Polyphenolic constituent structures of Zanthoxylum piperitum fruit and the antibacterial effects of its polymeric procyanidin on methicillin-resistant Staphylococcus aureus

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 6, 2006, Pages 1423-1431

  Kusuda, Miwako ^a   Inada, Kazutoshi ^a   Ogawa, Tomo Omi ^a   Yoshida, Takashi ^a,c   Shiota, Sumiko ^b   Tsuchiya, Tomofusa ^a   Hatano, Tsutomu ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b SHUJITSU UNIVERSITY   (Japan)

^c MATSUYAMA UNIVERSITY   (Japan)

Author keywords

Antibiotic resistance; Methicillin resistant Staphylococcus aureus (MRSA); Polymeric proanthocyanidin; Polyphenol; Zanthoxylum piperitum

Indexed keywords

ANTIBIOTICS; CELL MEMBRANES; DEGRADATION; ENZYMES; NATURAL POLYMERS; PLANTS (BOTANY); PURIFICATION;

ANTIBIOTIC RESISTANCE; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS (MRSA); POLYMERIC PROANTHOCYANIDIN; POLYPHENOL; ZANTHOXYLUM PIPERITUM;

ORGANIC COMPOUNDS;

ANTIINFECTIVE AGENT; BETA LACTAMASE; BIFLAVONOID; CATECHIN; FLAVONOID; OXACILLIN; PHENOL DERIVATIVE; POLYPHENOLS; PROANTHOCYANIDIN; PROCYANIDIN; THIOL DERIVATIVE; ZP CT A COMPOUND; ZP-CT-A COMPOUND;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DRUG ANTAGONISM; DRUG EFFECT; FRUIT; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OSMOLARITY; PENICILLIN RESISTANCE; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; ZANTHOXYLUM;

ANTI-BACTERIAL AGENTS; BETA-LACTAMASES; BIFLAVONOIDS; CATECHIN; CELL PROLIFERATION; FLAVONOIDS; FRUIT; MAGNETIC RESONANCE SPECTROSCOPY; METHICILLIN RESISTANCE; MOLECULAR STRUCTURE; OSMOLAR CONCENTRATION; OXACILLIN; PHENOLS; PROANTHOCYANIDINS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; ZANTHOXYLUM;

BACTERIA (MICROORGANISMS); METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; RUTACEAE; ZANTHOXYLUM; ZANTHOXYLUM PIPERITUM;

EID: 33745487548     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.50669     Document Type: Article

References (32)

1. Iinuma, M., Tosa, H., Tanaka, T., Asai, F., Kobayashi, Y., Shimano, R., and Miyauchi, K., Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus. J. Pharm. Pharmacol., 48, 861-865 (1996).
2. Hatano, T., Uebayashi, H., Ito, H., Shiota, S., Tsuchiya, T., and Yoshida, T., Phenolic constituents of cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem. Pharm. Bull., 47, 1121-1127 (1999).
3. Shiota, S., Shimizu, M., Mizusima, T., Ito, H., Hatano, T., Yoshida, T., and Tsuchiya, T., Restoration of effectiveness of β-lactams on methicillin-resistant Staphylococcus aureus by tellimagrandin I from rose red. FEMS Microbiol. Lett., 185, 135-138 (2000).
4. Hatano, T., Shintani, Y., Aga, Y., Shiota, S., Tsuchiya, T., and Yoshida, T., Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. Chem. Pharm. Bull., 48, 1286-1292 (2000).
5. Shimizu, M., Shiota, S., Mizushima, T., Ito, H., Hatano, T., Yoshida, T., and Tsuchiya, T., Marked potentiation of activity of β-lactams against methicillin-resistant Staphylococcus aureus by corilagin. Antimicrob. Agents Chemother., 45, 3198-3201 (2001).
6. Shiota, S., Shimizu, M., Sugiyama, J., Morita, Y., Mizushima, T., and Tsuchiya, T., Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of β-lactams against methicillin-resistant Staphylococcus aureus. Microbiol. Immunol., 48, 67-73 (2004).
7. Stapleton, P. D., Shah, S., Anderson, J. C., Hara, Y., Hamilton-Miller, J. M., and Taylor, P. W., Modulation of β-lactam resistance in Staphylococcus aureus by catechins and gallates. Int. J. Antimicrob. Agents, 23, 462-467 (2004).
8. Fujita, M., Shiota, S., Kuroda, T., Hatano, T., Yoshida, T., Mizushima, T., and Tsuchiya, T., Remarkable synergies between baicalein and tetracycline, and baicalein and β-lactams against methicillin-resistant Staphylococcus aureus. Microbiol. Immunol., 49, 391-396 (2005).
9. Hatano, T., Kusuda, M., Hori, M., Shiota, S., Tsuchiya, T., and Yoshida, T., Theasinensin A, a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant Staphylococcus aureus. Planta Med., 69, 984-989 (2003).
10. Hatano, T., Inada, K., Ogawa, T., Ito, H., and Yoshida, T., Aliphatic acid amides of the fruits of Zanthoxylum piperitum. Phytochemistry, 65, 2599-2604 (2004).
11. Hatano, T., Miyatake, H., Natsume, M., Osakabe, N., Takizawa, T., Ito, H., and Yoshida, T., Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects. Phytochemistry, 59, 749-758 (2002).
12. Novic, R. P., Analysis by transduction of mutations affecting penicillinase formation in Staphylococcus aureus. J. Gen. Microbiol., 33, 121-136 (1963).
13. Nakatani, N., Kayano, S., Kikuzaki, H., Sumino, K., Katagiri, K., and Mitani, T., Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in Prune (Prunus domestica L.). J. Agric. Food Chem., 48, 5512-5516 (2000).
14. Foo, L. Y., Newman, R., Waghorn, G., McNabb, W. C., and Ulyatt, M. J., Proanthocyanidins from Lotus corniculatus. Phytochemistry, 41, 617-624 (1996).
15. Hatano, T., and Hemingway, R. W., Conformational isomerism of phenolic procyanidins: preferred conformations in organic solvents and water. J. Chem. Soc., Perkin Trans. 1, 1035-1043 (1997).
16. Aritomi, M., Chemical studies on the constituents of edible plants (Part 2). J. Home Econ. Jpn., 34, 233-236 (1983).
17. Bae, Y. S., Foo, L. Y., and Karchesy, J. J., GPC of natural procyanidin oligomers and polymers. Holzforschung, 48, 4-6 (1994).
18. Laks, P. E., Flavonoid biocides: phytoalexin analogues from condensed tannins. Phytochemistry, 26, 1617-1621 (1987).
19. O'Callaghan, C. H., Morris, A., Kirby, S. M., and Shingler, A. H., Novel method for detection of β-lactamase by using a chromogenic cephalosporin substrate. Antimicrob. Agents Chemother., 1, 283-288 (1972).
20. Czochanska, Z., Foo, L. Y., Newman, R. H., and Porter, L. J., Polymeric proanthocyanidins: stereochemistry, structural units, and molecular weight. J. Chem. Soc., Perkin Trans. 1, 2278-2286 (1980).
21. Zhao, W. H., Hu, Z. Q., Okubo, S., Hara, Y., and Shimamura, T., Mechanism of synergy between epigallocatechin gallate and β-lactams against methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother., 45, 1737-1742 (2001).
22. Sato, Y., Shibata, H., Arai, T., Yamamoto, A., Okimura, Y., Arakai, N., and Higuti, T., Variation in synergistic activity by flavone and its related compounds on the increased susceptibility of various strains of methicillin-resistant Staphylococcus aureus to β-lactam antibiotics. Int. J. Antimicrob. Agents, 24, 28-35 (2004).
23. Ikigai, H., Nakae, T., Hara, Y., and Shimamura, T., Bactericidal catechins damage the lipid bilayer. Biochim. Biophys. Acta, 1147, 132-136 (1993).
24. Caturla, N., Vera-Samper, E., Villalai'n, J., Mateo, R., and Micol, V., The relationship between the antioxidant and the antibacterial properties of galloylated and the structure of phospholipids model membranes. Free Radic. Biol. Med., 34, 648-662 (2003).
25. Kubo, I., Fujita, K., Nihei, K., and Masuoka, N., Nonantibiotic antibacterial activity of dodecyl gallate. Bioorg. Med. Chem., 11, 573-580 (2003).
26. Stapleton, P. D., Shah, S., Hamilton-Miller, J. M. T., Hara, Y., Nagaoka, Y., Kumagai, A., Uesato, S., and Taylor, P. W., Anti-Staphylococcus aureus activity and oxacillin resistance modulating capacity of 3-O-acylcatechins. Int. J. Antimicrob. Agents, 24, 374-380 (2004).
27. Kajiya, K., Hojo, H., Suzuki, M., Nanjo, F., Kumazawa, S., and Nakayama, T., Relationship between antibacterial activity of (+)-catechin derivatives and their interaction with a model membrane. J. Agric. Food Chem., 52, 1514-1519 (2004).
28. Guyot, S., Doco, T., Souquet, J. M., Moutounet, M., and Drilleau, J. F., Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var. kermerrien) skin and pulp. Phytochemistry, 44, 351-357 (1997).
29. De Freitas, V. A. P., Glories, Y., and Laguerre, M., Incidence of molecular structure in oxidation of grape seed procyanidins. J. Agric. Food Chem., 46, 376-382 (1998).
30. Natume, M., Osakabe, N., Yamaguchi, M., Takizawa, T., Nakamura, T., Miyatake, H., Hatano, T., and Yoshida, T., Analyses of polyphenols in cacao liquor, cocoa, and chocolate by normal-phase and reversed-phase HPLC. Biosci. Biotechnol. Biochem., 64, 2581-2587 (2000).
31. Shoji, T., Mutsuga, M., Nakamura, T., Kanda, T., Akiyama, H., and Goda, Y., Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. J. Agric. Food Chem., 51, 3806-3813 (2003).
32. Taylor, A. W., Barofsky, E., Kennedy, J. A., and Deinzer, M. L., Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography. J. Agric. Food Chem., 51, 4101-4110 (2003).