title: Utilization of circular dichroism experiment to distinguish acanthoside D and eleutheroside E.
abstract: Two lignan glycosides, acanthoside D (1) (=liriodendrin, (+)-syringaresinol di-O-β-D-glucopyranoside) and eleutheroside E (2) have been confused each other for so long time, and hard to be distinguished each other. Now, this two compounds need to be defined properly so that all the commercial mistakes and confusions should not be made. They have identical planar structures except for the configurations at C-7 and C-8 in each structure according to the chemistry database, SciFinder(®). The systematic name of acanthoside D is [(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2,6-dimethoxy-4,1-phenylene) bis-β-D-glucopyranoside (1), and the name of eleutheroside E is [(1R,3aR,4S,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2,6-dimethoxy-4,1-phenylene) bis-β-D-glucopyranoside (2). The differences at two chiral centers do not make any differences in the NMR spectra. Thus, the circular dichroism were utilized to dissolve this difficult problem. Acanthoside D (1) showed a positive Cotton effect at 200 nm, whereas eleutheroside E (2) exhibited a negative cotton effect at 200 nm. The absolute structure of acanthoside D was also confirmed by X-ray crystallography.
authors: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea.
authors: Yun-Seo
authors: YS
authors: Kil
authors: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea.
authors: Ji-Yeon
authors: JY
authors: Park
authors: Department of Chemistry and Nano Science, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea.
authors: Youngmee
authors: Y
authors: Kim
authors: Department of Chemistry and Nano Science, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea.
authors: Sang-Jip
authors: SJ
authors: Nam
authors: Department of Chemistry and Nano Science, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea.
authors: Sung-Jin
authors: SJ
authors: Kim
authors: College of Pharmacy, Seoul National University, Seoul, 156-742, Korea.
authors: Yeong Shik
authors: YS
authors: Kim
authors: College of Pharmacy, Graduate School of Pharmaceutical Sciences, Global Top5 Research Program, Ewha Womans University, Seoul, 120-750, Korea. yuny@ewha.ac.kr.
authors: Eun Kyoung
authors: EK
authors: Seo
mesh_terms: D002942:Circular Dichroism / Q000379:methods*; D018360:Crystallography, X-Ray / Q000379:methods; D005663:Furans / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods
chemical_list: D005663:Furans; D005960:Glucosides; D017705:Lignans; C528660:acanthoside D; C421885:eleutheroside E
keywords: Acanthopanax; Circular dichroism; Configuration; Eucommia; Liriodendrin; Syringaresinol; X-ray crystallography