Lipoxygenase inhibitors derived from marine macroalgae

Bioorg Med Chem Lett. 2014 Mar 1;24(5):1383-5. doi: 10.1016/j.bmcl.2014.01.046. Epub 2014 Jan 27.

Abstract

The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z,9Z,12Z,15Z,18Z)-1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O. corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance.

Keywords: Alkapolyene; Inhibitor; Lipoxygenase; Odonthalia corymbifera; Pheophytin a; Sargassum thunbergii.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Benzamides / pharmacology*
  • Enzyme Activation / drug effects
  • Lipoxygenase / chemistry*
  • Lipoxygenase / metabolism
  • Lipoxygenase Inhibitors / chemistry*
  • Lipoxygenase Inhibitors / isolation & purification
  • Lipoxygenase Inhibitors / metabolism
  • Lipoxygenase Inhibitors / pharmacology
  • Pheophytins / chemistry*
  • Pheophytins / isolation & purification
  • Pheophytins / metabolism
  • Polyenes / chemistry*
  • Polyenes / isolation & purification
  • Polyenes / metabolism
  • Polyenes / pharmacology
  • Protein Binding
  • Seaweed / chemistry*
  • Seaweed / metabolism
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry
  • Sulfones / pharmacology*

Substances

  • 1,6,9,12,15,18-henicosahexaene
  • 1,6,9,12,15-henicosapentaene
  • Benzamides
  • Lipoxygenase Inhibitors
  • Pheophytins
  • Polyenes
  • Sulfones
  • pheophytin a
  • Lipoxygenase