Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Antioxidative Flavonoids from Leaves of Carthamus tinctorius

  • Lee, Jun-Young (Department of Food Science and Nutrition, Catholic University of Daegu) ;
  • Chang, Eun-Ju (Department of Food Science and Nutrition, Catholic University of Daegu) ;
  • Kim, Hyo-Jin (Department of Food Science and Nutrition, Catholic University of Daegu) ;
  • Park, Jun-Hong (Uisong Medicinal Plant Experiment Station, Gyeongbuk Provincial A.T.A.) ;
  • Choi, Sang-Won (Department of Food Science and Nutrition, Catholic University of Daegu)
  • Published : 2002.06.01
Download PDF
⟨ Previous Next ⟩

Abstract

A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

Keywords

References

  1. Ahmed, A. A., Mabry, T. J., and Matlin, S. A., Flavonoids of the flowers of Silybum marianum. Phytochemistry, 28, 1751-1753(1989) https://doi.org/10.1016/S0031-9422(00)97838-5
  2. Bae, S. J., Shim, S. M., Park, Y. J., Lee, J. Y., Chang, E. J., and Choi, S. W., Cytotoxicity of phenolic compounds isolated from the seeds of safflower( Carthamus tinctorius L.) on cancer cell lines. Food Sci. Biotechnol., 11,140-146 (2002)
  3. Baek, N. I., Kim, Y. H., Ahn, E. M., Bang, M. H., Nam, J. Y., and Kwon, B. M., Isolation of biologically active compounds from the flower petals of Carthamus tinctorius L. Agr. Chem. Biotechnol., 41,197-200 (1998)
  4. heng, I. F., and Breen, K. On the ability of four flavonoids, baicalein, luteolin, naringenin, and quercetin, to suppress the Fenton reaction of the iron-ATP complex. Biometals, 13, 77-83(2000) https://doi.org/10.1023/A:1009229429250
  5. Cho, S. H., Choi, S. W., Choi, Y S. and Lee, W. J. Effects of defatted safflower and perilla seed powders on lipid metabolism in ovariectomized female rats fed high cholesterol diets. J. Kor. Soc. Food Sci. Nutr., 30, 112-118(2001)
  6. Chung, S. Y., Choi, H. J., Chung, M. W., Ahn, M. R., Yoo, T. M., Rheu, H. M., and Yang, J. S. Effects of safflower seed on the fracture healing in rat tibia. Yakhak Hoeji, 43, 526-534(1999)
  7. DiSilvestro, R. A. Flavonoids as antioxidants. In: Handbook of nutraceuticals and functional foods (Wildman, R. E. C., ed), CRC Press, Boca Raton, NewYork, pp.127-142, 2001
  8. Farmakalidis, E., and Murphy, P. A. Isolation of 6'-O-acetylgenistein and 6'-O-acetyldaidzin from toasted defatted soyflakes. J. Agric. Food Chem., 33, 385-389(1985) https://doi.org/10.1021/jf00063a016
  9. Flamini, G., Antognoli, E., and Morelli, I. Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy. Phytochemistry, 57, 559-564(2001) https://doi.org/10.1016/S0031-9422(01)00066-8
  10. Halliwell, B., Gutteridge, J. M. C., and Aruoma, O. I. The deoxyribose method: a simple test tube assay for determination of rate constants for reaction of hydroxyl radicals. Anal. Biochem., 165,215-219 (1987) https://doi.org/10.1016/0003-2697(87)90222-3
  11. Han, D. S. Sangyakhak, Dongmyungsa Press, Seoul, pp. 270-271,1988
  12. Harborne, J. Appendix A. Checklist of known flavone and flavonol glycosides. In: The flavonoids, Springer-Verlag, New York, pp. 370-385, 1994
  13. Hilsenbeck, R. A., and Mabry, T. J. C-Glycosylflavones from Siphonoglossa sessilis. Phytochemistry, 22, 2215-2217(1983) https://doi.org/10.1016/S0031-9422(00)80150-8
  14. Huang, Y. T., Hwang, J. J., Lee, P. P., Ke, F. C., Huang, J. H., Huang, C. J., Kandaswami, C., Middleton, E., and Lee, M. T. Effects of luteolin and quercetin, inhibitors of tyrosinase kinase, on cell growth and metastasis-associated properties in A431 cells overexpressing epidermal growth factor receptor. British J. Pharmacol., 128, 999-1010 (1999) https://doi.org/10.1038/sj.bjp.0702879
  15. Husain, S. R., Cillard, J., and Cillard, P. Hydroxyl radical scavenging activity of flavonoids. Phytochemistry, 26, 2489-2491(1987) https://doi.org/10.1016/S0031-9422(00)83860-1
  16. Iwashina, T., Matsumoto, S., Ozawa, K., and Akuzawa, K. Flavone glycosides from Asplenium normale. Phytochemistry, 29, 3543-3546 (1990) https://doi.org/10.1016/0031-9422(90)85272-H
  17. Izumi, T., Nasu, A., Kataoka, S., Tokutake, S., Obata, A., and Tobe, K. An efficient preparation of acetyl isoflavone glucoside. Chem Pharm. Bull., 45,1593-1595 (1997) https://doi.org/10.1248/cpb.45.1593
  18. Kang, G. W., Chang, E. J., and Choi, S. W. Antioxidative activity of phenolic compounds in roasted safflower (Carthamus tinctorus L.) seeds. J. Food Sci. Nutr., 4, 221-225 (1999)
  19. Kawashima, S., Hayashi, M., Takii, T., Kimura, H., Zhang, H. L., Nagatsu, A., Sakakibara, J., Murata, K., Oomoto, Y., and Onozaki, K. Serotonin derivative, N-(p-coumaroyl)serotonin, inhibits the production of TNF-, IL-1, IL-1, and IL-6 by endotoxin-stimulated human blood monocytes. J. Interfer. Cytokin. Res., 18,423-428 (1998) https://doi.org/10.1089/jir.1998.18.423
  20. Kim, H. J., Bae, Y. C., Choi, S. W., Cho, S. H., Park, R. W., Choi, Y. S., and Lee, W. J. Bone-sparing effect of safflower seeds in ovariectomized rats. Calcified Tissue International (2002) in press
  21. Kim, I. H. Sinyakboncho, Insandongcheon Press, Seoul, pp.567-568, 1992
  22. Kim, J. S., Kang, S. S., Lee, M. W., and Kim, O. K. Isolation of flavonoids from the leaves of Aralia continentalis. Kor. J. Pharmacogn., 26, 239-243 (1995)
  23. Kim, J. H., Jeon, S. M., An, M. Y., Ku, S. K., Lee, J. H., Choi, M. S., and Moon, K. D. Effects of diet of Korean safflower (Carthamus tinctorius L.) seed powder on bone tissue in rats during the recovery of rib fracture. J. Kor. Soc. Food Sci. Nutr., 27, 698-704 (1998)
  24. Kim, H. J., Chung, S. K., and Choi, S. W. Lipoxygenase inhibition and antioxidative activity of flavonoids from the seeds of Paeonia moutan. J. Food Sci. Nutr., 3, 315-319(1998)
  25. Kim, J. H., Jeon, S. M., Park, Y.A., Choi, M. S., and Moon, K. D. Effects of safflower seed (Carthamus tinctorious L.) powder on lipid metabolism in high fat and high cholesterol-fed rats. J. Kor. Soc. Food Sci. Nutr., 28, 625-631 (1999)
  26. Lee, S. J., Yun, Y. S., Lee, I. K., Ryoo, I. J., Yun, B. S., and Yoo, I. D. An antioxidant lignan and other constituents from the root bark of Hibiscus syriacus. Planta Med., 65, 658-660(1999) https://doi.org/10.1055/s-2006-960841
  27. Lowry, O. H., Rosebrough, N. J., Farr, A. C., and Randall, R. J. J. Protein measurements with the folin phenol reagent. J. Biol. Chem., 193,265-275 (1951)
  28. Lu, Y., and Foo, L. Y. Flavonoid and phenolic glycosides from Salvia officinalis. Phytochemistry, 55, 263-267 (2000) https://doi.org/10.1016/S0031-9422(00)00309-5
  29. Markham, K. R., Ternai, B., Stanley, R., Geiger, H., and Mabry, T J. Carbon-13 NMR studies of flavonoids-III: Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron, 34, 1389-1397 (1978) https://doi.org/10.1016/0040-4020(78)88336-7
  30. Markham, K. R., and Geiger, H. $^{1}H$nuclear magnetic resonance spectroscopy of flavonoids and their glycosides in hexadeuterodimethylsulfoxide. In: The flavonoids, Harbome, J.(ed.), Chapman & Hall, London, 1994
  31. Mizuno, M., Kato, M., linuma, K., Tanaka, T., Kimura, A., Ohashi, H., and Sakai, H. Acylated luteolin glucosides from Salix gilgiana. Phytochemistry, 26, 2418-2420 (1987) https://doi.org/10.1016/S0031-9422(00)84739-1
  32. Ohkawa, H., Ohishi, N., and Yagi, K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal. Biochem., 95, 351-358 (1979) https://doi.org/10.1016/0003-2697(79)90738-3
  33. Okigawa, M., Hatanaka, H., Kawano, N., Matsunaga, I., and Tamura, Z. A new glycoside, acacetin-7-glucurono-(1 lead to 2)-glucuronide from the leaves of Clerodendron trichotomum. Tetrahedron Lett., 33, 2935-2936 (1970)
  34. Park, J. J., Park, S. D., Kim, H. J., and Choi, S. W. Quantification and antioxidative properties of flavonoids isolated from safflower (Carthamus tinctorus L.) leaf in relation to different roasting and steamming processing. 11th World Congress of Food Science and Technology, April 22-27, Poster Abstract No. P14-71, Seoul, Korea (2001)
  35. Puppo, A. Effect of flavonoids on hydroxyl radical formation by fenton-type reactions; Influence of the iron chelator. Phytochemisty, 31, 85-88 (1991)
  36. Rios, J. L., Manez, S., Paya, M., and Alcaraz, M. J. Antioxidant activity of flavonoids from Sideritis javalambrensis. Phytochemistry, 31, 1947-1980 (1992) https://doi.org/10.1016/0031-9422(92)80338-F
  37. Roh, J. S., Sun, W.S., Oh, S. U., Lee, J. I., Oh, W. T., and Kim, J. H. In vitro antioxidant activity of safflower (Carthamus tinctorus L.) seeds. Food Sci. Biotechnol., 8, 88-92 (1999)
  38. Saija, A., Scalese, M., Lanza, M., Marzullo, D., Bonina, F., and Castelli, F. Flavonoids as antioxidant agents: importance of their interaction with biomembranes. Free Radical Bio. Med., 19, 481-486 (1995) https://doi.org/10.1016/0891-5849(94)00240-K
  39. Salah, N., Miller, N. J., Paganga, G., Tijburg, L., Bolwell, G. P., and Rice-Evans, C. Polyphenolic flavonoids as scavenger of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys., 2, 339-346 (1995)
  40. SAS Institute, Inc. SAS User's Guide: Statistics, SAS Institute, Inc.: Cary, NC, (1985)
  41. Seo, H. J., Kim, J. H., Kwak, D. Y., Jeon, S. M., Ku, S. K, Lee, J. H., Moon, K. D., and Choi, M. S. The effects of safflower seed powder and its fraction on bone tissue in rib-fractured rats during the recovery. Kor. J. Nutr., 33, 411-420 (2000)
  42. Slater, T. F., and Sawyer, B. C. The stimulatory effects of carbon tetrachloride and other halogenoalkanes on peroxidative reactions in rat liver fractions in vivo. Biochem. J., 123, 805-812(1971) https://doi.org/10.1042/bj1230805
  43. Takii, T., Hayashi, M., Hiroyuki, H., Chiba, T., Kawashima, S., Zhang, H. L., Nagatsu, A., Sakakibara, J., and Onozaki, K. Serotonin derivative, N-(p-coumaroylO serotonin, isolated from safflower (Carthamus tinctorius L.) oil cake augments the proliferation of normal human and mouse fibroblasts in synergy with basic fibroblast growth factor (FGF) or epidermal growth factor(EGF). J. Biochem., 125, 910-915(1999) https://doi.org/10.1093/oxfordjournals.jbchem.a022368
  44. Williams, C. A., and Harborne, J. B. Flavone and flavonol glycosides. In: The Flavonoids, Harborne, J. B. (ed.), Chapman & Hall, London, 1994
  45. Williams, C. A., Greenham, J., and Harborne, J. B. The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae. Biochem. Syst. Ecol., 29, 929-945 (2001) https://doi.org/10.1016/S0305-1978(01)00039-4
  46. Yokozawa, T., Lee, K. I., Kashiwagi, H., Cho, E. J., and Chung, H. Y. Antioxidant activity of herbal teas available on the Korean market. J. Food Sci. Nutr., 4, 92-96 (1999)
  47. Zhang, H. L., Nagatsu, A., Watanabe, T., Sakakibara, J., and Okuyama, H. Antioxidative compounds isolated from safflower (Carthamus tinctorus L.) oil cake. Chem. Pharm. Bull., 45,1910-1914 (1997) https://doi.org/10.1248/cpb.45.1910