2, 3-Dideoxyglucosides of selected terpene phenols and alcohols as potent antifungal compounds. (1st November 2016)

• Record Type: Journal Article
• Authors: James Bound, D.; Murthy, Pushpa S.; Srinivas, P.
• Is Part Of: Food chemistry. Volume 210(2016)
• Page Start: 371
• Page End: 380
• Publication Date: 2016-11-01
• Subjects: 2, 3-Deoxyglucosides -- Spices -- Phenols -- Terpene alcohols -- Antifungal -- Antitoxigenic; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2016.04.127
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: The novel 2, 3-unsaturated 1- O -glucosides of phenols are potent antifungal agents. The derivatives had lower MIC and MFC values compared to the parent molecules. 2, 3-Unsaturated 1- O -glucosides of phenols inhibited OTA/aflatoxin B2 formation. Carvacrol and its 2, 3-unsaturated 1- O -glucoside lysed C. albicans cell membrane. Abstract: The antifungal activities of novel 2, 3-unsaturated and 2, 3-dideoxy 1- O -glucosides of carvacrol, thymol, and perillyl alcohol were tested against Aspergillus flavus, Aspergillus ochraceus, Fusarium oxysporum, Saccharomyces cerevisiae and Candida albicans . In the agar well diffusion tests, zones of inhibition for the derivatives of carvacrol, thymol and perillyl alcohol were higher (15–30 mm) in the case of filamentous fungi than those for the parent compounds. Their MIC and MFC values indicated that the 2, 3-unsaturated and 2, 3-dideoxy 1- O -glucosides of carvacrol and thymol exhibited more fungicidal activity than the other compounds. Further, the 2, 3-dideoxyglucosides of carvacrol and thymol, exhibited antitoxigenic effects against A. ochraceus and A. flavus and inhibited the production of ochratoxin and aflatoxin-B2. Propidium iodide influx assay demonstrated the lysis of C. albicans cells by carvacrol and its 2, 3-unsaturated 1- O -glucoside and the loss of the membrane integrity. These new 2, 3-dideoxyglucosides can be useful as antifungal agents and condiments in foods.