Spiculoic acids A and B, new polyketides isolated from the Caribbean marine sponge Plakortis angulospiculatus.
[structure: see text] Two novel polyketides, spiculoic acids A (1) and B (2), have been isolated from extracts of the Caribbean marine sponge Plakortisangulospiculatus. The structures of 1 and 2 were elucidated by detailed analysis of spectroscopic data. Spiculoic acid A (1) showed in vitro cytotoxicity against human breast cancer MCF-7 cells. It has a putative polyketide biogenetic origin that involves incorporation of four butyrate units and a Diels Alderase catalyzed intramolecular [4 + 2] cycloaddition reaction.
Huang
Xin-Hui
XH
Departments of Chemistry, Earth & Ocean Sciences, University of British Columbia, Vancouver, BC V6T 1Z1.
van Soest
Rob
R
Roberge
Michel
M
Andersen
Raymond J
RJ
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007189:Indans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D007189:Indans; D018942:Macrolides; C490145:spiculoic acid A; C490146:spiculoic acid B