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The Pharmaceutical Society of Korea (대한약학회)
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Crystal Structure of Byakangelicin ($C_{17}H_{18}O_{7}$)

  • Kim, Yang-Bae (College of Pharmacy, Seoul National University) ;
  • Oh, Yong-Ho (College of Pharmacy, Seoul National University) ;
  • Park, Il-Yeung (College of Pharmacy, Chungbuk National University) ;
  • Shin, Kuk-Hyun (Natural Products Research Institute, Seoul National University)
  • Published : 2002.06.01
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Abstract

The crystal structure of byakangelicin, one of furanocoumarin aldose reductase inhibitors, was determined by X-ray diffraction method. The crystal is triclinic, with a=8.114(1), b=10.194(1), $c=11.428(1)\AA,{\;}{\alpha}=111.50(1),{\}{\beta}=95.57(1),{\}{\gamma}=112.52(1)^{circ},{\;}D_x=1.41,{\;}D_m=1.39{\;}g/cm^3$, space group P1 and Z=2. The intensity data were collected by ${\omega}-2{\theta}$ scan method with $CuK_{a}$ radiations. The structure was solved by direct method and refined by full matrix least-squares procedure to the final R-value of 0.056. There are two molecules with different conformations in an asymmetric unit. The molecules are kept by two intermolecular O-HO type hydrogen bonds and van der Waal's forces in the crystal. The absolute configuration of the molecules was estimated to S-form by the 'Eta refinement' procedure.

Keywords

References

  1. Aida K., Tawata M., Shindo H., OnayaT., Sasaki H., Yamaguch T., Chin M. and Mitsuhashi H., Isoliquiritigenin; A new aldose reductase inhibitor from Glycyrrhizae Radix. Planta Medica 56,255 (1990)
  2. Beyer-Mears A., Ku L. and Cohen M., Glomerular polyol accumulation in diabetes and its prevention by oral sorbinil. Diabetes 33, 604 (1984) https://doi.org/10.2337/diabetes.33.6.604
  3. Beyer-Mears A. and Cruz E., Reversal of diabetic cataract by sorbinil, an aldose reductase inhibitor. Diabetes 34, 15(1985) https://doi.org/10.2337/diabetes.34.1.15
  4. C. Kay Fair, MolEN, Structure Determination System (1990)
  5. Donald R., On the application of Hamilton's Ratio Test to the Assignment of absolute configuration and an Alternative Test. Acta Cryst. 37(A),734 (1981) https://doi.org/10.1107/S0567739481001629
  6. Dvorric D., Simard-Duguesne N, Krami M., Sestanj K., Gabbay K. H., Kinoshita J. H., Varma S. D. and Merola L. O., Polyol accumulation in galactosemic inhibitor. Science(Wash. D. C.) 182, 1146 (1973) https://doi.org/10.1126/science.182.4117.1146
  7. Engerman R. L. and Kern T. S., Experimental galactosemia produces diabetic-like retinopathy. Diabetes, 33, 97 (1984) https://doi.org/10.2337/diabetes.33.1.97
  8. Enraf Nonius, CAD-4 software. Version 5. Enraf-Nonius, Delft, The Netherlands. (1989)
  9. Fair, C. K., MolEN. An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands.(1990)
  10. Handelsman D. J. and Turtle J. R., Clinical trial of a aldose reductase inhibitor in diabetic neuropathy. Diabetes 30, 459(1931) https://doi.org/10.2337/diabetes.30.6.459
  11. lnaqaki K., Miwa I., Yashiro T. and Okuda J., Inhibition of aldose reductase from rat and bovine lenses by hydantoin derivatives. Chem. Pharm. Bull. 30, 3244 (1982) https://doi.org/10.1248/cpb.30.3244
  12. Johnson C. K., ORTEP, A FORTRAN Thermal Ellipsoid Plot Program for Crystal Structure Illustrations (ORNL-5138). Oak Ridge National University, ennessee (1976)
  13. Kimure Y,, Ohminami H., Arichi H., Okuda H., Baba K., Kozawa M , Arichi S., Effects of various coumarins from roots of Angelica Dahurica on actions of adrenaline, ACTH and insulin fat cells. Planta Med., 45,183 (1982) https://doi.org/10.1055/s-2007-971370
  14. Main P., Germain G. and Woolfson M.M., MULTAN, A Computer Program for Automatic Solution of Crystal Structures from X-ray, Diffraction Data. Univ. of York, England (1976)
  15. Pirie A, and Van Heyningen R., The effect of diabetes on the conent of the sorbitol, glucose, fructose and inositol in the human lens. Exp. Eye Res. 3,124 (1965)
  16. Raskin P. and Rosenstock J., Aldose reductase inhibitors and diabetic complications. AM. J. Med. 83, 298 (1987) https://doi.org/10.1016/0002-9343(87)90702-9
  17. Terashima H., Hama K., Yamamoto R., Tsuboshima M., Kikkawa R., Hatanaka I. and Shigeta Y, Effects of a new aldose reductase inhibitor on various tissues in vitro. J. Pharm. Exp. Ther. 229(1), 226 (1984)
  18. Shimazu M., Ito T., Terashima S., Hayashi T., Arisawa M., Morita N. Kurokawa S., Ito K. and Hashmoto Y., Inhibition of lens aldose reductase by flavonoids. Phytochem. 23, 1885 (1984) https://doi.org/10.1016/S0031-9422(00)84935-3
  19. Sheldrick G.M., SHELX, Program for Crystal Structure Determination, Univ. of Cambridge, England (1976)
  20. Shin, K. H., and Woo, W. S., Inhibition of hepatic microsomal drug-metabolizing enzymes by imperatorin, Arch. Pharm. Res., 9, 81 (1986) https://doi.org/10.1007/BF02857215
  21. Shin, K. H., Kim, Woo, W. S., The mode of the activity of naturally occurring furanocoumarins on hepatic cytochrome P-450 enzyme system. Kor. J. Pharmacogn., 21,74 (1990)
  22. Shin K. H., Chung M. S., Chae Y J., Yoon K. Y and Cho T. S., A survey for aldose reductase inhibition of some herbal medicines. Fitoterapia LXIV(2), 130 (1993a)
  23. Shin K. H., Woo W. S., Moon K. H. and Yoo S. J., Effects of naturally occurring furanocoumarins of lipid peroxidation and carbon tetrachloride-induced hepatotoxicity in mice. Arch. Pharm. Res. 16, 13 (1993b) https://doi.org/10.1007/BF02974121
  24. Shin K. H., Chung M. S., and Cho T. S., Effects of Furanocoumarins from Angelica Dahurica on Aldose Reductase and galactosemic cataract formation in rats. Arch. Pharm. Res. 17,331 (1994) https://doi.org/10.1007/BF02974172
  25. Van Heyningen R., Formation of polyol by the lens of the rat with sugar cataract. Nature, 184, 194 (1959)
  26. Ward J. D., The polyol pathway in the neuropathy of early diabetes. In "Advances in Metabolic Disorders (Suppl.2)" ed. by R. A. Camerini-Davalos and H. S. Cole, Academic Press, New York, p.425 (1973)