SML0301

Hymeglusin

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

• Sinónimos: (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
• Fórmula empírica (notación de Hill): C₁₈H₂₈O₅
• Número de CAS: 29066-42-0
• Peso molecular: 324.41
• Código UNSPSC: 51111800
• NACRES: NA.77

Propiedades

• Nombre del producto: Hymeglusin, ≥98% (HPLC), from Fusarium sp.
• origen biológico: Fusarium sp.
• Nivel de calidad: 200
• Ensayo: ≥98% (HPLC)
• Formulario: powder
• solubilidad: DMSO: soluble; H₂O: insoluble; acetone: soluble; chloroform: soluble; ethyl acetate: soluble
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: ODCZJZWSXPVLAW-KXCGKLMDSA-N

Descripción

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

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

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable