Polyphenolic constituents of cynomorium songaricum Rupr. and antibacterial effect of polymeric proanthocyanidin on methicillin-resistant staphylococcus aureus

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 29, 2012, Pages 7297-7305

  Jin, Shangwu ^a,b   Eerdunbayaer, ^b   Doi, Airi ^b   Kuroda, Teruo ^b   Zhang, Guixia ^a   Hatano, Tsutomu ^b   Chen, Guilin ^a  

^a INNER MONGOLIA UNIVERSITY   (China)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

antibacterial effect; Cynomorium songaricum Rupr.; methicillin resistant Staphylococcus aureus, phloroglucinol adducts; Proanthocyanidin

Indexed keywords

ACID-CATALYZED DEGRADATION; ANTI-BACTERIAL ACTIVITY; ANTIBACTERIAL EFFECTS; CHEMICAL DATA; CHROMATOGRAPHIC FRACTIONATION; CYNOMORIUM SONGARICUM RUPR; EPICATECHIN; EXTENSION UNITS; FLAVAN-3-OLS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; PHLOROGLUCINOL; POLYMERIC CONSTITUENTS; POLYMERIZATION DEGREE; PROANTHOCYANIDINS; PROCYANIDINS; TERMINAL UNITS;

ACETONE; BACTERIA; CHROMATOGRAPHIC ANALYSIS; OLIGOMERS; ORGANIC COMPOUNDS; PHENOLS; POLYMERIZATION; SIZE EXCLUSION CHROMATOGRAPHY; SPECTRUM ANALYSIS;

POLYMERS;

ANTIINFECTIVE AGENT; CATECHIN; FLAVONOID; PHLOROGLUCINOL; PLANT EXTRACT; POLYPHENOL; PROANTHOCYANIDIN;

ARTICLE; CHEMISTRY; CYNOMORIUM; DRUG EFFECT; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; PLANT STEM;

ANTI-BACTERIAL AGENTS; CATECHIN; CYNOMORIUM; FLAVONOIDS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; PHLOROGLUCINOL; PLANT EXTRACTS; PLANT STEMS; POLYPHENOLS; PROANTHOCYANIDINS;

CYNOMORIUM SONGARICUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS;

EID: 84864346800     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301621e     Document Type: Article

References (26)

1. Mayer, R.; Stecher, G.; Wuerzner, R.; Silva, R. C.; Sultana, T.; Trojer, L.; Feuerstein, I.; Krieg, C.; Abel, G.; Popp, M.; Bobleter, O.; Bonn, G. K. Proanthocyanidins: Target compounds as antibacterial agents J. Agric. Food Chem. 2008, 56, 6959-6966
2. Stapleton, P. D.; Shah, S.; Anderson, J. C.; Hara, Y.; Hamilton-Miller, J. M. T.; Taylor, P. W. Modulation of β-lactam resistance in Staphylococcus aureus by catechins and gallates Int. J. Antimicrob. Agents 2004, 23, 462-467
3. Hatano, T.; Kusuda, M.; Hori, M.; Shiota, S.; Tsuchiya, T.; Yoshida, T. Theasinensin A, a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant Staphylococcus aureus Planta Med. 2003, 69, 984-989
4. Hatano, T.; Hori, M.; Kusuda, M.; Ohyabu, T.; Ito, H.; Yoshida, T. Characterization of the oxidation products of (-)-epigallocatechin gallate, a bioactive tea polyphenol, on incubation in neutral solution Heterocycles 2004, 63, 1547-1554
5. Kusuda, M.; Inada, K.; Ogawa, T. O.; Yoshida, T.; Shiota, S.; Tsuchiya, T.; Hatano, T. Polyphenolic constituent structures of Zanthoxylum piperitum fruit and the antibacterial effects of its polymeric procyanidin on methicillin-resistant Staphylococcus aureus Biosci., Biotechnol., Biochem. 2006, 70, 1423-1431
6. Ma, L. J.; Chen, G. L.; Jin, S. W.; Wang, C. X. The anti-aging effect and the chemical consttuents of Cynomorium songaricum Rupr Acta Hortic. 2006, 765, 23-30
7. Ma, C. M.; Sato, N.; Li, X. Y.; Nakamura, N.; Hattori, M. Flavan-3-ol contents, anti-oxidative and α-glucosidase inhibitory activities of Cynomorium songaricu m Food Chem. 2010, 118, 116-119
8. Ma, C. M.; Nakamura, N.; Miyashiro, H.; Hattori, M.; Shimotohno, K. Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-1 protease Chem. Pharm. Bull. 1999, 47, 141-145
9. Kimura, Y.; Ito, H.; Kawaji, M.; Ikami, T.; Hatano, T. Characterization and antioxidative properties of oligomeric proanthocyanidin from prunes, dried fruit of Prunus domestica L Biosci., Biotechnol., Biochem. 2008, 72, 1615-1618
10. Shiota, S.; Shimizu, M.; Mizushima, T.; Ito, H.; Hatano, T.; Yoshida, T.; Tsuchiya, T. Marked reduction in the minimum inhibitory concentration (MIC) of beta-lactams in methicillin-resistant Staphylococcus aureus produced by epicatechin gallate, an ingredient of green tea (Camellia sinensis) Biol. Pharm. Bull. 1999, 22, 1388-1390
11. Hatano, T.; Hemingway, R. W. Conformational isomerism of phenolic procyanidins: Preferred conformations in organic solvents and water J. Chem. Soc. Perkin Trans 2 1997, 1035-1043
12. Sang, S. M.; Cheng, X. F.; Stark, R. E.; Rosen, R. T.; Yang, C. S.; Ho, C. T. Chemical studies on antioxidant mechanism of tea catechins: analysis of radical reaction products of catechin and epicatechin with 2,2-diphenyl-1- picrylhydrazyl Bioorg. Med. Chem. 2002, 10, 2233-2237
13. Saito, A.; Doi, Y.; Tanaka, A.; Matsuura, N.; Ubukata, M.; Nakajima, N. Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity Bioorg. Med. Chem. 2004, 12, 4783-4790
14. Shoji, T.; Mutsuga, M.; Nakamura, T.; Kanda, T.; Akiyama, H.; Goda, Y. Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance J. Agric. Food Chem. 2003, 51, 3806-3813
15. Saito, A.; Mizushina, Y.; Tanaka, A.; Nakajima, N. Versatile synthesis of epicatechin series procyanidin oligomers, and their antioxidant and DNA polymerase inhibitory activity Tetrahedron 2009, 65, 7422-7428
16. Czochanska, Z.; Foo, L. Y.; Newman, R. H.; Porter, L. J. Polymeric proanthocyanidins: Stereochemistry, structural units, and molecular weight J. Chem. Soc. Perkin Trans. 1 1980, 2278-2286
17. Hemingway, R. W.; McGraw, G. W. Kinetics of acid-catalyzed cleavage of procyanidins J. Wood Chem. Technol. 1983, 3, 421-425
18. Kennedy, J. A.; Jones, G. P. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol J. Agric. Food Chem. 2001, 49, 1740-1746
19. Kennedy, J. A.; Taylor, A. W. Analysis of Proanthocyanidins by High-Performance Gel Permeation Chromatography J. Chromatogr., A 2003, 995, 99-107
20. Taniguchi, S.; Kuroda, K.; Yoshikado, N.; Doi, K.; Tanabe, M.; Shibata, T.; Yoshida, T.; Hatano, T. New dimeric flavans from gambir, an extract of Uncaria gambir Heterocycles 2007, 74, 595-605
21. Taniguchi, S.; Kuroda, K.; Doi, K.; Tanabe, M.; Shibata, T.; Yoshida, T.; Hatano, T. Revised structures of gambirins A1, A2, B1, and B2, chalcane-flavan dimers from gambir (Uncaria gambir extract) Chem. Pharm. Bull. 2007, 55, 268-272
22. Nonaka, G.; Nishika, I. Novel Biflavonoids, chlcan-flavan dimmers from gambir Chem. Pharm. Bull. 1980, 28, 3145-3149
23. Hatano, T.; Kusuda, M.; Inada, K.; Ogawa, T.; Shita, S.; Tsuchiya, T.; Yoshida, T. Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus Phytochemistry 2005, 66, 2047-2055
24. Prieur, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Oligomeric and polymeric procyanidins from grape seeds Phytochemistry 1994, 36, 781-784
25. Foo, L. Y.; Lu, Y. R. Isolation and identification of procyanidins in apple pomace Food Chem. 1999, 64, 511-518
26. Gu, L. W.; House, S. E.; Wu, X. L.; Ou, B. X.; Prior, R. L. Procyanidin and catechin contents and antioxidant capacity of cocoa and chocolate products J. Agric. Food Chem. 2006, 54, 4057-4061