Antibacterial Curcuma xanthorrhiza Extract and Fractions

Hartiwi Diastuti, Yana M. Syah, Lia D. Juliawaty, Marlia Singgih

Abstract


An acetone extract of Curcuma xanthorrhiza rhizomes and the n-hexane and chloroform fractions obtained from it were tested on eight pathogenic bacteria. The results showed that the acetone extract and the nhexane fraction exhibited significant activities against Bacillus subtilis, Pseudomonas aeruginosa, and Staphylococcus aureus, and weak activities against Shigella dysenteriae and Vibrio cholerae. They were inactive against Escherichia coli, Enterobacter aerogenes and Salmonella thypi, while the chloroform fraction was devoid of activities. NMR analysis disclosed the presence of α-curcumene, xanthorrhizol and an unknown monoterpene in the nhexane fraction. In the chloroform fraction, curcumin was found to be the main compound, together with xanthorrhizol as a minor compound. These results suggest that the antibacterial potency of acetone extract of C. xanthorrhiza is contained in the n-hexane fraction, in which the active constituents are terpenoid compounds. This is the first report of the use of NMR analysis for compound identification contained in an extract or fractions of C. xanthorrhiza.

Keywords


α-curcumene; antibacterial; Curcuma xanthorrhiza; curcumin; xanthorrhizol; NMR analysis; TOCSY-1D

Full Text:

PDF

References


Saleem, M., Nazir, M., Ali, M.S., Hussain, H., Lee, Y.S., Riaza, N. & Jabbar, A., Antimicrobial Natural Products: An Update on Future Antibiotic Drug Candidates, Nat. Prod. Rep., 27, pp. 238-254, 2010.

Abreu, A.C., McBainb, A.J. & Simoes, M., Plants as Sources of New Antimicrobials and Resistance-Modifying Agents, Nat. Prod. Rep., 29, pp. 1007-1021, 2012.

Sjamsul, S.A., Hakim, E.H., Makmur, L., Syah, Y.M., Juliawaty, L.D. & Mujahidin, M., Chemistry and Uses of Indonesian Plant Drugs, Vol. I, ITB Publisher, pp. 143-152, 2007, (text in Indonesian)

Rimpler, H., Hansel, R. & Kochendoefer, L., Xanthorrhizol, a New Sesquiterpene from Curcuma xanthorrhiza, Z. Naturforsch. B., 25B, pp. 995-998, 1970.

Itokawa, H., Hirayama, F., Funakoshi, K. & Takeya, K., Studies on the Antitumor Bisabolane Sesquiterpenoids Isolated from Curcuma xanthorrhiza, Chem. Pharm. Bull, 33, pp. 3488-3492, 1985.

Yamazaki, M., Maebayashi, Y., Iwase, N. & Kaneko, .T., Studies on Pharmacologically Active Principles From Indonesian Crude Drugs. II. Hypothermic Principle from Curcuma xanthorrhiza Roxb, Chem. Pharm. Bull, 36, pp. 3488-3492, 1988.

Uehara, S., Yasuda, I., Takeya, K., Itokawa, H. & Iitaka, Y., New Bisabolane Sesquiterpenoids from the Rhizomes of Curcuma xanthorrhiza (Zingiberaceae), Chem. Pharm. Bull, 38, 261-263, 1990.

Uehara, S., Yasuda, I., Takeya, K. & Itokawa, H., Terpenoids and Curcuminoids of the Rhizoma of Curcuma xanthorrhiza Roxb, Yakugaku Zasshi, 112, pp. 817-823, 1992.

Claeson, P., Panthong, A., Tuchinda, P., Reutrakul, V., Kanjanapothi, D., Taylor, W.C. & Santisuk, T., Three Non-Phenolic Diarylheptanoids with Anti-Inflammatory Activity from Curcuma xanthorrhiza, Planta Med., 59, pp. 451-454, 1993.

Suksamrarn, A., Eiamong, S., Piyachaturawat, P. & Charoenpiboonsin, J., Phenolic diarylheptanoids from Curcuma xanthorrhiza, Phytochemistry, 36, 1505-1508, 1994.

Surh, Y.-J., Chun, K.-S., Cha, H.-H., Han, S.S., Keum, Y.,-S., Park, K.-K. & Lee, S.S., Molecular Mechanisms Underlying Chemopreventive Activities of Anti-inflammatory Phytochemicals: Down-Regulation of COX-2 and iNOS through Suppression of NF-B Activation, Mutation Res., 480-481, pp. 243-268, 2001.

Miquel, J., Bernd, A., Sempere, J.M., Díaz-Alperi, J. & Ramírez, A., The Curcuma Antioxidants: Pharmacological Effects and Prospects for Future Clinical Use. A Review, Arch. Gerontol. Geriatr., 34, pp. 37-46, 2002.

Maheshwari, R.K., Singh, A.K., Gaddipati, J. & Srimal R.C., Multiple Biological Activities of Curcumin: A Short Review, Life Sci., 78, pp. 2081-2087, 2006.

Mary Helen, P.A., Susheela, G.K., Jayasree, S., Nizzy, A.M., Rajagopal, B. & Jeeva, S., Phytochemical Characterization and Antimicrobial Activity of Curcuma xanthorrhiza Roxb., Asian Pac. J. Trop. Biomed., S637-S640, 2012.

Rukayadi, Y., Han, S., Yong, D. & Hwang, J.-K., In Vitro Activity of Xanthorrhizol against Candida glabrata, C. guilliermondii, and C. parapsilosis Biofilms, Med. Mycol., 49, pp. 1-9, 2010.

Rukayadi, Y., Lee, K., Lee, M.-S., Yong, D. & Hwang, J.-K., Synergistic Anticandidal Activity of Xanthorrhizol in Combination with Ketoconazole or Amphotericin B, FEMS Yeast Res., 9, pp. 1302-1311, 2009.

Yanti, Rukayadi, Y., Lee, K., Han, S. & Hwang, J.-K., Anti-biofilm Activity of Xanthorrhizol Isolated from Curcuma xanthorrhiza Roxb. Against Bacterial Biofilms Formed by Saliva and Artificial Multi-Species Oral Strains, Food Sci. Biotechnol., 18, pp. 556-560, 2009.

Lee, Y.L., Shim, J.-S., Rukayadi, Y. & Hwang, J.-K., Antibacterial Activity of Xanthorrhizol Isolated from Curcuma xanthorrhiza Roxb. against Foodborne Pathogens, J. Food Protect., 71, pp. 1926-1930, 2008.

Demain, A.L. & Sanchez, S., Microbial Drug Discovery: 80 Years of Progress, J. Antibiotics, 62, pp. 5-16, 2009.

Yasni, S., Imaizumi, K., Sin, K., Sugano, M., Nonaka, G. & Sidik, Identification of an Active Principle in Essential Oils and Hexane-Soluble Fractions of Curcuma xanthorrhiza Roxb. Showing Triglyceride- Lowering Action in Rats, Food Chem. Toxic., 32, pp. 273-278, 1994.

Devaraj, S., Ismail, S., Ramanathan, S., Marimuthu, S. & Fei, Y.M., Evaluation of the Hepatoprotective Activity of Standardized Ethanolic Extract of Curcuma xanthorrhiza Roxb, J. Med. Plants Res., 4, pp. 2512-2517, 2010.

Devaraj, S., Esfahani, A.S., Ismail, S., Ramanathan, S. & Yam, M.F., Evaluation of the Antinociceptive Activity and Acute Oral Toxicity of Standardized Ethanolic Extract of the Rhizome of Curcuma xanthorrhiza Roxb., Molecules, 15, pp. 2925-2934, 2010.

Sukandar, E.Y., Nurdewi & Elfahmi, Antihypercholesterolemic Effect of Combination of Guazuma ulmifolia Lamk. Leaves and Curcuma xanthorrhiza Roxb. Rhizomes Extract in Wistar Rats, Int. J. Pharm., 8, pp.277-282, 2012.

Jae, H.P., Kwang, K.P., Mi, J.K., Jae, K.H., Sun, K.P. & Won, Y.C., Cancer Chemoprotective Effects of Curcuma xanthorrhiza, Phytotherapy Res., 22, 695-698, 2008.

Kim, H.S., Choi, C.H., Kwon, H.K. & Kim, B.I., Combined Inhibitory Effect of Curcuma xanthorrhiza extract and Xylitol on Streptococcus mutons and Actinomyces viscosus, Key Eng. Mat., 342-343, pp. 861-864, 2007.

Kim, J.-E., Kim, H.-E., Hwang, J.-K., Lee, H.-J., Kwon, H.-K. & Kim, B.-I., Antibacterial Characteristics of Curcuma xanthorrhiza Extract on Streptococcus mutons Biofilm, J. Microbiol., 46, pp. 228-232, 2008.

Itokawa, H., Hirayama, F., Funakoshi, K., Takeya, K., Studies on the Antitumor Bisabolane Sesquiterpenoids Isolated from Curcuma xanthorrhiza, Chem. Pharm. Bull., 33, pp. 3488-3492, 1985.

Choi, M.-A., Kim, S.H., Chung, W.-Y., Hwang, J.-K. & Park, K.-K., Xanthorrhizol, a Natural Sesquiterpenoid from Curcuma xanthorrhiza, has an Anti-Metastatic Potential in Experimental Mouse Lung Metastasis Model, Biochem. Biophys. Res. Commun., 326, pp. 210-217, 2004.

Ismail, N., Lope Pihie, A.H. & Nallapan, M., Xanthorrhizol Induces Apoptosis via the Up-regulation of Bax and p53 in HeLa cells, Anticancer Res., 25(3B), pp. 2221-2227, 2005.

Cheah, Y.H., Azimahtol, H.L.P. & Abdullah, N.R., Xanthorrhizol Exhibits Antiproliferative Activity on MCF-7 Breast Cancer Cells via Apoptosis Induction, Anticancer Res., 26(6B), pp. 4527-4534, 2006.

Handayani, T., Sakinah, S., Nallappan, M. & Pihie, A.H.L., Regulation of p53-, Bcl-2- and Caspase-Dependent Signaling Pathway in Xanthorrhizol-Induced Apoptosis of HepG2 Hepatoma Cells, Anticancer Res., 27, pp. 965-971, 2007.

Yew, H.C., Nordin, F.J., Thiam, T.T., Azimahtol, H.L.P., Abdullah, N.R. & Ismail, Z., Antiproliferative Property and Apoptotic Effect of Xanthorrhizol on MDA-MB-231 Breast Cancer Cells, Anticancer Rese., 28(6 A), pp. 3677-3689, 2008.

Cheah, Y.H., Nordin, F.J., Sarip, R., Tee, T.T., Azimahtol, H.L.P., Sirat, H.M., Rashid, B.A.A., Abdullah, N.R. & Ismail, Z., Combined Xanthorrhizol-Curcumin Exhibits Synergistic Growth Inhibitory Activity via Apoptosis Induction in Human Breast Cancer Cells MDA-MB-231, Cancer Cell Internat., 9, art. no. 1, 2009.

Kang, Y.-J., Park, K.-K., Chung, W.-Y., Hwang, J.-K. & Lee, S.K., Xanthorrhizol, a Natural Sesquiterpenoid, Induces Apoptosis and Growth Arrest in HCT116 Human Colon Cancer Cells, J. Pharm. Sci., 111, pp. 276-284, 2009.




DOI: http://dx.doi.org/10.5614%2Fj.math.fund.sci.2014.46.3.2

Refbacks

  • There are currently no refbacks.


View my Stats

Creative Commons License
This work is licensed under a Creative Commons Attribution-NoDerivatives 4.0 International License.

 

ITB Journal Publisher, LPPM ITB, Center for Research and Community Services (CRCS) Building, 6th & 7th Floor, Jalan Ganesha 10, Bandung 40132, Indonesia, Phone: +62-22-86010080, Fax.: +62-22-86010051; E-mail: jmfs@lppm.itb.ac.id