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Coenzyme Q


DATA No : VCQ0007 INFORMANT : Tetsuya Nakamura

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

COMMON NAME: Coenzyme Q4
SYMBOL: Co Q4
FORMULA: C29H40O4 MOL.WT (average) : 452.625


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BIOLOGICAL ACTIVITY
The effect of coenzyme Q (Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10, but CoQ8, and CoQ7 showed almost no effect. Short homologues (less than Co Q4) inhibited the beating of cell sheets.(Ref. 0013)
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SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 326 in petroleum ether(Ref. 0037)

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CHEMICAL SYNTHESIS
The compound is prepared in analogy to the procedure given for ubiquinone-3 (VCQ0008) starting from 0.83 g of 2,3-dimethoxy-5-methyl-1,4-benzoquinone and 2.64 g of all-trans-geranyllinalool. Yield 26.4%. Ultraviolet absorption maximum at 271 nm (Ed1%1cm =350) (in hexane). (Ref. 0003)
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REFERENCES
[0003]
AUTHOR:Obol'nikova, E. A., Volkova, O. I., and Samokhvalov, G. I.
TITLE:Synthetic studies of polyenes XXVIII. Complete synthesis of coenzyme Q2, Q3, Q4, and hexahydro-Q4
JOURNAL:Zhurnal Obshchei Khimii (English translation)
VOL:38 PAGE : 459 -462 (1966)
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[0013]
AUTHOR:Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T.
TITLE:Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709
JOURNAL:Clin Investig.
VOL:71 PAGE : S71-75 (1993)
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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.