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Chemical Compound Review: 

Lipstatin     [(2S,4E,7E)-1-(3-hexyl-4-oxo- oxetan-2...

Synonyms: AC1O5Q44, A23538, 96829-59-3
 
 
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Disease relevance of Lipstatin

  • The lipase inhibitor lipstatin is biosynthesized in Streptomyces toxytricini via condensation of a C(14) precursor and a C(8) precursor, which are both obtained from fatty acid catabolism [1].
 

High impact information on Lipstatin

  • The biosynthesis of the pancreatic lipase inhibitor lipstatin was investigated by fermentation experiments using cultures of Streptomyces toxytricini, which were supplied with soybean oil and a crude mixture of U-13C-lipids obtained from algal biomass cultured with 13CO2 [2].
  • (2)H NMR and mass spectroscopy confirmed the incorporation of (5Z,8Z)-[10,11,12,12-(2)H]tetradeca-5,8-dienoic acid into the C(13) side chain as well as into the C(6) side chain of lipstatin [3].
  • The IC50 of lipstatin for pancreatic lipase is 0.14 microM [4].
  • A standard type II polyketide synthase (PKS) gene cluster was isolated while attempting to clone the biosynthetic gene for lipstatin from Streptomyces toxytricini NRRL 15,443 [5].
  • Tetrahydrolipstatin is a specific lipase inhibitor derived from lipstatin, a lipid produced by Streptomyces toxytricini [6].

References

  1. Biosynthetic origin of hydrogen atoms in the lipase inhibitor lipstatin. Goese, M., Eisenreich, W., Kupfer, E., Weber, W., Bacher, A. J. Biol. Chem. (2000) [Pubmed]
  2. Tracer studies with crude U-13C-lipid mixtures. Biosynthesis of the lipase inhibitor lipstatin. Eisenreich, W., Kupfer, E., Weber, W., Bacher, A. J. Biol. Chem. (1997) [Pubmed]
  3. Biosynthesis of lipstatin. Incorporation of multiply deuterium-labeled (5Z,8Z)-tetradeca-5,8-dienoic acid and octanoic acid. Goese, M., Eisenreich, W., Kupfer, E., Stohler, P., Weber, W., Leuenberger, H.G., Bacher, A. J. Org. Chem. (2001) [Pubmed]
  4. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. Weibel, E.K., Hadvary, P., Hochuli, E., Kupfer, E., Lengsfeld, H. J. Antibiot. (1987) [Pubmed]
  5. Cloning and Analysis of a Type II Polyketide Synthase Gene Cluster from Streptomyces toxytricini NRRL 15,443. Yoo, A., Demirev, A.V., Lee, J.S., Kim, S.D., Nam, D.H. J. Microbiol. (2006) [Pubmed]
  6. Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin. Borgström, B. Biochim. Biophys. Acta (1988) [Pubmed]
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