• Title/Summary/Keyword: $^{1}H$ NMR

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Hygroscopicity of 1:2 Choline Chloride:Ethylene Glycol Deep Eutectic Solvent: A Hindrance to its Electroplating Industry Adoption

  • Brusas, John Raymund;Dela Pena, Eden May B.
    • Journal of Electrochemical Science and Technology
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    • v.12 no.4
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    • pp.387-397
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    • 2021
  • Deep eutectic solvents have been established as feasible metal electroplating solvent alternatives over traditional toxic aqueous plating baths. However, water, either added intentionally or unintentionally, can significantly influence the solvent's physical properties and performance, thereby hindering its industry application. In this study, the hygroscopicity, or the ability to absorb moisture from the environment, of synthesized ethaline (1:2 choline chloride:ethylene glycol) was investigated. The kinematic viscosity, electrical conductivity, electrochemical window, and water content of ethaline were monitored over a 2-week period. Karl Fischer titration tests showed that ethaline exposed to the atmosphere displayed significant hygroscopicity compared to its unexposed counterpart. 1H NMR spectroscopy revealed that water vapor was readily absorbed at the surface due to the hydrophilic groups present in the ethaline molecule. Water uptake resulted in the decrease in viscosity, increase in electrical conductivity and narrowing of the electrochemical window of ethaline. Solution heating at 100℃ removed the absorbed moisture and allowed the recovery of the solvent's initial properties.

Studies on Cysteine desulfhydrase Produced by Bacteria(Part II) Enzymatic Preparation of L-Cysteine Derivatives by Cysteinedesulfhydrase from Aerobacter aerogenes. (Bacteria가 생산하는 Cysteinedesulfhydrase에 관한 연구(제이보) L-Cysteine 유도체의 효소적 합성에 관하여)

  • 최용진;양한철
    • Microbiology and Biotechnology Letters
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    • v.2 no.1
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    • pp.45-50
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    • 1974
  • 1 With cysteinedesulfhydrase (E. C.4.4.1.1.) from Aerobactor aerogenes, an enzyme which catalyzes the stoichiometric conversion of L-cysteine to pyruvate, ammonia and sulfide, reversibility of the degradation of L-cysteine was investigated. It was found that the enzyme also catalized the reverse reaction of $\alpha$, $\beta$-elimination to synthesize L-cysteine derivatives from pyruvate, ammonia and sulfides when large amounts of substrates were added to the reaction mixtures. 2. The synthetic reaction by cysteinedesulfhydrase proceeded linearly with incubation time and enzyme concentrations. The optimal pH for the synthetic reaction was 10.0. 3. The results of the isolation and identification of the products showed that the L-cysteine derivatives synthesized by this enzymatic method were identical with S-methyl-L-cysteine and S-ethyl-L-cysteine respectively.

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Isolation and Identification of Bioactive Compounds from the Tuber of Brassica oleracea var. gongylodes

  • Prajapati, Ritu;Seong, Su Hui;Kim, Hyeung Rak;Jung, Hyun Ah;Choi, Jae Sue
    • Natural Product Sciences
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    • v.26 no.3
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    • pp.214-220
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    • 2020
  • Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH2Cl2), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H2O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH2Cl2 fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of 13C and 1H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.

Purification and Characterization of CDMHK, a Growth Inhibitory Molecule Against Cancer Cell Lines, from Myxobacterium sp. HK1 Isolated from Korean Soil

  • LEE HAN-KI;LEE IN-HYE;YIM JEE-SUN;KIM YONG-HO;LEE SANG-HEE;LEE KISAY;KOO YOON-MO;KIM SANG-JIN;JEONG BYEONG-CHUL
    • Journal of Microbiology and Biotechnology
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    • v.15 no.4
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    • pp.734-739
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    • 2005
  • Myxobacterium sp. HK1, isolated from Korean soil, degrades cellulose, differentiates to fruiting body, and its 16s rDNA has $95\%$ similarity to Polyangium sp. An anticancer molecule, CDMHK, was identified from culture broth of Myxobacterium sp. HK1, and purified by Diaion HP20, Silica gel, Sephadex LH-20 chromatography, and preparative HPLC using an YMC OSD-A C18 column. The molecular structure and formula were determined to be $C_{l2}H_{l9}N_3O_2$ (M.W 237) by MS spectrometry, 300 MHz $^{1}H\;and\;^{13}C$ NMR. The CDMHK was not active against Escherichia coli, Staphylococcus aureus, and Candida albicans. However, this molecule inhibited the growth of various cancer cell lines. The $ED_{50}$ values of CDMHK were determined to be 0.147, 0.086, 0.18, 0.166, and 0.142 $\mu$g/ml against A549, SK-OV-3, SK-MEL-2, VF498, and HCTl5 cancer cell lines, respectively. In addition, the CDMHK was able to induce apoptosis of the CCRF-CEM cancer cell line, evidenced by DNA fragmentation assay and DAPI staining.

Antioxidant and Cytotoxic Activity of Compounds from the Stem of Juncus effusus (등심초로부터 분리된 화합물의 항산화 활성 및 암세포 성장 억제 효과)

  • Kim, Ye Jin;Park, Chan Ik;Park, Jae Sung;Ahn, Eun Mi
    • Journal of Applied Biological Chemistry
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    • v.57 no.1
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    • pp.47-51
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    • 2014
  • The stems of Juncus effusus were extracted with 70% aqueous ethanol and the concentrated extract was partitioned with ethyl acetate, n-butanol and $H_2O$, successively. Two compounds were isolated from the ethyl acetate fraction through the repeated silica gel and Sephadex LH-20 column chromatographies. According to the results of physico-chemical and spectroscopic data including NMR and IR, the chemical structures of the compounds were determined as dehydroeffusol (1) and effusol (2). Dehydroeffusol and effusol exhibited potent scavenging activity for DPPH and ABTS radicals with the $IC_{50}$ values as $130{\pm}3.21$ and $79{\pm}1.53{\mu}M$ in DPPH assay, and as $39{\pm}3.51$ and $24{\pm}2.73{\mu}M$ in ABTS assay, respectively. The compounds also significantly inhibited the proliferation of human cancer cell lines, AGS and A549.

Chemical Modification of Botryosphaeran: Structural Characterization and Anticoagulant Activity of a Water-Soluble Sulfonated ($1{\rightarrow}3$)($1{\rightarrow}6$)-${\beta}$-D-Glucan

  • Brandi, Jamile;Oliveira, Eder C.;Monteiro, Nilson K.;Vasconcelos, Ana Flora D.;Dekker, Robert F.H.;Barbosa, Aneli M.;Silveira, Joana L.M.;Mourao, Paulo A.S.;Silva, Maria De Lourdes Corradi Da
    • Journal of Microbiology and Biotechnology
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    • v.21 no.10
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    • pp.1036-1042
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    • 2011
  • The exopolysaccharide botryosphaeran ($EPS_{GLC}$; a ($1{\rightarrow}3$)($1{\rightarrow}6$)-${\beta}$-D-glucan from Botryosphaeria rhodina MAMB-05) was sulfonated to produce a water-soluble fraction ($EPS_{GLC}$-S) using pyridine and chlorosulfonic acid in formamid. This procedure was then repeated twice to produce another fraction ($EPS_{GLC}$-RS) with a higher degree of substitution (DS, 1.64). The purity of each botryosphaeran sample (unsulfonated and sulfonated) was assessed by gel filtration chromatography (Sepharose CL-4B), where each polysaccharide was eluted as a single symmetrical peak. The structures of the sulfonated and re-sulfonated botryosphaerans were investigated using ultraviolet-visible (UV-Vis), Fourier-transform infrared (FT-IR), and $^{13}C$ nuclear magnetic resonance ($^{13}C$ NMR) spectroscopies. $EPS_{GLC}$ and $EPS_{GLC}$-RS were also assayed for anticoagulation activity, and $EPS_{GLC}$-RS was identified as an anticoagulant.

Emulsifying Properties and Oxidative Stability of Purified Surface-Active Substances from Defatted Rapeseed Cake Extract (탈지 유채박 중 표면활성정제물의 유화특성 및 산화 안정도에 관한 연구)

  • Kim, San-Seong;Lee, Eui-Seok;Lee, Ki-Teak;Hong, Soon-Taek
    • Journal of the Korean Applied Science and Technology
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    • v.33 no.1
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    • pp.155-167
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    • 2016
  • Surface-active substances in defatted rapeseed cake were obtained using a supercritical fluid extraction method. Then, it was purified by removing sinapine in the extract through a series of steps using a mixed solvent: diethyl ether and ethyl acetate (1:1, v/v). Emulsifying properties of purified surface-active substances were investigated, including fat globule size, zeta potentials and creaming stability and its antioxidant activity in emulsion systems were also studied by peroxide value and $^1H$-NMR spectrum. It was found that fat globules in emulsions with purified surface-active substances were much smaller than ones with the unpurified. In addition, as pH of the emulsion lowered and with increasing NaCl concentration in the emulsion, they were observed to increase, which led to worse creaming stability. These properties were reflected in changes of zeta potentials of emulsions. The oxidative stability was better in emulsions with purified surface-active substances than ones with Tween 20 or commercial lecithin, possibly resulted from the existence of sinapic acid in the extract. It was concluded that purified surface-active substances from defatted rapeseed cake could be simultaneously used as emulsifier and antioxidant agent in emulsion system.

Effect of Temperature Abuse on Quality and Metabolites of Frozen/Thawed Beef Loins

  • Kwon, Jeong A;Yim, Dong-Gyun;Kim, Hyun-Jun;Ismail, Azfar;Kim, Sung-Su;Lee, Hag Ju;Jo, Cheorun
    • Food Science of Animal Resources
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    • v.42 no.2
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    • pp.341-349
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    • 2022
  • The objective of this study was to examine the effect of temperature abuse prior to cold storage on changes in quality and metabolites of frozen/thawed beef loin. The aerobic packaged samples were assigned to three groups: refrigeration (4℃) (CR); freezing (-18℃ for 6 d) and thawing (20±1℃ for 1 d), followed by refrigeration (4℃) (FT); temperature abuse (20℃ for 6 h) prior to freezing (-18℃ for 6 d) and thawing (20±1℃ for 1 d), followed by refrigeration (4℃) (AFT). FT and AFT resulted in higher volatile basic nitrogen (VBN) values than CR (p<0.05), and these values rapidly increased in the final 15 d. Cooking loss decreased significantly with an increase in the storage period (p<0.05). In addition, cooking loss was lower in the FT and AFT groups than in the CR owing to water loss after storage (p<0.05). A scanning electron microscope (SEM) revealed that frozen/thawed beef samples were influenced by temperature abuse in the structure of the fiber at 15 d. Metabolomic analysis showed differences among CR, FT, and AFT from partial least square discriminant analysis (PLS-DA) based on proton nuclear magnetic resonance (1H NMR) profiling. The treatments differed slightly, with higher FT than AFT values in several metabolites (phenylalanine, isoleucine, valine, betaine, and tyrosine). Overall, temperature abuse prior to freezing and during thawing of beef loin resulted in accelerated quality changes.

Development of Biologically Active Compounds from Edible Plant Sources-VIII. - Isolation of Platelet Aggregation Inhibitory Compounds from the Arils of Euphoria longana L. - (식용 식물자원으로부터 활성물질의 탐색-VIII. - 용안육(Euphoria longana L.)으로부터 분리된 uridine의 혈소판 응집 저해 효과 -)

  • Kim, Dong-Hyun;Song, Myoung-Chong;Choi, Jung-Min;Kim, Sung-Hoon;Kim, Dae-Keun;Chung, In-Sik;Park, Mi-Hyun;Kwon, Byoung-Mog;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.47 no.1
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    • pp.130-134
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    • 2004
  • The arils of Euphoria longana L. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$. From the n-BuOH fraction, four compounds were isolated through the repeated silica gel, ODS and Sephadex LH-20 column chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 1,1-dimethyl-2propenyl $1-O-{\beta}-D-glucopyranoside$, ethyl ,${\beta}-D-glucopyranoside$, 5-(hydroxymethyl)-2-furfur-aldehyde and uridine. Uridine exhibited inhibition effect of 79% on platelet aggregation at the concentration of$5\;{\mu}g/ml$.

Synthesis and Characterization of Tetranuclear Molybdenum(Ⅵ) Complexes with Butylamidoxime Derivatives (부틸아미드옥심 유도체의 몰리브덴(Ⅵ) 사핵 착물의 합성과 성질)

  • Roh, Soo-Gyun;Oh, Sang Oh
    • Journal of the Korean Chemical Society
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    • v.39 no.7
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    • pp.552-558
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    • 1995
  • The tetranuclear complexes, $X_2[M_{O4}O_12{R'C(NH_2)NO}_2](X= n-Bu_4N^+$, $R'=(CH_3)_2CH$, $CH_3CH_2CH_2$, $CH_3SCH_2$; $X=(CH_3)_2CHC(=NH_2)NH_2^+$, $R'=(CH_3)_2CH$; $X = CH_3CH_2CH_2C(=NH_2)NH_2^+$, $R'=CH_3_CH_2CH_2$; $X=CH_3SCH_2C(=NH_2)NH_2^+$, $R'=CH_3SCH_2)$ have been synthesized by the reactions of monomeric and polynuclear complexes with isobutyl-, butyl- and thiomethylacetamidoxime. The prepared complexes were identified by elemental analysis, infrared, $^1H$ NMR and $^{13}C$ NMR spectroscopy. The structure of complex ${(CH_3)_2CHC(NH_2)_2}_2[M_{O4}O_{12}{(CH_3)_2CHC(NH_2)NO}_2]$ was determined by X-ray single crystal diffraction. Crystal data are follows: Monoclinic, $P2_{1/c}$, $a=10.168(3){\AA}$, $b=11.768(1){\AA}$, $c=13.557(1){\AA}$, ${\beta}=102.08(1)^{\circ}$, $V=1586.2(5){\AA}^3$, Z=2, final R=0.026 for 2951($F_0>3s(F_0)$). This complex is composed of a planar cyclic $[Mo_4({\mu}-O)_4]$ and two ${\mu}_4$-amidoximate.

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