Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B

• Published in: Bioorganic & medicinal chemistry letters 2007-07, Vol.17 (14), p.3868-3871
• Main Authors: Na, MinKyun, Hoang, Duc Manh, Njamen, Dieudonné, Mbafor, Joseph Tanyi, Fomum, Zacharias Tanee, Thuong, Phuong Thien, Ahn, Jong Seog, Oh, Won Keun
• Format: Article
• Language: English
• Subjects: 2-Arylbenzofuran derivatives; Benzofurans - isolation & purification; Benzofurans - pharmacology; Biological and medical sciences; Erythrina; Erythrina - enzymology; Erythrina addisoniae; General pharmacology; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Prenyl group; Protein Tyrosine Phosphatase, Non-Receptor Type 6 - antagonists & inhibitors; Protein tyrosine phosphatase-1B (PTP1B); Spectrum Analysis - methods
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2007.05.005

Three new ( 1– 3) and three known ( 4– 6) 2-arylbenzofuran derivatives were isolated from the stem bark of Erythrina addisoniae. The new compounds 1– 3 were found to strongly inhibit PTP1B activity in vitro. Bioassay-guided fractionation of an EtOAc-soluble extract of the stem bark of Erythrina addisoniae (Leguminosae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three new ( 1– 3) and three known ( 4– 6) 2-arylbenzofuran derivatives. The new compounds were identified as 2-[2′,4′-dihydroxy-3′-(3-methylbut-2-enyl)phenyl]-6-hydroxybenzofuran ( 1), 2-[2′-methoxy-4′-hydroxy-5′-(3-methylbut-2-enyl)phenyl]-6-hydroxybenzofuran ( 2), and 2-(2′-methoxy-4′-hydroxyphenyl)-5-(3-methylbut-2-enyl)-6-hydroxybenzofuran ( 3). The new 2-arylbenzofurans 1– 3 inhibited PTP1B activity with IC 50 values ranging from 13.6 ± 1.1 to 17.5 ± 1.2 μM in vitro assay. On the basis of the data obtained, 2-arylbenzofurans with prenyl group may be considered as a new class of PTP1B inhibitors.