Isolation and Identification of Quercetin with Antioxidative Activity from the Fruits of Rubus coreanum Miquel

복분자 열매에서 항산화활성을 지닌 quercetin의 분리 및 동정

  • Published : 2003.06.01

Abstract

The methanol (MeOH) extracts from the fruits of Rubus coreanum showed antioxidative activity. The antioxidative substance in MeOH extracts was successively purified with solvent fractionation, adsorption chromatography, and gel filtration. The purified active substance was isolated by HPLC and identified as quercetin by EI-MS, and $^1H-NMR$ analyses. The amount of quercetin was 0.25 mg per 100 g in fresh fruits of Rubus coreanum Miquel.

Keywords

fruits of Rubus coreanum Miquel;antioxidative activity;quercetin

References

  1. Halliwell, B.H., Gutteridge, J.M.C. and Arouoma, O.I. The deoxyribose method: A simple 'test-tube' assay for determination of rate constants for reaction of hydroxyl radicals. Anal. Biochem. 165: 215-219 (1987) https://doi.org/10.1016/0003-2697(87)90222-3
  2. Branen, A.L. Toxicological and biochemistry of butylated hydroxytoluene, butylated hydroxyanisole. J. Am. Oil Chem. Soc. 52: 59-63 (1975) https://doi.org/10.1007/BF02901825
  3. Kim, T.J. Korean Resources Plants II, p. 140. Publishing Department of Seoul University, Seoul, Korea (1996)
  4. Lee, Y.A. and Lee, M.W. Tannins from Rubus coreanum. Korean J. Pharmacogn. 26: 27-30 (1995)
  5. Kim, M.S., Pang, G.C. and Lee, M.W. Flavonoids from the leaves of Rubus coreanum. Yakhak Hoeji 41: 1-6 (1997)
  6. Pang, G.C., Kim, M.S. and Lee, M.W. Hydrolyzable tannins from the fruits of Rubus coreanum. Korean J. Pharmacogn. 27: 366-370 (1996)
  7. Abe, N., Nemoto, A., Tsuchiya, Y., Hojo, H. and Hirota, A. Studies of the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Bioscl. Biotech. Biochem. 64: 306-333 (2000) https://doi.org/10.1271/bbb.64.306
  8. Peng, Z.F., Strack, D., Baumert, A., Subramaniam, R., Goh, K.N., Chia, T.F., Tan, S.N. and Chia, L.S. Antioxidant flavonoids from leaves of Polygonum hydropiper L. Phytochemistry 62: 219-228 (2003) https://doi.org/10.1016/S0031-9422(02)00504-6
  9. Markaverich, B.M., Roberts, R.R., Alejandro, M.A., Johnan, G.A., Middleditch, B.S. and Clark, J.M. Bioflavonoid interaction with rat utenne type II binding sites and growth inhibition. J. Steroid Biochem. 30: 71-78 (1998) https://doi.org/10.1016/0022-4731(88)90078-7
  10. Veckenstedt, A., Beladi, I. and Musci, I. Effect of treatment with certain tlavonoids on mengo virus-induced encephalitis in mice. Arch. Virol. 57: 255-260 (1978) https://doi.org/10.1007/BF01315089
  11. Kuk, J.H., Ma, S.J., Moon, J.H., Kim, K.Y., Choi, S.H. and Park, K.H. Antibacterial and antifungal activities of a naphthoquinone derivative isolated from the fruits of Catalpa ovata G. D$_O_N$. J. Microbial. Biotechnol. 12: 858-863 (2002)
  12. William, M., Amanda, J.S., Michael, E.J.L., Peter, G., Garry, G.D. and Alan, C. Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries. J. Agric. Food Chem. 50: 5197-5201 (1999) https://doi.org/10.1021/jf020141f
  13. Hakkinen, S.H., Karenlampi, S.O., Heinonen, I.M., Mykkanen, H.M. and Torronen, A.R. Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries. J. Agric. Food Chem. 47: 2274-2279 (1999) https://doi.org/10.1021/jf9811065
  14. Moon, J.H. and Park, K.H. Functional components and physiological activity of tea. J. Korean Tea Soc. 1: 175-191 (1995)
  15. Gutteridge, J.M.C. and Halliwell, B. Antioxidants in Nutrition, Health and Disease, pp. 1-62. Oxford University Press, UK (1994)
  16. Park, K.H., Park, J.D., Hyun, K.H., Nakayama, M. and Yokota, T. Brassinosteroids and monoglycerides with brassinosteroid-like activity in immature seeds of Oryza sativa and Perilla frutescena and in cultured cells of Nicotiana tabacum. Bioscl. Biotech. Biochem. 58: 224-2243 (1994)
  17. Halliwell, B.H. and Gutteridge, J.M.C. Role of free radical and catalytic metal ions in human disease: An overview. Methods Enzymol. 186: 1-85 (1990) https://doi.org/10.1016/0076-6879(90)86093-B
  18. Ramarathnam, N., Osawa, T., Ochi, H. and Kawakishi, S. The contribution of plant food antioxidants to human health. Trends Food Sci. 6: 75-82 (1995) https://doi.org/10.1016/S0924-2244(00)88967-0
  19. Lu, Y. and Foo, L.Y. Identification and quantification of major polyphenols in apple pomace. Food Chem. 59: 187-194 (1997) https://doi.org/10.1016/S0308-8146(96)00287-7
  20. Takao, T., Kitatani, F. and Sakata, K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Biochem. 58: 1780-1783 (1994) https://doi.org/10.1271/bbb.58.1780
  21. Younes, M. and Siegers, C.P. Inhibitory action of some tlavonoids on enhanced spontaneous lipid peroxidation fellowing glutathione depletion. Planta Medica. 43: 240-244 (1981) https://doi.org/10.1055/s-2007-971503
  22. Moon, H.I., Ahn, K.T., Lee, K.R. and Zee, O.P. Flavonoid compounds and biological activities on the aerial parts of Angelica gigas. Yakhak Hoeji 44: 119-127 (2000)
  23. Lee, M.W. Phenolic compounds from the leaves of Rubus coreanum. Yakhak Hoeji 39: 200-204 (1995)
  24. Lee, S.T., Lee, Y.H., Choi, Y.J., Shon, G.M., Lee, H.J. and Heo, H.S. Comparison of quercetin and soluble tannin in Houttuynia cordata THUNB. according to growth stages and plants parts. Korean J. Med. Crop Sci. 10: 12-16 (2002)
  25. Ham, I.H., Lee, S.J., Kim, H.H., Kang, I.H., Jin, H.O. and Whang, W.K. Standardization and seasonal variation of quercetin glycoside in Eucommiae Folium. Korean J. Phannacogn. 33: 194-199 (2002)
  26. Wee, J.H. and Park, K.H. Isolation of 4-hydroxycinnamic acid, 3methoxy- 4-hydroxycinnamic acid and 3,4-dihydroxybenzoic acid with antioxidative and antimicrobial activity from peanut (Arachis hypogaea) shell. Food Sci. Biotechnol, 10: 551-556 (2001)
  27. Formica, J.V. and Regelson, W. Review of the biology of quercetin and related bioflavonoids. Food Chem. Toxicol. 33: 1061-1080 (1995) https://doi.org/10.1016/0278-6915(95)00077-1
  28. Cho, J.Y., Moon, J.H. and Park, K.H. Isolation and identification of 3-methoxy-4-hydroxybenzoic acid and 3-methoxy-4-hydroxycinnamic acid with antioxidative and antimicrobial activity from hot water extracts of Hovenia dulcis Thunb and conformation of their antioxidative and antimicrobial activity. Korean J. Food Sci. Technol. 32: 1403-1408 (2000)
  29. Gadow, A.V., Joubert, E. and Hansmann, C.F. Comparison of the antioxidant activity of aspalathin with that of other plant phenols of rooibos tea (Aspalathus linearis), $\alpha$-tocopherol, BHT, and BHA. J. Agric. Food Chem. 45: 632-638 (1997) https://doi.org/10.1021/jf960281n
  30. Edenhader, R. and Tang, X. Inhibition of the mutagenicity of 2-nitrotluorene, 3-nitrotluoranthene and I-nitropyrene by flavonoids, coumarins, quinones and other phenolic compound. Food Chern. Toxicol. 35: 357-372 (1996)
  31. Yoon, I., Cho, J.Y., Kuk, J.H., Wee, J.H., Jang, M.Y., Ahn, T.H. and Park, K.H. Identification and activity of antioxidative compounds from Rubus coreanum fruit. Korean J. Food Sci. Technol. 34: 898-904 (2002)