Antiproliferative-assay directed isolation of scalarane sesterterpenes from an unidentified sponge from Madagascar

L Harinantenaina; PJ Brodie; J Maharavo; G Bakary; DGI Kingston

doi:10.1055/s-0032-1320704

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Planta Med 2012; 78 - PI17
DOI: 10.1055/s-0032-1320704

Antiproliferative-assay directed isolation of scalarane sesterterpenes from an unidentified sponge from Madagascar

L Harinantenaina ¹, PJ Brodie ¹, J Maharavo ², G Bakary ², DGI Kingston ¹

¹Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA
²Centre National de Recherches Océanographiques, Nosy-Bé, Madagascar

Congress Abstract

The Madagascar International Cooperative Biodiversity Group (ICBG) program aims to integrate the improvement of human health through anticancer drug discovery from natural products with biodiversity conservation and economic development in Madagascar. An extract of a marine organism with moderate activity against the A2780 ovarian cancer cell line (IC₅₀ 3.4µg/mL) was selected for study. Bioassay-directed fractionation afforded four new type-II scalarane sesterterpenes: 12α-hydroxy-22-hydroxy-24-methyl-24-oxoscalar-16-en-25α-al (1), 12β-hydroxy-22-hydroxy-24-methyl-24-oxoscalar-16-en-25β-al (2), 22-hydroxy-12β,24-dihydroxy-24-methylscalaran-25,24-olactone (3), and 22-hydroxy-24-oxo-24-homoscalara-16,25(26)-dien-12β-ol (4). The structures of all compounds were determined by physical, chemical and spectroscopic evidence including 1D and 2D-NMR. Compounds 1 and 2 displayed strong antiproliferative activity against the A2780 human ovarian cancer cell line (IC₅₀ values of 0.28µM and 0.26µM, respectively) while compounds 3 and 4 exhibited modest activity (IC₅₀ values of 9µM and 4.5µM, respectively).