TRANSFORMATION OF ETHYL-P-METHOXYCINNAMATE TO P –METHOXYCINNAMIC ACID FROM KENCUR (Kaempheria galanga L.) AND THEIR ANTIBACTERIAL ACTIVITY

Muhamad Salman Fareza, Rehana Rehana, Nuryanti Nuryanti, Didin Mujahidin

Abstract

This study aimed to evaluate the antibacterial properties of ethyl-p-methoxycinnamate and p-methoxycinnamate acid from Kaempheria galanga L. Ethyl-p-methoxycinnamate was isolated from the n-hexane rhizome extract of Kaempheria galanga L. Separation and purification of this compound was carried out with vacuum liquid chromatography and column chromatography. Hydrolysis of ethyl-p-methoxycinnamic under alkaline conditions obtained p-methoxycinnamic acid with a good yield of 85 %. The structure of the compounds were charactrized with IR, NMR spectrophotometer (1H-NMR and 13C-NMR) and mass spectrophotometer. The antibacterial properties of the compounds were evaluated using microdilution methods against B. cereus ATCC 11778, L. monocytogenes ATCC 7644, E. coli ATCC 25922, S. enterica sv Typhimurium ATCC 14028, and E. aerogenes ATCC 13048. The compounds showed weak antibacterial properties. Only ethyl p-methoxycinnamate showed the strongest antibacterial activity, especially against B. cereus ATCC 11778 bacteria with MIC values of 62.5 mg /mL. The change of the functional groups provided no significant impact on the antibacterial activity.

Keywords

antibacterial; ethy p-methoxycinnamate; kaempheria galanga L.:, p-methoxycinnamic acid.

Full Text:

PDF

References

Abdallah, E.M.,2011. Plants: An Alternative Source for Antimicrobial. Journal Applied Pharmaceutical Science 01(06), 16-20.

Alanis, A.J., 2005. Resistance to Antibiotics: Are We in The Post-antibiotic Era. Archives of Medicinal Research 36(0), 697–705. doi: 10.1016/j.arcmed.2005.06.009.

Al-zoreky, N. S. and Al-Taher, A. Y., 2015. Antibacterial Activity of Spathe from Phoenix dactylifera L. Against Some Foodborne Pathogens. Industrial crops and products 65(0), 241-246. doi: http://dx.doi.org/10.1016/j.indcrop.2014.12.014.

Arambewela, L. S. R., Perera, A., and Wijesundera, R. L. C., 1999. Antibacterial Activity of Kaempheria galanga. Fitoterapia 70(0), 425-427. doi: http://dx.doi.org/10.1016/S0367-326X(99)00053-2.

Arias, C.A. and Murray, B.E., 2015. A New Antibiotic and The Evolution of Resistance. The New England Journal of Medicine 372(12), 1168-1170. Doi: 10.1056/NEJMcibr1500292.

Badan Pengawas Obat dan Makanan RI., 2013. Dokumentasi Ramuan Etnomedisin Obat Asli Indonesia. Jakarta : BPOM RI.

Baris, O., Gulluce, M., Sahin, F., Ozer, H., Kilie, H., Ozkan, H., Sokmen, M., and Ozbek, T., 2006. Biological Activities of The Essential Oil and Methanol Extract of Achillea biebersteinii Afan. (Asterceae). Turkish Journal of Biology 30(0), 65-73.

CLSI (Clinical and Laboratory Standards Institute), 2012. Methods for Dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically: Approved Standars (9th ed.).CLSI Document M07-A9.USA: Wayne PA.

Dash, P. R., Nasrin, M., and Ali, M. S., 2014. In Vivo Cytotoxic and In Vitro Antibacterial Activities of Kaempheria galanga. Journal of Pharmacognosy and Phytochemistry 3(1), 172-177.

Davin-Regli, A. and Pages, J., 2015. Enterobacter aerogenes and Enterobacter cloaceae; Versatile Bacterial Pathogens Confronting Antibiotic Treatment. Frontiers in Microbiology 6 (392), 1-10. Doi: 10.3389/fmicb.2015.00392.

Elder, D. P., Kuents, M., and Holm, R., 2016. Antibiotic Resistance: The Need for A Global Strategy. Journal of Pharmaceutical Sciences 105(8), 2278-2287. Doi http://dx.doi.org/10.1016/j.xphs.2016.06.002.

Ekowati, J., Rudyanto, Sasaki, S., Budiati, T., Sukardiman, Hermawan, A., and Meiyanto, E., 2010. Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells. Indonesian Journal of Cancer Chemoprevention 1(1), 12-18.

Eloff, J. N., 1998. A Sensitive and Quick Microplate Method to Determine the Minimal Inhibitory Concentration of Plant Extracts for Bacteria. Planta Medica 64(8), 711-713. doi: 10.1055/s-2006-957563.

Guillemot, D., 1999. Antibiotic Use in Humans and Bacterial Resistance. Current Opinion Microbiology 2(0), 494-498. doi: 10.1016/S1369-5274(99)00006-5.

Hardman, J.G. and Limbird, L.E., 2012. Goodman and Gilman: Dasar farmakologi terapi, Edisi 10 (Terjemahan), Jakarta: EGC Penerbit Buku Kedokteran.

He, Z., Yue, G. G. , Lau, C. B., Ge, W., and But, P. P., 2012. Antiangiogenic Effects and Mechanisms of Trans-ethyl p‑methoxycinnamate from Kaempferia galanga L. Journal of Agricultural and Food Chemistry 60(0), 11309-11317. doi: dx.doi.org/10.1021/jf304169jl.

Huang, L., Yagura, T., and Chen, S., 2008. Sedative Activity of Hexane Extract of Keampferia galanga L. and Its Active Compounds. Journal of Ethnopharmacology 120(0), 123-125. doi: 10.1016/j.jep.2008.07.045.

Kerns, E.D. and Di, L., 2008. Drug-Like Properties: Concepts, Structure Design and Methods From ADME to Toxicity Optimization, UK: Elsevier.

Kochuthressia, K. P., Britto, S. J., Mo, J., and Raphael, R., 2012. In Vitro Antimicrobial Evaluation of Kaempheria galanga L. Rhizome Extract. American Journal Biotechnology and Molecular Sciences 2(1), 1-5. doi: 10.5251/ajbma.2012.2.1.1.5.

Laksmanan, D., Werngren, J., Jose, L., Suja, K. P., Nair, M. S., Varma, R. L., Mundayoor, S., and Kumar, R. A., 2011. Ethyl-p-methoxycinnamate Isolated from A Traditional Anti-tuberculosis Medicinal Herb Inhibits Drug Resistant Strains of Mycobacterium tuberculosisIn Vitro. Fitoterapia 82(0), 757-761. doi: 10.1016/j.fitote.2011.03.006.

Langfield, R. D., Scarano, F. J., Heitzman, M. E., Kondo, M., Hammond, G. B., and Neto, C. C., 2004. Use of AModified Microplate Bioassay Method to Investigate Antibacterial Activity in The Peruvian Medicinal Plant Peperomia galiodes. Journal of Ethnopharmacology 94(2-3), 279-281. doi: 10.1016/jep.2004.06.013.

Lim, T. K., 2016. Edible Medicinal and Non-medicinal Plants (Vol. 12). Switzerland: Springer.

Liu, X. C., Liang Y., Shi, W. P., Liu Q. Z., Zhou, L., and Liu, Z. L., 2014. Repellent and Insecticidal Effects of The Essential Oil of Kaempheria galangaRhizomes to Liposcelis bostrychophila (Psocoptera: Liposcelidae). Journal of Economic Entomology 107(4), 1706-1712. doi: http://dx.doi.org/10.1603/EC13491.

Mahady, G.B., 2005. Medical Plants for The Prevention and Treatment of Bacterial Infections. Current Pharmaceutical Design 11(0), 2405-2427. doi: https://doi.org/10.2174/1381612054367481.

Nakazono, Y., Watanabe, Y., Hashinaga, F., and Tadera, K., 2006. Studies on Antimicrobial and Antioxidative Substance of Yuzu (Citrus junos hort. Ex Tanaka) Seed. Journal of Biological Sciences 6(1), 135-139.

Nussbaum, F., Brands, M., HInzen, B., Weigand, S. and Habich, D., 2006. Antibacterial Natural Products in Medicinal Chemistry-Exodus or Revival. Angewandte Chemie International Edition 45(0), 5072-5129.doi:10.1002/anie.200600350.

Omar, M. N., Hasali, N. H. M., Alfarra, H. Y., Yarmo, M. A., and Zuberdi, A. M., 2014. Antimicrobial Activity and Microbial Transformation of Ethyl p-methoxycinnamate Extracted from Kaempferia galanga. Oriental Journal of Chemistry 30(3), 1037-1043. doi: http://dx.doi.org/10.13005/ojc/300315.

Pervez, M. A. K., Khan. M. M., Islam, M. Z., and Hasan, S. M., 2005. Antimicrobial Activities of The Petroleum ether, Methanol, and Acetone Extracts of Kaempheria galanga L. Rhizome. Journal of Life Earth Science 1(1), 25-29. doi:10.1.1.566.4589.

Piddock, L.J.V., 2015. Teixobactin, The First of ANew Class of Antibiotics Discovered by iChip Technology. Journal of Antimicrobial Chemotheraphy (0), 1-2. doi: https://doi.org/10.1093/jac/dkv175.

Saleem, M., Nazir, M., Ali, M. S., Hussain, H., Lee., Y. S., Riaz, N., and Jabbar, A., 2010. Antimicrobial Natural Product: An Update on Future Antibiotic Drug Candidates, Natural Product Report 27(0), 238-254. doi:10.1039/b916096e.

Sarker, S. D., Latif, Z., and Gray, A. I., 2006. Natural Products Isolation 2nd Ed. New Jersey: Humania Press.

Silverstein, R.M., Webster, F.X., and Kiemle, D.J., 2005. Spectrophotometric Identification of Organic Compound 7th Edition. USA: John Wiley and Sons.

Sirisngtragul, W. and Sripanidkulchai, B., 2011. Effects of Kaempferia galangaL. and Ethyl-p-methoxycinnamate (EPMC) on Hepatic Microsomal Cytochrome P450s Enzyme Activities in Mice. Songklanakarin Journal of Science and Technology 33(4), 411-417.

Smith-Palmer, A., Stewart, J. and Fyfe, L., 1998. Antimicrobial Properties of Plant Essential Oils and Essens Against Five Important Food-borne Pathogens. Letters in Applied Microbiology 26(0), 118-122.

Solomons, T.W.G. and Fryhle, C.B., 2011. Organic Chemistry, 10th ed.USA: John Wiley and Sons.

Syah, Y. M., 2016. Dasar-dasar Penentuan Struktur Molekul Berdasarkan Data Spektrum 1H and 13C NMR. Bandung: Laboratorium Spektroskopi Massa dan NMR ITB.

Taylor, P.W., Stapleton, P.D., and Luzio, J.P., 2002. New Ways to Threat Bacterial Infections. Drug Discovery Today 7(0), 1086-1091. doi: 10.1016/S1359-6446(02)02498-4.

Thomas, G., 2007. Medicinal chemistry: An introduction, 2nd Ed., England: John Wiley & Sons.

Threlfall, E. J., Ward, L. R., Frost, J. A., and Willshaw, G. A., 2000. The Emergence and Spread of Antibiotic Resistance in Food-borne Bacteria. International Journal of Food Microbiology 62(0), 1-5.

Umar, M. I., Asmawi, M. Z., Sadikun, A., Majid, A. M. S. A., Al-Suede, F. S. R., Hassan, L. E. A., Altaf, R., and Ahamed, M. B. K., 2014. Ethyl-p-methoxycinnamate Isolated from Kaempheria galangaInhibits Inflammation by Suppressing Interleukin-1, Tumor Necrosis Factor-α, and Angiogenesis by Blocking Endothelial Functions. CLINICS 69(2), 134-144. doi: 10.6061/clinics/2014(02)10.

DOI: https://doi.org/10.20961/alchemy.13.2.8472.176-190

Refbacks

  • There are currently no refbacks.