2000
DOI: 10.1021/np000252d
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Additional Cytotoxic Polyacetylenes from the Marine Sponge Petrosia Species

Abstract: Ten new polyacetylenic alcohols (1-6, 8-11), along with a known compound, petrocortyne C (7), were isolated from the marine sponge Petrosia sp. The gross structures were established based on NMR and MS data, and the absolute configuration was determined by the modified Mosher's method. These compounds displayed considerable cytotoxicity against a small panel of human solid tumor cell lines. Compounds 1-11 were further evaluated for in vitro inhibitory activity on DNA replication.

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Cited by 27 publications
(28 citation statements)
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“…The identification of the dideoxypetrosynols, petrotetrynols (30H, 30R-U, 30W), petrotriyndiol (30V), and the homologous and epimeric petrocortynes (30D-G, 30J, 30M, 30O, 30Q) greatly expanded the number of observed alcohol configurations, chain lengths, and levels of desaturation (Fig. 34) [327,[336][337][338], suggesting that this class of metabolites may be assembled from available unsaturated fatty acid or PK precursors and subjected to environmentally controlled or subspecies-dependent hydroxylation. It was proposed by Shin that hydroxide attack on the C-21 or C-27 alkenes followed by hydride abstraction was the origin of petrocortynes E-H (30I, 30L, 30N, 30P) [327].…”
Section: Marine Fatty Acids Andmentioning
confidence: 99%
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“…The identification of the dideoxypetrosynols, petrotetrynols (30H, 30R-U, 30W), petrotriyndiol (30V), and the homologous and epimeric petrocortynes (30D-G, 30J, 30M, 30O, 30Q) greatly expanded the number of observed alcohol configurations, chain lengths, and levels of desaturation (Fig. 34) [327,[336][337][338], suggesting that this class of metabolites may be assembled from available unsaturated fatty acid or PK precursors and subjected to environmentally controlled or subspecies-dependent hydroxylation. It was proposed by Shin that hydroxide attack on the C-21 or C-27 alkenes followed by hydride abstraction was the origin of petrocortynes E-H (30I, 30L, 30N, 30P) [327].…”
Section: Marine Fatty Acids Andmentioning
confidence: 99%
“…Interference with DNA synthesis has been mentioned to be a likely cause of their cytotoxicity [327].…”
Section: Marine Fatty Acids Andmentioning
confidence: 99%
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“…The polyacetylenes from Petrosia sp. [124] are unusual in several ways: two central triple bonds are non-conjugated connected by a carbonyl group, and they contain a terminal HC=CHOH.C= group that might plausibly undergo cationoid bromination.…”
Section: Polyacetylenesmentioning
confidence: 99%