SML0301

Hymeglusin

from Fusarium sp., ≥98% (HPLC), powder, HMG-CoA synthase inhibitor

• Synonym(e): (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
• Empirische Formel (Hill-System): C₁₈H₂₈O₅
• CAS-Nummer: 29066-42-0
• Molekulargewicht: 324.41
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder

Eigenschaften

• Produktname: Hymeglusin, ≥98% (HPLC), from Fusarium sp.
• biological source: Fusarium sp.
• Quality Segment: 200
• assay: ≥98% (HPLC)
• form: powder
• solubility: DMSO: soluble, H₂O: insoluble, acetone: soluble, chloroform: soluble, ethyl acetate: soluble
• storage temp.: −20°C
• SMILES string: O1[C@@H]([C@H](C1=O)CO)CCCC[C@H](C\C(=C\C(=C\C(=O)O)\C)\C)C
• 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

Beschreibung

Biochem/physiol Actions

Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway.

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.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable