• Title/Summary/Keyword: NMR analysis

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Preparation and Characterization of Poly(Arylene Ether) Having Heterocyclic Quaternary Ammonium Functional Groups for Anion Exchange Membranes (음이온교환막용 헤테로고리형 4차 암모늄 작용기를 갖는 폴리(아릴렌 이써)의 제조 및 특성 분석)

  • LEE, SANG HYEOK;YOO, DONG JIN
    • Transactions of the Korean hydrogen and new energy society
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    • v.33 no.4
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    • pp.372-382
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    • 2022
  • In this study, anion exchange membranes were prepared by synthesizing the main chain into a poly(arylene ether) (PAE) structure, and the structures capable of improving the physical and chemical stability of the membrane by introducing a heterocyclic quaternary ammonium functional groups were studied. The chemical structure and thermal properties of the prepared polymer were confirmed by 1H-NMR, FT-IR, TGA, and DSC, and surface analysis was performed through AFM measurement. Additionally, dimensional stability and chemical properties was studied by measuring water uptake and swelling ratio, IEC and ionic conductivity. At 90℃, the quaternized poly(arylene ether) (QPAE)/1-methylpiperidine (MP) membrane exhibited the highest ionic conductivity of 27.2 mS cm-1, while the QPAE/1-methylimidazole (MI) membrane and QPAE/1-methylmorpholine (MM) membrane exhibited values of 14.5 mS cm-1 and 11.5 mS cm-1, respectively. In addition, the prepared anion exchange membrane exhibited high chemical stability in alkaline solution.

Multi-Function of a New Bioactive Secondary Metabolite Derived from Endophytic Fungus Colletotrichum acutatum of Angelica sinensis

  • Ramy S. Yehia
    • Journal of Microbiology and Biotechnology
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    • v.33 no.6
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    • pp.806-822
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    • 2023
  • In the current study we assessed a new crystallized compound, 5-(1-hydroxybutyl)-4-methoxy-3-methyl-2H-pyran-2-one (C-HMMP), from the endophytic fungus Colletotrichum acutatum residing in the medicinal plant Angelica sinensis for its in vitro antimicrobial, antibiofilm, antioxidant, antimalarial, and anti-proliferative properties. The promising compound was identified as C-HMMP through antimicrobial-guided fraction. The structure of C-HMMP was unambiguously confirmed by 2D NMR and HIRS spectroscopic analysis. Antimicrobial property testing of C-HMMP showed it to be effective against a variety of pathogenic bacteria and fungi with MICs ranging from 3.9 to 31.25 ㎍/ml. The compound displayed excellent antibiofilm activity against C. albicans, S. aureus, and K. pneumonia. Furthermore, the antimalarial and radical scavenging activities of C-HMMP were clearly dosedependent, with IC50 values of 0.15 and 131.2 ㎍/ml. The anti-proliferative activity of C-HMMP against the HepG-2, HeLa, and MCF-7 cell lines in vitro was investigated by MTT assay, revealing notable anti-proliferative activity with IC50 values of 114.1, 90, and 133.6 ㎍/ml, respectively. Moreover, CHMMP successfully targets topoisomerase I and demonstrated beneficial anti-mutagenicity in the Ames test against the reactive carcinogenic mutagen, 2-aminofluorene (2-AF). Finally, the compound inhibited the activity of α-glucosidase and α-amylase with IC50 values of 144.7 and 118.6 ㎍/ml, respectively. To the best of our knowledge, the identified compound C-HMMP was obtained for the first time from C. acutatum of A. sinensis, and this study demonstrated that C-HMMP has relevant biological significance and could provide better therapeutic targets against disease.

Alpha-Glucosidase Inhibitory Activity of Saponins Isolated from Vernonia gratiosa Hance

  • Pham Van Cong;Hoang Le Tuan Anh;Le Ba Vinh;Yoo Kyong Han;Nguyen Quang Trung;Bui Quang Minh;Ngo Viet Duc;Tran Minh Ngoc;Nguyen Thi Thu Hien;Hoang Duc Manh;Le Thi Lien;Ki Yong Lee
    • Journal of Microbiology and Biotechnology
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    • v.33 no.6
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    • pp.797-805
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    • 2023
  • Species belonging to the Vernonia (Asteraceae), the largest genus in the tribe Vernonieae (consisting of about 1,000 species), are widely used in food and medicine. These plants are rich sources of bioactive sesquiterpene lactones and steroid saponins, likely including many as yet undiscovered chemical components. A phytochemical investigation resulted in the separation of three new stigmastane-type steroidal saponins (1 - 3), designated as vernogratiosides A-C, from whole plants of V. gratiosa. Their structures were elucidated based on infrared spectroscopy (IR), one-dimensional (1D) and two-dimensional nuclear magnetic resonance (2D NMR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and electronic circular dichroism analyses (ECD), as well as chemical reactivity. Molecular docking analysis of representative saponins with α-glucosidase inhibitory activity was performed. Additionally, the intended substances were tested for their ability to inhibit α-glucosidase activity in a laboratory setting. The results suggested that stigmastane-type steroidal saponins from V. gratiosa are promising candidate antidiabetic agents.

Biological activity and analysis of α-glucosidase inhibitor from mulberry (Morus alba L.) wine (오디와인의 생리활성 및 α-glucosidase 저해제의 분석)

  • Son, Woo-Rim;Choi, Sang-Won
    • Food Science and Preservation
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    • v.20 no.6
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    • pp.877-885
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    • 2013
  • Wine extracts of four different berry fruits, such as mulberry, blueberry, strawberry, and raspberry, were investigated for antioxidant, anti-tyrosinase, and ${\alpha}$-glucosidase activities by using in vitro assays. Additionally, quantitative changes of ${\alpha}$-glucosidase inhibitor in mulberry wine were determined by HPLC according to mulberry cultivars and fermentation process. Among four berry wines examined, mulberry wine showed the most potent ${\alpha}$-glucosidase inhibitory activity with 69.37% at 0.23 mg/mL, while blueberry and strawberry wines exhibited the strongest inhibition against DPPH radical and tyrosinase activity, respectively. Four compounds were isolated and purified from mulberry wine by a series of isolation procedures, such as solvent fractionation, and Diaion HP-20, ODS-A, and Sephadex LH-20 column chromatographies. Among them, Comp. 4 exerted the strongest ${\alpha}$-glucosidase inhibitory activity ($I_C_{50}=31.57{\mu}M$), and its chemical structure was identified as quercetin by UV and NMR spectral analysis. Finally, the "Daeseongppong" (16.83 ppm) muberry wine had larger amount of quercetin than the "Iksuppong" (14.85 ppm) and "Cheongilppong" (8.92 ppm) mulberry wines, but their contents of three mulberry wines decreased considerably with aging process. These results suggest that mulberry wine containing quercetin acted as ${\alpha}$-glucosidase inhibitor may be useful as a potential functional wine for improving diabetic disorder.

Studies on the Determination Method of Monascus Pigments in Foods (식품 중 홍국색소의 분석법에 관한 연구)

  • Lee, Tal-Soo;Lee, Young-Ja;Kwon, Yong-Kwan;Park, Jae-Seok;Ko, Hyun-Sook;Sim, Kyu-Chang;Lee, Ju-Yeun;Shin, Jae-Wook;Song, Jee-Won;Lee, Chul-Won
    • Korean Journal of Food Science and Technology
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    • v.33 no.5
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    • pp.641-644
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    • 2001
  • This study was performed for development of new analytical method of monascus pigments in foods. In this method, analysis of monascus pigment in foods has been carried out by detection of monascin and ankaflavin of the main color component of monascus pigment as indicator compounds. Monascin and ankaflavin were isolated and identified by TLC, HPLC, Prep. HPLC, $^{1}H-NMR$ and Mass spectrophotometer. The analysis of monascin and ankaflavin in foods such as massal, sausage, mixed press ham, mixed fish sausage, semi-dried sausage and syrup was performed by using reverse phase high performance liquid chromatograph with Capcell Pak C18 column at wave length 390 nm. The quantitative results of monascin were as follows : $0.01{\sim}3.31\;{\mu}g/g$ item in massal, $0.05{\sim}0.10\;{\mu}g/g$ in mixed fish sausage, and $0.34{\sim}0.35\;{\mu}g/g$ in semi-dried sausage. But the quantitative results of ankaflavin were as follows: $0.02{\sim}0.89\;{\mu}g/g$ in massal, ankaflavin were not founded in other samples.

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The Properties of Flow and Compressive Strength of Mortar According In Replacement Ratio of Rapidly-Chilled Steel Slag Pine Aggregate (급냉 제강 슬래그 잔골재 대체율에 따른 모르타르의 유동성 및 압축강도 특성)

  • Cho Sung-Hyun;Kim Jin-Man;Kim Moon-Han;Han Ki-Suk
    • Journal of the Korea Concrete Institute
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    • v.17 no.1 s.85
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    • pp.77-84
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    • 2005
  • The steel slag, a by-product which is produced by refining pig iron during the manufacture of steel, is mainly used as road materials after aging. It is necessary to age steel slag for long time in air because the reaction with water and free-CaO in steel slag could make the expansion of volume. This problem prevents steel slag from being used as aggregate for concrete. However, steel slag used in this study was controled by a air-jet method which rapidly cools substance melted at a high temperature. The rapidly-chilled method would prevent from generation of free-CaO in steel slag. This study dealt with the influence of the using rate of rapidly-chilled steel slag on flow, dosage of SP, W/C ratio, and strength of mortar by statistical experimental design. Also, the results of this experiment were approved by statistical analysis methods, such as analysis of variance and F-testing. As results of F-testing, this paper proved at $1\%$ level of significance that the more the using rate of rapidly-chilled steel slag increased, the more this affected the enhancement of flow, the decrease of dosage of SP and W/C ratio, and the development of compressive strength. Also, considering the fluidity and compressive strength of mortar, it is desirable to use $75\%$ of rapidly-chilled steel slag for river sand.

Structural Analysis of Natural Indigo Colorants Extracted from Polygonum tinctorium (천연인디고 색소의 구조분석)

  • Chung, In-Mo;Lee, Kwang-Gill;Sung, Gyou-Byung;Kim, Hyun-Bok;Nam, Sung-Hee;Hong, In-Pyo
    • Journal of Sericultural and Entomological Science
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    • v.49 no.1
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    • pp.8-13
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    • 2007
  • Natural indigo colorants were prepared by extraction of Polygonum tinctorium which was harvested just in the blooming season(in the late of July). The components were analyzed by TLC and HPLC, and its structures were analyzed by FT-IR, EI-mass. The results obtained are summarized as follows; The natural indigo powder was dissolved in DMSO and developed in eluent, $CHCI_3/CH_3CN$(8.5:1.5 v/v) by means of TLC for its quality analysis. It was segregated into indirubin as a red colour and indigo as a blue colour. In case of HPLC analysis,. FT-IR spectrum of indirubin showed a peak for NH residue between 3200 and $3300cm^{-1}$. $^1H-NMR$ spectrum for indigo displayed AA'BB' spin system caused by indole structure between 6.5 and 7.7ppm of H4, 5, 6 and 7, and -NH proton for indirubin showed an singlet between 10.88 and 11.0ppm. EI-mass spectrum of indigo and indirubin both disclosed their molecular size as 262 and it implies that these two substances are isomer.

Characteristics and functional analysis of Bacillus strains from the fermented soybean products, Cheonggukjang (전통 발효 청국장으로부터 분리한 Bacillus 균주들의 특성 및 기능 분석)

  • Moon, Ji-Young;Kwon, Soon-Wo;Hong, Seung-Beom;Seok, Soon-Ja;Kim, Jeong-Seon;Kim, Soo-Jin
    • Korean Journal of Microbiology
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    • v.51 no.3
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    • pp.300-307
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    • 2015
  • For selecting Bacillus strains producing high-quality Cheonggukjang, 8 strains were isolated from the different Cheonggukjang samples. Seven of them exhibited the highest 16S rRNA gene sequence similarity value of over 99.9% to Bacillus subtilis subsp. subtilis and one of them showed the similarity to B. licheniformis. All the strains showed positive activities for amylase, cellulase, protease and lipase, and 6 strains are positive for fibrinolytic activity. To confirm the safety of the strains isolated from the samples of Cheonggukjang which are manufactured by traditional method, strains were analyzed for the presence of seven toxin genes of Bacillus cereus and results were found negative. And 7 strains did not produce at all or merely produce both histamine and tyramine, the representative biogenic amines. Biogenic amine degradation analysis by HPLC revealed that, most of them exhibited tyramine degradation activity. For Cheonggukjang fermented by artificial inoculation of selected strains, fermentation property, sensory test, volatile basic nitrogen production and metabolic profiles by $^1H-NMR$ were tested. Seven strains were confirmed to make high-quality Cheonggukjang.

Studies on the Michael Addition Reaction between Secondary Amino Groups on the Silica Surface with Poly(ethylene glycol) Diacrylates (실리카 나노입자 표면에 결합된 2차 아미노기와 Poly(ethylene glycol) Diacrylate의 마이클 부가반응에 대한 연구)

  • Jeon, Ha Na;Ha, KiRyong
    • Polymer(Korea)
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    • v.36 no.6
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    • pp.822-830
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    • 2012
  • We used dipodal type bis[3-(trimethoxysilyl)propyl]amine (BTMA) silane coupling agent to modify silica nanoparticles to introduce secondary amino groups on the silica surface. These N-H groups were reacted with three different molecular weights (M.W. = 258, 575, and 700) of poly(ethylene glycol) diacrylates to introduce different attached layer thicknesses on the silica surface by Michael addition reaction. After Michael addition reaction, we used several analytical techniques such as fourier transform infrared spectroscopy (FTIR), elemental analysis (EA) and solid state $^{13}C$ cross-polarization magic angle spinning (CP/MAS) nuclear magnetic resonance spectroscopy to characterize introduced structures. We found almost complete Michael addition reaction of both two acrylate groups of PDGDA with N-H groups of BTMA modified silica to form ${\beta}$-amino acid esters. Between equimolar ratio of pure BTMA and pure PEGDA reaction, only one acrylate group of two acrylate groups of PEGDA reacted with N-H groups of pure BTMA to form ${\beta}$-amino acid ester and the other remaining acrylate group can be used to form a polymer later.

Ethylenediamine Complex for Stabilization of Omeprazole (오메프라졸의 안정화를 위한 에칠렌디아민 복합체 개발)

  • Oh, Sea-Jong;Kim, Eun-Young;Kim, Kil-Soo;Kim, Yuon-Jeung;Lee, Gye-Ju
    • Journal of Pharmaceutical Investigation
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    • v.25 no.1
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    • pp.9-17
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    • 1995
  • To stabilize omeprazole(OMP), ethylenediamine(ED) complex of omeprazole(OMPED) was prepared by reaction between OMP and ED in methanol, and the complex formation was confirmed by the instrumental analysis, i.e., IR, DSC, EA, NMR, MS and XRD. The rates of decomposition of OMP and OMPED in aqueous solution and the shelf lives at standard temperature were measured by accelerated stability analysis. The results are summarized as follows; The mole ratio of OMP and ED in OMPED complex is 1:1, the energy of formation within OMPED might be combined between polar imidazole group of OMP with induced a dipole amine group in the readily polarizable ED molecule. At standard temperature the degradation rate constant of OMP in aqueous solution is $2.540{\times}10^{-2}\;hr^{-1}$ and the shelf life is 4.15 hrs, and in the case of OMPED the degradation rate constant is $7.986{\times}10^{-4}\;hr^{-1}$ and the shelf life is 131.96 hrs. So, the OMPED has about 31 times longer shelf life than OMP. The activation energy of OMP and OMPED are 5.23 and 18.55 kcal $mole^{-1}$ respectively. The stability of OMP is dependent chiefly on pH in the solutions and it decomposes readily in acidic medium by hydrogen ion catalized reaction but becomes stable beyond pH 9.0. In case of the ED-complex, OMPED is stable in neutral as well as in dilute acidic solutions even in pH 6, OMPED is very stable to light(UV), that is, the rate constant and shelf life of OMP are $k=1.0188{\times}10^{-2}\;day^{-1}$, $T_{90%}=4.5 \;days$, on the other hand, the those of OMPED are $k=7.138{\times}10^{-4}\;day^{-1}$, $T_{90%}=64.1\;days$, respectively. From the above results, it is thought that new dosage forms could be developed by using the OMPED as a potential OMP complex.

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