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Composition of Flavonoids and Antioxidative Activity from Juice of Jeju Native Citrus Fruits during Maturation

수확시기별 제주재래종 감귤착즙액의 Flavonoids 분포 및 항산화 활성

  • Kim, Yong-Dug (Research and Development Center, Jeju Special Self-Governing Province Development Corp.) ;
  • Ko, Weon-Jun (Research and Development Center, Jeju Special Self-Governing Province Development Corp.) ;
  • Koh, Kyung-Soo (Research and Development Center, Jeju Special Self-Governing Province Development Corp.) ;
  • Jeon, You-Jin (Faculty of Marine Biomedical Science, Jeju National University) ;
  • Kim, Soo-Hyun (Department of Food Bioengineering, Jeju National University)
  • 김용덕 (제주특별자치도개발공사 연구소) ;
  • 고원준 (제주특별자치도개발공사 연구소) ;
  • 고경수 (제주특별자치도개발공사 연구소) ;
  • 전유진 (제주대학교 해양의생명과학부) ;
  • 김수현 (제주대학교 식품생명공학과)
  • Published : 2009.04.30

Abstract

This study aims to evaluate the changes of flavonoid contents and antioxidants activity of Jeju native citrus fruits juice according to the harvest date. Flavonoids such as quercatagetin, narirutin, hesperidin and neohesperidin were contained most plentifully in the juice of Jigak (Citrus aur-antium) by 573.73 mg/100 mL, Sadoogam (C. pseudogulgul) by 393.99 mg /100 mL, Soyooja by 29.63 mg/100 mL and Jigak (C. aurantium) by 201.23 mg/100 mL in the late August, respectively. The highest contents of nob-iletin, sinensetin and tangeretin among polymethoxyflavones were found in the juice of Hongkyool (C. tachibana) by 7.39 mg/100 mL, 2.24 mg/100 mL, 0.63 mg/100 mL in the late August, respectively. 3,5,6,7,8,3',4'- Heptamet- hoxyflavone recorded the highest amount in Punkyool (C. tangerina) by 0.27 mg/100 mL in the late August, but the other polymethoxyflavones including 3',4',7,8-tetramethoxyflavone, 3',4'-dimethoxyflavone, 4'-methoxyflavone, 5,6,7,3',4',5'-hexamethoxyflavone, scutellarein tetramethylether were observed only trace amount in all the citrus fruits. Flavonoid contents in the citrus fruit juices were the highest during early maturation and decreased rapidly while ripening. Total polyphenol contents were the highest in the late August and decreased with ripening. However from the late December, the contents were increased again. Antioxidant activities of the fruits were evaluated as electron donating ability and were the lowest in the late September and increased with the fruit ripening. These results suggest that quercetagetin among all the flavonoids was most plentiful in Jigak and Dangyooja (C. grandis), so that the fruits could be used for industrial material of flavonoids and antioxidant agents.

제주재래종 감귤류 14종의 착즙액에 대해서 수확시기별 flavonoids 13종의 함량변화를 분석하고 항산화성을 검토하고자 하였다. 감귤착즙액의 flavonoids 함량은 수확시기가 늦어질 수록 큰 폭으로 감소하다가 4${\sim}$5차 채취기 이후 서서히 증가하는 경향을 보였다. Quercatagetin, narirutin, hesperidin, neohesperidin은 각각 지각 573.73 mg/100 mL, 사두감 393.99 mg/100 mL, 소유자 29.63 mg/100 mL, 지각 201. 23 mg/100mL으로 미숙과인 8월 하순에 가장 높았다. Polymethoxyflavone류 중 nobiletin, sinensetin, tangeretin은 홍귤에서 8월 하순에 각각 7.39 mg/100 mL, 2.24 mg/100 mL, 0.63 mg/100 mL으로 가장높았고, 다음으로 진귤이 많이 함유되어 있었다. 3,5,6,7,8,3',4'-Heptamethoxyflavone은 편귤에서 0.27 mg/100mL으로 가장 높았고, 3',4',7,8-tetramethoxyflavone, 3',4'-dimethoxyflavone, 4'-methoxyflavone, 5,6,7,3',4',5'-hexamethoxyflavone, scutellarein tetramethylether는 모든 품종에서 ND${\sim}$0.08 mg/100mL로 함량이 낮았다. 총 폴리페놀 함량은 대부분의 시료가 미숙과인 8월 하순에 가장 높았다가 11월까지 감소하다가 12월 하순부터 증가하는 경향을 보였다. 감귤착즙액의 전자공여능은 대체적으로 높은 것으로 나타났으나 flavonoids와 총폴리페놀 함량과의 상관관계는 높지 않은 경향을 보였고 당유자가 가장 높은 항산화활성을 나타내었다. 재래 감귤류 중 지각, 당유지는 quercetagetin이 다른 감귤류에 비해 월등히 높았고, polymethoxyflavone류인 nobiletin과 tangeretin은 미숙과인 홍귤과 진귤에서 함량이 높아 소재 개발로서 경쟁력이 있을 것으로 사료된다.

Keywords

References

  1. Jeju Special self-Governing Province, Annual report of statistics 2006; 2007
  2. Rhyu MR, Kim EY, Bae IY, Park YK. Contents of naringin, hesperidin and neohesperidin in premature Korean citrus fruits. Korean J Food Sci Technol 2002; 34 (1): 132-135
  3. Eun JB, Jung YM, Woo GJ. Identification and determination of dietary fibers and flavonoids in pulp and peel of Korean tangerine (Citrus aurantium var.). Korean J Food Sci Technol 1996; 28 (2): 371-377
  4. Song EY, Choi YH, Kang KH, Koh JS. Free sugar, organic acid, hesperidin, naringin and inorganic elements changes of Cheju citrus fruits according to harvest date. Korean J Food Sci Technol 1998; 30 (2): 306-312
  5. Lee CH, Kang YJ. HPLC analysis of some flavonoids in citrus fruits. Korean J Postharvest Sci Technol 1997; 4 (2): 181-187
  6. Veldhuis MK, Swift LJ, Scott WC. Fully-methoxylated flavones in florida orange juices. J Agric Food Chem 1970; 18(4): 590-592 https://doi.org/10.1021/jf60170a009
  7. Ting SV, Rouseff RL, Dougherty MH, Attaway JA. Determination of some methoxylated flavones in citrus juices by high performance liquid chromatography [HPLC]. J Food Sci 1979; 44 (1): 69-71 https://doi.org/10.1111/j.1365-2621.1979.tb10006.x
  8. Del Rio JA, Arcas MC, Benavente O, Sabater F, Ortuno A. Changes of polymethoxylated flavone levels during development of Citrus aurantium (cv. Sevillano) fruits. Planta Med 1998; 64: 575-576 https://doi.org/10.1055/s-2006-957519
  9. Ortuno AM, Arcas MC, Benavente-Garcia O, Del Río JA. Evolution of polymethoxyflavones during development of tangelo Nova fruits. Food Chem 1999; 66(2): 217-220 https://doi.org/10.1016/S0308-8146(99)00047-3
  10. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. Quantitation of flavonoid constituents in Citrus fruits. J Agric Food Chem 1999; 47(9): 3565-3571 https://doi.org/10.1021/jf990153+
  11. Kawaii S, Tomono Y, Katase E, Ogawa K, Nonomura-Nakano M, Nesumi H, Yoshida T, Sugiura M, Yano M. Quantitative study of fruit flavonoids in Citrus hybrids of King (C. nobilis) and Mukaku Kishu (C. kinokuni). J Agric Food Chem 2001; 49(8): 3982-3986 https://doi.org/10.1021/jf0100292
  12. Kim YC, Koh KS, Koh JS. Changes of flavonoids in the peel of Jeju native citrus fruits during maturation. Food Sci Biotechnol 2001; 10(5): 483- 487
  13. Baik SO, Bock JY, Chun HJ, Jeong SI, Han WS, Kim IK. Quantitative distribution and analysis of methoxylated flavonoids in citruses and Korean chung-pi. Anal Sci Technol 2001; 14(4): 331-339
  14. Nogata Y, Sakamoto K, Shiratsuchi H, Ishii T, Yano M, Ohta H. Flavonoid composition of fruit tissues of citrus species. Biosci Biotechnol Biochem 2006; 70(1): 178-192 https://doi.org/10.1271/bbb.70.178
  15. Jeong WS, Park SW, Chung SK. The antioxidative activity of Korean Citrus unshiu peels. Foods Biotechnol 1997; 6(4): 292-296
  16. Kim HJ, Bae KH, Eun JB, Kim MK. Effects of hesperidin extracted from tangerine peel on Cd and lipid metabolism, and antioxidative capacity in rats. Korean J Nutr 1999; 32(2): 137-149
  17. Anagnostopoulou MA, Kefalas P, Papageorgiou VP, Assimopoulou AN, Boskou D. Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis). Food Chem 2006; 94(1): 19-25 https://doi.org/10.1016/j.foodchem.2004.09.047
  18. Mokbel MS, Hashinaga F. Evaluation of the antioxidant activity of extracts from buntan (Citrus grandis Osbeck) fruit tissues. Food Chem 2006; 94(4): 529-534 https://doi.org/10.1016/j.foodchem.2004.11.042
  19. Kurowska EM, Borradaile NM, Spence JD, Carroll KK. Hypocholester- olemic effects of dietary citrus juice in rabbits. Nutr Res 2000; 20(1): 121-129 https://doi.org/10.1016/S0271-5317(99)00144-X
  20. Kim BK, Cha JY, Cho YS. Effects of citrus flavonoid, hesperidin and naringin on lipid metabolism in HepG2 cells. Korean J Life Sci 1999; 9(4): 382-388
  21. Lio M, Uyeda M, Iwanami T, Nakagawa Y. Flavonoid as a possible preventive of dental carries. Agric Biol Chem 1984; 48(8): 2143- 2145
  22. Han SS, You IJ. Studies on antimicrobial activities and safety of natural naringin in Korea. Kor J Mycol 1988; 16(1): 1-8
  23. Son HS, Kim HS, Kwon TB, Ju JS. Isolation, purification and hypotensive effect of bioflavonoids in Citrus sinensis. J Korean Soc Food Sci Nutr 1992; 21(2): 136-142
  24. Hertog MGL, Hollman PCH, Katan MB. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 1992; 40(12): 2379-2383 https://doi.org/10.1021/jf00024a011
  25. Middleton E Jr, Kandaswami C. Potential health-promoting properties of citrus flavonoids. Food Technology 1994; 48(11): 115-119
  26. El-Shafae AM. Bioactive polymethoxyflavones and flavanone glycosides from the peels of Citrus deliciosa. Honghua yao xue za zhi 2002; 54: 199-206
  27. Hirano T, Abe K, Gotoh M. Oka K. Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes. Br J Cancer 1995; 72: 1380-1388
  28. AOAC. Official Method of Analysis. 15th ed. Method 914-915 Association of Official Analytical Chemists, Washington, DC, USA; 1985
  29. Kang YH, Park YK, Lee GD. The nitrite scavenging and electron donating ability of phenolic compounds. J Korean Food Sci Technol 1996; 28(2): 232-239
  30. Hertog MG, Feskens EJ, Hollman PC, Katan MB, Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 1993; 342(8878): 1007-1011 https://doi.org/10.1016/0140-6736(93)92876-U
  31. Li S, Mao W, Cao X, Liang S, Ding Z, Li N. Inhibition of rat lens aldose reductase by quercetagetin and patuletin. Yan Ke Xue Bao 1991; 7(1): 29-30
  32. Parejo I, Bastida J, Viladomat F, Codina C. Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima. Phytochemistry 2005; 66: 2356-2362 https://doi.org/10.1016/j.phytochem.2005.07.004
  33. Mouly P, Gaydou EM, Auffray A. Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography. J Chromatography A 1998; 800(2): 171-179 https://doi.org/10.1016/S0021-9673(97)01131-X
  34. Kang YJ, Yang MH, Ko WJ, Park SR, Lee BG. Studies on the major components and antioxidative properties of whole fruit powder and Juice prepared from premature mandarin orange. Korean J Food Sci Technol 2005; 37(5): 783-788
  35. Cha JY, Kim SY, Jeong SJ, Cho YS. Effects of hesperetin and naringenin on lipid concentration in orotic acid treated mice. Korean J Life Sci 1999; 9(4): 389-394
  36. Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K, Hara A, Sumida T, Tanaka T, Ogawa H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally ccurring flavonoids, diosmin and hesperidin. Carcinogenesis 1997; 18(5): 957 -965 https://doi.org/10.1093/carcin/18.5.957
  37. Ishiwa J, Sato T, Mimaki Y, Sashida Y, Yano M, Ito A. A Citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts. J Rheumatol 2000; 27(1): 20-25
  38. Bracke ME, Bruyneel EA, Vermeulen SJ, Vennekens K, Maeck VN, Mareel MN. Citrus flavonoid effect on tumor invasion and metastasis. Food Technol 1994; 48: 121-124
  39. An BJ, Bae MJ, Choi HJ, Zhang YB, Sung TS, Choi C. Isolation of polyphenol compounds from the leaves of Korean Persimmon (Diospyrus kaki L. Folium). J Korean Soc Agric Chem Biotechnol 2002; 45(4): 212-217
  40. Ahmad N, Gupta S, Mukhtar H. Green tea polyphenol epigallocatechin- 3-gallate differentially modulates nuclear factor $\kappa$B incancer cells versus normal cells. Archives Biochem Biophy 2000; 376(2): 338-346 https://doi.org/10.1006/abbi.2000.1742
  41. Yoo KM, Hwang IK. In vitro effect of yuza (Citrus junos SIEB ex TANAKA) extracts on proliferation of human prostate cancer cells and antioxidant activity. Korean J Food Sci Technol 2004; 36(2): 339-344
  42. Yoo KM, Kim CE, Kim DI, Huh D, Hwang IK. Antioxidant activity and physicochemical characteristics of tangerine peel tea prepared with Citrus unshiu cultivated in Cheju. Korean J Food Cookery Sci 2005; 21(3): 354-359
  43. Oh HS, An YS, Na IS, Oh MC, Oh CK, Kim SH. Inhibition of n-nitrosodimethylamine formation of extracts from citrus seeds. Korean J Food Cookery Sci 2003; 19(5): 640-646
  44. Jung SJ, Lee JH, Song HN, Seong NS, Lee SE, Baek NI. Screening for antioxidant activity of plant medicinal extracts. J Korean Soc Appl Biol Chem 2004; 47(1): 135-140
  45. Jayaprakasha GK, Patil BS. In vitro evaluation of the antioxidant activities in fruit extracts from citron and blood orange. Food Chemistry 2007; 101: 410-418 https://doi.org/10.1016/j.foodchem.2005.12.038
  46. Lim HK, Yoo ES, Moon JY, Jeon YJ, Cho SK. Antioxidant activity of extracts from Dangyuja (Citrus grandis Osbeck) fruits produced in Jeju Island. Food Sci Biotechnol 2006; 15(2): 312-316

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