• Title/Summary/Keyword: 1,2- diacylglycerol

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Production of Diacylglycerol-Oil from Lipase-Catalyzed Reaction Using Soybean Oil and Glyceryl Monooleate (대두유와 Glyceryl Monooleate의 효소적 반응을 이용한 Diacylglycerol 함유 유지의 생산)

  • Jeon, Mi-Sun;Lee, Cho-Rong;Lee, Ki-Teak
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.38 no.11
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    • pp.1559-1563
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    • 2009
  • Scaled-up production of oil containing diacylglycerol (DAG), so called diacylglycerol-oil, was produced by lipase-catalyzed reaction. Mixture of soybean oil and glyceryl monooleate with 1:2 molar ratio was esterified with Lipozyme RMIM in a batch-type reactor at 55$^{\circ}C$ and 300 rpm during 6 hr. After short-path distillation for removal of monoacylglycerol and free fatty acid as reaction by-products, diacylglycerol-oil mainly consisted of DAG (29 area%) and TAG (71 area%). The major compositional fatty acids in diacylglycerol-oil were oleic (44.36 wt%), and linoleic acids (37.36 wt%). Acid value and iodine value of diacylglycerol-oil were 0.13 and 112.6, respectively. Solid fat content (SFC) of diacylglycerol-oil was observed after differential scanning calorimetry (DSC) analysis in which three melting peaks at -25.0, 0.1, and 11.2$^{\circ}C$ were shown.

Synthesis and Characterization of Mono- and Diacylglycerol Enriched Functional Oil by Enzymatic Glycerolysis of Corn Oil (옥수수유로부터의 효소적 glycerolysis에 의한 monoacylglycerol과 diacylglycerol 함유 기능성 유지 합성 및 특성연구)

  • Park, Rae-Kyun;Lee, Ki-Teak
    • Korean Journal of Food Science and Technology
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    • v.36 no.2
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    • pp.211-216
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    • 2004
  • Mono-and diacylglycerol-enriched oil was produced from corn oil through enzymatic glycerolysis using 1,3-specific immobilized lipase in solvent-free system and stirred-tank batch reactor. HPLC analysis revealed enriched oil was respectively composed of: 45.05, 16.27, 23.05, and 14.98% triacylglycerol, 1,3-diacylglycerol, 1,2-diacylglycerol, and monoacylglycerol; 13.21, 0.15, 2.02, 34.36, 49.12, and 1.14 mol% palmitic, palmitoleic, stearic, oleic, linoleic, and linolenic acids; and 0.014, 0.029, 0.010 and 0.053% ${\alpha},\;{\gamma},\;{\delta}-$, and total tocopherols. Physiochemical and melting properties of enriched oil were evaluated. Oxidative stability study revealed enriched oil showed higher peroxide and p-anisidine values than corn oil. Rosemary extracts (100 to 300 ppm) reduce oxidation.

Enzymatic modification of diacylglycerol with different type of fatty acids (지방산 종류에 따른 Diacylglycerol의 효소적 개질 연구)

  • Lee, Mi-Young;Hong, Soon-Taek;Lee, Ki-Teak
    • Korean Journal of Agricultural Science
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    • v.41 no.2
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    • pp.141-147
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    • 2014
  • Diacylglycerol-oil (DAG oil) and four kinds of fatty acids [C16:0, C18:0, perillar oil-hydrolyzate(C18:3, 59.7%) and docosahexaenoic acid(DHA, C22:6, 63.7%)] were enzymatically esterified with 1:0.5, 1:1 and 1:1.5 molar ratio (DAG oil: fatty acids) to produce structured DAG. The reaction mixture were catalyzed by addition of sn-1,3 specific Lipozyme RMIM with 10 wt% of total substrates, and reacted for 1, 3, 6 and 24 hr at $62^{\circ}C$ with 220 rpm on the shaking water bath. The produced DAG were analyzed by TLC. In the result, the proportion of each fatty acid [(C16:0, C18:0, perilla oil-hydrolysate(C18:3, 59.7%) and DHA(C22:6, 63.7%)] on DAG products were increased as molar ratios of substrate increased. Among them, DHA showed the least reaction rate in which 24.2 % of DHA was found in the structured DAG molecules after 24 hr reaction with 1:1.5 molar substrate amount ratio.

Glucose Release Induced by 1,2-Dioctanoyl-sn-Glycerol in Perfused Rat Liver (관류 흰쥐 간에서 1,2-Dioctanoyl-sn-Glycerol에 의한 글루코오스의 유리작용)

  • Hwang, Young-Eun;Moon, Eun-Soon;Kim, Mie-Young
    • YAKHAK HOEJI
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    • v.35 no.6
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    • pp.509-514
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    • 1991
  • The effect of diacylglycerol on glucose release was studied by using 1,2-dioctanoyl-sn-glycerol ($diC_8$), a cell permeable diacylglycerol, in perfused rat liver. The glucose release was increased by $diC_8(50\;{\mu}M$), and the effect was depended on calcium ions. The increment of glucose release by $diC_8(50\;{\mu}M$) was inhibited by indomethacin ($50\;{\mu}M$); the amount of glucose release was almost the same with that of control group. Arachidonic acid($200\;{\mu}M$) also increased glucose release and the release was inhibited by indomethacin. There was no synergistic effect on glucose release by the combination of $diC_8(50\;{\mu}M$) and phenylephrine($10\;{\mu}M$).

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Conformationally Constrained Analogues of Diacylglycerol Having a Perhydrofuro[3,4-c]furan-1,4-dione Bis-${\gamma}$-butyrolactone Skeleton

  • Lee, Jee-Woo;Nancy-E. Lewin;Peter-M. Blumberg;Victor-E. Marquez
    • Archives of Pharmacal Research
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    • v.21 no.2
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    • pp.164-167
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    • 1998
  • Bis-${\gamma}$-lactones (1,2) having a perhydrofuro[3,4-c]furan-1,4-dione skeleton were designed as conformationally constrained diacylglycerol analogues. They were synthesized from D-apiose in 11 steps, and evaluated as $PKC-{\alpha}$ ligands by measuring their ability to displace bound $^3H$]PDBU from the enzyme. The compounds showed moderate binding affinities with $K_i$ values of 13.89 (${\pm}5.67$) ${\mu}M$ and 11.47 (${\pm}0.89$) ${\mu}M$, respectively. Their similar binding affinities indicate that these two bicyclic compounds were not effectively discriminated by $PKC-{\alpha}$ in terms of the direction of the side chain as other ligands built on similar bis-${\gamma}$-lactones.

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Effect of Dietary Calcium on Cell Proliferation and Colonic Mucosal Levels of Eicosanoid and 1,2-diacylglycerol in Colon Carcinogenesis of Rats (쥐에서 식이 Calcium이 대장 암화관정의 세포증식과 대장점막의 Eicosanoid 및 1,2 -diacylglycerol 수준에 미치는 영향)

  • 김채종
    • Journal of Nutrition and Health
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    • v.31 no.1
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    • pp.21-27
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    • 1998
  • The objective of this study was to observe the effect of dietary calcium(Ca) level on colonic mucosal levels of cell proliferation, 1, 2-diacylglycerol(DAG), TXB2, PGE2 and phospholipid fatty acid composition which have been known as biomarkers for colon cancer. One hundred male Sprague Dawley rats, at 7 weeks of age, were divided into two fat type groups. Each group of which was further divided into two Ca level groups. Each rt was intramuscularly injected with 1, 2,-dimenthylhydrazine(DMH) for 6 weeks (total dose of 180mg/kg body weight) and simultaneously fed one of four experimental diets containing 15% dietary fat(corn oil or perilla oil )and 0.3% or 1.0% Ca by weight for 20 weeks. Compared to corn oil, perilla oil significantly reduced cell proliferation by decreasing labeling index, proliferating zone, crypt length in colonic mucosa and colonic mucosa and colonic mucosal levels of DAG, TXB2 . PGE2 and phospolipid (PL) arachidonic acid distribution. The effect of Ca on biomarketrs was different depending on the type of dietary fat comsumed . Ca effect of Ca on biomarkers was different depending on the type of dietary fat comsumed. Ca effect was not significantly shown in the PO group, but it was significant in the CO group in which high Ca(1.0%) decreased the levels of levels of PL-C20 : 4(%), DAG and PGE2 . However , high Ca supplementation had shown only the trends of improving cell proliferation. Overall , high dietary Ca significantly reduced cell proliferation by inhibiting the synthesis of eicosanoid and DAG with reduced distribution of PL-C20 : 4 , which may have resulted in lower activation of PKC through reduced signal transduction. Since a high level of dietary Ca was more effective in reducing the risk factor against colon cancer in corn oil fed rats, it could be suggested that a higher amount of dietary Ca be consumed , especially when more vegetable oil rich in linoleic acid is included in the diet.

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Inhibitory Activity of Diacylglycerol Acyltransferase by Tanshinones from the Root of Salvia miltiorrhiza

  • Ko, Jeong-Suk;Ryu, Shi-Young;Kim, Young-Sup;Chung, Mi-Yeon;Kang, Jong-Seong;Rho, Mun-Chual;Lee, Hyun-Sun;Kim, Young-Kook
    • Archives of Pharmacal Research
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    • v.25 no.4
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    • pp.446-448
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    • 2002
  • The inhibitory activity of tanshinones from Salvia miltiorrhiza was tested on rat liver diacylglycerol acyltransferase (DGAT). Cryptotanshinone (1) and 15,16-dihydrotanshinone I (3) exhibited potent DGAT inhibitory activities dose-dependently with $IC_{50}$ values of $10.5 {\;}{\mu\textrm{g}}/ml{\;}and{\;}11.1{\;}{\mu\textrm{g}}/ml$. However, tanshinone IIA (2) and tanshinone I (4) showed very weak inhibition ($IC_{50}{\;}value:{\;}>{\;}250{\;}{\mu\textrm{g}}/ml$). A dihydrofuran moiety was seemed to be responsible for the stronger inhibitory activity

Bradykinin-Mediated Stimulation of Phospholipase D in Rabbit Kidney Proximal Tubule Cells

  • Park, Kyung-Hyup;Jung, Jee-Chang;Chung, Sung-Hyun
    • Biomolecules & Therapeutics
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    • v.2 no.1
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    • pp.39-46
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    • 1994
  • The present study was undertaken to demonstrate whether or not bradykinin activates a phospholipase D in rabbit kidney proximal tubule cells. By measuring the formation of [$^3$H]phosphatidic acid and [$^3$H]phosphatidylethanol we could elucidate the direct stimulation of phospholipase D by bradykinin. Bradykinin leads to a rapid increase in [$^3$H]phosphatidic acid and [$^3$H]diacylglycerol, and [$^3$H]phosphatidic acid formation preceded the formation of [$^3$H]diacylglycerol. This result suggests that some phosphatidic acid seems to be formed directly from phosphatidylcholine by the action of phospholipase D, not from diacylglycerol by the action of diacylglycerol kinase. In addition, the other mechanisms by which phospholipase D is activated was examined. We have found that phospholipase D was activated and regulated by extracellular calcium ion and pertussis toxin-insensitive G protein, respectively. It has also been shown that bradykinin may activate phospholipase D through protein kinase C-dependent pathway. In conclusion, we are now, for the first time, strongly suggesting that bradykinin-induced activation of phospholipase D in the rabbit kidney proximal tubule cells is mediated by a pertussis toxin-insensitive G protein and is dependent of protein kinase C.

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Expression Patterns of Bacillus subtilis Diacylglycerol Kinase Gene Induced by Physiological Stimuli (Bacillus subtilis dgk (diacylglycerol kinase) 유전자의 생리적 자극에 의한 유도발현)

  • Lee, Mi-Young;Suh, Seok-Jong;Lee, Jin-Hyung;Song, Bang-Ho;Kim, Jong-Cuk
    • Microbiology and Biotechnology Letters
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    • v.30 no.1
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    • pp.15-20
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    • 2002
  • Diacylglycerol kinase (DGK) phosphorylates the second messenger diacylglycerol (DAG) to phosphatidic acid and it may play a role in signal transduction in Escherichia coli as well as in eukaryotic cells. In addition, DGK is important for microorganisms to adapt to several physiological stimuli. In Bacillus subtilis, the effect of stress on dgk transcription was examined by northern hybridization. The high level of dgk transcription was induced against high osmolarity, low pH value and low temperature. Transcriptional analysis revealed that the dgk gene and dgk upstream locus (ORF2, ORF3 and ORF4) were transcribed as a polycistronic mRNA to form an approximately 2.5 kb transcript.

Production of Diacylglycerol from Lipase by the Catalyzed Reaction of Soybean Oil and Glyceryl Monooleate (Lipozyme TLIM을 효소적 반응촉매로 이용한 glyceryl monooleate로부터의 diacylglycerol의 합성)

  • Jeon, Mi-Sun;Lee, Cho-Rong;Lee, Ki-Teak
    • Korean Journal of Food Science and Technology
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    • v.42 no.2
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    • pp.246-249
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    • 2010
  • Diacylglycerol (DAG) was produced from lipase by the catalyzed synthesis of soybean oil (SBO) and glyceryl monooleate (GMO) with Lipozyme TLIM (Thermomyces lanuginosa). Effects of reaction time, molar ratio and enzyme road were studied. When 2:1, 1:1 and 1:2 (SBO:GMO) molar ratios with 20% Lipozyme TLIM were applied in a 1-hr reaction, the concentrations of DAG produced were 17.8, 20.0 and 20.4 g/100 g oil, respectively. Different amounts (2, 5, 10 and 20%) of Lipozyme TLIM were used at a 1:2 (SBO:GMO) molar ratio, and the concentrations of DAG produced in a 1-hr reaction were 10.8, 14.0, 16.9 and 20.4 g/100 g oil, respectively. During a 72-hr reaction, 10.8-22.7 g/100 g oil of DAG were produced under the reaction conditions in this study.