Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Antimycobacterial and Antioxidant Flavones from Limnophila geoffrayi

  • Suksamrarn, Apichart (Department of Chemistry, Faculty of Science, Ramkhamhaeng University) ;
  • Poomsing, Ponsuda (Department of Chemistry, Faculty of Science, Ramkhamhaeng University) ;
  • Aroonrerk, Nuntana (Department of Stomatology, Faculty of Dentistry, Srinakharinwirot University) ;
  • Punjanon, Tadsanee (Department of Medical Sciences, Faculty of Science, Rangsit University) ;
  • Suksamrarn, Sunit (Department of Chemistry, Faculty of Science, Srinakharinwirot University) ;
  • Kongkun, Somkiat (Department of Chemistry, Faculty of Science, Ramkhamhaeng University)
  • Published : 2003.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

The chloroform extract of the aerial part of Limnophila geoffrayi showed antimycobacterial and antioxidant activities. Bioassay-guided fractionation has led to the isolation of the flavones nevadensin (5,7-dihydroxy-6,8,4'-trimethoxyflavone, 1) and isothymusin (6,7-dimethoxy-5,8,4'-trihydroxyflavone, 2). Both compounds 1 and 2 exhibited inhibition activity against Mycobacterium tuberculosis, with equal MIC value of $200{\;}\mu\textrm{g}/mL$. Only compound 2 exhibited antioxidant activity against the radical scavenging ability of DPPH, with the $IC_{50}$ value of $7.7{\;}\mu\textrm{g}/mL$. The crude hexane, chloroform and methanol extracts as well as the pure compounds 1 and 2 did not exhibit mutagenic activity in the Bacillus subtilis recassay.

Keywords

References

  1. Barberan, F. A. T., Ferreres, F., and Tomas, F., TLC, UV and acidic treatment in the differentiation of 5,6- and 5,8-dihydroxyflavones, 3-methoxyflavones and flavonols. Tetrahedron, 41, 5733-5740 (1985) https://doi.org/10.1016/S0040-4020(01)91379-1
  2. Barberan, F. A. T., Ferreres, F., Tomas, F., and Guirado, A., Electron impact mass spectrometric differentiation of 5,6-dihydroxy-7,8-dimethoxy- and 5,8-dihydroxy-6,7-dimethoxyflavones. Phytochemistry, 25, 923-925 (1986) https://doi.org/10.1016/0031-9422(86)80028-0
  3. Brand-Williams, W., Cuvelier, M. E., and Berset, C., Use of a free radical method to evaluate antioxidant activity. Food Sci. Technol., 28, 25-30 (1995)
  4. Bunyapraphatsara, N. and Chokechaijaroenporn, O., Faculty of Pharmacy, Mahidol Univercity and National Center for Genetic and Engineering and Biotechnology. Thai Medicinal Plants, 3, 53 (2000)
  5. 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)
  6. Farkas, L., Nogradi, M., Sudarsanam, V., and Herz, W., Constituents of Iva species. V. Isolation, structure, and synthesis of nevadensin, a new flavone from Iva nevadensis M. E. Jones and Iva acerosa (Nutt.) Jackson. J. Org. Chem., 31, 3228-3231 (1966) https://doi.org/10.1021/jo01348a031
  7. Ferreres, F., Barberan, F. A. T., and Tomas, F., 5,6,4'-Trihydroxy-7,8-dimethoxyflavone from Thymus membranaceus. Phytochemistry, 24, 1869-1871 (1985) https://doi.org/10.1016/S0031-9422(00)82579-0
  8. Greenham, J., Vassiliades, D. D., Harborne, J. B., Williams, C. A., Eagles, J., Grayer, R. J., and Veitch, N. C., A distinctive flavonoid chemistry for the anomalous genus Biebersteinia. Phytochemistry, 56, 87-91 (2001) https://doi.org/10.1016/S0031-9422(00)00355-1
  9. Horie, T., Kawamura, Y., Yamamoto, H., Kitou, T., and Yamashita, K., Synthesis of 5,8-dihydroxy-6,7-dimethoxyflavones and revised structures for some natural flavones. Phytochemistry, 39, 1201-1210 (1995) https://doi.org/10.1016/0031-9422(95)00070-N
  10. Horie, T., Ohtsuru, Y., Shibata, K., Yamashita, K., Tsukayama, M., and Kawamura, Y., $^{13}C$-NMR spectral assignment of the A-ring of polyoxygenated flavones. Phytochemistry, 47, 865-874 (1998) https://doi.org/10.1016/S0031-9422(97)00629-8
  11. Horie, T., Shimoo, H., Masumura, M., and Okumura, S., Demethoxysudachitin. Nippon Kagaku Zasshi, 83, 602-604 (1962) https://doi.org/10.1246/nikkashi1948.83.5_602
  12. Kada, T., Tutikawa, K., and Sadaie, Y., In vitro and hostmediated 'rec-assay' procedures for screening chemical mutagens, and phloxine, a mutagenic red dye detected. Mutation Res., 16, 165-174 (1972) https://doi.org/10.1016/0027-5107(72)90177-7
  13. Kelm, M. A., Nair, M. G., Strasburg, G. M., and DeWitt, D. L., Antioxidant and cyclooxygenase inhibitory phenolic compounds from Ocimum sanctum Linn. Phytomedicine, 7, 7-13 (2000) https://doi.org/10.1016/S0944-7113(00)80015-X
  14. Liu, M. C., Chen, Z. S., Chung, L. C., Yang, M. S., Ho, S. T., and Chen, M. T., Studies on hypotensive constituents of Limnophila rugosa. Chung-hua Yao Hsueh Tsa Chih, 43, 35-40 (1991)
  15. Saralamp, P. and Chuakul W., editors. Encyclopaedia of Medicinal Plants, Vol. 4: Kok Ya E-sarn (Medicinal Plants of the Northeast). Mahidol University Foundation, Bangkok, p. 159, (1999)
  16. Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M., and Gray, J. I., Antioxidant polyphenols from tart cherries (Prunus cerasus). J. Agri. Food Chem., 47, 840-844 (1999) https://doi.org/10.1021/jf980936f