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

복분자 열매에서 항산화활성을 지닌 quercetin의 분리 및 동정

  • Yoon, In (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Wee, Ji-Hyang (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Moon, Jae-Hak (Department of Applied Biology and Chemistry, The Research Institute of Agricultural Resources Development, Konkuk University) ;
  • Ahn, Tae-Hoe (Research Center, Ottogi Food Co., Ltd.) ;
  • Park, Keun-Hyung (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University)
  • 윤인 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 위지향 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 문제학 (건국대학교 응용생물화학과.농업자원개발연구소) ;
  • 안태회 (오뚜기식품 중앙연구소) ;
  • 박근형 (전남대학교 식품공학과 및 농업과학기술연구소)
  • 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.

복분자 열매에 함유된 항산화활성 물질을 탐색하기 위하여 MeOH로 추출하고, 이 추출물을 용매분획하여 EtOAc가용 중성획분을 얻었다. 이 획분에 함유된 항산화활성 물질을 흡착성과 분자체 효과를 이요한 Sephadex LH-20 column chromatography로 정제하고, HPLC에 의해 1종의 항산화활성물질을 단리하였다. 분리된 활성물질의 구조 해석을 위해 EI-MS와 $^1H-NMR$ 분석을 실시하여, 활성물질은 구조식이 $C_{15}H_{10}O_7$이며 분자량이 302인 quercetin으로 동정되었다. 또한 항산화활성 물질 quercetin은 HPLC에 의해 복분자 열매 100g 중에 $0.25{\pm}0.02\;mg$이 함유되어 있는 것으로 분석되었다.

Keywords

References

  1. 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
  2. Gutteridge, J.M.C. and Halliwell, B. Antioxidants in Nutrition, Health and Disease, pp. 1-62. Oxford University Press, UK (1994)
  3. 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
  4. Moon, J.H. and Park, K.H. Functional components and physiological activity of tea. J. Korean Tea Soc. 1: 175-191 (1995)
  5. 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
  6. 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
  7. 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)
  8. 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)
  9. Kim, T.J. Korean Resources Plants II, p. 140. Publishing Department of Seoul University, Seoul, Korea (1996)
  10. Lee, Y.A. and Lee, M.W. Tannins from Rubus coreanum. Korean J. Pharmacogn. 26: 27-30 (1995)
  11. Lee, M.W. Phenolic compounds from the leaves of Rubus coreanum. Yakhak Hoeji 39: 200-204 (1995)
  12. Kim, M.S., Pang, G.C. and Lee, M.W. Flavonoids from the leaves of Rubus coreanum. Yakhak Hoeji 41: 1-6 (1997)
  13. 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)
  14. 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)
  15. 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)
  16. 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
  17. 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)
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  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. 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)
  27. 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
  28. 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
  29. 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)
  30. 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
  31. 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