DL-Mevalonolactone

Description

DL-Mevalonolactone is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway. It induces depolarization and swelling, decreases NADPH content and aconitase (ACO) activity, and increases malondialdehyde (MDA) production in calcium-loaded rat brain mitochondria. DL-Mevalonolactone reverses decreases in glucose uptake induced by simvastatin (Item Nos. 10010344 | 10010345) in L6 myotubes. Tissue levels and urinary excretion of DL-mevalonolactone are increased in patients with mevalonic aciduria, a disorder characterized by a deficiency in mevalonic kinase activity.

Chemical properties

Pale Yellow Oil

The Uses of DL-Mevalonolactone

A metabolite from endophytes of the medicinal plant Erythrina crista-galli.

The Uses of DL-Mevalonolactone

HMG CoA substrate

The Uses of DL-Mevalonolactone

(±)-Mevalonolactone is used to:

• study the effect of statin on the prenylation of Ras and Rho GTPases
• analyse the isoprenoid biosynthesis pathways in Listeria monocytogenes
• study the the effects of statins on proliferation and migration of HUVECs (HGF-induced human umbilical vein endothelial cells)

What are the applications of Application

DL-Mevalonolactone is a useful substrate for biological research purposes

Definition

ChEBI: 4-hydroxy-4-methyl-2-oxanone is a delta-lactone.

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 5486, 1982 DOI: 10.1021/ja00384a040
Synthesis, p. 719, 1974 DOI: 10.1055/s-1974-23416

General Description

Alkaline hydrolysis of mevalonolactone gives mevalonate. Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.

Purification Methods

Purify the lactone via the dibenzyl-ethylenediammonium salt (m 124-125o) [Hofmann et al. J Am Chem Soc 79 2316 1957], or by chromatography on paper or on a Dowex-1 (formate) column. [Bloch et al. J Biol Chem 234 2595 1959.] Store it as the N,N'-dibenzylethylenediamine (DBED) salt, or as the lactone in a sealed container at 0o. [Beilstein 18/1 V 19.]