102 クワカルスにおけるDiels-Alder型付加化合物の一次代謝物からの生合成過程(ポスター発表の部)

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Biosynthesis of optically active Diels-Alder type adducts from primary metabolites in Morus alba callus cultures has been examined by the administration of ^<13>C_6-D-glucose and ^<13>C-labeled glycerols. Administration of ^<13>C_6-D-glucose to the M. alba callus cultures revealed that chalcomoracin (1) and kuwanon J (3) originates from two cinnamoylpolyketide + mevalonate units, respectively. In addition, the experiment indicated that the hydroxylation to the A and F rings of 1 corresponding to shikimate moiety takes place non-regioselectively after aromatization of the shikimate moiety. In an analogous experiment with [1,3-^<13>C_2]-glycerol, ^<13>C-labeled positions in the second and the third acetate units constructing the two isoprenyl units of 1 were opposite to those found in the starter acetate unit. The experiment with [2-^<13>C]-glycerol also gave the same result. The reversal way of the ^<13>C-labeling in the acetates constructing the mevalonate moiety has taken place presumably through the pentose phosphate cycle. In the M. alba callus cultures, the mevalonate has thus been biosynthesized from a glycolytically formed acetate as the starter acetate and the two successive acetates from the pentose phosphate cycle.
天然有機化合物討論会の論文
1992-09-10