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The Pharmaceutical Society of Korea (대한약학회)
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Antimycobacterial Activity and Cytotoxicity of Flavonoids from the Flowers of Chromolaena odorata

  • Suksamrarn, Apichart (Department of Chemistry, Faculty of Science, Ramkhamhaeng University) ;
  • Chotipong, Apinya (Department of Chemistry, Faculty of Science, Ramkhamhaeng University) ;
  • Suavansri, Tananit (Department of Chemistry, Faculty of Science, Ramkhamhaeng University) ;
  • Boongird, Somnuk (Department of Agricultural Science, Faculty of Science, Ramkhamhaeng University) ;
  • Timsuksai, Puntip (Department of Chemistry, Faculty of Science and Technology, Rajabhat Institute Nakhonratchasi) ;
  • Vimuttipong, Saovaluk (National Center for Genetic Engineering and Biotechology, National Science and Technology, Development Agenc) ;
  • Chuaynugul, Aporn (Department of Chemistry, Faulty of Science, Ramkhamhaeng University)
  • Published : 2004.05.01
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Abstract

From the flowers of Chromolaena odorata (Eupatorium odoratum) four flavanones, isosakuranetin (5,7-dihydroxy-4'-methoxyflavanone) (1), persicogenin (5,3'-dihydroxy-7,4'-dimethoxyflavanone) (2), 5,6,7,4'-tetramethoxyflavanone (3) and 4'-hydroxy-5,6,7-trimethoxyfla-vanone (4), two chalcones, 2'-hydroxy-4,4',5',6'-tetramethoxychalcone (5) and 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (6), and two flavones, acacetin (5,7-dihydroxy-4'-methoxyflavone) (7) and luteolin (5,7,3',4'-tetrahydroxyflavone) (8) were isolated and identified. Compound 1 exhibited moderate antimycobacterial activity against Mycobacterium tuberculosis with the MIC value of 174.8 $\mu$M, whereas compounds 4,7, and 8 exhibited weak activity with the MIC values of 606.0, 704.2 and 699.3 $\mu$M respectively. Compound 7 showed moderate cytotoxicity against human small cell lung cancer (NCI-H187) cells with the MIC value of 24.6 $\mu$M, whereas compound 8 exhibited moderate toxicity against NCI-H187 cells and week toxicity against human breast cancer (BC) cells with the MIC values of 19.2 and 38.4 $\mu$M respectively.

Keywords

References

  1. Ahmad, M. and Nabi, M. N., Chemical investigations on the leaves of Eupatorium odoratum. Sci. Res. Dacca, Pakistan, 4, 154-157 (1967)
  2. Arene, E. O., Pettit, G. R., and Ode, R. H., LAntineoplastic agents. Part 49. The isolation of isosakuranetin methyl ether from Eupatorium odoratum. loydia, 41, 186-189 (1978)
  3. Bamba, D., Bessiere, J. M., Marion, L., Pelissier, Y., and Fouraste, I., Essential oil of Eupatorium odoratum. Planta Medh., 59, 184-185 (1993) https://doi.org/10.1055/s-2006-959642
  4. Barua, R. N., Sharma, R. P., Thyagarajan, G., and Hertz, W., Flavonoids of Chromolaena odorata. Phytochemistry, 17, 1807-1808 (1978) https://doi.org/10.1016/S0031-9422(00)88710-5
  5. Baruah, R. N. and Leclercq, P. A., Constituents of the essential oil from the flowers of Chromolaena odorata. Planta Med., 59, 283 (1993) https://doi.org/10.1055/s-2006-959674
  6. Baruah, R. N. and Pathak, M. G., Fatty acid compositions of Chromolaena odorata flower fat. Ind. J. Nat. Prod., 9, 17-18 (1993)
  7. Biller, A., Boppre, M., Witte, L., and Hartmann, T., Pyrrolizidine alkaloids in Chromolaena odorata. Chemical and chemoecological aspects. Phytochemistry, 35, 615-619 (1994) https://doi.org/10.1016/S0031-9422(00)90573-9
  8. Bose, P. K., Chakrabarti, P., Chakravarti, S., Dutta, S. P., and Barua, A. K., Chemical examination of the leaves of Eupatorium odoratum. Trans. Bose Res. Inst. (Calcutta), 37, 25-30 (1974)
  9. Bose, B. K., Chakrabarti, P., Chakravarti, S., Dutta, S. P., and Barua, A. K., Flavonoid constituents of Eupatorium odoratum. Phytochemistry, 12, 667-668 (1973) https://doi.org/10.1016/S0031-9422(00)84461-1
  10. Bunyapraphatsara, N. and Chokechaijaroenporn, O., Thai Medicinal Plants, Vol. 4. Faculty of Pharmacy, Mahidol University and National Center for Genetic Engineering and Biotechnology, Bangkok, pp. 622-626, (2000)
  11. Chowdhury, A. R., Essential oils of the leaves of Eupatorium odoratum L. from Shillong (N. E.). J. Essen. Oil-Bearing Plants, 5, 14-18 (2002)
  12. Collins, L. A. and Franzblau, S. G., Microplate Alamar Blue Assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother., 41, 1004-1009 (1997)
  13. Gonzalez, A. G., Fraga , B. M., Hernandez, M. G., and Garcia, V. P., Eupatorone, a 2-acetylbenzofuran from Eupatorium sternburgianum. Phytochemistry, 21, 1826-1827 (1982)
  14. Hai, M. A., Biswas, P. K., Shil, K. C., and Ahmad, M. U., Chemical constituents of Eupatorium odoratum Linn. (Compositae). J. Bangladesh Chem. Soc., 4, 47-49 (1991)
  15. Hai, M. A., Saha, K., and Ahmad, M. U., Chemical constituents of Eupatorium odoratum Linn. (Compositae). J. Bangladesh Chem. Soc., 8, 139-142 (1995)
  16. Inya-Agha, S. I., Oguntimein , B. O., Sofowora, A., and Benjamin, T. V., Phytochemical and antibacterial studies on the essential oil of Eupatorium odoratum. Int. J. Crude Drug Res., 25, 49-52 (1987)
  17. Iwu, M. M., Handbook of African medicinal plants. CRC Press, Ann Arbor, pp. 181-182, (1993)
  18. Lamaty, G., Menut, C., Zollo, P. H. A., Kuiate, J. R., Bessiere, J. M., Quamba, J. M., and Silou, T., Aromatic plants of tropical Central Africa, IV. Essential oil of Eupatorium odoratum L. from Cameroon and Congo. J. Essen. Oil Res., 4, 101-105 (1992) https://doi.org/10.1080/10412905.1992.9698028
  19. Mabry, T. J., Markham, K. R., and Thomas, M. B., The systematic identification of flavonoids. Springer, New York, (1970)
  20. Metwally, A. M. and Ekejiuba, E. C., Methoxylated flavonols and flavanones from Eupatorium odoratum. Planta Med., 42, 403-405 (1981) https://doi.org/10.1055/s-2007-971663
  21. Muniappan, R. and Marutani, M., Distribution and control of Chromolaena odorata (Asteraceae). Micronesica, Suppl. 3, 103-107 (1991)
  22. Pollock, J. R. A. and Stevens, R. (Eds.). Dictionary of Organic Compounds, Vol. 4. Oxford University Press, New York, p. 2030, (1965)
  23. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82,1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  24. Talapatra, S. K., Bhar, D. S, and Talapatra, B., Flavonoid and terpenoid constituents of Eupatotium odoratum. Phytochemistry, 13, 284-285 (1974) https://doi.org/10.1016/S0031-9422(00)91316-5
  25. Talapatra, S. K., Bhar, D. S., and Talapatra, B., Terpenoids and related compounds; Part XIII. Indian J. Chem., 15B, 806-807 (1977)
  26. Triratana, T., Suwannuraks, R., and Naengchomnong, W., Effect of Eupatorium odoratum on blood coagulation. J. Med. Assoc. Thailand, 74, 283-287 (1991)
  27. Wollenweber, E., Dorr, M., and Muniappan, R., Exudate flavonoids in a tropical weed, Chromolaena odorata (L.) R. M. King et H. Robinson. Biochem. Syst. Ecol., 23, 873-874 (1995) https://doi.org/10.1016/0305-1978(95)00080-1
  28. Wollenweber, E. and Roitman, J. N., A novel methyl ether of quercetagetin from Chromolaena odorata leaf exudate. Biochem. Syst. Ecol., 24, 479-480 (1996) https://doi.org/10.1016/0305-1978(96)88879-X