Transformation of proanthocyanidin A2 to its isomers under different physiological pH conditions and common cell culture medium

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 11, 2011, Pages 6214-6220

  Lu, Wen Chien ^a   Huang, Wei Ting ^a   Kumaran, Alaganandam ^a   Ho, Chi Tang ^a,b   Hwang, Lucy Sun ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

b DMEM medium; isomers; physiological pH conditions; proanthocyanidin A2

Indexed keywords

ACIDIC CONDITIONS; ALKALINE CONDITIONS; ANIMAL MODEL; ANTIOXIDANT CAPACITY; B-DMEM MEDIUM; CELL CULTURE MEDIUMS; CULTURE SYSTEMS; EPICATECHIN; EPIMERIZATION; ETHYLENEDIAMINETETRAACETIC ACID; IN-VITRO; PH CONDITION; PHYSIOLOGICAL PH; PHYSIOLOGICAL PH CONDITIONS; POLYPHENOLS; PROANTHOCYANIDIN A2; PROANTHOCYANIDINS;

ALKALINITY; CELLS; ISOMERS; ORGANIC COMPOUNDS; PH EFFECTS; PHENOLS; PHYSIOLOGY;

ANIMAL CELL CULTURE;

PLANT EXTRACT; PROANTHOCYANIDIN;

ARTICLE; BIOAVAILABILITY; BIOLOGICAL MODEL; BIOTRANSFORMATION; CHEMISTRY; CULTURE MEDIUM; CURCUMA LONGA; DIGESTIVE SYSTEM; HUMAN; ISOMERISM; KINETICS; METABOLISM; PH;

BIOLOGICAL AVAILABILITY; BIOTRANSFORMATION; CULTURE MEDIA; CURCUMA; DIGESTIVE SYSTEM; HUMANS; HYDROGEN-ION CONCENTRATION; ISOMERISM; KINETICS; MODELS, BIOLOGICAL; PLANT EXTRACTS; PROANTHOCYANIDINS;

ANIMALIA;

EID: 79957986531     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104973h     Document Type: Article

References (20)

1. Kondo, K.; Kurihara, M.; Fukuhara, K.; Tanaka, T.; Suzuki, T.; Miyata, N.; Toyoda, M. Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation Tetrahedron Lett. 2000, 41, 485-488 (Pubitemid 30059254)
2. Osman, A. M.; Wong, K. K. Y. Laccase (EC 1.10.3.2) catalyses the conversion of procyanidin B-2 (epicatechin dimer) to type A-2 Tetrahedron Lett. 2007, 48, 1163-1167 (Pubitemid 46097049)
3. Hsieh, M. C.; Shen, Y. J.; Kuo, Y. H.; Hwang, L. S. Antioxidative activity and active components of longan (Dimocarpus longan Lour.) flower extracts J. Agric. Food Chem. 2008, 56, 7010-7016
4. Ho, S. C.; Hwang, L. S.; Shen, Y. J.; Lin, C. C. Suppressive effect of a proanthocyanidin-rich extract from longan (Dimocarpus longan Lour.) flowers on nitric oxide production in LPS-stimulated macrophage cells J. Agric. Food Chem. 2007, 55, 10664-10670
5. Tsai, H. Y.; Wu, L. Y.; Hwang, L. S. Effect of a proanthocyanidin-rich extract from longan flower on markers of metabolic syndrome in fructose-fed rats J. Agric. Food Chem. 2008, 56, 11018-11024
6. Sang, S.; Lee, M. J.; Hou, Z.; Ho, C. T.; Yang, C. S. Stability of tea polyphenol (-)-epigallocatechin-3-gallate and formation of dimers and epimers under common experimental conditions J. Agric. Food Chem. 2005, 53, 9478-9484 (Pubitemid 41784153)
7. Scott, P. M.; Lawrence, J. W.; Walbeek, W. v. Detection of mycotoxins by thin-layer chromatography: application to screening of fungal extracts Appl. Microbiol. 1970, 20, 839-842
8. Zhu, Q. Y.; Holt, R. R.; Lazarus, S. A.; Ensunsa, J. L.; Hammerstone, J. F.; Schmitz, H. H.; Keen, C. L. Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa J. Agric. Food Chem. 2002, 50, 1700-1705 (Pubitemid 34233250)
9. Hong, J.; Lu, H.; Meng, X.; Ryu, J.-H.; Hara, Y.; Yang, C. S. Stability, cellular uptake, biotransformation, and efflux of tea polyphenol (-)-epigallocatechin-3-gallate in HT-29 human colon adenocarcinoma cells Cancer Res. 2002, 62, 7241-7246 (Pubitemid 36025245)
10. Yoshino, K.; Suzuki, M.; Sasaki, K.; Miyase, T.; Sano, M. Formation of antioxidants from (-)-epigallocatechin gallate in mild alkaline fluids, such as authentic intestinal juice and mouse plasma J. Nutr. Biochem. 1999, 10, 223-229 (Pubitemid 29146061)
11. Ishino, N.; Yanase, E.; Nakatsuka, S. i. Epimerization of tea catechins under weakly acidic and alkaline conditions Biosci., Biotechnol., Biochem. 2010, 74, 875-877
12. Alscher, R. G.; Erturk, N.; Heath, L. S. Role of superoxide dismutases (SODs) in controlling oxidative stress in plants J. Exp. Bot. 2002, 53, 1331-1341 (Pubitemid 34544053)
13. Raychaudhuri, S. S.; Deng, X. W. The role of superoxide dismutase in combating oxidative stress in higher plants Bot. Rev. 2000, 66, 89-98
14. Palma, L. D.; Mecozzi, R. Heavy metals mobilization from harbour sediments using EDTA and citric acid as chelating agents J. Hazard. Mater. 2007, 147, 768-775 (Pubitemid 47161106)
15. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Zhang, Z.; Beecher, G.; Holden, J.; Haytowitz, D.; Prior, R. L. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods J. Mass Spectrom. 2003, 38, 1272-1280 (Pubitemid 38072864)
16. Zhang, C. F.; Sun, Q. S.; Wang, Z. T.; Hattori, M. One new A-type proanthocyanidin trimer from Lindera aggregata (Sims) kosterm Chin. Chem. Lett. 2003, 14, 1033-1036 (Pubitemid 37378624)
17. Jacques, D.; Haslam, E. Plant proanthocyanidins. Part 112. Proanthocyanidin-A2 and its derivatives J. Chem. Soc., Perkin Trans. 1 1974, 2663-2671
18. Laks, P. E.; Hemingway, R. W.; Conner, A. H. Condensed tannins. Base-catalysed reactions of polymeric procyanidins with phloroglucinol: intramolecular rearrangements J. Chem. Soc., Perkin Trans. 1 1987, 1875-1881
19. Nonaka, G. I.; Morimoto, S.; Kinjo, J. E.; Nahara, T.; Nishioka, I. Tannins and related compounds. L. Structures of proanthocyanidin A-1 and related compounds Chem. Pharm. Bull. 1987, 35, 149-155
20. Lou, H.; Yamazaki, Y.; Sasaki, T.; Uchida, M.; Tanaka, H.; Oka, S. A-type proanthocyanidins from peanut skins Phytochemistry 1999, 51, 297-308 (Pubitemid 29246491)