Biosynthesis of Vanillin via Ferulic Acid in Vanilla planifolia

• Published in: Journal of agricultural and food chemistry Vol. 57; no. 21; pp. 9956 - 9961
• Main Authors: Negishi, Osamu, Sugiura, Kenji, Negishi, Yukiko
• Format: Journal Article Conference Proceeding
• Language: English
• Published: WASHINGTON American Chemical Society 11.11.2009; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Aroma and flavouring agent industries; Benzaldehydes - chemistry; Benzaldehydes - metabolism; biochemical compounds; Biological and medical sciences; biosynthesis; Biosynthetic Pathways; chemical analysis; chemical composition; Chemistry; Chemistry, Applied; Coumaric Acids - chemistry; Coumaric Acids - metabolism; enzyme activity; ferulic acid; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; glucovanillin; Life Sciences & Biomedicine; Physical Sciences; Propionates; Science & Technology; Vanilla - chemistry; Vanilla - metabolism; Vanilla planifolia; vanillin; ferulic acid; vanillin; Vanilla planifolia; biosynthesis; glucovanillin; ANDR; SUSPENSION-CULTURES; PHENYLPROPANOID METABOLISM; CHROMATOGRAPHY; EXTRACT; Monocotyledones; Orchidaceae; Phenolic acid; Angiospermae; Spice; Vanilla (food); Spermatophyta; Biosynthesis; Vanillin; Ferulic acid
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf901204m

14C-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 14C-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 14C labels were also trapped by the unlabeled ferulic acid. However, 14C-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.