Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Anti-inflammatory and Anti-oxidative Activities of Flavonoids Extracted from Dendranthema indicum Flowers in Jeju Island

제주 자생 감국 꽃 추출물 유래 flavonoid 화합물의 항산화 및 항염 활성

  • 현주미 ((사)제주산학융합원 연구개발팀) ;
  • 조연정 ((사)제주산학융합원 연구개발팀) ;
  • 김윤범 ((주)뉴메디온 제주천연물자원화연구소) ;
  • 박성민 ((주)뉴메디온 제주천연물자원화연구소) ;
  • 윤경섭 (제주대학교 화학.코스메틱스학과) ;
  • 이남호 ((사)제주산학융합원 연구개발팀)
  • Received : 2019.11.28
  • Accepted : 2019.12.28
  • Published : 2019.12.30
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Abstract

Anti-inflammatory and anti-oxidative activities were examined on the extract of Dendranthema indicum (D. indicum) flowers. The flowers were extracted two times for 24 h each with 70% ethanol. Upon the biological activities screening, the ethanol extract exhibited potent free radical scavenging activities and inhibited the production of nitric oxide on LPS-induced RAW264.7 macrophages effectively without causing cell toxicity. Further purification by medium pressure liquid hromatography (MPLC) and identification of the isolates led to identification of cynaroside (1) and apigetrin (2). The chemical structures of the isolated compounds were elucidated based on spectroscopic data including nuclear magnetic resonance (NMR) spectra, as well as comparison of the data to the literature values. Also, the quantitative analysis of the compounds was perfromed by high-performance liquid chromatography (HPLC). The isolates 1 and 2 were determined to inhibite the nitric oxide (NO) production dose-dependently. Based on these results, it was suggested that D. indicum extract could be useful as anti-inflammatory agents in cosmetics applications.

본 연구에서는 감국 꽃 추출물의 항산화 및 항염활성을 검색하고 유효성분을 분리하여 화학구조를 규명하였다. 감국 꽃 에탄올 추출물의 DPPH 및 ABTS+ 라디칼 소거 활성을 측정한 결과 우수한 라디칼 소거 활성이 있음을 확인하였다. 또한 LPS로 유도된 RAW264.7 대식세포에서 세포독성 없이 우수한 nitric oxide (NO) 저해 활성을 나타내었다. 감국 꽃 에탄올 추출물의 유효성분을 찾고자 medium pressure liquid chromatography (MPLC)를 실시하여 2개의 화합물을 분리하였으며 1H 및 13C NMR 데이터 분석 및 문헌 비교를 통하여 화학구조를 동정하였다; Cynaroside (1), Apigetrin (2). 분리된 화합물을 HPLC를 통하여 정량분석을 수행하였으며 감국 꽃 추출물의 주요 성분으로 확인되었다. 화합물 1, 2의 항염활성을 확인한 결과 모두 농도의존적으로 우수한 NO 저해활성을 나타내었다. 이러한 연구 결과를 바탕으로 감국 꽃 추출물은 천연 항산화 및 항염 소재로써 활용 가능할 것으로 사료된다.

Keywords

References

  1. I. R. Tizard, R. M. Schubot, "Veterinary Immunology: An Introduction", W. B Saunders Company, (2008).
  2. I. R. Tizard, "Immunology, An introduction inflammation", Saunders Collage Publishing, Vol.2, pp.423-441, (1986).
  3. E. S. Lee, H. K. Ju, T. C. Moon, E. Lee, Y. Jahng, S. H. Lee, J. K. Son, S. H. Baek, H. W. Chang, "Inhibition of nitric oxide and tumor necrosis factor-alpha (TNF-alpha) production by propenone compound through blockade of nuclear factor (NF)-kappa B activation in cultured murine macrophages", Biol Pharm Bull, Vol.27, pp.617-620, (2004). https://doi.org/10.1248/bpb.27.617
  4. M. Higuchi, N. Higashi, H. Taki, T. Osawa, "Cytolytic mechanisms of activated macrophages. Tumor necrosis factor and L-arginine- dependent mechanisms act synergistically as the major cytolytic mechanisms of activated macrophages", J Immunol, Vol.144, pp.1425-1431, (1990).
  5. J. H. Park, "Studies on the Constituents of Chrysanthemum indicum L.", The J of Nat. Sci., Vol.32, pp.11-17, (1981).
  6. S. J. Kim, Y. M. Park, S. T. Jung, "Anticariogenic Effects and Inhibition of Glucosyltransferase Activity of Chrysanthemun indicum L. Extracts", J. Korean Soc. Food Cult., Vol.20, pp.341-245 2005,
  7. G. H. Bae, Y. H. Kim, B. S. Min, H. J. Jung, H. Huong, J. S. Lee, H. J. Ji, "The quality evaluation of chrysanthemi flos", Kor. J. Pharmacogn., pp.14-17, (1996).
  8. K. S. Jang, "Studies on the Natural pH Adjusters for Kimchi", J. Korean Soc. Food Nutr., Vol.18, No.3, pp.321-327, (1989).
  9. G. S. Park, Y. J. Shin, J. G. Im, "Comparative Degree of Gelatinization and Retrogradation on Gamkugsulgie with Added of Gamkug", J. East Asian Soc. Dietary Life, Vol.10, No.6, pp.514-521, (2000).
  10. G. S. Park, Y. J. Shin, "Mechanical Characteristics and Preferences of Gamkugsulgie-dduk by Different Addition of Chrysanthemum indicum L.", J. East Asian Soc. Dietary Life, Vol.10, No.6, pp.514-521, (2000).
  11. J. Y. Nam, H. S. Lee, S. W. Lee, M. Y. Chung, E. S. Yoo, M. C. Rho, Y. K. Kim, "Effect of Kikkanol F Monoacetate and 5-Hydroxy-6,7,3',4'-tetramethoxyflavone Isolated from Chrysanthemum indicum L. on IL-6 Production", Kor. J. Pharmacogn., Vol.36, No.3, pp.186-190, (2005).
  12. K. Y. Jung, S. R. Oh, C. S. Kim, J. H. Kim, H. K. Lee, "A New Alkyl Alcohol Glycoside from Chrysanthemi Flos", Kor. J. Pharmacogn., Vol.27, pp.15-19, (1996).
  13. Y. J. Shin, "Chemical composition of gamkug and quality characteristics of gamkuksulgie-dduk". Catholic University of Daegu, PhD thesis, (1999).
  14. N. Y. Park, "Volatile flavors of wild and cultivated Chrysanthemum and optimation of ethanol extraction". Kyungbuk National University, MS thesis, (1995).
  15. B. R. Lee, "Inhibitory effect of enzymetreated Chrysanthmum Indicum L. extract on lipid accumulation in in vitro and in vivo models", Wonkwang University, MS thesis, (2019)
  16. J. A. Lee, S. H. Kim, M. J. Kim, J. H. Ahn, H. J. Park, W. R. Lee, S. S. Roh, "Protective Effects of Chrysanthemi Indici Flos Extract and Flaxseed Oil Mixture on HCl/ethanol-induced Acute Gastric Lesion Mice", Kor. J. Herbol. Vol.33, No.6, pp.19-28, (2018) https://doi.org/10.6116/KJH.2018.33.6.19
  17. S. Y. Park, Y. J. Cho, "Anti-Gout Effect of Ethanol Extracts from Chrysanthemum indicum Linne", J Korean Soc Food Sci Nutr, Vol.45, No.6, pp.797-804, (2016) https://doi.org/10.3746/jkfn.2016.45.6.797
  18. Y. J. Cho, B. O. Kim, H. J. Park, E. H. Lee, J. B. Jo, J. E. Lee, S. B.. Lim, Y. J. Kim, K. T. Park, M. Y. Choi, "Inhibition Effect of Phenolic Compounds from Ultra-fine Ground Chrysanthemum indicum L. on Xanthine Oxidase", J of Life Science, Vol.27, No.8, pp.902-908, (2017) https://doi.org/10.5352/JLS.2017.27.8.902
  19. M. R. Kong, S. J. Seo, M. R. Han, Y. S Lee, "Anti-oxidation and Anti-aging Activity of Three Compositae Species at Different Extraction Temperatures", J Invest Cosmetol, Vol.12, No.1, pp.29-37, (2016) https://doi.org/10.15810/jic.2016.12.1.005
  20. J. Y. Sung, W. A. Joe, Y. H. Kim, S. J. Cheon, M. J. Jang, H. J. Choi, J. S. Lee, E. Y. Choi, H. S. Lee, D. I. Kim, J. O. Kim, "Study on the antioxidant activity of extracts from the Chrysanthemum indicum L." J Appl Oriental Med, Vol.7, pp.1-5, (2007).
  21. M. S. Blois, "Antioxidant determination by the use of a stable free radical", Nature, Vol.181, pp.1199, (1958). https://doi.org/10.1038/1811199a0
  22. R. Re, N. Pellegrini, A. Proteggente, A. pannala, M. Yang, and C. Rice-Evans, "Antixoidant activity applying an improved ABTS radical cation decolorization assay", Free Radic Biol Med, Vol.26, No.9, pp.1231, (1999). https://doi.org/10.1016/S0891-5849(98)00315-3
  23. C. Hirobe, A. S. Qiao, K. Takeya, H. Itokawa, "Cytotoxic flavonoids from Vitex agnus-castus", Phytochemistry, Vol. 46, pp.521-524, (1997). https://doi.org/10.1016/S0031-9422(97)00127-1
  24. S. Asnaashari, A. Delazar, S. Seyed Alipour, L. Nahar, Angela S. Williams, A. Pasdaran, M. Mojarab, F. Fathi Azad and S. D. Sarker, "Chemical composition, free-radical-scavenging and insecticidal activities of the aerial parts of Stachys Byzantina", Arch. Biol. Sci., Vol.62, No.3, pp.653-662, (2010). https://doi.org/10.2298/ABS1003653A
  25. H. Tominaga, M. Ishiyama, F. Ohseto, K. Sasamoto, T. Hamamoto, K. Suzuki, M. Watanabe, "A water-soluble tetrazolium salt useful for colorimetric cell viability assay", Anal. Commun. Vol.36, pp.47-50, (1999) https://doi.org/10.1039/a809656b
  26. K. L. Khanduja, A. Bhardwaj, "Stable free radical scavenging and antiperoxidative properties of resveratrol compared in vitro with some other bioflavonoids", Indian Journal of Biochemistry & Biophysics, Vol.40, No.6, pp.416 (2003).
  27. S. K. Jung, K. W. Lee, "Industrial Status of Orental Medicine Cosmetics", Food Science and Industry, pp.45, (2012)
  28. K. D. Kim, S. J. Kim, "Studies on the antimicrobial effects of herbal extracts and it's cosmetic application", J Kor Soc Cosmet, Vol.13, pp.221-227, (2007).
  29. S. Y. Lee, H. S. Seo, "The Effects of Sulfur extract on Anti-inflammation and Anti-propionibacterium acnes", J Korean Medicine Ophthalmology & Otolaryngology & Dermatology, Vol.20, pp.68-76, (2007).