• Title/Summary/Keyword: $^{13}C-NMR$ data

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Anti-oxidative Activities for the Flavonoids of the Syzygium aqueum Burm.f. Alston Branches from Jeju Island (제주 자생 물사과 가지 유래 Flavonoid 화합물의 항산화 활성)

  • Yeom, Hyun Sook;Lee, Nam Ho;Hyun, Ju Mi
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.44 no.2
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    • pp.151-159
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    • 2018
  • In this study, we investigated the anti-oxidative activities and cell protective effects of the constituents isolated from S. aqueum branches. DPPH and $ABTS^+$ radical scavenging activities were screened for the ethanol extract and solvent fractions, ethyl acetate (EtOAc) and butanol (BuOH) fractions showed potent activities. When HaCaT cells were treated with $H_2O_2$, the ethanol extract and EtOAc fractions ($20{\mu}g/mL$) protected the cells against oxidative damage. Two constituents were isolated from the EtOAc fraction of S. aqueum branches; pinocembrin (1), desmethoxymatteucinol (2). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Anti-oxidative activities and cell protective effects were studied for the isolated compounds. For the anti-oxidative activities, all of the compounds 1 and 2 showed DPPH and $ABTS^+$ radical scavenging activities. Also, from the cell protective effect test, the compounds 1 and 2 protected the cell against oxidative stress by $H_2O_2$. Based on these results, S. aqueum branches extract could be potentially applicable as anti-oxidant ingredients in cosmetic industries.

Anti-melanogenesis Activities for the Terpenes from the Acantophanax koreanum Stems (섬오갈피나무 줄기 유래 테르펜 화합물의 멜라닌 생성 저해 활성)

  • Mun, Seung Ri;Hyun, Ju Mi;Jo, Yeon Jeong;Jung, Eun Yeong;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.43 no.4
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    • pp.289-295
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    • 2017
  • A. koreanum was investigated to identify the constituents possessing whitening effects. As anti-melanogenesis activities were screened for the ethanol extract and solvent fractions, n-hexane (Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex fraction of A. koreanum; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oicacid (2), $16{\alpha}$-hydroxy-17-isovaleroyl-oxy-ent-kauran-19-oic acid (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening effects were studied for the isolated compounds. Upon the anti-melanogenesis test using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1, 2 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. Based on these results, A. koreanum stems extract could be potentially applicable as whitening ingredients in cosmetic formulations.

Anti-inflammatory and Anti-bacterial Constituents from the Extracts of Daucus carota var. sativa Aerial Parts (당근 지상부 추출물 유래 항염 및 항균 활성 성분)

  • Kim, Jung Eun;Jo, Yeon Jeong;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.44 no.4
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    • pp.427-436
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    • 2018
  • In this study, we investigated anti-inflammatory and anti-bacterial constituents from Daucus carota var. sativa (carrot) areal parts. For the extract and solvent fractions, the anti-inflammatory activities were examined by measuring the nitric oxide (NO) production using LPS-stimulated RAW 264.7 cells. Among them, the ethyl acetate (EtOAc) fraction decreased the NO level in a dose-dependent manner. To elucidate further anti-inflammatory mechanisms, EtOAc fraction was evaluated by estimating their effects on the production of prostaglandin $E_2$ and pro-inflammatory cytokines as well as on the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). As a result, the EtOAc fraction was determined to inhibit the production of $PGE_2$, IL-$1{\beta}$, IL-6 and reduce the iNOS, COX-2 protein expression. Upon the anti-bacterial tests using Staphylococcus epidermidis and Propionibacterium acnes, n-hexane (Hex) and EtOAc fractions showed the most potent activities. Three phytochemicals were isolated form the EtOAc fraction; diosmetin (1), diosmin (2), cynaroside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literatures. Anti-inflammatory and anti-bacterial effects were studied for the isolates. All of the compounds (1 - 3) decreased the NO production, effectively. Also, compound 3 showed anti-bacterial activity on P. acnes. Based on these results, D. carota var. sativa extract could be potentially applicable as anti-inflammatory and anti-bacterial ingredients in cosmetic formulations.

Isolation of Dibromosceptrin with Antimalarial Activity from the Unidentified Sponge, Agelas sp. (Agelas속의 미동정 해면으로부터 항말라리아 활성을 갖는 Dibromosceptrin의 분리)

  • Park, Yeung-Beom;Lee, Jong-Soo;Lim, Chi-Won
    • Korean Journal of Pharmacognosy
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    • v.35 no.3 s.138
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    • pp.189-193
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    • 2004
  • In order to find some lead compounds for the treatment of opportunistic infections of malaria and pathogenic microbes, an undescribed Indonesian sponge Agelas sp. collected at Manado, Indonesian Waters, was suggested containing active compounds. Crude ethanolic extract of the sponge exhibited significant in vitro antimalarial and antimicrobial activity against Plasmodium falciparum (D6 colne) with $IC_{5O}$ values of $8\;{\mu}/ml$ and against pathogenic microbes such as Candida albicans $(150\;{\mu}/ml)$, Cryptococcus neoformans $(<20\;{\mu}/ml)$, Staphylococcus aureus $25\;{\mu}/ml$, methicillin-resistant Staphylococcus aureus $(<20\;{\mu}/ml)$, and Pseudomonas aeruginosa $(<20\;{\mu}/ml)$. Active compound (5.0 mg) was isolated from the ethanolic extracts of the sponge and purified by using silica gel and ODS column, successively. Active compound was elucidated as dibromosceptrin $(C_{22}H_{24}Br_2N_{10}O_2)$ by detailed analysis of FTESI-MS and comparison of $^1H,\;^{13}C$, DEPT and HMQC NMR spectral data with those reported.

Spectroscopic, Thermal and Biological Studies of Zn(II), Cd(II) and Hg(II) Complexes Derived from 3-Aminopyridine and Nitrite Ion

  • Dhaveethu, Karuthakannan;Ramachandramoorthy, Thiagarajan;Thirunavukkarasu, Kandasamy
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.712-720
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    • 2013
  • Microwave assisted syntheses of Zn(II), Cd(II) and Hg(II) complexes with 3-aminopyridine (3AP) and nitrite ($NO_2{^-}$) ions have been reported. The metal complexes were characterized by elemental analyses, molar conductance, IR, Far-IR, electronic, NMR ($^1H$, $^{13}C$), thermal and electron impact mass spectral studies. The spectroscopic studies reveal the composition, the nature of nitrite ligand in the complexes, electronic transitions, chemical environments of C and H atoms thermal degradation of the complexes. On the basis of characterization data, distorted tetrahedral geometry is suggested for Zn(II), Cd(II) and Hg(II) complexes. The organic ligand (3AP) and their metal complexes were screened against gram negative pathogenic bacteria and fungi in vitro. The results are compared with our previous report J. Korean Chem. Soc. 2013, 57, 341 on 4-aminopyridine and nitrite ion complexes of the same metal ions.

Chemical Constituents of Impatiens balsamina Stems and Their Biological Activities

  • Kim, Dong Hyun;Lee, Tae Hyun;Subedi, Lalita;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
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    • v.25 no.2
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    • pp.130-135
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    • 2019
  • The purification of the MeOH extract from Impatiens basamina by repeated column chromatography led to the isolation of one new tetrahydronaphthalene (1), together with eleven known compounds (2 - 12). The structure of the new compound (1) was determined by spectral data analysis ($^1H$ and $^{13}C$-NMR, $^1H-^1H$ COSY, HSQC, HMBC, NOESY, and HR-ESI-MS). Isolated compounds (1 - 12) were evaluated for their inhibitory effects on NO production in LPS-activated murine microglial BV-2 cells and their effects on NGF secretion from C6 glioma cells. Compounds 3, 7, and 10 reduced NO levels in LPS-activated murine microglial cells with $IC_{50}$ values of 26.89, 25.59, and $44.21{\mu}M$, respectively. Compounds 1, 5, and 9 upregulated NGF secretion to $153.09{\pm}4.66$, $156.88{\pm}8.86$, and $157.34{\pm}3.30%$, respectively.

An NMR Study on Internal Rotation of $CH_3$ Group in 1,1,1-Trichloroethane

  • Hyung Namgoong;Kim, Joa-Jin;Lee, Jo-Woong
    • Journal of the Korean Magnetic Resonance Society
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    • v.4 no.1
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    • pp.29-40
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    • 2000
  • Coupled carbon-13 relaxation study of 1,1,1-trichloroethane dissolved in DMSO has been performed to gain some crucial insight into the dynamics of methyl group in this compound. For this purpose the relaxation behaviors of several observable magnetization modes for CH3 spin system generated by various perturbing pulse sequences have been carefully investigated and various dipolar spectral densities were estimated by nonlinear numerical fittings of the observed data with the relaxation curves, which were then employed to determine the three principal values for the diffusion tensor for end-over-end molecular rotation as well as internal rotational parameters of methyl group. In this process we could uniquely determine two correlation times $\tau$int(1) and $\tau$int(2) which give valuable information on internal rotor dynamics and thus obtained data were interpreted on the basis of various proposed models for internal rotation. compound undergoes three-fold jumps at 25$^{\circ}$. The fact that the ratio $\tau$int(1) / $\tau$int(2) is close to 1.0 may be interpreted as indicating that methyl group in this C.

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Isolation of Flavonoids and Lignans from the Stem Wood of Lindera obtusiloba Blume (생강나무(Lindera obtusiloba Blume) 목부로부터 Flavonoid 및 Lignan 화합물의 분리)

  • Seo, Kyeong-Hwa;Baek, Mi-Young;Lee, Dae-Young;Cho, Jin-Gyeong;Kang, Hee-Cheol;Ahn, Eun-Mi;Baek, Nam-In;Lee, Youn-Hyung
    • Journal of Applied Biological Chemistry
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    • v.54 no.3
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    • pp.178-183
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    • 2011
  • The stem woods of Lindera obtusiloba Blume were extracted in 80% aqueous methanol and the concentrated extract was partitioned with ethyl acetate (EtOAc), butanol (n-BuOH), and $H_2O$, successively. From the EtOAc and n-BuOH fractions, five compounds were isolated through the repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies. On the basis of spectroscopic data including mass spectrometry, IR, $^1H$-NMR, $^{13}C$-NMR, distortionless enhancement by polarization transfer, and two-dimensional-NMR gradient correlated spectroscopy (gCOSY), gradient heteronuclear single quantum correlation (gHSQC), gradient heteronuclear multiple bonding connectivity (gHMBC), the chemical structures of the compounds were determined as asarinin (1), (+)-catechin (2), (-)-epicatechin (3), hyperin (4), and nudiposide (5). Compounds 1 and 5 were isolated for the first time from the stem wood of L. obtusiloba Blume.

Synthesis and Micellar Characterization of CBABC Type PLGA-PEO-PPO-PEO-PLGA Pentablock Copolymers

  • Seong, Haseob;Cho, Eun-Bum;Oh, Joongseok;Chang, Taihyun
    • Bulletin of the Korean Chemical Society
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    • v.35 no.8
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    • pp.2342-2348
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    • 2014
  • Poly(lactic-co-glycolic acid) (PLGA) were grafted to both ends of Pluronic$^{(R)}$ F68 ($(EO)_{75}(PO)_{30}(EO)_{75}$) triblock copolymer to produce poly{(lactic acid)$_m$-co-(glycolic acid)$_n$}-b-poly(ethylene oxide)$_{75}$-b-poly(propylene oxide)$_{30}$-b-poly(ethylene oxide)$_{75}$-b-poly{(lactic acid)$_m$-co-(glycolic acid)$_n$} (PLGA-F68-PLGA) pentablock copolymers. Molecular weights of PLGA blocks were controlled and five kinds of pentablock copolymers with different PLGA block lengths were synthesized using in-situ ring-opening polymerization of D,L-lactide and glycolide with tin(II) 2-ethylhexanoate ($Sn(Oct)_2$) catalyst. PLGA-F68-PLGA pentablock copolymers were characterized by $^1H$- and $^{13}C$-NMR, GPC, and TGA. The numbers (2m, 2n) of repeating units for lactic acid and glycolic acid inside PLGA segments were obtained as (48, 17), (90, 23), (125, 40), (180, 59), and (246, 64), with $^1H$-NMR measurement. From NMR data, the resultant molecular weights were determined in the range of 12,700-29,700, which were similar to those obtained from GPC. Polydispersity index was increased in the range of 1.32-1.91 as the content of PLGA blocks increased. TG and DTG thermograms showed discrete degradation traces for PLGA and F68 blocks, which indicate the weight fractions of PLGA blocks in pentablock copolymers can be calculated by TG profile and it is possible to remove PLGA block selectively. Hydrodynamic radius and radius of gyration of pentablock copolymer micelle were obtained in the range of 46-68 nm and 31-49 nm, respectively, in very dilute (i.e. 0.005 wt %) aqueous solution of THF:$H_2O$ = 10:90 by volume at $25^{\circ}C$.

Chemical Constituents from the Leaf and Twig of Acer okamotoanum Nakai and their Cytotoxicity

  • Jin, Wen-Yi;Min, Byung-Sun;Youn, Ui-Jung;Hung, Tran-Manh;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.2
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    • pp.77-81
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    • 2006
  • As a result of cytotoxic compounds against cancer cell lines from natural sources, senven compounds were isolated from the leaf and twig of Acer okamotoanum Nakai. The compounds (1-7) were identified as ethyl gallate (1), methyl gallate (2), gallic acid (3), trans $resveratrol-3-O-{\beta}-D-glucopyranoside$ (4), acertannin (5), nikoenoside (6), and fraxin (7) by physicochemical and spectroscopic data (including mp, UV, IR, MS, $^1H-NMR,\;^{13}C-NMR$, DEPT, and HMBC) in comparison with those of published papers. All the compounds were tested for their cytotoxic activity against L1210, HL-60, K562, and B16F10 cancer cell lines in vitro by MTT assay method. Compounds 1-3 and 5 showed cytotoxic activity against all tested cell lines with $IC_{50}$ values ranged from 12.5 to $72.2\;{\mu}M$. Of the compounds, methyl gallate (2) exhibited the most potent cytotoxic activity against L1210, HL-60, K562, and B16F10 tumor cells with $IC_{50}$ values of 12.5, 48.3, 22.8, and $22.8\;{\mu}M$, respectively. Other compounds did not show any cytotoxic activity against four cancer cell lines.