A reassignment of (-)-mycothiazole and the isolation of a related diol.
A reinvestigation of the thiazole constituents from Cacospongia mycofijiensis, collected in Vanuatu, yielded known mycothiazole (3) plus a new derivative, mycothiazole-4,19-diol (6). The E stereochemistry at Delta14,15 of 3 has been revised to Z and the structural features of 6 are elucidated. These compounds, which presumably arise by the action of a polyketide-nonribosomal peptide synthetase (PKS/NRPS) hybrid, possess cytotoxic properties that need further exploration.
Sonnenschein
Rachel N
RN
Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Johnson
Tyler A
TA
Tenney
Karen
K
Valeriote
Frederick A
FA
Crews
Phillip
P
D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D034261:Epothilones / Q000737:chemistry; D015394:Molecular Structure; D048630:Polyketide Synthases / Q000378:metabolism; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D053778:Thiazolidines; D009514:Vanuatu
D000438:Alcohols; D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D034261:Epothilones; D013844:Thiazoles; D053778:Thiazolidines; C508681:mycothiazole; D048630:Polyketide Synthases; C037067:latrunculin A; C093788:epothilone B