ABSTRACT
A new guaianolide and a new eudesmanolide were isolated from Lactuca tatarica, as well as eight known sesquiterpenoids. The new compounds were elucidated on the basis of spectroscopic methods including IR, HRESIMS, 1D and 2D NMR, and the known compounds were established by comparing their physical data with those of the corresponding compounds in the literature.
Subject(s)
Lactuca/chemistry , Sesquiterpenes, Eudesmane/isolation & purification , Sesquiterpenes, Guaiane/isolation & purification , Molecular Structure , Plants, Medicinal/chemistry , Sesquiterpenes, Eudesmane/chemistry , Sesquiterpenes, Guaiane/chemistryABSTRACT
Four new oplopane and guaiane type sesquiterpenoids (1-3), and a monoterpenoid (4) together with three known monoterpenoids (5-7), have been isolated from the roots of Ligularia narynensis. The structures of 1-4 were elucidated as 3beta,4-diacetoxy-8alpha-(2-methylbutyryloxy)-9alpha-(4-methylsenecioyloxy)-11alpha,12-epoxyoplop-10 (14)-ene (1), 3beta,4-diacetoxy-9alpha-(4-acetoxy-4-methylsenecioyloxy)-2beta,8alpha-di (2-methylbutyryloxy)-11alpha,12-epoxyoplop-10 (14)-ene (2), 2alpha-hydroxy-1betaH,7alphaH,10alphaH-guai-4,11 (12)-dien-3-one (3) and 1alpha,2beta,3alpha,6alpha-tetrahydroxy-p-menthane (4) by spectroscopic methods. 1 and 2 were evaluated for their in vitro cytotoxic activity against cultured SMMC-7721 (human hepatoma), L02 (human hepatocyte), and HL-60 (human promyelocytic leukaemia) cell lines.
Subject(s)
Asteraceae/chemistry , Plant Roots/chemistry , Terpenes/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Humans , Molecular StructureABSTRACT
Pedicularioside G is a new compound of phenylpropanoid glycosides, isolated from Pedicularis striata in our laboratory. Pedicularioside G inhibited two major angiogenic responses, human umbilical vein endothelial cell proliferation and migration, as well as neovascularization in a chicken embryo chorioallantoic membrane model. In addition, pedicularioside G inhibited human hepatoma cells proliferation and migration in vitro along with transplanting tumour formation and growth in a chicken embryo chorioallantoic membrane model. So pedicularioside G has anti-angiogenic, antitumour growth, antimetastatic and antitumoural effects. Pedicularioside G also remarkably reduced reactive oxygen species level in both vein endothelial cells and hepatoma cells in a concentration-dependent manner. These results suggest that the anti-angiogenic and antitumoural effects of pedicularioside G might partially attribute to its antioxidative activity.
Subject(s)
Angiogenesis Inhibitors/pharmacology , Antioxidants/pharmacology , Drugs, Chinese Herbal/pharmacology , Glucosides/pharmacology , Iridoids/pharmacology , Liver Neoplasms/drug therapy , Neovascularization, Pathologic/drug therapy , Angiogenesis Inhibitors/chemistry , Animals , Antioxidants/chemistry , Carcinoma, Hepatocellular/drug therapy , Carcinoma, Hepatocellular/pathology , Cell Line, Tumor , Cell Movement/drug effects , Cell Proliferation/drug effects , Chick Embryo , Chorioallantoic Membrane/blood supply , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Endothelium, Vascular/drug effects , Endothelium, Vascular/pathology , Glucosides/chemistry , Humans , In Vitro Techniques , Iridoid Glucosides , Iridoids/chemistry , Liver Neoplasms/pathology , Pedicularis/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Reactive Oxygen Species/metabolismABSTRACT
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
Six new eremophilane sesquiterpenes, including a novel nortrieremophilane carbon skeleton, were isolated from the roots of Ligularia virgaurea. Their structures were elucidated as 3 alpha,4 alpha-epoxy-6 alpha-(2'-methylacryloyl)oxy-8 alpha-methoxyeremophil-7(11)-en-8 beta,12-olide (1), 3 alpha,4 alpha-epoxy-6 alpha-(2'-methylacryloyl)oxy-8 alpha-ethoxyeremophil-7(11)-en-8 beta,12-olide (2), 1 beta,10 beta-epoxy-6 beta-(2'-methylacryloyl)oxy-8 beta-methoxyeremophil-7(11)-en-8 alpha,12-olide (3), 1 beta,10 beta-epoxy-6 beta-angeloyloxy-8 beta-methoxyeremophil-7(11)-en-8 alpha,12-olide (4), 6 beta-methoxyeremophil-7(11)-en-8 beta,12-olide (5), and 5 beta-angeloyloxy-3a,4,5,6,7,7a-hexahydro-3a beta-methyl-1 H-indene-2,4 beta-dioic acid methyl ester (6) by spectral methods, including IR, HR-ESI-MS, 1D and 2D NMR techniques. All of compounds were evaluated for their in vitro cytotoxic activities against human hepatoma (SMMC-7721), human promyelocytic leukemia (HL-60), and human hepatocyte (L-02) cells.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Asteraceae , Phytotherapy , Plant Extracts/pharmacology , Antineoplastic Agents, Phytogenic/administration & dosage , Antineoplastic Agents, Phytogenic/therapeutic use , Cell Line, Tumor/drug effects , Humans , Naphthalenes/administration & dosage , Naphthalenes/pharmacology , Naphthalenes/therapeutic use , Plant Extracts/administration & dosage , Plant Extracts/therapeutic use , Plant Roots , Polycyclic Sesquiterpenes , Sesquiterpenes/administration & dosage , Sesquiterpenes/pharmacology , Sesquiterpenes/therapeutic useABSTRACT
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
Four new highly oxygenated germacranolides (1, 4, 6, and 7) and four new acyclic diterpenes (8-11), along with three known germacranolides (2, 3, and 5), were isolated from the seeds of Carpesium triste. The structures of the new compounds were elucidated by spectroscopic methods including IR, HRESIMS, and 1D and 2D NMR experiments, and the absolute configurations of compounds 1 and 8-10 were established by CD and Mosher's methods, respectively. Compounds 1, 2, and 4-10 were evaluated for their in vitro cytotoxic activity against cultured SMMC-7721 (human hepatoma), HL-60 (human promyelocytic leukemia), and L02 (human hepatocyte) cell lines. Compounds 1, 2, and 4-7 exhibited significant cytotoxicity against HL-60 cells, and compound 10 exhibited cytotoxicity against SMMC-7721 cells.
Subject(s)
Antineoplastic Agents, Phytogenic , Asteraceae/chemistry , Diterpenes , Drugs, Chinese Herbal , Plants, Medicinal/chemistry , Sesquiterpenes, Germacrane , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/chemistry , Diterpenes/isolation & purification , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , HL-60 Cells , Humans , Molecular Structure , Seeds/chemistry , Sesquiterpenes, Germacrane/chemistry , Sesquiterpenes, Germacrane/isolation & purification , Sesquiterpenes, Germacrane/pharmacologyABSTRACT
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
Using the MTT assay and the telomeric repeat amplification protocol (TRAP)-based PCR-ELISA assay, the cytotoxicity and telomerase inhibiting ability of 17 sesquiterpenes (extracted from Chinese herbs) were tested in the human ovarian cancer cell line HO-8910. The results indicated that seven sesquiterpenes inhibited cell proliferation without having an effect on telomerase activity; two sesquiterpenes inhibited neither cell proliferation nor telomerase activity; and the other eight sesquiterpenes inhibited both cell proliferation and telomerase activity to a certain extent. Without exception, none of these 17 sesquiterpenes could only inhibit telomerase activity without inhibiting cell proliferation. This indicated that the telomerase inhibiting activity is not a universal mechanism for all anticancer drugs but is only one of several possible mechanisms. The structure-activity relationships of 5 groups of sesquiterpenes are also discussed. This study may help to develop anticancer drugs.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Ovarian Neoplasms/drug therapy , Plants, Medicinal/chemistry , Sesquiterpenes/pharmacology , Telomerase/metabolism , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Enzyme-Linked Immunosorbent Assay , Female , Humans , Ovarian Neoplasms/enzymology , Polymerase Chain Reaction , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Structure-Activity Relationship , Telomerase/antagonists & inhibitorsABSTRACT
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
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
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
This review covers the structures and biological activities of eudesmane-type sesquiterpenoids from the plants of the Asteraceae family. Biosynthetic studies or chemical syntheses leading to the revision of structures or stereochemistries have also been included, and 593 references are cited.
Subject(s)
Asteraceae/chemistry , Plants, Medicinal/chemistry , Sesquiterpenes, Eudesmane , Medicine, Traditional , Molecular Structure , Sesquiterpenes, Eudesmane/chemistry , Sesquiterpenes, Eudesmane/isolation & purification , Sesquiterpenes, Eudesmane/pharmacologyABSTRACT
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 chemical investigation of Mulgedium tataricum afforded six new compounds which were identified as lanost-9(11),23 Z(24)-diene-3beta,25-diol (1), lanost-9(11),25-diene-3beta,24beta-diol (2), ursane-20-ene-3beta,22alpha-diol (3), 4 E,10 E-3beta,11beta-dihydroxygermacra-4(5),10(1)-dien-12,6alpha-olide (4), 4 E-1beta-hydroperoxy-3beta,11beta-dihydroxygermacra-4(5),10(14)-dien-12,6alpha-olide (5) and lactucin-8-O-P-methoxyphenyl acetate (6) by using a combination of MS and NMR techniques. Compound 6 exhibited significant cytotoxicity against cultured human hepatoma cells (SMMC-7721) and human acute promyelocytic leukemia cells (HL60). The antibacterial activity study indicated that 1 and 2 strongly inhibited the growth of Escherichia coli.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Asteraceae , Phytotherapy , Plant Extracts/pharmacology , Anti-Bacterial Agents/administration & dosage , Anti-Bacterial Agents/therapeutic use , Antineoplastic Agents, Phytogenic/administration & dosage , Antineoplastic Agents, Phytogenic/therapeutic use , Cell Line, Tumor/drug effects , Escherichia coli/drug effects , HL-60 Cells/drug effects , Humans , Microbial Sensitivity Tests , Plant Extracts/administration & dosage , Plant Extracts/therapeutic use , Sesquiterpenes/administration & dosage , Sesquiterpenes/pharmacology , Sesquiterpenes/therapeutic use , Triterpenes/administration & dosage , Triterpenes/pharmacology , Triterpenes/therapeutic useABSTRACT
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
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
Two new eremophilane-type sesquiterpenes, 3beta-(2'-methylbutanoyloxy)-8betaH-eremophil-7(11)-ene-12,8alpha-(14,6alpha)-diolide (1) and 8betaH-eremophil-3,7(11)-diene-12,8alpha(14,6alpha)-diolide (2), and two new norursane-type triterpenes, 2alpha,3beta,19alpha-trihydroxy-28-norurs-12-ene (7) and 2alpha,3alpha,19alpha-trihydroxy-28-norurs-12-ene (8), were isolated from the roots of Ligularia tongolensis, together with nine known compounds. The structures of the new compounds were elucidated by spectroscopic methods.
Subject(s)
Asteraceae/chemistry , Sesquiterpenes/chemistry , Triterpenes/chemistry , Asteraceae/classification , Carbon Isotopes , Drug Evaluation, Preclinical , Magnetic Resonance Spectroscopy/methods , Magnetic Resonance Spectroscopy/standards , Molecular Conformation , Plant Roots/chemistry , Protons , Reference Standards , Sesquiterpenes/isolation & purification , Triterpenes/isolation & purificationABSTRACT
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.