Citrusosides A-D and furanocoumarins with cholinesterase inhibitory activity from the fruit peels of Citrus hystrix

J Nat Prod. 2010 Nov 29;73(11):1879-83. doi: 10.1021/np100531x. Epub 2010 Oct 21.

Abstract

Four new compounds, citrusosides A-D (1-4), and 15 known compounds were isolated from the hexanes and CH(2)Cl(2) extracts of the peels of Citrus hystrix fruits. Compound 1 is a 1-O-isopropyl-6-O-β-D-glucopyranosyl ester of 5'',9''-dimethyl-2'',8''-decadienoic acid. Compounds 2-4 possess a 1-O-isopropyl-β-D-glucopyranosyl and a dihydroxyprenylfuranocoumarin moiety conjugated to the 3-hydroxy-3-methylglutaric acid as diesters. Several furanocoumarins were evaluated for their cholinesterase inhibitory activity. (R)-(+)-6'-Hydroxy-7'-methoxybergamottin, (R)-(+)-6',7'-dihydroxybergamottin, and (+)-isoimparatorin showed IC(50) values of 11.2 ± 0.1, 15.4 ± 0.3, and 23 ± 0.2 μM, respectively. Bioassay results indicated that the presence of a dioxygenated geranyl chain in the test compounds is crucial for the inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrylcholinesterase / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology*
  • Citrus / chemistry*
  • Fruit / chemistry
  • Furocoumarins / chemistry
  • Furocoumarins / isolation & purification*
  • Furocoumarins / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sitosterols / chemistry
  • Sitosterols / isolation & purification*
  • Sitosterols / pharmacology*
  • Stereoisomerism
  • Thailand

Substances

  • Cholinesterase Inhibitors
  • Furocoumarins
  • Glucosides
  • Sitosterols
  • Butyrylcholinesterase