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 |
|---|---|---|
| Involvement of oxidative stress in simvastatin-induced apoptosis of murine CT26 colon carcinoma cells. | 2010-12-15 |
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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. | 2010-10-21 |
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| Cloning and characterization of a novel gene that encodes (S)-beta-bisabolene synthase from ginger, Zingiber officinale. | 2010-06 |
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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. | 2010-02 |
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| Involvement of the phospholipid sterol acyltransferase1 in plant sterol homeostasis and leaf senescence. | 2010-01 |
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| Synthesis and HMG-CoA reductase inhibition of 2-cyclopropyl-4-thiophenyl-quinoline mevalonolactones. | 2009-12-01 |
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| Effects of cholesterol and nuclear hormone receptor agonists on the production of transforming growth factor-beta in macrophages. | 2009-09 |
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| Conjugated hyperbilirubinaemia as the first manifestation of mevalonic aciduria in a term newborn. | 2009 |
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| Complete blockage of the mevalonate pathway results in male gametophyte lethality. | 2009 |
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| Stable carbon isotope discrimination by human 3-hydroxy-3-methylglutaryl-coenzyme A reductase. | 2008-12 |
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| Inhibition of rho family functions by lovastatin promotes myelin repair in ameliorating experimental autoimmune encephalomyelitis. | 2008-05 |
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| Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in Arabidopsis. | 2008-04 |
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| Determination of key intermediates in cholesterol and bile acid biosynthesis by stable isotope dilution mass spectrometry. | 2008-03-25 |
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| Statins induce lethal effects in acute myeloblastic leukemia [corrected] cells within 72 hours. | 2008-02 |
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| Statins stimulate in vitro membrane FasL expression and lymphocyte apoptosis through RhoA/ROCK pathway in murine melanoma cells. | 2007-12 |
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| Protective effects of a squalene synthase inhibitor, lapaquistat acetate (TAK-475), on statin-induced myotoxicity in guinea pigs. | 2007-08-15 |
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| Modulation by simvastatin of iberiotoxin-sensitive, Ca2+-activated K+ channels of porcine coronary artery smooth muscle cells. | 2007-08 |
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| Highly sensitive assay of HMG-CoA reductase activity by LC-ESI-MS/MS. | 2007-05 |
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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. | 2006-10 |
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| Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies. | 2006-02-22 |
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| Effect of geraniol on fatty-acid and mevalonate metabolism in the human hepatoma cell line Hep G2. | 2006-02 |
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| Activators of the energy sensing kinase AMPK inhibit random cell movement and chemotaxis in U937 cells. | 2006-02 |
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| Juvenile hormone titer versus juvenile hormone synthesis in female nymphs and adults of the German cockroach, Blattella germanica. | 2006 |
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| Prenylation-defective human connexin32 mutants are normally localized and function equivalently to wild-type connexin32 in myelinating Schwann cells. | 2005-08-03 |
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| 4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway. | 2005-06 |
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| Suppression of autoimmune retinal disease by lovastatin does not require Th2 cytokine induction. | 2005-02-15 |
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| Revised chirality of the acyl group of 8'-O-(3-hydroxy-3-methylglutaryl)-8'-hydroxyabscisic acid. | 2004-09 |
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| Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia. | 2004-08 |
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| Calmodulin antagonist W-7 inhibits de novo synthesis of cholesterol and suppresses secretion of de novo synthesized and preformed lipids from cultured hepatocytes. | 2004-06-01 |
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| Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS. | 2004-06-01 |
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| Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs. | 2004-02-18 |
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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. | 2004-01-23 |
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| Methodology for synthesis and isolation of 5-phosphomevalonic acid. | 2003-10-15 |
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| Frontalin: De novo biosynthesis of an aggregation pheromone component by Dendroctonus spp. bark beetles (Coleoptera: Scolytidae). | 2003-08 |
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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. | 2003-07-19 |
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| Lovastatin inhibits brain endothelial cell Rho-mediated lymphocyte migration and attenuates experimental autoimmune encephalomyelitis. | 2003-05 |
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| Effect of phytosterols on cholesterol metabolism and MAP kinase in MDA-MB-231 human breast cancer cells. | 2003-02 |
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| Biogenetic studies in Syringa vulgaris L.: synthesis and bioconversion of deuterium-labeled precursors into lilac aldehydes and lilac alcohols. | 2003-01-15 |
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| Squalene synthase inhibitors suppress triglyceride biosynthesis through the farnesol pathway in rat hepatocytes. | 2003-01 |
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| Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines. | 2003-01 |
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| Simultaneous evaluation of HMG-CoA reductase and cholesterol 7alpha-hydroxylase activities by electrospray tandem MS. | 2002-11 |
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| Pughiinin A, a sesquiterpene from the fungus Kionochaeta pughii BCC 3878. | 2002-11 |
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| [Mevalonolactone: a volatile compound produced by Psammotettix alienus (Dhb)]. | 2002-09 |
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| Mevastatin induces degeneration and decreases viability of cAMP-induced differentiated neuroblastoma cells in culture by inhibiting proteasome activity, and mevalonic acid lactone prevents these effects. | 2002-06-01 |
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| CD43 polarization in unprimed T cells can be dissociated from raft coalescence by inhibition of HMG CoA reductase. | 2002-04-01 |
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| Investigation of a functional requirement for isoprenylation by the human prostacyclin receptor. | 2002-03 |
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| Progesterone inhibits apolipoprotein-mediated cellular lipid release: a putative mechanism for the decrease of high-density lipoprotein. | 2001-06-29 |
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| Prenyl group identification of rap2 proteins: a ras superfamily member other than ras that is farnesylated. | 1993-01-15 |
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| The gamma subunit of transducin is farnesylated. | 1990-10 |
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| Lipid and lipoprotein metabolism in Hep G2 cells. | 1988-08-12 |
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
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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
