Ubiquinone関連化合物の化学

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概要

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• Many ubiquinone related compounds have been obtained photochemically, chemically, metabolically from ubiquinone-7 (Q-7) and isolated from natural sources. Their structures and the reaction mechanisms have been elucidated : Irradiation of Q-7 with sunlight results in the reduction of the quinone ring, the demethylation of the methoxyl group, the isomerization and oxidation of the isoprenoid side chain. The reduction of Q-7 and its hydroquinone compound with LiAlH_4 leads to the demethylation. The acetate of ubichromenol-6 (UC-6) undergoes cleavage of the chromene ring by the same reaction to give several quinones. Treatment of UC-6 with Na in ethanol results in the reduction and cleavage of the chromene ring. Metabolites of Q-7 in which the isoprenoid side chain was oxidized were isolated from the urine, adrenals and ovaries of animals dosed with Q-7; the possible metabolic pathway are discussed. Compounds having an epoxy group in the side chain were obtained from the heart muscle of the whale as well as cells of Pseudomonas sp. Some new observations are also reported on the behavior of the ubiquinone related compounds in teh NMR, mass spectra and in gas liquid chromatography. The ubiquinone related compounds were assayed to determine their ability to restore the activity of acetone-treated mitochondria in the succinate oxidase system.

• 日本ビタミン学会の論文
• 1970-12-25

著者

• 森本 浩

  Central Reseach Division Takeda Chemical Industries Ltd.

• 今田 伊助

  Central Reseach Division Takeda Chemical Industries Ltd.

• 今田 伊助

  武田薬品工業株式会社中央研究所

• 森本 浩

  武田薬品工業株式会社中央研究所

• 今田 伊助

  武田薬品工業

関連論文

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• Synthesis of Hydroquinone Monosulfates Having Carboxyalkyl and Hydroxyalkyl Side Chains
• Synthesis of immunologically Active Muramyl Dipeptide Derivatives containing a Quinonyl Moiety via Aminoacyl Intermediates
• Novel Quinonyl Derivatives of Muramyl Dipeptide Possessing Potent Antitumor Activity
• 8.Ubiquinone(35)の光反応とその生成物(第92回会議研究発表要旨)
• Synthesis, Metabolism, and in Vitro Biological Activities of 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (CV-2619)-Related Compounds
• Effects of 6-(ω-Substituted Alkyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinones and Related Compounds on Mitochondrial Succinate and Reduced Nicotinamide Adenine Dinucleotide Oxidase Systems
• Spirocyclopropane Compounds. IV. Synthesis of 5-Acetylspiro-[benzofuran-2 (3H), 1'-cyclopropan]-3-one Related Compounds for Evaluation as Gastric Antisecretory and Antiulcer Agents
• Spirocyclopropane Compounds. III. Synthesis of Spiro [benzofuran-2 (3H), 1'-cyclopropan]-3-ones for Evaluation as Gastric Antisecretory and Antiulcer Agents
• Synthesis of Quinones having Carboxy- and Hydroxy-Alkyl Side Chains, and Their Effects on Rat-Liver Lysosomal Membrane
• ユビキノンの代謝と生理活性 : 日本ビタミン学会第30回大会シンポジウム(脂溶性ビタミンに関する最近の進歩)
• Ubiquinone and Related Compounds. XXXI. Synthesis of Urinary Metabolites of Ubiquinone, Phylloquinone, α-Tocopherol and Their Related Compounds
• Ubiquinone and Related Compounds. XXVII. Synthesis of Urinary Metabolites of Phylloquinone and α-Tocopherol
• Ubiquinone and Related Compounds. XXVIII. Effect of the Metabolites of α-Tocopherol, Phylloquinone and Ubiquinone on the Stability of Rat-liver Lysosomal Membrane
• Ubiquinone and Related Compounds. XXVI. The Urinary Metabolites of Phylloquinone and α-Tocopherol
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• Effect of 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (CV-2619) on Microsomal Lipid Peroxidation
• Spirocyclopropane Compounds. VI. : Synthesis of Spiro[benzo[b]-thiophene-2(3H), 1'-cyclopropan]-3-ones
• A Facile Synthesis of 1,4-Benzoquinones Having a Hydroxyalkyl Side Chain
• Ubiquinone and Related Compounds. XXXVIII. Biological Oxidation of Ubiquinone
• 2-II-15 ユビキノン代謝物及び関連化合物の硫酸抱合体の合成及びそれらの2,3の生理作用 : 第35回大会一般研究発表要旨 : 日本ビタミン学会
• Spirocyclopropane Compounds. I. Synthesis and Reactivity of Spiro [cyclopropane-1,2'-[2H] indol]-3'(1'H)-ones
• Ubiquinone関連化合物の化学
• Reaktionsmechanismus der Esterbildung aus N-Hydroxysuccinimid und Acylaminosaure mittels Dicyclohexylcarbodiimid
• Ubichinone und Verwandte Substanzen. VIII, Bilolgisches Verhalten des Ubichromenols (35) in Ratten
• Ubichinone und Verwandte Substanzen. VII. Quantitative Analyse der Ubichromenole
• Photochemical Reaction of Ubiquinone (35). VI. Coenzymatic Activity of Ubiquinone (35) and Related Compounds
• Photochemical Reaction of Ubiquinone (35). V. Synthesis of 2-Hydroxy-3-methoxy-5-methyl-6-phytyl-p-benzoquinone
• Photochemical Reaction of Ubiquinone (35). IV. Formation of Demethylubiquinone (35)
• Photochemical Reaction of Ubiquinone (35).III. Formation of Isoubiquinone (35)
• Photochemical Reaction of Ubiquinone (35). II. Formation of Ubichromenol (35)
• Photochemical Reaction of Ubiquinone (35). I. Photochemical Reaction of Ubiquinone (35)
• Photochemische Reaktion von Ubichinon (35). II. Uber Ubichromenol (35) und Isoubichinon (35)
• (3)リゾープス属菌の生成するセルラーゼの研究
• Studies on the Components of Fritillaria thunbergii MIQ. II. On Peimine. (1).
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• 微生物菌体中のubiquinoneの単離法の検討

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