Journal
MARINE DRUGS
Volume 12, Issue 2, Pages 1116-1130Publisher
MDPI AG
DOI: 10.3390/md12021116
Keywords
bromoindole; tunicate; Diazona cf formosa; cytotoxicity; isolation; structure elucidation; total synthesis
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Tanjungides A (1) (Z isomer) and B (2) (E isomer), two novel dibrominated indole enamides, have been isolated from the tunicate Diazona cf formosa. Their structures were determined by spectroscopic methods including HRMS, and extensive 1D and 2D NMR. The stereochemistry of the cyclised cystine present in both compounds was determined by Marfey's analysis after chemical degradation and hydrolysis. We also report the first total synthesis of these compounds using methyl 1H-indole-3-carboxylate as starting material and a linear sequence of 11 chemical steps. Tanjungides A and B exhibit significant cytotoxicity against human tumor cell lines.
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