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)

PHYSICAL AND CHEMICAL PROPERTIES

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SPECTRAL DATA

UV SPECTRA	:	lmax 270 mm, E¹^%₁_c_m = 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^%₁_c_m =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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