{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T18:52:29Z","timestamp":1772995949726,"version":"3.50.1"},"reference-count":41,"publisher":"American Society for Microbiology","issue":"2","license":[{"start":{"date-parts":[[2005,2,1]],"date-time":"2005-02-01T00:00:00Z","timestamp":1107216000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.asm.org\/non-commercial-tdm-license"}],"content-domain":{"domain":["journals.asm.org"],"crossmark-restriction":true},"short-container-title":["Antimicrob Agents Chemother"],"published-print":{"date-parts":[[2005,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>We found that ethyl gallate purified from a dried pod of tara (<jats:italic>Caesalpinia spinosa<\/jats:italic>) intensified \u03b2-lactam susceptibility in methicillin-resistant and methicillin-sensitive strains of<jats:italic>Staphylococcus aureus<\/jats:italic>(MRSA and MSSA strains, respectively). This compound and several known alkyl gallates were tested with MRSA and MSSA strains to gain new insights into their structural functions in relation to antimicrobial and \u03b2-lactam susceptibility-intensifying activities. The maximum activity of alkyl gallates against MRSA and MSSA strains occurred at 1-nonyl and 1-decyl gallate, with an MIC at which 90% of the isolates tested were inhibited of 15.6 \u03bcg\/ml. At concentrations lower than the MIC, alkyl gallates synergistically elevated the susceptibility of MRSA and MSSA strains to \u03b2-lactam antibiotics. Such a synergistic activity of the alkyl gallates appears to be specific for \u03b2-lactam antibiotics, because no significant changes were observed in the MICs of other classes of antibiotics examined in this study. The length of the alkyl chain was also associated with the modifying activity of the alkyl gallates, and the optimum length was C5 to C6. The present work clearly demonstrates that the length of the alkyl chain has a key role in the elevation of susceptibility to \u03b2-lactam antibiotics.<\/jats:p>","DOI":"10.1128\/aac.49.2.549-555.2005","type":"journal-article","created":{"date-parts":[[2005,1,26]],"date-time":"2005-01-26T22:04:40Z","timestamp":1106777080000},"page":"549-555","update-policy":"https:\/\/doi.org\/10.1128\/asmj-crossmark-policy-page","source":"Crossref","is-referenced-by-count":70,"title":["Alkyl Gallates, Intensifiers of \u03b2-Lactam Susceptibility in Methicillin-Resistant<i>Staphylococcus aureus<\/i>"],"prefix":"10.1128","volume":"49","author":[{"given":"Hirofumi","family":"Shibata","sequence":"first","affiliation":[{"name":"Department of Molecular Cell Biology and Medicine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kyoko","family":"Kondo","sequence":"additional","affiliation":[{"name":"Department of Natural Medicines"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryo","family":"Katsuyama","sequence":"additional","affiliation":[{"name":"Department of Molecular Cell Biology and Medicine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuyoshi","family":"Kawazoe","sequence":"additional","affiliation":[{"name":"Department of Natural Medicines"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoichi","family":"Sato","sequence":"additional","affiliation":[{"name":"Department of Human Genetics and Public Health, Institute of Health Biosciences, The University of Tokushima, Shomachi, Tokushima, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kotaro","family":"Murakami","sequence":"additional","affiliation":[{"name":"Department of Natural Medicines"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshihisa","family":"Takaishi","sequence":"additional","affiliation":[{"name":"Department of Natural Medicines"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naokatu","family":"Arakaki","sequence":"additional","affiliation":[{"name":"Department of Molecular Cell Biology and Medicine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tomihiko","family":"Higuti","sequence":"additional","affiliation":[{"name":"Department of Molecular Cell Biology and Medicine"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"235","reference":[{"key":"e_1_3_1_2_2","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/0005-2736(94)00293-X","volume":"1234","year":"1995","unstructured":"Aranda, F. J., J. Villalain, and J. C. Gomez-Fernandez. 1995. Capsaicin affects the structure and phase organization of phospholipid membranes. Biochim. Biophys. Acta1234:225-234.","journal-title":"Biochim. Biophys. Acta"},{"key":"e_1_3_1_3_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.27.4.632"},{"key":"e_1_3_1_4_2","doi-asserted-by":"publisher","DOI":"10.1067\/mic.2001.119952"},{"key":"e_1_3_1_5_2","first-page":"565","volume":"51","year":"2002","unstructured":"Centers for Disease Control and Prevention. 2002. Staphylococcus aureus resistant to vancomycin\u2014United States, 2002. Morb. Mortal. Wkly. Rep.51:565-567.","journal-title":"Morb. Mortal. Wkly. Rep."},{"key":"e_1_3_1_6_2","first-page":"902","volume":"51","year":"2002","unstructured":"Centers for Disease Control and Prevention. 2002. Vancomycin-resistant Staphylococcus aureus\u2014Pennsylvania, 2002. Morb. Mortal. Wkly. Rep.51:902.","journal-title":"Morb. Mortal. Wkly. Rep."},{"key":"e_1_3_1_7_2","first-page":"322","volume":"53","year":"2004","unstructured":"Centers for Disease Control and Prevention. 2004. Vancomycin-resistant Staphylococcus aureus\u2014New York, 2004. Morb. Mortal. Wkly. Rep.53:322-323.","journal-title":"Morb. Mortal. Wkly. Rep."},{"key":"e_1_3_1_8_2","doi-asserted-by":"publisher","DOI":"10.1097\/01.md.0000091185.93122.40"},{"key":"e_1_3_1_9_2","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMoa025025"},{"key":"e_1_3_1_10_2","doi-asserted-by":"publisher","DOI":"10.1128\/CMR.12.4.564"},{"key":"e_1_3_1_11_2","doi-asserted-by":"crossref","first-page":"283","DOI":"10.7164\/antibiotics.50.283","volume":"50","year":"1997","unstructured":"Eid, C. N., N. G. Halligan, T. I. Nicas, D. L. Mullen, T. F. Butler, R. J. Loncharich. J. W. Paschal, C. J. Schofield, N. J. Westwood, and L. Cheng. 1997. Tripeptide LY301621 and its diastereomers as methicillin potentiators against methicillin resistant Staphylococcus aureus. J. Antibiot.50:283-285.","journal-title":"J. Antibiot."},{"key":"e_1_3_1_12_2","unstructured":"Food and Agriculture Organization of the United Nations. 1995. Gums resins and latexes of plant origin. Non-wood forest products 6. Food and Agriculture Organization of the United Nations. [Online.] http:\/\/www.fao.org\/docrep\/v9236e\/V9236e00.htm . Accessed 17 May 2004."},{"key":"e_1_3_1_13_2","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1248\/bpb.22.463","volume":"22","year":"1999","unstructured":"Fukuda, N., T. Yamase, and Y. Tajima. 1999. Inhibitory effect of polyoxotungstates on the production of penicillin-binding proteins and \u03b2-lactamase against methicillin-resistant Staphylococcus aureus. Biol. Pharm. Bull.22:463-470.","journal-title":"Biol. Pharm. Bull."},{"key":"e_1_3_1_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0367-326X(02)00082-5"},{"key":"e_1_3_1_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(00)04376-2"},{"key":"e_1_3_1_16_2","doi-asserted-by":"publisher","DOI":"10.1086\/383146"},{"key":"e_1_3_1_17_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.46.2.558-560.2002"},{"key":"e_1_3_1_18_2","unstructured":"Isenberg H. D. 1992. Clinical microbiology procedures handbook vol. 1. American Society for Microbiology Washington D.C."},{"key":"e_1_3_1_19_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1995.tb07939.x"},{"key":"e_1_3_1_20_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.41.11.2355"},{"key":"e_1_3_1_21_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/34.6.885"},{"key":"e_1_3_1_22_2","unstructured":"Phytomed. 2004"},{"key":"e_1_3_1_23_2","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/S0960-894X(01)00663-1","volume":"12","year":"2002","unstructured":"Kubo, I., P. Xiao, and K. Fujita. 2002. Anti-MRSA activity of alkyl gallates. Bioorg. Med. Chem. Lett.12:113-116.","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"e_1_3_1_24_2","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1211\/0022357001773922","volume":"52","year":"2000","unstructured":"Liu, I. X., D. G. Durham, and R. M. Richards. 2000. Baicalin synergy with \u03b2-lactam antibiotics against methicillin-resistant Staphylococcus aureus and other \u03b2-lactam-resistant strains of S. aureus. J. Pharm. Pharmacol.52:361-366.","journal-title":"J. Pharm. Pharmacol."},{"key":"e_1_3_1_25_2","doi-asserted-by":"publisher","DOI":"10.1056\/NEJM199808203390806"},{"key":"e_1_3_1_26_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1999.tb08733.x"},{"key":"e_1_3_1_27_2","unstructured":"J. Nat. Products 2004"},{"key":"e_1_3_1_28_2","first-page":"463","year":"2000","unstructured":"Projan, S. J. 2000. Antibiotic resistance in the staphylococci, p. 463-470. In V. A. Fischetti, R. P. Novick, J. J. Ferretti, D. A. Portnoy, and J. I. Rood (ed.), Gram-positive pathogens. American Society for Microbiology, Washington, D.C.","journal-title":"Gram-positive pathogens"},{"key":"e_1_3_1_29_2","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1248\/bpb.20.401","volume":"20","year":"1997","unstructured":"Sato, Y., H. Oketani, K. Singyouchi, T. Ohtsubo, M. Kihara, H. Shibata, and T. Higuti. 1997. Extraction and purification of effective antimicrobial constituents of Terminalia chebula RETS against methicillin-resistant Staphylococcus aureus. Biol. Pharm. Bull.20:401-404.","journal-title":"Biol. Pharm. Bull."},{"key":"e_1_3_1_30_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.48.4.1357-1360.2004"},{"key":"e_1_3_1_31_2","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.ijantimicag.2004.02.001","volume":"24","year":"2004","unstructured":"Sato, Y., H. Shibata, T. Arai, A. Yamamoto, Y. Okimura, N. Arakaki, and T. Higuti. 2004. Variation in synergistic activity by flavone and its related compounds on the increased susceptibility of various strains of methicillin-resistant Staphylococcus aureus to \u03b2-lactam antibiotics. Int. J. Antimicrob. Agents24:28-35.","journal-title":"Int. J. Antimicrob. Agents"},{"key":"e_1_3_1_32_2","doi-asserted-by":"crossref","first-page":"1478","DOI":"10.1248\/bpb.26.1478","volume":"26","year":"2003","unstructured":"Shibata, H., C. Shirakata, H. Kawasaki, Y. Sato, T. Kuwahara, Y. Ohnishi, N. Arakaki, and T. Higuti. 2003. Flavone markedly affects phenotypic expression of \u03b2-lactam resistance in methicillin-resistant Staphylococcus aureus strains isolated clinically. Biol. Pharm. Bull.26:1478-1483.","journal-title":"Biol. Pharm. Bull."},{"key":"e_1_3_1_33_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.45.11.3198-3201.2001"},{"key":"e_1_3_1_34_2","doi-asserted-by":"crossref","first-page":"1388","DOI":"10.1248\/bpb.22.1388","volume":"22","year":"1999","unstructured":"Shiota, S., M. Shimizu, T. Mizushima, H. Ito, T. Hatano, T. Yoshida, and T. Tsuchiya. 1999. Marked reduction in the minimum inhibitory concentration (MIC) of \u03b2-lactams in methicillin-resistant Staphylococcus aureus produced by epicatechin gallate, an ingredient of green tea (Camellia sinensis). Biol. Pharm. Bull.22:1388-1390.","journal-title":"Biol. Pharm. Bull."},{"key":"e_1_3_1_35_2","first-page":"135","volume":"185","year":"2000","unstructured":"Shiota, S., M. Shimizu, T. Mizusima, H. Ito, T. Hatano, T. Yoshida, and T. Tsuchiya. 2000. Restoration of effectiveness of \u03b2-lactams on methicillin-resistant Staphylococcus aureus by tellimagrandin I from rose red. FEMS Microbiol. Lett.185:135-138.","journal-title":"FEMS Microbiol. Lett."},{"key":"e_1_3_1_36_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.42.5.1278"},{"key":"e_1_3_1_37_2","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1111\/j.1574-6968.1997.tb12592.x","volume":"153","year":"1997","unstructured":"Suzuki, J., H. Komatsuzawa, M. Sugai, K. Ohta, K. Kozai, N. Nagasaka, and H. Suginaka. 1997. Effects of various types of Triton X on the susceptibilities of methicillin-resistant staphylococci to oxacillin. FEMS Microbiol. Lett.153:327-331.","journal-title":"FEMS Microbiol. Lett."},{"key":"e_1_3_1_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(01)05410-1"},{"key":"e_1_3_1_39_2","doi-asserted-by":"crossref","first-page":"1067","DOI":"10.1016\/0278-6915(86)90290-5","volume":"24","year":"1986","unstructured":"Van der Heijden, C. A., P. J. Janssen, and J. J. Strik. 1986. Toxicology of gallates: a review and evaluation. Food Chem. Toxicol.24:1067-1070.","journal-title":"Food Chem. Toxicol."},{"key":"e_1_3_1_40_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkg104"},{"key":"e_1_3_1_41_2","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1248\/bpb.19.459","volume":"19","year":"1996","unstructured":"Yamase, T., N. Fukuda, and Y. Tajima. 1996. Synergistic effect of polyoxotungstates in combination with \u03b2-lactam antibiotics on antibacterial activity against methicillin-resistant Staphylococcus aureus. Biol. Pharm. Bull.19:459-465.","journal-title":"Biol. Pharm. Bull."},{"key":"e_1_3_1_42_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.45.6.1737-1742.2001"}],"container-title":["Antimicrobial Agents and Chemotherapy"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/journals.asm.org\/doi\/pdf\/10.1128\/AAC.49.2.549-555.2005","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.asm.org\/doi\/pdf\/10.1128\/AAC.49.2.549-555.2005","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,12,22]],"date-time":"2024-12-22T21:03:46Z","timestamp":1734901426000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.asm.org\/doi\/10.1128\/AAC.49.2.549-555.2005"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,2]]},"references-count":41,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2005,2]]}},"alternative-id":["10.1128\/AAC.49.2.549-555.2005"],"URL":"https:\/\/doi.org\/10.1128\/aac.49.2.549-555.2005","relation":{},"ISSN":["0066-4804","1098-6596"],"issn-type":[{"value":"0066-4804","type":"print"},{"value":"1098-6596","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,2]]},"assertion":[{"value":"2004-06-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2004-10-25","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2005-02-01","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}