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

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, an...

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Bibliographic Details
Published in:Bioorganic chemistry 2009-06, Vol.37 (3), p.96-100
Main Authors: Euzebio, Felipe PG, Dos Santos, Flavio JL, Pilo-Veloso, Dorila, Ruiz, Ana Lucia TG, De Carvalho, Joao Ernesto, Ferreira-Alves, Dalton L, De Fatima, Angelo
Format: Article
Language:English
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Summary: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..
ISSN:0045-2068
DOI:10.1016/j.bioorg.2009.03.004