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Protein Tyrosine Phosphatase-1B Inhibitory Activity of Isoprenylated Flavonoids Isolated from Erythrina mildbraedii

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Korea Research Institute of Bioscience and Biotechnology (KRIBB), 52 Eoun-dong, Yuseong-gu, Daejeon 305-333, Korea, Department of Animal Biology and Physiology, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon, and Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon
Cite this: J. Nat. Prod. 2006, 69, 11, 1572–1576
Publication Date (Web):October 21, 2006
https://doi.org/10.1021/np0601861
Copyright © 2006 American Chemical Society and American Society of Pharmacognosy

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    Abstract

    Abstract Image

    Inhibition of protein tyrosine phosphatase-1B (PTP1B) has been proposed as a therapy for treatment of type-2 diabetes and obesity. Bioassay-guided fractionation of an EtOAc-soluble extract of the root bark of Erythrina mildbraedii, using an in vitro PTP1B inhibitory assay, resulted in the isolation of three new isoprenylated flavonoids, abyssinone-IV-4‘-O-methyl ether (2), 7-hydroxy-4‘-methoxy-3‘-(3-hydroxy-3-methyl-trans-but-1-enyl)-5‘-(3-methylbut-2-enyl)flavanone (3), and abyssinone-VI-4-O-methyl ether (6), along with six known flavonoids, abyssinone-V-4‘-O-methyl ether (1), abyssinone-V (4), abyssinone-IV (5), sigmoidin E (7), 4‘-hydroxy-5,7-dimethoxyisoflavone (8), and alpinumisoflavone (9). Compounds 1 and 2, 47, and 9 inhibited PTP1B activity, with IC50 values ranging from 14.8 ± 1.1 to 39.7 ± 2.5 μM. On the basis of the data obtained, flavanones and chalcones with isoprenyl groups may be considered as a new class of PTP1B inhibitors.

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     Part 48 in the series “Erythrina Studies”.

     KRIBB.

     Department of Animal Biology and Physiology, University of Yaoundé I.

    §

     Department of Organic Chemistry, University of Yaoundé I.

    *

     To whom correspondence should be addressed. Tel:  +82-42-860-4295. Fax:  +82-42-860-4595. E-mail:  [email protected].

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