ABSTRACT
A new isoflavone (Z)-5,7,4'-trihydroxy-3'-[3-hydroxy-3-methyl-1-butenyl] isoflavone (1) together with seven known isoflavones (2-8) were isolated from the fruits of the Ficus auriculata. Their structures were established on the basis of 1 D, 2 D-NMR spectroscopic data and HR-ESI-MS analysis. All compounds were evaluated for their antibacterial activities against five pathogenic bacteria in vitro. Compounds 3 and 4 exhibited significant antibacterial activities against five pathogenic bacteria with the MIC values ranging from 1.25 to 20 µg/mL.[Formula: see text].
Subject(s)
Ficus , Isoflavones , Anti-Bacterial Agents/chemistry , Ficus/chemistry , Fruit/chemistry , Isoflavones/chemistry , Molecular Structure , Plant Extracts/chemistryABSTRACT
The phytochemical investigation of the stems of Homalium stenophyllum afforded seven new phenolic glycosides (1-5 and 8-9) and two known compounds (6 and 7). Their structures were elucidated by comprehensive analyses of NMR spectroscopic, mass spectrometric data and chemical hydrolysis. Additionally, their anti-inflammatory activities against the NO production in LPS-induced macrophages were evaluated.
Subject(s)
Glycosides , Phenols , Salicaceae/chemistry , Anti-Inflammatory Agents/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Macrophages/drug effects , Molecular Structure , Phenols/isolation & purification , Phenols/pharmacology , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Stems/chemistryABSTRACT
Three new methylated Δ8-pregnene steroids, stemphylisteroids A-C (1-3) were isolated from the medicinal plant Polyalthia laui-derived fungus Stemphylium sp. AZGP4-2. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. The absolute configuration of 1 was determined by X-ray crystallographic analysis. Compound 1 show antibacterial activity against Escherichia coli with the MIC value of 6.25⯵g/mL, and 2 exhibited a broad spectrum of antibacterial activities against six pathogenic bacteria with the MIC values ranging from 12.5 to 50⯵g/mL. The discovery of three methylated Δ8-pregnene steroids 1-3 are a further addition to diverse and complex array of methylated steroids.
Subject(s)
Anti-Bacterial Agents/pharmacology , Ascomycota/chemistry , Escherichia coli/drug effects , Polyalthia/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Crystallography, X-Ray , Dose-Response Relationship, Drug , Methylation , Microbial Sensitivity Tests , Models, Molecular , Molecular Conformation , Structure-Activity RelationshipABSTRACT
One new lignan derivative 2,3-dimethyl-4-(4'-hydroxy-3',5'-dimethoxyphenyl)-6-hydroxy-7-methoxy-naphthalene (1), together with four known analogues (2-5), were isolated from acetone extract of the fruiting bodies of Ganoderma lipsiense collected in the Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compound 1 showed insecticidal activity against newly hatched karvae of Helicoverpa armigera Hubner. Compounds 1-5 showed moderate antibacterial activity against Staphylococcus aureus with the same MIC value of 1.25 µg/mL.
Subject(s)
Anti-Bacterial Agents/pharmacology , Ganoderma/chemistry , Insecticides/pharmacology , Lignans/pharmacology , Animals , Anti-Bacterial Agents/chemistry , China , Drug Evaluation, Preclinical , Fruiting Bodies, Fungal/chemistry , Insecticides/chemistry , Lignans/chemistry , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Moths/drug effects , Spectrometry, Mass, Electrospray Ionization , Staphylococcus aureus/drug effectsABSTRACT
One new norisoprenoid 3,9-dihydroxy dihydro actinidiolide (1), together with eleven known compounds (2-12), were isolated from ethanol extract of the leaves of Ficus pumila collected in Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1, 2, 4, 5, 8 and 10-12 were isolated from the F. pumila for the first time. All compounds were evaluated for their cytotoxic activity. Compounds 3 and 9 showed weak cytotoxic activity against Hela, MCF-7 and A549 cell lines.
Subject(s)
Ficus/chemistry , Norisoprenoids/isolation & purification , Cell Line, Tumor , Humans , Norisoprenoids/chemistry , Plant Extracts/analysis , Plant Leaves/chemistryABSTRACT
One new furofuran lignan 2-methoxy-9ß-hydroxydiasesamin (1), and four analogues (2-5), together with eight alkaloids (6-13), were isolated from the ethanol extract of the aerial part of Clinacanthus nutans. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All the compounds were isolated from the genus of Clinacanthus for the first time. In addition, lignans isolated from C. nutans was reported for the first time. Compound 1 exhibited modest activity against three human tumor cell lines Hela, MCF-7, and A549, with IC50 values of 68.55, 60.00, and 59.17 µM, respectively.
Subject(s)
Acanthaceae/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Lignans/chemistry , Lignans/pharmacology , A549 Cells , Alkaloids/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Lignans/isolation & purification , MCF-7 Cells , Magnetic Resonance Spectroscopy , Molecular Structure , Plants, Medicinal/chemistryABSTRACT
Two eudesmane sesquiterpene lactones, wedetrilides B (1) and C (2), along with five known analogues (3 - 8), an ent-kaurane diterpenoid (9), a steroid (10), as well as cinnamic acid derivatives (11 - 13), were isolated from the flowers of Wedelia trilobata. Their structures were elucidated on the basis of extensive spectroscopic analyses and by comparison of their NMR data with those of related compounds. Furthermore, the structures of 1 and 3 - 5 were confirmed by X-ray single-crystal diffraction analyses. Compounds 4 and 5 exhibited weak cytotoxic activities against the MCF-7, HeLa, and A549 cell lines. Compounds 3 - 5 were also evaluated for their inhibitory effects against HIV lytic replication.
Subject(s)
Anti-HIV Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Flowers/chemistry , HIV/drug effects , Sesquiterpenes/pharmacology , Wedelia/chemistry , Anti-HIV Agents/chemistry , Anti-HIV Agents/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Microbial Sensitivity Tests , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Structure-Activity Relationship , Virus Replication/drug effectsABSTRACT
The chemical consituents from Artabotrys hongkongensis were separated and purified by column chromatographies with silica gel, Sephadex LH-20, ODS and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in the literature. As a result, 16 sesquiterpenes were isolated and elucidated as blumenol A (1), 4, 5-dihydroblumenol A (2), (6R, 9S)-3-oxo-a-ionol (3), 3-hydroxy-ß-ionone (4), dehydrovomifoliol (5), (3R, 6R, 7E) -3-hydroxy-4, 7-megastigmadien-9-one (6), sarmentol F (7), 10-oxo-isodauc-3-en-15-oic acid (8), fukinone (9), petasitolone (10), ß-eudesmol (11), trans-3ß-(1-hydroxy-1-methylethyl)- 8aß-methyl-5-methylenedecalin-2-one (12), 10-hydroxyaristolan-9-one (13), aristol-8-en-1-one (14), aristolan-9-en-1-one (15), and aristolan-1, 9-diene (16). This is the first study on the chemical consituents of A. hongkongensis, and all compounds were isolated from the genus Artabotrys for the first time.
Subject(s)
Annonaceae/chemistry , Sesquiterpenes/isolation & purification , Chromatography, High Pressure Liquid , Molecular Structure , Phytochemicals/isolation & purificationABSTRACT
Three new phenylpropanoid derivatives, dasymaroacid A (1), dasymaroesters B and C (2 and 3), and one new polyoxygenated 6H-dibenzo[b,d]pyran-6-one derivative dasymarolactone D (4), together with seven known compounds (5-11), were isolated from the stems of Dasymaschalon rostratum Merr. Compounds 1 and 2 are unusual phenylpropanoid derivatives with a polymethyl substituted cyclopentene conjugated diketone as a substituent, and 3 is a unique cinnamic acid detective with a polymethyl substituted cyclohexene conjugated triketone as a substituent. Their structures were elucidated by extensive spectroscopic methods and chemical method, and 4 was further confirmed by the single crystal X-ray diffraction method. Compounds 1-4 and 7 showed weak anti-HIV-1 activities with EC50 values ranged from 16.44 to 25.91µM.
Subject(s)
Annonaceae/chemistry , HIV-1/drug effects , Lactones/chemistry , Phenanthrenes/chemistry , Anti-HIV Agents/chemistry , Anti-HIV Agents/isolation & purification , Molecular Structure , Plant Stems/chemistryABSTRACT
Three guaiane-type sesquiterpenoids, dysodensiols G-I (1-3), together with five known sesquiterpenoids (4-8) were isolated from the stems of Fissistigma oldhamii (Hemsl.) Merr. Compound 1 represents the first example of an ene(6 â 5)-abeo-14-norguaiane sesquiterpenoid derived from natural products. Their structures were elucidated by a combination of 1D and 2D NMR and MS spectra. The absolute configuration of 2 was determined by an X-ray crystallographic analysis. The inhibitory effect of all compounds on the proliferation of primary synovial cells was evaluated. Compound 3 showed a potent inhibitory effect on the proliferation of synoviocytes with an IC50 value of 1.0 µM.
Subject(s)
Annonaceae/chemistry , Drugs, Chinese Herbal/chemistry , Sesquiterpenes, Guaiane/chemistry , Sesquiterpenes, Guaiane/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Synoviocytes/drug effects , Animals , Cell Proliferation/drug effects , Crystallography, X-Ray/methods , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy/methods , Mass Spectrometry/methods , Molecular Structure , Norisoprenoids/pharmacology , Plant Stems/chemistry , Rats , Rats, Sprague-Dawley , Sesquiterpenes/isolation & purification , Sesquiterpenes, Guaiane/isolation & purification , Synoviocytes/cytologyABSTRACT
One new lignan derivative 2,3-dimethyl-4-(4-methoxyphenyl)-6,7-dihydroxynaphthalene (1), together with five known compounds (2-6), were isolated from ethanol extract of the branches and leaves of Combretum alfredii Hance collected in Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1, 2, 5 and 6 were isolated from the genus of Combretum for the first time. All compounds were evaluated for their antibacterial activities. Compounds 1 and 2 showed significant antibacterial activities against six pathogenic bacteria.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Combretum/chemistry , Lignans/isolation & purification , Lignans/chemistry , Lignans/pharmacology , Naphthols , Plant Extracts/analysis , Plant Leaves/chemistryABSTRACT
A new enantiomeric pair of spirodiketones, (+)- and (-)-denobilone A (1 and 2), three new phenanthrene derivatives (3-5), and three new biphenanthrenes (22-24), along with 11 known phenanthrene derivatives (6-16), five known bibenzyl derivatives (17-21), and four known biphenanthrenes (25-28), were isolated from Dendrobium nobile. The structures of 1-5 and 22-24 were elucidated using comprehensive spectroscopic methods. (+)-Denobilone and (-)-denobilone A (1 and 2) were isolated as a pair of enantiomers by chiral HPLC. The absolute configurations of (+)- and (-)-denobilone A (1 and 2) were determined by comparing their experimental and calculated electronic circular dichroism spectra. The absolute configuration of denobilone B (3) was determined by X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Bibenzyls/isolation & purification , Bibenzyls/pharmacology , Dendrobium/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Phenanthrenes/isolation & purification , Phenanthrenes/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Bibenzyls/chemistry , Circular Dichroism , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Fungi/drug effects , Molecular Conformation , Molecular Structure , Phenanthrenes/chemistry , Plant Stems/chemistryABSTRACT
One new alkaloid consanguine B (1), together with 10 known alkaloids (2-11), were isolated from ethanol extract of the branches and leaves of Polyalthia obliqua Hook.f. & Thomson collected in the Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their cytotoxic activities. Compound 1 showed weak cytotoxic activities against Hela and MCF-7 human cancer cell lines.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Polyalthia/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Berberine/chemistry , Berberine Alkaloids/isolation & purification , Berberine Alkaloids/pharmacology , China , Drug Screening Assays, Antitumor , HeLa Cells/drug effects , Humans , MCF-7 Cells/drug effects , Molecular Structure , Plant Extracts/chemistry , Plant Leaves/chemistryABSTRACT
Five new clerodane diterpenoids, polylauiester A (1), (4â2)-abeo-2,13-diformyl-cleroda-2,12E-dien-14-oic acid (2) and polylauiamides B-D (3-5), together with 11 known clerodane diterpenoids (6-16), were isolated from the roots of Polyalthia laui. Among them, polylauiester A (1) represents the first example of a novel norclerodane diterpenoid only containing 17 carbon atoms on the carbon skeleton, and polylauiamide B (3) is an unusual diterpenoid with a p-substituted benzene ring as a substituent. Their structures were elucidated by extensive spectroscopic methods, and the relative configuration of polylauiamide B (3) was further confirmed by the single crystal X-ray diffraction method. Biological evaluation of new compounds against human Hela, MCF-7 and A549 human cancer cell lines showed that all compounds displayed weak cytotoxicities against various human cancer cell lines in the range of IC50 at 25.01-39.31µM.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Diterpenes, Clerodane/chemistry , Polyalthia/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Crystallography, X-Ray , Diterpenes, Clerodane/isolation & purification , Humans , Molecular Structure , Plant Extracts/chemistry , Plant Roots/chemistryABSTRACT
14 alkaloids were obtained from stems and leaves of Fissistigma oldhamii, by silica gel, ODS, Sephadex LH-20 column chromatographies, and semi-preparative HPLC. Using physicochemical and spectral methods, the isolated alkaloids were identified as norcepharadione B(1), asimilobine(2), lanuginosine(3), laurotanine(4), isocorydine(5), anolobine(6), xylopine(7), N-methylbuxifoline(8), aristolactam AIIIa(9), piperumbellactam A(10), goniopedaline(11), aristololactam BIII(12), liriodenine(13), and salutaridine(14), respectively. Compounds 3-5, 8, 10, 11 and 14 were isolated from the genus Fissistigma for the first time.
Subject(s)
Alkaloids/chemistry , Annonaceae/chemistry , Chromatography, High Pressure Liquid , Phytochemicals/chemistry , Plant Leaves/chemistry , Plant Stems/chemistryABSTRACT
Reinvestigating the chemical constituents of the roots of Xanthium sibiricum led to the isolation of a new naphthoquinone (1), together with 13 known compounds (2-14). Their structures were elucidated by using spectroscopic analyses, including HR-ESI-MS, 1D and 2D NMR, and by comparing their NMR data with those of related compounds. Compound 1 showed moderate antibacterial activity against Escherichia coli, Bacillus subtilis, Micrococcus tetragenus and Staphylococcus aureus, while 6 and 12 showed stronger antibacterial activity than the positive control ciprofloxacin against E. coli, with minimum inhibitory concentration values of 0.17 and 0.35 µg/mL, respectively.
Subject(s)
Anti-Bacterial Agents/chemistry , Naphthoquinones/chemistry , Plant Roots/chemistry , Xanthium/chemistry , Anti-Bacterial Agents/isolation & purification , Microbial Sensitivity Tests , Molecular Structure , Naphthoquinones/isolation & purification , Plant Extracts/chemistryABSTRACT
Two new phenylpropanoid glycosides, named ß-D-(1-O-acetyl-3,6-O-diferuloyl) fructofuranosyl ß-D-6'-O-acetylglucopyranoside (1) and ß-D-(1-O-acetyl-3,6-O-diferuloyl) fructofuranosyl α-D-glucopyranoside (2), along with two known analogues (3-4) and four glycerides (5-8), were isolated from the EtOAc extract of the leaves of Ananas comosus. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses, as well as HR-ESI-MS experiments. Compounds 1-4 showed significant antibacterial activities against Staphylococcus aureus and Escherichia coli.
Subject(s)
Ananas/chemistry , Glycosides/chemistry , Plant Leaves/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Molecular StructureABSTRACT
Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of beta-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 microg/mL, respectively.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Gallic Acid/analogs & derivatives , Polyalthia/chemistry , Allantoin/isolation & purification , Drug Screening Assays, Antitumor , Gallic Acid/chemistry , Gallic Acid/isolation & purification , Humans , K562 Cells , Lignans/isolation & purification , Plant Stems/chemistry , Sitosterols/isolation & purification , Stigmasterol/isolation & purificationABSTRACT
Five new degraded diterpenoids trigoxyphins J-N (1-5), among them trigoxyphins K and L have a novel carbon skeleton, together with four known analogues (6-9) have been obtained from the ethanol extract of the twigs of Trigonostemon xyphophylloides. Compounds 1-5 were evaluated for their cytotoxic activity in vitro against three human tumor cell lines by MTT assay. The results exhibited that Trigoxyphin N (5) showed moderate cytotoxicities against SPC-A-1 and SGC-7901 cancer cell lines.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Diterpenes/chemistry , Euphorbiaceae/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/toxicity , Cell Line, Tumor , Cell Survival/drug effects , Diterpenes/isolation & purification , Diterpenes/toxicity , Euphorbiaceae/metabolism , Humans , Magnetic Resonance Spectroscopy , Molecular Conformation , Plant Extracts/chemistry , Structure-Activity RelationshipABSTRACT
Aggregation and accumulation of beta-amyloid peptide (Abeta) in brain tissues contribute to the pathogenesis of Alzheimer's disease. Therefore, the promotion of Abeta clearance is one of the key targets for preventing and treatment Alzheimer's disease. Studies proved that some traditional Chinese medicine (TCM) compounds and extracts could impact the activity of degrading enzyme in amyloid peptide, the transport of hemato encephalic barrier and the phagocytosis of microglial cells, promote Abeta clearance, and improve learning and memory of animal models with Alzheimer's disease. In this review, we made an summary for the relations between Abeta and Alzheimer's disease, the Abeta clearance mechanism and the clearance effect of traditional Chinese medicines.