Pterocarpans with inhibitory effects on protein tyrosine phosphatase 1B from Erythrina lysistemon Hutch

TY - JOUR

T1 - Pterocarpans with inhibitory effects on protein tyrosine phosphatase 1B from Erythrina lysistemon Hutch

AU - Dao, Trong Tuan

AU - Nguyen, Phi Hung

AU - Thuong, Phuong Thien

AU - Kang, Keon Wook

AU - Na, MinKyun

AU - Ndinteh, Derek Tantoh

AU - Mbafor, Joseph Tanyi

AU - Oh, Won Keun

PY - 2009/12

Y1 - 2009/12

N2 - Bioassay-guided fractionation of the MeOH extract of the stem bark of Erythrina lysistemon Hutch. resulted in isolation of pterocarpans (1-3), named erylysins A-C, along with nine known pterocarpans (4-12). Their structures were determined to be 3''-hydroxy-2',2'-dimethylpyrano[6',5':3,4]-2'',2''-dimethyldihydropyrano[6'',5'':9,10]pterocarpan (1), furano[5',4':3,4]-9-hydroxy-10-prenylpterocarpan (2), and 8-formyl-3,9-dihydroxy-4,10-diprenylpterocarpan (3), based on spectroscopic analyses. All the isolates, with the exception of 3, 6, and 11, strongly inhibited protein tyrosine phosphatase 1B (PTP1B) activity in an in vitro assay, with IC(50) values ranging from 1.01+/-0.3 to 18.1+/-0.9 microg/mL. This is the first report showing the potential of prenylated pterocarpans as a class of natural PTP1B inhibitors.

AB - Bioassay-guided fractionation of the MeOH extract of the stem bark of Erythrina lysistemon Hutch. resulted in isolation of pterocarpans (1-3), named erylysins A-C, along with nine known pterocarpans (4-12). Their structures were determined to be 3''-hydroxy-2',2'-dimethylpyrano[6',5':3,4]-2'',2''-dimethyldihydropyrano[6'',5'':9,10]pterocarpan (1), furano[5',4':3,4]-9-hydroxy-10-prenylpterocarpan (2), and 8-formyl-3,9-dihydroxy-4,10-diprenylpterocarpan (3), based on spectroscopic analyses. All the isolates, with the exception of 3, 6, and 11, strongly inhibited protein tyrosine phosphatase 1B (PTP1B) activity in an in vitro assay, with IC(50) values ranging from 1.01+/-0.3 to 18.1+/-0.9 microg/mL. This is the first report showing the potential of prenylated pterocarpans as a class of natural PTP1B inhibitors.

KW - Enzyme Inhibitors

KW - Erythrina

KW - Plant Bark

KW - Plant Extracts

KW - Plant Stems

KW - Prenylation

KW - Protein Tyrosine Phosphatase, Non-Receptor Type 1

KW - Pterocarpans

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1016/j.phytochem.2009.09.012

DO - 10.1016/j.phytochem.2009.09.012

M3 - Journal article

C2 - 19833362

SN - 0031-9422

VL - 70

SP - 2053

EP - 2057

JO - Phytochemistry

JF - Phytochemistry

IS - 17-18

ER -