Biosynthesis of vanillin via ferulic acid in Vanilla planifolia.
(14)C-Labeled phenylalanine, 4-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from (14)C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the (14)C labels were also trapped by the unlabeled ferulic acid. However, (14)C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid --> --> ferulic acid --> --> vanillin --> glucovanillin in mature vanilla pods.
Negishi
Osamu
O
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan. negishi@sakura.cc.tsukuba.ac.jp
Sugiura
Kenji
K
Negishi
Yukiko
Y
D001547:Benzaldehydes / Q000737:chemistry / Q000378:metabolism*; D053898:Biosynthetic Pathways; D003373:Coumaric Acids / Q000737:chemistry / Q000378:metabolism*; D011422:Propionates; D031669:Vanilla / Q000737:chemistry / Q000378:metabolism*
D001547:Benzaldehydes; D003373:Coumaric Acids; D011422:Propionates; C004999:ferulic acid; C100058:vanillin; C443341:glucovanillin; C495469:p-coumaric acid