Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Radical Scavenging Constituents of Cyperus flaccidus

  • Received : 2012.04.18
  • Accepted : 2012.05.11
  • Published : 2012.06.30
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Abstract

In the course of screening for antioxidant compounds by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging effect and superoxide quenching activity, methanol extract of Cyperus flaccidus (Cyperaceae) was found to show potent antioxidant activities. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of ten compounds, kaempferol-3,7-O-${\alpha}$-L-dirhamnopyranoside (1), caffeic acid (2), quercetin-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (3), kaempferol-3-O-${\alpha}$-L-rhamnopyranoside (4), quercetin-3-O-${\alpha}$-L-rhamnopyranoside (5), luteoiln-7-O-${\beta}$-D-glucopyranoside (6), kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (7), luteoiln (8), quercetin (9) and quercetin-3-O-${\beta}$-D-glucuronide (10). Their structures were elucidated by spectroscopic studies. Compounds 1 - 10 were isolated for the first time from this plant. Among them, compounds 2, 8 and 9 showed the significant radical scavenging effects on DPPH, and the potent xanthine-originated superoxide quenching activities.

Keywords

References

  1. Bouktaib, M., Atmani, A., and Rolando, C., Regio- and steroselective synthesis of the major metabolite of quercetin, quercetin-3-O-$\beta$-D-glucuronide. Tetrahedron Lett. 43, 6263-6266 (2002). https://doi.org/10.1016/S0040-4039(02)01264-9
  2. Devi, K.R., Suganthy, N., Kesika, P., and Pandian, S.K., Bioprotective properties of seaweeds: In vitro evaluation of antioxidant activity and antimicrobial cativity against food borne bacteria in relation to polyphenolic content. BMC Complement. Altern. Med. 8, 1-11 (2008). https://doi.org/10.1186/1472-6882-8-1
  3. Hasan, A., Ahmed, K., Jay, M., and Voirin, V., Flavonoid glycosides and anthraquinone from Rumex chalepensis. Phytochemistry 39, 1211-1213 (1995). https://doi.org/10.1016/0031-9422(95)00071-E
  4. Hong, H.K., Kwak, J.H., Kang, S.C., Lee, J.W., Park, J.H., Ahn, J.W., Kang, H.S., Choung, E.S., and Zee, O.P., Antioxidative Constituents from the Whole Plants of Euphorbia supina. Kor. J. Pharmacogn. 39, 260-264 (2008).
  5. Hur, J.M., Park, J.C., and Hwang, Y.H., Aromatic Acid and Flavonoids from the Leaves of Zanthoxylum piperitum. Nat. Prod. Sci. 7, 23-26 (2001).
  6. Jang, K.G., Oh, H., Ko, E.K., Kang, K.H., Park, S.E., Oh, M.H., and Kim, Y.C., Free Radical Scavengers from the Leaves of Albizzia julibrissin. Kor. J. Pharmacogn. 33, 28-30 (2002).
  7. Kim, S.H., Hwang, K.T., and Park, J.C., Isolation of flavonoids and determination of rutin from the leaves of Ulmus parviflora. Kor. J. Pharmacogn. 23, 229-233 (1992).
  8. Kumaran, A. and Karunakaran, R.J., Antioxidant and free radical scavenging activity of and aqueous extract of Coleus aromaticus. Food Chem. 97, 109-114 (2006). https://doi.org/10.1016/j.foodchem.2005.03.032
  9. Lee, H.J., Lee, S.K., Choi, Y.J., Jo, H.J., Kang, H.Y., and Choi, D.H., Extractives from the bark of Platycarya strobilacea. Journal of Korean Forest Society 96, 408-413 (2007).
  10. 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).
  11. Lee, S.K., Park, W.G., and Bae, Y.S., Procyanidins from Lindera obtusiloba bark. Mokchae konghak 25, 110-116 (1997).
  12. Lee, W.T., Coloured standard illustrations of Korean plants, Academy Pub. Co., Seoul, pp. 468, 1996.
  13. Moon, J.H., Tsushida, T., Kakahara, K., and Terao, J., Identification of quercetin 3-O-$\beta$-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radic. Biol. Med. 30, 1274-1285 (2001). https://doi.org/10.1016/S0891-5849(01)00522-6
  14. Moreno, A., Martin-Cordero, C., Iglesias-Guerra, F., and Toro, M.V., Flavonoids from Dorycnium rectum. Biochem. Sys. Eco. 30, 73-74 (2002). https://doi.org/10.1016/S0305-1978(01)00070-9
  15. 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
  16. Wu, Z.J., Ouyang, M.A., and Yang, C.R., Polyphenolic constituents of Salvia onchifolia. Acta Bot. Yunnan 21, 393-398 (1999).
  17. Yoshida, T., Mori, K., Hatano, T., Okumura, T., Uehara, L., Komagoe, K., Fujita, Y., and Okuda, T., Studies on inhibition mechanism of autooxidation by tannins and flavonoids. V. Radical scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37, 1919-1921 (1989). https://doi.org/10.1248/cpb.37.1919