Naphthopyrone Glucosides from the Seeds of Cassia tora with Inhibitory Activity on Advanced Glycation End Products (AGEs) Formation

  • 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) ;
  • Lee, Yun-Mi (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Kim, Jong-Min (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Kim, Jin-Sook (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine)
  • Published : 2006.07.01

Abstract

Three naphthopyrone glucosides, cassiaside (1), $rubrofusarin-6-O-{\beta}-D-gentiobioside$ (2), and $toralactone-9-O-{\beta}-D-gentiobioside$ (3), were isolated from the BuOH-soluble extract of the seeds of Cassia tora as active constituents, using an in vitro bioassay based on the inhibition of advanced glycation end products (AGEs) to monitor chromatographic fractionation. The structures of 1-3 were determined by spectroscopic data interpretation, particularly by extensive 1D and 2D NMR studies. All the isolates (1-3) were evaluated for the inhibitory activity on AGEs formation in vitro.

Keywords

References

  1. 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
  2. Choi, J. S., Lee, H. J., and Kang, S. S., Alaternin, cassiaside and rubrofusarin gentiobioside, radical scavenging principles from the seeds of Cassia tora on 1,1-diphenyl-2-prcrylhydrazyl (DPPH) radical. Arch. Pharm. Res., 17, 462-466 (1994) https://doi.org/10.1007/BF02979126
  3. Choi, J. S., Lee, H. J., Park, K. Y., Jung, G. O., and Kang, S. S., In vitro antimutagenic effects of naphthopyrone glycosides from Cassia tora. Planta Med., 64, 100-104 (1998)
  4. Choi, J. S., Lee, H. J., Park, K. Y., Jung, G. O., and Kang, S. S., In vitro antimutagenic effects of anthraquinone aglycones and naphthopyrone glycosides from Cassia tora. Planta Med., 63, 11-14 (1997) https://doi.org/10.1055/s-2006-957593
  5. 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
  6. Hatano, T., Uebayashi, H., Ito, H., Shiota, S., Tsuchiya, T., and Yoshida, T., Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem. Pharm. Bull., 47, 1121-1127 (1999) https://doi.org/10.1248/cpb.47.1121
  7. 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
  8. 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)
  9. Kim, Y. M., Lee, C. H., Kim, H. G., and Lee, H. S., Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi. J. Agric. Food Chem., 52, 6096-6100 (2004) https://doi.org/10.1021/jf049379p
  10. Larkins, R. G. and Dunlop, M. E., The link between hyperglycaemia and diabetic nephropathy. Diabetologia, 35, 499- 504 (1992) https://doi.org/10.1007/BF00400475
  11. 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
  12. 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
  13. Namba, T., Colored Illustrations of Wakan-Yaku. Hoi-kusha Publishing Co. Ltd., Vol. 1. pp. 226 (1980)
  14. 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
  15. The Diabetes Control and Complication Trial Research Group, The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus. N. Engl. J. Med., 329, 977-986 (1993) https://doi.org/10.1056/NEJM199309303291401
  16. 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
  17. Wong, S. M., Wong, M. M., Seligmann, O., and Wagner, H., Anthraquinone glycosides from the seeds of Cassia tora. Phytochemistry, 28, 211-214 (1989a) https://doi.org/10.1016/0031-9422(89)85040-X
  18. Wong, S. M., Wong, M. M., Seligmann, O., and Wagner, H., New antihepatotoxic naphtho-pyrone glycosides from the seeds of Cassia tora. Planta Med., 55, 276-280 (1989b) https://doi.org/10.1055/s-2006-962003
  19. Zhang, Z. and Yu, B., Total synthesis of the antiallergic naphtho- ${\alpha}$-pyrone tetraglucoside, cassiaside C2, isolated from Cassia seeds. J. Org. Chem., 68, 6309-6313 (2003) https://doi.org/10.1021/jo034223u