MALDI‐TOF Mass Spectrometry of Oligomeric Food Polyphenols.

Reed, Jess D.; Krueger, Christian G.; Vestling, Martha M.

doi:10.1002/chin.200602273

Cited by 48 publications

(94 citation statements)

References 1 publication

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“…Other than pyranoanthocyanins, polymeric pigments are a potential source of long-term color stability [21]. Polymeric pigments are the condensation product of anthocyanins and flavanols [22] and most often detected by MALDI-TOF-MS [23][24][25].…”

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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show abstract

“…The molecules of gallic acid (170 Da) or ellagic acid, when present, can be lost with the hydrogen transfer, and a double bond in the glucose is formed [137]. Many important fragment ions were not observed by ESI-MS/MS, which could complicate their structural identification [162][163][164][165]. A complex fragmentation pattern obtained from < 300 Da is observed, which complements the information to identify them [59,137,160].…”

Section: Maldi-ms/ms To Identify Natural Productsmentioning

confidence: 94%

Untitled

2016

Planta Med

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“…Confirmation that fractions F 3 and F 4 contained 3,4,5 tri-O-galloylquinic acid as the sole component was obtained by using mass spectrometry and nuclear magnetic resonance spectroscopy (data not shown). The spectra for fractions purified by 17 . The calculated m/z ratio of 3,4,5 tri-O-galloyquinic acid together with a sodium ion is m/z 671, similarly the potassium ion adduct would have an ion at m/z 687.…”

Section: Analysis Of Polyphenols Using Liquid Chromatography and Massmentioning

confidence: 99%

Inhibition of HIV-1 and M-MLV reverse transcriptases by a major polyphenol (3,4,5 tri-O-galloylquinic acid) present in the leaves of the South African resurrection plant,Myrothamnus flabellifolia

Kamng'ona

Moore

Lindsey

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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MALDI‐TOF Mass Spectrometry of Oligomeric Food Polyphenols.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 48 publications

References 1 publication

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

Untitled

Inhibition of HIV-1 and M-MLV reverse transcriptases by a major polyphenol (3,4,5 tri-O-galloylquinic acid) present in the leaves of the South African resurrection plant,Myrothamnus flabellifolia

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