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Coenzyme Q


DATA No : VCQ0010 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl- methylbutenyl-1,4-benzoquinone

COMMON NAME: Coenzyme Q1
SYMBOL: Co Q1
FORMULA: C14H13O4 MOL.WT (average) : 245.251


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BIOLOGICAL ACTIVITY
Interaction of ubiquinol with oxygen radicals was followed by their effects on luminol-activated chemiluminescence. Ubiquinols Q1- Q4 at 0.1 mM completely inhibit the luminol-activated NADPH-dependent chemiluminescent response of microsomes, while homologues Q6-Q10 exert no effect. In contrast to ubiquinol Q10 (ubiquinone Q10) ubiquinone Q1 synergistically enhances NADPH-dependent regeneration of endogenous vitamin E in microsomes thus providing for higher antioxidant protection against lipid peroxidation. The differences in the antioxidant potency of ubiquinols in membranes are suggested to result form differences in partitioning into membranes, intramembrane mobility and non-uniform distribution of ubiquinol resulting in differing efficiency of interaction with oxygen and lipid radicals as well as different efficiency of ubiquinols in regeneration of endogenous vitamin E.(Ref. 0019)
O2- generation in mitochondrial electron trasport systems, especially the NADPH-coenzyme Q10 oxidorecuctase system, was examined using a model system, NADPH-coenzymeQ 1-dependent cytocrome P-450 reductase. One electron reuction of coenzyme Q1 produces coenzyme Q1- and O2-during enzyme-catalyzed reduction and O2 + coenzyme Q 1- are in equilibrium with O2- + coenzyme Q 1 In the presence of enough O2 , The coenzyme Q1- produced can be completely eliminated by superoxide dismutase, identical to bound coenzyme Q10 radical produced in succinate/ fumarate couple-KCN-submitochondrial system in the presence of O2. Superoxide dismutase promotes electron transfer from reduced enzyme to coenzyme Q1 by the rapid dismutation of O2- generated, thereby preventing the reduction of coenzyme Q1 by O2-. The enzymatic reduction of coenzyme Q1 to coenzyme Q1H2 via coenzyme Q1- is smoothly achieved under anaerobic conditions.(Ref. 0021)
PHYSICAL AND CHEMICAL PROPERTIES
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SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 590 in petroleum ether(Ref. 0037)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA: (a) ESR spectrum of coenzyme Q1 semiquinone radical. ESR signals dwere taken at 30-140 s after the additionof NADPH at 25degC.
[Table 0001] (b) The reacrion mixture contained 1.6 units of NADPH-cytochrome P-450 reductase/1.6 mM coenzyme Q1 /0.8mM NADPH, NADPH-generating system and 0.1 M Tris-HCl buffer (pH 7.5).
[Table 0001] (Ref. 0021)
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

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REFERENCES
[0019]
AUTHOR:Kagan, V. E., Serbinova, E. A., Koynova, G. M., Kitanova, S. A., Tyurin, V. A., Stoytchev, T. S., Quinn, P. J., and Packer, L.
TITLE:Antioxidant action of ubiquinol homologues with different isoprenoid chain length in biomembranes PubMed ID:2227528
JOURNAL:Free Radic Biol Med.
VOL:9 PAGE : 117-126 (1990)
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[0021]
AUTHOR:Sugioka, K., Nakano, M., Totsune-Nakano, H., Minakami, H., Tero-Kubota, S., and Ikegami, Y.
TITLE:Mechanism of O2- generation in reduction and oxidation cycle of ubiquinones in a model of mitochondrial electron transport systems PubMed ID:2848580
JOURNAL:Biochim Biophys Acta.
VOL:936 PAGE : 377-385 (1988)
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[0037]
AUTHOR:Sommer,P., and Kofler,M.
TITLE:Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867
JOURNAL:Vitamins and Hormones
VOL:24 PAGE : 349 -399 (1966)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.