Isolation of onosmins A and B, lipoxygenase inhibitors from Onosma hispida

Chem Pharm Bull (Tokyo). 2005 Aug;53(8):907-10. doi: 10.1248/cpb.53.907.

Abstract

Onosmins A (1) and B (2), lipoxygenase inhibitors, have been isolated from Onosma hispida. Their structures were established as 2-[(4-methylbenzyl)amino]benzoic acid (1) and methyl 2-[(4-methylbenzyl)amino]benzoate (2) through spectroscopic studies, including 2D-NMR. The known compounds apigenin (3), 6,4'-dimethoxy-3,5,7-trihydroxyflavone (4), 6,7-dimethoxy-3,5,4'-trihydroxyflavone (5) and apigenin 7-O-beta-D-glucoside (6) are also reported for the first time from this species. Compounds (1) and (2) inhibited lipoxygenase (LOX, EC 1.13.11.12) enzyme in a concentration-dependent fashion with IC50 values of 24.0 and 36.2 microM, respectively. Lineweaver-Burk as well as Dixon plots and their secondary replots indicated that the nature of inhibition was purely a non-competitive type, with K(i) values 22.0 microM and 31.1, respectively.

MeSH terms

  • Benzoates / chemistry
  • Benzoates / isolation & purification*
  • Benzyl Compounds / chemistry
  • Benzyl Compounds / isolation & purification*
  • Boraginaceae / chemistry*
  • Lipoxygenase Inhibitors / pharmacology*
  • Spectrum Analysis / methods

Substances

  • Benzoates
  • Benzyl Compounds
  • Lipoxygenase Inhibitors
  • onosmin A
  • onosmin B