Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana

A F Barrero; J E Oltra; V Morales; M Alvarez; I Rodríguez-García

doi:10.1021/np970040p

Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana

J Nat Prod. 1997 Oct;60(10):1034-5. doi: 10.1021/np970040p.

Authors

A F Barrero¹, J E Oltra, V Morales, M Alvarez, I Rodríguez-García

Affiliation

¹ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Spain. afbarre@goliat.ugr.es

PMID: 9358646
DOI: 10.1021/np970040p

Abstract

Malacitanolide (2), a new eudesmanolide isolated from the aerial parts of Centaurea malacitana, was characterized spectroscopically. The synthesis of 2 from cnicin (1), via the epoxide 3, confirmed the structure and stereochemistry of malacitanolide, as well as its biogenetic relationship with 1. Cytotoxic activity values for 2 are significantly higher than for 1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Cyclization
Drug Screening Assays, Antitumor
Humans
Leukemia P388 / drug therapy
Mice
Plant Leaves / chemistry*
Sesquiterpenes / isolation & purification*
Sesquiterpenes / metabolism*
Sesquiterpenes / pharmacology
Tumor Cells, Cultured

Substances

Antineoplastic Agents, Phytogenic
Sesquiterpenes
malacitanolide
cnicin