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Epoxide and Hydroperoxide Derived from Naturally Cinnamaldehyde and its Schiff Base Derivatives
Corresponding Author(s) : Suzan A. Khayyat
Asian Journal of Chemistry,
Vol. 26 No. 19 (2014): Vol 26 Issue 19
Abstract
Thermal and photo epoxidation, photooxygenation reactions of cinnamaldehyde may be useful tool for the design of drugs to act as potent chemopreventation and anticancer agents. trans-Cinnamaldehyde was isolated from essential oil of cinnamon (Cinnamonum verum). It was subjected to oxidation reactions either photochemically with hydrogen peroxide or thermally with 3-chloro-peroxybenzoic acid. Schiff base derivative was synthesized through condensation reaction with aniline. It subjected to photooxidation reaction in the presence of tetraphenylporphin as singlet oxygen sensitizer. photochemically oxidation reaction gave the corresponding epoxy derivative together with cis-isomerisation. Whereas, thermally oxidation reaction resulted the corresponding epoxy derivative together with cinnamic acid. In addition, photooxidation reaction of Schiff base derivative led to 1-phenyl-3-phenyliminopropen-1-yl hydroperoxide through endoperoxide derivative. The primary tested of hydroperoxide derivative showed a moderate degree of DNA degradation. trans-Cinnamaldehyde and its derivatives can act as antioxidants. They were trapped the reactive oxygen species (ROS) to give the intermediated epoxides and hydroperoxide derivatives, which could be alkylated or damage DNA, proteins and other biological species.
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- T.P. Yoon, M.A. Ischay and J. Du, Nat. Chem., 2, 527 (2010); doi:10.1038/nchem.687.
- K. Fidaly, C. Ceballos, A. Falguières, M. Veitia, A. Guy and C. Ferroud, Green Chem., 14, 1293 (2012); doi:10.1039/C2GC35118H.
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- N.S. Shashidar, Ph.D. Thesis, Studies on Bioactive Natural Compounds for their Antimicrobial and Antioxidant Properties, Department of Microbiology, Osmania University, Hyderabad (2002).
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References
T.P. Yoon, M.A. Ischay and J. Du, Nat. Chem., 2, 527 (2010); doi:10.1038/nchem.687.
K. Fidaly, C. Ceballos, A. Falguières, M. Veitia, A. Guy and C. Ferroud, Green Chem., 14, 1293 (2012); doi:10.1039/C2GC35118H.
S.G. Kim, A. Liem, B.C. Stewart and J.A. Miller, Carcinogenesis, 20, 1303 (1999); doi:10.1093/carcin/20.7.1303.
S. Khayyat, J. Saudi. Chem. Soc., 17, 61 (2013); doi:10.1016/j.jscs.2011.07.014.
S. Ali, A.A. Khan, I. Ahmed, M. Musaddiq, K.S. Ahmed, H. Polasa, L.V. Rao, C.M. Habibullah, L.A. Sechi and N. Ahmed, Ann. Clin. Microbiol. Antimicrob., 4, 20 (2005); doi:10.1186/1476-0711-4-20.
P. Suresh, V.K. Ingle and L.V. Vijaya, J. Food Sci. Technol., 29, 254 (1992).
N.S. Shashidar, Ph.D. Thesis, Studies on Bioactive Natural Compounds for their Antimicrobial and Antioxidant Properties, Department of Microbiology, Osmania University, Hyderabad (2002).
K.S. Bilgrami, K.K. Sinha and A.K. Sinha, Indian J. Med. Res., 96, 171 (1992).
P. Pacheco, J. Sierra, G. Schmeda-Hirschmann, C.W. Potter, B.M. Jones and M. Moshref, Phytother. Res., 7, 415 (1993); doi:10.1002/ptr.2650070606.
R. Eilerman, Kirk-Othmer Encyclopedia of Chemical Technology (2000).
S. Khayyat, Aust. J. Bas. Appl. Sci., 5, 78 (2011).
J. He, W. Ma, W. Song, J. Zhao, X. Qian, S. Zhang and J.C. Yu, Water Res., 39, 119 (2005); doi:10.1016/j.watres.2004.09.006.
J. Zanardi, C. Leriverend, D. Aubert, K. Julienne and P. Metzner, J. Org. Chem., 66, 5620 (2001); doi:10.1021/jo015588m.
Ph.A. Wright and J. Abbot, Int. J. Chem. Kinet., 25, 901 (1993); doi:10.1002/kin.550251104.
Y. Hu, A. Harada and S. Takahashi, Synth. Commun., 18, 1607 (1988); doi:10.1080/00397918808081320.
E. Elgendy and S. Khayyat, Russ. J. Org. Chem., 44, 823 (2008); doi:10.1134/S1070428008060079.
A. Saddiq and S. Khayyat, Pestic. Biochem. Physiol., 98, 89 (2010); doi:10.1016/j.pestbp.2010.05.004.
E. Elgendy and S. Khayyat, Russ. J. Org. Chem., 44, 814 (2008); doi:10.1134/S1070428008060067.
A.I. Vogel, Elementary Practical Organic Chemistry, Great Britain, William Clowes & Sons, edn 2, vol. 1 (1975).