• Title/Summary/Keyword: 1D $^1H-NMR$

Search Result 639, Processing Time 0.032 seconds

Isolation and Identification of Flavonoids from the Roots of Brassica rapa ssp. (순무(Brassica rapa ssp.) 뿌리로부터 flavonoid의 분리 및 동정)

  • Jeong, Rak-Hun;Wu, Qian;Cho, Jin-Gyeong;Lee, Dae-Young;Shrestha, Sabina;Lee, Min-Ho;Lee, Kyung-Tae;Choi, Myung-Sook;Jeong, Tae-Sook;Ahn, Eun-Mi;Chung, Hae-Gon;Rho, Yeong-Deok;Baek, Nam-In
    • Journal of Applied Biological Chemistry
    • /
    • v.56 no.1
    • /
    • pp.23-27
    • /
    • 2013
  • The roots of Brassica rapa ssp. were extracted with 95% aqueous ethanol and the concentrated extracts were partitioned using ethyl acetate (EtOAc), n-butyl alcohol and $H_2O$, successively. From the EtOAc fraction, five flavonoids were isolated through repeated silica gel and octadecyl silica gel (ODS) column chromatography (c.c.). Based on NMR, mass spectrometry (MS) and IR spectroscopic data, the chemical structures of the compounds were determined to be licochalcone A (1), 4,4'-dihydroxy-3'-methoxychalcone (2), liquirtigenin (3), liquiritin (4), and isoliquiritin (5). This is the first report of these compounds isolated from the root of this plant.

Synthesis and Properties of Polybenzoxazole Precursors having Oligo(oxy ethylene) pendant (Oligo(oxy ethylene) pendant를 갖는 PBO 전구체의 합성 및 특성)

  • Lee, Eung-Jae;Yoon, Doo-Soo;Bang, Moon-Soo;Choi, Jae-Kon
    • Journal of the Korea Academia-Industrial cooperation Society
    • /
    • v.14 no.5
    • /
    • pp.2550-2558
    • /
    • 2013
  • Poly(o-hydroxyamides)(PHAs) copolymers having oligo(oxy ethylene) pendant in the main chain were synthesized by solution polycondensation reaction at low temperature. Copolymer precursors were studied by fourier transform infrared(FT-IR), differential scanning calorimeter(DSC), thermogravimetric analyzer(TGA), universal testing machine(UTM) and limited oxygen index(LOI). The inherent viscosities of the PHAs measured at $35^{\circ}C$ in DMAc or DMAc/LiCl solution were in the range of 0.74~1.42 dL/g. Solubility of the precursors with higher oligo(oxy ethylene) unit was increased, but the PBOs were nearly insoluble in a variety of solvents. The degradation temperature of the copolymer precursors was recorded in the ranges of $408{\sim}664^{\circ}C$ in nitrogen and char yields showed 13~59% values at $900^{\circ}C$. The mechanical properties and flame retardancy of copolymer precursors decreased with higher oligo(oxy ethylene) unit.

Enzymatic Synthesis of Puerarin Glucosides Using Leuconostoc Dextransucrase

  • Ko, Jin-A;Ryu, Young Bae;Park, Tae-Soon;Jeong, Hyung Jae;Kim, Jang-Hoon;Park, Su-Jin;Kim, Joong-Su;Kim, Doman;Kim, Young-Min;Lee, Woo Song
    • Journal of Microbiology and Biotechnology
    • /
    • v.22 no.9
    • /
    • pp.1224-1229
    • /
    • 2012
  • Puerarin (P), an isoflavone derived from kudzu roots, has strong biological activities, but its bioavailability is often limited by its low water solubility. To increase its solubility, P was glucosylated by three dextransucrases from Leuconostoc or Streptococcus species. Leuconostoc lactis EG001 dextransucrase exhibited the highest productivity of puerarin glucosides (P-Gs) among the three tested enzymes, and it primarily produced two P-Gs with a 53% yield. Their structures were identified as ${\alpha}$-$_D$-glucosyl-($1{\rightarrow}6$)-P (P-G) by using LC-MS or $^1H$- or $^{13}C$-NMR spectroscopies and ${\alpha}$-$_D$-isomaltosyl-($1{\rightarrow}6$)-P (P-IG2) by using specific enzymatic hydrolysis, and their solubilities were 15- and 202-fold higher than that of P, respectively. P-G and P-IG2 are easily applicable in the food and pharmaceutical industries as alternative functional materials.

Successive Synthesis of Well-Defined Star-Branched Polymers by an Iterative Approach Based on Living Anionic Polymerization

  • Higashihara Tomoya;Inoue Kyoichi;Nagura Masato;Hirao Akira
    • Macromolecular Research
    • /
    • v.14 no.3
    • /
    • pp.287-299
    • /
    • 2006
  • To successively synthesize star-branched polymers, we developed a new iterative methodology which involves only two sets of the reactions in each iterative process: (a) an addition reaction of DPE or DPE-functionalized polymer to a living anionic polymer, and (b) an in-situ reaction of 1-(4-(4-bromobutyl)phenyl)-1-phenylethylene with the generated 1,1-diphenylalkyl anion to introduce one DPE functionality. With this methodology, 3-, 4-, and 5-arm, regular star-branched polystyrenes, as well as 3-arm ABC, 4-arm ABCD, and a new 5-arm ABCDE, asymmetric star-branched polymers, were successively synthesized. The A, B, C, D, and E arm segments were poly(4-trimethylsilylstyrene), poly(4-methoxystyrene), poly(4-methylstyrene), polystyrene, and poly(4-tert-butyldimethylsilyloxystyrene), respectively. All of the resulting star-branched polymers were well-defined in architecture and precisely controlled in chain length, as confirmed by SEC, $^1H$ NMR, VPO, and SLS analyses. Furthermore, we extended the iterative methodology by the use of a new functionalized DPE derivative, 1-(3-chloromethylphenyl)-1-((3-(1-phonyletheny1)phenyl) ethylene, capable of introducing two DPE functionalities via one DPE anion reaction site in the reaction (b). The number of arm segments of the star-branched polymer synthesized by the methodology could be dramatically increased to 2, 6, and up to 14 by repeating the iterative process.

Development of Gradient Centrifugal Partition Chromatography Method and Its Application for the Isolation of 3,5-Dimethoxyphenanthrene-2,7-diol and Batatasin-I from Dioscorea opposita

  • Yoon, Kee-Dong;Yang, Min-Hye;Chin, Young-Won;Kim, Yoen-Jun;Kim, Hye-Ryung;Choi, Ki-Ri;Park, Ju-Hyun;Kim, Jin-Woong
    • Natural Product Sciences
    • /
    • v.15 no.3
    • /
    • pp.144-150
    • /
    • 2009
  • Gradient centrifugal partition chromatography (GCPC) method was developed and applied to isolate 3,5-dimethoxyphenanthrene-2,7-diol (DMP) and batatasin-I (BA-I) from the dichloromethane soluble extract of Dioscorea opposita. In this method, the lower phase of n-hexane-methanol-water system (HMW, 10 : 9 : 1, v/v) was used as a mobile phase A (MpA) and water was used as a mobile phase B (MpB). This gradient CPC method is comparable to that of reversed-phase HPLC method in that the stationary upper-phase of HMW (10 : 9 : 1 v/v) works as if it were reversed-phase silica gel due to its hydrophobic property, while the lower phase (MpA) and water (MpB) functioned as hydrophilic mobile phases. The initial condition of the mobile phase was 20% MpA/80% MpB and maintained for 150 min to obtain DMP (1.2 mg), and then MpA was increased up to 50% to elute BA-I (1.7 mg). The purities of DMP and BA-I were 94.1% and 98.3% with the recovery yields of 83% and 86%, respectively. Similar results were obtained by linear-gradient CPC. The CPC peak fractions were identified by comparing their retention time to those of authentic samples of DMP and BA-I and their spectroscopic data ($^1$H NMR and $^{13}$C NMR) to those of literature values.

Analysis of metabolites in wheat roots in response to salinity stress

  • Kim, Da-Eun;Roy, Swapan Kumar;Kim, Ki-Hyun;Cho, Seong-Woo;Park, Chul-Soo;Lee, Moon-Soon;Woo, Sun-Hee
    • Proceedings of the Korean Society of Crop Science Conference
    • /
    • 2017.06a
    • /
    • pp.200-200
    • /
    • 2017
  • Salinity stress is one of the most important abiotic stresses and severely impairs plant growth and production. Root is the first site for nutrient accumulation like as $Na^+$ in the plant. To investigate the response of wheat root under salinity stress, we executed the characterization of morphology and analysis of metabolites. Wheat seeds cv. Keumgang (Korean cultivar) were grown on the moist filter paper in Petri dish. After 5 days, seedlings were transferred to hydroponic apparatus at 1500 LUX light intensity, at $20^{\circ}C$ with 70% relative humidity in a growth chamber. Seedlings (5-day-old) were exposed to 50mM, 75mM, 100mM NaCl for 5 days. Ten-day-old seedlings were used for morphological characterization and metabolite analysis. Root and leaf length became shorter in high NaCl concentration compared to following NaCl treatment. For confirmation of salt accumulation, wheat roots were stained with $CoroNa^+$ Green AM, and fluoresce, and the image was taken by confocal microscopy. $Na^+$ ion accumulation rate was higher at 100mM compared to the untreated sample. Furthermore, to analyze metabolites in the wheat root, samples were extracted by $D_2O$ solvent, and extracted sample was analyzed by 1H NMR spectroscopy. Fourteen metabolites were identified in wheat roots using NMR spectroscopy. Methanol and ethanol were up-regulated, whereas formate, aspartate, aminobutyrate, acetate and valine were down-regulated under salinity stress on roots of wheat. Fumarate had no change, while glucose, betaine, choline, glutamate and lactate were unevenly affected during salinity stress.

  • PDF

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
    • /
    • v.18 no.1
    • /
    • pp.95-102
    • /
    • 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.

Neurochemical Profile Quantification of Regional Adult Mice Brain Using: ex vivo $^1H$ High-Resolution Magic Angle Spinning NMR Spectroscopy (생체 외 조직 고 분해능 Magic Angle Spinning을 이용한 정상 Adult Mice에서의 뇌 부위별 뇌 신경화학 대사물질 정량분석)

  • Lee, Do-Wan;Woo, Dong-Cheol;Lee, Sung-Ho;Kim, Sang-Young;Kim, Goo-Young;Rhim, Hyang-Shuk;Choi, Chi-Bong;Kim, Hwi-Yool;Lee, Chang-Wook;Choe, Bo-Young
    • Progress in Medical Physics
    • /
    • v.21 no.1
    • /
    • pp.35-41
    • /
    • 2010
  • The purpose of this study is to quantitate regional neurochemical profile of regional normal adult mice brain and assess regional metabolic differences by using ex vivo $^1H$ high-resolution magic angle spinning nuclear magnetic resonance spectroscopy ($^1H$ HR-MAS NMRS). The animals were matched in sex and age. The collected brain tissue included frontal cortex, temporal cortex, thalamus, and hippocampus. Quantitative 1D spectra were acquired on 40 samples with the CPMG pulse sequence (8 kHz spectral window, TR/TE = 5500/2.2 ms, NEX = 128, scan time: 17 min 20 sec). The mass of brain tissue and $D_2O$+TSP solvent were 8~14 mg and 7~13 mg. A total of 16 metabolites were quantified as follow: Acet, NAA, NAAG, tCr, Cr, tCho, Cho, GPC + PC, mIns, Lac, GABA, Glu, Gln, Tau and Ala. As a results, Acet, Cho, NAA, NAAG and mIns were showed significantly different aspects on frontal cortex, hippocampus, temporal cortex and thalamus respectively. The present study demonstrated that absolute metabolite concentrations were significantly different among four brain regions of adult mice. Our finding might be helpful to investigate brain metabolism of neuro-disease in animal model.

Aburatubolactam C, a Novel Apoptosis-inducing Substance Produced by Marine Streptomyces sp. SCRC A-20

  • Bae, Myung-Ae;Yamada, Kaoru;Uemura, Daisuke;Seu, Jung-Hwan;Kim, Young-Ho
    • Journal of Microbiology and Biotechnology
    • /
    • v.8 no.5
    • /
    • pp.455-460
    • /
    • 1998
  • In the course of screening for new antitumor substances, a novel cytotoxic agent inducing apoptotic cell death was isolated from the culture broth of marine bacterial strain SCRC A-20. Strain SCRC A-20 was separated from a mollusk and was chemotaxonomically identified as a Streptomyces sp. The cytotoxic substance was purified by organic solvent extraction followed by silica gel column chromatography and preparative TLC. HRFAB-MS determined its molecular formula to be $C_{30}H_{40}N_2O_5$ (MW 508). The 1D and 2D NMR spectral data demonstrated that the substance has a novel lactam structure of a 20-membered macrocycle coupled with a unique acyl tetramine and bicyclo[3.3.0] octane, which includes three methyl groups, six olefinic protons, five carbonyl groups, a conjugated diene and a dienone. The substance, named aburatubolactam C, appeared to be cytotoxic for various continuously proliferating tumor cells of human and murine origins. The $IC_{50}$ values determined by MIT assay were in the range of 0.3 to $5.8\mug/ml$. When Jurkat T cells were treated with $3\mug/ml$. of aburatubolactam C, the apoptotic DNA fragmentation was detectable within 3 h, indicating that the cytotoxic effect of aburatubolactam C on tumor cells is attributable to the induced apoptosis.

  • PDF

Synthesis and characterization of PPG-based urethane-modified epoxy resin for enhancing impact resistance of epoxy composite resin (에폭시 복합수지의 내충격성을 향상을 위한 PPG 기반 우레탄 변성 에폭시 합성 및 특성 분석)

  • Hwang, Chiwon;Jeon, Jaehee;Ahn, Dowon;Yu, Youngchang;Lee, Wonjoo
    • Journal of Adhesion and Interface
    • /
    • v.23 no.2
    • /
    • pp.44-52
    • /
    • 2022
  • Epoxy resin has the disadvantage of being easily destroyed by instantaneous impact due to its high crosslinking density despite its high glass transition temperature (Tg) and excellent properties. To compensate for this, in this study, polyol was synthesized by ring opening polymerization of propylene glycol (PPG) diamine, Jeffamine D 2000 and propylene carbonate, and urethane modified epoxy was synthesized using this. The properties of the synthesized urethane modified epoxy were confirmed by FT-IR, H-NMR. To confirm the degree of improvement in impact resistance as an adhesive, a urethane modified epoxy adhesive was prepared by mixing a digylcidyl ether bisphenol A (DGEBA) with curing agent and curing accelerator. Properties test of urethane modified epoxy were shear strength, tensile strength and impact strength. As a result, excellent results were obtained in all test when the ratio of DGEBA : urethane modified epoxy was 8:2.