Journal of the Chemical Society. Perkin transactions I p. 1411 - 1416 (1981)
Update date:2022-08-11
Topics:
Burns, Michael K.
Coffin, Jane M.
Kurobane, Itsuo
Vining, Leo C.
McInnes, A. Gavin
et al.
Aspergillus candidus growing in glucose-leucine-salts medium synthesized chlorflavonin (1) from isotopically labelled phenylalanine, cinnamate, benzoate, or acetate.Radioactivity from <β-14C>cinnamic acid and <α-14C> benzoic acid was incorporated less efficiently than that from L-<β-14C>phenylalanine but decarboxylation of 3-chlorosalicylic acid (3) formed by alkaline degradation of the chlorflavonin samples located all of the radioactivity at C-2 in the flavonoid. 4,5-Dimethoxyresorcinol (2), obtained by alkaline degradation of chlorflavonin labelled from sodium <1-14C>acetate and <α-14C>cinnamic acid, accounted for only part of the radioactivity.The label from both precursors was distributed between ring A and one or more of the C-3, C-4, and C-3 methoxy-carbon atoms. 13C N.m.r. spectrometry of chlorflavonin labelled from sodium <1-13C>acetate showed 13C incorporation into C-4, C-5, C-7, and C-8a.Sodium <1-13C0;1;1,2-13C1;0;1>acetate was incorporated intact into (C-3,C-4) and all adjacent pairs of ring-A carbon atoms.The results indicate a pathway of flavonoid biosynthesis differing from that of higher plants in that a C6-C1 precursor unit is condensed with four C2 units.In the route proposed, the heterocyclic ring is formed befor ring A is substituted at C-8 and while it is free to rotate at the enzyme surface.
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