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Absolute configuration of antifibrotic (+)-episesamin isolated from Lindera obtusiloba BLUME.
- Source :
-
Zeitschrift fur Naturforschung. C, Journal of biosciences [Z Naturforsch C J Biosci] 2011 Sep-Oct; Vol. 66 (9-10), pp. 460-4. - Publication Year :
- 2011
-
Abstract
- Fractionation of a 70% ethanolic extract from twigs of Lindera obtusiloba BLUME (Japanese spicebush, Tohaku) yielded five fractions of different polarity. The antifibrotic activity within the chloroform phase was best assessed by an in vitro bioassay using rat hepatic stellate cell (HSC) proliferation and their autocrine transforming growth factor beta (TGF-beta) expression as sensitive fibrosis-associated read out. Chromatography of the chloroform extract on Sephadex LH-20 or liquid-liquid extractions yielded a crystalline compound as an active principle, which was identified from NMR and ESI-MS analyses, its melting point, and its optical rotation as (7S,7'R,8R,8'R)-3,4:3',4'-bis(methylenedioxy)-7,9':7',9-diepoxy-lignane [(+)-episesamin]. X-Ray diffraction confirmed the structure and provided, for the first time, directly its absolute configuration. (+)-Episesamin blocked proliferation and the profibrotic autocrine TGF-beta expression HSC without significant cytotoxicity.
- Subjects :
- Cells, Cultured
Dioxoles isolation & purification
Dioxoles pharmacology
Lignans isolation & purification
Lignans pharmacology
Magnetic Resonance Spectroscopy
Models, Molecular
Spectrometry, Mass, Electrospray Ionization
Dioxoles chemistry
Fibrosis prevention & control
Lignans chemistry
Lindera chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 0939-5075
- Volume :
- 66
- Issue :
- 9-10
- Database :
- MEDLINE
- Journal :
- Zeitschrift fur Naturforschung. C, Journal of biosciences
- Publication Type :
- Academic Journal
- Accession number :
- 22191210
- Full Text :
- https://doi.org/10.1515/znc-2011-9-1004