Document Detail


Biosynthesis of vanillin via ferulic acid in Vanilla planifolia.
MedLine Citation:
PMID:  19817415     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
(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.
Authors:
Osamu Negishi; Kenji Sugiura; Yukiko Negishi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  57     ISSN:  1520-5118     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2009 Nov 
Date Detail:
Created Date:  2009-11-05     Completed Date:  2010-02-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9956-61     Citation Subset:  IM    
Affiliation:
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan. negishi@sakura.cc.tsukuba.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Benzaldehydes / chemistry,  metabolism*
Biosynthetic Pathways*
Coumaric Acids / chemistry,  metabolism*
Vanilla / chemistry,  metabolism*
Chemical
Reg. No./Substance:
0/Benzaldehydes; 0/Coumaric Acids; 0/glucovanillin; 1135-24-6/ferulic acid; 121-33-5/vanillin; 7400-08-0/4-coumaric acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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