The relationship between structure and in vitro antibacterial activity of selected isoflavones and their metabolites with special focus on antistaphylococcal effect of demethyltexasin

Letters in Applied Microbiology

Volumn 60, Issue 3, 2015, Pages 242-247

  Hummelova, J ^a   Rondevaldova, J ^a   Balastikova, A ^a   Lapcik, O ^b   Kokoska, L ^a  

^a CZECH UNIVERSITY OF LIFE SCIENCES PRAGUE   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Antimicrobial activity; Demethyltexasin; Isoflavonoids; Methicillin resistant Staphylococcus aureus; Minimum inhibitory concentration

Indexed keywords

BACTERIA; BIOMOLECULES; C (PROGRAMMING LANGUAGE); FLAVONOIDS; MICROWAVE INTEGRATED CIRCUITS;

ANTI-BACTERIAL ACTIVITY; ANTI-MICROBIAL ACTIVITY; DEMETHYLTEXASIN; GENISTEIN; ISOFLAVONES; ISOFLAVONOIDS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIPS;

METABOLITES;

5,4' DIHYDROXY 7 METHOXYISOFLAVONE; 5,7,4' TRIMETHOXYISOFLAVONE; 6,4' DIMETHOXY 7 HYDROXYISOFLAVONE; 6,7,4' TRIMETHOXYISOFLAVONE; 7 HYDROXY 6 METHOXYISOFLAVONE; 7,4' DIHYDROXY 6 METHOXYISOFLAVONE; 7,4' DIHYDROXYISOFLAVONE; 7,4' DIMETHOXY 5 HYDROXYISOFLAVONE; 7,4' DIMETHOXYISOFLAVONE; ANTIBIOTIC AGENT; BIOCHANIN A; CYCLOOXYGENASE 2; DAIDZEIN; DEMETHYLRETUSIN; DEMETHYLTEXASIN; DRUG METABOLITE; FORMONONETIN; GENISTEIN; HYDROXYDAIDZEIN; ISOFLAVONE DERIVATIVE; METICILLIN; UNCLASSIFIED DRUG; 6,7,4'-TRIHYDROXYISOFLAVONE; 7,8,4'-TRIHYDROXYISOFLAVONE; ANTIINFECTIVE AGENT; PLANT EXTRACT;

CONCENTRATION (COMPOSITION); FUNCTIONAL GROUP; GROWTH RATE; METABOLITE; MICROBIAL ACTIVITY;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIOXIDANT ACTIVITY; ARTICLE; BACILLUS CEREUS; BACTERIAL GROWTH; BACTERIAL STRAIN; BROTH DILUTION; CELL TRANSFORMATION; CHEMICAL STRUCTURE; CHLAMYDIA; CLOSTRIDIA; DRUG IDENTIFICATION; DRUG POTENCY; DRUG STRUCTURE; ENTEROCOCCUS FAECALIS; GROWTH REGULATION; IN VITRO STUDY; LISTERIA MONOCYTOGENES; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHICILLIN SUSCEPTIBLE STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM; NONHUMAN; SOYBEAN; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION; CHEMISTRY; DRUG EFFECTS; GRAM NEGATIVE BACTERIUM; HUMAN; MICROBIAL SENSITIVITY TEST;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; GENISTEIN; GRAM-NEGATIVE BACTERIA; HUMANS; ISOFLAVONES; METHICILLIN; MICROBIAL SENSITIVITY TESTS; PLANT EXTRACTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84923108722     PISSN: 02668254     EISSN: 1472765X     Source Type: Journal    
DOI: 10.1111/lam.12361     Document Type: Article

References (29)

1. Chacha, M., Bojase-Moleta, G. and Majinda, R.R.T. (2005) Antimicrobial and radical scavenging flavonoids from the stem wood of Erythrina latissimi. Phytochemistry 66, 99-104.
2. Clinical and Laboratory Standards Institute (CLSI) (2009) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, 8th edn. Approved Standard M07-A8. Wayne, PA: Clinical and Laboratory Standards Institute (CLSI).
3. Cos, P., Vlietinck, A.J., Berghe, D.V. and Maes, L. (2006) Anti-infective potential of natural products: how to develop a stronger in vitro 'proof-of-concept'. J Ethnopharmacol 106, 290-302.
4. Cushnie, T.P.T. and Lamb, A.J. (2005) Antimicrobial activity of flavonoids. Int J Antimicrob Agents 26, 343-356.
5. Dastidar, S.G., Manna, A., Kumar, K.A., Mazumdar, K., Dutta, N.K., Chakrabarty, A.N., Motohashi, N. and Shirataki, Y. (2004) Studies on the antibacterial potentiality of isoflavones. Int J Antimicrob Agents 23, 99-102.
6. Hanski, L., Genina, N., Skogman, M., Parkkisenniemi-Kinnunen, U.-M., Mäkilä, E., Salonen, J., Fallarero, A., Sandler, N. et al. (2012) Anti-C pneumonia activity and sublingual formulation of biochanin A. II International Conference on Antimicrobial Research, Lisbon, Portugal: Book of Abstracts, 151.
7. Havsteen, B. (1983) Flavonoids, a class of natural products of high pharmacological potency. Biochem Pharmacol 32, 1141-1148.
8. Iinuma, M., Tsuchiya, H., Sato, M., Yokoyama, J., Ohyama, M., Ohkawa, Y., Tanaka, T., Fujiwara, S. et al. (1994) Flavanones with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. J Pharm Pharmacol 46, 892-895.
9. Kuete, V., Ngameni, B., Simo, C.C.F., Tankeu, R.K., Ngadjui, B.T., Meyer, J.J.M., Lall, N. and Kuiate, J.R. (2008) Antimicrobial activity of the crude extracts and compounds from Ficus chlamydocarpa and Ficus cordata (Moraceae). J Ethnopharmacol 120, 17-24.
10. Kulling, S.E., Honig, D.M. and Metzler, M. (2001) Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J Agric Food Chem 49, 3024-3033.
11. Lechner, D., Gibbons, S. and Bucar, F. (2008) Plant phenolic compounds as ethidium bromide efflux inhibitors in Mycobacterium smegmatis. J Antimicrob Chemother 62, 345-348.
12. Lee, D.E., Lee, K.W., Byun, S., Jung, S.K., Song, N., Lim, S.H., Heo, Y.-S., Kim, J.E. et al. (2011a) 7, 3′, 4′-trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J Biol Chem 286, 14246-14256.
13. Lee, D.E., Lee, K.W., Jung, S.K., Lee, E.J., Hwang, J.A., Lim, T.-G., Kim, B.Y., Bode, A. et al. (2011b) 6, 7, 4′-trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2. Carcinogenesis 32, 629-635.
14. Liu, R.X., Sun, J.H., Bi, K.S. and Guo, D.A. (2005) Identification and determination of major flavonoids in rat serum by HPLC-UV and HPLC-MS methods following oral administration of Dalbergia odorifera extract. J Chromatogr B Analyt Technol Biomed Life Sci 829, 35-44.
15. Mukne, A.P., Viswanathan, V. and Phadatare, A.G. (2011) Structure-activity relationships of isoflavones with antibacterial activity. Pharmacogn Rev 5, 13-18.
16. Pandey, K.B. and Rizvi, S.I. (2009) Plant polyphenols as dietary antioxidants in human health and disease. Oxid Med Cell Longev 2, 270-278.
17. Pantosti, A., Sanchini, A. and Monaco, M. (2007) Mechanisms of antibiotic resistance in Staphylococcus aureus. Future Microbiol 2, 323-334.
18. Pohjala, L., Uvell, H., Hakala, E., Gylfe, A., Elofsson, M. and Vuorela, P. (2012) The isoflavone biochanin A inhibits the growth of the intracellular bacteria Chlamydia trachomatis and Chlamydia pneumonia. Planta Med 78, 1102.
19. Roh, C., Jung, U. and Jo, S.K. (2011) 6, 7, 4 '-trihydroxyisoflavone from Doenjang inhibits lipid accumulation. Food Chem 129, 183-187.
20. Rowland, I., Faughnan, M., Hoey, L., Wahala, K., Williamson, G. and Cassidy, A. (2003) Bioavailability of phyto-oestrogens. Brit J Nutr 89, S45-S58.
21. Sato, M., Tanaka, H., Yamaguchi, R., Kato, K. and Etoh, H. (2004) Synergistic effects of mupirocin and an isoflavanone isolated from Erythrina variegata on growth and recovery of methicillin-resistant Staphylococcus aureus. Int J Antimicrob Agents 24, 241-246.
22. Sato, M., Tanaka, H., Tani, N., Nagayama, M. and Yamaguchi, R. (2006) Different antibacterial actions of isoflavones isolated from Erythrina poeppigiana against methicillin-resistant Staphylococcus aureus. Lett Appl Microbiol 43, 243-248.
23. Sklenickova, O., Flesar, J., Kokoska, L., Vlkova, E., Halamova, K. and Malik, J. (2010) Selective growth inhibitory effect of biochanin A against intestinal tract colonizing bacteria. Molecules 15, 1270-1279.
24. Tanaka, H., Sato, M., Fujiwara, S., Hirata, M., Etoh, H. and Takeuchi, H. (2002) Antibacterial activity of isoflavonoids isolated from Erythrina variegata against methicillin-resistant Staphylococcus aureus. Lett Appl Microbiol 35, 494-498.
25. Timan, P., Rojanasthien, N., Manorot, M., Sangdee, C. and Teekachunhatean, S. (2014) Effect of synbiotic fermented milk on oral bioavailability of isoflavones in postmenopausal women. Int J Food Sci Nutr 65, 761-767.
26. Verdrengh, M., Collins, L.V., Bergin, P. and Tarkowski, A. (2004) Phytoestrogen genistein as an anti-staphylococcal agent. Microbes Infect 6, 86-92.
27. Villares, A., Rostagno, M.A., García-Lafuente, A., Guillamón, E. and Martínez, J.A. (2011) Content and profile of isoflavones in soy-based foods as a function of the production process. Food Bioprocess Technol 4, 27-38.
28. Wyman, J.G. and VanEtten, H.D. (1978) Antibacterial activity of selected isoflavonoids. Phytopathology 68, 583-589.
29. Xu, H.X. and Lee, S.F. (2001) Activity of plant flavonoids against antibiotic-resistant bacteria. Phytother Res 15, 39-43.