A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest [1a]

Author:

Presley Christopher C.1,Rakotondraibe L. Harinantenaina12,Brodie Peggy J.1,Callmander Martin W.3,Randrianaivo Richard4,Rasamison Vincent E.5,Rakotobe Etienne5,Kingston David G. I.1

Affiliation:

1. Department of Chemistry, M/C 0212, Virginia Tech, Blacksburg, Virginia 24061-0212, USA

2. College of Pharmacy, Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University, Columbus, OH 43210, USA

3. Missouri Botanical Garden, P.O. Box 299, St. Louis, Missouri 63166-0299, USA

4. Missouri Botanical Garden, B.P 3391, Antananarivo 101, Madagascar

5. Centre National d'Application des Recherches Pharmaceutiques, B.P 702, Antananarivo 101, Madagascar

Abstract

Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene, which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line with an IC50 value of 8 μM.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

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