Degradation Products of Cyanidin Glycosides from Tart Cherries and Their Bioactivities

• Published in: Journal of agricultural and food chemistry Vol. 49; no. 10; pp. 4924 - 4929
• Main Authors: Seeram, Navindra P, Bourquin, Leslie D, Nair, Muraleedharan G
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.10.2001
• Subjects: Analytical, structural and metabolic biochemistry; Anthocyanins - chemistry; Anthocyanins - isolation & purification; Anthocyanins - metabolism; Anthocyanins - pharmacology; Antioxidants - pharmacology; Benzopyrans - chemistry; Benzopyrans - metabolism; Benzopyrans - pharmacology; Biological and medical sciences; Carbohydrates; Cells, Cultured; Chromatography, High Pressure Liquid; Colonic Neoplasms - prevention & control; Cyclooxygenase 1; Cyclooxygenase 2; Cyclooxygenase 2 Inhibitors; Cyclooxygenase Inhibitors - pharmacology; Food industries; Fruit and vegetable industries; Fundamental and applied biological sciences. Psychology; Humans; Hydroxybenzoates - chemistry; Hydroxybenzoates - isolation & purification; Hydroxybenzoates - pharmacology; Inflammation - prevention & control; Isoenzymes - antagonists & inhibitors; Magnetic Resonance Spectroscopy; Membrane Proteins; Miscellaneous; Other biological molecules; Prostaglandin-Endoperoxide Synthases; Prunus - chemistry; Prunus - metabolism; Tumor Cells, Cultured; Anthocyanin; Prostaglandin-endoperoxide synthase; Temperature; Stability; Fruit; Cherry; Enzyme; Rosaceae; Identification; Prunus cerasus; Dicotyledones; Angiospermae; Pigments; pH; Spermatophyta; Oxidoreductases; Fruit tree; Degradation product
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf0107508

The bioactive anthocyanins present in tart cherries, Prunus cerasus L. (Rosaceae) cv. Balaton, are cyanidin 3-glucosylrutinoside (1), cyanidin 3-rutinoside (2), and cyanidin 3-glucoside (3). Cyanidin (4) is the major anthocyanidin in tart cherries. In our continued evaluation of the in vivo and in vitro efficacy of these anthocyanins to prevent inflammation and colon cancer, we have added these compounds to McCoy's 5A medium in an effort to identify their degradation products during in vitro cell culture studies. This resulted in the isolation and characterization of protocatechuic acid (5), the predominant degradation product. In addition, 2,4-dihydroxybenzoic acid (6) and 2,4,6-trihydroxybenzoic acid (7) were identified as degradation products. However, these degradation products were not quantified. Compounds 5 − 7 were also identified as degradation products when anthocyanins were subjected to varying pH and thermal conditions. In cyclooxygenase (COX)-I and -II enzyme inhibitory assays, compounds 5 − 7 did not show significant activities when compared to the NSAIDs Naproxen, Celebrex, and Vioxx, or Ibuprofen, at 50 μM concentrations. However, at a test concentration of 50 μM, the antioxidant activity of protocatechuic acid (5) was comparable to those of the commercial antioxidants tert-butylhydroquinone (TBHQ), butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA), and superior to that of vitamin E at 10 μM concentrations. Keywords: Prunus cerasus; tart cherries; anthocyanins; cyanidin; degradation; antioxidant; cyclooxygenase