Utilization of circular dichroism experiment to distinguish acanthoside D and eleutheroside e
- 주제(키워드) Acanthopanax , Circular dichroism , Configuration , Eucommia , Liriodendrin , Syringaresinol , X-ray crystallography
- 등재 SCIE, KCI등재, SCOPUS
- 발행기관 Pharmaceutical Society of Korea
- 발행년도 2015
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000120454
- 본문언어 영어
- Published As http://dx.doi.org/10.1007/s12272-015-0586-7
- 저작권 이화여자대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
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. © 2015 The Pharmaceutical Society of Korea.
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