Synthesis and antifungal activity of sulfides, sulfoxides, and sulfones based on (1S)-(-)-β-pinene

Abstract

Attachment of 2-mercaptoethanol and thioglycolic acid methyl ester to the double bond of (1S)-(-)-b-pinene yielded pinane sulfides with the cis configuration. Oxidation of sulfides with m-chloroperbenzoic acid yielded the corresponding sulfoxides and sulfones. The resulting compounds were screened for antimycotic activity and the dynamics of changes in antifungal properties in sulfides-sulfoxide-sulfone series were studied.

Derivatization of Natural Compound β-Pinene Enhances Its In Vitro Antifungal Activity against Plant Pathogens

“…The compound β-pinene is a natural compound with antimicrobial activity [8,9,10] which can be used to participate in numerous chemical reactions. Masses of β-pinene derivatives can be synthesized by chemical modification, and some of these derivatives have been proved to have better antifungal activity [11,12,13,14,15,16,17]. For example, Li et al [14] synthesized three series of β-pinene-based derivatives, and tested their fungicidal activity against three agricultural fungi.…”

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

“…We have recently created a series of sulfur-containing terpenoids of varied structures with the large set of the functional groups (Ishmuratov et al, 2014 ). Moreover, we also demonstrated the anti-fungal, anti-inflammatory, anti-helicobacter, antimicrobial and other types of activities of sulfur-containing monoterpenoids (Nikitina et al, 2009 , 2010 , 2012a , b ; Gavrilov et al, 2010 ). Coagulation activity of these compounds has already been described in our previous publications (Kiselev et al, 2017 ; Nikitina et al, 2017a , b ).…”

Mutagenesis and Adaptation of the Psychrotrophic Fungus Chrysosporium pannorum A-1 as a Method for Improving β-pinene Bioconversion

“…Biotransformation of β-pinene (1% (v/v)) was performed on BM and on phosphate buffer, pH 6, containing 1% glucose, using 1.5 and 2.35 g of dry mass per L, respectively. The entire contents of three flasks were sacrificed each time at regular intervals (0, 12,24,36,48,60,72, and 96 h) to assay the products of biotransformation. Growth was followed by measuring the dry weight of mycelium.…”

“…β-Pinene is commercially available at US$ 36 per kg, whereas the price of its oxygenated derivative, trans-pinocarveol, can be as high as US$ 134,000 per kg [10,11]. There are data regarding the antimicrobial properties of β-pinene, used either as a purified chemical or as a constituent of essential oils [12,13]. Some studies have also demonstrated that β-pinene and trans-pinocarveol, contained in the oils, show various biological effects [14][15][16][17][18].…”