Stability-increasing effects of anthocyanin glycosyl acylation

Zhao, Conghai; Yu, Yuqi; Chen, Zhongjian; Geyi, Wen; Wei, Fang; Zheng, Quan; Wang, Chong-De; Xiao, Xinglei

doi:10.1016/j.foodchem.2016.07.073

Cited by 274 publications

(161 citation statements)

References 70 publications

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“…Anthocyanin glycosyl acylation affects their chemical stability anthocyanins. Glycosyl acylation is one of the key factors for creating diversity within anthocyanins molecules and the types, numbers and linkage position of the acyl groups substantially increase the types of anthocyanins and their stability [59]. …”

Section: Anthocyanins Stability Factorsmentioning

confidence: 99%

The Effect of High Pressure Techniques on the Stability of Anthocyanins in Fruit and Vegetables

Marszałek

Woźniak

Kruszewski

et al. 2017

IJMS

122

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Anthocyanins are a group of phenolic compounds responsible for red, blue and violet colouration of many fruits, vegetables and flowers. The high content of these pigments is important as it influences directly their health promoting properties as well as the sensory quality of the product; however they are prone to degradation by, inter alia, elevated temperature and tissue enzymes. The traditional thermal methods of food preservation cause significant losses of these pigments. Thus, novel non-thermal techniques such as high pressure processing, high pressure carbon dioxide and high pressure homogenization are under consideration. In this review, the authors attempted to summarize the current knowledge of the impact of high pressure techniques on the stability of anthocyanins during processing and storage of fruit and vegetable products. Furthermore, the effect of the activity of enzymes involved in the degradation of these compounds has been described. The conclusions including comparisons of pressure-based methods with high temperature preservation techniques were presented.

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Section: Anthocyanins Stability Factorsmentioning

confidence: 99%

The Effect of High Pressure Techniques on the Stability of Anthocyanins in Fruit and Vegetables

Marszałek

Woźniak

Kruszewski

et al. 2017

IJMS

122

View full text Add to dashboard Cite

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“…The structural differences among anthocyanins are related [5,14,274,275] to the number of hydroxyl or methoxyl groups in the anthocyanidin skeleton, the position and the number of bonded sugar residues as well as by the aliphatic or aromatic carboxylates bonded to them. The hydroxylation pattern influences [276,277] physiological properties such as light absorption and antioxidative activity, which is the base for many beneficial health effects of flavonoids.…”

Section: Structure Of the Anthocyaninsmentioning

confidence: 99%

“…Note the diverse and complex chemistry of acyl groups and that their stabilizing effect exerted may be either independent or synergic. However, the acylation decreases the polarity of anthocyanins and creates steric hindrance effects (changing molecular size and spatial structure) to decrease the sensitivity of the anthocyanins to nucleophilic attack [274] and increasing the in vitro and in vivo chemical stability (though it lowers their apparent absorption) [113]. Nonacylated monoglycosylated anthocyanins have a greater inhibitory effect on human colorectal adenocarcinoma (HT29) cell proliferation [279]; anthocyanins with pelargonidin, triglycoside and/or acylation with cinnamic acid have a lesser effect.…”

Section: Flavonoids -From Biosynthesis To Human Healthmentioning

confidence: 99%

Antioxidant Capacity of Anthocyanin Pigments

Martín¹,

Kuskoski²,

Navas³

et al. 2017

Flavonoids - From Biosynthesis to Human Health

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Anthocyanins are a family of natural pigments classified into the group of flavonoids, considered to be responsible for the color and taste of many fruits and vegetables, i.e. berries. Anthocyanins are common components of the human diet. Besides their interest as colorant because of their coloring properties, the study of anthocyanin compounds stems from their wide applicability in the prevention and even in the treatment of various human diseases. However, various aspects of the pharmacological roles of anthocyanins remain in the dark, having still several obstacles to the development of robust diets or prescribing lines on consumption of anthocyanins. The chemical structure of anthocyanins determines in large measure its capacity and efficacy as an antioxidant agent. In this study, the following aspects are reviewed: the antioxidant effect of anthocyanin pigments; the oxidative stress, the bioavailability after intake and biological aspects of anthocyanins, the method for measuring the antioxidant activity of anthocyanins, the relationship between structure and activity; and the influence of the anthocyanins in the antioxidant activity of wines. Finally an overview of some potential uses in food industry is attempted mainly focusing in the anthocyanin encapsulation topic. Attention has been paid to the more recent publications in the field.

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“…Other common anthocyanin modifications of interest besides hydroxylation include O -methylation [19] and C -methylation [20], aliphatic acylation (acetylation and malonylation) or aromatic acylation (cinnamoylation, hydroxycinnamoylation, hydroxybenzoylation, etc.) [21], and various glycosylations with distinct hexose or pentose donors at different carbon positions on the core anthocyanin (including diglycosides or linear disaccharide/trisaccharide extensions at a single carbon on the core structure) [22–24]. These decorations are desirable because they increase product stability and thus facilitate characterization and quantification in complex matrices like cell cultures.…”

Section: Introductionmentioning

confidence: 99%

CRISPRi-mediated metabolic engineering of E. coli for O-methylated anthocyanin production

et al. 2017

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BackgroundAnthocyanins are a class of brightly colored, glycosylated flavonoid pigments that imbue their flower and fruit host tissues with hues of predominantly red, orange, purple, and blue. Although all anthocyanins exhibit pH-responsive photochemical changes, distinct structural decorations on the core anthocyanin skeleton also cause dramatic color shifts, in addition to improved stabilities and unique pharmacological properties. In this work, we report for the first time the extension of the reconstituted plant anthocyanin pathway from (+)-catechin to O-methylated anthocyanins in a microbial production system, an effort which requires simultaneous co-option of the endogenous metabolites UDP-glucose and S-adenosyl-l-methionine (SAM or AdoMet).ResultsAnthocyanin O-methyltransferase (AOMT) orthologs from various plant sources were co-expressed in Escherichia coli with Petunia hybrida anthocyanidin synthase (PhANS) and Arabidopsis thaliana anthocyanidin 3-O-glucosyltransferase (At3GT). Vitis vinifera AOMT (VvAOMT1) and fragrant cyclamen ‘Kaori-no-mai’ AOMT (CkmOMT2) were found to be the most effective AOMTs for production of the 3′-O-methylated product peonidin 3-O-glucoside (P3G), attaining the highest titers at 2.4 and 2.7 mg/L, respectively. Following modulation of plasmid copy number and optimization of VvAOMT1 and CkmOMT2 expression conditions, production was further improved to 23 mg/L using VvAOMT1. Finally, CRISPRi was utilized to silence the transcriptional repressor MetJ in order to deregulate the methionine biosynthetic pathway and improve SAM availability for O-methylation of cyanidin 3-O-glucoside (C3G), the biosynthetic precursor to P3G. MetJ repression led to a final titer of 51 mg/L (56 mg/L upon scale-up to shake flask), representing a twofold improvement over the non-targeting CRISPRi control strain and 21-fold improvement overall.ConclusionsAn E. coli strain was engineered for production of the specialty anthocyanin P3G using the abundant and comparatively inexpensive flavonol precursor, (+)-catechin. Furthermore, dCas9-mediated transcriptional repression of metJ alleviated a limiting SAM pool size, enhancing titers of the methylated anthocyanin product. While microbial production of P3G and other O-methylated anthocyanin pigments will likely be valuable to the food industry as natural food and beverage colorants, we expect that the strain constructed here will also prove useful to the ornamental plant industry as a platform for evaluating putative anthocyanin O-methyltransferases in pursuit of bespoke flower pigment compositions.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-016-0623-3) contains supplementary material, which is available to authorized users.

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Stability-increasing effects of anthocyanin glycosyl acylation

Cited by 274 publications

References 70 publications

The Effect of High Pressure Techniques on the Stability of Anthocyanins in Fruit and Vegetables

The Effect of High Pressure Techniques on the Stability of Anthocyanins in Fruit and Vegetables

Antioxidant Capacity of Anthocyanin Pigments

CRISPRi-mediated metabolic engineering of E. coli for O-methylated anthocyanin production

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