Chondropsin D, a new 37-membered-ring macrolide lactam from the marine sponge Chondropsis species.
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.
Rashid
M A
MA
Molecular Targets Drug Discovery Program, Center for Cancer Research, National Cancer Institute-Frederick, Building 1052, Room 121, Frederick, MD 21702-1201, USA.
Cantrell
C L
CL
Gustafson
K R
KR
Boyd
M R
MR
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007769:Lactams / Q000737:chemistry; D007945:Leukemia, Lymphoid; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008545:Melanoma; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D007769:Lactams; D018942:Macrolides; C440684:chondropsin A; C440685:chondropsin B; C440683:chondropsin D