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Chondropsin D, a New 37-Membered-Ring Macrolide Lactam from the Marine Sponge Chondropsis Species

2001; American Chemical Society; Volume: 64; Issue: 10 Linguagem: Inglês

10.1021/np0101907

1520-6025

Mohammad A Rashid, Charles L. Cantrell, Kirk R. Gustafson, Michael R. Boyd,

Microbial Natural Products and Biosynthesis

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.