Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities.
Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 microM, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode.
Li
Songpei
S
Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.
Li
Wei
W
Wang
Yinghua
Y
Asada
Yoshihisa
Y
Koike
Kazuo
K
D003924:Diabetes Mellitus, Type 2 / Q000188:drug therapy; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D029882:Glycyrrhiza uralensis / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D013329:Structure-Activity Relationship
D005419:Flavonoids; D010936:Plant Extracts; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1