The interplay between antimicrobial activity and reactivity of isothiocyanates

Silvia Andini, Carla Araya-Cloutier, Leonie Waardenburg, Heidy M.W. den Besten, Jean Paul Vincken*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

9 Citations (Scopus)


This study aimed to determine antimicrobial activity (minimum inhibitory concentration, MIC; minimum bactericidal/fungicidal concentration, MBC/MFC) of novel ITCs against food spoilage and pathogenic Gram bacteria, Gram+ bacteria, and fungi. The activity of the long-chain (C9) 9-(methylthio)nonyl ITC (9-MTITC), 9-(methylsulfinyl)nonyl ITC (9-MSITC), and 9-(methylsulfonyl)nonyl ITC (9-MSoITC) was determined for the first time. Due to the electrophilicity of ITCs, the activity of ITCs was evaluated in nucleophile-rich and nucleophile-poor growth media. ITCs reacted via conjugation with components in a nucleophile-rich growth medium at a rate of 39–141 μmol L−1 h−1, depending on their side chain configuration and temperature. The reaction rates were lowered by a factor of 2–21 when using nucleophile-poor growth media. Consequently, the activity of ITCs was generally improved, with MSITC and MSoITC being the most positively affected (activity increased by a factor of > 4). 9-MSITC and 9-MSoITC had good activity (MIC ≤ 25 μg/mL) against Gram+ bacteria and fungi. The short-chained (C3) analogues had good activity against Gram+ bacteria and Gram bacteria. The highest bactericidal/fungicidal activity was obtained for 9-MSITC and 9-MSoITC (MBC/MFC 17.5–25 μg/mL). Overall, MSITC and MSoITC might be potential new natural food preservatives, but their reactivity with food matrix components should be considered.

Original languageEnglish
Article number109843
Publication statusPublished - Dec 2020


  • Antibacterial
  • Brassicaceae
  • Electrophilic
  • Food preservative
  • Glucosinolate


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