Inhibitory activities of three annonaceous acetogenins on NADH oxidase of chicken liver mitochondria

Biol Pharm Bull. 2003 May;26(5):729-32. doi: 10.1248/bpb.26.729.

Abstract

Annonaceous acetogenins (ACG) are natural products found in the plant family Annonaceae and which strongly inhibited mitochondrial complex I. The inhibition of NADH oxidase of chicken liver mitochondria by three different structural ACG was studied here, and ACG was shown to have potent inhibitory activities similar to rotenone for NADH oxidase. The IC(50) values indicated that bis-adjacent tetrahydrofuran (THF) type squamocin C was more potent than non-adjacent bis-THF type squamostatin B, and the latter was more potent than non-THF type compound 1 in the assay. The roles of structural factors of ACG such as the terminal gamma-lactone, the features of other ring moieties and hydroxyl groups, as well as the alkyl chain were simply discussed in this study.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology*
  • Acetogenins
  • Animals
  • Annonaceae / chemistry*
  • Chickens
  • Fatty Alcohols / chemistry
  • Fatty Alcohols / pharmacology*
  • In Vitro Techniques
  • Lactones / chemistry
  • Lactones / pharmacology*
  • Mitochondria, Liver / drug effects*
  • Mitochondria, Liver / enzymology
  • Mitochondria, Liver / metabolism
  • Multienzyme Complexes / metabolism*
  • NADH, NADPH Oxidoreductases / metabolism*
  • Rotenone / chemistry
  • Rotenone / pharmacology
  • Structure-Activity Relationship

Substances

  • Acetogenins
  • Fatty Alcohols
  • Lactones
  • Multienzyme Complexes
  • squamocin C
  • squamostatin B
  • Rotenone
  • NADH oxidase
  • NADH, NADPH Oxidoreductases
  • 4-Butyrolactone