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Satoshi YAMAUCHI, Takuya SUGAHARA, Yuki NAKASHIMA, Akihiro OKADA, Koichi AKIYAMA, Taro KISHIDA, Masashi MARUYAMA, Toshiya MASUDA, Radical and Superoxide Scavenging Activities of Matairesinol and Oxidized Matairesinol, Bioscience, Biotechnology, and Biochemistry, Volume 70, Issue 8, 23 August 2006, Pages 1934–1940, https://doi.org/10.1271/bbb.60096
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Abstract
The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7′-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.
1) Osawa, T., Phenolic antioxidants in dietary plants as antimutagens. In “Phenolic Compounds in Food and Their Effects on Health II,” eds. Huang, M.-T., Ho, C.-T., and Lee, C. Y., American Chemical Society, Washington, DC, pp. 135–149 (1992).
2) Yamauchi, S., Ina, T., Kirikihira, T., and Masuda, T., Synthesis and antioxidant activity of oxygenated furofuran lignans. Biosci. Biotechnol. Biochem., 68, 183–192 (2004).
3) Yamauchi, S., Hayashi, Y., Kirikihira, T., and Masuda, T., Synthesis and antioxidant activity of olivil-type lignans. Biosci. Biotechnol. Biochem., 69, 113–122 (2004).
4) Yamauchi, S., Hayashi, Y., Nakashima, Y., Kirikihira, T., Yamada, K., and Masuda, T., Effect of benzylic oxygen on the antioxidant activity of phenolic lignans. J. Nat. Prod., 68, 1459–1470 (2005).
5) Eklund, P. C., Långvik, O. K., Wärnå, J. P., Salmi, T. O., Willför, S. M., and Sjöholm, R. E., Chemical studies on antioxidant mechanism and free radical scavenging properties of lignans. Org. Biomol. Chem., 3, 3336–3347 (2005).
6) Eklund, P. C., and Sjöholm, R. E., Oxidative transformation of the natural lignan hydroxymatairesinol with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Tetrahedron, 59, 4515–4523 (2003).
7) Ralph, J., Peng, J., Lu, F., Hatfield, R. D., and Helm, R. F., Are lignans optically active? J. Agric. Food Chem., 47, 2991–2996 (1999).
8) Moritani, Y., Fukushima, C., Ukita, T., Miyagishima, T., Ohmizu, H., and Iwasaki, T., Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: new syntheses of (+)-trachelogenin and (+)-guayadequiol. J. Org. Chem., 61, 6922–6930 (1996).