Abstract
The biosynthesis of 31-norcyclolaudenone has been investigated in banana peel ( Musa sapientum L.) using 14CO 2, 2- 14C-acetic acid, 2- 14C-mevalonic acid and 2- 14C-(4R)-4- 3H 1-mevalonic acid. For incubation periods up to 6 days, carbon dioxide was the most effective precursor. Incubations with the doubly labeled mevalonic acid demonstrated initial removal of the 4α-methyl group of the 4,4-dimethyl triterpene precursor in the biosynthesis of 31-norcyclolaudenone. A mechanism has been proposed that is compatible with net inversion of the original 4β-methyl group to the 4α-position during the formation of this 4α-monomethyl-3-ketone. In addition, these studies have indicated that the C-24 hydrogen atom is retained during the C-24 methylation process which forms the 24-methyl-25(26)-en side chain. The hydrogen atom is presumably retained at C-24.
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