Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Formation of Thioxopyrrolidines and Dithiocarbamates from 4-Methylthio-3-butenyl Isothiocyanates, the Pungent Principle of Radish, in Aqueous Media
Hiroki MATSUOKAYoshinori TODAKenji YANAGIAsaka TAKAHASHIKoichi YONEYAMAYasushi UDA
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1997 Volume 61 Issue 12 Pages 2109-2112

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Abstract

Reaction products of 4-methylthio-3-butenyl isothiocyanate (MTBI), the radish pungent principle, in aqueous media were identified and their antimicrobial activities were examined. A rapid degradation of MTBI in aqueous media afforded a mixture of 3-(hydroxy) methylene-2-thioxopyrrolidine (1), (Z)-3-(methylthio)-methylene-2-thioxopyrrolidine (2), its (E-isomer (3), methyl 4-methylthiobutyldithiocarbamate (4), methyl (Z)-4-methylthio-3-butenyldithiocarbamate (5), and its (E)-isomer (6). The products 1, 2, and 3 were detected at all pHs examined, while 4, 5, and 6 were formed at pH over 6.0. The formation of 4 from 6 was accompanied by an oxidation of methanethiol released from MTBI in aqueous media. Antimicrobial activities of 2 and 3 against all microbes examined were much lower than that of 1, which had MICs ranging from 50 to 400μg/ml. As for 4, 5, and 6, antifungal activities were comparable to that of 1, but little antibacterial activities were observed. The antimicrobial activities of the six products were considered to be far lower than that of MTBI.

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