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Bajgai SP Prachyawarakorn V Mahidol C Ruchirawat S Kittakoop P 《Phytochemistry》2011,72(16):2062-2067
Hybrid flavan-chalcones, desmosflavans A (1) and B (2), together with three known compounds, cardamonin (3), pinocembrin (4) and chrysin (5), were isolated from leaves of Desmos cochinchinensis. Cardamonin (3) and chrysin (5) exhibited potent antioxidant activity with 15.0 and 12.2 ORAC units. Desmosflavans A (1) and B (2), pinocembrin (4), and chrysin (5) were found to be inhibitors of aromatase with respective IC50 values of 1.8, 3.3, 0.9, and 0.8 μM. Desmosflavan A (1) inhibited lipoxygenase with the IC50 value of 4.4 μM. Desmosflavan A (1) exhibited cytotoxic activity with IC50 values of 0.29–3.75 μg/mL, while desmosflavan B (2) showed IC50 values of 1.71–27.0 μg/mL. 相似文献
3.
Soniamol Joseph Kainoor K. Janardhanan Varughese George Sabulal Baby 《Phytochemistry letters》2011,4(3):386-388
A new epoxidic ganoderic acid, 8α,9α-epoxy-3,7,11,15,23-pentaoxo-5α-lanosta-26-oic acid (1), together with the known compounds 3β-hydroxy-7,11,15,23-tetraoxo-5α-lanosta-8-en-26-oic acid (2), ergosta-7,22-diene-3β-yl pentadecanoate (3), ergosta-7,22-diene-3β-ol (4), β-sitosterol (5), fatty acids (6–10), fatty acid ester (11) and octadecane (12) were isolated from the fruiting bodies of Ganoderma lucidum from south India. Their structures were determined by 1H, 13C, 13C DEPT, 1H–1H COSY, HMBC, HSQC, NOESY NMR, FT-IR, UV–vis and FABMS spectral analysis. Compounds (1–3) exhibited good antifungal activity against Candida albicans in disc diffusion assay (100 μg/disc). Steroid ester (3) showed moderate anti-inflammatory activity (59.7% inhibition, 100 mg/kg body weight) in carrageenan-induced paw edema. 相似文献
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One new (1) and seven (2–8) known sesquiterpenoids, four dimeric tryptamine-related alkaloids (9–12) and six glycosides (13–18) were isolated from the fruits and leaves of Chimonanthus praecox (wintersweet). Based on its spectroscopic data, the new structure of compound 1, an oppositane-type sesquiterpenoid, was elucidated to be the C-4 epimer of bullatantriol (2). All isolated compounds were evaluated for their cytotoxicities against a small panel of human cancer cell lines, and only the chimonanthine-type alkaloids (10–12) were found to have cytotoxic effects against gastric carcinoma NUGC3 and hepatocarcinoma SNU739 cancer cells, with IC50 values ranging from 10.3 to 19.7 μM. 相似文献
5.
Xiao Liang Zhao Wen Guang Jing Shu Ying Han Guang Li Sun Yu Mei Liu Qi Wei Zhang Xiao Jun Ma Zhi Min Wang An Liu 《Phytochemistry letters》2011,4(3):267-270
Two new furostanol saponins, 3-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-25(R)-furosta-5,22(23)-dien-3β,20α,26-triol (1), 3-O-[β-d-glucopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-20(R)-methoxyl-25(R)-furosta-5,22(23)-dien-3β,26-diol (2) were isolated from the Dioscorea panthaica along with five known steroidal saponins (3–7). The structures of the new saponins were determined by detailed analysis of spectral data (including 2D NMR spectroscopy). The inhibitory activities of the saponins against α-glucosidase were investigated, gracillin (4) and 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-25(R)-furosta-5,20(22)-dien-3β,26-diol (5) were found to exhibit potent activities with IC50 values of 0.11 ± 0.04 mM and 0.09 ± 0.01 mM. 相似文献
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Jun He Yi Shen Jian-Shuang Jiang Ya-Nan Yang Zi-Ming Feng Pei-Cheng Zhang Shao-Peng Yuan Qi Hou 《Carbohydrate research》2011,(13):1903
Eight new linear polyacetylene glucosides (1–8), containing two C10-, one C13- and five C14-acetylenes, together with three known polyacetylenes (9–11) were isolated from the florets of Carthamus tinctorius L. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The absolute configurations of compounds 3–9 were confirmed by Snatzke and Gerards’s method, observing the induced circular dichroism after addition of dirhodium tetrakis (trifluoroacetate) [Rh2(OCOCF3)4] in CHCl3. All the isolated compounds (1–11) were also tested for inhibitory activities against LPS-induced NO production in murine macrophages and just showed weak activities at concentrations of 1 × 10−5 M. 相似文献
7.
Chen GT Yang M Song Y Lu ZQ Zhang JQ Huang HL Wu LJ Guo DA 《Applied microbiology and biotechnology》2008,77(6):1345-1350
Preparative-scale fermentation of ginsenoside Rb1 (1) with Acremonium strictum AS 3.2058 gave three new compounds, 12β-hydroxydammar-3-one-20 (S)-O-β-d-glucopyranoside (7), 12β, 25-dihydroxydammar-(E)-20(22)-ene-3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (8), and 12β, 20 (R), 25-trihydroxydammar-3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (9), along with five known compounds, ginsenoside Rd (2), gypenoside XVII (3), ginsenoside Rg3 (4), ginsenoside F2 (5), and compound K (6). The structural elucidation of these metabolites was based primarily on one- and two-dimensional nuclear magnetic resonance
and high-resolution electron spray ionization mass spectra analyses. Among these compounds, 2–6 are also the metabolites of ginsenoside Rb1 in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, A. strictum might be a useful tool for generating mammalian metabolites of related analogs of ginsenosides for complete structural identification
and for further use in pharmaceutical research in this series of compounds. In addition, the biotransformation kinetics was
also investigated. 相似文献
8.
Phytochemical investigation of the methanol extract from the whole plants of Patrinia scabiosaefolia Fisch. resulted in the isolation of four new triterpenoid saponins (1–4) along with six known compounds (5–10). On the basis of spectroscopic and chemical methods, the structures of the new compounds were established as 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-12β,30-dihydroxy-olean-28,13β-olide (1), 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-12β,30-dihydroxy-olean-28,13β-olide (2), 3-O-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl-12β, 30-dihydroxy-olean-28,13β-olide (3), and 3-O-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-oleanolic acid 28-O-β-d-glucopyranoside (4), respectively. Compounds 1–3 possess a novel 12β,30-dihydroxy-olean-28,13β-lactone aglycone and a 12β-hydroxy substituent that is rarely found in this kind of triterpenoid saponin. 相似文献
9.
Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-{β-d-xylopyranosyl-(1→3)-α-l-arabinopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyl-(25S)-spirost-5-ene-3β,17α-diol (1), 1-O-[α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-β-d-xylopyranosyl-3-O-α-l-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-α-l-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3β,17α-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells. 相似文献
10.
Hsu FL Yang LM Chang SF Wang LH Hsu CY Liu PC Lin SJ 《Applied microbiology and biotechnology》2007,74(3):659-666
Preparative-scale fermentation of gallic acid (3,4,5-trihydroxybenzoic acid) (1) with Beauveria sulfurescens ATCC 7159 gave two new glucosidated compounds, 4-(3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-methoxy-benzoic
acid (4), 3-hydroxy-4,5-dimethoxy-benzoic acid 3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yl ester (7), along with four known compounds, 3-O-methylgallic acid (2), 4-O-methylgallic acid (3), 3,4-O-dimethylgallic acid (5), and 3,5-O-dimethylgallic acid (6). The new metabolite genistein 7-O-β-D-4″-O-methyl-glucopyranoside (8) was also obtained as a byproduct due to the use of soybean meal in the fermentation medium. The structural elucidation of
the metabolites was based primarily on 1D-, 2D-NMR, and HRFABMS analyses. Among these compounds, 2, 3, and 5 are metabolites of gallic acid in mammals. This result demonstrated that microbial culture parallels mammalian metabolism;
therefore, B. sulfurescens might be a useful tool for generating mammalian metabolites of related analogs of gallic acid (1) for complete structural identification and for further use in investigating pharmacological and toxicological properties
in this series of compounds. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter gene assay
was used to initially screen for the biological activity of the 6 compounds, 2–6 and 8, along with 1 and its chemical O-methylated derivatives 9–13. Among the 12 compounds tested, 11–13 were found to be significant, but less active than the reference compounds of methylprednisolone and dexamethasone. 相似文献
11.
Ma SG Tang WZ Yu SS Chen XG Liu Y Wang WJ Qu J Xu S Ren JH Li Y Lü HN 《Carbohydrate research》2011,(9):178-1168
Four new phenolic diglycosides (1–4), named illoliganoside A–D, and three known glycosides (5–7), were isolated from the roots of Illiciumoligandrum. The structures of the new diglycosides were determined on the basis of HRMS, NMR spectroscopic, and chemical methods. The anti-inflammatory and cytotoxic activities for 1–7 were evaluated. 相似文献
12.
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
13.
Seven triterpenoid saponins, including four new compounds, catunarosides A–D (1–4), and three known compounds, swartziatrioside (5), aralia-saponin V (6), araliasaponin IV (7) were isolated from the stem bark of Catunaregam spinosa, a Chinese mangrove associate. Their structures were elucidated on the basis of their spectral data and hydrolysis experiments. The antifeedant activities of compounds 1–7 against Plutella xylostella were also evaluated. 相似文献
14.
Timofey V. Malyarenko Alla A. Kicha Natalia V. Ivanchina Anatoly I. Kalinovsky Pavel S. Dmitrenok Svetlana P. Ermakova Valentin A. Stonik 《Steroids》2011,76(12):1280-1287
Six new steroidal biglycosides, cariniferosides A–F (1–6), were isolated along with six previously known glycosides, 7–12, from the alcoholic extract of the starfish Asteropsis carinifera. The structures of 1–6 were determined by extensive NMR and ESIMS techniques. The isolated compounds did not show any apparent cytotoxicity in cancer cell lines HCT-116, RPMI-7951, and T-47D, but sulfated compounds 6, 11, and 12 demonstrated a significant inhibition of RPMI-7951 and T-47D cell colony formation in a soft agar clonogenic assay. 相似文献
15.
Deng Y Chin YW Chai HB de Blanco EC Kardono LB Riswan S Soejarto DD Farnsworth NR Kinghorn AD 《Phytochemistry letters》2011,4(3):213-217
A phytochemical investigation of the leaves of Vitex quinata (Lour.) F.N. Williams (Verbenaceae), guided by a cytotoxicity assay against the MCF-7 human breast cancer cell line, led to the isolation of a new δ-truxinate derivative (1) and a new phytonoic acid derivative (2), together with 12 known compounds. The structures of the new compounds were determined by spectroscopic methods as dimethyl 3,4,3′,4′-tetrahydroxy-δ-truxinate (1) and methyl 10R-methoxy-12-oxo-9(13),16E-phytodienoate (2), respectively. In a cytotoxicity assay, (S)-5-hydroxy-7,4′-dimethoxyflavanone (3) was found to be the sole active principle, with ED50 values of 1.1–6.7 μM, respectively, when tested against a panel of three human cancer cells. Methyl 3,4,5-O-tricaffeoyl quinate (4) showed activity in an enzyme-based ELISA NF-κB p65 assay, with an ED50 value of 10.3 μM. 相似文献
16.
《Bioscience, biotechnology, and biochemistry》2013,77(7):1714-1721
A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6–8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC50 values of 3.2±0.02, 2.2±0.12, and 2.2±0.06 μg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 μg/ml. 相似文献
17.
Sea Cucumbers Triterpene Glycosides, the Recent Progress in Structural Elucidation and Chemotaxonomy
Vladimir I. Kalinin Alexandra S. Silchenko Sergey A. Avilov Valentin A. Stonik Alexey V. Smirnov 《Phytochemistry Reviews》2005,4(2-3):221-236
Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). Majority of the glycosides
belong to holostane type (lanostane derivatives with 18(20)-lactone). Carbohydrate chains of these glycosides contain xylose,
glucose, quinovose, 3-O-methylglucose and 3-O-methyl sylose. During the last 5 years, main investigations were focused on holothurians belonging to the order Dendrochirotida
collected in the North Pacific, North Atlantic, Antarctic and in subtropical waters. The glycosides of holothurians belonging
to the order Aspidochirotida have also been studied. The most uncommon structural features of carbohydrate chains of new glycosides
were: (1) the presence of quinovose as fifth terminal monosaccharide unit and the presence of two quinovose residues; (2)
the presence of glucose instead of common xylose as fifth terminal monosaccharide unit; (3) trisaccharide carbohydrate chain;
(4) the presence of two 3-O-methylxylose terminal monosaccharide units; (5) the presence of sulfate group at C-3 of quinovose residue. New glycosides
without lactone or with 18(16)-lactone and having shortened side chains have also been isolated. The presence of 17α and 12α-hydroxyls,
which are characteristic for glycosides from holothurians belonging to the family Holothuriidae (Aspidochirotida) in glycosides
of dendrochirotids confirms parallel and relatively independent character of evolution of glycosides. All three families belonging
to the order Aspidochirotida: Holothuriidae, Stichopodidae and Synallactidae have similar and parallel trends in evolution
of the glycosides carbohydrate chains, namely from non-sulfated hexaosides to sulfated tetraosides. Sets of aglycones in glycosides
from holothurians belonging to the genus Cucumaria (Cucumariidae, Dendrochirotida) are specific for each species. The carbohydrate chains are similar in all representatives
of the genus Cucumaria. 相似文献
18.
S.-C. Hu K. Hong Y.-C. Song J.-Y. Liu R.-X. Tan 《World journal of microbiology & biotechnology》2009,25(1):115-121
A marine Streptomyces sp. 060524 capable of hydrolyzing the glycosidic bond of isoflavone glycosides, was isolated by detecting its β-glucosidase activity. 5 isoflavone aglycones were isolated from culture filtrates in soybean meal glucose medium. They were
identified as genistein (1), glycitein (2), daidzein (3), 3′,4′,5,7-tetrahydroxyisoflavone (4), and 3′,4′,7-trihydroxyisoflavone (5), based on UV, NMR and mass spectral analysis. The Streptomyces can selectively hydroxylate at the 3′-position in the daidzein and genistein to generate 3′-hydroxydaidzein and 3′-hydroxygenistein,
respectively. The Strain biotransformed more than 90% of soybean isoflavone glycosides into their aglycones within 108 h.
3′-hydroxydaidzein and 3′-hydroxygenistein exhibited stronger cytotoxicity against K562 human chronic leukemia than daidzein
and genistein. 相似文献
19.
Eight lanthanide–copper coordination polymers of linear rigid 4-(4-pyridyl)benzoate(L1) and isonicotinate(L2), [LnCuI(L1)2(OAc) (H2O)]n (Ln = Pr, 1; Nd, 2; Sm, 3; Eu, 4; Gd, 5), [Ln2Cu4I3(L2)7 (H2O)]n (Ln = La, 6; Pr, 7), and [Nd2Cu7I6(L2)7 (H2O)6]n·2.5nH2O (8), were hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction. The three-dimensional frameworks of 1–5 can be described as wave-like layer modules of [Ln(L1)2(OAc)(H2O)]n linking with each other through dimeric units of Cu2I2, whereas that of compounds 6 and 7 are constructed by layer modules of and Cu4I3 clusters. As for 8, dimeric units of Nd2(L2)7(H2O)6 connect layered polymeric forming a 3D framework. 相似文献
20.
One novel bis(monoterpenoid) indole alkaloid glucoside, hirsutaside D (1), along with three known compounds, bahienoside A (2), bahienoside B (3) and neonaucleoside B (4), were isolated from the leaves of U. hirsuta. The structure of compound 1 was elucidated on the basis of extensive spectroscopic data analysis and chemical means. Characterization of compounds 2–4 was based on spectral analysis and comparison with the literature. Their cytotoxic effects on four human tumor cell lines were examined. 相似文献