An LC-PDA-ESI/MS(n) profiling method was used to identify the anthocyanins of purple Bordeaux radish and led to the assignment of 60 anthocyanins: 14 acylated cyanidin 3-(glucosylacyl)acylsophoroside-5-diglucosides, 24 acylated cyanidin 3-sophoroside-5-diglucosides, and 22 acylated cyanidin 3-sophoroside-5-glucosides. The identifications were supported by the presence of 3-sophoroside-5-diglucoside and 3-sophroside-5-glucoside of cyanidin in the alkaline-hydrolyzed extract. A reliable method to identify the anthocyanins containing 3-(glucosylacyl)acylsophorosyl functions is described. The tentative identifications were obtained from tandem mass data analysis and confirmed by high-resolution mass measurements. Further assignments were made for some anthocyanins from a comparison of the mass and UV-vis data and elution order with those of the anthocyanins in the authors' polyphenol database and from consideration of the structural characteristics of the anthocyanins from similar plants and similar anthocyanins in the literature. The presence of 38 acylated cyanidin 3-sophoroside-5-diglucosides and around 10 acylated cyanidin 3-sophoroside-5-malonylglucosides in plants is reported here for the first time.
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http://dx.doi.org/10.1021/jf200571a | DOI Listing |
Int J Biol Macromol
January 2025
College of Landscape Architecture and Art, Northwest A & F University, Yangling, Shaanxi 712100, China; State Key Laboratory of Crop Stress Resistance and High-Efficiency Production, Northwest A & F University, Yangling, Shaanxi 712100, China. Electronic address:
Glycosylation modification of anthocyanins is important as a preceding step to acylation modification. Cyanidin-3-O-(p-coumaroyl)glucoside-5-O-malonylglucoside (Cy3pCG5MaG) is one of the major anthocyanin substances in blue-flowered grape hyacinth, but its 5-position glycosylation is unknown. Here, we identified two glycoside hydrolase family 1 genes, MaAGGT1 and MaAGGT5, which use acyl-glucose as a donor and are involved in the glycosylation modification of anthocyanins in grape hyacinth.
View Article and Find Full Text PDFFood Chem
February 2025
College of Food Science, Northeast Agricultural University, Harbin, Heilongjiang, 150030, China. Electronic address:
This study systematically evaluated the color-enhancing effects of different co-pigmented molecules (amino acids, peptides, flavonoids and phenolic acids) with cranberry anthocyanins under different environmental conditions (light, dark, high temperature and ascorbic acid) and their potential mechanisms by various means, such as degradation kinetics, color stability, H NMR spectroscopy, and structural simulation analyses. The results showed that the introduction of co-pigments induced a strong color-enhancing effect and bathochromic shift, inhibited the degradation of anthocyanins (9.34 % ∼ 45.
View Article and Find Full Text PDFJ Agric Food Chem
November 2024
LAQV - REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
In this work, the thermodynamics and kinetics of the reversible and irreversible processes of cyanidin 3,5--diglucoside and cyanidin 3--(2--glucosyl, 6--sinapoyl)glucoside-2--glucoside, 5--glucoside were studied by covering all pH range (holistic approach). The acylation (i) decreases the mole fraction of the colorless hemiketal in acidic medium and increases that of the colored quinoidal base, (ii) expands the pH domain of the flavylium cation, and (iii) moderately decreases the rate of tautomerization and isomerization of the neutral and monoanionic species. Degradation of cyanidin-3,5--diglucoside in a basic medium occurs in two distinct stages.
View Article and Find Full Text PDFMol Nutr Food Res
November 2024
Institute of Nutritional Science, Department of Nutritional Science, Justus-Liebig-University Giessen, Giessen, Germany.
Scope: Excessive activation of the nucleotide-binding oligomerization domain-like receptor pyrin domain-containing protein 3 (NLRP3) inflammasome contributes to chronic inflammation. Thus, targeting NLRP3 inflammasome activation by anthocyanins may prevent inflammatory diseases. Therefore, the present study determines the influence of a black carrot extract (BCE) with high amounts of acylated anthocyanins and their related phenolic acids on the NLRP3 inflammasome.
View Article and Find Full Text PDFJ Sci Food Agric
January 2025
College of Food Science and Nutritional Engineering, China Agricultural University; National Engineering Research Center for Fruit & Vegetable Processing; Key Laboratory of Fruit and Vegetable Processing, Ministry of Agriculture and Rural Affairs; Beijing Key Laboratory for Food Non-thermal Processing, Beijing, China.
Background: Synchronous degradation between anthocyanin and vitamin C was found in fruit and vegetable juice matrices. To investigate whether the C-ring of anthocyanin is the key site of this interaction, cyanidin with four different C-ring modifications (3-glucosylation, 3,5-diglucosylation, 6″-malonylation, pyranylation) was added to vitamin C-containing apple juice, and the changes of anthocyanin retention, vitamin C retention, color, antioxidative activity and differential metabolites were analyzed.
Results: The anthocyanin retention was in the order of pyranylation >6″-malonylation >3,5-diglucosylation >3-glucosylation.
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