Antifungal Activity of Isothiocyanates and Related Compounds

Abstract

Data are presented concerning the antifungal activity of 11 natural isothiocyanates and 27 synthetized analogues in Aspergillus niger, Penicillium cyclopium , and Rhizopus oryzae , as well as in 13 additional saprophytic and parasitic fungi. A remarkable antifungal activity was observed in some analogues of benzylisothiocyanate and β-phenylethylisothiocyanate. The latter-mentioned compounds have not been described previously. In the group of benzylisothiocyanates, a correlation, which was inversely proportional, was detected between ed 100 values for A. niger and R. oryzae and the corresponding molar solubilities of compounds in water. In contradistinction, no relationship was observed between antifungal activity and chemical reactivity of investigated derivatives.

Effects of Glucosinolate-Derived Isothiocyanates on Fungi: A Comprehensive Review on Direct Effects, Mechanisms, Structure-Activity Relationship Data and Possible Agricultural Applications

“…These studies began as early as the 1960s. The study by [ 51 ] tested various ITCs, including methyl, ethyl, isopropyl, 3-(methylsulfonyl)propyl, 4-(methylsulfonyl)butyl, 5-(methylthio)pentyl, benzyl, phenethyl, 4-methoxybenzyl ITC, as well as various synthetic ITCs like chlorinated aromatic ones on Aspergillus niger , Penicillium cyclopium , Rhizopus oryzae and other fungi. A 0.4–30 × potency was found compared to the reference allyl ITC; the highest activity was obtained with arylalkyl derivatives: phenethyl, 4-methoxybenzyl, and benzyl ITC.…”

“…While the chemical reactivity of ITCs [ 13 ] enables them to have high bioactivities, their persistance in soils is low for the same reason. ITCs react readily with thiols and amines in organic matter via chemical reactions [ 51 , 146 ], which results in reduced antifungal efficacy for ITCs when high amount of organic matter is present, as shown by [ 177 ]. This is very similar to the efficacy difference found between nucleophile-poor and nucleophile-rich media in [ 37 ].…”

Dietary Isothiocyanates, Sulforaphane and 2-Phenethyl Isothiocyanate, Effectively Impair Vibrio cholerae Virulence

“…Phytoncides are a wide group of plant secondary metabolites which are a source of compounds with biological activities, including antimicrobial action. Among them, isothiocyanates (ITC), produced by Brassicaceae plants, have been shown to be effective against pathogenic bacteria and fungi [16,17]. Sulforaphane (SFN) is an aliphatic ITC available in the daily diet and abundant in the seeds and sprouts of cruciferous plants, such as broccoli [18].…”

Η Επιδραση Χημικων Τροποποιητων Των Πρωτεινων Στη Δοκιμασια Ωσμωτικης Αιμολυσης Των Ερυθροκυτταρων

“…OL ίδιες ενώσεις έχουν χρησιμοποιηθεί καί γιά πρόκληση τοϋ πειραματικού αποφρακτικού ίκτερου (Schaffner et al, 1973). "Εχει δοκιμαστεί επίσης καί ένας μεγάλος αριθμός των ίσοθειοκυανικών εστέρων γιά πιθανή μυκητοκτόνο ενέργεια (Drobnica et al, 1967a(Drobnica et al, , 1967b.…”