This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted 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 CrossRef Citing Articles via Google Scholar Google Scholar Articles by Stafford, H. A. Articles by Lester, H. H. Search for Related Content PubMed PubMed Citation Articles by Stafford, H. A. Articles by Lester, H. H. Agricola Articles by Stafford, H. A. Articles by Lester, H. H.

Articles

Incorporation of [¹⁴C]Phenylalanine into Flavan-3-ols and Procyanidins in Cell Suspension Cultures of Douglas Fir ¹

Reed College Biology Department, Portland, Oregon 97202

L-[¹⁴C]Phenylalanine, fed to cell suspension cultures of Douglas fir, (Pseudotsuga menziesii Franco) was incorporated simultaneously, but at different rates, into (+)-catechin, (–)-epicatechin, and procyanidins of increasing molecular weight. Asymmetric labeling of dimers and polymers was demonstrated, with more label appearing in the upper than in the lower or terminal unit. In addition, the total pool of free monomers was 10 to 30 times more highly labeled than was this lower, terminal unit of dimers and higher oligomers. Since the dimer, epicatechin-catechin, contained more label than catechin-catechin, it is concluded that the carbocation with the 2,3-cis stereochemistry of (–)-epicatechin was formed more rapidly than was that of the 2,3-trans type of (+)-catechin.