Synthesis and Anti Lipid-Peroxidation Activity of Hydroquinone Monoalkyl Ethers.

Nihro, Yasunori; Furukawa, Haruhiro; Sogawa, Satoshi; Wang, Tzer Chuan; Miyataka, Hideki; Matsumoto, Hitoshi; Miki, Tsuyoshi; Satoh, Toshifumi

doi:10.1248/cpb.42.576

Cited by 27 publications

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“…Caffeic acid and chlorogenic acid were able to scavenge the stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH), and inhibit nitrosamine formation by scavenging a nitrosating agent, nitrogen sesquinixide. 26) HTHQ has potent radical-scavenging activity, in addition to reducing activity, as evaluated using the stable free radical, DPPH 27) like caffeic acid and chlorogenic acid. 26) Such an effect may be partly responsible for the observed inhibition of hepatocarcinogenesis by HTHQ.…”

Section: Discussionmentioning

confidence: 99%

Effects of Antioxidant 1‐O‐Hexyl‐2,3,5‐trimethylhydroquinone or Ascorbic Acid on Carcinogenesis Induced by Administration of Aminopyrine and Sodium Nitrite in a Rat Multi‐organ Carcinogenesis Model

Yada

Hirose

Tamano³

et al. 2002

Japanese Journal of Cancer Research

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The effect of antioxidant, 0.25% 1-O-hexyl-2,3,5-trimethylhydroquinone (HTHQ) or 0.25% ascorbic acid (AsA), on carcinogenesis induced by administration of 0.05% aminopyrine (AP) and 0.05% sodium nitrite (NaNO 2 ), was examined using a rat multi-organ carcinogenesis model. Groups of twenty F344 male rats were treated sequentially with an initiation regimen of Ndiethylnitrosamine, N-methyl-N-nitrosourea, N-butyl-N-(4-hydroxybutyl)nitrosamine, N,N′ ′ ′ ′-dimethylhydrazine and 2,2′ ′ ′ ′-dihydroxy-di-n-propylnitrosamine during the first 4 weeks, followed by AP + + + +NaNO 2 , AP + + + +NaNO 2 + + + +HTHQ, AP + + + +NaNO 2 + + + +AsA, NaNO 2 + + + +HTHQ, NaNO 2 + + + +AsA, each of the individual chemicals alone or basal diet and tap water as a control. All surviving animals were killed at week 28, and major organs were examined histopathologically for development of preneoplastic and neoplastic lesions. In the AP + + + +NaNO 2 group, the incidences of hepatocelluar adenomas and hemangiosarcomas were 95% and 35%, respectively. When HTHQ or AsA was simultaneously administered, the incidences decreased to 58% and 11%, or to 80% and 15%, respectively. On the other hand, in the AP + + + +NaNO 2 group and the NaNO 2 -alone group, when HTHQ, but not AsA, was simultaneously administered, the incidence of carcinomas in the forestomach significantly increased. The results suggest that HTHQ can prevent tumor production induced by AP and NaNO 2 more effectively than AsA. On the other hand, an enhancing or possible carcinogenic effect of simultaneous administration of HTHQ and NaNO 2 only on the forestomach is suggested, while simultaneous treatment with the same dose of AsA and NaNO 2 may not be carcinogenic to the forestomach or other organs.Key words: Antioxidants -Aminopyrine -Sodium nitrite -Carcinogenesis -RatMany nitrosoamines are known to induce tumors in various organs.1) It was reported that some drugs with secondary or tertiary amino groups reacted with nitrite under acidic conditions to form nitrosamines in vitro and in vivo. [2][3][4][5] In particular, aminopyrine (AP) is known to react with sodium nitrite (NaNO 2 ) to form dimethylnitrosamine (DMN), which is a potent liver, lung and renal carcinogen.2, 3, 6) Feeding of AP and NaNO 2 to rats has been shown to cause acute liver damage due to formation of DMN and eventually to cause liver tumors upon chronic treatment. 2,7,8) It is also known that ascorbic acid (AsA), and phenolic antioxidants such as caffeic acid, ferulic acid, butylated hydroxyanisole (BHA) and propyl gallate, inhibit the formation of DMN in rats receiving AP and NaNO 2 . 4,5) An inhibitory effect of caffeic acid on the endogenous formation of N-nitrosoproline was demonstrated in man. 9)Kuenzig et al. suggest that dietary phenols may play an important role in the prevention of carcinogenesis by inhibiting the formation of nitrosamines. 5)On the other hand, it has been reported that mutagenic compounds were formed by the interaction of polyphenols with nitrite in vitro.10, 11) It was also reported tha...

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Section: Discussionmentioning

confidence: 99%

Effects of Antioxidant 1‐O‐Hexyl‐2,3,5‐trimethylhydroquinone or Ascorbic Acid on Carcinogenesis Induced by Administration of Aminopyrine and Sodium Nitrite in a Rat Multi‐organ Carcinogenesis Model

Yada

Hirose

Tamano³

et al. 2002

Japanese Journal of Cancer Research

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“…The solvent was removed from the reaction mixture by evaporation under reduced pressure and the residue was treated by silica gel chromatography (CHCl 3 -AcOEt, 10 : 1). Compounds 3i (0.96 g, 2.18 mmol, 7%) and 4i (7.99 12) The modified method of Kiso et al 16) was used. Microsomes were prepared from male Wistar rats weighing about 200 g. The rat liver was homogenized in cold 0.25 M sucrose and the homogenate was centrifuged at 4°C (8000ϫg, 30 min).…”

Section: Synthesis Of 16-bis(4-hydroxy-235-trimethylphenoxy)hexanementioning

confidence: 99%

Antioxidative and 5-Lipoxygenase Inhibiting Activities of Novel Bis(4-hydroxy-2,3,5-trimethylphenoxy)alkyl Derivatives.

Hirano

Kawasaki

Miyataka

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Substituted phenols, and in particular p-alkoxy derivatives, are substances of a wide range of application in organic chemistry since they act as intermediates for drugs, agrochemicals, and dyes. These derivatives can also deactivate the ribonucleotide reductase in tumor cells inhibiting their growth and have been employed for melanoma treatment and applied in AIDS therapy [1][2][3][4][5][6][7]. The oxidation of cyclic and linear ketones to their respective lactones and esters, using oxidants such as organic peroxides or peroxyoxides, alkyl hydroperoxides or hydrogen peroxide, are very important industrial intermediates finding application in polymers, pharmaceuticals and herbicides production and as solvents [8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Study of Selectivity of Metal Phosphates and Phosphonates in Baeyer–Villiger Oxidations

2010

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Layered materials including metal phosphates and phosphonates have been widely investigated in several fields acting as good selective catalysts in a great number of oxidative reactions. Zirconium phosphate amorphous [Zr(HPO 4 ) 2 ÁH 2 O; ZrPA], sodium exchanged zirconium phosphate amorphous [Zr(NaPO 4 ) 2 ; NaZrPA], potassium exchanged zirconium phosphate amorphous [Zr(KPO 4 ) 2 ; KZrPA], zirconium phenylphosphonate amorphous [Zr(O 3 PC 6 H 5 ) 2 ; ZrPPA], zirconium carboxyethylphosphonate [Zr(O 3 PCH 2 CH 2 COOH) 2 ; ZrCEP] and aluminium carboxyethylphosphonate [Al 3 (OH) 3 (O 3 PCH 2 CH 2 CO 2 ) 2 Á 3H 2 O; AlCEP] were prepared, characterized and evaluated as selective catalysts in the Baeyer-Villiger oxidation of cyclopentanone, p-methoxybenzaldehyde and 2,4,6-trimethylbenzaldehyde by hydrogen peroxide, in acetic acid. The selectivity of d-valerolactone, p-methoxyphenol and 2,4,6-trimethylphenol have been found to be strongly related with the properties and structure of each catalyst.

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Synthesis and Anti Lipid-Peroxidation Activity of Hydroquinone Monoalkyl Ethers.

Cited by 27 publications

References 0 publications

Effects of Antioxidant 1‐O‐Hexyl‐2,3,5‐trimethylhydroquinone or Ascorbic Acid on Carcinogenesis Induced by Administration of Aminopyrine and Sodium Nitrite in a Rat Multi‐organ Carcinogenesis Model

Effects of Antioxidant 1‐O‐Hexyl‐2,3,5‐trimethylhydroquinone or Ascorbic Acid on Carcinogenesis Induced by Administration of Aminopyrine and Sodium Nitrite in a Rat Multi‐organ Carcinogenesis Model

Antioxidative and 5-Lipoxygenase Inhibiting Activities of Novel Bis(4-hydroxy-2,3,5-trimethylphenoxy)alkyl Derivatives.

Study of Selectivity of Metal Phosphates and Phosphonates in Baeyer–Villiger Oxidations

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