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SML0301 Sigma-Aldrich

Hymeglusin

≥98% (HPLC), from Fusarium sp.

Synonym: (2E, 4E, 7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid, Antibiotic 1233A, F-244, L-659,699

  • CAS Number 29066-42-0

  • Empirical Formula (Hill Notation) C18H28O5

  • Molecular Weight 324.41

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cholesterol and Cholesterol Metabolism,
biological source   Fusarium sp.
assay   ≥98% (HPLC)
form   powder
solubility   DMSO: soluble
  H2O: insoluble
  acetone: soluble
  chloroform: soluble
  ethyl acetate: soluble
storage temp.   −20°C

Description

Biochem/physiol Actions

Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway. Unlike other fungal metabolites, Hymeglusin inhibits mevalonate biosynthesis by acting on HMG-CoA synthase, while other fungal metabolites such as Lovastatin (Mevinolin) and Compactin act as specific competitive inhibitors of the HMG-CoA reductase. Inhibition results from covalent modification of the active Cys129 residue by the enzyme by the formation of a thioester adduct in the active site. Hymeglusin show no inhibitory effect against fatty acid synthetase purified from Sacharomyces serevisiae. Hymeglusin was found to block the growth of Enterococcus faecalis. After removal of the inhibitor from the culture medium, a growth curve inflection point is observed. Upon Hymeglusin inactivation, enzyme activity is restored at a rate that is 8-fold faster for human HMGCS than for the bacterial enzyme (mvaS). Structural studies explain these differences. Hymeglusin was also found to inhibit the replication of the dengue live virus (DEN-2 NGC virus) in K562 cells. Lovastatin inhibits DEN-2 NGC live virus replication in human peripheral blood mononuclear cells.

Preparation Note

A DMSO solution (1 mg/mL) is stable for one month at −20 °C.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
YQ1170000

Documents

Certificate of Analysis

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Milli-Q® Water Purification Solutions
Protocols & Articles
Peer-Reviewed Papers
15

References

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