Antimicrobial volatile glucosinolate autolysis products from Hornungia petraea (L.) Rchb. (Brassicaceae)

• Published in: Phytochemistry letters Vol. 5; no. 2; pp. 351 - 357
• Main Authors: Radulović, Niko S., Dekić, Milan S., Stojanović-Radić, Zorica Z.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-06-2012
• Subjects: Antibacterial activity; antibacterial properties; antifungal properties; Antimicrobial activity; Antimicrobial agents; Aspergillus fumigatus; Autolysis; benzyl isothiocyanate; Brassicaceae; Candida albicans; Degradation products; gas chromatography-mass spectrometry; Glucosinolate; Glucosinolates; Hornungia petraea; Isothiocyanate; Metabolites; Micrococcus luteus; Minimum inhibitory concentration; mustard oil; plant tissues; Sarcina; Secondary metabolites; Volatiles; Isothiocyanate; Antimicrobial activity; Glucosinolate; Brassicaceae; Hornungia petraea
• ISSN: 1874-3900; 1876-7486
• DOI: 10.1016/j.phytol.2012.02.017

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► First analysis of Hornungia petraea glucosinolate (GLS) autolysis metabolites. ► The structure and identity of the detected GLS products were confirmed by synthesis. ► Antimicrobial assay suggests that the autolysis products serve as defense metabolites. ► High antibacterial activity of the tested isothiocyanates was shown against Sarcina lutea. ► Isothiocyanates also show an antifungal effect against Aspergillus fumigatus and Candida albicans.
Plant samples of Hornungia petraea were analyzed for glucosinolate (GLS) autolysis metabolites for the first time. GC–MS analysis of the autolysate and the synthesis of a series (12 compounds) of possible glucosinolate breakdown products revealed/corroborated the presence of glucoaubrietin, glucolimnanthin, glucolepigramin and glucotropaeolin in this species as the most likely “mustard oil” precursors. GLS degradation products identified in the autolysate of H. petraea, benzyl isothiocyanate, 3- and 4-methoxybenzyl isothiocyanate, along with several other structurally related compounds were evaluated for antimicrobial activity in order to possibly pinpoint the role of the latter secondary metabolites in the plant tissues. The assays showed a very high antibacterial activity of the tested isothiocyanates against Sarcina lutea and an antifungal effect against Aspergillus fumigatus and Candida albicans with MIC values in the order of 1μg/ml value.