Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 24, Issue 22, Pages 5150-5153Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2014.10.002
Keywords
Phosphocalyculin C; Calyculin C; Discodermia calyx; Prodrug
Categories
Funding
- Nagase Science Technology Foundation
- Astellas Foundation for Research on Metabolic Disorders
- CREST Program from Japan Science and Technology Agency
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan
- Grants-in-Aid for Scientific Research [26303005, 25108705, 25560399] Funding Source: KAKEN
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Calyculin C, a minor derivative of the calyculins, has an additional methyl group on C32 of calyculin A. A recent biosynthetic study of calyculins revealed that an end product of calyculin biosynthesis is the pyrophosphate form, phosphocalyculin A. However, the pyrophosphate counterpart derived from calyculin C had not been reported. We isolated phosphocalyculin C as a minor pyrophosphate derivative, by a detailed investigation of an extract from the sponge Discodermia calyx. The treatment of phosphocalyculin C with the D. calyx cell-free extract significantly enhanced its cytotoxicity, providing molecular evidence for its role as the protoxin of calyculin C. (C) 2014 Elsevier Ltd. All rights reserved.
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