Abstract
A novel quasi-dimeric oxidation product of (+)-catechin, formed during the radical-scavenging reaction that prevents lipid peroxidation, was isolated by chromatography, and its structure was elucidated by infrared, ultraviolet and1H and13C nuclear magnetic resonance spectra and mass spectrometry. It was 5′-[3-[3,4-(3′,5′-dihydroxy) benzo-8-oxo-2,7-dioxabicyclo [4.4.0] deca-3,9-dien-10-yl]acryloyl]-(+)-catechin. It is an unusual type of dimer of flavan-3-ol derivatives, which is different from the naturally formed dimer, procyanidin.
References
Fujita, Y., T. Yamane, M. Tanaka, K. Kuwata, J. Okuzumi, T. Takahashi, H. Fujiki and T. Okuda,J. Cancer Res. 80:503 (1989).
Yagi, K.,Lipid Peroxides in Biology and Medicine, Academic Press, New York, NY, 1982.
Burton, G.W., and K.U. Ingold,J. Am. Chem. Soc. 103: 6472 (1981).
Hirose, Y., H. Yamaoka and M. Nakayama,Agric. Biol. Chem. 54:567 (1990).
Kessler, H., C. Griessinger, J. Zarbock and H.R. Loosli,J. Mag. Res. 57:331 (1984).
Doddrell, D.M., D.T. Pegg and M.R. Bendall,Ibid. 48:323 (1982).
Doddrell, D.M., D.T. Pegg and M.R. Bendall,J. Chem. Phys. 77: 2745 (1982).
Hashimoto, F., G. Nonaka and I. Nishioka,Chem. Pharm. Bull. 37: 3255 (1989), and references cited therein.
Author information
Authors and Affiliations
About this article
Cite this article
Hirose, Y., Yamaoka, H. & Nakayama, M. A novel quasi-dimeric oxidation product of (+)-catechin from lipid peroxidation. J Am Oil Chem Soc 68, 131–132 (1991). https://doi.org/10.1007/BF02662334
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02662334