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Ubiquinone-1

(Synonyms: 辅酶Q1) 目录号 : GC30723

An electron acceptor

Ubiquinone-1 Chemical Structure

Cas No.:727-81-1

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产品描述

Coenzyme Q1 (CoQ1) is an electron acceptor and a derivative of the mitochondrial electron transport chain cofactor CoQ10 .1 It induces opening of the mitochondrial permeability transition pore and apoptosis in clone 9 cells when used at a concentration of 50 ?M.2 Coenzyme Q1 has been used in the detection of mitochondrial complex I, also known as NADH dehydrogenase, activity in perfused tissue and subcellular fractions.3,1

1.Fato, R., Estornell, E., DiBernardo, S., et al.Steady-state kinetics of the reduction of coenzyme Q analogs by complex I (NADH:ubiquinone oxidoreductase) in bovine heart mitochondria and submitochondrial particlesBiochemistry35(8)2705-2716(1996) 2.Devun, F., Walter, L., Belliere, J., et al.Ubiquinone analogs: A mitochondrial permeability transition pore-dependent pathway to selective cell deathPLoS One5(7)(2010) 3.Bongard, R.D., Myers, C.R., Lindemer, B.J., et al.Coenzyme Q(1) as a probe for mitochondrial complex I activity in the intact perfused hyperoxia-exposed wild-type and Nqo1-null mouse lungAm. J. Physiol. Lung Cell. Mol. Physiol.302(9)L949-L958(2012)

Chemical Properties

Cas No. 727-81-1 SDF
别名 辅酶Q1
化学名 2,3-dimethoxy-5-methyl-6-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione
Canonical SMILES O=C1C(OC)=C(OC)C(C(C)=C1C/C=C(C)\C)=O
分子式 C14H18O4 分子量 250.29
溶解度 DMF: 10 mg/ml,Ethanol: 10 mg/ml 储存条件 Store at -20°C
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1 mM 3.9954 mL 19.9768 mL 39.9537 mL
5 mM 0.7991 mL 3.9954 mL 7.9907 mL
10 mM 0.3995 mL 1.9977 mL 3.9954 mL
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Research Update

Understanding Ubiquinone

Trends Cell Biol.2016 May;26(5):367-378.PMID: 26827090DOI:10.1016/j.tcb.2015.12.007

Ubiquinone (UQ; also known as coenzyme Q; CoQ) is a mobile component of the mitochondrial electron transport chain, where it acts as a pro-oxidant in its ubisemiquinone state. Despite this, UQ is also believed to be a membrane antioxidant. These properties place UQ at the center of hotly debated questions about how mitochondria and reactive oxygen species (ROS) impact aging and disease. New studies using transgenic mouse models have provided unexpected insights into whether, and how, UQ is required in various processes, cell types, and subcellular locations. These studies have not only shed light on the role of mitochondria and ROS in the aging process, but also question the mechanisms of action by which UQ might function as a therapeutic agent.

The Complexity of Making Ubiquinone

Trends Endocrinol Metab.2019 Dec;30(12):929-943.PMID: 31601461DOI:10.1016/j.tem.2019.08.009.

Ubiquinone (UQ, coenzyme Q) is an essential electron transfer lipid in the mitochondrial respiratory chain. It is a main source of mitochondrial reactive oxygen species (ROS) but also has antioxidant properties. This mix of characteristics is why ubiquinone supplementation is considered a potential therapy for many diseases involving mitochondrial dysfunction. Mutations in the ubiquinone biosynthetic pathway are increasingly being identified in patients. Furthermore, secondary ubiquinone deficiency is a common finding associated with mitochondrial disorders and might exacerbate these conditions. Recent developments have suggested that ubiquinone biosynthesis occurs in discrete domains of the mitochondrial inner membrane close to ER-mitochondria contact sites. This spatial requirement for ubiquinone biosynthesis could be the link between secondary ubiquinone deficiency and mitochondrial dysfunction, which commonly results in loss of mitochondrial structural integrity.

Advances in bacterial pathways for the biosynthesis of ubiquinone

Biochim Biophys Acta Bioenerg.2020 Nov 1;1861(11):148259.PMID: 32663475DOI:10.1016/j.bbabio.2020.148259

Ubiquinone is an important component of the electron transfer chains in proteobacteria and eukaryotes. The biosynthesis of ubiquinone requires multiple steps, most of which are common to bacteria and eukaryotes. Whereas the enzymes of the mitochondrial pathway that produces ubiquinone are highly similar across eukaryotes, recent results point to a rather high diversity of pathways in bacteria. This review focuses on ubiquinone in bacteria, highlighting newly discovered functions and detailing the proteins that are known to participate to its biosynthetic pathways. Novel results showing that ubiquinone can be produced by a pathway independent of dioxygen suggest that ubiquinone may participate to anaerobiosis, in addition to its well-established role for aerobiosis. We also discuss the supramolecular organization of ubiquinone biosynthesis proteins and we summarize the current understanding of the evolution of the ubiquinone pathways relative to those of other isoprenoid quinones like menaquinone and plastoquinone.

Ubiquinol is superior to ubiquinone to enhance Coenzyme Q10 status in older men

Food Funct.2018 Nov 14;9(11):5653-5659.PMID: 30302465DOI:10.1039/c8fo00971f

Coenzyme Q10 (CoQ10) exerts its functions in the body through the ability of its benzoquinone head group to accept and donate electrons. The primary functions are to relay electrons for ATP production in the electron transport chain and to act as an important lipophilic antioxidant. Ubiquinone, the oxidized form of CoQ10, is commonly formulated in commercial supplements, and it must be reduced to ubiquinol to exert CoQ10's functions after consumption. Thus, we aimed to examine whether as compared to ubiquinone, ubiquinol would be more effective to enhance the CoQ10 status in older men. We conducted a double-blind, randomized, crossover trial with two 2-week intervention phases and a 2-week washout between crossovers. Ten eligible older men were randomized to consume either the ubiquinol or ubiquinone supplement at a dose of 200 mg d-1 with one of the main meals. A total of 4 blood samples were collected after an overnight fast for the determination of ubiquinone and ubiquinol in plasma and PBMC and the assessment of FRAP, total thiol, and malondialdehyde (MDA) in plasma and ATP in PBMC. After 2 weeks of the supplementation, the ubiquinol supplement significantly increased plasma ubiquinone 1.7 fold from 0.2 to 0.6 μmol L-1 and total CoQ10 (the sum of 2 forms) 1.5 fold from 1.3 to 3.4 μmol L-1 (p < 0.05) and tended to increase the plasma ubiquinol status 1.5 fold from 1.1 to 2.8 μmol L-1, but did not alter the ratio of ubiquinol to total CoQ10. The ubiquinone supplement insignificantly increases plasma ubiquinol, ubiquinone, and total CoQ10 and did not affect the ratio. Of 10 subjects, six were more responsive to the ubiquinol supplement and 2 were more so to the ubiquinone. The supplementation of both CoQ10 forms did not alter the CoQ10 status in PBMC. FRAP, total thiol, and MDA in plasma and ATP in PBMC were not changed during the intervention. The significant increase in plasma CoQ10 status observed after the 2-week supplementation suggested that ubiquinol appeared to be a better supplemental form to enhance the CoQ10 status than ubiquinone in older men. Neither ubiquinol nor ubiquinone supplement affected the measured biomarkers of oxidative stress.

Ubiquinone and tocopherol: dissimilar siblings

Biochem Pharmacol.2008 Aug 1;76(3):289-302.PMID: 18499086DOI:10.1016/j.bcp.2008.04.003

Research on antioxidants and their potential health benefits expanded over the last decades from basic science to the medical and nutritional fields. This included supplementation studies of both vitamin E compounds and the endogenous antioxidant ubiquinone, to prevent or alleviate cardiovascular diseases and their pathophysiological consequences. In many of these studies, only one antioxidant or one group of antioxidants was considered, disregarding the pharmacological and toxicological properties of their metabolites as well as possible cooperative and competitive effects on the overall physiological response. There are many--often indirect--effects, especially in gene regulation, observed on administration of both compound groups in cells, which have been assigned to these molecules without identifying the cellular targets. Therefore, this article focuses on direct chemical and biochemical effects of ubiquinone- and alpha-tocopherol-related compounds, which are evident from direct binding studies or direct interaction leading to chemical modification of the compounds. These groups include para-benzoquinones (ubiquinone and alpha-tocopheryl quinone) and chroma(e)nols (alpha-tocopherol and bicyclic ubiquinone derivatives). Their effects as antioxidants, co-antioxidants, and pro-oxidants as well as direct interactions with proteins are considered, pointing out similarities and dissimilarities of the two compound groups in a wider context. The review of the isolated findings about one or a few of these compounds in the literature, disregarding structurally related compounds, suggests that comprehensive structure/activity relationship studies including related compounds would promote the understanding of biological functions and pharmacological effects of ubiquinone- and alpha-tocopherol-related compounds.