• Title/Summary/Keyword: β-Cyclodextrin

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Ultrasonic Relaxation for Complexation Reaction Between β-Cyclodextrin and Butanoic Acid in Aqueous Solution (사이크로덱스트린과 부탄산의 복합체 형성반응에 의한 초음파 완화)

  • Bae, Jong-Rim
    • The Journal of the Acoustical Society of Korea
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    • v.31 no.2
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    • pp.100-106
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    • 2012
  • The aim of this work was to reveal the effect of butanoic acid in its dissociated form and undissociated form as a guest molecule on the kinetic parameters in an inclusion reaction with ${\beta}$-cyclodextrin (${\beta}$-CD). Ultrasonic absorption measurements in the frequency range from 0.2 to 45 MHz were carried out for ${\beta}$-CD solutions with butanoic acid at $25^{\circ}C$ by ultrasonic relaxation method. The rate and the equilibrium constants were obtained from the guest concentration dependence of the relaxation frequency, and the standard volume change of the complexation reaction were obtained from the maximum absorption per wavelength. A single relaxational absorption was observed, and the cause of the relaxation was attributed to a perturbation of the chemical equilibrium associated with a complexation reaction between ${\beta}$-CD and butanoic acid. These results were compared with those in solutions containing both ${\beta}$-CD and different guest molecules. It was found that the hydrophobicity of guest molecules played an important role in the formation of the inclusion complex and also that the charge on the carboxylic group had a considerable effect on the kinetic characteristics of the complexation reaction.

Low Cholesterol Mozzarella Cheese Obtained from Homogenized and β-Cyclodextrin-Treated Milk

  • Kwak, H.S.;Nam, C.G.;Ahn, J.
    • Asian-Australasian Journal of Animal Sciences
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    • v.14 no.2
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    • pp.268-275
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    • 2001
  • The effects of homogenization conditions and $\beta$-cyclodextrin ($\beta$-CD) on cholesterol removal of Mozzarella cheese were examined. The homogenization pressure influenced markedly on the cholesterol removal in milk and, 75.64% of cholesterol, the highest rate, was removed at $70.0kg/cm^2$. In addition, an increase in temperature resulted in an increase of cholesterol removal in the range of 71.75 to 78.22%. Among different concentrations of $\beta$-CD addition, 1.0% showed 78.21% of cholesterol removal. Therefore, cholesterol-reduced Mozzarella cheese was made by cheese milk treated with 70 $70.0kg/cm^2$ homogenization at $70^{\circ}C$ and 1% $\beta$-CD addition for a subsequent study. The cholesterol reduction of cholesterol-reduced Mozzarella cheese was 63.92%. Meltability, stretchability and oiling-off in cholesterol-reduced cheese were significantly lower than those in control. Hardness, gumminess and chewiness were significantly reduced, while cohesiveness and elasticity increased. Appearance and flavor of the cheese were superior, but texture inferior to the control.

Separation of Madecassoside and Madecassic Acid Isomers by High Performance Liquid Chromatography Using β -Cyclodextrin as Mobile Phase Additive

  • Kai, Guiqing;Pan, Jian;Yuan, Chuanxun;Yuan, Yuan
    • Bulletin of the Korean Chemical Society
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    • v.29 no.3
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    • pp.551-554
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    • 2008
  • An improved HPLC method for the separation of madecassoside isomers (madecassoside and asiaticoside-B) has been developed. The isomers can be separated with high resolution from extracts of Centella asiatica by HPLC using $\beta$-cyclodextrin as a mobile phase added on a $C_{18}$ column. The result shows that the isomers can be separated with a mobile phase consisting of methanol:water (50:50, v/v) with 4 mmol/L $\beta$-CD. To elucidate the mechanism of the separation of madecassoside and asiaticoside-B, this paper studied the separation of their aglycon parts (madecassic acid and terminolic acid), another pair of isomers. The isomers can also be separated with high resolution with a mobile phase consisting of methanol:water (65:35, v/v) with 4 mmol/L $\beta$-CD and the pH of the mobile phase was adjusted to 4. The paper also studied the separation of the two isomers by HPLC using $\alpha$-CD and Glucosyl-$\beta$-CD as a mobile phase additive in order to elucidate the mechanism of the separation process.

Multivariate Optimization of a Sulfated- β-Cyclodextrin-Modified Capillary Zone Electrophoretic Method for the Separation of Chiral Arylalcohols

  • Zhang, Yu-Ping;Noh, Hyun-Joo;Choi, Seong-Ho;Ryoo, Jae-Jeong;Lee, kwang-Pill;Ohta, Kazutoku;Fujimoto, Chuzo;Jin, Ji-Ye;Takeuchi, Toyohide
    • Bulletin of the Korean Chemical Society
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    • v.25 no.3
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    • pp.377-381
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    • 2004
  • Chiral separation of aryalcohols such as 1-phenyl-propanol, 1-phenyl-2-proanol, and 2-phenyl-1-propanol by capillary electrophoresis has been optimized using the overlapping resolution mapping (ORM) scheme. Three critical parameters of the electrophoretic media, i.e. phosphate concentration, sulfated ${\beta}$-cyclodextrin (CD) concentration and pH, were chosen for optimization. The working ranges were initially presumed by 7 preexperiments. Further optimization was carried out by another seven experiments within the narrow working ranges. From the final overlapping resolution mapping all peak pairs, the area of maximum separations were located. Using the conditions of a point in this area, we found that the target compounds were a baseline separated within 30 min. The maximum separation conditions of arylalcohols were a chiral selector concentration of 5.4%, a phosphate concentration of 28 mM, and a pH of 5.0.

Binding Geometry of Inclusion Complex as a Determinant Factor for Aqueous Solubility of the Flavonoid/β-Cyclodextrin Complexes Based on Molecular Dynamics Simulations

  • Choi, Young-Jin;Lee, Jong-Hyun;Cho, Kum-Won;Hwang, Sun-Tae;Jeong, Karp-Joo;Jung, Seun-Ho
    • Bulletin of the Korean Chemical Society
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    • v.26 no.8
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    • pp.1203-1208
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    • 2005
  • A computational study based on molecular dynamics (MD) simulations was performed in order to explain the difference in aqueous solubilities of two flavonoid/$\beta$-cyclodextrin ($\beta$-CD) complexes, hesperetin/$\beta$-CD and naringenin/$\beta$-CD. The aqueous solubility of each flavonoid/$\beta$-CD complex could be characterized by complexwater interaction not by flavonoid-CD interaction. The radial distribution of water around each inclusion complex elucidated the difference of an experimentally observed solubility of each flavonoid/$\beta$-CD complex. The analyzed results suggested that a bulky hydrophobic moiety (-$OCH_3$) of B-ring of hesperetin nearby primary rim of $\beta$-CD was responsible for lower aqueous solubility of the hesperetin/$\beta$-CD complex.

Chiral Separation of Arylalcohols by Capillary Electrophoresis Using Sulfonated β-Cyclodextrin and Ag Colloids as Additives

  • Choi, Seong-Ho;Noh, Hyen-Ju;Lee, Kwang-Pill
    • Bulletin of the Korean Chemical Society
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    • v.26 no.10
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    • pp.1549-1554
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    • 2005
  • Chiral separation of arylalcohols such as 1-phenyl-1-propanol, 1-phenyl-2-propanol, and 2-phenyl-1-propanol by capillary electrophoresis was studied using sulfonated $\beta$-cyclodextrin (CD) as a chiral selector and Ag colloids as an additive. The optimum separation condition of arylalcohols was found to be the chiral selector concentration of 6.5 mM, applied voltage of 15 kV, and pH of 7.0. In order to improve chiral separation, an Ag colloid was mixed with a running buffer. The resolution in the Ag colloid-mixed running buffer was considerably superior to that obtained with the sulfonated $\beta$-CD alone. The molar ratio of sulfonated $\beta$-CD to Ag colloid, which is one of critical parameters affecting resolution, was found to be optimum at 65 : 1. In order to elucidate the resolution mechanism, an inclusion-complex of the arylalcohols with sulfonated $\beta$-CD was prepared by mixing and shaking in solution, and then characterized by cyclic voltammetry (CV). The inclusion mechanism was also discussed using experimental results.

Molecular Modeling of Enantio-discrimination of α-Methoxy-α-trifluoromethylphenylacetic Acid (MTPA) by Cyclomaltoheptaose (β-Cyclodextrin) and 6-Amino-6-deoxy-cyclomaltoheptaose

  • Jung, Eun-Kyoung;Jeong, Karp-Joo;Lee, Sang-San;Kim, Jee-In;Jung, Seun-Ho
    • Bulletin of the Korean Chemical Society
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    • v.24 no.11
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    • pp.1627-1631
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    • 2003
  • Molecular modeling was performed to comprehend the chiral recognition of ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid (MTPA) enantiomers by cyclomaltoheptaose (${\beta}$-cyclodextrin,${\beta}$-CD) and 6-amino-6-deoxy-cyclomaltoheptaose (am-${\beta}$-CD). Monte Carlo (MC) docking coupled to constant temperature molecular dynamics (MD) simulations was applied to the investigation for the ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid complexation with two different CDs in terms of the relative distribution of the interaction energies. The calculated results are finely correlated with the experimental observations in chiral recognition thermodynamics. Am-${\beta}$-CD as a host showed the superior enantio-discrimination ability to the native ${\beta}$-CD where the amino group of am-${\beta}$-CD was critically involved in enhancing the ability of chiral discrimination via the Coulombic interaction with MTPA.

Entrapment of Milk Nutrients during Cholesterol Removal from Milk by Crosslinked β-Cyclodextrin

  • Ha, H.J.;Jeon, S.S.;Chang, Y.H.;Kwak, H.S.
    • Food Science of Animal Resources
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    • v.29 no.5
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    • pp.566-572
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    • 2009
  • This study was designed to elucidate the quantities of milk nutrients entrapped during cholesterol removal from milk by crosslinked $\beta$-cyclodextrin ($\beta$-CD, 0.4~1.2%, w/v) and to evaluate the amounts of the residual $\beta$-CD in cholesterol-reduced milk treated by crosslinked $\beta$-CD. The content of lactose in the control milk (without treatment by crosslinked $\beta$-CD) was 4.86%, and the amounts of lactose entrapped by crosslinked $\beta$-CD ranged from 0.00 to 0.03%. The total amounts of the entrapped short-chain free fatty acid (FFA) and free amino acid (FAA) ranged from 0.03 to 0.09 ppm and from 0.28 to $0.71{\mu}mol/mL$, respectively. The amounts of the entrapped water-soluble vitamins (L-ascorbic acid, niacin, thiamine and riboflavin) ranged from 0.02 to 0.05 ppm, 0.01 to 0.06 ppm, 0.00 to 0.06 ppm and 0.01 to 0.06 ppm, respectively. The entrapped amounts of lactose, short-chain FFAs, FAAs and water-soluble vitamins were not remarkably affected by the concentrations of crosslinked $\beta$-CD (0.4~1.2%, w/v). Only very small amounts of residual $\beta$-CD in the cholesterol-removed milk were measured (1.22~3.00 ppm). Based on the data obtained from the present study, it was concluded that the amounts of entrapped nutrients were negligible during cholesterol removal from milk by crosslinked $\beta$-CD, and only trace amounts of residual $\beta$-CD were present in cholesterol-removed milk.

Gene Cluster Analysis and Functional Characterization of Cyclomaltodextrinase from Listeria innocua (Listeria innocua 유래 cyclomaltodextrinase의 유전자 클러스터 구조 및 효소 특성)

  • Jang, Myoung-Uoon;Jeong, Chang-Ku;Kang, Hye-Jeong;Kim, Min-Jeong;Lee, Min-Jae;Son, Byung Sam;Kim, Tae-Jip
    • Microbiology and Biotechnology Letters
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    • v.44 no.3
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    • pp.363-369
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    • 2016
  • A putative cyclomaltodextrinase gene (licd) was found from the genome of Listeria innocua ATCC 33090. The licd gene is located in the gene cluster involved in maltose/maltodextrin utilization, which consists of various genes encoding maltose phosphorylase and sugar ABC transporters. The structural gene encodes 591 amino acids with a predicted molecular mass of 68.6 kDa, which shares less than 58% of amino acid sequence identity with other known CDase family enzymes. The licd gene was cloned, and the dimeric enzyme with C-terminal six-histidines was successfully produced and purified from recombinant Escherichia coli. The enzyme showed the highest activity at pH 7.0 and 37℃. licd could hydrolyze β-cyclodextrin, starch, and maltotriose to mainly maltose, and it cleaved pullulan to panose. It could also catalyze the hydrolysis of acarbose to glucose and acarviosine-glucose. In particular, it showed significantly higher activity towards β-cyclodextrin and maltotriose than towards starch and acarbose. licd also showed transglycosylation activity, producing α-(1,6)- and/or α-(1,3)-linked transfer products from the acarbose donor and α-methyl glucopyranoside acceptor.

Influence of Feeding β-Cyclodextrin on Reducing the Content of Cholesterol in Pork (돼지고기의 콜레스테롤 함량 감소에 관한 β-Cyclodextrin의 급여효과)

  • Park, Byung-Sung
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.35 no.3
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    • pp.328-334
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    • 2006
  • The main objective of the present study was to determine the effect of dietary ${\beta}-cyclodextrin\;({\beta}CD)$ on reducing the cholesterol content of pork. Twelve swine of 50 kg body weight were randomly distributed into four groups of three heads each and fed experimental diets for 9 weeks until they reached a market weight of 110 kg. They were assigned to the four experimental diets containing 0% (control), 1.5%, 3.0% or 5.0% pure ${\beta}CD$. Daily feed intake, body weight gain and feed efficiency were not significantly different between any of the four group. The plasma total lipid, triacylglycerol and total cholesterol content of the swine in the three ${\beta}CD$-fed groups were significantly (p<0.05) decreased when compared to those in the control group, and were significantly (p<0.05) reduced by 21.80%,55.58% and 27.69%, respectively, in the swine fed on 5% ${\beta}CD$. The cholesterol content of pork belly (mg/100g) was significantly (p<0.05) decreased by 5.33 mg, 12.70 mg and 15.23 mg in the swine maintained on 1.5%, 3.0% and 5.0% ${\beta}CD$, respectively. The cholesterol content of pork belly, when expressed as the rate of reduced cholesterol, was significantly (p<0.05) decreased by 6.44%, 15.36% and 18.42% in groups of 1.5%, 3.0% and 5.0% ${\beta}CD$, respectively, when compared to that of the control group. These results suggest that dietary ${\beta}CD$ may be classified as dietary fiber which can modulate cholesterol metabolism in swine.