Antiradical and reductant activities of anthocyanidins and anthocyanins, structure–activity relationship and synthesis

Ali, Hussein M.; Almagribi, Wafaa; Al-Rashidi, Mona N.

doi:10.1016/j.foodchem.2015.09.003

Cited by 104 publications

(99 citation statements)

References 31 publications

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“…Eight anthocyanidins, seven anthocyanins and two synthesized 4′-hydroxy flaviliums DDPH, ABTS, hydroxyl radical scavenging activity, FRAP [20] Dried fruits and juices from chokeberry FRAP, ABTS [251] Protucatechuates DPPH, ORAC, CAT [252] Six deoxyanthocyanidins and cyaniding-3-glucoside DPPH, FRAP [253] Plant foods CUPRAC, ABTS [254] Anthocyanins from different varieties blueberries Inhibiting activity on lipid peroxidation, hydroxyl radical scavenging, superoxide anion radical, DPPH [255] Plan extracts DPPH, ABTS, AAPH [198] Commercial beverages (wines, beers, soft drinks and waters) TRAP, TEAC, FRAP [256] Popular antioxidants-rich US foods ABTS, DPPH [257] Commercially available vegetable juices (23) FRAP, DPPH, ABTS [258] Anthocyanidins, anthocyanidin-3-glucosides and portisins DPPH, FRAP [259] Plants extracts of industrial interest (30) DDPH, ABTS, FRAP, FRAP, SOD, ORAC [260] Food products ORAC, TEAC [231] Selected small fruits ABTS, FRAP, DPPH [204] Pulps of frozen fruits ABTS, DPPH, DMPD [190] CAT (conjugate autoxidizable assay); SOD (superoxide dismutase assay). Table 5.…”

Section: Samples Methods Referencesmentioning

confidence: 99%

“…In order to gather comprehensible information about the total antioxidant capacity of a food [184], at least two of these tests, and preferably all, should be combined, if possible, taking into account both the arguments for and against, and its applicability. Table 5 shows selected articles [20,190,198,204,231,[251][252][253][254][255][256][257][258][259][260] in which more than one criterion has been applied to real samples with practical purposes. Advantages and limitations of the most common chemical methods of determination of the antioxidant capacity are compiled in Table 6 [160, 161, 167, 171-173, 176, 184, 231, 261-263].…”

Section: Flavonoids -From Biosynthesis To Human Healthmentioning

confidence: 99%

“…The capacity of phenolic compounds to trap FR depends upon their structure, in particular, of the hydrogen atoms of the aromatic group that can be transferred to the FR [5,10,20,24,63,113] and of the capacity of the aromatic compound to cope with the uncoupling of electrons as a result of the surrounding displacement of the electrons-π system. As compared to other antioxidants, research on their health effects started more recently.…”

Section: Antioxidant Activity Of the Anthocyaninsmentioning

confidence: 99%

“…The anthocyanin and anthocyanidin health properties are due to their peculiar chemical structure, as they are very reactive towards ROS because of their electron deficiency [265][266][267][268][269]. The antioxidative properties of anthocyanidins have been recently explored; most of the widely distributed anthocyanidins and anthocyanins show more scavenging activity than that of the well-known strong antioxidants trolox and catechol [20]. The physicochemical characteristics of anthocyanins [83,90,91], that is structure and size of the molecules (number and position of hydroxyl and methoxyl groups), water solubility and acidity constants, can control their ability to cross biological barriers.…”

Section: Antioxidant Activity Of the Anthocyaninsmentioning

confidence: 99%

“…A glass of red wine provides around 115 mg of polyphenols, contributing towards a total intake of phenolic compounds of 1171 mg/person/day [18,19]. The antioxidant activity of anthocyanins is depending to a large extent with their chemical structure: number and position of the hydroxyl groups and the conjugated double bonds, as well as on the presence of electron donors in the structural ring [5,20]. …”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

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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Section: Samples Methods Referencesmentioning

confidence: 99%

Section: Flavonoids -From Biosynthesis To Human Healthmentioning

confidence: 99%

Section: Antioxidant Activity Of the Anthocyaninsmentioning

confidence: 99%

Section: Antioxidant Activity Of the Anthocyaninsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Antioxidant Capacity of Anthocyanin Pigments

Martín¹,

Kuskoski²,

Navas³

et al. 2017

Flavonoids - From Biosynthesis to Human Health

View full text Add to dashboard Cite

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Different processing methods on anthocyanin composition and antioxidant capacity in blueberry juice: Based on metabolomics and DFT analysis

Liu,

Ma,

Zhang

et al. 2024

eFood

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Blueberry juice is one of deep‐processed products of blueberries, anthocyanins are main bioactive substance in blueberry juice. However, anthocyanins have poor stability. Thermal, high pressure, electric field, magnetic field and cobalt source irradiation were used to treat blueberry juice, and then the treated blueberry juice composition and antioxidant capacity were determined to explore ways to better protect anthocyanins. Metabolomics was used to qualitatively and quantitatively analyze the anthocyanins in blueberry juice, a total of 54 anthocyanins were identified. Different processing methods of treatment did not significantly change the types of anthocyanins in blueberry juice. Their effects were mainly focused on the changes in content. By determining the antioxidant capacity of blueberry juice, it was found that there is more than a simple linear relationship between the total anthocyanin content of blueberry juice and its antioxidant capacity. Therefore, the structural parameters of the four main anthocyanin monomers of blueberry juice were calculated using density functional theory to predict the antioxidant capacity and the antioxidant capacity of the monomers was determined for validation. The effect of different treatments on the change of antioxidant activity of blueberry juice due to anthocyanin occupancy was explained using equivalent antioxidant. The results showed that the 1 kGy irradiation treatment had a better protective effect on the anthocyanins, whereas the change in the percentage of anthocyanins due to this treatment was the key factor for the change in their antioxidant capacity.

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Covalent and non‐covalent interaction of myofibrillar protein and cyanidin‐3‐O‐glucoside: focus on structure, binding sites and in vitro digestion properties

Liao,

Kang,

Zhang

et al. 2023

J Sci Food Agric

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BACKGROUNDThe aim of this study was to investigate the effects of covalent and non‐covalent interactions between myofibrillar protein (MP) and cyanidin‐3‐O‐glucoside (C3G) on protein structure, binding sites, and digestion properties. Four methods of inducing covalent cross‐linking were used in the preparation of MP‐C3G conjugates, including tyrosinase‐catalyzed oxidation, alkaline pH shift treatment, free radical grafting, and ultrasonic treatment. A comparison was made between MP‐C3G conjugates and complexes, and the analysis included sodium dodecyl sulfate‐polyacrylamide gel electrophoresis (SDS‐PAGE), C3G binding ratio, liquid chromatography–tandem mass spectrometry (LC–MS/MS), protein side‐chain amino acids, circular dichroism spectroscopy, three‐dimensional fluorescence, particle size, and in vitro simulated digestion.RESULTSCovalent bonding between C3G and amino acid side chains in MP was confirmed by LC–MS/MS. In covalent bonding, tryptophan residues, free amino groups and sulfhydryl groups were all implicated. Among the 22 peptides covalently modified by C3G, 30 modification sites were identified, located in lysine, histidine, tryptophan, arginine and cysteine. In vitro simulated digestion experiments showed that the addition of C3G significantly reduced the digestibility of MP, with the covalent conjugate showing lower digestibility than the non‐covalent conjugate. Moreover, the digestibility of protein decreased more during intestinal digestion, possibly because covalent cross‐linking of C3G and MP further inhibited trypsin targeting sites (lysine and arginine).CONCLUSIONCovalent cross‐linking of C3G with myofibrillar proteins significantly affected protein structure and reduced protein digestibility by occupying more trypsin binding sites. © 2023 Society of Chemical Industry.

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Antiradical and reductant activities of anthocyanidins and anthocyanins, structure–activity relationship and synthesis

Cited by 104 publications

References 31 publications

Antioxidant Capacity of Anthocyanin Pigments

Antioxidant Capacity of Anthocyanin Pigments

Different processing methods on anthocyanin composition and antioxidant capacity in blueberry juice: Based on metabolomics and DFT analysis

Covalent and non‐covalent interaction of myofibrillar protein and cyanidin‐3‐O‐glucoside: focus on structure, binding sites and in vitro digestion properties

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