• Title/Summary/Keyword: NMR study

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Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

  • Demmak, Rym Gouta;Bordage, Simon;Bensegueni, Abederrahmane;Boutaghane, Naima;Hennebelle, Thierry;Mokrani, El Hassen;Sahpaz, Sevser
    • Natural Product Sciences
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    • v.25 no.2
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    • pp.115-121
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    • 2019
  • Alzheimer's disease is a chronic neurodegenerative disorder with no curative treatment. The commercially available drugs, which target acetylcholinesterase, are not satisfactory. The aim of this study was to investigate the cholinesterase inhibitory activity of Solenostemma argel aerial part. Eight compounds were isolated and identified by NMR: kaempferol-3-O-glucopyranoside (1), kaempferol (2), kaempferol-3-glucopyranosyl($1{\rightarrow}6$)rhamnopyranose (3) p-hydroxybenzoic acid (4), dehydrovomifoliol (5), 14,15-dihydroxypregn-4-ene-3,20-dione (6), 14,15-dihydroxy-pregn-4-ene-3,20-dione-$15{\beta}$-D-glucopyranoside (7) and solargin I (8). Two of them (compounds 2 and 3) could inhibit over 50 % of butyrylcholinesterase activity at $100{\mu}M$. Compound (2) displayed the highest inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with a slight selectivity towards the latter. Molecular docking studies supported the in vitro results and revealed that (2) had made several hydrogen and ${\pi}-{\pi}$ stacking interactions which could explain the compound potency to inhibit AChE and BChE.

NMR Relaxation Study of Segmental Motions in Polymer-n-Alkanes

  • Chung Jeong Yong;Lee Jo Woong;Park Hyungsuk;Chang Taihyun
    • Bulletin of the Korean Chemical Society
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    • v.13 no.3
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    • pp.296-306
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    • 1992
  • $^{13}C$ spin-lattice relaxation times were measured for n-alkanes of moderate chain length, ranging from n-octane to n-dodecane, under the condition of proton broad-band decoupling within the temperature range of 248-318 K in order to gain some insight into basic features of segmental motions occurring in long chain ploymeric molecules. The NOE data showed that except for methyl carbon-13 dipole-dipole interactions between $^{13}C$ and directly bonded $^1H$ provide the major relaxation pathway, and we have analyzed the observed $T_1data$ on the basis of the internal rotational diffusion theory by Wallach and the conformational jump theory by London and Avitabile. The results show that the internal rotational diffusion constants about C-C bonds in the alkane backbone are all within the range of $10^9\;-10^10\;sec^{-1}$ in magnitude while the mean lifetimes for rotational isomers are all of the order of $10^{-11}\;-10^{-10}$ sec. Analysis by the L-A theory predicts that activation energies for conformational interconversion between gauche and trans form gradually increase as we move from the chain end toward the central C-C bond and they are within the range of 2-4 kcal/mol for all the compounds investigated.

Antaroide, a Novel Natural Nine-Membered Macrolide, Inhibits Melanin Biosynthesis in B16F10 Murine Melanoma Cells

  • Ryu, Min-Ji;Baek, Eun-Ki;Kim, Soyeon;Seong, Chi Nam;Yang, Inho;Lim, Kyung-Min;Nam, Sang-Jip
    • Biomolecules & Therapeutics
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    • v.29 no.1
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    • pp.98-103
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    • 2021
  • The demand for natural substances with anti-melanogenic activity is increasing due to the recent interest in skin whitening. Intensive investigation on the culture broth of Streptomyces sp. SCO-736, a marine bacterium from the Antarctica coast, has led to the isolation of a new natural product named antaroide (1). The chemical structure was established through the interpretation of MS, UV, and NMR spectroscopic data. Antaroide is a nine-membered macrolide with lactone and lactam moieties. To investigate its applicability in skin whitening cosmetics, its anti-melanogenic activity in B16F10 murine melanoma cells was examined. As a result, antaroide displayed strong inhibitory activities against melanin synthesis and also attenuated the dendrite formation induced by the α-melanocyte stimulating hormone (α-MSH). Antaroide suppressed the mRNA expression of the melanogenic enzymes such as tyrosinase, TRP-1 and TRP-2. This suggests that it may serve as a transcriptional regulator of melanogenesis. Collectively, the discovery of this novel natural nine-membered macrolide and its anti-melanogenic activity could give new insights for the development of skin whitening agents.

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.

Inhibitory Effects of Forsythia velutina and its Chemical Constituents on LPS-induced Nitric Oxide Production in BV2 Microglial Cells

  • Kim, Na-Yeon;Ko, Min Sung;Lee, Chung Hyun;Lee, Taek Joo;Hwang, Kwang-Woo;Park, So-Young
    • Natural Product Sciences
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    • v.28 no.3
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    • pp.153-160
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    • 2022
  • Neuroinflammation is known to be associated with brain injury in Alzheimer's disease (AD), and the inhibition of microglial activation, a key player in inflammatory response, is considerd as important target for AD. In this study, the ethanol extract of aerial parts of Forsythia velutina Nakai, a Korean native species, significantly inhibited nitric oxide (NO) production in LPS-stimulated BV2 microglial cells. Thus, the active principles in F. velutina aerial parts were isolated based on activity-guided isolation method. As a result, six compounds were isolated and their structures were elucidated based on NMR data and the comparison with the relevant references as arctigenin (1), matairesinol (2), rengyolone (3), ursolic acid (4), secoisolariciresinol (5), and arctiin (6). Among them, four compounds including arctigenin (1), matairesinol (2), secoisolariciresinol (5), and arctiin (6) significantly inhibited NO production in a dose-dependent manner. In particular, matairesinol (2) and secoisolariciresinol (5) reduced 60% of NO production compared to LPS-treated group. This inhibitory effects of matairesinol (2) and secoisolariciresinol (5) were accompanied with the reduced expression levels of iNOS and COX-2. These results suggest that the extract of F. velutina and its active compounds could be beneficial for neuroinflammatory diseases including AD.

Quantitative Analysis of Antioxidants in Sesame Seed (참깨 종실의 항산화 성분 정량분석 연구)

  • Ryu, Su-Rho;Lee, Jung-Il;Kang, Sam-Sik;Choi, Chang-Yoel
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.37 no.4
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    • pp.377-382
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    • 1992
  • This study was conducted to obtain basic informations on the lignan components from sesame seed. Two major lignans, sesamin and sesamolin, were isolated and identified by means of spectral methods, and quantitative analysis was by HPLC from sesame variety Danbaeggae. Separation was achieved by isocratic elution and reversed phase chromatography Develosil ODS column. The content of the major lignan components were about 0.42% and 0.30% for sesamin and sesamolin, respectively.

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A Study on the Thernal Conductivity Characteristics of Discarded Tire Powder-Soil Mixture (폐타이어 파우더 혼합토의 열전도율 특성에 관한 연구)

  • Kim, Hak-Sam;Seo, Sang-Youl;NakamuRa, Dai;Yamashita, Satoshi;Suzuki, Teruyuki
    • Journal of the Korean Geotechnical Society
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    • v.26 no.5
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    • pp.27-36
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    • 2010
  • Thermal conductivities using the thermal probe method were determined for frost susceptible soil with three types of discarded tire powder under the condition of a temperature variation from $-20^{\circ}C{\sim}+10^{\circ}C$. Also, the amount of unfrozen water contents was measured by the pulsed NMR method. The variation of unfrozen water content in the experimental condition could be expressed as a function of temperature given by an exponential equation. A new model for calculating the thermal conductivity of frozen soil was proposed. It is extended from the two element method and subdivided into three constituent elements.

Application of SiO2 nanocomposite ferroelectric material in preparation of trampoline net for physical exercise

  • Zhanguo Su;Junyan Meng;Yiping Su
    • Advances in nano research
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    • v.14 no.4
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    • pp.355-362
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    • 2023
  • Physical exercise, especially intense exercise and high intensity interval training (HIIT) by trampoline, can lead to muscle injuries. These effects can be reduced with intelligent products made of nanocomposite materials. Most of these nanocomposites are polymers reinforced with silicon dioxide, alumina, and titanium dioxide nanoparticles. This study presents a polymer nanocomposite reinforced with silica. As a result of the rapid reaction between tetraethyl orthosilicate and ammonia in the presence of citric acid and other agents, silica nanostructures were synthesized. By substituting bis (4-amino phenoxy) phenyl-triptycene in N, N-dimethylformamide with potassium carbonate, followed by catalytic reduction with hydrazine and Pd/C, the diamine monomer bis (4-amino phenoxy) phenyl-triptycene is prepared. We synthesized a new polyaromatic (imide) with triptycene unit by sol-gel method from aromatic diamines and dianhydride using pyridine as a condensation reagent in NMP. PI readily dissolves in solvents and forms robust and tough polymer films in situ. The FTIR and NMR techniques were used to determine the effects of SiO2 on the sol-gel process and the structure of the synthesized nanocomposites. By using a simultaneous thermal analysis (DTA-TG) method, the appropriate thermal operation temperature was also determined. Through SEM analysis, the structure, shape, size, and specific surface area of pores were determined. Analysis of XRD results is used to determine how SiO2 affects the crystallization of phases and the activation energy of crystallization.

Phytochemical Identification of Bioactive Constituents of Dendrobii herba (생약석곡(Dendrobii herba)의 생리활성 성분 규명)

  • Bomi Nam
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2023.04a
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    • pp.18-18
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    • 2023
  • Two new phenanthrenes, namely, (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one (1) and 2,7-dihydroxyphenanthrene-1,4-dione (2), were isolated from the ethyl acetate-soluble fraction of Dendrobii Herba, together with the eleven known compounds, densiflorol B (3), 6,7-dimethoxyphenanthrene2,5-diol (4), dehydroorchinol (5), 1,5,7-trimethoxy-2-phenanthrenol (6), denthyrsinin (7), ephemerantol A (8), lusianthridin (9), moscatilin (10), gigantol (11), 3-[(1E)-2-(3-hydroxyphenyl)ethenyl]-5-methoxyphenol (12) and (-)-syringaresinol (13). Structures of 1 and 2 were elucidated by analyzing 1D and 2D NMR as well as HR-ESI-MS data. The absolute configuration of compound 1 was confirmed by ECD spectroscopic method. In cytotoxicity evaluation using FaDu human hypopharyngeal squamous carcinoma cell line, compounds 3-6, 8, 10 and 12 showed activities, with IC50 values ranging from 2.55 to 17.70 μM. Among them, compound 10 exhibited remarkable cytotoxic activity with IC50 value of 2.55 μM. This is the first report on the anticancer mechanistic study of compound 10 in HNSCC including FaDu cells.

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Synthesis, characterization, and biological significance of mixed ligand Schiff base and alizarin dye-metal complexes

  • Laith Jumaah Al-Gburi;Taghreed H. Al-Noor
    • Analytical Science and Technology
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    • v.37 no.4
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    • pp.239-250
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    • 2024
  • This study reports the synthesis of a bi-dentate Schiff base ligand (L), 7-(2-((2-formylbenzylidene) amino)-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, prepared from phthalaldehyde and cephalexin antibiotic. The synthesized Schiff base ligand (L) and the secondary ligand alizarin (Az) are used to prepare the new complexes [M(Az)2(L)] and [Cr(Az)2(L)]Cl, where M = Mn(II), Co(II), Ni(II), Cu(II), and Zn(II). The mode of bonding of the Schiff base has been characterized by UV-Visible, FT-IR, Mass, 1H-, and 13C-NMR spectroscopic techniques, and micro elemental analysis (CHNS). The complexes were characterized using UV-Vis, FT-IR, molar conductance, magnetic moment, and thermal analysis (TG/DTG). The molar conductance data revealed that the complexes are non-electrolytes except for [Cr(L)(Az)2]Cl, which is an electrolytic type 1:1. The Schiff base and its complexes have been tested for their biological activity against two strains of bacteria and one fungus. When screened against gram-positive and gram-negative pathogens, the Az and L ligands and their complexes showed potential antimicrobial activity.