• Title/Summary/Keyword: $^{1}H$ NMR

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Preparation and Characteristics of Calcium Lactate from Black Snail

  • Lee, Ye-Kyung;Kim, Soon-Dong
    • Preventive Nutrition and Food Science
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    • v.8 no.2
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    • pp.166-172
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    • 2003
  • Calcium lactate (CL) prepared from powdered black snail (PBS) or its ashed powder (ABS), was investigated for ideal manufacturing conditions to optimize color, solubility and sensory quality. Based on the amount of PBS and 100 mL lactic acid (LA), the yields of PBS-CL were 300% and 15 g in 10% LA and 260% and 20 g in 20% LA. Yields of ABS-CL based on the amount ABS and 100 mL LA were 400% and 60 g in 10% LA and 329% and 66 g in 20% LA. Both of the yields were decreased with an increase of the LA concentration on the basis of PBS and ABS amounts, but proportionally increased with the increment in the LA concentration on the basis of LA volume. Optimal preparation times of the dehydrated PBS-CL and ABS-CL were, respectively, 4 hr and 5 hr at 10$0^{\circ}C$, 3 hr and 4 hr at 12$0^{\circ}C$, and 1 hr and 2 hr at 15$0^{\circ}C$, which showed shorter time in preparing the dehydrated ABS-CL. PBS-CL and ABS-CL were confirmed to be Ca($CH_3$CHOH$CO_2$)$_2$ by the analysis results of IR and $^1$H-NMR. Calcium contents of the anhydrous PBS-CL and ABS-CL were individually 15.4% (w/w) and 17.3% (w/w) representing 84.2% and 94.5% or each theoretical value. Colors or PBS-CL and ABS-CL were light yellow and light-greenish white each. Solubilities of PBS- CL and ABS-CL in distilled water at pH 3~8 were 5.43 and 6.11 g/100 mL, respectively, which demonstrated higher mean solubilities rather than the 4.74 g/100 mL of standard CL. Solubilities of PBS-CL (3.14~5.03 g/100 mL) and ABS-CL (4.69~6.05 g/100 mL) against soup soy sauce, 3% brine, Soju (Korean distilled liquor), thick soy sauce, grape juice and orange juice were higher than those of standard CL (2.94~5.84 g/100 mL). ABS-CL was believed to have a wide use range due to its low sourness while different applications of PBS-CL in food are expected due to its mild astringent taste and strong savory taste despite its strong bitter taste as estimated by sensory evaluation.

Synthesis of Dendritic Polystyrene-block-Linear Poly(t-butyl acrylate) Copolymers by an Amide Coupling (아미드 커플링을 통한 덴드리틱 Polystyrene-Block-Linear Poly(t-butyl acrylate) 공중합체의 합성)

  • Song, Jie;Cho, Byoung-Ki
    • Polymer(Korea)
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    • v.33 no.2
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    • pp.158-163
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    • 2009
  • In this study, we synthesized a series of dendritic polystyrene-b-linear poly (t-butyl acrylate) copolymers with well-defined molecular architectures. The hydroxyl group located at the focal point of the second generation dendron bearing polystyrene ($M_n$ = 1000 g/mol) peripheries was converted into amine group via the following stepwise reactions: 1) tosylatoin, 2) azidation, and 3) reduction. On the other hand, the linear poly (t-butyl acrylate)s were prepared by an atom transfer radical polymerization (ATRP) of t-butyl acrylate where benzyl 2-bromopropanoate and Cu(I)Br/PMDETA were used as initiator and catalyst, respectively. To convert the end group of prepared poly (t-butyl acrylate) s into carboxylic acid, a debenzylation was performed using Pd/C catalyst under $H_2$ atmosphere. In the final step, dendritic-linear block copolymers were obtained through a simple amide coupling reaction mediated by 4-(dimethylamino) pyridine(DMAP) and N,N'-diisopropylcarbodiimide(DIPC). The resulting diblock copolymers were shown to have well-defined molecular weights and narrow molecular weight distributions as supported by $^1H$-NMR spectroscopy and gel permeation chromatography(GPC).

Synthesis and Characterization of Collagen Peptide Based Copolymer from Shaving Scrap (셰이빙 스크랩으로부터 콜라겐 펩타이드계 공중합체 합성과 특성)

  • Park, Min Seok;Shin, Soo Beom;Kim, Ho Soo;Kim, Min Soo;Kim, Ha Sun;Jang, Jae Hyeok;Lee, Jin Kye;Lee, Dong Kuk
    • Applied Chemistry for Engineering
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    • v.33 no.6
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    • pp.581-587
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    • 2022
  • The leather industry generates a large amount of hazardous leather waste of various types every year. Among them, shaving scrap is difficult to recycle because it contains chromium ions. Many studies in recent years have shown that shaving scraps can be processed into various types of valuable products, such as adsorbent, filler, and poultry feed. In this study, collagen peptides were extracted from shaving scraps and structurally modified to be developed as new materials with improved physicochemical properties. First, the chromium ions contained in the shaving scraps were removed using a sodium hydroxide solution, and purified through concentration and low-temperature crystallization. The purified collagen peptide was used to prepare the powder using a spray dryer. The extracted collagen peptides were structurally modified by introducing double bonds by reacting with methacrylic anhydride (MAA), and the product was confirmed by 1H NMR spectroscopy. Next, a copolymer was prepared by redox polymerization of the modified collagen peptide (MCP) and 2-ethylhexyl acrylate (2-EHA). The structure of the copolymer was qualitatively confirmed by FT-IR. In conclusion, this study confirmed that collagen peptides can be extracted from shaving scrap and converted into new eco-friendly materials through certain treatments.

Glycerides from the Aerial Parts of Garland (Chrysanthemum coronarium L.) and Their Inhibitory Effects on ACAT, DGAT, FPTase, and $\beta$-Secretase

  • Song, Myoung-Chong;Yang, Hye-Joung;Cho, Jin-Gyeong;Chung, In-Sik;Kwon, Byoung-Mog;Kim, Dae-Keun;Baek, Nam-In
    • Food Science and Biotechnology
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    • v.18 no.1
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    • pp.95-102
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    • 2009
  • The aerial parts of garland (Chrysanthemum coronarium L.) were extracted in 80% aqueous methanol (MeOH) and the concentrated extract was then partitioned using ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$, successively. EtOAc and n-BuOH fractions resulted in 4 glycerides with the application of octadecyl silica gel and silica gel column chromatography. The chemical structures of the glycerides were determined using several spectroscopic methods, including nuclear magnetic resonance (NMR) and mass spectrometry (MS) as (2S)-1-O-palmitoyl-sn-glycerol (1), (2S)-1-O-oleoyl-2-O-oleoyl- 3-O-$\beta$-D-galactopyranosyl-sn-glycerol (2), (2S)-1-O-palmitoyl-2-O-linoleoyl-3-O-phosphorouscholine-sn-glycerol (3), and (2S)-1-O-linolenoyl-2-O-palmitoyl-3-O-[$\alpha$-D-galactopyrasyl-($1{\rightarrow}6$)-$\beta$-D-galactopyranosyl]-sn-glycerol (4). The free fatty acids of these glycerides were determined with gas chromatography (GC)-MS analysis following alkaline hydrolysis and methylation. These glycerides demonstrated an inhibitory effect on acyl-CoA: cholesterol acyltransferase (ACAT, compound 1: $45.6{\pm}0.2%$ at $100{\mu}g/mL$), diacylglycerol acyltransferase (DGAT, compound 1: $59.1{\pm}0.1%$ at $25{\mu}g/mL$), farnesyl protein transferase (FPTase, compound 2: $98.0{\pm}0.1%$; compound 3: $55.2{\pm}0.1%$ at $100{\mu}g/mL$), and $\beta$-secretase ($IC_{50}$, compound 4: $2.6{\mu}g/mL$) activity. This paper is the first report on the isolation of these glycerides from garland and their inhibitory activity on ACAT, DGAT, FPTase, and $\beta$-secretase.

Inhibition of Low Density Lipoprotein-oxidation, ACAT-1, and ACAT-2 by Lignans from the Bark of Machilus thunbergii

  • Shrestha, Sabina;Park, Ji-Hae;Lee, Dae-Young;Cho, Jin-Gyeong;Lee, Do-Gyeong;Cho, Moon-Hee;Jeong, Tae-Sook;Kang, Hee-Cheol;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.54 no.1
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    • pp.63-66
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    • 2011
  • The bark of Machilus thunbergii was extracted with 80% aqueous methanol (MeOH), and the concentrated extract was partitioned using ethyl acetate (EtOAc), butanol (n-BuOH), and $H_2O$, successively. From the EtOAc fraction, five lignans were isolated through the repeated silica gel, octadecyl silica gel (ODS) and, Sephadex LH-20 column chromatography. Based on nuclear magnetic resonance (NMR), mass spectroscopy (MS), and infrared spectroscopy (IR) spectroscopic data, the chemical structures of the compounds were determined to be machilin A (1), machilin F (2), licarin A (3), nectandrin A (4), and nectandrin B, (5). This study presents comparative account of five lignans from M. thunbergii bark contributing inhibition of low density lipoprotein (LDL), ACAT-1, and ACAT-2. Compounds 2-5 showed varied degree of antioxidant activity on LDL with $IC_{50}$ values of 2.1, 11.8, 15.3, and $4.1{\mu}M$. Compounds 1, 2, and 3 showed inhibition activity on ACAT-1 with values $63.4{\pm}6.9%$ ($IC_{50}=66.8{\mu}M$), $53.7{\pm}0.9%$ ($IC_{50}=109.2{\mu}M$), and $78.7{\pm}0.2%$ ($IC_{50}=40.6{\mu}M$), respectively, at a concentration of 50 mg/mL, and on ACAT-2 with values $47.3{\pm}1.5%$ ($IC_{50}=149.7{\mu}M$), $39.2{\pm}0.2%$ ($IC_{50}=165.2{\mu}M$), and $52.1{\pm}1.0%$ ($IC_{50}=131.0{\mu}M$, respectively, at a concentration of 50 mg/mL.

Counter anion effects in anion exchange membrane-fabricated non-aqueous vanadium redox flow battery

  • Son, Pyeong Soo;Oh, Min-Seok;Ye, Jun-Hee;Choi, Seong-Ho
    • Analytical Science and Technology
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    • v.28 no.5
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    • pp.341-346
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    • 2015
  • In order to understand the counter anionic effects in a non-aqueous vanadium redox flow battery (VRFB), we synthesized four types of electrolyte salts (1-ethyltriethamine tertafluoroborate, [E-TEDA]+[BF4], 1-ethyltriethamine hexafluorophosphate, [E-TEDA]+[PF6], 1-butyltriethylamine tertafluoroborate, [B-TEDA]+[BF4], and 1-buthyltriethamine hexafluorophosphate [B-TEDA]+[PF6]) by counter anion exchange reaction after the SN2 reaction. We confirmed the successful synthesis of the electrolyte salts [E-TEDA]+[Br] and [B-TEDA]+[Br] via 1H-NMR spectroscopy and GC-mass analysis before the counter anion exchange reaction. The electric potential of the vanadium acetylacetonate, V(acac)3, as an energy storage chemical was shown to be 2.2 V in the acetonitrile solvent with each of the [E-TEDA]+[BF4], [E-TEDA]+[PF6], [B-TEDA]+[BF4], and [B-TEDA]+[PF6] electrolyte salts. In a non-aqueous VRFB with a commercial Neosepta AFN membrane, the maximum voltages reached 1.0 V and 1.5 V under a fixed current value of 0.1 mA in acetonitrile with the [E-TEDA]+[BF4] and [E-TEDA]+[PF6] electrolyte salts, respectively. The maximum voltage was 0.8 V and 1.1 V under a fixed current value of 0.1 mA in acetonitrile with the [B-TEDA]+[BF4] and [B-TEDA]+[PF6] electrolyte salts, respectively. From these results, we concluded that in the non-aqueous VRFB more of the [PF6] counter anion than the [BF4] counter anion was transported onto the commercial Neosepta AFN anion exchange membrane.

Molecular Cloning and Characterization of a Novel Exo-β-1,3-Galactanase from Penicillium oxalicum sp. 68

  • Zhou, Tong;Hu, Yanbo;Yan, Xuecui;Cui, Jing;Wang, Yibing;Luo, Feng;Yuan, Ye;Yu, Zhenxiang;Zhou, Yifa
    • Journal of Microbiology and Biotechnology
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    • v.32 no.8
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    • pp.1064-1071
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    • 2022
  • Arabinogalactans have diverse biological properties and can be used as pharmaceutical agents. Most arabinogalactans are composed of β-(1→3)-galactan, so it is particularly important to identify β-1,3-galactanases that can selectively degrade them. In this study, a novel exo-β-1,3-galactanase, named PoGal3, was screened from Penicillium oxalicum sp. 68, and hetero-expressed in P. pastoris GS115 as a soluble protein. PoGal3 belongs to glycoside hydrolase family 43 (GH43) and has a 1,356-bp gene length that encodes 451 amino acids residues. To study the enzymatic properties and substrate selectivity of PoGal3, β-1,3-galactan (AG-P-I) from larch wood arabinogalactan (LWAG) was prepared and characterized by HPLC and NMR. Using AG-P-I as substrate, purified PoGal3 exhibited an optimal pH of 5.0 and temperature of 40℃. We also discovered that Zn2+ had the strongest promoting effect on enzyme activity, increasing it by 28.6%. Substrate specificity suggests that PoGal3 functions as an exo-β-1,3-galactanase, with its greatest catalytic activity observed on AG-P-I. Hydrolytic products of AG-P-I are mainly composed of galactose and β-1,6-galactobiose. In addition, PoGal3 can catalyze hydrolysis of LWAG to produce galacto-oligomers. PoGal3 is the first enzyme identified as an exo-β-1,3-galactanase that can be used in building glycan blocks of crucial glycoconjugates to assess their biological functions.

Cytotoxic and Anti-inflammatory Activities of Lipids from the Nuruk (Rhizopus oryzae KSD-815) (누룩(Rhizopus oryzae KSD-815)으로부터 분리한 지질화합물의 세포독성 및 항염증 활성)

  • Kwak, Ho-Young;Lee, Sang-Jin;Lee, Dae-Young;Bae, Nark-Hyun;Jung, La-Koon;Hong, Sung-Youl;Kim, Gye-Won;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.51 no.2
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    • pp.142-147
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    • 2008
  • Nuruk is the Korean traditional Koji that contains various microorganisms and has been used to make the traditional fermented foods including alcoholic beverages. Rhizopus oryzae KSD-815 was isolated from the alcohol-fermenting Nuruk used for manufacturing traditional alcohol. In this study, the authors reported the isolation and identification of four lipids from the Nuruk (Rhizopus oryzae KSD-815) that inoculated wheat with Rhizopus oryzae KSD-815. The dried and powdered Nuruk (Rhizopus oryzae KSD-815) were extracted three times at room temperature with 80% aqueous MeOH. The extracts were partitioned with EtOAc, n-BuOH, and water, successively. The EtOAc extract was suspended in 80% MeOH and partitioned repeatedly with n-hexane. From the n-hexane fraction, four lipids were isolated through the repeated silica gel and ODS column chromatographies. According to the results of physico-chemical data including NMR, GC and MS, the chemical structures of the compounds were determined as linolenic acid methyl ester (1), palmitic acid methyl ester (2), linoleic acid (3), palmitic acid (4). Cytotoxicity was evaluated in huamn breast cancer cells, MDA-MB-231 and human hepatocarcinoma, SK-HEP-1 cells using MTT assay. Exposure of compounds 1 and 3 led to a dose-dependent inhibition of cell viability in both cancer cell lines. In addition, treatment of RAW264.7 cells with compound 3 caused inhibition of lipopolysaccharide/interferon-${\gamma}$-induced nitric oxide production.

Antioxidant Activity of Different Parts of Lespedeza bicolor and Isolation of Antioxidant Compound (싸리나무(Lespedeza bicolor) 부위별 추출물의 항산화 활성 및 항산화물질 분리)

  • Lee, Jae-Hak;Jhoo, Jin-Woo
    • Korean Journal of Food Science and Technology
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    • v.44 no.6
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    • pp.763-771
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    • 2012
  • In this study, total antioxidant properties of extracts from different parts of Lespedeza bicolor were determined using techniques of measuring 1,1-diphenyl-2-picryl hydrazyl/2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)-radical scavenging activity and total phenolic contents. The total antioxidant activities of leaf, stem and root extracts from various solvents (water, 50, 70, 100% ethanol, and hot-water) indicated that 50 and 70% ethanol extracts have high radical scavenging activities and phenolic contents. A systematic approach was used to determine the total antioxidant activity of different solvent fractions of the Lespedeza bicolor extracts, partitioning with chloroform, ethyl acetate, n-butanol, and water, and the ethyl acetate fraction was found to have the strongest antioxidant activity. Antioxidant assay-guided isolation was carried out to isolate potential antioxidant compounds. The ethyl acetate fraction of the leaf extract was subjected to silica gel, LH-20 and RP-18 column chromatography successively, and afforded compound 1, which was identified as eriodictyol by NMR and MS analysis, after which its antioxidant activity was determined.

Isolation and Identification of a Sterol and Three Glucosides from the Peel of Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) (추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 1종의 Sterol과 3종의 배당체 화합물의 단리 · 동정)

  • Lee, Yu Geon;Cho, Jeong-Yong;Lee, Hyun Joo;Lee, Yong Hyun;Lee, Sang-Hyun;Han, Tae-Ho;Kim, Wol-Soo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.45 no.5
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    • pp.557-564
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    • 2013
  • We isolated and identified antioxidants from acidic and neutral ethyl acetate fractions of the peel of pear (Pyrus pyrifolia N. cv. Chuhwangbae). We isolated 4 compounds from the methanol extract, by using 3 different types of column chromatography (Sephadex LH-20, silica gel, and octadecylsilane) and preparative HPLC. We identified the isolated compounds as (S)-(+)-2-cis-abscisic acid O-${\beta}$-D-glucopyranosyl ester (compound 1), 1-[4-O-${\beta}$-D-glucopyranosyl]phenyl ethanone (picroside, compound 2), ${\beta}$-sitosterol (compound 3), and ${\beta}$-sitosteryl 3-O-${\beta}$-D-glucopyranoside (compound 4) by nuclear magnetic resonance analysis. We are the first to report the identification of compounds 1, 2, and 4 from pear.