Anti-oxidant Compounds of Cudrania tricuspidata Leaves

구지뽕나무 잎의 항산화 성분

  • Published : 2005.10.01

Abstract

Cudrania tricuspidata Bereau (Moraceae) have been used for anti-inflammatory, anti-hepatotoxic, anti-hyper­tensive and anti-diabetic activities. In order to investigate the efficacy of antioxidant activity, the bio-activity guided fraction and isolation of Biologically active substance were performed. $H_{2}O,\;30\%,\;60\%,\;100%$ MeOH and acetone fractions were examined on the antioxidant activity by DPPH method. It was shown that $30\%,\;60\%,\;100\%$ MeOH fractions have sig­nificantly antioxidant activity. From $30\%$ MeOH fraction, two dihydroflavonoid glycosides dihydroquercetin 7-O-$\beta$-D-glu­copyranoside (I), dihydrokaempferol 7-O-$\beta$-D-glucopyranoside (V) were isolated and $60\%$ MeOH fraction, six flavonoids including quercetin 3-O-$\alpha$-L-rhamnopyranosyl($1\rightarrow6$)-$\beta$-D-glucopyranoside (II), quercetin 3-O-$\beta$-D-glucopyranoside (III), quercetin 7-O-$\beta$-D-glucopyranoside (IV), kaempferol 3-O-$\alpha$-L-rhamnopyranosyl($1\rightarrow6$)-$\beta$-D-glucopyranoside (VI), kaempferol 3-O-$\beta$-D-glucopyranoside (VII), kaempferol 7-O-$\beta$-D-glucopyranoside (VIII) were isolated. To investigate the antioxidant activities of each compounds, we measured radical scavening activity with DPPH method and anti-lipid per­oxidative efficacy on low density lipoprotein (LDL) with TBARS assay. Four compounds of quercetin glycosides (I, II, III, IV) showed significant antioxidant activity.

Keywords

References

  1. 강소 신의학원 : 중약 대사전, 소학관 2, 2383 (1985)
  2. 문화방송 : 한국 민간요법대전, 금박출판사, 서울, p. 31 (1987)
  3. 堀田滿 : 世界有用植物事典(植物編), 平凡社, p. 341 (1989)
  4. 김창민, 신민교, 안덕균, 이경순 : 중약대사전, 정담출판사 8, 4585 (1998)
  5. Lee, B. W., Gal, S. W., Park, K. M. and Park, K. H. : Cytotoxic xanthones from Cudrania tricuspidata. J. Nat. Prod. 68, 456 (2005) https://doi.org/10.1021/np030481a
  6. Zou, Y. S., Hou, A. J., Zhu, G. F., Chen, Y. F., Sun, H. D. and Zhao, O. S. : Cytotoxic isoprenylated xanthones from Cudrania tricuspidate, Bioorg Med. Chem. 15(12), 1947 (2004)
  7. Han, S. Y., Park, J. H., Park, H. J. and Choi, J. S. : Chemical study on the stem of Cudrania tricuspidata. Arch. Pharm. Res. 12, 39 (1989) https://doi.org/10.1007/BF02855744
  8. Lee, I. K., Kim, C. J., Song, K. S., Kim, W. M. and Yoo, I. D. : Two benzylated dihydroflavonols from Cudrania tricuspidaia. J. Nat. Prod. 58, 1614 (1995) https://doi.org/10.1021/np50124a024
  9. Lee, I. K., Kim, C. J., Song, K. S., Kim, W. M., Koshino, H., Uramoto, M. and Yoo, I. D. : Cytotoxic benzyl dihydroflavonols from Cudrania tricuspidata. Phytochemistry 41, 213 (1996) https://doi.org/10.1016/0031-9422(95)00609-5
  10. Chang, C. H., Lin, C. C., Hattory, M. and Namba, T. : Fourprenylated xanthones from Cudrania cochinchinensis. Phytochemistry 28, 595 (1989) https://doi.org/10.1016/0031-9422(89)80058-5
  11. Hou, A., Fukai. T., Shimazaki, M., Sskagami, H., Sun, H. and Nomura, T. : Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis. J. Nat. Prod. 64, 65 (2001) https://doi.org/10.1021/np000589f
  12. Chang, C. H., Lin, C. C., Hattori, M. and Namba, T. : Effects on anti-lipid peroxidation of Cudrania cochinchinensis var. gerontogea. J. Ethnophamacol. 44, 79 (1994) https://doi.org/10.1016/0378-8741(94)90072-8
  13. Lin, C. C., Lee, H. Y., Chang, C. H. and Yang, J. J. : The anti-inflammatory and hepatoprotective effects of fractions from Cudrania cochinchinensis var.gerontogea. Am J. Chin. Med. 27, 227 (1999) https://doi.org/10.1142/S0192415X99000264
  14. Seo, W. G., Pae, H. O., Oh, G. S., Chai, K. Y., Yun, Y. G., Kwon, T. O. and Chung, H. T. : Inhibitory effect of ethyl acetate fraction from Cudrania tricuspidata on the expression of nitric oxide synthase gene in RAW 264.7 macrophages stimulated with interferon-gamma and lipopolysaccharide. Gen. Pharmacol. 35, 21 (2000) https://doi.org/10.1016/S0306-3623(01)00086-6
  15. Seo, W. G., Pae, H. O., Oh, G. S., Chai, K. Y., Yun, Y. G., Chung, H. T., Jang, K. K. and Kwon, T. O. : Ethyl acetate extract of the stem bark of Cudrania tricuspidate induces apoptosis in human leukemia HL-60 cells. Am. J. Chin. Med. 29, 313 (2001) https://doi.org/10.1142/S0192415X01000332
  16. Kang, D. G., Hur, T. Y., Lee, G. M., Oh, H., Kwon, T. O., Sohn, E. J. and Lee, H. S. : Effect of Cudrania tricuspidata water extract on blood presure and renal functions in NO-dependent hypertention, 대한신장학회, 촌계학술대회 초록집 p. 280 (2001)
  17. Park, W. Y., Ro, J. S. and Lee, K. S. : Hypoglycemic effect of Cudrania tricuspidate root bark. Kor. J. Pharmacogn 32, 248-252 (2001)
  18. Cho, E. J., Yokozawa, T., Rhyu, D. Y., Kim, H. Y., Shibahara, N. and Park, J. C. : The inhibitory effects of 12 medicinal plants and their component compounds on lipid peroxidation. Am. J. Chin. Med. 31, 907 (2003) https://doi.org/10.1142/S0192415X03001648
  19. Cho, E. J., Yokozawa, T., Rhyu, D. Y., Kim, S. C., Shibahara, N. and Park, J. C. : Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical. Phytomedicine. 10, 544 (2003) https://doi.org/10.1078/094471103322331520
  20. 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
  21. Inkeda, N. and Fukuzume, K. : Tocopherols as antioxidants in oxidation of methyl linolate. J. Japan Oil Chem. Soc. 26, 343 (1977) https://doi.org/10.5650/jos1956.26.343