The formation of xanthylium salts from proanthocyanidins

Jurd, L.; Somers, T. C.

doi:10.1016/s0031-9422(00)85156-0

Cited by 75 publications

(55 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Evidence of the formation of xanthylium salts has been reported by Jurd and Somers (1970) in a model solution containing flavan-3,4-diols. A yellow pigment ( A, , , 453 nm) was isolated after acid treatment.…”

Section: Catechinmentioning

confidence: 85%

See 1 more Smart Citation

Interactions of Oligomeric Procyanidins in Model Wine Solutions Containing Malvidin-3-Glucoside and Acetaldehyde

Dallas¹,

Ricardo-da-Silva²,

Laureano³

1996

J. Sci. Food Agric.

View full text Add to dashboard Cite

Interactions of grape seed flavanols, dimeric, galloylated dimeric and trimeric procyanidins with malvidin‐3‐glucoside and acetaldehyde were studied in wine‐like model solutions. Malvidin‐3‐glucoside and oligomeric procyanidins reacted very slowly, with eventual formation of yellow xanthylium salts. The concentrations of malvidin‐3‐glucoside and oligomeric procyanidins decreased faster in the presence of acetaldehyde and the colour augmentation with shift towards violet was attributed to the formation of new coloured compounds, detectable by HPLC and linked at different positions by CH3CH bridges. The rate of loss of procyanidins in the presence of malvidin‐3‐glucoside and acetaldehyde varied according to the complexity of the components. Monomeric (+)‐catechin and (‐)‐epicatechin reacted more slowly than dimer procyanidins B1, B2 and B3 while trimer C1 (epicatechin 4β→8 epicatechin 4β→8 epicatechin) presented the highest degradative reaction rate.

show abstract

Section: Catechinmentioning

confidence: 85%

“…of reactions by which the colour of young wines may be A reaction mechanism and the initial position of linkage altered and stabilised during ageing have been sugwas proposed. gested (Jurd 1967;Jurd and Somers 1970;Ribereau-The procyanidins as a class of natural products have Gayon 1973).…”

Section: Introductionmentioning

confidence: 99%

Interactions of Oligomeric Procyanidins in Model Wine Solutions Containing Malvidin-3-Glucoside and Acetaldehyde

Dallas¹,

Ricardo-da-Silva²,

Laureano³

1996

J. Sci. Food Agric.

View full text Add to dashboard Cite

show abstract

“…From the shape of their absorption spectra, it is likely that those components have a xanthylium structure. It has been reported that procyanidins or catechins produce xanthylium pigments by polymerization in the presence of an organic acid (Labrouche, Clark, Prenzler & Scollary, 2005;Jurd & Somers, 1970).…”

Section: Changes In Polyphenolic Profile During Heat Treatmentmentioning

confidence: 99%

Heat treatment of Chinese quince polyphenols increases rat plasma levels of protocatechuic and vanillic acids

et al. 2010

View full text Add to dashboard Cite

The effect of heat-treated Chinese quince polyphenols on plasma antioxidant activity and the plasma levels of aromatic acids after oral administration to rats was investigated. The aqueous solution of Chinese quince polyphenols (CP) that had been extracted using 60%(v/v) acetone turned reddish during the heat treatment in the presence of citric acid. During the treatment, decreases in polymeric procyanidins and an increase in monomers, dimers and oligomers were observed. In the oral administration study, CP subjected to 2 h of heat treatment (CPT-2) caused a significant increase in antioxidant activity as assessed by the ferric reducing ability of plasma (FRAP) method. In addition, CP, CP + citric acid and CP subjected to 8 h of heat treatment (CPT-8) also tended to increase the FRAP value but the increase was not significant. Of the plasma aromatic acids detected, protocatechuic acid increased in all rats given the polyphenols. Vanillic acid increased significantly in rats given CPT-2 and CPT-8, reflecting a facilitatory effect of heat treatment on the intestinal absorption of protocatechuic acid and subsequent conversion by catechol-O-methyl transferase.These results suggested that the heat-induced breakdown of Chinese quince polyphenols seems to be an effective method of leading to an elevation of plasma antioxidant activity and levels of aromatic acid that are health-benefiting compounds derived from procyanidins.

show abstract

“…Their structures and contribution to the colour in ageing red wines were hypothesized in the late 1960s (Jurd, 1967(Jurd, , 1969Jurd & Somers, 1970;Somers, 1971). Two possible pathways were suggested for their formation:…”

Section: Introductionmentioning

confidence: 99%

“…(1) nucleophilic addition of the hemiketal form of an anthocyanin through their C-8 or C-6 positions at C-4 of a carbocation resulting from the cleavage of the interflavanic linkage of a flavanol oligomer; further conversion of the hemiketal form of the anthocyanin to the corresponding flavylium would yield F-A + adducts; (2) electrophilic substitution of the anthocyanin flavylium form (C-4) by a flavanol (C-8 or C-6) to yield an A-F dimer, where the anthocyanin moiety would be in the flavene form; this latter could oxidize to the corresponding flavylium form (A + -F adducts) or rearrange, either to a yellow xanthylium ion (Jurd & Somers, 1970;Liao, Cai, & Haslam, 1992; or to a doubly-linked A-F colourless structure containing an A-type interflavonoid bond (Bishop & Nagel, 1984;Remy-Tanneau, Le Guernevé, Meudec, & Cheynier, 2003). Detection, in red wines, of pigments showing molecular ions corresponding to either A + -F or F-A + adducts was first achieved by Vivar-Quintana et al (1999) using LC-MS and further confirmed by Salas et al (2004) who also found evidence in favour of the F-A + structure.…”

Section: Introductionmentioning

confidence: 99%

Flavanol–anthocyanin condensed pigments in plant extracts

et al. 2006

View full text Add to dashboard Cite

Pigments resulting from the direct condensation of anthocyanins and flavanols are usually associated with reactions taking place during processing and storage of plant-derived foods and beverages and have been particularly studied in aged red wines. In this paper, small amounts of flavanol-anthocyanin condensed pigments are found in different plant extracts. Structures are suggested for 10 such condensed pigments detected in extracts of strawberry, runner beans, purple corn and grape skins, based on their MS n fragmentation patterns, following analyses by electrospray tandem mass spectrometry. All of them correspond to dimers containing a flavan-3-ol [either (epi)afzelechin, (epi)catechin or (epi)gallocatechin] as the upper unit carbon-carbon linked to a lower anthocyanin unit consisting of different delphinidin, cyanidin, pelargonidin, peonidin or malvidin derivatives. The detection of these pigments in plant extracts may suggest that they are natural pigments and not products exclusively formed during storage and ageing of processed foods and beverages, as was previously assumed.

show abstract

The formation of xanthylium salts from proanthocyanidins

Cited by 75 publications

References 16 publications

Interactions of Oligomeric Procyanidins in Model Wine Solutions Containing Malvidin-3-Glucoside and Acetaldehyde

Interactions of Oligomeric Procyanidins in Model Wine Solutions Containing Malvidin-3-Glucoside and Acetaldehyde

Heat treatment of Chinese quince polyphenols increases rat plasma levels of protocatechuic and vanillic acids

Flavanol–anthocyanin condensed pigments in plant extracts

Contact Info

Product

Resources

About