Novel Cytotoxic Polyoxygenated Steroids from an Okinawan Sponge <i>Dysidea</i> sp.

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  • GOVINDAM Sudhakar V. S.
    Graduate School of Bioagricultural Sciences, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya University
  • CHOI Bong-Keun
    Graduate School of Bioagricultural Sciences, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya University
  • YOSHIOKA Yukio
    Graduate School of Biomedical Sciences, Hiroshima University Graduate School of Biomedical Sciences, Hiroshima University
  • KANAMOTO Akihiko
    OP Bio Factory Co., Ltd. OP Bio Factory Co., Ltd.
  • FUJIWARA Takeshi
    OP Bio Factory Co., Ltd. OP Bio Factory Co., Ltd.
  • OKAMOTO Tetsuji
    Graduate School of Biomedical Sciences, Hiroshima University Graduate School of Biomedical Sciences, Hiroshima University
  • OJIKA Makoto
    Graduate School of Bioagricultural Sciences, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya University

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  • Novel Cytotoxic Polyoxygenated Steroids from an Okinawan Sponge Dysidea sp

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Abstract

A library of extracts established from hundreds of marine organisms was screened by a cytotoxicity test. The active organic extract of an Okinawan marine sponge of the genus Dysidea was subjected to bioassay-guided fractionation to give three new polyoxygenated steroids dysideasterols F-H (1–3), together with two known related compounds (4 and 5). Their structures were confirmed by NMR and mass spectroscopic analyses. A characteristic structural feature of 2, 4 and 5 is an allylic epoxide, whereas this epoxide undergoes ring-opening by a neighbouring hydroxyl group to give a tetrahydrofuran ring in 1 and 3. All compounds 1–5 exhibited a similar cytotoxic effect with IC50 values of 0.15–0.3 µM against human epidermoid carcinoma A431 cells, demonstrating that the allylic epoxide moiety was not responsible for this cytotoxic effect.

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