Constituents of Flowers of Carthamus tinctorius L. and Their Antioxidant Activity

홍화의 성분 분리 및 항산화 활성

  • Choi, Hyun-Gyu (College of Pharmacy, Yeungnam University) ;
  • Jiang, Yan-Fu (College of Pharmacy, Yeungnam University) ;
  • Park, Sung-Hee (Department of Health & Medical Administration, Gyeongnam Provincial Geochangcollege) ;
  • Son, Ae-Ryang (Department of Beauty Design, Gyeongnam Provincial Geochangcollege) ;
  • Na, Min-Kyun (College of Pharmacy, Yeungnam University) ;
  • Lee, Seung-Ho (College of Pharmacy, Yeungnam University)
  • 최현규 (영남대학교 약학대학) ;
  • 강연복 (영남대학교 약학대학) ;
  • 박성희 (경남도립거창대학 보건의료행정과) ;
  • 손애량 (경남도립거창대학 뷰티디자인과) ;
  • 나민균 (영남대학교 약학대학) ;
  • 이승호 (영남대학교 약학대학)
  • Received : 2011.05.19
  • Accepted : 2011.05.26
  • Published : 2011.06.30

Abstract

As part of our ongoing study focused on the discovery of antioxidants from natural products by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, methanol extract of flowers of Carthamus tinctorius L. was found to show potent antioxidant activity. Activity-guided fractionation of the methanol extract lead to the isolation of twenty compounds including two flavonol glycosides, quercertin-3-O-${\beta}$-D-glucopyranoside (12) and kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl-${\beta}$-D-glucopyranoside (18), two flavanone glycosides, (2S)-4',5,6,7-tetrahydroxyflavanone 6-O-${\beta}$-D-glucopyranoside (15) and (2R)-5,7,8',4-tetrahydroxyflavanone 8-O-${\beta}$-D-glucopyranoside (16), and two acetylenic glycosides, 8Z-decaene-4,6-diyne-1-O-${\beta}$-D-glucopyranoside (13) and 4,6-decadiyne-1-O-${\beta}$-D-glucopyranoside (14). Their chemical structures were identified by using spectroscopic analysis. Among them, compounds 12-18 were tested in DPPH assay. Compounds 13-16 were first reported to their antioxidant activity. Quercertin-3-O-${\beta}$-D-glucopyranoside (12) showed the most potent inhibitory effect on DPPH with $IC_{50}$ value of 56.7 ${\mu}M$.

Keywords

References

  1. 이상인 (1981) 본초학, 459-460. 수서원, 서울.
  2. Lee. T. B. (1989) Illustrated flora of Korea. Hyangmunsa, Seoul, Korea.
  3. 배기환 (2000) 한국의 약용식물, 446. 교학사. 서울.
  4. 손성연, 신농본초경, 13. 의도한국사영인 2, 서울.
  5. 이상인, 안덕균 (1992) 본초학, 172. 영림사, 서울.
  6. Kalyarat, K. and Kaew, K. (2006) Antioxidant activity, phenolic compound contents and antimutagenic activity of some water extract of herbs. Thai J. Pharm. Sci. 30: 28-35.
  7. Rhyu, I. C., Lee, Y. M., Ku, Y., Bae, K. W. and Chung, C. P. (1997) The biologic effects of safflower(Carthamus tinctorius Linne) extract and Dipsasi Radix extract on periodontal ligament cells and osteoblastic cells. J. Korean Acad. Periodontol. 27: 867-882.
  8. Roh, J. S., Han, J. Y., Kim, J. H. and Hwang, J. K. (2004) Inhibitory effects of active compounds isolated from Safflower (Carthamus tinctorius L.) seeds for melanogenesis. Biol. Pharm. Bull. 27: 1976-1978. https://doi.org/10.1248/bpb.27.1976
  9. Narong, C., Teerapol, S.,Wilairat, C. and Worawidh, W. (2007) In vitro study of antiviral activity of plant crudeextracts against the foot and mouth disease virus Kasetsart. J. (Nat. Sci.) 41: 97-103.
  10. Lee, J. Y., Chang, E. J., Kim, H. J., Park, J. H. and Choi, S. W. (2002). Antioxidative flavonoids from leaves of Carthamus tinctorius. Arch. Pharm. Res. 25: 313-319. https://doi.org/10.1007/BF02976632
  11. Yoon, J. M., Cho, J. E., Park, Y. H., Kim, T. R., Hahn, Y. and Paik, Y. S. (2003) Thermal stability of the pigments hydroxysafflor yellow A, safflor yellow B, and precarthamin from Safflower (Carthamus tinctorius). Food Chem. Toxicol. 68: 839-843.
  12. Zhou, Y. Z., Ma, H. Y., Chen, H., Qiao, L., Cao, J. Q., Peil, Y. H. (2006) New acetylenic glucosides from Carthamus tinctorius. Chem. Pharm. Bull. 54: 1455-1456. https://doi.org/10.1248/cpb.54.1455
  13. Naoto, K. Kanna, K., Tetsuya, S., Katsunori, K., Yasufumi, F., Katsuya, S., Harumi, A., Takashi, N., Yusuke, A. and Koichi, L. (2006) Serotonin derivatives, major safflower (Carthamus tinctorius L.) seed antioxidants, inhibit low-density lipoprotein (LDL) oxidation and atherosclerosis in apolipoprotein Edeficient mice. J. Agric. Food Chem. 54: 4970-4976. https://doi.org/10.1021/jf060254p
  14. Kim, E. O., Oh, J. H., Lee, S. K., Lee, J. J. and Choi, S. W. (2007) Antioxidant properties and quantification of phenolic compounds from safflower (Carthamus tinctorius L.) seeds. Food Sci. Biotechnol. 16: 71-77.
  15. Wang, L. F., Zhang, H. Y. (2003) A theoretical investigation on DPPH radical-scavenging mechanism of edaravone. Bioorg. Med. Chem. Lett. 13: 3789-3792. https://doi.org/10.1016/j.bmcl.2003.07.016
  16. Na, M.K., An, R.B., Lee, S.M., Min, B.S., Kim, Y.H., Bae, K.H., K, S.S. (2002). Antioxidant compounds from the stem bark of Sorbus commixta. Nat. Prod. Sci. 8: 26-29.
  17. Akihisa, T., Yasukawa, K., Oinuma, H., Kasahara, Y., Yamanouchi, S., Takido, M., Kumaki, K. and Tamura, T. (1996) Triterpene alcohols from the flowers of Compositae and their anti-inflammatory effects. Phytochemistry 43: 1255-1260. https://doi.org/10.1016/S0031-9422(96)00343-3
  18. Knowles, P. F. (1965) Variability in oleic and linoleic acid contents of safflower oil. Economic Botany 19: 53-62. https://doi.org/10.1007/BF02971186
  19. Hartley, R. D., Ford, C. W., Russell, R. B. (1989) Phenolic constituents of plant cell walls and wall biodegradability. Plant Cell Wall Polymers 9: 137-145.
  20. Zhao, M. B., Yoichiro, I. and Pengfei, T. (2005) Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorium (Honghua) by high-speed counter-current chromatography. J. Chromatog A 1090: 193-196. https://doi.org/10.1016/j.chroma.2005.07.010
  21. Allais, D. P., Chulia, A. J., Kaouadji, M., Simon, A. and Delage, C. (1995) 3-Desoxycallunin and 2''-acetylcallunin, two minor 2,3-dihydroflavonoidglucosides from Calluna vulgaris. Phytochemistry 39: 427-430. https://doi.org/10.1016/0031-9422(94)00910-L
  22. Pratt, D. E. (1976) Role of flavones and related compounds in retarding lipid-oxidative flavor change in food. P. 1. In: Phenolic, sulfur and Nitrogen Compounds in food Flavors. American Chemical Society, Washington DC, USA.
  23. Sohal, R, S., Weindruch, R. (1996) Oxidative stress, caloric restriction, and aging. Science 273: 59-63. https://doi.org/10.1126/science.273.5271.59
  24. Kang, P., Izumo, S. (2000) Apoptosis and heart failure: critical review of the literature. Circ. Res. 86: 1107-1113. https://doi.org/10.1161/01.RES.86.11.1107