Biosynthesis of Stizolobinic Acid and Stizolobic Acid in the Etiolated Seedlings of Stizolobium hassjoo

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Abstract
Incorporation of ʟ-[U-14C] phenylalanine, ʟ-[U-14C] tyrosine and ᴅʟ-[β-14C] 3,4-dihydroxyphenyl-alanine (DOPA) into stizolobinic acid, ʟ-β-(6-carboxy-α′-pyron-3-yl) -alanine, and stizolobic acid. ʟ-β-(6-carboxy-α′-pyron-4-yl)-alanine, was investigated as test precursors for these new types of amino acids in the epicotyls of etiolated seedlings of Stizolobium hassjoo. Radioactive stizolobinic acid and stizolobic acid resulted from administering labelled precursors were identified by colour reactions, radioautography and/or recrystallization to constant specific radioactivity. Radiolabelled stizolobic acid was subjected to alkaline hydrolysis and distribution pattern of the radioactivity was further examined in a degradation fragment of the amino acid. Proposed biosynthetic routes to stizolobinic or stizolobic acid from DOPA were empirically con­ firmed and the results are further discussed in relation to the possibility that phenylalanine may also be introduced into reaction sequences leading to the synthesis of both heterocyclic amino acids.

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