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1.
??OBJECTIVE To study the chemical constituents of the total flavonoids from Sophora flavescens and establish a method for simultaneous determination of seven compounds. METHODS The compounds were isolated by chromatography on silica gel and ODS column and their structures were elucidated by spectroscopic analysis. The samples were analyzed on a Dikma C18 column (4.6 mm??250 mm,5 ??m); gradient elution was performed using mobile phase composed of methanol (A)and water (B); the detection was carried out using a photodiode array detector at 280 nm. RESULTS Seven compounds were isolated and their structures were identified as kuratidine (1), sophoraflavanone G (2), kurarinone (3), isoanhydroicaritin (4), isoxanthohumol (5), formononetin (6), and trifolirhizin (7). The calibration curve was linear within 8.70-87.00, 44.25-442.50, 128.10-1 281.00, 9.40-94.00, 48.40-484.00, 14.20-142.00, and 25.70-257.00 ??g??mL-1 for kuraridine, sophoraflavanone G, kurarinone, isoanhydroicaritin, isoxanthohumol, formononetin, and trifolirhizin, respectively (r>0.999 0), and the extraction recoveries varied from 95% to 105%. CONCLUSION The main chemical components contributing to antibacterial activity of total flavonoids may be sophoraflavanone G, kurarinone, and isoxanthohumol. The method is simple, rapid, accurate, and can be used simultaneously to determine the contents of the seven active ingredients.  相似文献   

2.
Cytotoxic lavandulyl flavanones from Sophora flavescens   总被引:3,自引:0,他引:3  
Two new lavandulylated flavanones, (2S)-2'-methoxykurarinone (1) and (-)-kurarinone (2), were isolated from the root of Sophora flavescens, together with two known lavandulyl flavanones, sophoraflavanone G (3) and leachianone A (4), and two known isoflavonoids, formononetin and l-maakiain. The structures of 1 and 2 were determined on the basis of optical rotation and spectral evidence and by comparison with known compounds. Compounds 1-4 exhibited cytotoxic activity against human myeloid leukemia HL-60 cells.  相似文献   

3.
Bioassay-directed fractionation of an anti-inflammatory CHCl(3)-MeOH (9:1) extract of leaves of Vernonia colorata, using a carrageenan-induced rat paw model, led to the isolation of six new compounds (1-6).These were assigned as two new androst-8-en glycosides, 3-O-[beta-d-galactopyranosyl-(1-2)-[beta-d-glucopyranosyl-(1-->6)]-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (1) and 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (2), two new stigmastane-type glycosides, 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-glucopyranoside (3) and 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-(6-acetyl)glucopyranoside (4), and two new stigmastane-type steroids, 3beta,25,29-trihydroxy-5alpha-stigmasta-8(9),14(15),24Z(28)-triene (5) and 3beta,23,25-trihydroxy-24,28-epoxy-5alpha-stigmasta-8(9),14(15)-diene (6). The structures of 1-6 were elucidated by spectral and chemical studies. Compounds 1-6 were tested for the anti-inflammatory activity, but all were inactive or weakly inactive as anti-inflammatory agents.  相似文献   

4.
Objective: To study the chemical constituents from the roots of Curcuma longa. Methods: The structures of the new compounds were elucidated based on extensive spectral analysis, including 1D and 2D NMR, MS, UV, and CD analysis. Results: Two new sesquiterpene compounds (1S,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one (1), (1R,2R,5R,7S,8R)-2,8-epoxy-5-hydroxybisabola-3,10-dioen-9-one (2), and a new natural product 6-(4-Hydroxymethylphenyl)-2-methyl-hept-2-ene-4-one (3) together with three known compounds ar-turmerone (4), 2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one (5) and 2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one (6) were isolated from C. longa root extract with 95% ethanol. Conclusion: In the study, three new compounds were isolated from C. longa, and their absolute configurations were determined.  相似文献   

5.
A methanol extract of the pericarps of Illicium minwanense afforded seven new seco-prezizaane-type sesquiterpenes (2-8) and a new abietane-type diterpene (9), together with six previously known compounds (1 and 10-14). The structures of the new compounds, (1S)- and (1R)-minwanenone (2 and 3), 1alpha-hydroxy-6-deoxypseudoanisatin (4), (2S)-hydroxy-6-deoxypseudoanisatin (5), 3-oxopseudoanisatin (6), (3S,6R)-4,7-epoxy-6-deoxypseudoanisatin (7), 7-O-methylpseudomajucin (8), and (+)-8,11,13,15-abietatetraene (9), were elucidated by spectroscopic data analysis and chemical transformations. The absolute configurations of 1 and 5 were established by X-ray crystallographic analysis of their p-bromobenzoyl derivatives.  相似文献   

6.
In this study, sophoraflavanone G obtained from Sophora flavescens was evaluated against 10 clinical isolates of methicillin‐resistant Staphylococcus aureus (MRSA), either alone or in combination with ampicillin or oxacillin, via checkerboard assay. At the end point of an optically clear well, the minimum inhibitory concentrations (MICs) ranged from 0.5 to 8 µg/ml for sophoraflavanone G, from 64 to 1024 µg/ml for ampicillin, and from 256 to 1024 µg/ml for oxacillin. The combination of sophoraflavanone G and ampicillin or oxacillin yielded a fractional inhibitory concentration index ranging from 0.188 to 0.375, thereby indicating a principally synergistic effect. The synergistic interaction was verified by time‐kill studies using sophoraflavanone G and/or antibiotics. Thirty minutes of treatment with sophoraflavanone G with ampicillin or oxacillin resulted in an increase in the rate of killing in units of CFU/ml to a greater degree than was observed with Sophoraflavanone G alone. These findings indicated that the application of the tested sophoraflavanone G alone or in combination with antibiotics might prove useful in the control and treatment of MRSA infections. Copyright © 2009 John Wiley & Sons, Ltd.  相似文献   

7.
Six new (1-6) and three known (7-9) sesquiterpene esters were isolated from the roots of Celastrus orbiculatus. The structures of the new compounds were elucidated as 1beta-acetoxy-6alpha-furoyloxy-9alpha-benzoyl oxydihydro-beta-agarofur an (1), 1beta-acetoxy-6alpha-benzoyloxy-9alpha-furoyloxydih ydro-beta-agarofur an (2), 1beta-acetoxy-6alpha, 9alpha-difuroyloxydihydro-beta-agarofuran (3), 1beta, 2beta-diacetoxy-6alpha-furoyloxy-9alpha-benzo yloxydihydro-beta-agarof uran (4), 1beta-acetoxy-2beta, 6alpha-difuroyloxy-9alpha-benzoyloxydihydro-beta -agarofuran (5), and 1beta-acetoxy-2beta,6alpha, 9alpha-tribenzoyloxydihydro-beta-agarofuran (6). Compounds 4, 5, and 7-9 were shown to be more active than verapamil in reversing vinblastine resistance in multidrug-resistant KB-V1 cells.  相似文献   

8.
Six new mixed lignan-neolignans and 20 known compounds were isolated from the whole plant of Tarenna attenuata. By analysis of physical and spectroscopic data, the structures of the new compounds were elucidated as (1R,5R,6R)-6-{4-O-[2-(1-(4-hydroxy-3-methoxyphenyl))glycerol]-3,5-dimethoxyphenyl}-3,7-dioxabicyclo[3.3.0]octan-2-one (1), 5' '-methoxyhedyotisol A (2), 4' '-O-(8-guaiacylglycerol)buddlenol A (3), 5' '-methoxy-4' '-O-(8-guaiacylglycerol)buddlenol A (4), 4,6-dimethoxy-5-hydroxy-3-hydroxymethyl-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrobenzofuran (5), and 7-O-ethylguaiacylglycerol (6). Compounds 1, 5, 6, and 8 showed potent antioxidant activities against H2O2-induced impairment in PC12 cells, and compounds 1, 2, 5, and 7 scavenged DPPH radical strongly with IC50 values of 72, 87, 45, and 55 microM, respectively.  相似文献   

9.
Two new phenanthrenes ( 1 and 6) and four new dihydrophenanthrenes ( 2- 5) were isolated from a methanolic extract of Dendrobium nobile stems, along with 13 known phenanthrenes and dihydrophenanthrenes ( 7- 19). By spectroscopic analysis, the structures of compounds 1- 6 were determined as 2,8-dihydroxy-3,4,7-trimethoxyphenanthrene ( 1), 3-hydroxy-2,4,7-trimethoxy-9,10-dihydrophenanthrene ( 2), 2,8-dihydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene ( 3), 2-hydroxy-4,7-dimethoxy-9,10-dihydrophenanthrene ( 4), 2,2'-dihydroxy-3,3',4,4',7,7'-hexamethoxy-9,9',10,10'-tetrahydro-1,1'-biphenanthrene ( 5), and 2,3,5-trihydroxy-4,9-dimethoxyphenanthrene ( 6), respectively. Antifibrotic activity of compounds 1- 19 was evaluated employing HSC-T6, an immortalized rat hepatic stellate cell line, as an in vitro assay system by assessing cell proliferation.  相似文献   

10.
Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.  相似文献   

11.
Ma M  Zhao J  Wang S  Li S  Yang Y  Shi J  Fan X  He L 《Journal of natural products》2007,70(3):337-341
Three new bromophenols C-N coupled with nucleoside base derivatives (1-3) and three new brominated 1,2,3,4-tetrahydroisoquinolines (5-7), together with a new brominated tyrosine derivative (4), have been isolated from polar fractions of an ethanolic extract of the red alga Rhodomela confervoides. By spectroscopic and chemical methods including HRMS and 2D NMR data, their structures were determined as 7-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-3,7-dihydro-1H-purine-2,6-dione (1), 7-(2,3-dibromo-4,5-dihydroxybenzyl)-3,7-dihydro-1H-purine-2,6-dione (2), 9-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]adenine (3), (-)-8S-(3-bromo-5-hydroxy-4-methoxy)phenylalanine (4), (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5), methyl (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (6), and methyl (-)-3S-6-bromo-8-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (7). Compounds 5-7 were semisynthesized by using 4 as the starting material.  相似文献   

12.
From the methanol extract of Smilax bracteata rhizomes, six new phenolic compounds, (2S,3S)-5-O-beta-D-glucopyranosyloxy-6-methyl-3'-methoxy-3,7,3'-trihydroxyflavan (1), (2S,3S)-5-O-beta-D-glucopyranosyloxy-6-methyl-4'-methoxy-3,7,4'-trihydroxyflavan (2), 3beta-(3',5'-dihydroxyphenyl)-2alpha-(4' '-hydroxyphenyl)dihydrobenzofuran-5-carbaldehyde (3), (1-p-O-coumaroyl-6-O-feruroyl)-beta-D-fructofuranosyl-alpha-D-glucopyranoside (4), (1-p-O-coumaroyl-3,6-di-O-feruroyl)-beta-D-fructofuranosyl-alpha-D-glucopyranoside (5), and (6-O-feruroyl)-beta-D-fructofuranosyl-(6-O-acetyl)-alpha-D-glucopyranoside (6) were isolated together with five known compounds. Their structures were established by spectral data interpretation.  相似文献   

13.
Nine new phenolic compounds, 3S-hydrangenol 40-O-R-L-rhamnopyranoysl-(1-->3)-β-D-glucopyranoside (1), thunberginol F 7-O-β-D-glucopyranoside (2), 2-hydroxy-6-[2-(4-hydroxyphenyl)-2-oxo-ethyl]benzoic acid (3), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-oxo-ethyl]benzoic acid (4), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl-5-methoxy)-2-oxoethyl]benzoic acid (5), hydrangeic acid 40-O-β-D-glucopyranoside (6), E-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)dihydrofuran-2-one (7), Z-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)-2(3H)-furanone (8), and 4-[β-D-glucopyranosyl)hydroxy]-pinoresinol (9), and nine known compounds were isolated from the roots of Scorzonera judaica. Structures of 1-9 were elucidated by mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy.All compounds were evaluated for cytotoxic activity.  相似文献   

14.
Three new prenylated dihydrochalcones, (+/-)-nicolaioidesins A, B, and C (1-3), as well as a new natural product, 5-styrylfuran-2-carboxylic acid methyl ester (4), along with four known compounds, 2'-hydroxy-4',6'-dimethoxychalcone (5), (+/-)-5-hydroxy-7-methoxyflavanone (6), (+/-)-5-hydroxy-7,4'-dimethoxyflavanone, and panduratin A, were isolated from the roots of Renealmia nicolaioides, using a bioassay to determine the induction of quinone reductase (QR) activity with cultured Hepa lclc7 mouse hepatoma cells. Among these isolates, 5 and 6 induced QR activity, with observed concentrations to double activity (CD) values of 1.7 and 0.9 microg/mL, respectively, while the other constituents were not regarded as being active (CD >10 microg/mL). The chemical structures of 1-4 were elucidated by spectroscopic methods. A biogenetic pathway for the formation of (+/-)-nicolaioidins A-C (1-3) is proposed.  相似文献   

15.
Bioassay-directed fractionation of a methyl ethyl ketone extract of the roots of Endlicheria aff. resulted in the isolation of four new neolignans (1-4) and eight known compounds, namely, canellin A (5), canellin C (6), 3'-methoxyguianin (7), (7S,8R,1'S,5'S,6'R)-Delta(2',8')-3',6'-dihydroxy-5'-methoxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan (8), armenin-B (9), dillapiole (10), 1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene (11), and omega-hydroxyisodillapiole (12). The structures of the new compounds (1-4) were established as (7S,8R,1'S,5'S,6'R)-Delta(2',8')-5',6'-dihydroxy-3'-methoxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan, (7S,8R,1'S,5'S,6'R)-Delta(2',8')-3',5',6'-trihydroxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan, 2,4-dimethoxy-5,6-methylenedioxy-1-(2-propenyl)benzene, and 2,6-dimethoxy-3,4-methylenedioxycinnamyl alcohol, respectively, on the basis of spectroscopic interpretation.  相似文献   

16.
Three new phorbol esters, 12-(2-N-methylaminobenzoyl)-4beta,5,20-trideoxyphorbol-13-acetate (1), 12-(2-N-methylaminobenzoyl)-4alpha,5,20-trideoxyphorbol-13-acetate (2), and 12-(2-N-methylaminobenzoyl)-4alpha, 20-dideoxy-5-hydroxyphorbol-13-acetate (6), together with six known compounds (3-5 and 7-9), were isolated from the fruits of Sapium indicum. The chemical structures of 1, 2, and 6 were elucidated by analysis of their spectroscopic data. Compounds 1-3, 5, and 7-9 exhibited antimycobacterial activity with minimum inhibitory concentrations (MIC) between 3.12 and 200 microg/mL, but compounds 4 and 6 were inactive (MIC >200 microg/mL).  相似文献   

17.
The chloroform extract of rhizomes of Boesenbergia pandurata demonstrated marked preferential cytotoxicity against human pancreatic PANC-1 cancer cells in nutrient-deprived medium. Bioactivity-directed investigation of this extract yielded four new secondary metabolites, geranyl-2,4-dihydroxy-6-phenethylbenzoate ( 1), 2',4'-dihydroxy-3'-(1'-geranyl)-6'-methoxychalcone ( 2), (1' R,2' S,6' R)-2-hydroxyisopanduratin A ( 3), and (2 R)-8-geranylpinostrobin ( 4), and twenty known compounds ( 5- 24). Among the known compounds, (2 S)-6-geranylpinostrobin ( 5), (+/-)-6-methoxypanduratin A ( 6), and (2 S)-7,8-dihydro-5-hydroxy-2-methyl-2-(4'-methyl-3'-pentenyl)-8-phenyl-2 H,6 H-benzo[1,2- b:5,4- b']dipyran-6-one ( 7) were isolated for the first time from a natural source. The structures of these compounds were elucidated using extensive spectroscopic techniques including CD measurements. All the isolated compounds showed varying degrees of in vitro preferential cytotoxicity against PANC-1 cells. Nicolaioidesin B ( 11) and panduratin A ( 17) were most potent, each showing a PC 100 at 2.5 microM.  相似文献   

18.
New cytotoxic cyclic peptides and dianthramide from Dianthus superbus   总被引:1,自引:0,他引:1  
Four new cyclic peptides, dianthins C-F (1-4), and a new dianthramide, 4-methoxydianthramide B (5), were isolated from the MeOH extract of the traditional Chinese medicinal plant Dianthus superbus. The sequences of cyclic peptides 1-4 were elucidated as cyclo(Gly(1)-Pro(2)-Phe(3)-Tyr(4)-Val(5)-Ile(6)-), cyclo(Gly(1)-Ser(2)-Leu(3)-Pro(4)-Pro(5)-Ile(6)-Phe(7)-), cyclo(Gly(1)-Pro(2)-Ile(3)-Ser(4)-Phe(5)-Val(6)-), and cyclo(Gly(1)-Pro(2)-Phe(3)-Val(4)-Phe(5)-) on the basis of ESI tandem mass fragmentation analysis, chemical evidence, and extensive 2D NMR methods. The conformation of compound 1 was established as an alpha-helix by CD analysis. Furthermore, compounds 3 and 5 showed cytotoxicities toward the Hep G2 cancer cell line with IC(50) values of 2.37 and 4.08, respectively.  相似文献   

19.
Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2'-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1-11 were isolated from the ascidian collected in March (wet season), while 5-11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4-7 (1-4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 microM, respectively. Compounds 1-4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.  相似文献   

20.
Song F  Fan X  Xu X  Zhao J  Yang Y  Shi J 《Journal of natural products》2004,67(10):1644-1649
Seven new cadinane sesquiterpenes, (-)-(1R,6S,7S,10R)-1-hydroxycadinan-3-en-5-one (1), (+)-(1R,5S,6R,7S, 10R)-cadinan-3-ene-1,5-diol (2), (+)-(1R,5R,6R,7S,10R)-cadinan-3-ene-1,5-diol (3), (+)-(1R,5S,6R,7S,10R)-cadinan-4(11)-ene-1,5-diol (4), (+)-(1R,5R,6R,7R,10R)-cadinan-4(11)-ene-1,5,12-triol (5), (-)-(1R,4R,5S,6R,7S, 10R)-cadinan-1,4,5-triol (6), and (-)-(1R,6R,7S,10R)-11-oxocadinan-4-en-1-ol (7), together with nine known compounds were isolated from the brown alga Dictyopteris divaricata. The structures of the new natural products, as well as their absolute configuration, were established by means of spectroscopic data including IR, HRMS, 1D and 2D NMR, single-crystal X-ray diffraction, and CD. All compounds were inactive against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines.  相似文献   

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