| Degradation products of cyanidin glycosides from tart cherries and their bioactivities. | |
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MedLine Citation:
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PMID: 11600045 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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 microM concentrations. However, at a test concentration of 50 microM, 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 microM concentrations. |
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Authors:
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N P Seeram; L D Bourquin; M G Nair |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: 49 ISSN: 0021-8561 ISO Abbreviation: J. Agric. Food Chem. Publication Date: 2001 Oct |
Date Detail:
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Created Date: 2001-10-15 Completed Date: 2001-12-05 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4924-9 Citation Subset: IM |
Affiliation:
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Bioactive Natural Products and Phytoceuticals, Department of Horticulture and National Food Safety and Toxicology Center, Michigan State University, East Lansing, Michigan 48824, USA. nairm@msu.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Anthocyanins
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chemistry*,
isolation & purification,
metabolism,
pharmacology Antioxidants / pharmacology Benzopyrans / chemistry*, metabolism, pharmacology Cells, Cultured Chromatography, High Pressure Liquid Colonic Neoplasms / prevention & control Cyclooxygenase 1 Cyclooxygenase 2 Cyclooxygenase 2 Inhibitors Cyclooxygenase Inhibitors / pharmacology Humans Hydroxybenzoic Acids / chemistry, isolation & purification, pharmacology Inflammation / prevention & control Isoenzymes / antagonists & inhibitors Magnetic Resonance Spectroscopy Membrane Proteins Prostaglandin-Endoperoxide Synthases Prunus / chemistry*, metabolism Tumor Cells, Cultured |
| Chemical | |
Reg. No./Substance:
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0/Anthocyanins; 0/Antioxidants; 0/Benzopyrans; 0/Cyclooxygenase 2 Inhibitors; 0/Cyclooxygenase Inhibitors; 0/Hydroxybenzoic Acids; 0/Isoenzymes; 0/Membrane Proteins; 0/cyanidin 3-rutinoside; 13306-05-3/cyanidin; 99-50-3/protocatechuic acid; EC 1.14.99.1/Cyclooxygenase 1; EC 1.14.99.1/Cyclooxygenase 2; EC 1.14.99.1/PTGS1 protein, human; EC 1.14.99.1/PTGS2 protein, human; EC 1.14.99.1/Prostaglandin-Endoperoxide Synthases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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