Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Paper
Novel Cytotoxic Polyoxygenated Steroids from an Okinawan Sponge Dysidea sp.
Sudhakar V. S. GOVINDAMBong-Keun CHOIYukio YOSHIOKAAkihiko KANAMOTOTakeshi FUJIWARATetsuji OKAMOTOMakoto OJIKA
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2012 年 76 巻 5 号 p. 999-1002

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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 (13), 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 15 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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© 2012 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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