Browse > Article
http://dx.doi.org/10.5012/bkcs.2009.30.2.415

Absolute Configurations of (±)-Glabridin Enantiomers  

Kim, Mi-Hyang (Program in Applied Life Chemistry, Department of Agricultural Biotechnology and Research Institute for Agriculture and Life Sciences, Seoul National University)
Kim, Soo-Un (Program in Applied Life Chemistry, Department of Agricultural Biotechnology and Research Institute for Agriculture and Life Sciences, Seoul National University)
Kim, Yong-Ung (Department of Herbal Pharmaceutical Engineering, Daegu Haany University)
Han, Jae-Hong (Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.2, 2009 , pp. 415-418 More about this Journal
Abstract
Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (${\pm}$)-glabridin enantiomers were studied with synthetic glabridin. Synthetic glabridin enantiomers were separated by semi-preparative Sumi-chiral column chromatography, and characterized by UV-Vis and NMR spectroscopy. Three-dimensional molecular structure of glabridin was obtained as equatorial Ph-3 half chair chroman ring from semi-empirical PM3 calculation, and refined by coupling constants in $^1H$ NMR spectrum. Finally, absolute configurations of two enantiomers were determined by circular dichroism spectroscopy based on the empirical helicity rules. Absolute configuration of natural (+)-glabridin was confirmed as (R)-glabridin, as known.
Keywords
Absolute configuration; Circular dichroism (CD); Flavonoids; Glabridin; Isoflavan;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
연도 인용수 순위
1 Dixon, R. A.; Sumner, L. W. Plant Physiol. 2003, 131, 878- 885.   DOI   ScienceOn
2 Jung, S.-H.; Cho, S.-H.; Dang, T.-H.; Lee, J.-H.; Ju, J.-H.; Kim, M.-K.; Lee, S.-H.; Ryu, J.-C.; Kim, Y. Eur. J. Med. Chem. 2003, 38, 537-545.   DOI   ScienceOn
3 Slade, D.; Ferreira, D.; Marais, J. P. J. Phytochemistry 2005, 66, 2177-2215.   DOI   ScienceOn
4 Won, D.; Shin, B.-K.; Han, J. J. Appl. Biol. Chem. 2008, 51, 17-19.
5 Won, D.; Shin, B.-K.; Kang, S.; Hur, H.-G.; Kim, M.; Han, J. Bioorg. Med. Chem. Lett. 2008, 18, 1952-1957.   DOI   ScienceOn
6 Fukai, T.; Marumo, A.; Kaitou, K.; Kanda, T.; Terada, S.; Nomura, T. Life Sciences 2002, 71, 1449-1463.   DOI   ScienceOn
7 Somjen, D.; Knoll, E.; Vaya, J.; Stern, N.; Tamir, S. J. Steroid Biochem. Mol. Biol. 2004, 91, 147-155.   DOI   ScienceOn
8 Kang, J. S.; Yoon, Y. D.; Cho, I. J.; Han, M. H.; Lee, C. W.; Park, S.-K.; Kim, H. M. J. Pharmacol. Exp. Ther. 2005, 312, 1187-1194.   DOI   ScienceOn
9 Somjen, D.; Katzburg, S.; Vaya, J.; Kaye, A. M.; Hendel, D.;Posner, G. H.; Tamir, S. J. Steroid Biochem. Mol. Biol. 2004, 91, 241-246.   DOI   ScienceOn
10 Choi, E.-M. Biochem. Pharmacol. 2005, 70, 363-368.   DOI   ScienceOn
11 Shin, B.-K.; Kim, H. M.; Lee, S.; Han, J. Bull. Korean Chem. Soc. 2008, 29, 1572-1574.   DOI   ScienceOn
12 Magee, P. J.; Raschke, M.; Steiner, C.; Duffin, J. G.; Pool-Zobel, B. L.; Jokela, T.; Wahala, K.; Rowland, I. R. Nutr. Cancer 2006, 54, 232-242.   DOI   ScienceOn
13 Muthyala, R. S.; Ju, Y. H.; Sheng, S.; Williams, L. D.; Doerge, D. R.; Katzenellenbogen, B. S.; Helferich, W. G.; Katzenellenbogen, J. A. Bioorg. Med. Chem. 2004, 12, 1559-1567.   DOI   ScienceOn
14 Frase, R. R. In Asymmetric Synthesis Morrison, J. D., Ed.; Academic New York, 1983 Vol. 1, Chap. 9.
15 Tamir, S.; Eizenberg, M.; Somjen, D.; Stern, N.; Shelach, R.;Kaye, A.; Vaya, J. Cancer Res. 2000, 60, 5704-5709.
16 Gawronski, J. K.; Kwit, M.; Boyd, D. R.; Sharma, N. D.; Malone, J. F.; Drake, A. F. J. Am. Chem. Soc. 2005, 127, 4308-4319.   DOI   ScienceOn
17 Snatzke, G.; Znatzke, F.; Tökés, A. L.; Rákosi, M.; Bognár, R. Tetrahderon 1973, 29, 909-912.   DOI   ScienceOn
18 Gupta, V. K.; Fatima, A.; Faridi, U.; Negi, A. S.; Shanker, K.; Kumar, J. K.; Rahuja, N.; Luqman, S.; Sisodia, B. S.; Saikia, D.; Darokar, M.P.; Khanuja, P. S. J. Ethnopharmacol. 2008, 116, 377-380.   DOI   ScienceOn
19 Fukai, T.; Satoh, K.; Nomura, T.; Sakagami, H. Fitoterapia 2003, 74, 720-724.   DOI   ScienceOn
20 Yu, X.-Q.; Xue, C. C.; Zhou, Z.-W.; Li, C.-G.; Du, Y.-M.; Liang, J.; Zhou, S.-F. Life Sciences 2008, 82, 68-78.   DOI   ScienceOn
21 Fuhrman, B.; Buch, S.; Vaya, J.; Belinky, P. A.; Coleman, R.;Hayek, T.; Aviram, M. Am. J. Clin. Nutr. 1997, 66, 267-275.
22 Fuhrman, B.; Volkova, N.; Aviram, M. Atherosclerosis 2002, 161, 307-316.   DOI   ScienceOn
23 Kurosawa, K.; Ollis, W. D.; Redman, B. T.; Sutherland, I. O.;Gottlieb, O. R.; Alves, H. M. Chem. Comm. 1968, 1265-1267.
24 Kent, U. M.; Aviram, M.; Rosenblat, M.; Hollenberg, P. F. Drug Metab. Dispos. 2002, 30, 709-715.   DOI   ScienceOn
25 Tsukamoto, S.; Aburatani, M.; Yoshida, T.; Yamashita, Y.;El-Beih, A. A.; Ohta, T. Biol. Pharm. Bull. 2005, 28, 2000-2002.   DOI   ScienceOn
26 Saitoh, T.; Kinoshita, T.; Shibata, S. Chem. Pharm. Bull. 1976, 24, 752-755.   DOI
27 Kurosawa, K.; Ollis, W. D.; Redman, B. T.; Sutherland, I. O.;Alves, H. M.; Gottlieb, O. R. Phytochemistry 1978, 17, 1423- 1426.   DOI   ScienceOn
28 Yoo, S.-K.; Nahm, K. Bull. Korean Chem. Soc. 2007, 28, 481-484.   DOI   ScienceOn
29 Shin, B.-K.; Han, J. Bull. Korean Chem. Soc. 2008, 29, 2299- 2302.   DOI   ScienceOn
30 Kinoshita, T.; Kajiyama, K.; Hiraga, Y.; Takahashi, K.; Tamura, Y.; Mizutani, K. Heterocycles 1996, 43, 581-588.   DOI   ScienceOn
31 Versteeg, M.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron 1999, 55, 3365-3376.   DOI   ScienceOn
32 Pachler, K. G. R. Tetrahedron 1971, 27, 187-199.   DOI   ScienceOn
33 Crabbé, P. In Topics in Stereochemistry; Allinger, N. L.; Eliel, E. L., Eds.; Wiley: New York, 1967; Vol. 1, pp 93-185.