Cytotoxic sesquiterpene lactones from Centaurothamnus maximus and Vicoa pentanema.

Abstract

The aerial parts of Centaurothamnus maximus yielded three cytotoxic guaianolides, chlorojanerin (1), cynaropicrin (2) and janerin (3). The structure elucidation of 1-3 was based on (1)H and (13)C NMR data, mainly 2D-NMR (1)H-(1)H COSY and (1)H-(13)C HETCOR experiments. Compounds 1-3 showed in vitro cytotoxic activity against human cancer cell lines of malignant melanoma (SK-MEL), epidermoid (KB), ductal (BT-549) and ovarian (SK-OV-3) carcinomas with IC(50) values of 2-6 microgram/mL. In addition, 12 sesquiterpene lactones (4-15), isolated previously from the aerial parts of Vicoa pentanema, were evaluated for cytotoxic and antimicrobial activities. 2alpha- Acetoxy-3beta-hydroxyalantolactone (10) and 8beta-hydroxyparthenolide (14) were found to be the main cytotoxic agents (IC(50) values of 2-6 microgram/mL against SK-MEL, BT-549 and SK-OV-3), while lactones 4, 5, 11 and 15 selectively inhibited the growth of human malignant melanoma (IC(50) value of 3.6-7.3 microgram/mL). Cell aggregation and cell adhesion assays, using HL-60 and HeLa cell lines, evaluated the effect of cytotoxic constituents 1-3, 10 and 14 on immune response and inflammation.

• Authors: Ilias Muhammad, Satoshi Takamatsu, Jaber S Mossa, Farouk S El-Feraly, Larry A Walker, Alice M Clark
• Journal: Phytotherapy research : PTR (Phytother Res) Vol. 17 Issue 2 Pg. 168-73 (Feb 2003) ISSN: 0951-418X [Print] England
• PMID: 12601682 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
• Copyright: Copyright 2003 John Wiley & Sons, Ltd.

Chemical References

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antineoplastic Agents
• Lactones
• Plant Extracts
• Sesquiterpenes

Topics

• Anti-Bacterial Agents
• Anti-Infective Agents (administration & dosage, pharmacology, therapeutic use)
• Antineoplastic Agents (administration & dosage, pharmacology, therapeutic use)
• Asteraceae
• Candida albicans (drug effects)
• Cell Adhesion (drug effects)
• Cell Aggregation (drug effects)
• Cryptococcus neoformans (drug effects)
• Dose-Response Relationship, Drug
• HL-60 Cells (drug effects)
• HeLa Cells (drug effects)
• Humans
• Inhibitory Concentration 50
• Lactones (administration & dosage, pharmacology, therapeutic use)
• Magnetic Resonance Spectroscopy
• Methicillin Resistance
• Microbial Sensitivity Tests
• Phytotherapy
• Plant Extracts (administration & dosage, pharmacology, therapeutic use)
• Plant Stems
• Sesquiterpenes (administration & dosage, pharmacology, therapeutic use)
• Staphylococcus aureus (drug effects)
• Tumor Cells, Cultured (drug effects)