Structural assignment of poecillastrins B and C, macrolide lactams from the deep-water Caribbean sponge Poecillastra species.
Two new chondropsin-type macrolide lactams, poecillastrins B (1) and C (2), were isolated from aqueous extracts of the marine sponge Poecillastra sp. These trace metabolites were isolated in low yield (400-600 microg), and their structures were determined primarily by analysis of NMR data acquired using a cyrogenically cooled probe. High-quality 1D and 2D NMR data sets allowed complete assignment of the spectroscopic data and defined the new structures as 35-membered ring analogues of poecillastrin A (3). Compounds 1 and 2 showed potent cytotoxic activity against a human melanoma tumor cell line (LOX) with an IC50 value of less than 1 microg/mL.
Takada
Kentaro
K
Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, MD 21702-1201, USA.
Choi
Byoung W
BW
Rashid
Mohammad A
MA
Gamble
William R
WR
Cardellina
John H
JH
Van
Que N
QN
Lloyd
John R
JR
McMahon
James B
JB
Gustafson
Kirk R
KR
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001444:Bahamas; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007769:Lactams / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008545:Melanoma; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007769:Lactams; D018942:Macrolides; C519146:poecillastrin B; C519147:poecillastrin C