• Title/Summary/Keyword: 1D $^1H-NMR$

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Structure Determination of Sucrose by Acetylation and Acid Hydrolysis

  • Min, Hee-Jeong;Lee, Tae-Seong;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.42 no.2
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    • pp.183-192
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    • 2014
  • For the structure determination of D-(+)-sucrose, which consists of ${\alpha}$-D-(+)-glucose and ${\beta}$-D-(+)-fructose, it was acetylated with acetic anhydride and triethyl amine, pyridine, zinc chloride, and sodium acetate as catalysts. The acetylated D-(+)-sucrose was acid-hydrolyzed using sulfuric acid and sodium chloride in methanolic solution. The structures of the reaction products were determined by $^1H$-NMR and $^{13}C$-NMR spectra. The yield of the acetylation indicated the high value in zinc chloride as 70% in zinc chloride catalyst. The acid-hydrolyzed product of the acetylated D-(+)-sucrose, 2,3,4,6,1',3',4',6'-octa-O-acetyl-D-(+)-sucrose, gave 2,3,4,6-tetra-O-acetyl-${\beta}$-D-(+)-glucose and it suggests that the acetylated D-(+)-sucrose was rearranged through the formation of oxonium ion by mutarotation in the 2,3,4,6-tetra-O-acetyl-${\alpha}$-D-(+)-glucose moiety and through the ring opening in the 1',3',4',6'-tetra-O-acetyl-${\beta}$-D-(+)-fructose moiety.

Synthesis of Novel Kojic Acid Derivative and Its Anti-pigmentation Effect (코직산 유도체의 합성과 미백효과)

  • Kim Ki Ho;Kim Ki Soo;Kim Jin Guk;Han Chang Sung;Kim Young Heui;Park Soo Nam
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.3 s.47
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    • pp.409-414
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    • 2004
  • Kojic acid is well known for its anti-pigmentation effect with tyrosinase inhibition activity. However, kojic acid is a unstable compound. In order to improve stability, kojic acid derivative, kojic acid $6-O-2',3',4',6'-tetraacetyl-{\beta}-D-glucopy-ranoside\;(KTGP)$, was synthesized with $O-pentaacetyl-{\beta}-D-glucose$ through the regio- and stereo-selective glycosylation of 6-OH group of kojic acid. High yield $(80\%)$ was obtained by the use of Lewis acid and organic base in nonpolar solvent. Hydrolysis of KTGP with the aid of sodium methoxide in methanol afforded kojic acid $6-O-{\beta}-D-glucopyranoside$ (KGP), which was confirmed by $^1H-NMR\;and\;^{13}C-NMR$ KGP is freely soluble in water and soluble in methanol and ethanol. Inhibition activity of KGP for tyrosinase was investigated by measuring the activity of mushroom tyrosinase compared with those of ascorbic acid, kojic acid, and arbutin. The free radical-scavenger activity was determined by the 1,1-diphenyl- 2-picrylhydrazyl (DPPH) assay. In toxicity assay, KGP was much less toxic than kojic acid and arbutin, Therefore, glycosylation of kojic acid may be useful for the development of stable kojic acid derivatives.

A New Sphingosine from a Marine Sponge Haliclona (Reniera) sp.

  • Mansoor, Tayyab A.;Park, Tae-Seong;Luo, Xuan;Hong, Jong-Ki;Lee, Chong-O.;Jung, Jee-H.
    • Natural Product Sciences
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    • v.13 no.3
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    • pp.247-250
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    • 2007
  • A new sphingosine (1) was isolated from the MeOH extract of a marine sponge Haliclona (Reniera) sp. by bioactivity-guided fractionation. The 1D and 2D NMR, and MS spectroscopic analyses were used to establish the planar structure of 1. The stereochemistry of the compound was defined on the basis of modified Mosher's method, comparison of optical rotation and NMR data with those of the reported. Compound 1 was mildly cytotoxic to a panel of five human solid tumor cell lines.

Gallotannins from Nut Shell Extractives of Camellia oleifera

  • HE, Yi-Chang;WU, Mei-Jie;LEI, Xiao-Lin;YANG, Jie-Fang;GAO, Wei;BAE, Young-Soo;KIM, Tae-Hee;CHOI, Sun-Eun;LI, Bao-Tong
    • Journal of the Korean Wood Science and Technology
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    • v.49 no.3
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    • pp.267-273
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    • 2021
  • Camellia nut shell was collected, dried at room temperature and ground to get fine powder. The powder was extracted three times with 95% EtOH, combined, evaporated, and then freeze dried. The crude powder was dissolved in H2O and then sequentially fractionated with n-hexane, CH2Cl2, EtOAc and n-BuOH. A part of EtOAc fraction was chromatographed on a silica gel and on a Sephadex LH-20 columns using MeOH, aqueous MeOH, EtOAc-n-hexane and EtOH-n-hexane to isolate gallotannins. Three gallotannins, 1,2-di-O-galloyl-β-D-glucopyranoside (2), 1,2,6-tri-O-galloyl-β-D-glucopyranoside (3) and 1,2,3,6-tetra-O-galloyl-β-D-glucopyranoside (4), including gallic acid (1), were isolated and elucidated by NMR and Mass spectroscopies. Although nothing new, these gallotannins were first reported from the nut shell extractives of camellia tree (Camellia oleifera C. Abel). This study was to investigate the chemical constituents, especially hydrolysable tannins, of nut shell extractives of Camellia oleifera and to provide basic information for the future chemical utilization of this species.

Hepatoprotective constituents from Beta vulgaris var. cycla

  • Kim, In-Kyum;Chin, Young-Won;Song, Won-Lim;Yang, Hye-Kyung;Kim, Young-Choong;Kim, Jin-Woong
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.259.1-259.1
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    • 2003
  • In the course of hepatoprotective screening for domestic plants. the aerial parts of B. vulgaris var. cycla exhibited hepatoprotective activity which was determined by using the primary cultures of rat hepatocytes injured by H2O2. Bioactivity-guided separation for this plant gave a new flavonoid (1) and the known compounds (2-4), which structures were elucidated by 1H-NMR, HMQC, 1H-1H COSY and HMBC as compound 1, apigenin 8-C-, 7-O-di-$\beta$-D-glucopyranoside, compound 2, vitexin 2"-O-$\beta$-D-glucopyranoside, compound 3, (+)-dehydrovomifoliol, and compound 4, 3-hydroxy-5$\alpha$, 6$\alpha$-epoxy-$\beta$-ionone.

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Nuclear Magnetic Relaxation in Flurinated $YBa_2Cu_3O_{7-x}$

  • Lee, Cheol-Eui;White, D.;Davies, P.K.;Moon, B.M.;Sung, M.Y.;Park, J.H.;Kim, B.H.
    • Journal of Magnetics
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    • v.1 no.1
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    • pp.1-3
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    • 1996
  • The $YBa_2Cu_3O_{7-x}$ structure has been fluorinated by a gas phase exchange technique. The ${^19}F$NMR (nuclear magnetic resonance) spin-lattice relaxation rate (1/T1) measurements on a fluorinated sample gave superconducting energy gap of $2\Delta=4.6kT_c$.

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Isolation of a Potent Mosquito Repellent from Vitex negundo L.: An Alternative Source of Rotundial

  • Amancharla, Praveen K.;Muthuraj, Patrick S.;Rao, Gottumukkala V.;Singh, Om V.
    • Natural Product Sciences
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    • v.5 no.2
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    • pp.104-106
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    • 1999
  • The chloroform fraction of the aqueous extract of the fresh leaves of Vitex negundo by bioactivity guided isolation yielded a pure compound, rotundial (1) which has shown potent mosquito repellent activity. Using spectral data (UV, IR, $^1H\;&\;^{13}C$ NMR and MS) its structure has been elucidated.

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NMR study of the interaction of T$_4$ Endonuclease V with DNA

  • 이봉진;유준석;임형미;임후강
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1994.04a
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    • pp.267-267
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    • 1994
  • In order to obtain insight into the mechanism by which DNA containing a thymine photo-dimer is recognized by the excision repair enzyme, T$_4$ endonuclease V, we have taken NMR study of this protein and its complex with oligonucleotides. The conformations of five different DNA duplexes DNA I : d(GCGGATGGCG).d(CGCCTACCGC), DNA II d(GCGGTTGGCG) .d(CGCCAACCGC), DNA III : d(GCGGT ^ TGGCG) .d(CGCCAACCGC), DNA IV d(GCGGGCGGCG).d(CGCCCGCCGC) and DNA V d(GCGGCCGGCG) . d(CGCCGGCCGC) were studied by $^1$H NMR. The NMR spectra of these five DNA duplexes in the absence of the enzyme clearly show that the formation of a thymine dimer within the DNA induces only a minor distortion in the structure, and that the overall structure of B type DNA is retained. The photo-dimer formation is found to cause a large change in chemical shifts at the GC7 base pair, which is located at the 3'-side of the thymine dimer, accompanied by the major conformational change at the thymine dimer site. The binding of a mutant T$_4$ endonuclease V (E23Q), which is unable to digest DNA containing a thymine dimer, to the DNA duplex d(GCGGT ^ TGGCG)ㆍd(CGCCAACCGC) causes a large down-field shift in the imino proton resonance of GC7. Therefore, this position is thought to be either the crucial point of the interaction wi th T$_4$ endonuclease V, or the si to of a conformational change in the DNA caused by the binding of T$_4$ endonuclease V. Usually, it is very difficult to assign NMR peaks in DNA * protein complex because of severe peak overlaps. In order to overcome these peak overlaps, we used a method of deuterium incorporation.

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Synthesis and Properties of Semi-Flexible Aromatic Polyesters Containing Pentamethylene Group in Main Chain (주사슬에 펜타메틸렌기를 가지고 있는 반 유연성 방향족 폴리에스터의 합성 및 성질)

  • Bang, Moon-Soo;Yoon, Doo-Soo;Choi, Jae-Kon
    • Elastomers and Composites
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    • v.44 no.4
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    • pp.436-441
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    • 2009
  • Semi flexible polyesters containing aromatic rings and pentamethylene groups in the main chain were synthesized by direct polycondensation reaction. The structures of these polymers were investigated by $^1H$-NMR and FT-IR and the phase transition behavior was characterized with DSC, TGA and crossed polarizing microscope. Inherent viscosities ($\eta_{inh}$) of polymers measured in phenol/p-chlorophenol/1,1,2,2-tetrachloroethane were between 0.46 and 1.30 dL/g. As increasing the linearlity of rigid moieties in polyster, melting transition temperatures ($T_m$) increased and solubilities in organic solvents decreased. P-H, P-mH and P-4H of the polymers formed turbid melts that showed stir-opalescence and nematic phase at the broad anisotropic region, However, P-R, P-C and P-2B did not exhibit any textures related to the liquid crystallinity.

A New Stilbene Dimer and Other Chemical Constituents from Monanthotaxis littoralis with Their Antimicrobial Activities

  • Dongmo, Arnaud Joseph Nguetse;Ekom, Steve Endeguele;Tamokou, Jean-de-Dieu;Tagousop, Cyrille Ngoufack;Harakat, Dominique;Voutquenne-Nazabadioko, Laurence;Ngnokam, David
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.317-325
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    • 2020
  • A new dimer stilbene [Monalittorin (1)] and ten known compounds [engeletin (2), aurantiamide acetate (3), lupeol (4), friedelin (5), quercetin (6), tiliroside (7), rutoside (8), astragalin (9), isoquercitrin (10) and quercimeritroside (11)] have been isolated from the leaves of Monanthotaxis littoralis (Annonaceae). The structures of these compounds were established by interpretation of their data, mainly, HR-TOFESIMS, 1-D NMR (1H and 13C) and 2-D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and by comparison with the literature. The evaluation of their antimicrobial activities against three bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli S2 (1) and Pseudomonas aeruginosa PA01) and three fungal strains (Candida albicans ATCC10231, Candida tropicalis PK233 and Cryptococcus neoformans H99) using broth micro dilution method, showed the largest antimicrobial activities of EtOAc fraction and compounds 1, 5, 6, 8 and 11 (MIC = 8 - 64 ㎍/mL). In addition, EtOAc fraction presented synergistic effect with Vancomycin and fluconazole against the tested microorganisms.