Journal
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
Volume 76, Issue 5, Pages 999-1002Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1271/bbb.120017
Keywords
cytotoxicity; sponge; Dysidea; marine natural product; steroid
Categories
Funding
- JSPS Kakenhi [23592962]
- Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) [090015]
- Grants-in-Aid for Scientific Research [24659894, 23592962, 24390456] Funding Source: KAKEN
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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 (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 mu M against human epidermoid carcinoma A431 cells, demonstrating that the allylic epoxide moiety was not responsible for this cytotoxic effect.
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