Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate

Abstract

Geranyl acetate (1) was oxidized thermally and photochemically using (mcpba, H2O2) respectively to obtain (E)-5-(3, 3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate (2) and 3-(2-(3, 3-dimethyloxiran-2-yl) ethyl)-3-methyloxiran-2-yl) methyl acetate (3). On the other hand, photooxygenation of 1 with tetraphenyl porphin (TPP) as a photo sensitizer gave corresponding acitic acid 2,6-bis-hydroperoxy-7-methyl-3-methylene-oct-7-enyl-ester (4), acitic acid 7-hydroperoxy-3,7-dimethyl-octa-2,5-dienyl ester (5) and Acitic acid 3-hydroperoxy-7-methyl-3,7-dimethyl-octa-1,6-dienyl ester (6). Antifungal studies were carried out on geranyl acetate and its derivatives. Studies on the antifungal activity especially Microsporum gypsum, Trichophyton vercossum and Candida tropicalis showed that geranyl acetate, its epoxide and hydroperoxide derivatives have good antifungal action. Keywords: Medicinal plants, Geranyl acetate, Hydroperoxide, epoxide, Photooxygenation, antifungal activity