674-26-0

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.

Pale Yellow Oil

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

HMG CoA substrate

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

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

Store at -20°C

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.]

[1] SéRGIO R DOMINGOS  Melanie S  Cristóbal Pérez. On the structural intricacies of a metabolic precursor: Direct spectroscopic detection of water-induced conformational reshaping of mevalonolactone.[J]. Journal of Chemical Physics, 2017, 147 12: 124310. DOI: 10.1063/1.4997162
[2] CRISTIANE CECATTO . Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria[J]. Neurochemistry international, 2017, 108: Pages 133-145. DOI: 10.1016/j.neuint.2017.03.005
[3] NAGENDRA YALURI  Tarja K  Shalem Modi. Simvastatin induces insulin resistance in L6 skeletal muscle myotubes by suppressing insulin signaling, GLUT4 expression and GSK-3β phosphorylation[J]. Biochemical and biophysical research communications, 2016, 480 2: Pages 194-200. DOI: 10.1016/j.bbrc.2016.10.026