YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Isolation of Flavonoids from Carthami Flos and their Antioxidative Activity

홍화의 플라보노이드 성분 분리 및 항산화 활성

  • Published : 2008.08.31
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Abstract

In this study, isolation of antioxidative compounds was performed for development of anti-oxidizing agent. $CHCl_{3}$, $H_{2}O$, 30%, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method, TBARS assay, and SOD like activity. It was revealed that 30%, 60% MeOH fractions had significant antioxidative activity. From 30%, 60% MeOH fraction, nine compounds were isolated and elucidated kaempferol $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), quercetin $7-O-{\beta}-D-glucopyranoside$ (II), quercetin $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)$ ${\beta}-D-glucopyranoside(rutin)$ (III), 6-hydroxykaempferol $3-O-{\beta}-D-glucopyranoside$ (lV), kaempferol $3-O-{\beta}-D-glucopyranosyl$ $(1{\rightarrow}2)$ ${\beta}-D-glucopyranoside$ (V), kaempferol $3-O-{\beta}-D-glucopyranoside$ (VI), luteolin (VII), quercetin $3-O-{\beta}-D-glucopyranoside$ (VIII), apigenin $7-O-{\beta}-D-glucuronopyranoside$ (IX) through physicochemical data and spectroscopic methods (Negative FAB-MS, $^1H-NMR$, $^{13}C-NMR$). Entirely, all compounds had similar antioxidative activity, but more OH group had more antioxidative activity.

Keywords

References

  1. 대한 약전 제 8개정 대한 약전외 한약(생약) 규격집
  2. 배기환 : 한국의 약용식물, 교학사, p. 446 (2000)
  3. 한국약용식물학 연구회 : 종합 약용식물학, 학창사, p. 278 (2005)
  4. Sevim, K. : Moisture sorption and thermodynamic properties of safflower petals and tarragon. Journal of Food Engineering 78, 413 (2007) https://doi.org/10.1016/j.jfoodeng.2005.10.009
  5. 손성연 : 신농본초경, 의도한국사영인 2, 서울, p. 13
  6. 이상인, 안덕균 : 본초학, 영림사, 서울, p. 178 (1992)
  7. Hatano, T., Edamatsu, R., Hiramatus, M., Mori, A., Fujita, Y., Yasuhara, T., Yoshida, T. and Okuda, T. : Effects of the interaction of tannins with co-existing substances. IV. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37, 2016 (1989) https://doi.org/10.1248/cpb.37.2016
  8. Chun, S. and Shetty, K. : Phenolic antioxidants from clonal oregano (Origanum vulgare) with antimicrobial activity against Helicobacter pylori. Process Biochemistry 40, 809 (2005) https://doi.org/10.1016/j.procbio.2004.02.018
  9. Hiroshi, O., Nobuko, O. and Kunio, Y. : Assay for lipid peroxides in animal tissues by thiobarbituric acid reation. Anal. Biochem. 95, 351 (1979) https://doi.org/10.1016/0003-2697(79)90738-3
  10. 김라민 : 수종 천연 약물과 계피의 항 알러지 작용 연구 (1995)
  11. Agrawal, P. : Carbon-13 NMR of flavonoids. Elsevier 332 (1989)
  12. Harbone, J. and Marbry, T. : The Flavonoids : Advance in Reserch., Campman and Hall (1993)
  13. Tang, W. and Eisenbrand, G. : Chinese Drugs of Plant Origin, Springer-Verlag, 919-26 (1992)
  14. Spyridon, D. K., Despo, K. P. and Alexandros, D. : Cultivar and seasonal effects on the contribution of pre-anthesis assimilates to safflower yield. Field Crops Research 90, 263 (2004) https://doi.org/10.1016/j.fcr.2004.03.009
  15. Shimokoriyama, M. : On the formation of carthamin in the flowers of Carthamus tinctorius. Arch. Biochem. 54, 93 (1955) https://doi.org/10.1016/0003-9861(55)90011-4
  16. Goda, Y., Suzuki, J. and Yoshihira, K. : Studies on highperformance liquid chromatographic analysis of safflomin A and B in safflower yellow and commercial safflower yellows. Eisei Shikenjo Hokoku 106, 101 (1988)
  17. Nakato, K., Sekino, Y. and Yomo, N. : High-performance liquid chromatography of carthamin, safflor yellow A and a precursor of carthamin. J. Chromatogr. 438, 61 (1988) https://doi.org/10.1016/S0021-9673(00)90233-4
  18. Watanabe, T. and Hasegawa, N. : Separation and determination of yellow and red safflower pigments in food by capillary electrophoresis. Biosci. Biotechnol. Biochem. 61, 1179 (1997) https://doi.org/10.1271/bbb.61.1179
  19. Liu, Y. and Zhou, H. : Study on distribution of safflr yellow A in tissues of mice. Yao Xue Xue Bao 39, 217 (2004)
  20. Cho, M. and Hahn, T. : Purification and characterization of precarthamin decarboxylase from the yellow petals of Carthamus tinctorius L. Arch. Biochem. Biophys. 382, 238 (2000) https://doi.org/10.1006/abbi.2000.1984
  21. Kazuma, K., Takahashi, T. and Sato, K. : Quinochalcones and flavonoids from fresh florets in different cultivars at Carthamus tinctorius L. Biosci. Biotechnol. Biochem. 64, 1588 (2000) https://doi.org/10.1271/bbb.64.1588
  22. Shingo, S. and Toshikatsu, N. : Studies on the synthesis of safflomin-A, a yellow pigment in safflower petals : oxidation of 3-C-$\beta$-d-glucopyranosyl-5-methylphloroacetophenone. Carbohydrate Research 340, 389 (2005) https://doi.org/10.1016/j.carres.2004.12.019
  23. Shingo, S., Takashi, K. and Tohru, S. : Efficient synthesis of analogs of safflower yellow B, carthamin, and its precursor: two yellow and one red dimeric pigments in safflower petals. Tetrahedron 61, 9630 (2005) https://doi.org/10.1016/j.tet.2005.07.080
  24. Ligang, C. and Lan, D. : Dynamic microwave-assisted extraction coupled with on-line spectrophotometric determination of safflower yellow in Flos Carthami. Analytical Chimica Acta. 580, 75 (2006) https://doi.org/10.1016/j.aca.2006.07.040
  25. Tsimidou, M. and Tsatsaroni, E. : Stability of saffron pigments in aqueous extracts. J. Food Sci. 58, 1073 (1993) https://doi.org/10.1111/j.1365-2621.1993.tb06116.x
  26. Saito, K. and Murata, T. : The influence of thermal treatments on the stability of safflor yellow B. Food Chem. 51, 307 (1994) https://doi.org/10.1016/0308-8146(94)90031-0
  27. Kim, J. and Park, Y. : Stability of carthamin from Carthamus tinctorius in aqueous solution; pH and temperature effects. Arch. Pharm. Bull. 41, 1796 (1997)
  28. Yoon, J. and Cho, M. : Thermal stability of the pigments hydroxysafflor yellow A, safflor yellow B, and precarthmin from safflower. Journal of Food Science 68, 839 (2003) https://doi.org/10.1111/j.1365-2621.2003.tb08252.x
  29. Jiang, T. and Lv, Z. : Separation and determination of chalcones from Carthamus tinctorius L. and its medicinal preparation by capillary zone electrophoresis. J. Sep. Sci. 28, 1244 (2005) https://doi.org/10.1002/jssc.200500001
  30. Zhang, H. and Nagatsu, A. : Antioxidative compounds isolated from safflower (Carthamus tinctorius L.) oil cake. Chem. Pharm. Bull. (Tokyo) 45, 1910 (1997) https://doi.org/10.1248/cpb.45.1910
  31. Li, Y. and Che, Q. : Studies on chemical components of Carthamus tinctorius petals. Yao Xue Xue Bao. 33, 626 (1998)
  32. Srinivas, C. and Praveena, B. : Safflower petals: a source of gamma linolenic acid. Plant Foods Hm Nutr. 54, 89 (1999) https://doi.org/10.1023/A:1008107521247
  33. Lee, J., Chang, E. and Kim, H. : Antioxidative flavonoids from leaves of Carthamus tinctorius. Arch. Pharm. Res. 25, 313 (2002) https://doi.org/10.1007/BF02976632
  34. Tsutomu, K., Susumu, T. and Hidetaka, N. : A novel and potent biological antioxidant, Kinobeon A, from cell culture of safflower. Life Science 74, 87 (2003) https://doi.org/10.1016/j.lfs.2003.06.033
  35. Zhou, Y. and Ma, H. : New acetylenic glucosides from Carthamus tinctorius. Chem. Pharm. Bull. (Tokyo) 54, 1455 (2006) https://doi.org/10.1248/cpb.54.1455
  36. Wang, B., Yang, M. and Pang, L. : Effect of Hong-Hua (Flos Carthami) on the extent of myocardial ischemia in the different infarct zones following coronary occlusion in the dog. Yao Xue Xue Bao 14, 474 (1979)
  37. Gong, C. and Yu, P. : Effects of Flos Carthami Co injection in the treatment of scleroma neonatorum. J. Tradit. Chin. Med. 3, 141 (1983)
  38. Liu, Y. and Murong, S. : Effects of flos Carthami on betaendorphin levels in brain regions of rats with cerebral ischemia. Zhongguo Zhong Xi Yi Jie He Za Zhi 17, 169 (1997)
  39. Nobakht, M. and Fattahi, M. : A study on teratogenic and cytotoxic effects of safflower extract. J. Ethnopharmacol. 73, 453 (2000) https://doi.org/10.1016/S0378-8741(00)00324-X
  40. Siow, Y. and Choy, P. : Effect of Flos carthami on stressactivated protein kinase activity in the isolated reperfused rat heart. Mol. Cell. Biochem. 207, 41 (2000) https://doi.org/10.1023/A:1017266628572
  41. Bie, X. : Clinical observation on treatment of traumatic intracranial hematoma by flos Carthami combined with radix Acanthopanacis senticosi injection. Zhongguo Zhong Xi Yi Jie He Za Zhi 23, 296 (2003)
  42. Akiko, S. and Takako, Y. : Antioxidative effects related to the potential anti-aging properties of the Chinese prescription Kangen-karyu and Carthami Flos in senescence-accelerated mice. Archives of Gerontology and Geriatrics 39, 69 (2004) https://doi.org/10.1016/j.archger.2004.01.001
  43. Hanania, M. and Duarte, R. : Folk medicine/herbal remedies: Topical safflower plant extract for chronic pain: An open-label prospective study. The Journal of Pain 5, S52 (2004) https://doi.org/10.1016/j.jpain.2004.02.173
  44. Roh, J. and Han, J. : Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis. Biol. Pharm. Bull. 27, 1976 (2004) https://doi.org/10.1248/bpb.27.1976
  45. Jin, M., Li, J. and Wu, W. : Study on the antioxidative effect of safflor yellow. Zhongguo Zhong Yao Za Zhi. 29, 447 (2004)
  46. Fenghua, F. and Chunfang, S. : Effect of safflower yellow a on the blood pressure in dog and man. American Journal of Hypertension 18, A59 (2005)
  47. He, C. and Jin, Z. : Enhancement of thrombolytic activities of Carthamus tinctorius processed with fermentation with a Bacillus sp. C2-13. Zhongguo Zhong Yao Za Zhi. 30, 340 (2005)
  48. Zhang, Q. and Peng, J. : A clinical study of safflower yellow injection in treating coronary heart disease angina pectoris with Xin-blood stagnation syndrome. Chin. J. Integr. Med. 11, 222 (2005) https://doi.org/10.1007/BF02836509
  49. Hsu, S. and Huang, C. : Reduced fat mass in rats fed a high oleic acid-rich safflower oil diet is associated with changed in expression of hepatic PPARalpha and adipose SREBP-1cregulated genes. J. Nutr. 136, 1779 (2006) https://doi.org/10.1093/jn/136.7.1779