ABSTRACT
Seven undescribed sesquiterpene lactone dimers (SLDs) (carpeabrodilactones A-G), one known SLD, and six known sesquiterpenes were isolated from the fruit of Carpesium abrotanoides L. Carpeabrodilactone A was a dimeric carabrane featuring a rare C-13-C-13' linkage. Carpeabrodilactones B and C are the first two SLDs to be described possessing a carabranolide unit and a guaianolide unit connected by an O-ether linkage. The structures of the SLDs were assigned based on HRESIMS, NMR analysis, 13C NMR calculation, ECD calculation, and modified Mosher's method. Four SLDs showed potent cytotoxicity against K562 and/or A549 cells, with IC50 values below 10 µM, but none inhibited protein tyrosine phosphatases at 40 µM, including PTP1B, SHP1, CD45, and TCPTP.
Subject(s)
Asteraceae , Sesquiterpenes , Asteraceae/chemistry , Ethers , Fruit , Lactones/chemistry , Lactones/pharmacology , Molecular Structure , Phytochemicals , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Two new limonoids, named xylomexicanins C and D, were isolated from a dichloromethane extract of the seeds of Xylocarpus granatum cultivated in Hainan, China, and their structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Xylomexicanin C exhibited antiproliferative activity against human breast carcinoma cells (KT).
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Limonins/chemistry , Limonins/pharmacology , Meliaceae/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Humans , Limonins/isolation & purificationABSTRACT
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
Eight sesquiterpene lactones were isolated from the roots of Inula helenium and flowers of I. japonica. Among them, isoalantolactone (3) and santamarine (6) exhibited significant growth inhibitory activities against gynecologic cancer cell lines, while others weakly inhibited the growth of the cell lines (IC50 < or = 100 microM). In addition, 3 significantly inhibited the tumour growth of S180 tumour-bearing mice. Compounds 3 and 6 were not toxic to human embryonic lung fibroblast cells in vitro. These results demonstrated that the antitumour activities are closely related to the structures of the compounds, that is, an alpha-exomethylene-gamma-lactone ring is necessary for these activities.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Inula/chemistry , Lactones/pharmacology , Sesquiterpenes/chemistry , Cell Line, Tumor , HumansABSTRACT
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/pathologySubject(s)
Senecio/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Alkanes/chemistry , Alkanes/pharmacology , Coumarins/chemistry , Coumarins/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Flavonoids/chemistry , Flavonoids/pharmacology , Hydroxybenzoates/chemistry , Hydroxybenzoates/pharmacology , Monoterpenes/chemistry , Monoterpenes/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Steroids/chemistry , Steroids/pharmacology , Triterpenes/chemistry , Triterpenes/pharmacologyABSTRACT
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)
Melia/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Anthraquinones/chemistry , Anthraquinones/isolation & purification , Anthraquinones/pharmacology , Flavonoids/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Steroids/chemistry , Steroids/isolation & purification , Steroids/pharmacology , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacologySubject(s)
Leuzea/chemistry , Flavonoids/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Hydroxybenzoates/chemistry , Hydroxybenzoates/isolation & purification , Hydroxybenzoates/pharmacology , Lactones/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Phytosterols/chemistry , Phytosterols/isolation & purification , Phytosterols/pharmacology , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacology , Thiophenes/chemistry , Thiophenes/isolation & purification , Thiophenes/pharmacologySubject(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/chemistryABSTRACT
Ocean is a unique and excellent resource that provides a diverse array of intriguing natural products. Marine natural products have demonstrated significant and extremely potent biological activities and have captured the attention of natural products chemists in the past few decades. It is increasingly recognized that a wealth of fascinating natural products and novel chemical entities will play a dominant role in the discovery of useful leads for the development of pharmaceutical agents and provide useful probes to lead to breakthroughs in a variety of life-science fields. This article focused on the research progress of chemistry of marine natural products in recent five years.
Subject(s)
Aquatic Organisms/chemistry , Biological Products/isolation & purification , Marine Biology , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Animals , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Biological Products/chemistry , Biological Products/pharmacology , Humans , Macrolides/chemistry , Macrolides/isolation & purification , Macrolides/pharmacology , Marine Toxins/chemistry , Marine Toxins/isolation & purification , Marine Toxins/pharmacology , Molecular Structure , Peptides/chemistry , Peptides/isolation & purification , Peptides/pharmacology , Steroids/chemistry , Steroids/isolation & purification , Steroids/pharmacology , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacologySubject(s)
Jatropha/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Anticoagulants/chemistry , Anticoagulants/pharmacology , Antidiarrheals/chemistry , Antidiarrheals/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Heterocyclic Compounds, 2-Ring/chemistry , Heterocyclic Compounds, 2-Ring/pharmacology , Lignans/chemistry , Lignans/pharmacology , Peptides, Cyclic/chemistry , Peptides, Cyclic/pharmacology , Phytosterols/chemistry , Phytosterols/pharmacology , Terpenes/chemistry , Terpenes/pharmacologySubject(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/pharmacologySubject(s)
Meliaceae/chemistry , Alkaloids/chemical synthesis , Alkaloids/chemistry , Alkaloids/toxicity , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Anti-Infective Agents/toxicity , Antidiarrheals/chemical synthesis , Antidiarrheals/chemistry , Antidiarrheals/toxicity , Antimalarials/chemical synthesis , Antimalarials/chemistry , Antimalarials/toxicity , Flavonoids/chemical synthesis , Flavonoids/chemistry , Flavonoids/toxicity , Neuroprotective Agents/chemical synthesis , Neuroprotective Agents/chemistry , Neuroprotective Agents/toxicity , Terpenes/chemical synthesis , Terpenes/chemistry , Terpenes/toxicitySubject(s)
Illicium/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-HIV Agents/chemistry , Anti-HIV Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Hydrocarbons, Aromatic/chemistry , Hydrocarbons, Aromatic/pharmacology , Pesticides/chemistry , Pesticides/pharmacology , Quinones/chemistry , Quinones/pharmacology , Terpenes/chemistry , Terpenes/pharmacologyABSTRACT
Taxusecone, 2alpha,7beta,9alpha,10beta-tetraacetoxy-5alpha,12-dihydroxy-11,12-secotax-4(20)-ene-11,13-dione (1), a novel taxane with an unprecedented skeleton, was isolated from the needles of Taxus cuspidata.
Subject(s)
Taxoids/chemistry , Taxoids/isolation & purification , Taxus/chemistry , Taxus/anatomy & histology , Taxus/metabolismABSTRACT
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.