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Chemical Compound Review

HXB3     (5Z,8Z)-10-hydroxy-10- [(2R,3S)-3-[(Z)-oct...

Synonyms: hepoxilin B3, CHEBI:34784, HMDB04690, AC1NR1RK, C14810
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High impact information on LMFA03090003

  • The insulin release enhancer, 10-hydroxy-11,12-trans-epoxy-5(Z),8(Z),14(Z)-icosatrienoic acid (hepoxilin B3), is a 12-lipoxygenase metabolite of arachidonic acid that has been found in various mammalian tissues [1].
  • The hepoxilin B3-synthesizing activity was not observed in subcellular fractions incubated with authentic 12(S)-hydroperoxyeicosatetraenoic acid, although it was located at least in the microsomal fraction when incubated with arachidonic acid [2].
  • Furthermore, the stable hepoxilin B3 analogue PBT-3 stimulated hatching at 10(-7) mol l(-1) [3].
  • In contrast, boiled neutrophil preparations converted 12-HPETE primarily into hepoxilin B3 which previously showed to be derived nonenzymatically [4].


  1. Discovery of the mammalian insulin release modulator, hepoxilin B3, from the tropical red algae Platysiphonia miniata and Cottoniella filamentosa. Moghaddam, M.F., Gerwick, W.H., Ballantine, D.L. J. Biol. Chem. (1990) [Pubmed]
  2. Stereoselective biosynthesis of hepoxilin B3 in human epidermis. Antón, R., Vila, L. J. Invest. Dermatol. (2000) [Pubmed]
  3. Hepoxilins and trioxilins in barnacles: an analysis of their potential roles in egg hatching and larval settlement. Vogan, C.L., Maskrey, B.H., Taylor, G.W., Henry, S., Pace-Asciak, C.R., Clare, A.S., Rowley, A.F. J. Exp. Biol. (2003) [Pubmed]
  4. 12-HETE and 12-HPETE potently stimulate intracellular release of calcium in intact human neutrophils. Reynaud, D., Pace-Asciak, C.R. Prostaglandins Leukot. Essent. Fatty Acids (1997) [Pubmed]
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