By G. Billek

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Additional resources for Biosynthesis of Aromatic Compounds. Proceedings of the 2nd Meeting of the Federation of European Biochemical Societies, Vienna, 21–24 April 1965

Example text

Malonyl-CoA is readily formed in higher plants from acetyl-CoA and CO2 (Hatsch and Stumpf, 1961). Since malonyl-D-tryptophan once formed is completely stable in plant tissue and cannot be cleaved into its components, this compound can serve as a good trap for acetyl-CoA in our case. It is also well suited because it allows a stepwise degradation of the malonic acid part. The degradation involves thermal decarboxylation of malonyl-D-tryptophan to acetyltryptophan. Acetyltryptophan is hydrolysed to acetic acid, and Schmidt degradation of the acetate follows.

It is quite clear that any label in position 2 of the precursors ( · in Fig. 8) would be lost if this mechanism really works. The results of our experiments with piceatannol, and furthermore the fact that all natural stilbenes investigated until now are formed in the same way, prove Seshadri's hypothesis to be incorrect. BIOSYNTHESIS OF PLANT STILBENES 43 Overlooking the whole field of plant stilbenes one has to say that seven out of twelve natural substances of similar structure have been checked and their biosynthesis follows the same pathway without any exception.

J. Physiol. 40, 449. L Y N E N , F . and T A D A , M . (1961) Angew. Chem. 73, 513. M A H E S H , V. B . and S E S H A D R I , T . R . (1954) / . Sei. Ind. Research {India) 13B, 835. R O B I N S O N , R . (1955) The Structural Relations of Natural Products, p. 7. Oxford: Clarendon Press. R u D L O F F , E. V O N and J O R G E N S E N , E . (1963) Phytochemistry 2, 297. S E S H A D R I , T . R . (1957) Curr. Sei. 26, 310. BILLEK, CHAPTER 5 BIOSYNTHESIS OF Cö-Ci COMPOUNDS M. H. Z E N K University of Munich, Germany AMONG the phenohc constituents of higher plants is an essential group of compounds, which occurs in all plants so far investigated, the aromatic C^-Ci compounds (Karrer, 1958; Gildemeister, 1961).

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