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Antioxidant Activity and Radioprotection of Two Flavonoids from Propolis

프로폴리스에서 분리한 플라보노이드 화합물의 항산화 활성 및 방사선 방어효과

  • 정일윤 (한국원자력 연구소 방사선식품·생명공학연구팀)
  • Published : 2005.02.01

Abstract

Two flavonoids, 7-O-methyl-3',4'-didehydroxy quercetin (MDQ) and quercetin, isolated from Chinese propolis, which is the generic name for the resinous substance collected by honeybees from various plant sources, were tested for their antioxidant activity and protective effect against radiation-induced DNA damage in mouse lymphocytes. In antioxidant test, both compounds provided a dose-dependent scavenging effect on DPPH radical and a dose-dependent inhibitory effect on lipid peroxidation in mouse liver. Quercetin showed stronger scavenging and inhibitory effect than MDQ, and it also provided strong inhibition on superoxide anion radical generated in xanthine-xanthine oxidase system, but there was no inhibitory ability for MDQ. In comet assay using single cell gel electrophoresis, MDQ and quercetin showed a protective effect against DNA damage caused by gamma irradiation. They reduced DNA damage to 54% (p<0.01) and 53% (p<0.01) at 25 $\mu$mol, respectively. These results suggest that free radical scavenging seems to be associated with their catechol form on the B ring, and radioprotection appears to be a likely mechanism of antioxidant activity by these flavonoids.

프로폴리스에서 분리한 MDQ 및 quercetin의 작용기에 따른 항산화 효과를 비교 분석하고 방사선 조사에 의한 DNA의 산화적 손상에 있어서 두 화합물이 어느 정도의 방어효과가 있는지를 측정 하고자 하였다. 두 화합물의 항산화 활성 시험(DPPH 라디칼 소거활성, 지질과산화 억제활성, superoxide anion 라디칼 소거활성)에서 quercetin이 MDQ보다 훨씬 강한 항산화 활성을 보였으며, 특히 superoxide anion라디칼 소거활성 시험에서 MBQ는 거의 활성을 보이지 않았지만 quercetin은 농도 의존적인 강한 소거활성을 보였다. 또한, mouse 림프구에서 방사선 조사에 의한DNA의 산화적 손상에 대한 두 화합물의 방어효과 시험에서 MDQ와 Quercetin은 동일 농도에서 거의 유사한 방사선 방어효과가 관찰되었다. 상기의 결과로부터 두 화합물의 작용기를 고려해 볼 때 B ring에 있는 catechol작용기의 존재 유무에 따라서 항산화 활성의 차이가 있으며 또한 MDQ화합물의 C ring에 존재하는 methoxy group은 quercetin에 존재하는 hydroxy group과 비교해 볼 때 항산화를 비활성화시키는 작용기의 하나로서 판단되어진다. 따라서 본 실험의 결과로 미루어 볼 때 방사선 방어 효과는 항산화 활성에 미치는 메카니즘과 유사하게 작용하는 것으로 판단되어지며 아울러 일차적으로 항산화 활성 물질을 검색함으로써 산화적 스트레스에 의한 DNA에 대한 방어물질 검색 수단으로서 유용할 것으로 사료된다. 이상의 결과로부터 프로폴리스는 산화적 스트레스에 대한 경감제로서 그 가능성이 시사되었다.

Keywords

References

  1. Fridovich I. 1974. Superoxide radical and the bacterial action of phagocytes. J Med 290: 624-625
  2. McCord JM. 1974. Free radical and inflammation: Protection of synovial fluid by superoxide dismutase. Science 185: 529-531 https://doi.org/10.1126/science.185.4150.529
  3. Fridovich I. 1978. The biology of oxygen radicals. Science 201: 875-880 https://doi.org/10.1126/science.210504
  4. Lynch RE, Fridovich I. 1978. Effect of superoxide on erythrocyte membrane. J Biol Chem 253: 1838-1845
  5. Freeman BA, Grapo JD. 1982. Biology of disease: free radicals and tissue injury. Lab Invest 47: 412-426
  6. Fridovich I. 1986. Biological effects of the superoxide radical. Arch Biochem Biophys 247: 1-11 https://doi.org/10.1016/0003-9861(86)90526-6
  7. Wanscher B. 1976. Contact dermatitis from propolis. J Dermatol 94: 451-455 https://doi.org/10.1111/j.1365-2133.1976.tb06125.x
  8. Havsteen B. 1983. Flavonoids, a class of natural products of high pharmacological potency. Biochemical Pharmacology 32: 1141-1148 https://doi.org/10.1016/0006-2952(83)90262-9
  9. Dobrowolski JW, Vohora SB, Sharma K, Shah SA, Naqvi SAH, Dandiya PC. 1991. Antibacterial, antifungal, antiamoebic, antiinflammatory and antipyretic studies on propolis bee products. J Ethnopharmacol 35: 77-82 https://doi.org/10.1016/0378-8741(91)90135-Z
  10. Frenkel K, Wei H, Bhimani R, Ye J, Zaduanisky JA, Huang M, Ferraro T, Conney AH, Grunberger D. 1993. Inhibition of tumor promoter-mediated processes in mouse skin and bovine lens by caffeic acid phenethyl ester. Cancer Res 53: 1255-1261
  11. Pascual C, Gonzalez R, Toricella RG. 1994. Scavenging action of propolis extract against oxygen radicals. J Ethnopharmacol 41: 9-13 https://doi.org/10.1016/0378-8741(94)90052-3
  12. Tatefuji T, Izumi N, Ohta T, Arai S, Ikeda M, Kurimoto M. 1996. Isolation and identification of compounds from Brazilian which enhance macrophage spreading and mobility. Biol Pharm Bull 19: 966-970 https://doi.org/10.1248/bpb.19.966
  13. Lin S, Lin Y, Chen C, Chung C, Hsu S. 1977. The hepatoprotective and therapeutic effects of propolis ethanol extract on chromic alcohol-induced liver injuries. Am J Chin Med 25: 325-332
  14. Miyataka H, Nishiki M, Matsumoto H, Fujimoto T, Matsuka M, Satoh T. 1997. Evaluation of Brazilian and Chinese propolis by enzymatic and physico-chemical methods. Biol Pharm Bull 20: 496-501 https://doi.org/10.1248/bpb.20.496
  15. Munstedt K. 2001. Proplis, current and future medical uses. American Bee J 141: 506-507
  16. Sud'ina GF, Mirzoeva OK. 1993. Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties. FEBS 329: 2-24
  17. Krol W, Scheller S, Czuba Z, Matsuno T, Zydowicz G. 1996. Inhibition of neutrophils' chemiluminescene by ethanol extracts of propolis and its phenolic components. J Ethnopharmacol 55: 19-25 https://doi.org/10.1016/S0378-8741(96)01466-3
  18. Nardini M, Natella F, Gentili V, Maurizio C, Felice D. 1977. Effect of caffeic acid dietary supplementation on the antioxidant defense system in rat. Arch Biochem Biophys 342: 157-160
  19. Cizmarik J, Matel I. 1978. Study of the chemical structure of propolis. Isolation and identificatio of 4-oxy-3-methoxycinnamic acid from propolis. In Propolis. Apimondia Publishing House, Bucharest, Romania. p 30
  20. Vachalkova A, Novotny L, Solivajsova A, Suchy V. 1995. Polarographic behavior of flavonoids from propolis and their potential carcinogenity. Bioelectrochemistry and Bioenergetics 36: 137-143 https://doi.org/10.1016/0302-4598(94)01754-O
  21. Chung HY, Kim HB. 2000. In vitro studies in the superoxide scavenging activities, the cytotoxic and the immunomodulating effects of thirteen kinds of herbal extracts. Korean J Food Sci Technol 32: 699-705
  22. Singh NP, Stephens RE, Schneider EL. 1995. Induction of DNA single-strand breaks in human lymphocytes by low doses of ${\gamma}-ray$. J Radiat Biol 66: 563-569
  23. Fossen T, Pedersen A, Andersen OM. 1997. Flavonoids from red onion (Allium cepa). Phytochemistry 47: 281-285 https://doi.org/10.1016/S0031-9422(97)00423-8

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