Three new triterpenoids from Potentilla multicaulis.

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.

Labdane diterpenoid glycosides from Aster veitchianus.

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.

A new iridoid and other chemical constituents from Pedicularis kansuensis forma albiflora Li.

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.

A new C-10 acetylene and A new triterpenoid from Conyza canadensis.

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.

Effects of phytoestrogens and 17beta-estradiol on vasoconstriction elicited by reactive oxygen species.

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.

A study of mechanisms involved in vasodilatation induced by resveratrol in isolated porcine coronary artery.

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.

New bisabolane sesquiterpenes and coumarin from Leontopodium longifolium.

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.

Five new iridoids from Patrinia rupestris.

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.

Two new benzofurans and other constituents from Ligularia przewalskii.

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.

Differential mechanisms involved in effects of genistein and 17-beta-estradiol on porcine coronary arteries.

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.

Two triterpenoids and other constituents from Petasites tricholobus.

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.

Six new sesquiterpenes from Cacalia ainsliaeflora.

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.

Diterpene glycosides from Aster homochlamydeus.

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.

Sesquiterpenes and other constituents from Achillea wilsoniana.

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.

Three new polymeric isopropenyl benzofurans from Ligularia stenocephala.

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.

A new flavone glycoside and other constituents from Carduus crispus.

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.

[Study on the chemical constituents in herb of Hypericum attenuatum].

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.

Eudesmane derivatives and other constituents from Saussurea parviflora.

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.

Two new compounds from Ligularia dolichobotrys.

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).

A new furobenzopyranone and other constituents from Anaphalis lactea.

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.