Biocatalysis of the Anticancer Sipholane Triterpenoids

Abstract

The Red Sea sponge Callyspongia (= Siphonochalina) siphonella is a rich source of sipholane triterpenoids. Biocatalysis of the major sipholanes, sipholenol A (1) and sipholenone A (2), respectively, by Mucor ramannianus ATCC 9628 and Cunninghamella elegans ATCC 7929 afforded four new metabolites 3 - 6 along with sipholenol G and 28-hydroxysipholenol A. Major sipholanes along with their biocatalytic products were investigated for their antiproliferative activity against the highly malignant +SA mouse mammary epithelial cell line. Sipholenone A (2) was the most active sipholane inhibiting +SA cell proliferation with an IC₅₀ value of 20 - 30 μM. Sipholenone A, also, showed cytotoxicity against MCF-7 at a dose of 0.9 μM and antiangiogenic activity in the CAM (chorio-allantoic membrane) assay. This is the first report on anticancer activity of these triterpenoids.

Key words

Red Sea - Callyspongia siphonella - Callyspongiidae - sipholanes - biocatalysis - Mucor ramannianus - Cunninghamella elegans - antiproliferative - +SA mouse mammary epithelial cells - MCF-7 cells - breast cancer - antiangiogengic - CAM

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