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An Extraordinary Accumulation of (-)-Pinoresinol in Cell-Free Extracts of Forsythia intermedia: Evidence for Enantiospecific Reduction of (+)-PinoresinolStereoselective and enantiospecific transformation mechanisms in lignan biogenesis are only now yielding to scientific inquiry: it has been shown that soluble cell-free preparations from Forsythia intermedia catalysis the formation of the enantiomerically pure lignan, (-)-secoisolariciresinol, when incubated with coniferyl alcohol in the presence of NAD(P)H and H2O2. Surprisingly, (-)-pinoresinol also accumulates in this soluble cell-free assay mixture in greater than 96% enantiomeric excess, even though it is not the naturally occurring antipode present in Forsythia sp. But these soluble cell-free preparations do not engender stereoselective coupling; instead, racemic pinoresinols are first formed, catalysed by an H2O2-dependent peroxidase reaction. An enantiospecific NAD(P)H reductase then converts (+)- pinoresinol, and not the (-)-antipode, into (-)-secoisolariciresinol. Stereoselective syntheis of(+)-pinoresinol from E-coniferyl alcohol is, however, catalysed by an insoluble enzyme preparation in F. suspensa, obtained following removal of readily soluble and ionically bound enzymes; no exogenously supplied cofactors were required other than oxygen, although the reaction was stimulated by NAD-malate addition. Thus, the overall biochemical pathway to enantiomerically pure (-)-secoisolariciresinol has been delineated.
Document ID
19970028837
Document Type
Reprint (Version printed in journal)
Authors
Katayama, Takeshi
(Washington State Univ. Pullman, WA United States)
Davin, Laurence B.
(Washington State Univ. Pullman, WA United States)
Lewis, Norman G.
(Washington State Univ. Pullman, WA United States)
Date Acquired
August 17, 2013
Publication Date
January 1, 1992
Publication Information
Publication: Phytochemistry
Volume: 31
Issue: 11
Subject Category
Life Sciences (General)
Report/Patent Number
NASA-CR-204933
NAS 1.26:204933
Funding Number(s)
CONTRACT_GRANT: USDA-91-3710-3-6638
CONTRACT_GRANT: NAG10-0086
Distribution Limits
Public
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