Enantiomeric 3-arylcoumarins and 2-arylcoumarones from the roots of Glycyrrhiza uralensis as protein tyrosine phosphatase 1B (PTP1B) inhibitorsElectronic supplementary information (ESI) available. CCDC 1040681, 1040577 and 1040660. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ra06452j

• Main Authors: Ji, Shuai, Qiao, Xue, Li, Zi-wei, Wang, Yong-rui, Yu, Si-wang, Liang, Wen-fei, Lin, Xiong-hao, Ye, Min
• Format: Journal Article
• Language: English
• Published: 19.05.2015
• ISSN: 2046-2069
• DOI: 10.1039/c5ra06452j

Glycyfuranocoumarin A-C ( 1-3 ), three 3-arylcoumarins, and glycyfuranocoumarone A ( 4 ), one 2-arylcoumarone, were isolated in the racemic form from the roots of Glycyrrhiza uralensis . Their structures were elucidated by NMR, 2D NMR and HRESIMS data analyses. All the structures contain a 2,3-dihydro-2,3,3-trimethylbenzofuran ring. Chiral HPLC was used to obtain the optically pure enantiomers, (2′′ R )- 1 and (2′′ S )- 1 . Their absolute configurations were determined by X-ray crystallography. This is the first unambiguous determination of the absolute configuration of 2,3-dihydro-2,3,3-trimethylbenzofurans. (2′′ R )- 1 and (2′′ S )- 1 , as well as 2-4 , exhibited significant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B). Among them, 4 showed an IC 50 of 2.2 μM. Four new PTP1B inhibitors were isolated from Glycyrrhiza uralensis , and the absolute configuration of 2,3-dihydro-2,3,3-trimethylbenzofurans was first unambiguously established.