Effect of 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid and its lactone derivatives on the growth of human cancer cells.

Abstract

The furanditerpene 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid (1) is a natural product biosynthesized by some species from the genus Pterodon (Leguminosae). This secondary metabolite has multiple biological activities that include anti-inflammatory, analgesic, plant growth regulatory, anti-edematogenic, photosystem II inhibitory and photosynthesis uncoupler, and antifungal properties. However, few studies on the antiproliferative profile of compound 1 and/or its derivatives have been reported up to date. Here, we describe the isolation of compound 1 from hexane extract of P. polygalaeflorus fruits as well as the semisynthesis of three lactone derivatives: 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2), 6 alpha-acetoxyvouacapan-7 beta,17 beta-lactone (3), and 6-oxovouacapan-7 beta,17 beta-lactone (4). Additionally, antiproliferative activity of these compounds against nine human cancer cell lines was investigated. Our results revealed that 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2) was the most potent furanditerpene against all cancer cell lines studied. The presence of non-substituted hydroxyl group at C-6 and the presence of 7 beta,17 beta-lactone ring are important for the antiproliferative activity of these compounds.

• Authors: Felipe P G Euzébio, Flávio J L dos Santos, Dorila Piló-Veloso, Ana Lúcia T G Ruiz, João Ernesto de Carvalho, Dalton L Ferreira-Alves, Angelo de Fátima
• Journal: Bioorganic chemistry (Bioorg Chem) Vol. 37 Issue 3 Pg. 96-100 (Jun 2009) ISSN: 1090-2120 [Electronic] United States
• PMID: 19394666 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone
• Antineoplastic Agents, Phytogenic
• Diterpenes
• Lactones
• vouacapan

Topics

• Animals
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Diterpenes (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Fabaceae (chemistry)
• Humans
• Lactones (chemistry, isolation & purification, pharmacology)