ABSTRACT
Three new triterpenoids, 19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3- methyl ester (1), 19-hydroxy-1-oxo-2-nor-2,3-secours-12-ene-3,28-dioic acid (2), and (3beta,18alpha,19alpha)-3,28-dihydroxy-20,28-epoxyursan-24-oic acid (3), were isolated from the roots of Potentilla multicaulis. Their structures were elucidated on the basis of spectroscopic methods (IR, HR-ESI-MS, and 1D- and 2D-NMR). Compound 2b exhibited moderate cytotoxic activity against human promyelocytic leukemia (HL-60) cells.
Subject(s)
Potentilla/chemistry , Triterpenes/isolation & purification , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Molecular Structure , Spectrum Analysis , Triterpenes/chemistryABSTRACT
Four new labdane-type rhamnopyranosides derived from 13-epimanool, compounds 1-4, with differently acetylated sugar moieties, were isolated from A. veitchianus. Their structures and absolute configurations were elucidated by chemical transformation, spectroscopic and mass-spectrometric analyses (IR, 1D- and 2D-NMR, HR-ESI-MS), as well as by single-crystal X-ray diffraction (compound 1). The isolates 2-4 were investigated for their cytotoxic properties against cultured human hepatoma (SMMC-7721), ovarian neoplasm (HO-8910), and leukemia (HL-60) cells, and for their antibacterial activities against Escherichia coli, Bacillus subtilis, and Staphylococcus aureus.
Subject(s)
Aster Plant , Diterpenes/isolation & purification , Glycosides/isolation & purification , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Diterpenes/pharmacology , Glycosides/pharmacology , HL-60 Cells , Humans , Plant Extracts/isolation & purification , Plant Extracts/pharmacologyABSTRACT
A new iridoid (1) and thirteen known compounds 2-14 were isolated from Pedicularis kansuensis forma albiflora Li., and their structures were elucidated by spectroscopic methods including 2D-NMR techniques.
Subject(s)
Iridoids/isolation & purification , Pedicularis/chemistry , Iridoids/chemistry , Magnetic Resonance SpectroscopyABSTRACT
From the whole plants of Conyza canadensis (Compositae), a new C-10 acetylene, namely 8R, 9R-dihydroxymatricarine methyl ester (1), and a new triterpenoid, namely 3beta, 16beta, 20beta-trihydroxytaraxast-3-O-palmitoxyl ester (4), were isolated along with eleven known compounds (2, 3, 5-13). The structures of all 13 compounds were elucidated on the basis of their spectral data. The antibacterial activities of compounds 1-3 were evaluated.
Subject(s)
Alkynes/isolation & purification , Conyza/chemistry , Triterpenes/isolation & purification , Alkynes/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Triterpenes/chemistryABSTRACT
To study the effects of different reactive oxygen species (ROS) on the resting tension of porcine coronary artery rings and to identify the effects of genistein (GEN), resveratrol (RES) and 17beta-estradiol (EST) on ROS-elicited vasoconstriction, porcine coronary rings were prepared and mounted in an organ bath and, after an equilibration period, the changes induced by the drugs were observed. Rings with intact endothelium showed an obvious but slow contraction after treatment with xanthine (100 microM)/xanthine oxidase (20 mU x mL(-1)) (X/XO) whereas endothelium-denuded rings showed no effects. H2O2 (200 microM) induced a fast and transient contraction in endothelium-denuded rings and failed to do so in intact-endothelium rings. Like superoxide dismutase (SOD, 200 U x mL(-1)), GEN (1 microM) and RES (1 microM) significantly inhibited contractile response evoked by X/XO, however in contrast to GEN and RES, EST (1 microM) had no obvious effect. GEN (30 microM) and RES (30 microM), like catalase (CAT, 800 U x mL(-1)), markedly attenuated the contraction elicited by H2O2. The results demonstrate that GEN and RES have distinct inhibitory effects on vasoconstriction induced by O2*- generated by X/XO and H2O2, and their actions are clearly greater than to that of EST.
Subject(s)
Estradiol/pharmacology , Phytoestrogens/pharmacology , Reactive Oxygen Species/antagonists & inhibitors , Vasoconstriction/drug effects , Animals , Cattle , Coronary Vessels/drug effects , Genistein/pharmacology , Hydrogen Peroxide/antagonists & inhibitors , Hydrogen Peroxide/pharmacology , In Vitro Techniques , Muscle Contraction/drug effects , Muscle, Smooth, Vascular/drug effects , Oxygen/pharmacology , Reactive Oxygen Species/pharmacology , Resveratrol , Stilbenes/pharmacology , Superoxide Dismutase/pharmacologyABSTRACT
The present study was designed to investigate the acute relaxing effect of phytoestrogen resveratrol on isolated porcine coronary arteries and to determine the mechanisms underlying its vasodilatation. Rings of porcine coronary arteries were suspended in organ baths containing Krebs-Henseleit solution, and then isometric tension was measured. Resveratrol concentration-dependently relaxed arterial rings precontracted with 30 mM KCl. The IC(50) value of resveratrol was 38.67+/-3.21 microM. Incubation with N(omega)-L-nitro-arginine (L-NNA), endothelium removal or the presence of a potent inhibitor of protein tyrosine phosphatase sodium orthovanadate partly decreased the relaxation induced by resveratrol. However, the relaxation induced by resveratrol was unaffected by the estrogen receptor antagonist tamoxifen, the inhibitor of prostanoid synthesis indomethacin, the antagonist of beta-adrenoceptors propranolol or the protein synthesis inhibitor, cycloheximide. In addition, resveratrol significantly decreased the contractile responses of 5-HT, KCl and CaCl(2), and shifted their cumulative concentration-response curves to the right. These results suggest that the mechanisms of vasorelaxation induced by resveratrol are heterogeneous, two mechanisms participating partially in the relaxation of porcine coronary artery were detected in the study, one being the nitric oxide released from the endothelium, the other causing inhibition of Ca(2+) influx, but estrogen receptors were not involved in resveratrol-induced relaxation.
Subject(s)
Coronary Circulation/drug effects , Coronary Vessels/drug effects , Stilbenes/pharmacology , Vasodilation/drug effects , Vasodilator Agents/pharmacology , Animals , Calcium/metabolism , Dose-Response Relationship, Drug , Endothelium, Vascular/drug effects , Enzyme Inhibitors/pharmacology , Female , In Vitro Techniques , Male , Nitric Oxide/metabolism , Nitroarginine/pharmacology , Potassium Chloride/pharmacology , Prostaglandins/metabolism , Receptors, Adrenergic, beta/metabolism , Resveratrol , Serotonin/pharmacology , Serotonin Agents/pharmacology , SwineABSTRACT
From the roots of Leontopotium longifolium, three new bisabolane sesquiterpenes, rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-1,5-dimethylhexa-3,5-dienyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (1), rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (2), rel-(1R,2S,4R,5S)-4-acetoxy-2-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-5-methylcyclohexyl (Z)-2-methylbut-2-enoate (3), and a new coumarin, 2,3-dihydro-5-hydroxy-2-(1-methylethenyl)-7H-pyrano[2,3-g][1,4]benzodioxin-7-one (4) together with nine known compounds have been isolated. The structures of these compounds were established by spectroscopic methods. Compounds 1 and 2 exhibited moderate cytotoxic activities against human promyelocytic leukemia (HL-60) cells.
Subject(s)
Asteraceae/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/toxicity , Asteraceae/metabolism , Cell Survival/drug effects , HL-60 Cells , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Sesquiterpenes/metabolism , Sesquiterpenes/toxicityABSTRACT
Five new iridoids, namely rupesin A-E (1-5, resp.), together with six known iridoids, 6-11, were isolated from the roots of Patrinia rupestris. Their structures were elucidated by spectroscopic methods including IR, UV, MS, and 1D- and 2D-NMR experiments, and comparison with data of known analogues. Compounds 4 and 11, compounds 1, 2, 5, 6, 8, 9, and 10, and compounds 3, 4, and 8 showed significant antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus, respectively.
Subject(s)
Iridoids/chemistry , Iridoids/isolation & purification , Patrinia/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Escherichia coli/drug effects , Iridoids/pharmacology , Molecular Structure , Plant Roots/chemistry , Spectrum Analysis , Staphylococcus aureus/drug effectsABSTRACT
Two new benzofurans, 2-(1,2-dihydroxyisopropyl)-5,6-dimethoxybenzofuran (1) and 2-(1-O-feruloyl-2-hydroxyisopropyl)-5,6-dimethoxybenzofuran (2), along with eleven known compounds (3-13) were isolated from the roots of Ligularia przewalskii. Their structures were established on the basis of spectroscopic methods. The antibacterial activity of compounds 1 and 3-5 was tested.
Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Asteraceae/chemistry , Benzofurans/chemistry , Benzofurans/pharmacology , Bacteria/drug effects , Indicators and Reagents , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Plant Roots/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared , Spectroscopy, Fourier Transform InfraredABSTRACT
The purpose of this work was to examine the differential mechanisms involved in relaxation induced by genistein and 17-beta-estradiol in isolated porcine coronary arteries. Similar to 17-beta-estradiol, genistein could dose-dependently relax 30 mM KCI-precontracted coronary artery rings. The pD2 values of genistein and 17-beta-estradiol were 4.91 +/- 0.13 and 4.98 +/- 0.12 respectively. Incubation with N-L-nitroarginine (L-NNA), endothelium removal or in the presence of a potent inhibitor of protein tyrosine phosphatase sodium orthovanadate did not affect the relaxation induced by genistein, but could partially reduce the vasorelaxation induced by 17-beta-estradiol. The relaxations induced by genistein and 17-beta-estradiol were unaffected by the estrogen receptor antagonist tamoxifen, the inhibitor of prostanoid synthesis indomethacin and the protein synthesis inhibitor, cycloheximide. In addition, both of genistein and 17-beta-estradiol could decrease the contractile responses of KCI, 5-HT and CaCl2, and shift their cumulative concentration-response curves rightward in a parallel manner. These findings suggest that the relaxant effects induced by genistein and 17-beta-estradiol are probably mainly due to inhibition of Ca2+ influx through voltage-dependent calcium channels (VDCCs), and are not related to sex hormone receptor and classical genomic activities. Also there is an interesting finding that the relaxing response of 17-beta-estradiol is partially endothelium-dependent, but that of genistein is not.
Subject(s)
Coronary Vessels/drug effects , Estradiol/pharmacology , Genistein/pharmacology , Muscle, Smooth, Vascular/drug effects , Animals , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Calcium/physiology , Calcium Chloride/pharmacology , Dose-Response Relationship, Drug , Endothelium, Vascular/drug effects , Estrogen Antagonists/pharmacology , In Vitro Techniques , Muscle Contraction/drug effects , Potassium Chloride/pharmacology , Prostaglandin Antagonists/pharmacology , Protein Synthesis Inhibitors/pharmacology , Serotonin/metabolism , SwineABSTRACT
Two migrated ursane skeleton triterpenoids, one is D:B-friedoursane-3alpha,16alpha-dihydroxy-7alpha,8alpha-epoxy-5(10)-ene, named petatrichol A (1) and the other one represents a novel triterpenoid carbon framework, named petatrichol B (2), along with 10 known compounds were isolated from the rhizome of Petasites tricholobus. Their structures were elucidated on the basis of spectroscopic methods (IR, EIMS, HRMS, 1D and 2D NMR). The triterpenoids were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. Compounds 1 and 2 exhibited significant antibacterial activity against B. subtilis.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Petasites/chemistry , Triterpenes/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Bacillus subtilis/growth & development , Escherichia coli/drug effects , Escherichia coli/growth & development , Magnetic Resonance Spectroscopy , Molecular Structure , Rhizome/chemistry , Staphylococcus aureus/drug effects , Staphylococcus aureus/growth & development , Triterpenes/chemistry , Triterpenes/pharmacologyABSTRACT
Five new eremophilane sesquiterpenes, 3beta,6beta-diangeloyloxy-8beta,10beta-dihydroxyeremophilenolide (1); 6beta-acetoxy-3beta-angeloyloxy-8beta,10beta-dihydroxyeremophilenolide (2); 3beta-angeloyloxy-6beta-methoxyeremophil-7(11),9(10)-dien-8alpha,12-olide (3), 3beta-angeloyloxy-8-oxo-eremophil-6(7)-en-12-oic acid (4); 3beta-angeloyloxy-10beta-hydroxy-8-oxo-eremophil-6(7)-en-12-oic acid (5), and a novel nor-eremophilane derivative, 3beta-angeloyloxy-10beta-hydroxy-8-oxo-eremophil-6(7)-en (6), were isolated from the roots of Cacalia ainsliaeflora. Their structures were elucidated by spectroscopic methods, including 2DNMR. Compounds 1 and 2 were assayed against P388 and A549 Carcinoma cell lines. No positive activities were observed.
Subject(s)
Plants, Medicinal/chemistry , Sesquiterpenes/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Humans , Indicators and Reagents , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Plant Roots/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Spectrophotometry, InfraredABSTRACT
A new diterpene glycoside 1 was isolated from the whole plant of Aster homochlamydeus Hand-mazz (Compositae), along with four known diterpene glycosides 2-5. Their structures were elucidated by spectroscopic methods, MS, IR, NMR and X-raycrystallographic analyisis. Antibacterial activity of compounds 1-5 was observed.
Subject(s)
Asteraceae/chemistry , Diterpenes/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Carbohydrate Sequence , Crystallography, X-Ray , Diterpenes/isolation & purification , Diterpenes/pharmacology , Glycosides/chemistry , Glycosides/isolation & purification , Glycosides/pharmacology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Models, Molecular , Molecular Sequence Data , Spectrometry, Mass, Fast Atom Bombardment , Spectrophotometry, InfraredABSTRACT
From the methanol extract of the whole plant of Achillea wilsoniana, 23 compounds were isolated. Their structures were elucidated by spectroscopic methods and chemical transformations. Three of them are new: 4E, 10E-9beta-hydroxy-3-(2-methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (1), 4E,10E-3-(2-methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (2) and 1beta,6a-dihydroxy-10beta-methyl-5alphaH,7alphaH-eudesm-4-one (3). In addition, 1beta-hydroxy-alpha-xyperone (5) and 9beta-acetoxy-3-(2methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (1a) exhibited effective antibacterial activity against Staphylococcus aureus.
Subject(s)
Achillea/chemistry , Sesquiterpenes/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Chromatography, Thin Layer , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Plant Extracts/chemistry , Plant Extracts/pharmacology , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
Three new polymeric isopropenyl benzofurans, 4-methyl-2,4-bis(5,6-dimethoxy-2-benzofuranyl)-1-pentene, stenocephalin A (1), 4,6-dimethyl-2,4,6-tri(5,6-dimethoxy-2-benzofuranyl)-1-heptene, stenocephalin B (2) and 4,6,8-trimethyl-2,4,6,8-tetra(5,6-dimethoxy-2-benzofuranyl)-1-nonene, stenocephalin C (3), together with seven known compounds (4-10) were isolated from the roots of Ligularia stenocephala. The structures of the new compounds were elucidated on the basis of spectral evidence, especially on 2D NMR. In addition, the cytotoxic activity and the anti-bacterial activity of compounds 2, 3, 5 and 6 were tested.
Subject(s)
Alkenes/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Asteraceae/chemistry , Benzofurans/isolation & purification , Benzofurans/pharmacology , Heptanes/pharmacology , Alkenes/isolation & purification , Bacillus subtilis/drug effects , Cell Line, Tumor , Escherichia coli/drug effects , Heptanes/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Plant Roots/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Staphylococcus aureus/drug effectsABSTRACT
A new flavone glycoside, chrysoeriol 7-O-(2"-O-6'''-O-acetyl-beta-D-glucopyranosyl-beta-D-glucopyranoside (1), along with fourteen known compounds 2-15 were isolated from the whole plant of Carduus crispus Linn. Their structures were established on the basis of spectroscopic methods and chemical evidences. The antitumour activity of compound 1, 4 and 5 was tested. Compound 4 exhibited significant antitumour activity against HO-8901 (human ovarian neoplasm) cells.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Carduus/chemistry , Flavones/chemical synthesis , Glycosides/chemistry , Glycosides/chemical synthesis , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Chromatography, Thin Layer , Drug Screening Assays, Antitumor , Female , Flavones/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Humans , Hydrolysis , Indicators and Reagents , Magnetic Resonance Spectroscopy , Ovarian Neoplasms/drug therapy , Spectrometry, Mass, Fast Atom Bombardment , Spectrophotometry, UltravioletABSTRACT
OBJECTIVE: To study the constituents of Hypericum attenatum. METHOD: The compounds were isolated by chromatography on silica gel, the structures were identified by their physical, chemical properties and IR, NMR and MS spectral data respectively. RESULT: Nine compounds were isolated and identified as p-hydroxybenzoic acid (1), 6, 9-dihydroxy-4, 7-megastigmadien-3-one (2), butyl alcohol-O-alpha-D-fructoside (3), 24-ethyl-cholest-7-ene-3 beta, 5 alpha, 6 beta-thtroil (4), hexanol (5), 1 beta, 6 alpha-dihydroxyeudesmane-4(14)-ene (6), beta-sitosterol (7), 5, 5-dimethyl-4-hydroxy-tetrahydrofuran-2-one (8), beta-daucosterol (9). CONCLUSION: All of the compounds were isolated from H. attenuatum for the first time.
Subject(s)
Hexanols/isolation & purification , Hypericum/chemistry , Norisoprenoids/isolation & purification , Parabens/isolation & purification , Plants, Medicinal/chemistry , Hexanols/chemistry , Norisoprenoids/chemistry , Parabens/chemistry , Plant Components, Aerial/chemistryABSTRACT
A survey of the whole plant of Saussurea parviflora afforded three compounds 11,12,13-trihydroxy-4(15),8-eudesmadiene-9-one, eudesman-8beta,12-olide-1-O-beta-D-glucoside and 1beta,3beta-dihydroxyursa-9(11),12-diene-3-octadecanoate, as well as 13 known compounds. Their structures were elucidated on the basis of spectral evidence, especially by using NMR spectroscopic techniques. In addition, encelin exhibited effective antitumor activity on L02, SMMC-7721 and HO-8910 cells.
Subject(s)
Saussurea/chemistry , Sesquiterpenes, Eudesmane , Sesquiterpenes/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Carcinoma, Hepatocellular/drug therapy , Cell Survival/drug effects , Chemical Fractionation , Drug Screening Assays, Antitumor , Female , Humans , Liver Neoplasms/drug therapy , Nuclear Magnetic Resonance, Biomolecular , Ovarian Neoplasms/drug therapy , Plants, Medicinal/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Tumor Cells, CulturedABSTRACT
Two new compounds, a stigmasterol (1) and an eremophilenolide (2), were isolated from Ligularia dolichobotrys (Diels) together with ten known sesquiterpenoids, two known triterpenes and five known sterols. Their structures were elucidated by spectroscopic methods (IR, MS, 1H, 13C and 2D NMR). In addition, bakkenolide A (3) exhibited effective antitumor activity to human leukemia cells (HL-60), human hepatoma cells (Bel-7402) and human ovarian neoplasm cells (HO-8910).
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Asteraceae/chemistry , Stigmasterol/chemistry , Triterpenes , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Phytosterols/chemistry , Phytosterols/isolation & purification , Phytosterols/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Spectrophotometry, Infrared , Stigmasterol/isolation & purification , Stigmasterol/pharmacology , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacologyABSTRACT
Together with twenty-one known compounds, a new furobenzopyranone was isolated from the whole plant of Anaphalis lactea. Their structures were elucidated by spectroscopic methods MS, IR, UV, NMR, including 2D-NMR techniques. The anti-bacterial activity of compounds 1, 4-6, 14, 15 and the anti-tumor activity of compounds 4-6 were tested.