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Original Articles

Effect of the Benzylic Structure of Lignan on Antioxidant Activity

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Pages 2283-2290 | Received 07 May 2007, Accepted 04 Jun 2007, Published online: 22 May 2014

  • 1) Yamauchi, S., Ina, T., Kirikihira, T., and Masuda, T., Synthesis and antioxidant activity of oxygenated furofuran lignans. Biosci. Biotechnol. Biochem., 68, 183–192 (2004).
  • 2) Yamauchi, S., Hayashi, Y., Kirikihira, T., and Masuda, T., Synthesis and antioxidant activity of olivil-type lignans. Biosci. Biotechnol. Biochem., 69, 113–122 (2004).
  • 3) 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).
  • 4) Yamauchi, S., Sugahara, T., Nakashima, Y., Okada, A., Akiyama, K., Kishida, T., Maruyama, M., and Masuda, T., Radical and superoxide scavenging activity of matairesinol and oxidized matairesinol. Biosci. Biotechnol. Biochem., 70, 1934–1940 (2006).
  • 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) 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).
  • 8) Ward, R. S., and Hughes, D. D., Oxidative cyclization of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate). Tetrahedron, 57, 2057–2064 (2001).
  • 9) Roy, S. C., Rana, K. K., and Guin, C., Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol monomethyl ether and furofuran lignans (±)-sesamin, (±)-eudesmin, (±)-piperitol methyl ether, (±)-pinoresinol, (±)-piperitol, and (±)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source. J. Org. Chem., 67, 3242–3248 (2002).
  • 10) Yamauchi, S., Okazaki, M., Akiyama, K., Sugahara, T., Kishida, T., and Kashiwagi, T., First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan. Org. Biomol. Chem., 3, 1670–1675 (2005).
  • 11) Rao, K. V., and Alvarez, F. M., Chemistry of Saururus cernuus. Part 13. Some reactions of the diarylbutane type neolignans. J. Nat. Prod., 48, 592–597 (1985).
  • 12) Hattori, M., Hada, S., Kawata, Y., Tezuka, Y., Kikuchi, T., and Namba, T., New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans. Chem. Pharm. Bull., 35, 3315–3322 (1987).
  • 13) Yamauchi, S., and Yamaguchi, M., Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by threo selective aldol condensation and stereoconvergent cyclization as the key reactions. Biosci. Biotechnol. Biochem., 67, 838–846 (2003).
  • 14) Badawi, M. M., Handa, S. S., Kinghorn, A. D., Cordell, G. A., and Farnsworth, N. R., Plant anticancer agents XXVII: antileukemic and cytotoxic constituents of Dirca occidentalis. J. Pharm. Sci., 72, 1285–1287 (1983).
  • 15) Sartorelli, P., Young, M. C. M., and Kato, M. J., Antifungal lignan from of the arils of Virola oleifera. Phytochemistry, 47, 1003–1006 (1998).
  • 16) Fonseca, S. F., Nielsen, L. T., and Ruveda, E. A., Lignans of Araucaria angustifolia and 13C NMR analysis of some phenyltetralin lignans. Phytochemistry, 18, 1703–1708 (1979).
  • 17) Masuda, T., Oyama, Y., Inaba, Y., Toi, Y., Arata, T., Takeda, Y., Nakamoto, K., Kuninaga, H., Nishizato, S., and Nonaka, A., Antioxidant-related activities of the ethanol extracts from edible and medicinal plants cultivated in Okinawa, Japan. J. Jpn. Soc. Food Sci. Technol. (in Japanese), 49, 652–661 (2002).

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