Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta, 10alpha-epoxy-salonitenolide

6533b872fe1ef96bd12d34fb

RESEARCH PRODUCT

Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta, 10alpha-epoxy-salonitenolide

Rosselli Sergio Maggio Antonella Maria Raccuglia Rosa Angela Morris-natschke Susan L Bastow Kenneth F Lee Kuo-hsiung Bruno Maurizio

subject

Magnetic Resonance Spectroscopy Molecular Structure Plant Extracts Centaurea Settore CHIM/06 - Chimica Organica germacranolides epoxygermacranolides cyclization eudesmanolides absolute configuration cytotoxicity Antineoplastic Agents Phytogenic Sesquiterpenes Germacrane Cell Line Tumor Humans Drug Screening Assays Antitumor Sesquiterpenes Sicily Cell Proliferation

description

The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1beta,10alpha-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2-6 were selectively cytotoxic against the MCF-7 breast cancer cell line.

year	journal	country	edition	language
2010-06-05

http://hdl.handle.net/10447/54918

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