Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H10O3 |
| Molecular Weight | 130.1418 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]1(O)CCOC(=O)C1
InChI
InChIKey=JYVXNLLUYHCIIH-ZCFIWIBFSA-N
InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m1/s1
Mevalonolactone (ML) is a lactone form of mevalonic acid (MA), they exist in equilibrium. Mevalonolactone is used to study the effect of statin on the prenylation of Ras and Rho GTPases. Recently was discovered, that mevalonolactone disrupted mitochondrial functions and induced permeability transition pore opening in rat brain mitochondria, what can be important for the pathogenesis of mevalonic aciduria. Mevalonic aciduria is caused by severe deficiency of mevalonic kinase activity leading to tissue accumulation and high urinary excretion of mevalonic acid and mevalonolactone. It was proved that ML impaired essential brain mitochondrial functions with the involvement of MPT pore opening and that disturbance of brain mitochondrial homeostasis contributed to the neurologic symptoms of MVA.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthetic applications of epoxide hydrolases. | 2001 Apr |
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| Prolonged inhibition of cholesterol synthesis by atorvastatin inhibits apo B-100 and triglyceride secretion from HepG2 cells. | 2001 Jul |
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| Isoprenoid biosynthesis is not compromised in a Zellweger syndrome mouse model. | 2001 May 31 |
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| Investigation of a functional requirement for isoprenylation by the human prostacyclin receptor. | 2002 Mar |
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| [Mevalonolactone: a volatile compound produced by Psammotettix alienus (Dhb)]. | 2002 Sep |
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| Biogenetic studies in Syringa vulgaris L.: synthesis and bioconversion of deuterium-labeled precursors into lilac aldehydes and lilac alcohols. | 2003 Jan 15 |
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| HMG-CoA reductase inhibition aborts functional differentiation and triggers apoptosis in cultured primary human monocytes: a potential mechanism of statin-mediated vasculoprotection. | 2003 Jul 19 |
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| Methodology for synthesis and isolation of 5-phosphomevalonic acid. | 2003 Oct 15 |
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| Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia. | 2004 Aug |
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| Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs. | 2004 Feb 18 |
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| Leukaemia inhibitory factor or oncostatin M induction of Swiss 3T3 cells does not require mevalonic acid synthesis nor protein isoprenylation to initiate DNA replication. | 2004 Jan 23 |
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| Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS. | 2004 Jun 1 |
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| Prenylation-defective human connexin32 mutants are normally localized and function equivalently to wild-type connexin32 in myelinating Schwann cells. | 2005 Aug 3 |
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| 4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway. | 2005 Jun |
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| Effect of geraniol on fatty-acid and mevalonate metabolism in the human hepatoma cell line Hep G2. | 2006 Feb |
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| Activators of the energy sensing kinase AMPK inhibit random cell movement and chemotaxis in U937 cells. | 2006 Feb |
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| Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies. | 2006 Feb 22 |
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| Validation of the LC-MS/MS method for the quantification of mevalonic acid in human plasma and determination of the matrix effect. | 2006 Oct |
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| Protective effects of a squalene synthase inhibitor, lapaquistat acetate (TAK-475), on statin-induced myotoxicity in guinea pigs. | 2007 Aug 15 |
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| Statins stimulate in vitro membrane FasL expression and lymphocyte apoptosis through RhoA/ROCK pathway in murine melanoma cells. | 2007 Dec |
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| Determination of key intermediates in cholesterol and bile acid biosynthesis by stable isotope dilution mass spectrometry. | 2008 Mar 25 |
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| Inhibition of rho family functions by lovastatin promotes myelin repair in ameliorating experimental autoimmune encephalomyelitis. | 2008 May |
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| Effects of cholesterol and nuclear hormone receptor agonists on the production of transforming growth factor-beta in macrophages. | 2009 Sep |
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| Increasing diterpene yield with a modular metabolic engineering system in E. coli: comparison of MEV and MEP isoprenoid precursor pathway engineering. | 2010 Feb |
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| Involvement of the phospholipid sterol acyltransferase1 in plant sterol homeostasis and leaf senescence. | 2010 Jan |
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| Cloning and characterization of a novel gene that encodes (S)-beta-bisabolene synthase from ginger, Zingiber officinale. | 2010 Jun |
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| Functional annotation, genome organization and phylogeny of the grapevine (Vitis vinifera) terpene synthase gene family based on genome assembly, FLcDNA cloning, and enzyme assays. | 2010 Oct 21 |
Sample Use Guides
In order to examine the mechanisms by which mevalonolactone (ML) compromise brain mitochondrial functions, it was investigated the influence of ML and mevalonic acid (MA) on mitochondrial membrane fluidity since it may lead to conformational changes during the assembly of membrane proteins that constitute the pore and potentially represent an underlying mechanism responsible for the MPT pore opening. Mitochondrial preparations (0.5 mg protein. mL-1) and MA or ML (1 mM) were added to the incubation medium in the beginning of the assays. It was observed that ML and MA were not able to alter mitochondrial membrane fluidity, ruling out this mechanism as the cause of the deleterious effects provoked by ML on mitochondrial functions. It was verified that ML, but not MA, provoked mitochondrial lipid peroxidation, as determined by increased MDA formation. Furthermore, only ML decreased brain ACO activity, with no alterations of this activity caused by MA.
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LOINC |
48145-7
Created by
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1442202
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661X270Z3L
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661X270Z3L
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6419891
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19115-49-2
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C015367
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SUBSTANCE RECORD
