Browse > Article

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)
Publication Information
Archives of Pharmacal Research / v.29, no.7, 2006 , pp. 587-590 More about this Journal
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
Cassia tora; Leguminosae; Cassiaside; $Rubrofusarin-6-O-{\beta}-D-gentiobioside$; $Toralactone-9-O-{\beta}-D-gentiobioside$; Advanced glycation end products (AGEs); Diabetic complications;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 15  (Related Records In Web of Science)
Times Cited By SCOPUS : 10
연도 인용수 순위
1 Bucala, R. and Vlassara, H., Advanced glycosylation end products in diabetic renal and vascular disease. Am. J. Kidney Dis., 26, 875-888 (1995)   DOI   ScienceOn
2 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)   DOI   ScienceOn
3 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)   DOI   ScienceOn
4 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)   DOI
5 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)   DOI   ScienceOn
6 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)   DOI   ScienceOn
7 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)   DOI   ScienceOn
8 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)   DOI   ScienceOn
9 Namba, T., Colored Illustrations of Wakan-Yaku. Hoi-kusha Publishing Co. Ltd., Vol. 1. pp. 226 (1980)
10 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)   DOI   ScienceOn
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)   DOI   ScienceOn
12 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)   DOI   ScienceOn
13 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)   과학기술학회마을
14 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)   DOI   ScienceOn
15 Larkins, R. G. and Dunlop, M. E., The link between hyperglycaemia and diabetic nephropathy. Diabetologia, 35, 499- 504 (1992)   DOI
16 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)   DOI
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)   DOI   ScienceOn
18 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)
19 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)   DOI   ScienceOn