HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Umezawa, T. Articles by Lewis, N. G. Search for Related Content PubMed PubMed Citation Articles by Umezawa, T. Articles by Lewis, N. G. Social Bookmarking                      What's this?

J. Biol. Chem., Vol. 266, Issue 16, 10210-10217, Jun, 1991

Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts

T Umezawa, LB Davin and NG Lewis
Commonwealth Center for Wood Science, Virginia Polytechnic Institute and State University, Blacksburg 24061-0323.

In vivo labeling experiments of Forsythia intermedia plant tissue with [8-14C]- and [9,9-2H2,OC2H3]coniferyl alcohols revealed that the lignans, (-)-secoisolariciresinol and (-)-matairesinol, were derived from two coniferyl alcohol molecules; no evidence for the formation of the corresponding (+)-enantiomers was found. Administration of (+-)-[Ar- 3H]secoisolariciresinols to excised shoots of F. intermedia resulted in a significant conversion into (-)-matairesinol; again, the (+)-antipode was not detected. Experiments using cell-free extracts of F. intermedia confirmed and extended these findings. In the presence of NAD(P)H and H2O2, the cell-free extracts catalyzed the formation of (-)- secoisolariciresinol, with either [8-14C]- or [9,9-2H2,OC2H3]coniferyl alcohols as substrates. The (+)-enantiomer was not formed. Finally, when either (-)-[Ar-3H] or (+-)-[Ar-2H]secoisolariciresinols were used as substrates, in the presence of NAD(P), only (-)- and not (+)- matairesinol formation occurred. The other antipode, (+)- secoisolariciresinol, did not serve as a substrate for the formation of either (+)- or (-)-matairesinol. Thus, in F. intermedia, the formation of the lignan, (-)-secoisolariciresinol, occurs under strict stereochemical control, in a reaction or reactions requiring NAD(P)H and H2O2 as cofactors. This stereoselectivity is retained in the subsequent conversion into (-)-matairesinol, since (+)- secoisolariciresinol is not a substrate. These are the first two enzymes to be discovered in lignan formation.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				B. Youn, S. G. A. Moinuddin, L. B. Davin, N. G. Lewis, and C. Kang Crystal Structures of Apo-form and Binary/Ternary Complexes of Podophyllum Secoisolariciresinol Dehydrogenase, an Enzyme Involved in Formation of Health-protecting and Plant Defense Lignans J. Biol. Chem., April 1, 2005; 280(13): 12917 - 12926. [Abstract] [Full Text] [PDF]

				J. W. Lampe Isoflavonoid and Lignan Phytoestrogens as Dietary Biomarkers J. Nutr., March 1, 2003; 133(3): 956S - 964. [Abstract] [Full Text] [PDF]

				L. B. Davin and N. G. Lewis Dirigent Proteins and Dirigent Sites Explain the Mystery of Specificity of Radical Precursor Coupling in Lignan and Lignin Biosynthesis Plant Physiology, June 1, 2000; 123(2): 453 - 462. [Full Text]

				J. W. Lampe, D. R. Gustafson, A. M. Hutchins, M. C. Martini, S. Li, K. Wähälä, G. A. Grandits, J. D. Potter, and J. L. Slavin Urinary Isoflavonoid and Lignan Excretion on a Western Diet: Relation to Soy, Vegetable, and Fruit Intake Cancer Epidemiol. Biomarkers Prev., August 1, 1999; 8(8): 699 - 707. [Abstract] [Full Text]

				Z.-Q. Xia, M. A. Costa, H. C. Pelissier, L. B. Davin, and N. G. Lewis Secoisolariciresinol Dehydrogenase Purification, Cloning, and Functional Expression. IMPLICATIONS FOR HUMAN HEALTH PROTECTION J. Biol. Chem., April 13, 2001; 276(16): 12614 - 12623. [Abstract] [Full Text] [PDF]