LC-PDA-ESI/MS(n) identification of new anthocyanins in purple Bordeaux radish ( Raphanus sativus L. variety).

J Agric Food Chem

Food Composition and Methods Development Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, U.S. Department of Agriculture, Building 161, BARC-East, 10300 Baltimore Avenue, Beltsville, Maryland 20705, USA.

Published: June 2011

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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jf200571aDOI Listing

Publication Analysis

Top Keywords

acylated cyanidin
20
anthocyanins
8
anthocyanins purple
8
purple bordeaux
8
bordeaux radish
8
method identify
8
identify anthocyanins
8
cyanidin 3-sophoroside-5-diglucosides
8
3-sophoroside-5-diglucosides acylated
8
cyanidin
6

Similar Publications

Two glycoside hydrolase family 1 proteins mediate glycosylated modification at the 5-position of anthocyanin in grape hyacinth.

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 PDF

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 PDF

Influence of Acylation by Hydroxycinnamic Acids on the Reversible and Irreversible Processes of Anthocyanins in Acidic to Basic Aqueous Solution.

J 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 PDF

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 PDF

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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!