Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions

Abstract

Linalool (I) was extracted from Zingiber officinale. The oxidation of linalool using m-chloroperbenzoic acid at room temperature gave the mixture of 2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol (IIa) & 2-(5-methyl-5-vinyl- tetrahydro-furan-2-yl)-propan-2-ol (IIa′), which cannot be separated. Whereas, the photo-epoxidation of it using hydrogen peroxide gave the above mixture IIa/IIa′, beside 2,2,8-trimethyl-6-oxianyl-tetrahydro-pyran-3-ol (IIb). It was evaluated for anti-oxidant, using erythrocyte hemolysis and ABTS methods. It showed inhibitory effect in case of erythrocyte hemolysis and low inhibitory effect in case of ABTS method. Photosensitization reactions of linalool with tetraphenyl porphyrin or chlorophyll produced a mixture of two isomeric hydroperoxides, 7-hydroperoxy-3,7-dimethylocta-1,5-dien-3-ol (IIIa) & 6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol (IIIb), which can be successfully separated. On the other hand, the cytotoxic activity of linalool (I) was tested against epdermoid carcinoma (HEP2), it has medium effect. Whereas, in case of human prostate cancer (PC-3), it has weak effect. From this study concludes that ginger has good antioxidant potential and this spice can be used to produce novel natural antioxidants and flavoring agent like linalool which recommends it as an active therapy for humans. Monoterpene linalool abstract singlet oxygen (1O2) by photosensitization reactions to produce these hydroperoxides, which are caused relatively little oxidative DNA damage.