Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Constituents of the Roots of Pueraria Iobata Inhibit Formation of Advanced Glycation End Products (AGEs)

  • Kim, Jong-Min (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Lee, Yun-Mi (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Lee, Ga-Young (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Jang, Dae-Sik (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University) ;
  • Kim, Jin-Sook (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine)
  • Published : 2006.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

Two isoflavone C-glucosides, puerarin (1) and PG-3 (2), a but-2-enolide, $({\pm})-puerol$ B (3), two isoflavone O-glucosides, daidzin (4) and genistin (5), and three pterocarpans, (-)-medicarpin (6), (-)-glycinol (7) and (-)-tuberosin (8), were isolated from a MeOH extract of the roots of Pueraria Iobata, using an in vitro bioassay based on the inhibition of the formation of advanced glycation end products (AGEs) to monitor chromatographic fractionation. The structures of 1-8 were determined by spectroscopic data interpretation, particularly by 1D- and 2D-NMR studies, and by comparison of these data with values in the literature. All of the isolates (1-8) were evaluated for their inhibitory activity on AGEs formation in vitro. Of these, puerarin (1), PG-3 (2), and $({\pm})-puerol$ B (3) exhibited more potent inhibitory activity than the positive control aminoguanidine.

Keywords

References

  1. Bae, K. H., Medicinal Plants of Korea. Kyo-Hak Publishing Co., Seoul, p 260, (2000)
  2. Bucala, R. and Vlassara, H., Advanced glycosylation end products in diabetic renal and vascular disease. Am. J. Kidney Dis., 26, 875-888 (1995) https://doi.org/10.1016/0272-6386(95)90051-9
  3. Forbes, J. M., Cooper, M. E., Oldfield, M. D., and Thomas, M. C., Role of advanced glycation end products in diabetic nephropathy. J. Am. Soc. Nephrol., 14, S254-S258 (2003) https://doi.org/10.1097/01.ASN.0000077413.41276.17
  4. Kalousova, M., Zima, T., Tesar, V., Stipek, S., and Sulkova, S., Advanced glycation end products in clinical nephrology. Kidney Blood Press Res., 27, 18-28 (2004) https://doi.org/10.1159/000075533
  5. Kim, J. S., Kim, H., and Ko, J. H., Studies on the processing of herbal medicines (III)-HPLC analysis of magnolol and inhibitory effects on the formation of advanced glycation endproducts (AGEs) in vitro of unprocessed and processed Magnolia Bark. Kor. J. Pharmacogn., 33, 308-311 (2002)
  6. Kinjo, J. -E., Furusawa, J. -I., Baba, J., Takeshita, T., Yamasaki, M., and Nohara, T., Studies on the constituents of Pueraria lobota. III. Isoflavonoids and related compounds in the roots and the voluble stems. Chem. Pharm. Bull., 35, 4846-4850 (1987) https://doi.org/10.1248/cpb.35.4846
  7. Larkins, R. G. and Dunlop, M. E., The link between hyperglycemia and diabetic nephropathy. Diabetologia, 35, 499- 504 (1992) https://doi.org/10.1007/BF00400475
  8. Lee, S. J., Baek, H. J., Lee, C. H., and Kim, H. P., Antiinflammatory activity of isoflavonoids from Pueraria Radix and biochanin A derivatives. Arch. Pharm. Res., 17, 31-35 (1994) https://doi.org/10.1007/BF02978244
  9. Lyne, R. L. and Mulheirn, L. J., Minor pterocarpinoids of soybean. Tetrahedron lett., 19, 3127-3128 (1978) https://doi.org/10.1016/S0040-4039(01)94961-5
  10. Makita, Z., Radoff, S., Rayfield, E. J., Yang, Z. H., Skolnik, E., Delaney, V., Friedman, E. A., Cerami, A., and Vlassara, H. N., Advanced glycosylation end products in patients with diabetic nephropathy. N. Eng. J. Med., 325, 836-842 (1993) https://doi.org/10.1056/NEJM199109193251202
  11. Matsuda, H., Wang, T., Managi, H., and Yoshikawa, M., Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. Bioorg. Med. Chem., 11, 5317-5323 (2003) https://doi.org/10.1016/j.bmc.2003.09.045
  12. Nohara, T., Kinjo, J., Furusawa, J., Sakai, Y., Inoue, M., Shirataki, Y., Ishibashi, Y., Yokoe, I., and Komatsu, M., But-2- enolides from Pueraria lobota and revised structures of puerosides A, B and sophoroside A. Phytochemistry, 33, 1207-1210 (1993) https://doi.org/10.1016/0031-9422(93)85050-2
  13. Ohshima, Y., Okuyama,T., Takahashi, K., Takizawa, T., and Shibata, S., Isolation and high performance liquid chromatography (HPLC) of isoflavonoids from the Pueraria root. Planta Med., 54, 250-254 (1988) https://doi.org/10.1055/s-2006-962420
  14. Pickup, J. C. and Williams, G., Textbook of Diabetes 2, In Taguchi, T. and Brownlee, M. (Eds.). The biochemical mechanisms of diabetic tissue damage. Blackwell Science, Massachusetts, pp. 47.1-47.17, (2003)
  15. Ren, P., Hu, H., and Zhang, R., Observation on efficacy of puerarin in treating diabetic retinopathy. Zhongquo Zhong Xi Yi Jie He Zo Zhi, 20, 574-576 (2000)
  16. Shinohara, R., Mano, T., Nagasaka, A., Sawai, Y., Uchimura, K., Hayashi, R., Hayakawa, N., Nagata, M., Makino, M., Kakizawa, H., Itoh, Y., Nakai, A., and Itoh, M., Effects of thyroid hormone on the sorbitol pathway in streptozotocininduced diabetic rats. Biochim. Biophys. Acta, 1425, 577-586 (1998) https://doi.org/10.1016/S0304-4165(98)00111-1
  17. Shirataki, Y., Tsuzuku, T., Yokoe, I., Hirano, R., and Komatsu, M., Studies on the constituents of Sophora species. XXIII. Constituents of the root of Sophora chrysophylla SEEM. (1). Chem. Pharm. Bull., 38, 1712-1716 (1990) https://doi.org/10.1248/cpb.38.1712
  18. Vinson, J. A. and Howard III, T. B., Inhibition of protein glycation and advanced glycation end products by ascorbic acid and other vitamins and nutrients. J. Nutr. Biochem., 7, 659-663 (1996) https://doi.org/10.1016/S0955-2863(96)00128-3
  19. Yokozawa, T., Nakagawa, T., and Terasawa, K., Effects of Oriental medicines on the production of advanced glycation endproducts. J. Trad. Med., 18, 107-112 (2001)
  20. Yoon, J. S., Sung, S. H., Park, J. H., and Kim, Y. C., Flavonoids from Spatholobus suberectus. Arch. Pharm. Res., 27, 589-592 (2004) https://doi.org/10.1007/BF02980154