Abstract
Two coumarin derivatives, esculetin-4-carboxylic acid methyl ester (1) and esculetin-4-carboxylic acid ethyl ester (2), have been isolated from the marine sponge Axinella cf. corrugata. Structure determination included analysis of spectroscopic data and total synthesis of compound 2. These are the first coumarin derivatives isolated from a marine sponge. The ethyl ester 2 was found to be an in vitro inhibitor of SARS 3CL-protease and an effective inhibitor of SARS-CoV replication in Vero cells at non-cytotoxic concentrations.
Highlights
In 2002 and 2003, several cases of a life-threatening respiratory disease that was named “severe acute respiratory syndrome” (SARS) were reported from Guangdong Province in mainland China, Hong Kong, Canada, and Vietnam.[1]
Esculetin-4-carboxylic acid methyl ester (1) displayed a molecular ion peak corresponding to its dimerized sodium adduct at m/z 495 (TOF/ESI-MS)
Considering the 13C NMR spectrum of 1 which displayed only eleven carbons, the molecular weight measurement indicated that either the compound presented internal symmetry or it was detected as a dimerized molecular ion
Summary
In 2002 and 2003, several cases of a life-threatening respiratory disease that was named “severe acute respiratory syndrome” (SARS) were reported from Guangdong Province in mainland China, Hong Kong, Canada, and Vietnam.[1]. Esculetin-4-carboxylic acid methyl ester (1) displayed a molecular ion peak corresponding to its dimerized sodium adduct at m/z 495 (TOF/ESI-MS). 495.0539) indicated the formula C H O Na. Considering the 13C NMR spectrum of 1 which displayed only eleven carbons, the molecular weight measurement indicated that either the compound presented internal symmetry or it was detected as a dimerized molecular ion.
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