Enzymatic synthesis of Vaccinium blue using vaccinoside as a bifunctional precursor

[Display omitted] •Both polyphenol oxidase and β-glucosidase were involved in VBP formation.•Vaccinoside played as a unique bifunctional precursor to form VBPs.•15 Amino acids helped to give VBPs (λmax 581–590 nm) of different hues.•Two synthesis pathways were proposed to interpret formation of VBPs...

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Bibliographic Details
Published in:Food chemistry 2024-05, Vol.439, p.138049-138049, Article 138049
Main Authors: Zhou, Jianqin, Qi, Ziyan, Yi, Ling, Zhang, Yang, Yan, Zhaowei, Zhang, Jian, Ge, Fei, Li, Yali, Liu, Jiangyun
Format: Article
Language:English
Subjects:
active ingredients
Amino acid
biosynthesis
black rice
Blue pigment
catechol oxidase
China
colorimetry
food chemistry
Iridoid Glycosides
Plant Extracts - chemistry
Polyphenol oxidase
rice protein
Vaccinium - chemistry
Vaccinium bracteatum
Vaccinium myrtillus - chemistry
Vaccinoside
β-glucosidase
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Summary:[Display omitted] •Both polyphenol oxidase and β-glucosidase were involved in VBP formation.•Vaccinoside played as a unique bifunctional precursor to form VBPs.•15 Amino acids helped to give VBPs (λmax 581–590 nm) of different hues.•Two synthesis pathways were proposed to interpret formation of VBPs. Since Tang dynasty in China, the fresh leaves of Vaccinium bracteatum (VBL) have been applied as natural pigment to produce black rice. However, detailed information on its biosynthetic mechanism still remained unclear. Following rice dyeing capacity assay, vaccinoside, one of iridoid glycosides, was identified as the key active compound. Increased methodical research demonstrated vaccinoside as a distinct bifunctional precursor, which could be catalyzed by polyphenol oxidase or β-glucosidase independently, followed by reaction with 15 amino acids to give blue pigments (VBPs; λmax 581–590 nm) of different hues. Two synthetic pathways of VBPs were proposed, using multiple techniques such as HPLC, HPSEC, UV–Vis spectrum and colorimeter as analysis tools. Black rice was interpreted to be prepared by cooking, using vaccinoside, intrinsic enzymes from fresh VBL and rice protein in combination. These findings promote the understanding of VBP formation mechanisms and provide an efficient method of producing novel Vaccinium blue pigments.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2023.138049