaxadiol (3), 12-oxo-7β,28-dihydroxyl-20(S)-protopanaxadiol (4), 12-oxo-15α,29-dihydroxyl-20(S)-protopanaxadiol (5), 12-oxo-7β,15α-dihydroxyl-20(S)-protopanaxadiol (6), 12-oxo-7β,11β-dihydroxyl-20(S)-protopanaxadiol (7), 12-oxo-15α-hydroxyl-20(S)-protopanaxadiol (8), and 12-oxo-7β-hydroxyl-20(S)-protopanaxadiol (9), respectively. Among them, 2–5, 7, and 8 are new compounds. These results indicated that M. spinosus could catalyze the specific C-12 dehydrogenation of 20(S)-protopanaxadiol, as well hydroxylation at different positions. These biocatalytic reactions may be difficult for chemical synthesis. The biotransformed products showed weak in vitro cytotoxic activities. 相似文献
2.
A water-soluble polysaccharide isolated from Dalbergia sissoo Roxb. leaves was purified and major homogeneous fraction obtained by GPC. Complete hydrolysis of the polysaccharide followed by paper chromatography and GLC analysis indicated the presence of l-rhamnose, d-glucuronic acid, d-galactose and d-glucose in molar ratio of 1:1:2:2.33, respectively. Partial hydrolysis of the polysaccharide furnished one tri-[I], one hepta-[II] and one nona-[III] saccharides. Hydrolysis of the oligosaccharide I, II and III followed by GLC analysis furnished d-glucose and l-rhamnose (2:1); l-rhamnose, d-galactose and d-glucuronic acid (1:3:3); and l-rhamnose, d-galactose and d-glucose (1:3:5), respectively. Methylation analysis and periodate oxidation of the oligosaccharide I indicated the presence of two non reducing glucose units linked to rhamnose by 1→2 and 1→4 linkages, respectively. Oligosaccharide II is a branched molecule with a main chain consisting of 1,3-linked β-d-galactopyranosyl (2 mol), 1,3,4 linked α-l-rhamnopyranosyl (1 mol) and 1,4,6 linked β-d-galactopyranosyl unit (1 mol) and non reducing β-d-glucuronic acid at the end along with side chains of β-d-glucouronopyranosyl units (2 mol). Oligosaccharide III is also a branched molecule with a main chain consisting of 1,3,4 linked α-l-rhamnopyranosyl (1 mol), 1,2,4 linked β-d-glucopyranosyl (1 mol), 1,3 and 1,4 linked β-d-galactopyranosyl (2 and 1 mol, respectively) having β-d-glucopyranosyl as a non reducing end. 相似文献
3.
Jie-Li Lü Jin-Ao Duan Yu-Ping Tang Nian-Yun Yang Lai-Bin Zhang 《Biochemical Systematics and Ecology》2009,37(4):405-411
Phytochemical investigation of the radix of Angelica sinensis has led to the isolation and identification of a new phthalide dimer, (3Z)-(3aR,6S,3′R,8′S)-3a.8′,6.3′-diligustilide (1), along with three known phthalide dimers, including riligustilide (2), levistolide A (3), senkyunolide O (4), and three known phthalide monomers, including 3,9-dihydroxyl-ligustilide (5), (Z)-butylidene phthalide (6), (Z)-ligustilide (7). Their structures were determined by spectroscopic methods including IR, NMR (1H NMR, 13C NMR, COSY, HSQC, HMBC and NOESY) and MS. Meanwhile, the possible biosynthesis pathways of compounds 1 and 5 were hypothesized. 相似文献
4.
Bo Zhang Sheng-Ping Yang Sheng Yin Chuan-Rui Zhang Yan Wu Jian-Min Yue 《Phytochemistry》2009,70(10):1305-1308
Four limonoids, 1-O-deacetyl-6-deoxykhayanolide E (1), 1-O-deacetyl-2α-hydroxykhayanolide E (2), 3-acetyl-khayalactone (3), 11α-acetoxy-2α-hydroxy-6-deoxy-destigloylswietenine acetate (4), along with 12 known limonoids, were isolated from the stems of Khaya ivorensis. Their structures were elucidated on the basis of spectroscopic analysis. 相似文献
5.
Chemical examination of the ethyl acetate solubles of the CH3OH:CH2Cl2 (1:1) extract of the roots of Ceriops decandra collected from Kauvery estuary resulted in the isolation of four new diterpenoids, ceriopsins A–D (1–4). The structures of the new diterpenoids were elucidated by a study of their physical and spectral data as methyl 17-hydroxy-16-oxobeyeran-18-oate (1), methyl 16(R)-16,17-dihydroxybeyeran-18-oate (2), 1β,15(S)-isopimar-7-ene-1,15,16-triol (3), and 8,15(R)-epoxypimarane-1β,16-diol (4). 相似文献
6.
Two chromones: 5-hydroxy-2-(14′-(E)-nonadecenyl) chromone (1) and 5-hydroxy-2-[12′-(3″,4″-methylenedioxyphenyl)dodecanyl] chromone (2), together with six known compounds have been isolated from Peperomia vulcanica Baker & C. H. Wright (Piperaceae). Their structures were determined by spectroscopic analysis including 2D NMR techniques. 相似文献
7.
Deniz Tasdemir Reto Brun Scott G. Franzblau Yükselen Sezgin Ihsan als 《Phytomedicine》2008,15(3):209-215
Resin glycosides are secondary metabolites exclusive to the convolvulaceous plants. In this study, crypthophilic acids A–C (1–3), the first resin glycosides occurring in another family (Scrophulariaceae), and the other constituents of Scrophularia cryptophila were examined for in vitro antiprotozoal and antimycobacterial potentials. Except for crypthophilic acid B (2), all tested compounds exhibited growth-inhibitory effect against Trypanosoma brucei rhodesiense, with l-tryptophan (6) and buddlejasaponin III (7) being the most potent ones (IC50's 4.1 and 9.7 μg/ml). In contrast, the activity towards Trypanosoma cruzi was poor, and only crypthophilic acid C (3), 6 and 7 were trypanocidal at concentrations above 40 μg/ml. With the exception of 2 and 6, all compounds were active against Leishmania donovani. Harpagide (4) and 3 emerged as the best leishmanicidal agents (IC50's 2.0 and 5.8 μg/ml). Only compounds 3, 6 and 7 showed antimalarial activity against Plasmodium falciparum with IC50 values of 4.2, 16.6 and 22.4 μg/ml. Overall the best and broadest spectrum activity was presented by compounds 3 and 7, as they inhibited all four parasitic protozoa. None of the isolates had significant activity against Mycobacterium tuberculosis (MICs >100 μg/ml) or were toxic towards mammalian (L6) cells. This is the first report of antiprotozoal activity for natural resin glycosides, as well as for harpagide (4), acetylharpagide (5), tryptophan (6) and buddlejasaponin III (7). 相似文献
8.
Lin Yang Runjiang Qu Jungui Dai Xiaoguang Chen 《Journal of Molecular Catalysis .B, Enzymatic》2007,46(1-4):8-13
Mucor genevensis were used to bioconvert sinenxan A [2α,5α,10β,14β-tetraacetoxy-taxa-4(20),11-diene], a taxoid isolated from callus tissue cultures of Taxus spp., and 10 metabolites were obtained. On the basis of chemical and spectroscopic data analyses, their structures were determined as 10β-methoxy-2α,5α,14β-triacetoxy-taxa-4(20),11-diene (2), 10β-hydroxy-2α,5α,14β-triacetoxy-taxa-4(20),11-diene (3), 2α,5α,10β,14β-tetraacetoxy-4β,20-epoxy-taxa-11(12)-ene (4), 6α-hydroxy-2α,5α,10β,14β-tetraacetoxy-taxa-4(20),11-diene (5), 9α-hydroxy-2α,5α,10β,14β-tetraacetoxy-taxa-4(20),11-diene (6), 10β-hydroxy-2α,5α,14β-triacetoxy-4β,20-epoxy-taxa-11(12)-ene (7), 6α,10β-dihydroxy-2α,5α,14β-triacetoxy-taxa-4(20),11-diene (8), 6α-hydroxy-2α,5α,10β,14β-tetraacetoxy-4β,20-epoxy-taxa-11(12)-ene (9), and 9α,10β-dihydroxy-2α,5α,14β-triacetoxy-taxa-4(20),11-diene (10), and 9α,10β-O-(propane-2,2-diyl)-2α,5α,14β-triacetoxy-taxa-4(20),11-diene (11). Among them, metabolites 2, 4, and 9 were three new compounds. The three major metabolites 2, 3, and 4 along with 1 were pharmacologically evaluated for their multi-drug resistance (MDR) reversal activities towards taxol-resistant A549 tumor cells, and the results showed that 4 possessed about two-fold activity as verapamil, while 2, and 3 possessed lower activity than verapamil and 1. 相似文献
9.
M. Iqbal Choudhary Nadra Naheed Ahmed Abbaskhan Sajjad Ali Atta-ur-Rahman 《Phytochemistry》2009,70(11-12):1467-1473
Five glycosides, 2-(trans-cinnamoyloxy-methyl)-1-butene-4-O-β-d-glucopyranoside (1), 4-(6′-O-trans-cinnamoyl)-(2-hydroxymethyl-4-hydroxy-butenyl-β-d-glucopyranoside (2), 6′′-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-β-d-glucopyranoside (3), 6′-O-(4-methoxy-trans-cinnamoyl) α/β-d-glucopyranose (4) 6′-O-(4′′-methoxy-trans-cinnamoyl)-kaempferol-3-β-d-glucopyranoside (7) along with six known compounds, (+)-isolariciresinol 3a-O-β-d-glucopyranoside (8) (+)-lyoniresinol 3a-O-β-d-glucopyranoside (9), apigenin 7-O-β-d-glucopyranoside (10), quercetin 3-O-β-d-glucopyranoside (11), 6′-O-cinnamoyl-α/β-d-glucopyranose (6) 6’-O-p-coumaroyl-α/β-d-glucopyranose (5) were isolated from the whole plant of Spiraea canescens. Some of these compounds showed potent radical scavenging activity in relevant non-physiological assays. Their structures were determined by NMR spectroscopic and CID mass spectrometric techniques. 相似文献
10.
M. Sautour F. Canon T. Miyamoto A. Dongmo M.-A. Lacaille-Dubois 《Biochemical Systematics and Ecology》2008,36(7):559-563
Phytochemical investigation of the rhizome of Dioscorea dumetorum has led to the isolation by several chromatographic steps on normal and reversed phase silica gel of a new ecdysteroid, (20R)-5β,11α,20-trihydroxyecdysone (1), and two known ecdysteroids, ajugasterone C (2) and herkesterone (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR (COSY, TOCSY, HSQC and HMBC). This is the first report on the occurrence of phytoecdysteroids in the Dioscoreaceae family. These compounds were devoid of antifungal activity against three Candida species (Candida albicans, Candida glabrata and Candida tropicalis, MIC > 200 μg/ml). 相似文献
11.
Yi-Pei Lin Tai-Yuan Chen Hsiang-Wen Tseng Mei-Hsien Lee Shui-Tein Chen 《Phytochemistry》2009,70(9):1173-1181
A platform for screening drugs for their ability to protect neuronal cells against cytotoxicity was developed. Nerve growth factor (NGF) differentiates PC12 cells into nerves, and these differentiated PC12 cells enter apoptosis when challenged with 6-hydroxydopamine (6-OHDA). A screening spectrophotometer was used to assay cytotoxicity in these cells; pretreatment with test samples allowed identification of compounds that protected against this neuronal cytotoxicity. The 95% ethanol extract of Phoenix hanceana Naudin var. formosana Beccari. (PH) showed potential neuroprotective activity in these assays. The PH ethanol extract was further fractionated by sequential partitioning with n-hexane, ethyl acetate (EtOAc), n-butanol (n-BuOH), and water. Subsequent rounds of assaying resulted in the isolation of ten constituents, and their structures were characterized by various spectroscopic techniques and identified by comparison with previous data as: isoorientin (1), isovitexin (2), veronicastroside (3), luteolin-7-O-β-d-glucopyranoside (4), isoquercitrin (5), tricin-7-neohesperidoside (6), tricin-7-O-β-d-gluco-pyranoside (7), (+)-catechin (8), (−)-epicatechin (9), and orientin 7-O-β-d-glucopyranoside (10). Among these compounds, isovitexin (2), luteolin-7-O-β-d-glucopyranoside (4) and (+)-catechin (8) showed significant neuroprotective activity in cell viability (WST-8 reduction), anti-apoptosis (Annexin V-FITC/propidium iodide double-labeled flow cytometry), and cellular ROS scavenging assays (besides isovitexin (2)), as well as a decreased caspase-8 activity in 6-OHDA-induced PC12 cells. Hence, isovitexin (2), luteolin-7-O-β-d-glucopyranoside (4), and (+)-catechin (8) protected PC12 cells from 6-OHDA-induced apoptotic neurotoxicity. 相似文献
12.
An ellagitannin monomer, nilotinin M1 (1), and three dimers, nilotinins D1 (2), D2 (3), and D3 (4), were isolated from leaves of Tamarix nilotica (Ehrenb.) Bunge. Structures were elucidated based on analysis of spectroscopic data and chemical correlations with known compounds. In addition, six known tannins, hirtellin A (5) (dimer), remurin A (6), remurin B (7), 1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-d-glucose (8), gemin D (9), and hippomanin A (10) (monomers), were isolated for the first time from this plant species. The reported 13C NMR assignments of the dehydrodigalloyl moiety and glucose cores of 5 are revised, and the 13C NMR spectroscopic data for 6 and 7 are also reported for the first time. 相似文献
13.
Amelia P. Guevara Carolyn Vargas Hiromu Sakurai Yasuhiro Fujiwara Keiji Hashimoto Takashi Maoka Mutzuo Kozuka Yoshohiro Ito Harukuni Tokuda Hoyoku Nishino 《Mutation Research - Genetic Toxicology and Environmental Mutagenesis》1999,440(2):1270
In the course of studies on the isolation of bioactive compounds from Philippine plants, the seeds of Moringa oleifera Lam. were examined and from the ethanol extract were isolated the new O-ethyl-4-(α-
-rhamnosyloxy)benzyl carbamate (1) together with seven known compounds, 4(α-
-rhamnosyloxy)-benzyl isothiocyanate (2), niazimicin (3), niazirin (4), β-sitosterol (5), glycerol-1-(9-octadecanoate) (6), 3-O-(6′-O-oleoyl-β-
-glucopyranosyl)-β-sitosterol (7), and β-sitosterol-3-O-β-
-glucopyranoside (8). Four of the isolates (2, 3, 7, and 8), which were obtained in relatively good yields, were tested for their potential antitumor promoting activity using an in vitro assay which tested their inhibitory effects on Epstein–Barr virus-early antigen (EBV-EA) activation in Raji cells induced by the tumor promoter, 12-O-tetradecanoyl-phorbol-13-acetate (TPA). All the tested compounds showed inhibitory activity against EBV-EA activation, with compounds 2, 3 and 8 having shown very significant activities. Based on the in vitro results, niazimicin (3) was further subjected to in vivo test and found to have potent antitumor promoting activity in the two-stage carcinogenesis in mouse skin using 7,12-dimethylbenz(a)anthracene (DMBA) as initiator and TPA as tumor promoter. From these results, niazimicin (3) is proposed to be a potent chemo-preventive agent in chemical carcinogenesis. 相似文献
14.
A further phytochemical investigation on the whole plants of Ypsilandra thibetica yielded one sapogenin and 12 spirostanol saponins. Five of these are new compounds, designated as ypsilandrosides C-G (2–6). Their structures were determined by detailed spectroscopic analysis, including extensive 1D and 2D NMR data, and by the result of a hydrolytic reaction. Compounds 2–5 were rare steroidal saponins that an apiofuranosyl unit was directly linked at C-3 of the aglycone. Selected spirostanol saponins (2–6, 9) were tested for their cytotoxic activities against K562, SPC-A-1, BGC-823, Eca-109, and AGS cell lines. Compounds 6 and 9 showed moderate inhibitory activity against all five cell lines. The antifungal properties of the new spirostanol saponins (2–6) against Candida albicans were also determined. 相似文献
15.
Roots of Anisotome pilifera yielded typical Apiaceae compounds 6,7-dimethoxy-coumarin 1 and falcarindiol 2, plus the irregular diterpenes anisotomenoic acid 3 and anisotomene alcohol 4. The new germacrane derivative 8-O-senecioyl-6β,8α,11-trihydroxygermacra-1(10)E,4E-diene 5 was also isolated and the structure established by means of high resolution mass spectrometry and 1-D and 2-D NMR spectroscopy. Distribution and chemosystematic significance of 6,8-dihydroxygermacra-1(10)E,4E-dienes and 6,8,11-trihydroxygermacra-1(10)E,4E-dienes are discussed. Additionally, leaves of A. pilifera yielded chlorogenic acid 6 and high amounts of luteolin 7-O-α-
-rhamnosyl(1→6)-β-
-glucoside 7. 相似文献
16.
Mohamed-Elamir F. Hegazy Chika Kuwata Akihito Matsushima Ahmed A. Ahmed Toshifumi Hirata 《Journal of Molecular Catalysis .B, Enzymatic》2006,39(1-4):13
The biotransformation of sesquiterpenoids having an α,β-unsaturated carbonyl group, such as α-santonin (1), lancerodiol p-hydroxybenzoate (2), 8,9-dehydronootkatone (3), and nootkatone (4), with cultured suspension cells of Marchantia polymorpha was investigated. It was found that the CC double bond of 1 and 2 was hydrogenated to give 1,2-dihydro-α-santonin (5) and 3,4-dihydrolancerodiol p-hydroxybenzoate (6), respectively, while the allylic position of the CC double bond of 3 and 4 was hydroxylated to give 13-hydroxy-8,9-dehydronootkatone (7) and 9-hydroxynootkatone (8), respectively. 相似文献
17.
Di-nor-benzofuran neolignan aldehydes, Δ7-3,4-methylenedioxy-3′-methoxy-8′,9′-dinor-4′,7-epoxy-8,3′-neolignan-7′-aldehyde (ocophyllal A) 1, Δ7-3,4,5,3′-tetramethoxy-8′,9′-dinor-4′,7-epoxy-8,3′-neolignan-7′-aldehyde (ocophyllal B) 2, and macrophyllin-type bicyclo[3.2.1]octanoid neolignans (7R, 8R, 3′S, 4′S, 5′R)-Δ8′-4′-hydroxy-5′-methoxy-3,4-methylenedioxy-2′,3′,4′,5′-tetrahydro-2′-oxo-7.3′,8.5′-neolignan (ocophyllol A) 3, (7R, 8R, 3′S, 4′S, 5′R)-Δ8′-4′-hydroxy-3,4,5′-trimethoxy-2′,3′,4′,5′-tetrahydro-2′-oxo-7.3′,8.5′-neolignan (ocophyllol B) 4, (7R, 8R, 3′S, 4′S, 5′R)-Δ8′-4′-hydroxy-3,4,5,5′-tetramethoxy-2′,3′,4′,5′-tetrahydro-2′-oxo-7.3′,8.5′-neolignan (ocophyllol C) 5, as well as 2′-epi-guianin 6 and (+)-licarin B 7, were isolated and characterized from leaves of Ocotea macrophylla (Lauraceae). The structures and configuration of these compounds were determined by extensive spectroscopic analyses. Inhibition of platelet activating factor (PAF)-induced aggregation of rabbit platelets were tested with neolignans 1–7. Although compound 6 was the most potent PAF-antagonist, compounds 3–5 showed some activity. 相似文献
18.
Vatcharin Rukachaisirikul Yaowapa Sukpondma Chaweewan Jansakul Walter C. Taylor 《Phytochemistry》2002,60(8)
Five isoflavone glycosides, named derriscandenosides A–E (1–5), were isolated from the stems of Derris scandens, together with ten known compounds comprising one isoflavone, two benzoic acid derivatives, three glucosyl isoflavones and four rhamnosyl-(1→6)-glucosyl isoflavones. The structures of the glycosides were assigned on the basis of spectroscopic data, especially of the acetate derivatives. Three known rhamnosyl-(1→6)-glucosyl isoflavones isolated from a crude fraction were retested for hypotensive activity with varying results. 相似文献
19.
Katsuyoshi Matsunami Hideaki Otsuka Kazunari Kondo Takakazu Shinzato Masatoshi Kawahata Kentaro Yamaguchi Yoshio Takeda 《Phytochemistry》2009,70(10):1277-1285
A lignan glucoside, (+)-pinoresinol 4-O-[6″-O-galloyl]-β-d-glucopyranoside (1), and two megastigmane glucosides, named macarangiosides E and F (2, 3), together with 15 known compounds (4–18) were isolated from leaves of Macaranga tanarius (L.) Müll.-Arg. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. In addition, the absolute stereochemistry of macarangiosides B and C isolated previously from the same plant was also determined for the first time. Compounds 1 and 2 were galloylated on glucose and possessed potent DPPH radical-scavenging activity. 相似文献
20.
Toshio Morikawa Yuanyuan Xie Yasunobu Asao Masaki Okamoto Chihiro Yamashita Osamu Muraoka Hisashi Matsuda Yutana Pongpiriyadacha Dan Yuan Masayuki Yoshikawa 《Phytochemistry》2009,70(9):1166-1172
The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC50 = ca. 614 μg/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I–III (1–3), and raraoside A (4), were isolated together with 13 known saponins and four known sesquiterpene glycosides. Among them, several saponin constituents including rarasaponins I (1, IC50 = 131 μM) and II (2, 172 μM), and raraoside A (4, 151 μM) inhibited pancreatic lipase activity, which were stronger than that of theasaponin E1 (270 μM). 相似文献