ABSTRACT
Buyang Huanwu decoction (BHD) was reported to exert angiogenesis-promoting effects, but its active ingredients remain unknown. In this study, we developed a method to screen potential angiogenesis-promoting compounds in BHD, which involved biospecific isolation using live rat brain microvascular endothelial cells (rBMECs) and characterization using solid-phase extraction (SPE) and high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). Six compounds showed binding affinity to rBMECs and were further identified as 6-hydroxykaempferol-di-O-glucoside, paeoniflorin, calycosin-7-O-ß-D-glucoside, galloylpaeoniflorin, formononetin-7-O-ß-D-glucoside, and (3R)-7,2'-hydroxy-3',4'-dimethoxy-isoflavan. The results indicated that five of them except 6-hydroxykaempferol-di-O-glucoside showed a protective effect against oxygen glucose deprivation/reperfusion injury in rBMECs and upregulated the secretion of vascular endothelial growth factor and basic fibroblast growth factor, suggesting a mechanism underlying their angiogenic activity. Our findings suggest that biospecific live cell-based isolation combined with SPE and HPLC-MS/MS is an effective method for screening potential bioactive components in traditional Chinese medicines.
Subject(s)
Angiogenesis Inducing Agents/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Drugs, Chinese Herbal/chemistry , Endothelial Cells/drug effects , Glucosides/isolation & purification , Isoflavones/isolation & purification , Monoterpenes/isolation & purification , Angiogenesis Inducing Agents/chemistry , Angiogenesis Inducing Agents/pharmacology , Animals , Animals, Newborn , Brain/blood supply , Brain/cytology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Chromatography, High Pressure Liquid/methods , Endothelial Cells/cytology , Endothelial Cells/metabolism , Glucosides/chemistry , Glucosides/pharmacology , Isoflavones/chemistry , Isoflavones/pharmacology , Monoterpenes/chemistry , Monoterpenes/pharmacology , Primary Cell Culture , Rats , Rats, Sprague-Dawley , Solid Phase Extraction/methods , Tandem Mass Spectrometry/methodsABSTRACT
A new compound, (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [b]furan-2-one (2), along with two known metabolites, myrotheciumone A (1) and 4-oxo-4H-pyron-3-acetic acid (3) was isolated from the ethyl acetate extract of fermentation broth of Xylaria curta 92092022. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HRESITOFMS, 1D NMR, and 2D NMR). Compounds 1 and 2 showed moderate antibacterial and phytotoxic activities.
Subject(s)
Anti-Bacterial Agents/pharmacology , Lactones/chemistry , Xylariales/chemistry , Acetates/chemistry , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Cyclopentanes/chemistry , Drug Evaluation, Preclinical , Endophytes/chemistry , Fermentation , Furans/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Lactuca/drug effects , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrones/chemistry , Spectrophotometry, Ultraviolet , Toxicity TestsABSTRACT
Nine new compounds, together with 16 known analogs, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of their spectroscopic data and chemical evidence. In addition, the new compounds were tested for their hepatoprotective activities against APAP-induced HepG2 cell damage and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line. Compounds 2 and 5 exhibited pronounced hepatoprotective activities against APAP-induced HepG2 cell damage at a concentration of 10 µM, and compounds 4 and 9 showed moderate inhibitory activity against microglial inflammation factor with IC50 values of 3.51 and 7.11 µM, respectively.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Glycosides/isolation & purification , Rehmannia/chemistry , Animals , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Glycosides/chemistry , Glycosides/pharmacology , Hep G2 Cells , Humans , Lipopolysaccharides/pharmacology , Liver/drug effects , Mice , Microglia/drug effects , Molecular Structure , Nitric Oxide/biosynthesisABSTRACT
Two new bicyclic lactones, myrotheciumones A (1) and B (2) which possessed a rare ring-fusion system were isolated from Myrothecium roridum (M. roridum), an endophytic fungus of the medicinal herb plant Ajuga decumbens (A. decumbens) via an in vitro cytotoxicity assay. Structures were deduced from 1D and 2D NMR (Nuclear magnetic resonance) data. Myrotheciumone A's in vitro cytotoxicity and apoptotic activity were evaluated and myrotheciumone A was shown to exert cytotoxicity via inducing apoptosis in cancer cell line.
Subject(s)
Ajuga/microbiology , Antineoplastic Agents/pharmacology , Ascomycota/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Lactones/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Apoptosis/drug effects , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Hep G2 Cells , Humans , Lactones/chemistry , Lactones/isolation & purification , Molecular Structure , Structure-Activity RelationshipABSTRACT
CONTEXT: Veronicastrum axillare (Sieb. et Zucc.) Yamazaki (Scrophulariaceae) embraces varieties of bioactivities such as anti-inflammatory, anti-pyresis and detoxification activity, while little is known of the phytochemical components of this medicinal plant. OBJECTIVE: To isolate and identify bioactive constituents from the whole herb of V. axillare. MATERIALS AND METHODS: Ethanol extract of the whole herb of V. axillare was subjected to successive column chromatography. Chemical structures of the compounds were elucidated by detailed spectroscopic analyses on the basis of NMR, IR and HR-MS data. RESULTS: A new monoterpenoid, axillacetal A (1) and a known analogue, tarumal (2), were isolated from the whole herb of V. axillare. The structure of tarumal (2) was also revised according to our NMR data. DISCUSSION AND CONCLUSION: This is the first report on the isolation and authentication of novel chemical constituents from V. axillare.
Subject(s)
Acetates/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Monoterpenes/isolation & purification , Scrophulariaceae/chemistry , Chromatography, Thin Layer , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular StructureABSTRACT
Seven new neolignanamides (1-7), including two pairs of cis- and trans-isomers, and a new lignanamide (8) were isolated from the EtOAc-soluble fraction of an EtOH extract of the root bark of Lycium chinense, together with 22 known phenolic compounds (9-30), four of which were obtained from the genus Lycium for the first time. Compounds 5, 6, and 7 are unusual dimers having a rare connection mode between the two cinnamic acid amide units, while compounds 6, 7, and 8 are the first naturally occurring dimers derived from two dissimilar cinnamic acid amides. The cinnamic acid amides, neolignanamides, and lignanamides possess moderate radical-scavenging activity against the DPPH (2,2-diphenyl-1-picrylhydrazyl) and superoxide radicals.
Subject(s)
Acrylamides/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Free Radical Scavengers/isolation & purification , Lycium/chemistry , Naphthalenes/isolation & purification , Acrylamides/chemistry , Acrylamides/pharmacology , Biphenyl Compounds/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Molecular Structure , Naphthalenes/chemistry , Naphthalenes/pharmacology , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Picrates/pharmacology , Plant Bark/chemistry , StereoisomerismABSTRACT
Chemical investigation of the water extracts from the Senecio cannabifolius Less. led us to find two new compounds (1 and 2), along with 12 known compounds (3-14). The two new compounds were determined as (E, 4R)-4-hydroxy-4,5,5-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enone (1) and (E)-4-((1S, 3R, 4R)-1-hydroxy-4,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-1-en-3-o-ne (2), respectively. The structures of other compounds were elucidated by extensive analysis of spectral data and in comparison with the literature values. Compounds 1 and 2 were evaluated for inhibitory activity against lipopolysaccharide-induced NO production in RAW 264.7 macrophages, and compound 1 showed potent inhibitory activity with IC(50) value of 30.65 µM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Cyclohexanones/isolation & purification , Senecio/chemistry , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Cyclohexanones/chemistry , Cyclohexanones/pharmacology , Drugs, Chinese Herbal , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Mice , Molecular Structure , Nitric Oxide , Nuclear Magnetic Resonance, Biomolecular , StereoisomerismABSTRACT
Hypnophilin and panepoxydone, terpenoids isolated from Lentinus strigosus, have significant inhibitory activity on Trypanosoma cruzi trypanothione reductase (TR). Although they have similar TR inhibitory activity at 10 µg/mL (40.3 µM and 47.6 µM for hypnophilin and panepoxydone, respectively; ~100%), hypnophilin has a slightly greater inhibitory activity (~71%) on T. cruzi amastigote (AMA) growth in vitro as well as on in vitro phytohemagglutinin (PHA)-induced peripheral blood mononuclear (PBMC) proliferation (~70%) compared to panepoxydone (69% AMA inhibition and 91% PBMC inhibition). Hypnophilin and panepoxydone at 1.25 µg/mL had 67% inhibitory activity onLeishmania (Leishmania) amazonensis amastigote-like (AMA-like) growth in vitro. The panepoxydone activity was accompanied by a significant inhibitory effect on PHA-induced PBMC proliferation, suggesting a cytotoxic action. Moreover, incubation of human PBMC with panepoxydone reduced the percentage of CD16(+) and CD14(+) cells and down-regulated CD19(+), CD4(+) and CD8(+) cells, while hypnophilin did not alter any of the phenotypes analyzed. These data indicate that hypnophilin may be considered to be a prototype for the design of drugs for the chemotherapy of diseases caused by Trypanosomatidae.
Subject(s)
Antiprotozoal Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Leishmania/drug effects , Lentinula/chemistry , Plant Extracts/pharmacology , Sesquiterpenes/pharmacology , Trypanosoma cruzi/drug effects , Antigens, CD/drug effects , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Cell Proliferation/drug effects , Drug Design , Humans , Leukocytes, Mononuclear/drug effects , Sesquiterpenes/isolation & purificationABSTRACT
Hypnophilin and panepoxydone, terpenoids isolated from Lentinus strigosus, have significant inhibitory activity onTrypanosoma cruzi trypanothione reductase (TR). Although they have similar TR inhibitory activity at 10 μg/mL (40.3 μM and 47.6 μM for hypnophilin and panepoxydone, respectively; ~100 percent), hypnophilin has a slightly greater inhibitory activity (~71 percent) on T. cruzi amastigote (AMA) growth in vitro as well as on in vitro phytohemagglutinin (PHA)-induced peripheral blood mononuclear (PBMC) proliferation (~70 percent) compared to panepoxydone (69 percent AMA inhibition and 91 percent PBMC inhibition). Hypnophilin and panepoxydone at 1.25 μg/mL had 67 percent inhibitory activity onLeishmania (Leishmania) amazonensis amastigote-like (AMA-like) growth in vitro. The panepoxydone activity was accompanied by a significant inhibitory effect on PHA-induced PBMC proliferation, suggesting a cytotoxic action. Moreover, incubation of human PBMC with panepoxydone reduced the percentage of CD16+ and CD14+ cells and down-regulated CD19+, CD4+ and CD8+ cells, while hypnophilin did not alter any of the phenotypes analyzed. These data indicate that hypnophilin may be considered to be a prototype for the design of drugs for the chemotherapy of diseases caused by Trypanosomatidae.
Subject(s)
Humans , Antiprotozoal Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Leishmania/drug effects , Lentinula/chemistry , Plant Extracts/pharmacology , Sesquiterpenes/pharmacology , Trypanosoma cruzi/drug effects , Antigens, CD/drug effects , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Cell Proliferation/drug effects , Drug Design , Leukocytes, Mononuclear/drug effects , Sesquiterpenes/isolation & purificationABSTRACT
Three unique phenylpropanoyl 2,7-anhydro-3-deoxy-2-octulosonic acid derivatives were isolated from Conyza canadensis (horseweed). Their structures were defined as rel-(1S,2R,3R,5S,7R)-methyl 7-caffeoyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (1), rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (2), and rel-(1R,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-feruloyloxy-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate (3). Compound 1 and a 5:3 mixture of compounds 2 and 3 were demonstrated to inhibit the catecholamine secretion induced by acetylcholine with IC(50) values of 94.65 and 42.35 microM, respectively, and to inhibit the catecholamine secretion induced by veratridine and high [K(+)] at a dose of 100 microM in cultured bovine adrenal medullary cells.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Conyza/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Phenylpropionates/isolation & purification , Phenylpropionates/pharmacology , Adrenal Medulla/cytology , Adrenal Medulla/drug effects , Animals , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Catecholamines/metabolism , Cattle , Drugs, Chinese Herbal/chemistry , Esters , Inhibitory Concentration 50 , Phenylpropionates/chemistry , Stereoisomerism , Veratridine/pharmacologyABSTRACT
Four new macrophyllin-type bicyclo[3.2.1]octanoid neolignans, (7S,8R,3'S,5'R)-Delta(8')-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2',4'-dioxo-7.3',8.5'-neolignan (cinerin A), 1, (7R,8R,3'S,4'R,5'R)-Delta(8')-4'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin B), 2, (7S,8R,3'R,4'S,5'R)-Delta(8')-4'-hydroxy-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin C), 3, and (7S,8R,2'R,3'S,5'R)-Delta(8')-2'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-4'-oxo-7.3',8.5'-neolignan (cinerin D), 4, along with the known diterpene kaurenoic acid 5, were isolated from the leaves of Pleurothyrium cinereum. The structures and configuration of these compounds were determined by extensive spectroscopic analysis. Cinerins A-D (1-4) were tested for their inhibition efficacy of platelet activating factor (PAF)-induced aggregation of rabbit platelets. Compound 3 was the most potent PAF antagonist. Compounds 1-5 were tested against Mycobacterium tuberculosis (H(37)Rv strain) using the MABA method. Compound 5 induced 91.3% growth inhibition at 50 microg mL(-1). Compounds 1-5 showed no significant inhibitory activity against some Gram-positive and Gram-negative bacteria by the agar-well diffusion method.
Subject(s)
Antitubercular Agents/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Lauraceae/chemistry , Lignans/isolation & purification , Mycobacterium tuberculosis/drug effects , Plants, Medicinal/chemistry , Platelet Activating Factor/antagonists & inhibitors , Animals , Antitubercular Agents/chemistry , Antitubercular Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Colombia , Lignans/chemistry , Lignans/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Plant Leaves/chemistry , Rabbits , StereoisomerismABSTRACT
Forsythia suspensa (Thunb.) Vahl. has been widely used in traditional medicines in Asia to treat gonorrhoea, erysipelas, inflammation, pyrexia, ulcer and other diseases. Recently the investigation has been focused on the antioxidant and antibacterial activity of this plant. However, limited scientifically proven information is available. We isolated two compounds (forsythiaside and forsythin) from this plant. The aims of this investigation, therefore, were to assay antioxidant activity and antibacterial properties of the two main and distinctive compounds isolated and to exploit antioxidants and antibacterial agents from natural compounds. The antioxidant activity was estimated using the 1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity method and the in-vitro antimicrobial activity was evaluated by microtitre plate method. Forsythiaside was found to possess strong antioxidant and antibacterial activity but forsythin was much weaker. Owing to these properties, the study can be further extended to exploit the possible application of forsythiaside as an alternative antioxidant and antibacterial agent of natural origin.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antioxidants/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Forsythia/chemistry , Furans/pharmacology , Glycosides/pharmacology , Biphenyl Compounds , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Drugs, Chinese Herbal , Escherichia coli/drug effects , Free Radical Scavengers/isolation & purification , Free Radical Scavengers/pharmacology , Furans/isolation & purification , Glycosides/isolation & purification , Medicine, East Asian Traditional , Microbial Sensitivity Tests , Picrates , Plant Extracts , Pseudomonas aeruginosa/metabolism , Staphylococcus aureus/drug effectsABSTRACT
Two new bicyclic polyketide lactones, polyrhacitides A ( 1) and B ( 2), were isolated from Chinese medicinal ants, Polyrhacis lamellidens, which have been used as an effective therapeutic agent to treat rheumatoid arthritis and hepatitis in China. Their absolute structures were elucidated on the basis of spectroscopic analyses and chemical evidence. The occurrence of polyketides with similar structures in plants of the Lamiaceae, Lauraceae, and Staphyleaceae indicates their significance in the study of chemical ecology.
Subject(s)
Ants/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Lactones/isolation & purification , Lactones/pharmacology , Animals , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Lactones/chemistry , Molecular Structure , Plants, Medicinal/chemistryABSTRACT
The skin of Bufo bufo gargarizans, originated from Bufo bufo gargarizans Cantor (Bufonidae), is widely used in traditional Chinese medicine for the treatment of hepatoma, lung cancer and etc. The preparation of the aqueous components has significant therapeutic effect against the digestive tract cancer. The water-soluble chemical constituents in the skin of Bufo bufo gargarizans were then investigated to make clear the active compounds. Six compounds were isolated and purified by recrystallization and column chromatography on silica gel and ODS, their structures were elucidated as 4-amido-3-hydroxymethyl-cyclooctylamidezotetra-alpha-furanone (I), bufogargarizanine C (II), bufothionine (III), dehydrobufotenine hydrobromide (IV), suberic acid (V) and succinic acid (VI) on the basis of physicochemical properties and spectral data (UV, IR, 1H NMR, 13C NMR and MS). Of the above compounds, compounds I and II are new compounds and named bufogargarizanine B and C, respectively.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bufo bufo , Skin/chemistry , Animals , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Caprylates/chemistry , Caprylates/isolation & purification , Dicarboxylic Acids/chemistry , Dicarboxylic Acids/isolation & purification , Medicine, Chinese Traditional , Molecular Conformation , Molecular StructureABSTRACT
Apicularens A and B were isolated from the myxobacterial genus Chondromyces apiculatus JW184. Apicularen A inhibited bafilomycin A1-sensitive ATP-dependent proton transport into microsome vesicles more potently than apicularen B. Bone resorption in cultures of mouse calvariae induced by human parathyroid hormone (PTH) or interleukin-1beta (IL-1beta) was inhibited by apicularen A at 10 and 100 nM, while apicularen B had no effect. The bisphosphonate incadronate inhibited bone resorption at 100 nM, being less effective than apicularen A. Our findings indicate that apicularen A inhibits bone resorption induced by PTH or IL-1beta more potently than apicularen B, probably due to inhibition of the V-ATPase.
Subject(s)
Bone Resorption , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Myxococcales/chemistry , Animals , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Diphosphonates/chemistry , Diphosphonates/pharmacology , Humans , Macrolides/chemistry , Macrolides/isolation & purification , Macrolides/pharmacology , Mice , Parathyroid Hormone/pharmacology , Skull/drug effects , Vacuolar Proton-Translocating ATPases/antagonists & inhibitorsABSTRACT
Three new water-soluble constituents [ficuscarpanoside B (1), (7E,9Z)-dihydrophaseic acid 3-O-beta-D-glucopyranoside (4) and ficuscarpanic acid (6)] and the natural product 2,2'-dihydroxyl ether (7) have been isolated, together with three known compounds [(7S,8R)-syringoylglycerol (2), (7S,8R)-syringoylglycerol-7-O-beta-D-glucopyranoside (3) and icariside D2 (5)] from the aerial roots of Ficus microcarpa. Identification of their structures was achieved by 1D and 2D NMR experiments, including 1H-1H COSY, NOESY, HMQC and HMBC methods and FAB mass spectral data.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic/chemistry , Dicarboxylic Acids/chemistry , Fatty Acids, Unsaturated/chemistry , Ficus/chemistry , Glucosides/chemistry , Glycosides/chemistry , Plant Growth Regulators/chemistry , Plant Roots/chemistry , Plants, Medicinal/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Chromatography , Dicarboxylic Acids/isolation & purification , Fatty Acids, Unsaturated/isolation & purification , Glucosides/isolation & purification , Glycosides/isolation & purification , Molecular Structure , Plant Growth Regulators/isolation & purification , Spectrophotometry , TaiwanABSTRACT
Four new styryl-lactones, crassalactones A-D (1-4), were isolated from a cytotoxic ethyl acetate-soluble extract of the leaves and twigs of Polyalthia crassa, together with seven known compounds, (+)-3-acetylaltholactone, (+)-altholactone, aristolactam AII, cinnamic acid, (+)-goniofufurone, (+)-goniopypyrone, and (+)-howiinol A. Their structures were determined on the basis of spectroscopic methods. The absolute configuration of 1-3 was established by chemical conversions. Single-crystal X-ray analysis and the Mosher ester method were used to confirm the absolute stereochemistry of 4. Cytotoxic evaluation against several mammalian cancer cell lines was performed on all new isolates, aristolactam AII, and the modified (+)-tricinnamate derivative 11 obtained from 1.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Lactones/isolation & purification , Lactones/pharmacology , Plants, Medicinal/chemistry , Polyalthia/chemistry , Animals , Antineoplastic Agents, Phytogenic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Drug Screening Assays, Antitumor , Humans , Lactones/chemistry , Molecular Structure , Plant Leaves/chemistry , Plant Stems/chemistry , Rats , ThailandABSTRACT
Three new alkaloids, lycopodatines A (1), B (2), and C (3), have been isolated from the club moss Lycopodium inundatum, and the structures and absolute configuration were elucidated on the basis of 2D NMR data and chemical transformation.
Subject(s)
Alkaloids/chemistry , Alkaloids/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Lycopodium/chemistry , Plants, Medicinal/chemistry , Japan , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularSubject(s)
Antineoplastic Agents/pharmacology , Cantharidin/pharmacology , Coleoptera/chemistry , Materia Medica/pharmacology , Animals , Antineoplastic Agents/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Cantharidin/isolation & purification , Humans , Lymphocyte Culture Test, Mixed , Materia Medica/isolation & purificationABSTRACT
Monomelittoside, melittoside, 8-acetyl-harpagide, harpagide, ajugol, 5-desoxy-harpagide, 5-desoxy-8-acetylharpagide and catalpol were isolated from the aerial parts of S. grandidentata.