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J Agric Food Chem. 2014 Nov 26;62(47):11536-46. doi: 10.1021/jf503330b. Epub 2014 Nov 13.

Novel pyrano and vinylphenol adducts of deoxyanthocyanidins in sorghum sourdough.

Author information

1
Department of Agricultural, Food and Nutritional Science, University of Alberta , Edmonton, Alberta T6G 2P5, Canada.

Abstract

This study determined the fate of deoxyanthocyanidins in sorghum sourdoughs. Sourdoughs prepared from the red sorghum variety Town were fermented with the caffeic acid-decarboxylating strains Lactobacillus plantarum FUA3171 and the decarboxylase negative L. casei FUA3166. Deoxyanthocyanidins were analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Apigeninidin and methoxyapigeninidin were the major deoxyanthocyanidins prior to fermentation. During fermentation, novel deoxyanthocyanidins were formed. Purification by preparative LC, followed by NMR analysis and high-resolution MS identified two of the compounds as 6-deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin. To identify pathways for their formation, sorghum was fermented with single strains, L. plantarum or L. casei. 6-Deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin were formed only during fermentation with L. plantarum FUA3171, indicating a role of vinylphenol in their formation. Chemical synthesis confirmed that 6-deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin are formed from apigeninidin with vinylphenol but not with p-coumaric acid as reactants. In conclusion, the products of microbial decarboxylation of hydroxycinnamic acids convert apigeninidin and methoxyapigeninidin to pyrano-3-deoxyanthocyanidins and vinylphenol adducts.

KEYWORDS:

caffeic acid decarboxylase; deoxyanthocyanidins; pyranoanthocyanins; sorghum; sourdough

PMID:
25370078
DOI:
10.1021/jf503330b
[Indexed for MEDLINE]

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