Zur Biogenese der Isoflavone

Abstract

With the aid of cinnamic acid-[3-14C] and DL-Phenylalanine-[1-14C] it has been demonstrated that the biogenesis of both biochanin-A (5.7-Dihydroxy-4′-methoxyisoflavone) and formononetin (7-Hydroxy-4′-methoxyisoflavone) in chana germ (Cicer arietinum L.) involves a phenyl migration like the one which has been found to occur in the biogenesis of formononetin in red clover. 4.4′.6′-Trihydroxychalcone-4′-glucoside-[β-14C] is incorporated into formononetin but not into biochanin-A, the entire radioactivity being localized in C-2 of formononetin. Thus it has been proven that a C6-C3-C6 compound can be converted into an isoflavone. Acetate-[1-14C] is incorporated almost exclusively into ring A of formononetin.