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J. Biol. Chem., Vol. 276, Issue 16, 12614-12623, April 20, 2001
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From the Institute of Biological Chemistry, Washington State
University, Pullman, Washington 99164-6340
Matairesinol is a central precursor in
planta in the biosynthesis of numerous lignans, including that of
the important antiviral and anticancer agent, podophyllotoxin. In
this study, the ~32-kDa NAD-dependent
secoisolariciresinol dehydrogenase, which catalyzes the
enantiospecific conversion of ( The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AF352734 and AF352735.
Secoisolariciresinol Dehydrogenase Purification,
Cloning, and Functional Expression
IMPLICATIONS FOR HUMAN HEALTH PROTECTION*,
)-secoisolariciresinol into ()-matairesinol in Forsythia intermedia, was purified
>6,000-fold to apparent homogeneity. The 831-base pair cDNA clone
encoding this 277-amino acid protein was next obtained from a
library constructed from F. intermedia stem tissue, whose
fully functional recombinant protein, produced by expression of this
cDNA in Escherichia coli, catalyzed the same
enantiospecific conversion via the corresponding lactol intermediate. A
homologous secoisolariciresinol dehydrogenase gene was also isolated
from a Podophyllum peltatum rhizome cDNA library, whose
834-base pair cDNA clone encoded a 278-amino acid protein with a
calculated molecular mass of ~32 kDa. Expression of this protein
in E. coli produced a fully functional recombinant protein
that also catalyzed the enantiospecific conversion of ()-secoisolariciresinol into ()-matairesinol via the intermediary lactol. Various kinetic parameters were defined and established conversion of the intermediary lactol as being rate-limiting. With this
overall enzymatic conversion now unambiguously defined, the entire
biochemical pathway to the lignans, secoisolariciresinol and
matairesinol, has been elucidated. Last, both secoisolariciresinol and
matairesinol are metabolized in the gut of mammals, following digestion
of high fiber dietary grains, seeds, and berries, into the so-called
"mammalian" lignans, enterodiol and enterolactone, respectively; these in turn confer significant protection against the
onset of breast and prostate cancers.
*
This research was supported in part by United States
Department of Agriculture Grant 99-35103-8037, the United States
Department of Agriculture McIntire-Stennis Program, and the Lewis B. and Dorothy Cullman and G. Thomas Hargrove Center for Land Plant
Adaptation Studies as well as a United States Department of
Energy-National Science Foundation Plant Biotechnology Research and
Training Center graduate assistantship (to H. C. P.).The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
The on-line version of this article (available at
http://www.jbc.org) contains additional experimental materials and references.
To whom correspondence should be addressed. Tel.: 509-335-2682;
Fax: 509-335-7643; E-mail: lewisn@wsu.edu.
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