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Bioscience, Biotechnology, and Biochemistry Volume 62, 1998 - Issue 7
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Original Articles

Stereochemical Difference in Secoisolariciresinol Formation between Cell-free Extracts from Petioles and from Ripening Seeds of Arctium lappa L.

Shiro SUZUKIWood Research Institute, Kyoto University
,
Toshiaki UMEZAWAWood Research Institute, Kyoto University
&
Mikio SHIMADAWood Research Institute, Kyoto University
Pages 1468-1470 | Received 09 Apr 1998, Published online: 22 May 2014

  • 1) Umezawa, T., Davin, L. B., and Lewis, N. G., Formation of the lignan, (-)-secoisolariciresinol, by cell free extracts of Forsythia intermedia. Biochem. Biophys. Res. Commun., 171, 1008-1014 (1990).
  • 2) Umezawa, T., Davin, L. B., Yamamoto, E., Kingston, D. G. I., and Lewis, N. G., Lignan biosynthesis in Forsythia species. J. Chem. Soc., Chem. Commun., 1990, 1405-1408.
  • 3) Umezawa, T., Davin, L. B., and Lewis, N. G., Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. J. Biol. Chem., 266, 10210-10217 (1991).
  • 4) Davin, L. B., Bedgar, D. L., Katayama, T., and Lewis, N. G., On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor coniferyl alcohol. Phytochemistry, 31, 3869-3874 (1992).
  • 5) Katayama, T., Davin, L. B., and Lewis, N. G., An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry, 31, 3875-3881 (1992).
  • 6) Katayama, T., Davin, L. B., Chu, A., and Lewis, N. G., Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry, 33, 581-591 (1993).
  • 7) Chu, A., Dinkova, A., Davin, L. B., Bedgar, D. L., and Lewis, N. G., Stereospecificity of (+)-pinoresinol and (+)-lariciresinol from Forsythia intermedia. J. Biol. Chem., 268, 27026-27033 (1993).
  • 8) Ozawa, S., Davin, L. B., and Lewis, N. G., Formation of (-)-arctigenin in Forsythia intermedia. Phytochemistry, 32, 643-652 (1993).
  • 9) Umezawa, T., Kuroda, H., Isohata, T., Higuchi, T., and Shimada, M., Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana. Biosci. Biotech. Biochem., 58, 230-234 (1994).
  • 10) Paré P. W., Wang, H.-B., Davin, L. B., and Lewis, N. G., (+)-Pinoresinol synthase: a stereoselective oxidase catalysing 8,8′-lignan formation in Forsythia intermedia. Tetrahedron Lett., 35, 4731-4734 (1994).
  • 11) Dinkova-Kostva, A. T., Gang, D. R., Davin, L. B., Bedgar, D. L., Chu, A., and Lewis, N. G., (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. J. Biol. Chem., 271, 29473-29482 (1996).
  • 12) Davin, L. B., Wang, H.-B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S., and Lewis, N. G., Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science, 275, 362-366 (1997).
  • 13) Umezawa, T., and Shimada, M., Formation of the lignan (+)-secoisolariciresinol by cell-free extracts of Arctium lappa. Biosci. Biotech. Biochem., 60, 736-737 (1996).
  • 14) Shinoda, J., and Kawagoye, M., Über die Bestandteile des Arctium lappa L. Yakugaku Zasshi (in Japanese), 49, 565-575 (1929).
  • 15) Omaki, T., About the chemical structure of arctiin, Yakugaku Zasshi (in Japanese), 55, 816-827 (1935).
  • 16) Bradford, M. M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-254 (1976).
  • 17) Umezawa, T., and Shimada, M., Enantiomeric composition of (-)-pinoresinol, (+)-matairesinol and (+)-wikstromol isolated from Wikstroemia sikokiana. Mokuzai Gakkaishi, 42, 180-185 (1996).
  • 18) Okunishi, T., Umezawa, T., and Shimada, M., Stereochemistry of lignan biosynthesis in Wikstroemia sikokiana. Wood Research, 84, 25-27 (1997).
  • 19) Umezawa, T., Okunishi, T., and Shimada, M., Stereochemical diversity in lignan biosynthesis. Wood Research, 84, 62-75 (1997).
  • 20) Umezawa, T., Okunishi, T., and Shimada M., Stereochemical difference in lignan biosynthesis in Arctium lappa, Wikstroemia sikokiana, and Forsythia spp. In “ACS Symposium Series Volume 697, Lignin and Lignan Biosynthesis, “ eds. Lewis, N. G. and Sarkanen, S., American Chemical Society, Washington D.C., pp. 377-388 (1998).

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