Antioxidant and antimicrobial constituents of Crucianella maritima L.

  • Badr, Jihan M. (Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University)
  • 발행 : 2008.12.31

초록

Phytochemical further investigation of the chloroform extract of the aerial parts of Crucianella maritima L. (Rubiaceae) growing in Egypt resulted in the isolation of a new anthraquinone; 3-formyl-1-hydroxy-2-methoxy anthraquinone (3) along with the four known compounds isolated for the first time from the genus Crucianella; alizarin-1-methyl ether (2), 1,4-dihydroxy-2-methoxy anthraquinone (5), 1, 3, 6-trihydroxy-2-methoxy anthraquinone (7) and the flavonol kaempferol (8), beside four known compounds previously isolated from the same plant. The structures of the isolated compounds were established based on different spectroscopic data including UV, IR, EIMS, 1D and 2D-NMR. Moreover, the antioxidant and antimicrobial activities of the isolated compounds were evaluated.

키워드

참고문헌

  1. Andrade-Neto, V.F., Brandão, M.G., Stehmann, J.R., Oliveira, L.A., and Krettli, A.U., Antimalarial activity of Cinchona-like plants used to treat fever and malaria in Brazil. J Ethnopharmacol. 87, 253-256 (2003) https://doi.org/10.1016/S0378-8741(03)00141-7
  2. Arpornsuwan , T. and Punjanon, T., Tumor cell-selective antiproliferative effect of the extract from M. citrifolia fruits. Phytother Res. 20, 515- 517 (2006) https://doi.org/10.1002/ptr.1902
  3. El-Lakany, A.M., Aboul-Ela, M.A., Abdel-Kader, M.S., Badr, J.M., Sabri, N.N., and Goher, Y., Anthraquinones with antibacterial activities from C. maritima L. growing in Egypt. Nat. Prod. Sciences, 10, 63-68 (2004)
  4. El-Gamal, A.A., Takeya, K., Itokawa, H., Halim, A.F., Amer, M.M., Saad, H.E. A. and Awad, S.A., Anthraquinones from G. sinaicum. Phytochemistry 40, 245-251 (1995) https://doi.org/10.1016/0031-9422(95)00145-W
  5. Gupta, S., Zhang, D., Yi, J., and Shao, J., Anticancer activities of O. diffusa. J. Herb. Pharmacother. 4, 21-33 (2004) https://doi.org/10.1300/J157v04n01_03
  6. Hamza, O.J.M., van den Bout-van den Beukel, C.J.P., Matee, M.I.N., Moshi, M.J., Mikx, F.H.M., Selemani, H.O., Mbwambo, Z.H., and Verweij, P.E., Antifungal activity of some Tanzanian plants used traditionally for the treatment of fungal infections. J Ethnopharmacol. 108, 124-132 (2006) https://doi.org/10.1016/j.jep.2006.04.026
  7. Jasril, N.H., Lajis, L.Y., Mooi, L.Y., Abdullah, M.A., Sukari, M.A., and Ali, A.M., Antitumour promoting and antioxidant activities of anthraquinones isolated from the cell suspension culture of M. elliptica. As. Pac. J. Mol. Biol. Biotechnol. 11, 3-7 (2003)
  8. Jose, G.A., Omar, M.C., Fernando, B., Robert, B., Jose, P.C., Andres, N., and Rachel, M., Antidiabetic properties of selected Mexican copalchis of the Rubiaceae family. Phytochemistry 68, 2087-2095 (2007) https://doi.org/10.1016/j.phytochem.2007.05.006
  9. Kalyoncu, F., Cetin, B., and Saglam, H., Antimicrobial activity of common madder (R. tinctorum L.). Phytother Res. 20, 490-492 (2006) https://doi.org/10.1002/ptr.1884
  10. Kariba, R.M., Antimicrobial activity of H. parvifolium. Fitoterapia 73, 523-525 (2002) https://doi.org/10.1016/S0367-326X(02)00176-4
  11. Kim, Y., Park, E.J., Kim, J., Kim, Y., Kim, S.R., and Kim, Y.Y., Neuroprotective constituents from H. diffusa. J. Nat. Prod. 64, 75-78 (2001) https://doi.org/10.1021/np000327d
  12. Koumaglo, K., Gbeassor, M., Nikabu, O., de Souza, and Werner, C.W., Effects of three compounds extracted from M. lucida on Plasmodium falciparum. Planta Med. 58, 533-534 (1992) https://doi.org/10.1055/s-2006-961543
  13. Koyama, J., Ogura, T., and Tagahara, K., Anthraquinones of G. spurium. Phytochemistry 33, 1540-1542 (1993) https://doi.org/10.1016/0031-9422(93)85131-A
  14. Kuiper, J. and Labadie, R.P., Polyploid complexes within the genus Galium. Planta Med. 42, 390-399 (1981) https://doi.org/10.1055/s-2007-971661
  15. Kumar, B., Vijayakumar, M., Govindarajan, R., and Pushpangadan, P., Ethnopharmacological approaches to wound healing-exploring medicinal plants of India. J Ethnopharmacol. 114, 103-113 (2007) https://doi.org/10.1016/j.jep.2007.08.010
  16. Lin, C.C., Ng, L.T., and Yang J.J., Antioxidant activity of extracts of pehhue- juwa- chi-cao in a cell free system. A.J.C.M. 32, 339-349 (2004) https://doi.org/10.1142/S0192415X04001990
  17. Lin, C.C., Ng, L.T., Yang J.J., and Hsu, Y.F., Anti-inflammatory and hepatoprotective activity of extracts of peh-hue-juwa- chi-cao in male rats. A.J.C.M. 30, 225-234 (2002) https://doi.org/10.1142/S0192415X02000405
  18. Mandal, S.C., Mohana Lakshmi, S., Ashok Kumar, C.K., Sur, T.K., and Boominathan, R., Evaluation of anti-inflammatory potential of P. indica Linn. leaf extract (family: Rubiaceae) in rats. Phytother. Res. 17, 817-820 (2003) https://doi.org/10.1002/ptr.1095
  19. Manojlovic, N.T., Solujic, S., Sukdolak, S., and Milosev, M., Antifungal activity of R. tinctorum, Rhamnus frangula and Caloplaca cerina. Fitoterapia 76, 244-246 (2005) https://doi.org/10.1016/j.fitote.2004.12.002
  20. Mavi, A., Terzi, Z., Ozgen, U., Yildirim, A., and Coskun, M., Antioxidant properties of some medicinal plants: P. ferulacea (Apiaceae), S. sempervivoides (Crassulaceae), M. neglecta (Malvaceae), C. taurica (Rubiaceae), R. pimpinellifolia (Rosaceae), G. verum subsp. verum (Rubiaceae), U. dioica (Urticaceae). Biol. Pharm. Bull. 27, 702-705 (2004) https://doi.org/10.1248/bpb.27.702
  21. Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K., Antifeedant activity of an anthraquinone aldehyde in G. aparine L. against Spodoptera litura F. Phytochemistry 60, 163-166 (2002) https://doi.org/10.1016/S0031-9422(02)00095-X
  22. Nijveldt, R.J., Nood, E., Hoorn, D.E.C., Boelens, P.G., Norren, K., and Leeuwen, P.A.M., Flavonoids: a review of probable mechanism of action and potent applications. Am. J. Clin. Nutr., 74, 418-425 (2001) https://doi.org/10.1093/ajcn/74.4.418
  23. Palu , A.K., Kim, A.H., West, B.J., Deng, S., Jensen, J., and White, L., The effects of M. citrifolia L. (noni) on the immune system: its molecular mechanisms of action. J Ethnopharmacol. 115, 502-506 (2008) https://doi.org/10.1016/j.jep.2007.10.023
  24. Pawlus, A.D., Su, B.N., Keller, W.J., and Kinghorn, A.D., An anthraquinone with potent quinine reductase-inducing activity and other constituents of the fruits of M. citrifolia (Noni). J. Nat. Prod. 68, 1720-1722 (2005) https://doi.org/10.1021/np050383k
  25. Takamatsu, S., Hodges, T.W., Rajbhandari, I., Gerwick, W.H., Hamann, M.T., and Nagle, D.G., Marine natural products as novel antioxidant prototypes. J. Nat. Prod, 66, 605-608 (2003) https://doi.org/10.1021/np0204038
  26. Wang, M.Y., Nowicki, D., Anderson, G., Jensen, J., and West, B., Liver Protective Effects of M. citrifolia (Noni). Plant Foods Hum Nutr. 63, 59-63 (2008) https://doi.org/10.1007/s11130-008-0070-3
  27. Yoshida, Y., Wang, M.Q., Liu, J.N., Shan, B.E., and Yamashita, U., Immunomodulating activity of Chinese medicinal herbs and O. diffusa in particular. Int. J. Immunopharmacol. 19, 359-370 (1997) https://doi.org/10.1016/S0192-0561(97)00076-3
  28. Zhou, Z., Jiang, S.H., Zhu, D.Y., Lin, L.Z., and Cordell, G.A., Anthraquinones from K. valerianoides. Phytochemistry 36, 765-768 (1994) https://doi.org/10.1016/S0031-9422(00)89813-1