Identification of novel pyranoanthocyanins in berry juices

Rein, Maarit J.; Ollilainen, Velimatti; Vahermo, Mikko; Yli‐Kauhaluoma, Jari; Heinonen, Marina

doi:10.1007/s00217-004-1063-6

Cited by 59 publications

(51 citation statements)

References 42 publications

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“…Then, polymeric pigments formed during processing may be generated by condensation of these pigments and flavan-3-ols and poliflavan-3-ols (Timberlake and Bridle 1976) and the formation of complexes between anthocyanins and phenolic acids (pyranoanthocyanins). Pyranoanthocyanins are orange pigments that have been detected during processing and aging of wines and sour cherry juice (Rentzsch et al 2007) and strawberry and raspberry juices (Rein et al 2005).…”

Section: Evaluation Of Anthocyanin Degradation and Browningmentioning

confidence: 99%

Color and Bioactive Compounds Characteristics on Dehydrated Sweet Cherry Products

Franceschinis

Sette

Schebor

et al. 2015

Food Bioprocess Technol

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It is widely known that quality properties of fruits can be affected by drying processes. The approach was the quality improvement of dried cherry products through the application of combined technologies of drying and pretreatments. The objective of this work was to analyze the effect of blanching or sugar infusion prior to air-drying or freezedrying on quality properties such as color, bioactive compounds, and antiradical power of two cherry products (discs and dices). Air-drying caused darkening, whereas freezedrying provoked higher lightness of discs compared to fresh fruit (p<0.05). Cherry dices were lighter than the fresh fruit. A high retention of total anthocyanin (ACY) and phenolic content (TPC) was obtained in blanched freeze-dried discs (ACY = 165 ± 22 mg Cyd-3-glu/100 g d.w.; TPC = 739 ± 55 mg GAE/100 g d.w.). Sugar infusion pretreatment caused an important decrease in ACY (31-89 mg Cyd-3-glu/100 g d.w.) and TPC (222-271 mg GAE/100 g d.w.). When blanching was applied prior to air-drying, samples presented the highest antiradical power, similar to that observed in fresh fruit. In dices, the best quality attributes in terms of superficial color were found in control freeze-dried samples since they presented minor shifts in hue angle and a greater preservation of anthocyanin pigments (ACY=211 ±30 mg Cyd-3-glu/ 100 g d.w.). However, control air-dried dices presented the highest phenolic content (TPC=771±65 mg GAE/100 g d.w.). Regarding the possible application of the dry cherry products, discs could be directly consumed as snacks, while dices could be incorporated as ingredients in fruit bars, cookies, or muffins.

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Section: Evaluation Of Anthocyanin Degradation and Browningmentioning

confidence: 99%

Color and Bioactive Compounds Characteristics on Dehydrated Sweet Cherry Products

Franceschinis

Sette

Schebor

et al. 2015

Food Bioprocess Technol

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“…In the past, a number of chemical syntheses of 4-vinyl derivatives of hydroxycinnamic acids have been described (Bernini, Mincione, Barontini, Provenzano, & Setti, 2007;Rein et al, 2005;Rizzi & Boekley, 1992). Our aim was to develop an efficient procedure to prepare compounds of adequate purity.…”

Section: Synthesis and Confirmation Of 4-vinyl Derivativesmentioning

confidence: 99%

“…Certain cinnamic acids behave as flavour precursors, since they break down and form new molecules with lower flavour thresholds (Rizzi & Boekley, 1992). These highly flavour-active volatile phenols, like 4-vinylphenol (4-VP) which originates from p-coumaric acid and 4-vinylguaiacol (4-VG), the decarboxylation product of ferulic acid, formed during thermal treatment and by enzyme activity, have been reported to influence the aroma and stabilise pigments of fruit juices (Fallico, Lanza, Maccarone, Asmundo, & Rapisarda, 1996;Rein, Ollilainen, Vahermo, Yli-Kauhaluoma, & Heinonen, 2005) and red wines (Morata, Gómez-Cordovés, Calderón, & Suárez, 2006). Some of the 4-vinyl derivatives of hydroxycinnamic acids, 4-VG and 4-vinylsyringol (4-VS), the latter the decarboxylation product of sinapic acid, are inherent to the beer production process, where they are formed by specific enzymes during fermentation or by thermal decarboxylation (Callemien, Dasnoy, & Collin, 2006;Vanbeneden, Gils, Delvaux, & Delvaux, 2008).…”

Section: Introductionmentioning

confidence: 99%

Antioxidant properties of 4-vinyl derivatives of hydroxycinnamic acids

et al. 2011

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“…Pyranoanthocyanins, which are anthocyanin conjugates with an additional pyran ring between C-4 and the 5-OH have been identified in several studies [13][14][15]. Pyranoanthocyanins can be formed from reactions between anthocyanins and fermentation products, such as acetaldehyde, pyruvic and acetoacetic acids [13,16], as well as hydroxycinnamic acids [17,18]. These compounds, which are consistent with the condensation product hypothesis proposed by Jurd [8] appear more pH stable [19] and have been detected in wine stored for several years [20].…”

Section: Introductionmentioning

confidence: 99%

Ascorbic acid-catalyzed degradation of cyanidin-3-O-β-glucoside: Proposed mechanism and identification of a novel hydroxylated product

Stebbins

Howard

Prior

et al. 2016

JBR

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Abstract. BACKGROUND:Many brightly colored fruits and vegetables owe their pigmentation and beneficial health effects to anthocyanins. Unfortunately, anthocyanins in the presence of ascorbic acid are readily degraded over juice processing and storage, which adversely affects color stability and potential health benefits. OBJECTIVE: This project focused on the effect of ascorbic acid as a catalyst in anthocyanin degradation. METHODS:The project involved searching for novel pigmented compounds in a simple model system composed of the most common anthocyanin cyanidin-3-O-␤-glucoside and ascorbic acid, and a second model system consisting of blackberry extract supplemented with ascorbic acid. Degradation products were identified by HPLC-PDA and HPLC-MS. ESR was used to monitor hydroxyl radical formation in the model systems. RESULTS: Over 72 hours at ambient temperature, 67% of cyanidin-3-O-␤-glucoside was lost in the model system during which time an unknown pigmented compound was formed. The unknown compound was also formed in a more complex model system consisting of blackberry extract and ascorbic acid. HPLC with PDA monitoring at 510 nm was used to detect a novel compound and HPLC-ESI-MS 3 allowed a proposed structure to be built based on the fragmentation patterns. The unknown structure formed via oxidation of cyanidin 3-O-␤-glucoside by ascorbic acid was identified as 6-hydroxy-cyanidin-3-O-␤-glucoside. The mechanism was substantiated with malvidin-3-O-␤-glucoside and ascorbic acid, which produced a hydroxylated malvidin-3-O-␤-glucoside. Production of hydroxyl radical in the base and blackberry model systems was confirmed by ESR. CONCLUSIONS: We propose that the pigmented compound is formed from hydroxyl radicals via the Haber-Weiss reaction. The addition of food grade hydroxyl radical scavengers to juices may be a viable treatment to prevent ascorbic acid-catalyzed degradation of anthocyanins.

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Identification of novel pyranoanthocyanins in berry juices

Cited by 59 publications

References 42 publications

Color and Bioactive Compounds Characteristics on Dehydrated Sweet Cherry Products

Color and Bioactive Compounds Characteristics on Dehydrated Sweet Cherry Products

Antioxidant properties of 4-vinyl derivatives of hydroxycinnamic acids

Ascorbic acid-catalyzed degradation of cyanidin-3-O-β-glucoside: Proposed mechanism and identification of a novel hydroxylated product

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