Absolute Configurations of ( /-)-Glabridin Enantiomers

作者：Kim Mihyang; Kim Soo Un; Kim Yong ung; Han Jaehong^*

来源：Bulletin of the Korean Chemical Society, 2009, 30(2): 415-418.

DOI：10.5012/bkcs.2009.30.2.415

• Absolute configuration
• Circular dichroism (CD)
• Flavonoids
• Glabridin
• Isoflavan

Concerned with ambiguous stereochemistry assignment of natural ( )-glabridin, absolute configurations of ( /-)-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 (1)H 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.

• 出版日期2009-2-20