Superoxide Quenching Activity of Phenolic Compounds from the Whole Plant of Galium verum var. asiaticum

  • Received : 2011.08.11
  • Accepted : 2011.09.30
  • Published : 2011.12.30

Abstract

During the process of screening for antioxidative effects of natural plants in Korea, by measuring the superoxide quenching activity, methanol extract of the whole plant, Galium verum var. asiaticum (Rubiaceae), was found to show potent antioxidant activity. Subsequent activity-guided fractionation of methanol extract of Galium verum var. asiaticum led to the isolation of five phenolic compounds. Using spectroscopic techniques, the chemical structures were elucidated as: caffeic acid (1), narcissin (2), rutin (3), luteolin-7-O-${\alpha}$-L-rhamnopyranosyl (1 ${\rightarrow}$ 2)-${\beta}$-D-glucopyranoside (4), and luteolin-7-O-${\beta}$-D-glucopyranoside (5). These compounds were isolated for the first time from this plant. Among them, compound 1 showed the most significant riboflavin-originated superoxide and xanthine-originated superoxide quenching activities. Compounds 3 and 4 exhibited mild superoxide quenching effects compared with vitamine C.

Keywords

References

  1. Bojthe-Horvath, K., Hetenyi, F., Kocsis, A., Szabo, L., Varga-Balazs, M., MatheJr., I., and Tetenyi, P., Iridoid glycosides from Galium verum. Phytochemistry 21, 2917-2919 (1980). https://doi.org/10.1016/0031-9422(80)85068-0
  2. Choi, D.S., Kim, S.J., and Jung, M.Y., Inhibitory activity of berberine on DNA strand cleavage induced by hydrogen peroxide and cytochrome c. Biosci. Biotechnol. Biochem. 65, 452-455 (2001). https://doi.org/10.1271/bbb.65.452
  3. Choi, J.S. and Woo, W.S., Phenolic Compounds of the roots of Bupleurum longeradiatum. Arch. Pharm. Res. 12, 226-228 (1989). https://doi.org/10.1007/BF02855560
  4. Coleta, M., Batista, M.T., Campos, M.G., Carvalho, R., Cotrim, M.D., Lima, T.C., and Cunha, A.P., Neuropharmacological evaluation of the putative anxiolytic effects of Passiflora edulis Sims, its sub-fractions and flavonoid constituents. Phytother Res. 20, 1067-1073 (2006). https://doi.org/10.1002/ptr.1997
  5. El-Gamal, A.A., Takeya, K., Itokawa, H., Halim, A.F., Amer, M.M., Saad, H.E.A., and Awad S.A., Anthraquinones from Galium sinaicum. Phytochemistry 40, 245-251 (1995). https://doi.org/10.1016/0031-9422(95)00145-W
  6. Er, T.K., Tsai, S.M., Wu, S.H., Chiang, W., Lin, H.C., Lin, S.F., Wu, S.H., Tsai, L.Y., and Liu, T.Z., Antioxidant status and superoxide anion radical generation in acute myeloid leukemia. Clin. Biochem. 40, 1015-1019 (2007). https://doi.org/10.1016/j.clinbiochem.2007.05.013
  7. Ginnopolitis, C.N. and Ries, S.K., Superoxide dismutase. I. Occurrence in higher plants. Plant Physiol. 59, 309-314 (1977). https://doi.org/10.1104/pp.59.2.309
  8. Hanaoka, K., Sun, D., Lawrence, R., Kamitani, Y., and Fernandes, G., The mechanism of the enhanced antioxidant effects against superoxide anion radicals of reduced water produced by electrolysis. Biophys. Chem. 107, 71-82 (2004). https://doi.org/10.1016/j.bpc.2003.08.007
  9. Handjieva, N., Mitova, M., Ancev, M., and Popov, S., Iridoid glucosides from Galium album and G. lovcense. Phytochemistry 43, 625-628 (1996). https://doi.org/10.1016/0031-9422(96)00328-7
  10. Kim, D.K. (2009) Antioxidative constituents from the twigs of Vitex rotundifolia. Biomol. Ther. 17, 412-417. https://doi.org/10.4062/biomolther.2009.17.4.412
  11. Lee, T.B., In Coloured flora of Korea. Hyangmunsa, Seoul, pp. 696, 2003.
  12. Lee, W.T., In Coloured standard illustration of Korean plants. Academy Publishing Co., Seoul, pp. 691, 1996.
  13. Lee, S.I., Yang, J.H., Baek, N.I., Kim, S.H., Cho, C.H., Park, B.H., Chae, B.S., and Kim, D.K., Free radical scavengers from the fruits of Paeonia suffruticosa. Nat. Prod. Sci. 14, 202-205 (2008).
  14. Lee, S., Han, S., Kim, H.M., Lee, J.M., Mok, S.Y., and Lee, S., Isolation and identification of phytochemical constituents from Taraxacum coreanum. J. Korean Soc. Appl. Biol. Chem. 54, 73-78 (2011).
  15. Lee, S.I., Yang, J.H., and Kim. D.K., Antioxidant flavonoids from the twigs of Stewartia koreana. Biomol. Ther. 18, 191-196 (2010). https://doi.org/10.4062/biomolther.2010.18.2.191
  16. Lee, H., Yang, S., Park, S., Yang, J.H., Chae, B.S., Eun, J.S., Jeon, H., Lim, J.P., Hwang, Y.H., Park, J.H., and Kim, D.K., Antioxidative Constituents of Cyperus difformis L. Nat. Prod. Sci. 15, 241-245 (2009).
  17. Lim, H.W., Kang, S.J., Park, M., Yoon, J.H., Han, B.H., Choi, S.E., and Lee, M.W., Anti-oxidative and nitric oxide production inhibitory activities of phenolic compounds from the fruits of actinidia arguta. Nat. Prod. Sci. 12, 221-225 (2006).
  18. Mabry, T.J., Markham, K.R., and Thomas, M.B., The ultraviolet spectra of flavones and flavonols. In The Systematic Identification of Flavonoids. pp. 41-164, Springer, New York, USA (1970).
  19. Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K., Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F. Phytochemistry 60, 163-166 (2002). https://doi.org/10.1016/S0031-9422(02)00095-X
  20. de Rosa, S., Iodice, C., Mitova, M., Handjieva, N., Popov, S., and Anchev, M., Triterpene saponins and iridoid glucosides from Galium rivale. Phytochemistry 54, 751-756 (2000). https://doi.org/10.1016/S0031-9422(00)00149-7
  21. Thuong, P.T., Kang, H.J., Na, M.K., Jin, W.Y., Youn, U.J., and Seong, Y.H., Anti-oxidant constituents from Sedum takesimense. Phytochemistry 68, 2432-2438 (2007). https://doi.org/10.1016/j.phytochem.2007.05.031
  22. Uesato, S., Ueda, M., Inouye, H., Kuwajima, H., Yatsuzuka, M., and Takaishi, K., Iridoids from Galium mollugo. Phytochemistry 23, 2535-2537 (1984). https://doi.org/10.1016/S0031-9422(00)84093-5
  23. Wu, S.J. and Ng, L.T., Antioxidant and free radical scavenging activities of wild bitter melon (Momordica charantia Linn. var. abbreviata Ser.) in Taiwan. LWT - Food Science and Technology 41, 323-330 (2008). https://doi.org/10.1016/j.lwt.2007.03.003