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Published on: October 7, 2015
Chondropsin D, a new 37-membered-ring macrolide lactam from the marine sponge Chondropsis species
M A Rashid1, C L Cantrell, K R Gustafson
1Molecular Targets Drug Discovery Program, Center for Cancer Research, National Cancer Institute-Frederick, Building 1052, Room 121, Frederick, MD 21702-1201, USA.
Abstract:
Chondropsin D (2), a new 37-membered-ring macrolide lactam, was isolated as a minor constituent of an aqueous extract of the marine sponge Chondropsis sp. This sponge sample had previously been the source of chondropsins A (1) and B, two novel polyketide-derived macrolides with potent cytotoxic activity. The structure of 2 was initially deduced from analysis of spectral data. This assignment was supported by the observation that chondropsin A (1), which contains a 35-membered macrocyclic ring, could be converted to chondropsin D (2) by a base-catalyzed intramolecular transesterification reaction. Rearrangement of the methylated derivative of chondropsin A (3) to the corresponding methylated analogue of chondropsin D (4) confirmed the structure of 2.
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