Synthesis of A-Type Proanthocyanidins and Their Analogues: A Comprehensive Review

Alejo-Armijo, Alfonso; Salido, Sofı́a; Altarejos, Joaquı́n

doi:10.1021/acs.jafc.0c03380

Cited by 23 publications

(28 citation statements)

References 90 publications

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“…There are two main types of proanthocyanidin oligomers, that is, A‐type and B‐type, in plants. However, the knowledge about the transformation of A‐type proanthocyanidins is still underdeveloped during processing, but there is evidence that B‐type proanthocyanidin dimers can oxidize to A‐type dimers under mild conditions (Alejo‐Armijo et al., 2020; Burger et al., 1990; Chen et al., 2014; Kondo et al., 2000; Osman & Wong, 2007). Some early authors proposed that B‐type proanthocyanidin form A‐type proanthocyanidin (oxidized procyanidins) through the C‐2 oxidation of the upper monomer (Figure 5), but the conversion rate is low (3%–12%) (Burger et al., 1990; Kondo et al., 2000).…”

Section: Reactivity Of Flavanols During Processingmentioning

confidence: 99%

Reactivity of flavanols: Their fate in physical food processing and recent advances in their analysis by depolymerization

Liu

Bourvellec

Guyot

et al. 2021

Comp Rev Food Sci Food Safe

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Flavanols, a subgroup of polyphenols, are secondary metabolites with antioxidant properties naturally produced in various plants (e.g., green tea, cocoa, grapes, and apples); they are a major polyphenol class in human foods and beverages, and have recognized effect on maintaining human health. Therefore, it is necessary to evaluate their changes (i.e., oxidation, polymerization, degradation, and epimerization) during various physical processing (i.e., heating, drying, mechanical shearing, high-pressure, ultrasound, and radiation) to improve the nutritional value of food products. However, the roles of flavanols, in particular for their polymerized forms, are often underestimated, for a large part because of analytical challenges: they are difficult to extract quantitatively, and their quantification demands chemical reactions. This review examines the existing data on the effects of different physical processing techniques on the content of flavanols and highlights the changes in epimerization and degree of polymerization, as well as some of the latest acidolysis methods for proanthocyanidin characterization and quantification. More and more evidence show that physical processing can affect content but also modify the structure of flavanols by promoting a series of internal reactions. The most important reactivity of flavanols in processing includes oxidative coupling and rearrangements, chain cleavage, structural rearrangements (e.g., polymerization, degradation, and epimerization), and addition to other macromolecules, that is, proteins and polysaccharides. Some acidolysis methods for the analysis of polymeric proanthocyanidins have been updated, which has contributed to complete analysis of proanthocyanidin structures in particular regarding their proportion of A-type proanthocyanidins and their degree of polymerization in various plants. However, future research is also needed to better extract and characterize high-polymer proanthocyanidins, whether in their native or modified forms.

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Section: Reactivity Of Flavanols During Processingmentioning

confidence: 99%

Reactivity of flavanols: Their fate in physical food processing and recent advances in their analysis by depolymerization

Liu

Bourvellec

Guyot

et al. 2021

Comp Rev Food Sci Food Safe

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“…Various plant-derived flavonoids from cranberry showed pronounced inhibitory effects on the development of liver fibrosis, including flavonoids, flavonol glycosides, anthocyanins, and PAs (Shi et al 2021 ). PAs are oligomers or polymers of monomeric flavan-3-ols produced naturally by flavonoid synthesis (Rauf et al 2019 ) and synthetically synthesized (Alejo-Armijo et al 2020 ). The principal components of PAs include catechin and epicatechin (Dong 2015 ).…”

Section: Introductionmentioning

confidence: 99%

“…The principal components of PAs include catechin and epicatechin (Dong 2015 ). Fruits (including berries), nuts, and spices are rich sources of PAs (Krenn et al 2007 ; Alejo-Armijo et al 2020 ). Pas have remarkable biological effects such as antioxidant (Lai et al 2018 ), immunomodulatory (Rauf et al 2019 ), and anti-apoptotic (Yin et al 2017 ) in several conditions.…”

Section: Introductionmentioning

confidence: 99%

Proanthocyanidins attenuated liver damage and suppressed fibrosis in CCl4-treated rats

Othman

EL-Missiry

Farag

et al. 2022

Environ Sci Pollut Res

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Liver damage and fibrosis are serious health problems without effective treatment. Proanthocyanidins (PAs) are flavonoids with several biological effects. We investigated the potential anti-fibrotic effect of proanthocyanidins on carbon tetrachloride (CCl4)-induced liver injury and fibrosis. Liver fibrosis was induced by oral administration of CCl4 three times a week for 5 and 9 weeks. PAs were daily administered in a dose of 500 mg/kg bw. Animals were divided into five groups: control groups, olive oil-treated group, Pas-treated group, CCl4-treated animals, and PAs + CCl4-treated rats. CCl4 and PAs were administered by gavage. Administration of CCl4 caused a significant elevation in alanine aminotransferase and aspartate aminotransferase activities, the concentration of alpha-2-macroglobulin, and bilirubin concentration. In addition, the protein and apolipoprotein contents were significantly decreased in the serum of CCl4-treated rats. These results were accompanied by histopathological alterations and increased inflammation, apoptosis, and DNA damage. Treatment with PAs caused remarkable regression of fibrosis and alpha-2-macroglobulin with improvement in histological characteristics of the liver after 5 and 9 weeks of intoxication. PAs could also maintain redox balance, evidenced by the prevention of lipid peroxidation and mitigation of the decrease in antioxidants. Treatment of intoxicated rats with PAs resulted in a significant decline in pro-inflammatory cytokines, including IL-6, IL-1β, and TNF-α in serum. This is associated with a remarkable decrease in apoptosis of hepatic cells shown by decreased levels of Bax, caspase-3, and -9, with increased Bcl-2. The protective effect of PAs was also evident by protecting DNA integrity in the intoxicated rats. PAs suppressed hepatic fibrosis, improved liver function and structure via modulating the interdependence between oxidative stress, inflammation, apoptosis, and DNA integrity in CCl4-treated rats.

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“…Due to the biomedical interest of C‐B1, its chemical synthesis has been a subject of interest for many years, [37] being successfully accomplished relatively few years ago [38] . However, it is known that biological studies on C‐B1 are still carried out using the product isolated from a particular natural source or from the commercial standard.…”

Section: Introductionmentioning

confidence: 99%

Recovery and Seasonal Variation of Cinnamtannin B‐1 from Laurel (Laurus nobilis L.) Pruning Wood Wastes

Alejo-Armijo

Ortega-Vidal

Salido

et al. 2022

Chemistry & Biodiversity

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Cinnamtannin B‐1 (C‐B1) is a commercially‐available trimeric A‐type procyanidin with remarkable cellular actions mainly derived from its high radical scavenging activity. C‐B1 is the main phenolic compound of laurel wood, which has previously been isolated by a combination of conventional chromatographic techniques. The first aim of this work was to find laurel trees containing as much C‐B1 as possible, and learn about the influence of variables, such as gender and harvest time, on the production of C‐B1 by the tree. It was found that all studied trees tend to give higher C‐B1 percentages in the May‐July period, from 6 % to 18 %, and lower ones around March (spring) and November (fall), from 1 % to 8 %. In a general way, it also seems that the female trees tend to produce a bit more C‐B1 (from 2.8 % to 17.3 %) than male ones (from 1.7 % to 13.4 %). In addition, eight minor phenolic compounds [(−)‐ent‐catechin (1), (−)‐ent‐epicatechin‐(4α→8)‐ent‐epicatechin (2), (epi)catechin‐(4→8)‐(epi)afzelechin‐(4→8)‐(epi)catechin (3), (+)‐epiafzelechin‐(4β→8)‐epicatechin (4), (−)‐epicatechin (5), (−)‐afzelechin‐(4α→8)‐epicatechin (6), (epi)afzelechin‐(4→8)‐(epi)afzelechin‐(4→8)‐(epi)catechin (7) and (+)‐epicatechin‐(4β→8,2β→O‐7)‐epicatechin‐(4β→8)‐catechin (C‐D1)] were found and quantified in the ethyl acetate extract of the wood samples. The second aim of this work was to improve the recovery of C‐B1 from laurel wood. The use of the fast centrifugal partition chromatography (FCPC) technique has allowed for a recovery of 96 % of a technical‐grade C‐B1 (64 % in a previous protocol using conventional column chromatography on silica gel and size‐exclusion chromatography).

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Synthesis of A-Type Proanthocyanidins and Their Analogues: A Comprehensive Review

Cited by 23 publications

References 90 publications

Reactivity of flavanols: Their fate in physical food processing and recent advances in their analysis by depolymerization

Reactivity of flavanols: Their fate in physical food processing and recent advances in their analysis by depolymerization

Proanthocyanidins attenuated liver damage and suppressed fibrosis in CCl4-treated rats

Recovery and Seasonal Variation of Cinnamtannin B‐1 from Laurel (Laurus nobilis L.) Pruning Wood Wastes

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