• Title/Summary/Keyword: $^{13}C$-NMR

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Micellar Properties of Two-Headed Anionic Surfactants (헤드그룹이 두 개인 음이온성 계면활성제의 미셀특성)

  • Kim, Myeong-Soo;Jeong, Kwan-Kyeong;Jeong, Noh-Hee;Nam, Ki-Dae
    • Journal of the Korean Applied Science and Technology
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    • v.18 no.2
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    • pp.111-117
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    • 2001
  • Density, viscosity, conductance, dye solubility and carbon-13 nmr studies were performed in aqueous solution of three disodium 4-n-alkyl-3-sulfonatosuccinate anionic surfactant at $20^{\circ}C$. The cmc values were 0.14 mol/l for the disodium-4-n-octyl-3-sulfonatosuccinate($R_{8)S$), 0.041mol/l for the disodium-4-n-decyl-3-sulfonatosuccinate($R_{10}S$), and 0.018mol/l for the disodium-n-dodecyl-3-sulfonatosuccinate <$R_{12}S$). The aggregation numbers determined viscometrically and conductimetrically were 28 for $R_{8}S$, 48 for $R_{10}S$, and 67 for $R_{12}S$. The volume changes upon micellization were $8.9cm^{3}/mol$ for $R_{8}S$, $9.5cm^{3}/mol$ for $R_{10}S$, and $10.1cm^{3}/mol$ for $R_{12}S$. Binding constants for the dye pada to the micelles and the fractions of unbound counter-ion were also obtained. The two polar heads with their carbon linkage were likely in an aqueous environment in the $R_{8}S$ micelles with the micelles themselves being spherical.

Antibacterial Activity of Salvia Miltiorrhiza against Methicillin-resistant Staphylococcus aureus (丹參의 methicillin 내성 황색포도구균에 대한 효과)

  • Seo, Myung-won;Jeong, Seung-il;Shin, Chol-gyun;Ju, Young-sung;Kim, Hong-jun;Ko, Byoung-seob
    • The Journal of Korean Medicine Ophthalmology and Otolaryngology and Dermatology
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    • v.16 no.1
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    • pp.94-99
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    • 2003
  • Objectives : Gram-positive bacteria have became increasing resistant to antibacterial agents, and hence multi-drug-resistant bacterial pathogens are now a major problem in clinical medicine. There is, therefore, a need for new antibacterial agents. In the course of our screening program for potent antibacterial agent from medicinal plants, the extract of Salvia miltiorrhiza (S. miltiorrhiza) showed antibacterial activity against methcillin resistant Staphylococcus aureus (MRSA) and antibiotic-resistant S. aureus. Methods : S. miltiorrhiza was extracted with 80$\%$ EtOH. The extract was suspended in H2O and fractionated successively with hexane chloroform, ethyl acetate, and n-buthanol. The chloroform fraction, which showed the highest antibacterial activity(MICs, 78㎍/ml) against MRSA, was chromatographed on a silica gel column and recycling prep-LC to give the pure antibacterial component. Results and Conclusions : The second fraction among the chloroform soluble portion of an aqueous EtOH extract of S. miltiorrhiza root showed outstanding antibacterial activity against MRSA and antibiotic-resistant S. aureus compared to the other fraction. An active compound was isolated from the second fraction using silica gel column chromatoraphy and recycling prep-LC. Based on these data together with the IH-, 13C-NMR, mass and mp, the active compounds were identified tanshinone Ⅰ, dehydrotanshinone Ⅰ and cryptotanshinone. Among tanshinones, cryptotanshinone and dihydrotanshinone Ⅰ MICs against MRSA and antibiotics-resistant S. aureus were 12.5, 12.5 and 6.3㎍/ml, respectively.

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Synthesis and Antitumor Evaluation of N-Alkyl-N-Nitrosocarbamoyl-$\alpha$-Amino- and 3$\beta$-Amino-$\alpha$-Cholestane Derivatives (N-Alkyl-N-Nitrosocarbamoyl-3$\alpha$-Amino-와 3$\beta$-Amino-5$\alpha$-Cholestane 유도체들의 합성 및 항암작용 평가)

  • 김정균;최순규;조인섭;유동식;유성호;문경호
    • YAKHAK HOEJI
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    • v.29 no.2
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    • pp.62-69
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    • 1985
  • The isomeric intermediates, $3{\alpha}$and $3{\beta}-amino-5{\alpha}-cholestane required for the synthesis of N-nitrosoureas, N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\alpha}-amino-5{\alpha}$-cholestane (9), N-methyl-N-nitrosocarbamoyl-3${\alpha}-amino-5{\alpha}-cholestane$ (10), N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$: (7), and N-methyl-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$ (8) were obtained through the $LiAlH_{4}$ reduction of $5{\alpha}$-cholestan-3-one oxime, followed by the chromatographic separation: the assignment of the stereochemistry of both isomers were based on the shape and chemical shift of $C_{3}$-proton resonances on their NMR spectra and on the elution mobility on the TLC. The urea intermediates, N-(2-chloroethyl) carbamoyl-3.alpha.-amino-5.alpha.-cholestane (13), N-methylcarbamoyl-$3{\alpha}-amino-5{\alpha}-cholestane$ (14), N-(2-chloroethyl) carbamoyl-$3{\beta}-amino-5{\alpha}-cholestane (11) and N-methyl-$3{\beta}-amino-5{\alpha}$-cholestane (12) were prepared by the treatment of each isomers ($3{\alpha}$-amino-and $3{\beta}-amino-5{\alpha}$-cholestane) with alkyl isocyanates in anhydrous $CHCl_{3}$, and the corresponding nitrosoureas, 7-10 were obtained by the nitrosation of the ureas, 11-14, with AcOH (or HCOOH)/$NaNO_{2}$ in ice-cold condition. The inhibitory activity of the nitrosoureas, 7-10, and their intermediates, 12-14 towards the growth of L1210 murine leukemia cells, were examined. Among them, the compounds 9 and 10 exhibited high activity having $ED_{50}$ to be 5.5g/ml and 6.1g/ml, respectively.

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Isolation and Quantitative Analysis of Schisandrin, Gomisin A and Gomisin M2 From Schisandra chinensis (오미자로부터 Schisandrin, Gomisin A, Gomisin M2의 분리 및 함량 분석)

  • Kim, Yeong-Eun;Kim, Eun-Nam;Jeong, Gil-Saeng
    • Korean Journal of Pharmacognosy
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    • v.50 no.2
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    • pp.148-153
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    • 2019
  • The lignan compound of Schisandra chinensis Baill. (Schizandraceae) has been reported to have a variety of biological activities such as liver protection, neuroprotection, anti-oxidant and anti-diabetes. In this study, we investigated a quantitative analytical method for schisandrin, gomisin A and gomisin $M_2$ isolated from S. chinensis by high-performance liquid chromatography-ultraviolet spectroscopy (HPLC-UV). The isolated compounds were identified by the analysis of 1H- and 13C-NMR spectroscopic data. The results showed that calibration curves of three compounds indicated great linearity with a correlation coefficient ($R^2$) of schisandrin 0.9983, gomisin A 0.9982 and gomisin $M_2$ 0.9986. The limits of detection (LOD) of schisandrin, gomisin A and gomisin $M_2$ were 0.14, 0.07 and $0.05{\mu}g/ml$ and the limits of quantification (LOQ) were 0.42, 0.22 and $0.14{\mu}g/ml$. Intra-day and inter-day precisions of schisandrin were 0.40~1.44%, 0.07~1.02% gomsin A were 0.22~0.52%, 0.10~0.63%, gomisin $M_2$ were 0.40~0.99%, 0.81~2.88%. In result, contents of schisandrin, gomisin A and gomisin $M_2$ in ethanol extract of S. chinensis were $25.95{\pm}0.15$, $2.51{\pm}0.02$ and $2.17{\pm}0.07mg/g$.

Sesquiterpenoids from the Stem Bark of Aglaia grandis

  • Harneti, Desi;Permatasari, Atika Ayu;Anisshabira, Amallya;Naini, Al Arofatus;Nurlelasari, Nurlelasari;Mayanti, Tri;Maharani, Rani;Safari, Agus;Hidayat, Ace Tatang;Farabi, Kindi;Supratman, Unang;Azmi, Mohamad Nurul;Shiono, Yoshihito
    • Natural Product Sciences
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    • v.28 no.1
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    • pp.6-12
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    • 2022
  • Five sesquiterpenoids, 7-epi-eudesm-4(15)-ene,1β,6α-diol (1), 7-epi-eudesm-4(15)-ene,1β,6α-diol (2), saniculamoid D (3), aphanamol I (4), and 4β,10α-dihydroxyaromadendrane (5), were isolated from the stem bark of Aglaia grandis. The compounds' (1-5) chemical structures were identified by spectroscopic data including, IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, 1H-1H COSY), and HRTOFMS, as well as by comparing with the previously reported spectral data. Therefore, this study described the structural elucidation of compounds 1-5 and evaluated their cytotoxic effects against Hela cervical and B16F10 melanoma cells for the first time, but no significant result was discovered.

Biological Activities and Bioactive Compounds in the Extract of Acer tegmentosum Maxim. Stem (산겨릅나무 줄기추출물의 생리활성 및 유효성분 분리)

  • Hong, Bo-Kyong;Eom, Seok-Hyun;Lee, Chan-Ok;Lee, Ji-Won;Jeong, Jong-Hyun;Kim, Jae-Kwang;Cho, Dong-Ha;Yu, Chang-Yeon;Kwon, Yong-Soo;Kim, Myong-Jo
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.4
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    • pp.296-303
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    • 2007
  • Acer tegmentosum (Acereaceae) has been used a source of traditional medicines for the treatment of hepatic disorders in Korea. This research was conducted to determine biofunctional activities of A. tegmentosum stem extract and to identify its bioactive components. Methanolic extract from A. tegmentosum stem was partitioned by using organic solvents, including n-hexane, ethyl acetate, n-butanol, and water. Two compounds were isolated by using an ODS column chromatography from ethyl acetate soluble fraction shown to the strongest antioxidant activity ($RC_{50}=3.15\;{\mu}g/m{\ell}$) among the fractions. The isolated compounds were analyzed by $^1H$ and $^{13}C$ NMR, IR, UV/VIS, MS spectrum data and identified as catechin, ${\rho}-Hydroxyphenethyl$ alcohol $1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$. The compounds have shown strong antioxidant activity, with similar activity to BHA ($RC_{50}=2\;{\mu}g/m{\ell}$). Especially, ${\rho}-Hydroxyphenethyl$ alcohol 1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$ was shown strong anti-lipid peroxidative activity. However, the compounds were not shown antimicrobial activities. In antimicrobial activity assays, ethyl acetate soluble fraction was effective to bacterial inhibition, such as Escherichia coli and Klebsiella pneumonia, with minimum inhibitory concentrations in $125\;{\mu}g/m{\ell}$. Otherwise, antifungal activity against Candida albicans was shown in n-hexane soluble fraction exhibiting $63\;{\mu}g/m{\ell}$ of minimum inhibitory concentration. In anticomplementary activity assays, water soluble fraction was the most effective exhibiting 24% inhibitory activity.

Preparation of (n-BuCp)2ZrCl2 Catalyst Supported on SiO2/MgCl2 Binary Support and its Ethylene-1-hexene Copolymerization (SiO2/MgCl2 이원 담체에 담지된 (n-BuCp)2ZrCl2 합성과 에틸렌-1-헥센 공중합)

  • Carino, Ann Charise;Park, Sang Jun;Ko, Young Soo
    • Applied Chemistry for Engineering
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    • v.29 no.4
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    • pp.461-467
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    • 2018
  • In this study, $(n-BuCp)_2ZrCl_2$, was supported on $SiO_2/MgCl_2$ binary support. Before supporting the catalyst, the $SiO_2/MgCl_2$ binary support was surface treated with three different alkyl aluminum compound, namely trimethylaluminum, triethylaluminum, and ethylaluminum sesquichloride. The synthesized surface-treated $SiO_2/MgCl_2$ supported metallocene catalysts were used for the copolymerization of ethylene and 1-hexene. Their catalytic properties and performances were analyzed through BET, XPS analysis, ICP-AES analysis, and FE-SEM. While the resulting copolymers were analyzed through DSC analysis, GPC analysis, 13C-NMR analysis, and FE-SEM. The analysis of synthesized surface-treated $SiO_2/MgCl_2$ supported metallocene catalysts showed that the Zr content of these catalysts is relatively lower compared to that of the catalyst supported on $SiO_2$. This could be attributed to the reduction in the surface area of $SiO_2$ due to the presence of recrystallized $MgCl_2$ and alkyl aluminum. Furthermore, they exhibited a better copolymerization activity compared to that of $SiO_2$ supported catalyst, particularly the EASC-surface treated binary support, which has the highest activity of 1.9 kg PE/($mmol-Zr^*hr$) because EASC acts as a strong Lewis acid. It could also be observed that the larger the ligand of alkyl aluminum used, the rougher the particle surface of the resulting polymer.

Simultaneous HPLC Determination of Marker Compounds for the Standardization of Hedyotis diffusa (백운풀의 지표성분 설정 및 품질표준화를 위한 정량 분석법)

  • Bang, Han-Yeol;Yang, Eun-Ju;Kim, Jeong-Ah;Song, Kyung-Sik
    • Journal of Life Science
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    • v.23 no.8
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    • pp.1025-1031
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    • 2013
  • From a 95% ethanolic extract of H. diffusa, four marker compounds (HD1~HD4) were isolated, which were relatively unique and exist in comparably high contents. The structures of marker compounds were identified as digitolutein (1), 2-hydroxy-3-methylanthraquinone (2), (E/Z)-6-O-p-coumaroyl scandoside methyl ester (4:1 mixture) (3), and (E/Z)-6-O-p-methoxycinnamoyl scandoside methyl ester (4:1 mixture) (4), respectively, on the basis of $^{13}C$ and $^1H$-NMR analyses. The calibration curves of marker compounds showed high linearity, as their correlation coefficient ($R^2$) were in the range of 0.9991~0.9999. In addition, the limit of detection (LOD) and the limit of quantification (LOQ) were $0.03{\sim}0.07{\mu}g/ml$ and $0.099{\sim}0.231{\mu}g/ml$, respectively. The intra-day/inter-day precision and accuracy were 0.23~2.00%/0.25~1.16% and 94.60~108.44%/94.73-110.23%, respectively. The optimal HPLC conditions for the simultaneous quantification of HD1~HD4 were as follows: stationary phase; Merck Chromolith RP-18e ($100{\times}4.6mm$, $5{\mu}m$), column temp.; room temperature, UV detection at 280 nm, flow rate; 2.0 ml/min, injection volume; $10{\mu}l$, mobile phase; start with the mixture of 80% solvent A ($H_2O$ containing 0.5% acetic acid) and 20% solvent B (methanol containing 0.5% acetic acid) and gradually decrease solvent A to 40% in 9 min., then retain this condition to 18 min. Under the HPLC condition, the four marker compounds 1~4 were successfully separated without any interference of other constituents. The results obtained in this study are expected to be helpful for the development of nutraceutics and natural medicines and for the quality control of this plant.

Identification of Growth Inhibitory Substance on Food-borne Microorganisms from Commiphora molmol Engl. and Its Application to Food Products (몰약(Commiphora molmol Engl.)의 식중독 미생물 증식 억제 물질의 구조동정 및 식품적용)

  • Han, Ji-Sook;Shin, Dong-Hwa;Baek, Nam-In
    • Korean Journal of Food Science and Technology
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    • v.33 no.4
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    • pp.401-408
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    • 2001
  • The ethanol extract and n-hexane fraction of Commiphora molmol Engl. showed minimum inhibitory concentration of 50 ppm and 25 ppm, respectively, on 5 strains of Listeria monocytogenes at $32^{\circ}C$. The purified substance, C3-3-2 fraction, was isolated by silica gel column and preparative thin layer chromatography from n-hexane fraction of Commiphora molmol Engl. The C3-3-2 fraction showed a strong bactericidal activity on 5 strains of L. monocytogenes at the concentration of 10 ppm in tryptic soy broth medium. At that concentration, the viable count was reduced $5{\sim}6$ log cycle from initial cell number. The n-hexane fraction of Commiphora molmol Engl. showed strong growth inhibition at the concentration of 25 ppm on Bacillus cereus and Staphylococcus aureus, at 50 ppm in broth on Salmonella enteritidis, and at 500 ppm on Vibrio parahaemolyticus. The purified antimicrobial substance, the C3-3-2 fraction, was identified as m-nonylphenol by on the basis of the $^1H-,\;^{13}C-NMR$ and EI/MS data. For the application test, the C3-3-2 fraction which was purely isolated from Commiphora molmol Engl. at 100 ppm were applied to minced Alaska pollack and ground beef at $32^{\circ}C$ and $5^{\circ}C$. The antimicrobial substances did not reduce L. monocytogenes ATCC 19113 at $32^{\circ}C$, while they reduced L. monocytogenes ATCC 19113 in viable number at $5^{\circ}C$. However, the antimicrobial effect of C3-3-2 fraction in food system was lower than that of broth condition.

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Antigenotoxicity of Ginseng Petroleum Ether Extract and its Action Mechanism (인삼 지용성성분인 유전독성억제효과와 작용기전)

  • 허문영
    • Journal of Food Hygiene and Safety
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    • v.13 no.3
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    • pp.243-251
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    • 1998
  • Panax ginseng C.A. Meyer has been extensively used in the traditional oriental medicine as a restorative, tonic and prophylatic agent. Petroleum ether extract of panax ginseng C.A. Meyer (GPE) and its several fractions (PI-P5) were tested for the evaluation of antigenotoxicity against N-methyl-N-nitrosourea (MNU) and benzo(a)pyrene [B(a)P]-induced micronucleated reticulocytes in mouse peripheral blood. GPE and P2 showed more significant anticlastogenicity than other fractions did. To elucidate the anticlastogenic action mechanism of GPE and P2 against B(a)P, the alteration of B(a)P metabolism was studied. GPE and P2 inhibited B(a)P metabolism in the presence of 8-9 mix and decreased B(a)P-DNA binding in calf thymus DNA with 8-9 mix. They also decreased [$^3H$] MNU induced DNA binding and methylation to 7-methyl guanine and $O^{6}-methyl$ guanine adducts in calf thymus DNA by RPLC analysis. These results suggest that the anticlastogenicity of GPE and P2 on the B(a)P or MNU-induced clastogenicity is due to decrease of DNA binding with B(a)P or MNU, the inhibition of metabolism with B(a)P and the inhibition of methylation in DNA. Therefore, GPE and P2 may be useful chemopreventive agents of alkylating agent like MNU and secondary carcinogen like B(a)P.

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