• Title/Summary/Keyword: c-10,c-12 isomer

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Effect of Biologically Active Isomers of Conjugated Linoleic Acid on Immune Response and Body Composition in Mice (Mice에서 CLA의 생물학적 활성이성체의 투여가 면역반응과 체구성에 미치는 영향)

  • 최미현;김진영;이병한;임좌진;정재홍;정병현
    • Journal of Veterinary Clinics
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    • v.20 no.1
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    • pp.66-73
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    • 2003
  • Numerous physiological effects are attributed to conjugated linoleic acid(CLA). The purpose of this study is to consider these effects with respect to the cis-9, trans-11 and trans-10, cis-12 CLA isomer. Both isomers are natural products. The c9,t11-CLA isomer is the principal dietary form of CLA, but the concentrations of this isomer and the t10,c12-CLA Isomer in dairy products or beef vary depending on the diet fed to cows or steers, respectively. The influence of dietary CLA isomers on the immune response was examined, body weight and weight ratio of organ to body of Balb/C mice. Mice were divided into four groups of 8 mice. Balb/C mice were fed the experimental diets supplemented with 1% CLA (c9,t11-CLA isomer : t10,c12-CLA isomer = 2:3) (Group 1), 1% CLA (c9,t11-CLA isomer t10,c12-CLA isomer : 1:1) (Group 2), 1% safflower oil (Group 3) or nothing (Control) for 3 weeks. After 3 weeks, serum, gut lumen lavage, fat, liver, spleen and thymus were taken. Measurement of total immunoglobulin were executed using sandwich ELISA. Serum levels of IgA and IgM showed that group fed with t10,c12-CLA isomer significantly were higher than group fed with c9,tl1-CLA isomer. In addition serum level of IgG showed that group fed with t10,c9-CLA isomer significantly were lower than group fed with c9,tl1-CLA isomer. However, no significantly differences were observed in the serum IgE and secretory IgA. Weight ratio of spleen to body showed no significant differences. In weight ratio of liver and thymus to body, tl0,c9-CLA isomer significantly were respectively higher than group fed with c9,t11-CLA isomer. In weight ratio of fat to body, tl0,c9-CLA isomer significantly were respectively lower than group fed with c9,tl1-CLA isomer. In conclusion, t10,c12-CLA isomer produced a situation favorable for immunopotentiative effect and body composition. But it should be protected against hepatomegaly induced lipid accumulation in liver.

Effect of Dietary CLA Isomers on Apoptosis and Cell Proliferation in Colonic Mucosa of DMH-Treated Rats (식이에 첨가한 CLA Isomer가 쥐에서 대장점막의 세포사멸과 세포증식에 미치는 영향)

  • 박현서;권필수;윤정한;하영래
    • Journal of Nutrition and Health
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    • v.36 no.7
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    • pp.661-666
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    • 2003
  • The study was designed to compare the anti-carcinogenic effect of conjugated linoleic acid (CLA) isomers on colon carcinogenesis in 1,2-dimethylhydrazine (DMH)-treated rats by determining the levels of apoptosis, cell proliferation, eicosanoids and 1,2-diacylglycerol (DAG) in colonic mucosa. Sixty male Sprague Dawley rats were randomly divided into 3 groups depending on the types of CLA isomers, i.e. BT group (no CLA contained), CLA-C group (cis-9, trans11 isomer contained), and CLA- T group (trans-10, cis-12 isomer contained). The experimental diet was composed of protein at 20%, carbohydrate at 56.2%, and fat at 14.5% including 0.8% CLA isomers by weight. The experimental diet was fed for 14 weeks with the initiation of intramuscular injection of DMH, which was injected twice a week for 6 weeks to give total dose of l80mg per kg body weight. Two CLA isomers (c9t11 and t10c12) significantly increased the relative percentage of apoptosis but reduced cell proliferation in mucosal cell and also the levels of PGE$_2$, TXB$_2$, and DAG in colonic mucosa. However, there was no significant differences in anti-carcinogenic effect between c9t11 isomer and t10c12 isomer. Overall, colon carcinogenesis could be significantly inhibited by CLA isomers by increasing apoptosis and reducing cell proliferation, the levels of eicosanoids and DAG in colonic mucosa.

Distribution and Content of Geometric Isomers of Conjugated Linoleic Acid in Dairy Foods from the Quebec Province of Canada

  • Park, Seung-Yong;Ahn, Jae-Eun;Kim, Geun-Bae;Jung, Mun-Yhung;Lee, Byong-H.
    • Food Science and Biotechnology
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    • v.17 no.1
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    • pp.31-37
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    • 2008
  • The distributions and content of geometrical isomers of conjugated linoleic acids (CLA) in dairy foods such as milk, yogurt, and cheese, produced or being sold in the Quebec province of Canada, were investigated by gas chromatographic analysis. The mean contents of total CLA (mg/g fat) were $5.06{\pm}0.74$ in 4 low-fat milk samples, $14.14{\pm}4.95$ in 6 yogurt samples, and $18.22{\pm}7.89$ in 5 natural ripened cheeses. Among the yogurt samples, YY contained the highest content of total CLA ($20.68{\pm}5.17\;mg/g$ fat). Among the cheese samples, Gruyere contained the highest amount of total CLA ($29.86{\pm}0.62$) as well as c-9,t-11 ($22.03{\pm}0.36\;mg/g$ fat), followed by Jarlsberg ($22.76{\pm}0.14$), Provolone ($16.42{\pm}0.52$), Cheddar ($13.83{\pm}0.81$), and Swiss ($8.23{\pm}1.11$). Based on the distribution ratios of CLA isomers in these dairy foods, the c-9,t-11 isomer appeared to be the major CLA isomer in both the low-fat milk ($89.87{\pm}2.39%$) and yogurt ($90.98{\pm}4.42%$). In the cheeses, however, the ratio of c-9,t-11 ($54.86{\pm}13.06%$) was slightly higher than that of c-10,c-12 ($40.81{\pm}13.40%$).

Antioxidative Effectiveness and Oxidized Products in Mixture of Methyl Linoleate and Phenolic Compounds (Methyl Linoleate에 대한 Phenol성 물질의 항산화성과 산화 생성물)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.379-385
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    • 1993
  • Antioxidative effectiveness and oxidized products in mixture of methyl linoleate(ML) and phenolic compounds were investigated under oxygen blowing at $37^{\circ}C$ for 9 days. Caffeic acid (3,4-dihydroxy cinnamate ; CML) and phloroglucinol(1,3,5-trihydroxy benzene ; PML) showed higher antioxidative effectiveness for methyl linoleate than 0.05% ${\alpha}-tocopherol$ (TML). Oxidized products in ML group were methyl 8-(2-furyl)-octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In CML group the oxidized products were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer and 9-trans, trans hydroperoxide isomer, but 13-hydroxy isomer was not identified. It was shown that CML were oxidized more slowly than ML group and at 6th day of oxidation, caffeic quinone was found to be major oxidized product of caffeic acid. Oxidixed Products in PML group were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer, and 9-trans, trans hydroperoxide isomer but phloroglucinol was not oxidized even at the 9th day of reaction.

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Effect of Conjugated Linoleic Acid(CLA) on Proliferation and Differentiation of Porcine Adipocyte and Muscle Cell (Conjugated Linoleic Acid(CLA)가 돼지 지방세포와 근육세포의 증식과 분화에 미치는 영향)

  • Chung, C.S.;Kim, H.R.;Kang, J.N.;Kim, N.S.
    • Journal of Animal Science and Technology
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    • v.49 no.1
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    • pp.25-32
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    • 2007
  • The current study was undertaken to determine the effect of conjugated linoleic acid(CLA) isomers, cis-9, cis-11(c9c11), cis-9, trans-11(c9t11), trans-9, trans-11(t9t11), trans-10, cis-12(t10c12) on differentiation of pig preadipocytes and myogenic satellite cells during culture. Cells were isolated from new born pigs. The t10c12 isomer decreased differentiation of pig preadipocytes(92%), but not that of myogenic cells. The t9t11 isomer decreased differentiation of preadipocytes(14%) and increased that of myogenic cells (26%). No other CLA isomers affected differentiation of preadipocytes or myogenic cells. The effects of CLA on proliferation of preadipocytes and myogenic cells were small, compared to the effects on differentiation. These results suggest that CLA isomers have different effects on differentiaton of pig preadipocytes and myogenic cells.

Oxidation Mechanism of Methyl Linoleate with ${\alpha}-Tocopherol$ (${\alpha}-Tocopherol$이 첨가된 Methyl Linoleate의 산화물 생성 기구)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.6
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    • pp.614-619
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    • 1993
  • Oxidation mechanisms of methyl linoleate with ${\alpha}-Tocopherol$(TML) were investigated by determining oxidized products using GC-MS during oxidation at $37^{\circ}C$ for 9 days. Oxidized products of TML were found to be methyl octanoate, methyl-8-(2-furyl)-octanoate, 9,13-trans, cis isomer and 9,13-trans, trans isomer. In previous report, oxidation products of methyl linoleate(ML) were methyl-8-(2-furyl)octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In the case of ML, 9-TMSO-12,13-epoxy-l0-octadecenoate was produced instead of methyl octanoate in TML. ${\alpha}-Tocopherol$ quinone, as a major oxidized product of ${\alpha}-Tocopherol$ was formed at the 6th day of oxidation. ${\alpha}-Tocopherol$ quinone was produced rather quickly in lipid media than aqueous media. In oxidation of methyl linoleate, it was shown that the first oxidized product was methyl-9,13-hydroxy-octadecadienoate. As second products, methyl-8-(2-furyl)-octanoate, 9-TMSO-12,13-epoxy-10-octadenoate, and methyl octanoate were oxidized from methyl-9-hydroxy-10-trans, 12-trans-octadecadienoate.

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Transformation for 1,3-Dichloropene of Soil Fumigant in Water and Soil (토양 훈증제 1,3-Dichloropene의 물 및 토양 중 분해)

  • Kim, Jung-Ho
    • Journal of Environmental Science International
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    • v.16 no.12
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    • pp.1463-1468
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    • 2007
  • Emission of methyl bromide(MeBr) of soil fumigant was implicated in stratospheric ozone depletion. To determine the environmental fate for 1,3-dichloropene(1,3-D) of alternatives fumigants for MeBr, this paper researched the transformation for 1,3-D in water and soil. Half lives of cis-1,3-D in water with first-order kinetics are 9.9day and 1.7day at $25^{\circ}C\;and\;40^{\circ}C$, half lives of trans-1,3-D are 8.6day and 1.5day at $25^{\circ}C\;and\;40^{\circ}C$, respectively. Transformation for 1,3-D in water at high temperature faster then at low temperature. Hydrolysis for 1,3-D in water are unaffected at $pH\;2.5{\sim}pH\;10.0$, but hydrolysis for 1,3-D at pH 11.5 higher then at $pH\;2.5{\sim}pH\;10.0$. Half lives of cis-1,3-D in soil are 11.5day and 7.7day at 3% and 10% of soil moisture, half lives of trans-1,3-D are 9.9day and 6.9day at 3% and 10% of soil moisture, respectively. Transformation for 1,3-D in water increased with increasing soil moisture. Transformation for trans-1,3-D isomer are more rapid then cis-1,3-D isomer in water and soil. This research has identified that transformation for 1,3-dichloropropene are affected by temperature, pH, soil moisture, and isomer of cis and trans in water and soil.

The Synthesis and Characterization of Some Novel Thioethers: Thio-Subsituted [3]Cumulenes, -1-Buten-3-ynes and Buta-1,3-dienes

  • Ibis, Cemil;Sahin, Aysecik
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2255-2260
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    • 2010
  • In this study, some novel thiosubstituted butenyne (3a-d, 7b, 15b), butadiene (4a-b, 4d, 5a, 5c, 6b, 8e, 9c, 10b, 16b, 18e) and [3]cumulene (11a-b with isomer 3a-b, 12a with isomer 13a, 14b, 17e) compounds were synthesized from the reaction of 2H-pentachloro-1,3-butadiene with thiols. The new compounds were characterized by elemental analysis, mass spectrometry, UV-vis, IR, 1H NMR, NMR ($^{13}C$ or APT) spectroscopy.

The Effect of Conjugated Linoleic Acid Isomers on the Cell Proliferation, Apotosis and Expressions of Uncoupling Protein (Ucp) Genes during Differentiation of 3T3-L1 Preadipocytes (Conjugated Linoleic Acid 이성체가 3T3-L1 지방전구세포 분화중 세포증식, 세포사멸 및 Ucp 유전자 발현에 미치는 영향)

  • Kwon So-Young;Kang Keum-Jee
    • Journal of Nutrition and Health
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    • v.37 no.7
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    • pp.533-539
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    • 2004
  • It has been reported that CLA decreases fat deposition in vivo and in vitro experiments. Among CLA isomers, c9t11 and t10c12 have been shown to exert active biological activities. For example, t10c12 reduces body weight and increases lean body mass, whereas, c9t11 has little effect on body fattness. However, the underlying molecular mechanism for the anti-obesity action of CLA isomers are not well understood. The purpose of this study was to examine the effects of t10c12 and c9t11 on lipid accumulation, cell proliferation, cell death and the expression levels of Ucp genes which are proposed as targets for anti-obesity in 3T3-L1 preadipocytes. Isomers of CLA at 50$\mu$M were added into preadipocyte differentiation medium for 3, 6 and 9days. Control cells received only the vehicle in the differentiation medium. Cytochemical analyses for lipid accumulation, cell proliferation and apotosis were carried out to compare lipidogenesis and cellular activity. RT-PCR analysis of GAPDH, Ucp 2,3 and 4 were also performed to find any modulatory effects of CLA isomers on the metabolic genes. Lipid accumulation indicated by Oil Red-O staining was inhibited in CLA isomers as compared to the control. T10c12 isomer showed less lipidogenesis than c9t11 did. A decrease occurred in CLA isomers as shown by BrdU incorporation. Apotosis has occured at higher level in t10c12 when compared to that of t9c11. Ucp 2, 3 and 4 genes were also upregulated in CLA isomers. T10c12 showed higher level of Ucp gene expressions than the c9t11 did. The biological activities of CLA isomers were also found to be different during differentiation of 3T3-L1 preadipocytes, suggesting that different isomers may be active in certain stage of lipidogenesis. The results indicate that both c9t11 and t10c12 CLA isomers decrease lipidogenesis, inhibit cell proliferation, increase cell death and upregulate in Ucp gene expressions during 3T3-L1 preadipocyte differentiation. T10c12 isomer was more effective than c9t11 in overall anti-obesity activity.

Antioxidant Effect of Tocopherols and Tocotrienols and cis/trans-, trans/trans-Hydroperoxide Isomer from Linoleic Acid Methylester (토코페롤류의 항산화작용과 Linoleic Acid Methylester에서 생성된 cis/trans-, trans/trans-Hydroperoxide Isomer)

  • Lee, Hyung-Ok
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.307-312
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    • 1993
  • Antioxdant effect was studied in model system with linoleic acid methylester and tocochromanols $({\alpha}-,\;{\beta}-,\;{\gamma}-,\;{\delta}-tocopherol\;and \;{\alpha}-,\;{\gamma}-,\;{\delta}-tocotrienol)$ under definite autoxidation condition-temperature $(40,\;60,\;80^{\circ}C),\;O_2\;(0,\;10,\;20%\;O_2\;in\;N_2)$. 13-Hydroperoxy-9-cis-11-trans-, 13-hydroperoxy-9-trans-11-trans-, 9-hydroperoxy-10-trans-12-cis-, 9-hydroperoxy-10-trans-12-trans-octadecadienoic acid methylester as the major oxidation product were produced from linoleic acid methylester by autoxidation, analyzed with HPLC and antioxidant activities were compared by their quantitative changes. Experimental results showed that all added tocochromanols except ${\alpha}-tocotrienol$ had antioxidant effect at $60^{\circ}C$, and also ${\alpha}-tocopherol$, ${\alpha}-tocotrienol$ and ${\delta}-tocotrienol$ had prooxidant effect at $80^{\circ}C$. And cis/trans-hydroperoxide was predominantly produced at $40^{\circ}C$, but trans/trans-hydroperoxide at $80^{\circ}C$. Except no reproductive experimental data in produced hydroperoxides amount, the production ratio of cis/trans-:trans/trans-hydroperoxides in the autoxidation condition of range from $40^{\circ}C/10%,\;O_2\;to\;60^{\circ}C/20%\;O_2$ were as follows: ${\alpha}-T>{\alpha}-T_3>{\gamma}-T>{\beta}-T>{\gamma}-T_3>{\delta}-T>{\delta}-T_3$. This result showed that ${\alpha}-tocopherol$ among tocochromanols had the lowest antioxidant effect.

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