The antioxidant acitivity of 2,6‐dimethyl‐3,5‐diethoxycarbonyl‐1,4‐dihydropyridine in edible oils

Kouřimská, Lenka; Pokorný, Jan; Tirzītis, G.

doi:10.1002/food.19930370121

Cited by 21 publications

(14 citation statements)

References 2 publications

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“…Dihydropyridine is a new multifunctional antioxidant in food (Kouřimská et al, 1993;Smagin, 1998;Tirzitis and Kirule, 1999;Pánek et al, 2000;Tirzitis et al, 2001). It has been shown that dihydropyridine has the antioxidant and immunological activity in ducks (Bakutis and Bukis, 1984) and chickens (Valdman et al, 1990).…”

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confidence: 99%

Effects of dietary dihydropyridine supplementation on growth performance and lipid metabolism of broiler chickens

Niu¹,

Liu²,

Min³

et al. 2010

CZECH J ANIM SCI

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An experiment was conducted to investigate the effects of dihydropyridine supplementation on growth performance and lipid metabolism of broilers. A total of 480 one-day-old female Arbor Acres broiler chicks were randomly divided into four groups, each group had six replications of 20 birds. Each group was fed a maize-soybean meal diet supplemented with 0, 100, 200, 300 mg/kg dihydropyridine, respectively, for six weeks. At 42 days of age, body weight and feed intake were not affected by dihydropyridine, while feed efficiency was significantly increased by 8.4%, 15.0% and 12.0%, respectively (P < 0.05). The percentage of abdominal fat and the percentage of liver fat were reduced by 24.5%, 25.9%, 23.3%, and 23.6%, 26.7%, 26.0%, respectively (P < 0.05). The higher level of dietary dihydropyridine (200 or 300 mg/kg) increased the hormone-sensitive triglyceride lipase activity in liver and abdominal fat (P < 0.05). The lipoprotein lipase activity in abdominal fat was significantly decreased by dihydropyridine (P < 0.05). The activity of glucose-6-phosphate dehydrogenase and malic dehydrogenase in liver was significantly reduced, whereas the isocitrate dehydrogenase activity in liver was not affected by dietary dihydropyridine. The content of cAMP was significantly increased by dihydropyridine, but malondialdehyde content was decreased (P < 0.05). Dihydropyridine at doses of 100 and 200 mg/kg increased apolipoprotein B (P < 0.05), but 300 mg/kg dihydropyridine had no effect on apolipoprotein B compared with the control group. Triiodothyronine was significantly increased by dietary dihydropyridine (P < 0.05). There were no differences in apolipoprotein A, cholesterol, trigly-cerides, high density lipoprotein-cholesterol, very low density lipoprotein-cholesterol, thyroxine and insulin among dietary treatments. It is concluded that supplementing dihydropyridine has a beneficial effect on feed efficiency and lipid metabolism of broilers, and that 200 mg/kg dihydropyridine supplementation is the optimum dose.

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Effects of dietary dihydropyridine supplementation on growth performance and lipid metabolism of broiler chickens

Niu¹,

Liu²,

Min³

et al. 2010

CZECH J ANIM SCI

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“…1 H NMR spectrum, δ, ppm (J, Hz): 6.08 (1H, s, CH α-pyrone); 5.75 (1H, s, NH); 5.61 (1H, d, 3 J = 9.6, CH vinyl); 5.04 (1H, d, 3 J = 9.6, CH dihydropyridine); 3.75 (3H, s, OCH 3 ); 2.28 (3H, s, CH 3 ); 2.24 (3H, s, CH 3 ); 2.23 (3H, s, CH 3 α-pyrone); 1.54 (9H, s, CH 3 tert-butyl). 13 2-propyl-1,4-dihydropyridine-3,5-dicarboxylate (6c). Pale-yellow solid, 46% yield; mp 52-54°C; FT-IR, , cm -1 : 3340 (NH), 3095, 2961, 2871, 1737, 1695, 1627, 1550, 1490, 1300, 1201, 1106, 859, 777.…”

Section: Synthesis Of Asymmetrical 14-dhps (General Method)mentioning

confidence: 99%

“…The reactions were completed within 0.5-1 h, and 1,4-DHPs 4a-f were obtained in 39-61% yields. The structures of compounds 4a-f were established from FT-IR, 1 H NMR, 13 C NMR, mass spectra, and elemental analyses. 3,4 a-c R = Me, a R 1 = OMe, b R 1 = OEt, c R 1 = OBu-t; d R = n-Pr, R 1 = OEt; e, f R = Me, e R 1 = Me, f R 1 = Ph Also, the reaction of aldehyde 2 with β-dicarbonyl compounds 3b-g in the presence of enamino esters and ketones such as methyl 3-aminobut-2-enoate 5a, 4-aminopent-3-en-2-one 5b, and 3-amino-1-phenylbut-2-en-1-one 5c was investigated and unsymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-DHPs 6a-l were obtained in 21-46% yields (Scheme 3).…”

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confidence: 99%

Synthesis and calcium channel antagonist activity of new symmetrical and asymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines

Shahrisa

Zirak

Mehdipour

et al. 2011

Chem Heterocycl Comp

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were obtained in moderate to good yields at room temperature. The calcium channel blocking activity of these compounds was assessed. They demonstrated moderate to weak effects, although one compound had a comparable effect (IC 50 =1.40×10 -7 M) with respect to the reference drug Nifedipine. The 4-aryl-substituted 1,4-dihydropyridines (1,4-DHPs) are among the most studied heterocyclic compounds that present interesting pharmacological and biological properties [1-4]. They have been used as organic calcium channel modulators [5-7], anticonvulsant [8], antidiabetic [9], antiviral [10], radioprotective [11], antitumor [12], antioxidant [13], vasodilator [14], and anti-inflammatory agents [15]. It was proposed that calcium channel modulation depends on the absolute configuration at C-4 and flexibility of both the ester group of 1,4-DHPs and the C-4 aryl group of these compounds [16,17]. Therefore, the development of new synthetic methods leading to 1,4-DHPs with different substituents [18−20] or heterocycles [21][22][23][24][25][26][27] has attracted much attention in organic synthesis. The Hantzsch synthesis is a classical method for the preparation of 1,4-DHPs [28] and has been one of the most important basic reactions in organic chemistry for its use in pharmaceutical synthesis. However, due to the drastic reaction conditions, long reaction times, and low yields, the classical Hantzsch reaction was modified by several methods [29].

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“…Dihydropyridine is a new multifunctional antioxidant in food (Kourimska et al, 1993;Smagin, 1998;Tirzitis & Kirule, 1999;Panek et al, 2000;Tirzitis & Hyronen, 2001 dihydropyridine showed antioxidant and immunological activities in ducks (Bakutis & Bukis, 1984) and chickens (Val-Dman et al, 1990). Dihydropyridine improved the health of cows, improved the quality of milk and increased cow fertility (Sutkevicius et al, 1984).…”

Section: Introductionmentioning

confidence: 99%

Effects of dietary dihydropyridine on laying performance and lipid metabolism of broiler breeder hens

Niu¹,

Min²,

Wang³

et al. 2011

SA J. An. Sci.

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________________________________________________________________________________ AbstractThe experiment was conducted to investigate the effects of dihydropyridine supplementation on the laying performance and lipid metabolism of broiler breeder hens. A total of 720 forty-five week old broiler breeder hens were randomly divided into four experimental groups, each group consisting of six replicates of 30 birds. For 10 weeks the birds were fed a maize-soybean meal diet containing 0, 100, 200, 300 mg dihydropyridine/kg, in the respective treatment groups. The daily egg weight and daily feed intake were not affected by dihydropyridine supplementation, but the laying rate and feed efficiency were significantly increased. The percentage of abdominal fat and percentage of liver fat were significantly decreased by dietary dihydropyridine. A level of 100 mg dihydropyridine/kg had no effect on the hormone-sensitive triglyceride lipase (HSL) activity in the liver or abdominal fat, though higher levels of dietary dihydropyridine (200 mg/kg or 300 mg/kg) increased HSL activity in the liver and abdominal fat. The concentration of cyclic adenosine monophosphate (cAMP) and superoxide dismutase activity were significantly increased by dihydropyridine, but the malondialdehyde content decreased. The apolipoprotein B concentration was increased at levels of 100 and 200 mg dihydropyridine/kg, but the 300 mg level had no effect on apolipoprotein B, compared with the control group. The triiodothyronine concentration was significantly increased by dietary dihydropyridine. It is concluded that supplementing dihydropyridine in the diet has a beneficial effect on the laying performance and regulates the fat metabolism of broiler breeder hens. The results suggest that the supplementation of 200 mg dihydropyridine/kg diet is the optimal dose for broiler breeder hens. ________________________________________________________________________________

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The antioxidant acitivity of 2,6‐dimethyl‐3,5‐diethoxycarbonyl‐1,4‐dihydropyridine in edible oils

Cited by 21 publications

References 2 publications

Effects of dietary dihydropyridine supplementation on growth performance and lipid metabolism of broiler chickens

Effects of dietary dihydropyridine supplementation on growth performance and lipid metabolism of broiler chickens

Synthesis and calcium channel antagonist activity of new symmetrical and asymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines

Effects of dietary dihydropyridine on laying performance and lipid metabolism of broiler breeder hens

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