New isoprenylated 2-arylbenzofurans and pancreatic lipase inhibitory constituents from Artocarpus nitidus

Chem Biodivers. 2009 Dec;6(12):2209-16. doi: 10.1002/cbdv.200900130.

Abstract

Two new isoprenylated 2-arylbenzofurans, artonitidin A (=(2'R)-2',3'-dihydro-2'-(1-hydroxy-1-methylethyl)-5',7-bis(3-methylbut-2-en-1-yl)-2,4'-bi-1-benzofuran-6,6'-diol; and artonitidin B (=5-[6-hydroxy-7-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]-4-(3-methylbut-2-en-1-yl)benzene-1,3-diol; together with 14 known compounds, were isolated from the stems of Artocarpus nitidus Trec. The structures were elucidated by spectroscopic methods. Norartocarpin, cudraflavone C, brosimone I, artotonkin, albanin A, and artopetelin M showed inhibitory effects on pancreatic lipase with IC(50) values ranging from 1.8+/-0.1 to 63.8+/-3.6 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Artocarpus / chemistry*
  • Benzofurans / chemistry*
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Lipase / antagonists & inhibitors
  • Lipase / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Stems / chemistry
  • Prenylation

Substances

  • 2',3'-dihydro-2'-(1-hydroxy-1-methylethyl)-5',7-bis(3-methylbut-2-en-1-yl)-2,4'-bi-1-benzofuran-6,6'-diol
  • 5-(6-hydroxy-7-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl)-4-(3-methylbut-2-en-1-yl)benzene-1,3-diol
  • Benzofurans
  • Lipase