DOI QR코드

DOI QR Code

Antimicrobial Activity of Oleanolic Acid for Foodborne Bacteria

식중독 세균에 대한 Oleanolic Acid의 항균활성

  • Choi, Kyoung-Hee (Department of Oral Microbiology, College of Dentistry, Wonkwang University) ;
  • Kim, Sejeong (Department of Food and Nutrition, Sookmyung Women's University) ;
  • Yoon, Yohan (Department of Food and Nutrition, Sookmyung Women's University)
  • 최경희 (원광대학교 치의예과) ;
  • 김세정 (숙명여자대학교 식품영양학과) ;
  • 윤요한 (숙명여자대학교 식품영양학과)
  • Received : 2014.06.17
  • Accepted : 2015.01.02
  • Published : 2015.03.30

Abstract

Oleanolic acid and its derivatives are pentacyclic triterpene acids, which are produced in many plants and herbs. These are considered safe and thus, oleanolic acid is now used for cosmetic and pharmaceutical industry. Oleanolic acid affects peptidoglycan in cell wall of bacteria. Hence, the antimicrobial activity of oleanolic acid is not very obvious to Gram-negative bacteria such as Escherichia coli, Yersinia enterocolitica, Shigella flexneri, and Shigella sonnei because the peptidoglycan is covered with outer membrane. However, oleanolic acid derivatives showed improved antimicrobial activity to Gram-negative bacteria. For Gram-positive bacteria such as Staphylococcus aureus and Listeria monocytogenes, oleanolic acid was very effective on reducing the cell counts of the pathogens. In addition, the cytotoxicity of oleanolic acid for human cell lines was minimal. Therefore, oleanolic acid should be considered as an antimicrobial food additive and a therapeutic agent to control foodborne pathogens.

Oleanolic acid는 다수의 식물 종에서 분리 되어 왔고 주로 유해한 영향이 없는 과일과 약초에 존재하기 때문에 전세계적으로 많은 나라에서 안전하게 소비되고 있으며, 현재는 화장품이나 약품에 사용되고 있다. Oleanolic acid는 peptidoglycan을 표적으로 하기 때문에 petidoglycan이 세균외막에 덮여있는 그람음성세균인 E. coli, Y. enterocolitica, S. flexneri, S. sonnei와 같은 세균에는 뚜렷한 oleanolic acid 항균활성이 관찰되지 않았다. 하지만 oleanolic acid의 유도체를 사용할 경우 그람음성세균에 대한 항균활성도 증가하였다. 반면 S. aureus와 L. monocytogenes와 같은 그람양성세균의 경우 peptidoglycan층이 세균외막에 덮여 있지 않기 때문에 oleanolic acid에 매우 민감하였다. 또한 oleanolic acid는 사람에 대한 세포독성 실험에서도 그 독성이 낮은 것으로 판단되었기 때문에 식중독 세균제어를 목적으로 연구를 진행할 필요가 있으며, 이 결과들은 식품에 적용되거나 항생제 대체를 위한 치료목적으로도 사용될 수 있을 것으로 사료된다.

Keywords

References

  1. Fontanay, S., Grare, M., Mayer, J., Finance, C. and Duval, R.E.: Ursolic, oleanolic and betulinic acids: antibacterial spectra and selectivity indexes. J. Ethnopharmacol. 120, 272-276 (2008). https://doi.org/10.1016/j.jep.2008.09.001
  2. Yoon, Y. and Choi, K.H.: Antimicrobial activities of therateutic herbal plants against Listeria monocytogenes and the herbal plant cytotoxicity on Caco-2 cell. Lett. Appl. Microbiol. 55, 47-55 (2012). https://doi.org/10.1111/j.1472-765X.2012.03262.x
  3. Liu, J.: Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 49, 57-68 (1995). https://doi.org/10.1016/0378-8741(95)90032-2
  4. Becker, H., Scher, J.M., Speakman, J.B. and Zapp, J.: Bioactivity guided isolation of antimicrobial compounds from Lythrum salicaria. Fitoterapia. 76, 580-584 (2005). https://doi.org/10.1016/j.fitote.2005.04.011
  5. Djoukeng, J.D., Abou-Mansour, E., Tabacchi, R., Tapondjou, A.L., Bouda, H. and Lontsi, D.: Antibacterial triterpenes from Syzygium guineense (Myrtaceae). J. Ethnopharmacol. 101, 283-286 (2005). https://doi.org/10.1016/j.jep.2005.05.008
  6. Kuete, B., Wabo, G.F., Ngameni, B., Mbaveng, A.T., Metuno, R., Etoa, F.X., Ngadjui, B.T., Beng, V.P., Meyer, J.J. and Lall, N.: Antimicrobial activity of the methanolic extract, fractions and compounds from the stem bark of Irvingia gabonensis (Ixonanthaceae). J. Ethnopharmacol. 114, 54-60 (2007). https://doi.org/10.1016/j.jep.2007.07.025
  7. Kuete, V., Eyong, K.O., Folefoc, G.N., Beng, V.P., Hussain, H., Krohn, K. and Nkengfack, A.E.: Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. Pharmazie. 62, 552-556 (2007).
  8. Cowan, M.M.: Plant products as antimicrobial agents. Clin. Microbiol. Rev. 12, 564-82 (1999).
  9. Kontogianni, V.G., Exarchou, V., Troganis, A. and Gerothanassis, I.P.: Rapid and novel discrimination and quantification of oleanolic and ursolic acids in complex plant extracts using two-dimensional nuclear magnetic resonance spectroscopy-Comparison with HPLC methods. Anal. Chim. Acta. 635, 188-195 (2009). https://doi.org/10.1016/j.aca.2009.01.021
  10. Liu, J., Liu, Y.P. and Klaassen, C.D.: Protective effect of oleanolic acid against chemical-induced acute necrotic liver-injury in mice. Acta Pharm. Sin. 16, 97-102 (1995).
  11. Hung, C.Y. and Yen, G.C.: Extraction and identification of antioxidative components of Hsian-tsao (Mesona procumbens Hemsl.). Food Sci. Technol. 34, 306-311 (2001).
  12. Yin, M.C. and Chan, K.C.: Nonenzymatic antioxidative and antiglycative effects of oleanolic acid and ursolic acid. J. Agric. Food Chem. 55, 7177-7181 (2007). https://doi.org/10.1021/jf071242m
  13. Kinjo, J., Okawa, M., Udayama, M., Sohno, Y., Hirakawa, T., Shii, Y. and Nohara, T. Hepatoprotective and hepatotoxic actions of oleanolic acid-type triterpenoidal glucuronoids on rat primary hepatocyte cultures. Chem. Pharm. Bull. 47, 290-292 (1999). https://doi.org/10.1248/cpb.47.290
  14. Dharmappa, K.K., Cumar, R.V., Nataraju, A., Mohanmed, R., Shivaprasad, H.V. and Vishwanath, B.S.: Anti-inflammatory activity of oleanolic acid by inhibition of secretory phospholipase A2. Planta Med. 75, 211-215 (2009). https://doi.org/10.1055/s-0028-1088374
  15. Rodriguez, J.A., Astudillo, L. and Schmeda-Hirschmann, G.: Oleanolic acid promotes healing of acetic acid-induced chronic gastric lesions in rats. Pharm. Res. 48, 291-294 (2003). https://doi.org/10.1016/S1043-6618(03)00155-5
  16. Chiang, L.C., Chiang, W., Chang, M.Y., Ng, L.T. and Lin, C.C.: Antileukemic activity of selected natural products in Taiwan. Am. J. Chin. Med. 31, 37-46 (2003). https://doi.org/10.1142/S0192415X03000825
  17. Farina, C., Pinz, M. and Pifferi, G.: Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acids. Farmaco. 53, 22-32 (1998). https://doi.org/10.1016/S0014-827X(97)00013-X
  18. Ma, B.L. Hypolipidemic effects of oleanolic acid. Trad. Med. Pharmacol. 2, 28-29 (1982).
  19. Gbaguidi, F., Accrombessi, G., Moudachirou, M. and Quetin-Leclercq, J.: HPLC quantification of two isomeric triterpenic acids isolated from Mitracarpus scaber and antimicrobial activity on Dermatophilus congolensis. J. Pharmaceut. Biomed. 39, 990-995 (2005). https://doi.org/10.1016/j.jpba.2005.05.030
  20. Resende, F.A., Andrade Barcala, C.A.M., Silva Faria, M.C., Kato, F.H., Cunha, W.R. and Tavares, C.: Antimutagenicity of ursolic acid and oleanolic acid against doxorubicin-induced clastogenesis in Balb/c mice. Life Sci. 79, 1268-1273 (2006). https://doi.org/10.1016/j.lfs.2006.03.038
  21. Capel, C.S., Souza, A.C.D., Carvalho, T.C., Sousa, J.P.B., Ambrosio, S.R., Martins, C.H.G., Cunha, W.R., Galan, R.H. and Furtado, N.A.J.C.: Biotransformation using Mucor rouxii for the production of oleanolic acid derivatives and their antimicrobial activity against oral pathogens. J. Ind. Microbiol. Biotechnol. 38, 1493-1498 (2011). https://doi.org/10.1007/s10295-010-0935-y
  22. Fai, Y.M. and Tao, C.C.: A review of presence of oleanolic acid in natural products. Nat. Proda Med. 2, 77-290 (2009).
  23. Fukushima, E.O., Seki, H., Ohyama, K., One, E., Umemoto, N., Mizutani, M., Saito, K. and Muranaka, T.: CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis. Plant Cell Physiol. 52, 2050-2061 (2011). https://doi.org/10.1093/pcp/pcr146
  24. Cai, L. and Wu, C. D.: Compounds from Syzygium aromaticum processing growth inhibitory activity against oral pathogens. J. Nat. Prod. 59, 987-990 (1996) https://doi.org/10.1021/np960451q
  25. Somova, L.I., Shode, F.O., Ramnanan, P. and Nadar, A. Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea ueropaea, subspecies africana leaves. J. Ethnopharmacol. 84, 299-305 (2003). https://doi.org/10.1016/S0378-8741(02)00332-X
  26. Somova, L.I., Shode, F.O. and Mipando, M.: Cardiotonic and antidysrhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvaol. Phytomedicine. 11, 121-129 (2004). https://doi.org/10.1078/0944-7113-00329
  27. Sanchez-Avila, N., Priego-Capote, F., Ruiz-Jimenez, J., de Castro, M.D.: Fast and selective determination of triterpenic compounds in olive leaves by liquid chromatography-tandem mass spectrometry with multiple reaction monitoring after microwave-assisted extraction. Talanta. 79, 40-48 (2009).
  28. Abe, F., Yamauchi, T., Nagao, T., Kinjo, J., Okabe, H., Higo, H. and Akahane, H.: Ursolic acid as a trypanocidal constituent in rosemary. Biol. Pharm. Bull. 25, 1485-1487 (2002). https://doi.org/10.1248/bpb.25.1485
  29. Sultana, N. and Ata, A.: Oleanolic acid and related derivatives as medicinally important compounds. J. Enzym. Inhib. & Med. Chem. 23, 739-756 (2008). https://doi.org/10.1080/14756360701633187
  30. Razborsek, M.I., Voncina, D.B., Dolecek, V. and Voncina, E.: Determination of oleanolic, betulinic and ursolic acid in Lamiaceae and mass spectal fragmentation of their trimethylsilylated derivatives. Chromatographia. 67, 433-440 (2008). https://doi.org/10.1365/s10337-008-0533-6
  31. Kozai, K., Suzuki, J., Okada, M. and Nagasaka, N.: Effect of oleanolic-acid-cyclodextrin inclusion compounds on carries by in vitro experiment and rat-carries model. Microbios. 97,179-188 (1999).
  32. Horiuchi, K., Shiota, S., Hatano, T., Yoshida, T., Kuroda, T. and Tsuchiya, T.: Antibacterial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycin-resistant enterococci. Biol. Pharm. Bull. 30, 1147-1149 (2007). https://doi.org/10.1248/bpb.30.1147
  33. Jimenez-Arellanes, A., Meckes, M., Torres, J.K. and Luna, H.J.: Antimycobacterial triterpenoids from Lantana hispida (Verbenaceae). J. Ethnopharmacol. 111, 202-205 (2007). https://doi.org/10.1016/j.jep.2006.11.033
  34. Szakiel, A., Ruszkowski, D., Grudniak, A., Kurek, A., Wolsk, K.I., Doligalska, M. and Janiszowska, W.: Antibacterial and antiparasitic activity of oleanolic acid and its glycosides isolated from marigold (Calendula officinalis). Planta Med. 74, 1709-1715 (2008). https://doi.org/10.1055/s-0028-1088315
  35. Hichri, F., Jannet, H.B., Cheriaa, J., Jegham, S. and Mighri, Z.: Antibacterial activities of a few prepared derivatives of oleanolic acid and of other natural triterpenic compounds. C.R.Chimie. 6, 473-483 (2003). https://doi.org/10.1016/S1631-0748(03)00066-3
  36. Rivero-Cruz, J.F., Zhu, M., Kinghor, A.D. and Wu, C.D.: Antimicrobial constituents of Thompson seedless raisins (Vitis vinifera) against selected oral pathogens. Phytochem. Lett. 1, 151-154 (2008). https://doi.org/10.1016/j.phytol.2008.07.007
  37. Ren D., Zuo R., Gonzles Barrios A. F., Bedzyk L. A., Eldbridge G. R., Pasmore M. E. and Wood T. K.: Differential gene expression for investigation of Escherichia coli biofilm inhibition by plant extract ursolic acid. Appl. Environment. Microbiol. 71, 4022-4034 (2005). https://doi.org/10.1128/AEM.71.7.4022-4034.2005
  38. Yoon, Y. and Choi, K.H.: Antimicrobial activity of oleanolic acid on Listeria monocytogenes under sublethal stresses of NaCl and pH. Korean J. Food Sci. Ani. Resour. 30, 717-721 (2010). https://doi.org/10.5851/kosfa.2010.30.5.717
  39. Woldemichael G.M., Singh M.P., Maiese, W.M. and Timmermann, B.N.: Constituents of antibacterial extract of Caesalpinia paraguariensis Burk. Z. Naturforsch. 58C, 70-75 (2003).
  40. Wang, X., Ye, X., Chen, H.L., Bai, H., Liang, X., Zhang, X.D., Wang, Z., Li, W. and Hai, C.X.: Antioxidant activities of oleanolic acid in vitro: Possible role of Nrf2 and MAP kinases. Chem-Biol. Interact. 184, 328-337 (2010). https://doi.org/10.1016/j.cbi.2010.01.034
  41. Ovesna, Z., Vachalkova, A., Horvathova, K. and Tothova, D.: Pentacyclic triterpenoic acids: new chemoprotective compounds. Neoplasma. 51, 327-333 (2004).
  42. Grudniak, A.M., Kurek, A., szarlak, J. and Wolska, K.I. Oleanolic and ursolic acids influence affect the expression of the cysteine regulon and the stress response in Escherichia coli. Curr. Microbiol. 62,1331-1336 (2011). https://doi.org/10.1007/s00284-010-9866-0
  43. Kurek, A., Grudniak, A.M., Szwed, M., Klicka, A., Samluk, L., Wolska, K.I., Janiszowska, W. and Popowska, M.: Oleanolic acid and ursolic acid affect peptidoglycan metabolism in Listeria monocytogenes. Anton Leeuw. 97, 61-68 (2010). https://doi.org/10.1007/s10482-009-9388-6

Cited by

  1. vol.55, pp.1, 2017, https://doi.org/10.1080/13880209.2017.1279673