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
Linear Formula: C18H28O5
Product Type: Chemical
| assay |
≥98% (HPLC) |
| biological source |
Fusarium sp. |
| form |
powder |
| InChI |
1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1 |
| InChI key |
ODCZJZWSXPVLAW-KXCGKLMDSA-N |
| Quality Level |
200  |
| solubility |
acetone: soluble |
| |
chloroform: soluble |
| |
DMSO: soluble |
| |
ethyl acetate: soluble |
| |
H2O: insoluble |
| storage temp. |
−20°C |
| 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. |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352200 |
