The chemistry of anthocyanins, anthocyanidins and related flavylium salts

Iacobucci, Guillermo A.; Sweeny, James G.

doi:10.1016/s0040-4020(01)91542-x

Cited by 240 publications

(122 citation statements)

References 189 publications

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“…Two different mechanisms have been proposed for ascorbic acid (Asc) catalyzed degradation of anthocyanins. The first involves a condensation reaction between anthocyanins and other components, such as ascorbic or organic acids [3,8], and the second involves a radical mechanism leading to cleavage of the anthocyanin into phenolic acids [11,12]. Much of the research related to structural changes in anthocyanins has been conducted on wine.…”

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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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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“…Furthertection [1] , as laser dyes [2] and as potential photochemotherapeutic agents [3] . They also occur widely in nature [4] . It is more, analogous thiopyrylium and pyrylium cations can undergo similar transformations [11b] .…”

mentioning

confidence: 99%

Molecular Engineering of Benzo[b]pyrylium Salts by Indirect Electrophilic Substitution

Katritzky¹,

Czerney

Levell

et al. 1998

Eur. J. Org. Chem.

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“…All compounds are recrystallized in ethanol. [2,3-b] pyridine-3-carbonitrile (2): To a mixture of the 2-Amino-4-(2-hydroxynaphthyl)-8-methoxy-4H-chromene-3-carbonitrile 1 (1mmol) and malonitrile (1mmol) in DMF (5 mL) was added a few drops of piperidine. After refluxing for 24h, the resulting mixture was allowed to cool at room temperature and then diluted with cold water.…”

Section: Chemistrymentioning

confidence: 99%

“…In recent years, there has been increasing interest in chromenes not only because they constitute a group among the major classes of naturally occurring compounds such as natural alkaloids, flavonoids, tocopherols and anthocyanins [1][2][3][4] , but also because of their versatility as synthones in organic transformations to give molecules having value as human therapeutic agents [5][6] . Among different types of chromene systems, 2-amino-4H-chromenes are of particular utility due to highly pronounced spasmolitic-, diuretic-, anticoagulant-and antianaphylactic activities [7][8][9] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of 2-amino chromenes arising cyanoiminocoumarins and β-naphthol

Dammak¹,

Kammoun²,

Allouche³

et al. 2017

Org. Commun.

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Abstract:The synthesis of 2-amino chromene, reported in our previous paper, has been accomplished by the reaction of cyanoiminocoumarin and β-naphthol. The obtained compound was reacted with various electrophilic or nucleophilic reagents. All the new homologous 2-amino-4H-chromenes have been characterized on the basis of their spectral (IR, 1 H and 13 C NMR) data and microanalysis. Four compounds were evaluated in vitro for their preliminary antibacterial activities against five different pathogenic bacterial strains such as Bacillus thuringiensis, Escherichia coli, Staphylococcus aureus, klebsiella pneumonia and Salmonella Sp. Antibacterial activity of each compound was compared with standard drug, Penicillin.

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The chemistry of anthocyanins, anthocyanidins and related flavylium salts

Cited by 240 publications

References 189 publications

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

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

Molecular Engineering of Benzo[b]pyrylium Salts by Indirect Electrophilic Substitution

Synthesis and antibacterial activity of 2-amino chromenes arising cyanoiminocoumarins and β-naphthol

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