ABSTRACT
Two new acorane-type sesquiterpenoids, harzianes A and B (1 and 2), together with two known cyclonerodiol-type sesquiterpenoids (3-4) and four known sterols (5-8) were isolated from the endophytic Trichoderma harzianum, associated with the medicinal plant Paeonia lactiflora Pall. Compounds 1 and 2 were identified as a pair of heterotropic isomers by spectroscopic analysis (HR-ESI-MS, 1D and 2D NMR), and their absolute configurations were determined by ECD calculations. All compounds were tested for anti-inflammatory activity, however, none demonstrated such activity.
ABSTRACT
Eupatorium (family: Compositae), which comprises nearly 1200 species, is distributed throughout tropical America, Europe, Africa, and Asia. Up to now, the reported constituents from the genus Eupatorium involve flavonoids, terpenoids, pyrrolizidine alkaloids, phenylpropanoids, quinonoids, essential oils, and some others, altogether more than 300 compounds. Studies have shown that Eupatorium and its active principles possess a wide range of pharmacological activities, such as cytotoxic, antifungal, insecticidal, antibacterial, anti-inflammatory, and antinociceptive activities. Currently, effective monomeric compounds or active parts have been screened for pharmacological activities from Eupatorium in vivo and in vitro. Increasing amount of data supports application and exploitation for new drug development.
Subject(s)
Analgesics/pharmacology , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Eupatorium/chemistry , Organic Chemicals/pharmacology , Plant Extracts/pharmacology , Analgesics/chemistry , Analgesics/isolation & purification , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Humans , Organic Chemicals/chemistry , Organic Chemicals/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purificationABSTRACT
A rapid and sensitive high-performance liquid chromatographic (HPLC) method was developed for the simultaneous separation and determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium. The HPLC separation was performed on an Elite Hypersil C18 column (200 × 4.6 mm i.d., 5 µm particle size) with a gradient elution of solvent A (acetonitrile) and solvent B (0.1% phosphoric acid in water) at a flow rate of 1.0 mL/min. Detection was monitored at 225 nm. The recovery of chlorogenic acid ranged from 95.6 to 107.7%, the recovery of caffeic acid ranged from 95.4 to 104.2%, the recovery of alantolactone ranged from 95.8 to 100.8% and the recovery of isoalantolactone ranged from 96.5 to 102.3%. The retention times for chlorogenic acid, caffeic acid, alantolactone and isoalantolactone were 5.2, 7.1, 25.6 and 26.6 min with the limits of detection of 0.069, 0.021, 0.039 and 0.051 µg/mL, respectively. Relative standard deviation for the intra-day and inter-day was ≤2.5%. The validated method is reliable for the routine control of these four compounds in I. helenium.
Subject(s)
Caffeic Acids/analysis , Chlorogenic Acid/analysis , Chromatography, High Pressure Liquid/methods , Inula/chemistry , Lactones/analysis , Plant Extracts/chemistry , Sesquiterpenes, Eudesmane/analysis , Limit of Detection , Linear Models , Reproducibility of ResultsABSTRACT
OBJECTIVE: To study the chemical constituents in the needles of Taxus cuspidata collected from Japan. METHODS: Chemical constituents were isolated by column chromatography, TLC and preparative HPLC. The structures were identified on the basis of NMR spectral analysis. RESULTS: Six non-taxoids were isolated and identified as: 4-[(1E)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-2-cyclohexen-1-one (1), megastigm-5-ene-3, 9-diol (2), 6alpha-epoxy-7-megastigmen-9-one (3), 4-(4-hydroxyphenyl)-2-butanone (4), 12-hydroxy-alpha-cyperone (5), scutellarein-7-O-alpha-L-rhamnoside (6). CONCLUSION: Compounds 2 - 6 are isolated from Taxus genus for the first time. Compound 1 is obtained from Taxus cuspidata for the first time.
Subject(s)
Taxus/chemistry , Chromatography, High Pressure Liquid , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , TaxoidsABSTRACT
A phytochemical investigation of Chromolaena odorata resulted in the isolation of five new compounds, 5aα,6,9,9aß,10-pentahydro-10ß-hydroxy-7-methylanthra[1,2-d][1,3]dioxol-5-one (1), 1,2-methylenedioxy-6-methylanthraquinone (2), 3-hydroxy-1,2,4-trimethoxy-6-methylanthraquinone (3), 3-hydroxy-1,2-dimethoxy-6-methylanthraquinone (4), and 7-methoxy-7-epi-medioresinol (5), together with 12 known compounds, odoratin (6), 3ß-acetyloleanolic acid (7), ursolic acid (8), ombuin (9), 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (10), (-)-pinoresinol (11), austrocortinin (12), tianshic acid (13), cleomiscosin D (14), (-)-medioresinol (15), (-)-syringaresinol (16), and cleomiscosin A (17). All the compounds were evaluated for their PPARγ transactivation activity, and compound 6 showed moderate activity with an EC(50) value of 3.10 µM.
Subject(s)
Anthraquinones/isolation & purification , Chromolaena/chemistry , Dioxoles/isolation & purification , Dioxoles/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Flavonoids/isolation & purification , Flavonoids/pharmacology , Lignans/isolation & purification , Lignans/pharmacology , PPAR gamma/agonists , Anthraquinones/chemistry , Anthraquinones/pharmacology , Dioxoles/chemistry , Drugs, Chinese Herbal/chemistry , Flavonoids/chemistry , Furans/chemistry , Furans/isolation & purification , Hepatocytes/drug effects , Humans , Lignans/chemistry , Luciferases/metabolism , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , StereoisomerismABSTRACT
A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3â20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7ß,9α,10ß-triacetoxytaxa-4(20),12-diene-2α,5α,11ß-triol (1) and 2α,7ß,10ß-triacetoxy-5α-hydroxy-2(3â20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.
Subject(s)
Antineoplastic Agents/analysis , Plant Extracts/analysis , Taxoids/analysis , Taxus/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Cell Line, Tumor , Female , Humans , Magnetic Resonance Spectroscopy , Male , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry , Prostatic Neoplasms/drug therapy , Prostatic Neoplasms/pathology , Taxoids/chemistry , Taxoids/isolation & purification , Taxoids/pharmacology , Treatment Failure , Uterine Cervical Neoplasms/drug therapy , Uterine Cervical Neoplasms/pathologyABSTRACT
Achillinin A (2ß,3ß-epoxy-1α,4ß,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC(50)) values of 5.8, 10 and 0.31 µM, respectively.
Subject(s)
Achillea/chemistry , Adenocarcinoma/drug therapy , Antineoplastic Agents, Phytogenic/pharmacology , Carcinoma, Non-Small-Cell Lung/drug therapy , Lung Neoplasms/drug therapy , Phytotherapy , Plant Extracts/pharmacology , Sesquiterpenes/pharmacology , Small Cell Lung Carcinoma/drug therapy , Adenocarcinoma/pathology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/therapeutic use , Carcinoma, Non-Small-Cell Lung/pathology , Cell Line, Tumor , Cell Survival/drug effects , Flowers/chemistry , Humans , Inhibitory Concentration 50 , Lung Neoplasms/pathology , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Plant Extracts/therapeutic use , Sesquiterpenes/chemistry , Sesquiterpenes/therapeutic use , Small Cell Lung Carcinoma/pathologyABSTRACT
Three new taxanes, 2 α,9 α,10 ß-triacetoxy-13 α-( ß-D-glucopyranosyloxy)taxa-4(20),11-dien-5 α-ol, 5 α,10 ß,13 α-triacetoxytax-11-ene-2 α,7 ß,9 α,20-tetraol, and 5 α,10 ß,13 ß-triacetoxy-2 α,7 ß-dihydroxy-2(3â20) abeotaxa-4(20),11-dien-9-one, were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.
Subject(s)
Glucosides/isolation & purification , Plant Extracts , Taxoids/isolation & purification , Taxus/chemistry , Glucosides/chemistry , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves , Taxoids/chemistrySubject(s)
Asteraceae/chemistry , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Coumarins/chemistry , Plant Extracts/chemistry , Pyrrolizidine Alkaloids/chemistry , Terpenes/chemistrySubject(s)
Biological Products/chemistry , Diterpenes/chemistry , Plants, Medicinal/chemistry , Biological Products/pharmacology , Bridged Bicyclo Compounds/chemistry , Bridged Bicyclo Compounds/isolation & purification , Bridged Bicyclo Compounds/pharmacology , Diterpenes/isolation & purification , Diterpenes/pharmacology , Molecular Structure , Taxoids/chemistry , Taxoids/isolation & purification , Taxoids/pharmacologyABSTRACT
Two new mexicanolide-type limonoids, named xylomexicanin A (1) and xylomexicanin B (2), were isolated from seeds of the Chinese mangrove Xylocarpus granatum. Their structures were elucidated on the basis of spectroscopic methods. Compound 1 exhibited antiproliferative activity against human breast carcinoma cells (KT), while 2 did not show inhibitory effects on eleven human tumour cell lines tested.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Limonins/chemistry , Limonins/pharmacology , Meliaceae/chemistry , Neoplasms/drug therapy , Seeds/chemistry , Antineoplastic Agents/isolation & purification , Asia, Southeastern , Cell Line, Tumor/drug effects , Female , Humans , Limonins/isolation & purification , Magnetic Resonance Spectroscopy , Medicine, TraditionalABSTRACT
The plants of genus Celastrus, distributed in Asia, have been used as natural insecticides and folk medicines to treat fever, chill, joint pain, edema, rheumatoid arthritis, and bacterial infection in China for a long time. This contribution reviews the chemical constituents, isolated from the plants in genus Celastrus in the past few decades, and their biological activities. The compounds listed are sesquiterpenes (beta-agarofurans), diterpenes, triterpenes, alkaloids, and flavonoids.
Subject(s)
Celastrus/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Diterpenes/chemistry , Diterpenes/isolation & purification , Diterpenes/pharmacology , Flavonoids/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Medicine, Chinese Traditional , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Triterpenes/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacologyABSTRACT
OBJECTIVE: To study the non-taxoids in the leaves of Taxus mairei. METHOD: The chemical constituents were isolated by chromatography and identified by spectral data. RESULT: Five compounds, taxamairin A (1), taxamairin B (2), sciadopitysin (3), ( - ) matairesinol (4), ponasterone A (5) were isolated and identified. CONCLUSION: Compounds 3-5 were isolated from this plant for the first time, compounds 1 and 2 were isolated from the leaves of T. mairei for the first time.