• Title/Summary/Keyword: $^{13}C$-NMR

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Spectroscopic Characterization of Soil Humic Acid Fractions by Molecular Weight (토양에서 추출한 흄산의 분자량별 분류에 따른 분광학적 성질 비교)

  • Shin, Hyun Sang;Moon, Hichung;Yang, Han Beom;Yun, Sock Sung
    • Journal of the Korean Chemical Society
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    • v.39 no.1
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    • pp.66-70
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    • 1995
  • The soil humic acid was subdivided into four subfractions by molecular weight (F1: >100.000 dalton; F2: >100.000 dalton; F3: >10.000 dalton; F4: >2.000 dalton) using MP-dual hollow fiber ultrafiltration system. The characterization using IR, 1H and 13C NMR spectroscopy, showed similar spectroscopic features of HA, demonstrating that the bulk properties of HA subfractions are very similar to one another. IR spectral data showed a decrease in polysaccharide contents and increase in carboxylate functionality as molecular weight become smaller.functions. The structure of (NO) can be described by two interactions (N${\cdot}{\cdot}{\cdot}$N, N${\cdot}{\cdot}{\cdot}$O). One is the ONNO structure with an (N${\cdot}{\cdot}{\cdot}$N) interaction. In this structure, acyclic cis-ONNO with $C_{2v}$-symmetry, acyclic trans-ONNO with $C_{2h}$, and cyclic ONNO with trapezoidal structure ($C_{2v}$) are optimized at the MP2 level. The other structure is the ONON structure with an (N${\cdot}{\cdot}{\cdot}$O) interaction. In the structure, acyclic cis-ONON with Cs$^{-symmetry}$ and cyclic ONON of the rectangular ($C_{2h}$), square $(D_{2h})$, rhombic $(D_{2h})$, and parallelogramic $(D_{2h})$ geometries are also optimized. It is found that acyclic cis-ONNO $(^1A_1$) is the most stable structure and cyclic ONNO ($^3A_1$) is the least stable. Acyclic trans-ONNO ($^3A_1$) with an (N${\cdot}{\cdot}{\cdot}$N) interaction, acyclic trans-ONON and bicyclic ONON $(C_{2v})$ with (N${\cdot}{\cdot}{\cdot}$O) interaction, and acyclic cis- and trans-NOON with an (O${\cdot}{\cdot}{\cdot}$O) interaction can not be optimized at the MP2 level. Particularly, acyclic trans-ONNO with $C_{2h}$-symmetry can not be optimized at the CCSD(T) level. Meanwhile, acyclic NNOO ($^1A_1$, $C_s)$ and trianglic NNOO ($^1A_1$,$C_{2v})$ formed by the (O${\cdot}{\cdot}{\cdot}$N) interaction between $O_2$and $N_2$are optimized at the MP2 level. The binding energies and the relative energy gaps among the isomers are found to be relatively small./sec. Spiral CT scans during the arterial phase were obtained 35 seconds after the injection of contrast medium. CT findings of 78 lesions less than 4cm in diameter were correlated with angiographic findings. Results : The attenuation of lesions was high(n = 69), iso(n = 5), and low(n = 4) compared with liver parenchyma during the arterial phase of spiral CT. In lesions with high-, iso-, and low-attenuation during the arterial phase of spiral CT, hypervascularity on angiograms was found in 63 of 69(91.3%), three of five(60%), and three of four lesions(75%), respectively. Six lesions with high-attenuation on the arterial phase of spiral CT were not seen on angiography. Two iso-attenuated and one low-attenuated lesion were hypovascular on angiograms. Conclusion : The results of this study suggest that with some exceptions there was good correlation between the arterial phase of spiral CT and angiography.

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The Effect of Ginkgo Biloba Extract on Hypoxic Fraction of C3H Mouse Fibrosarcoma (Ginkgo Biloba Extract가 C3H 마우스 섬유육종의 저산소세포 분획에 미치는 영향)

  • Cho Chul Koo;Yi Chun Ja;Ha Sung Whan;Park Charn Il
    • Radiation Oncology Journal
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    • v.13 no.3
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    • pp.205-214
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    • 1995
  • Purpose : To investigate the effect of Ginkgo biloba extract (GBE) on hypoxic cell fraction and metabolic status in fibrosarcoma (FSa II) of C3H mouse. Materials and Methods : Fibrosarcoma (FSa II) 6 mm in diameter, growing in the right hindleg muscle of C3H mouse was used for estimation of hypoxic cell fraction using comparison of $TCD_{50}$. Radiation was given one hour after administration of GBE (100 mg/kg. i.p.) with or without priming dose of GBE (100 mg/kg, i.p.) given 24 hours earlier. Radiation was also given under air breathing condition or clamp hypoxia without GBE as controls. $^{31}p$ NMR spectroscopy was performed before and one hour after administration of GBE with or without priming dose of GBE. Results : $TCD_{50/120's}$ were 81.7 (77.7-86.0) Gy when irradiated under clamped hypoxia 69.6 (66.8-72.5) Gy under air breathing condition. 67.5 (64.1-71.1) Gy with a single dose of GBE (100 mg/kg) given one hour before irradiation, and 62.2 (59.1-65.5) Gy with two doses of GBE given at 25 hours and one hour before irradiation. The hypoxic cell fractions, estimated from $TCD_{50/120's}$, were $10.6{\%}$ under air breathing condition, $7.2{\%}$ after a single dose of GBE, and $2.7{\%}$ after two doses of GBE. The results of $^{31}P$ NMR spectroscopy were as follow. PCr/Pi ratio was $0.27{\pm}0.04$ and $0.40{\pm}0.04$ before and one hour after a single dose of GBE (p<0.05), respectively, without priming dose and $0.30{\pm}0.02$ and $0.71{\pm}0.04$, respectively, with priming dose (p<0.01). These findings indicate that the metabolic status is slightly improved after a single dose and markedly after repeated administrations. Conclusion : GBE decreases the hypoxic cell fraction and imprvoes the meta bolic status of tumor, probably by increasing the blood flow and delivery of oxygen and nutrients, resulting in increased radiosensitivity of tumor.

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Isolation and Evaluation of Anti-oxidative Constituents from the Extracts of Ficus erecta var. sieboldii King Leaves (좁은잎천선과 잎 추출물 유래 항산화 활성 성분의 동정 및 효능 확인)

  • Park, Sung Hwan;Kim, Jung Eun;Yeum, Hyun Sook;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.42 no.4
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    • pp.321-328
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    • 2016
  • In this study, we investigated identification of anti-oxidative constituents from Ficus erecta var. sieboldii King (F. erecta) leaves. DPPH and $ABTS^+$ radical scavenging activities were screened for the ethanol extract and solvent fractions, and ethyl acetate fraction showed the most potent scavenging activities. Five constituents were isolated from the ethyl acetate fraction of F. erecta leaves; monoolein (1), oleic acid (2), lutein (3), afzelechin (4), catechin (5). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including NMR spectra, as well as comparison of the data to the literature values. As far as we know, all of the compounds 1 ~ 5 were isolated for the first time from this plant. Studies on DPPH and $ABTS^+$ radical scavenging activities were conducted for the isolated compounds. Among them, afzelechin (4) and catechin (5) showed strong DPPH and $ABTS^+$ radical scavenging activities, whose activities were comparable to a positive control vitamin C. Also, the content of catechin isolated from this plant was determined by HPLC and it was about 3.8 mg/g for the 70% ethanol extract and 20.8 mg/g for the ethyl acetate fraction. From these results, F. erecta leaves extract could be potentially applicable as anti-oxidant ingredients in cosmetic industries.

Isolation and Structural Determination of Anti-Helicobacter pylori Compound from Fungus 60686. (곰팡이에서 분리한 Helicobacter pylori 항균물질의 분리 및 구조규명)

  • 남궁준;연승우;백남수;김태한;김영호;김창진;김기원
    • Microbiology and Biotechnology Letters
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    • v.26 no.2
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    • pp.137-142
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    • 1998
  • Helicobacter pylori is a Gram-negative bacterium which causes chronic gastritis and is associated with gastric ulcer, duodenal ulcer and gastric carcinoma. In the process of screening of antibacterial activities against H. pylori from soil microorganisms, fungus No. 60686 was isolated. After fermentation of No.60686, the antibacterial compound was isolated, purified and followed by extraction of mycelium with organic solvents, acetone and ethyl acetate, through silica gel chromatography, LH-20 gel chromatography and HPLC. As a result of the structural analyses of the compound by IR, $^1$H- and $^{13}$C-NMR, FAB/Mass spectrophotometer, the compound having the antimicrobial activity was identified as chaetoglobosin A ($C_{32}H_{36}N_2O_5$), a cytochalasan derivative. The antimicrobial activity of chaetoglobosin A was tested against Gram-positive and negative bacteria by paper disk method. Among the test strains of 9 Gram-positive bacteria and 18 Gram-negative bacteria containing 4 H. pylori strains, the growth of 4 H. pylori strains and 3 S. aureus strains (SG 511, 285 and 503) was only inhibited by chaetoglobosin A. Also it was shown that its growth inhibition against H. pylori strains was stronger than that against S. aureus strains at the treatment of the same concentration. Therefore it was concluded that chaetoglobosin A has a specific growth inhibition against H. pylori of the tested bacteria.

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Application of Isolated Tyrosinase Inhibitory Compounds from Persimmon Leaves (감나무 잎으로 부터 분리한 tyrosinase 억제물질의 응용)

  • Cho, Young-Je;An, Bong-Jeun;Kim, Jeung-Hoan
    • Journal of Life Science
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    • v.21 no.7
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    • pp.976-984
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    • 2011
  • Total phenolic content was the highest in 60% ethanol extracts at 21.91 mg/g, and inhibitory activity against tyrosinase of 60% ethanol extracts was higher than ethanol extracts of other concentration. The inhibitory compounds against tyrosinase from Persimmon leaves were purified using Sephadex LH-20, MCI-gel CHP-20 column chromatography with gradient elution. Two purified compounds were isolated as a result. The chemical structures of each compound were determined and identified using $^1H$-NMR and $^{13}C$-NMR, FAB-Mass. The compounds were confirmed as (+)-gallocatechin and prodelphinidin B-3. The tyrosinase inhibitory activities of purified (+)-gallocatechin and prodelphinidin B-3 were 29.5 and 40.2%, respectively. The inhibitory activities of (+)-gallocatechin and prodelphinidin B-3 against melanin biosynthesis in melanoma cell were 32.5 and 46.7%. The safety of essence with tyrosinase inhibitory compounds from persimmon leaves was also assessed by various safety profiles. First, changes in pH (4.90~4.95) and viscosity (23,000~26,000 cP) was not detected for 60 days. Essence also showed stability against temperature and light for 60 days. All these findings suggest that extracts from persimmon leaves have a great potential as a cosmetical ingredient with a potent whitening effect.

Enzymatic Synthesis of Novel $\alpha$-Amylase Inhibitors via Transglycosylation by Thermotoga maritima Glucosidase

  • Kim, Sung-Hee;Lee, Myoung-Hee;Yang, Sung-Jae;Kim, Jung-Woo;Cha, Hyun-Ju;Cha, Jae-Ho;Nguyen, Van Dao;Park, Kwan-Hwa
    • Food Science and Biotechnology
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    • v.17 no.2
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    • pp.302-307
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    • 2008
  • Novel amylase inhibitors were synthesized via transglycosylation by Thermotoga maritima glucosidase (TMG). TMG hydrolyzes acarbose, acarviosine-glucose, and maltooligosaccharide by releasing $^{14}C$-labeled glucose from the reducing end of each molecule. When TMG was incubated with acarviosine-glucose (the donor) and glucose (the acceptor), two major transfer products, compounds 1 and 2, were formed via transglycosylation. The structures of the transfer products were determined using thin-layer chromatography (TLC), high-performance ion chromatography (HPIC), and $^{13}C$ nuclear magnetic resonance (NMR) spectroscopy. The results indicate that acarviosine was transferred to glucose at either C-6, to give a $\alpha-(1{\rightarrow}6$) glycosidic linkage, or at C-3, to produce an $\alpha-(1{\rightarrow}3$) glycosidic linkage. The transfer products showed a mixed-type inhibition against porcine pancreatic $\alpha$-amylase; therefore, they may be useful not only as inhibitors but also as acarbose transition-state analogs to study the mechanism of amylase inhibition.

곰팡이 분리주 MT60109가 생산하는 Phospholipase C 저해물질의 분리

  • Oh, Won-Keun;Lee, Hyun-Sun;Park, Chan-Sun;Ahn, Soon-Cheol;Ko, Hack-Ryong;Mheen, Tae-Ick;Ahn, Jong-Seog
    • Microbiology and Biotechnology Letters
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    • v.25 no.6
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    • pp.592-597
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    • 1997
  • During the screening of inhibitors against phospholipase C (PLC) and the formation of inositol phosphates (IP$_{t}$) at NIH3T3${\gamma}$1 cells from microbial secondary metabolites, we selected a fungal strain MT60109 which was capable of producing an inhibitor. By the taxonomic studies, this fungus was identified as Pseudallescheria sp. MT60109 and an inhibitor of PLC was purified by BuOH extraction and chromatographic techniques from the culture broth of Pseudallescheria sp. MT60109. The inhibitor was identified as thielavin B by the physico-chemical properties and spectroscopic analysis of UV, FAB-MS, $^{1}$H, $^{13}$C-NMR, $^{1}$H-$^{1}$H COSY and HMBC. Thielavin B showed potent inhibitory activity against PLC purified from bovine brain with an IC$_{50}$ of 20 $\mu$M. And it also inhibited the formation of inositol phosphates in platelet-derived growth factor (PDGF) -stimulated NIH3T3${\gamma}$1 cells with an IC$_{50}$ of 20 $\mu$M.

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Biosynthesis of New Oligosaccharides via Acceptor Reaction using Fructosyloligosaccharide as an Acceptor (Fructosyloligosaccharide를 Acceptor 반응의 기질로 사용한 새로운 올리고당의 생합성)

  • 이찬용;이충환
    • Korean Journal of Microbiology
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    • v.35 no.2
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    • pp.146-152
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    • 1999
  • Acceplor reaction of glucosyltr~ansferase of Streptococcus ,SO~~-~IZLIS with f ~ ~ t o ~ y l o l i g o ~ a ~ ~ h a r i d e ~ was studied for the biosynthesis of novel olgisaccharides. First, bacilracin resistant mutants were selected by mutagenesis of Streptococcus sobrimis ATCC27351. Among these mutants 4 strains were selected by resistance to bacitracin and increase of glucosyltransferase. Acceptor reaction of maltose was analyzed by TLC and image analysis. There were differences in the specificity of the acceptor reaclion by Ule glucosylumsferase between mother strain (Streptococcus sobrinus ATCC2735) and bacitracin resistant mutants (Streptococcus sobrinus BR24C, Strepfococcus sobrinus CH-5). Molher strain did ilot show an acceptor reaction with fructosyloligosaccharides such as 1-keqtose and nystose. Acceptor reaction products of turailose and 1-kestose with glucosyltransferase (GW-S) of Streptococcus sobrini~s BR24C were TEX>\6^{3}$-$\alpha$-D-glucopyranosyl \3^{2}$-O-$\alpha$-D-fructose (glucose-fructose-glucose) and \6^{4}$-$\alpha$-D-glucopyranosyl \1^{3}$-$\beta$-D-~-h~ctofuranos~~ sucrose (glucose-glucosefructose- fructose). respectively These are novel oligosaccharides which can be produced only by enzymatic reaction.

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Optimal Culture Conditions for Penicillium rubefaciens NNIBRFG5039 Possessing Antimicrobial Activity (항균활성 보유 Penicillium rubefaciens NNIBRFG5039의 최적배양 조건)

  • Hwang, Hye Jin;Mun, Hye Yeon;Hwang, Buyng Su;Nam, Young Ho;Chung, Eu Jin
    • The Korean Journal of Mycology
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    • v.48 no.1
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    • pp.15-27
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    • 2020
  • In screening for antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) KCCM 40510 and Bacillus cereus KCTC 3624, NNIBRFG5039 was isolated from the air in Sangju-si, Gyeongsangbuk-do. Based on a high sequence similarity of the internal transcribed spacer (ITS) region, NNIBRFG5039 was determined to be closely related to Penicillium rubefaciens CBS 139145. The optimal media, initial pH, and temperature for mycelial growth and antimicrobial activity of P. rubefaciens NNIBRFG5039 were determined as follows: potato dextrose broth (PDB), pH 6.5, and 30℃, respectively. Under the optimal culture conditions, maximum mycelial growth (12.4 g L-1) and antibacterial activity (7.5 mm zone of inhibition against MRSA KCCM 40510, and 5.0 mm zone of inhibition against B. cereus KCTC 3624) were observed in a 5 L stirred-tank fermenter. We also isolated the antimicrobial compound from an ethyl acetate fraction, and its chemical structure was identified as (S)-6-hydroxymellein (1) by ESI-MS, 1H-NMR, and 13C-NMR. Consequently, the extract from P. rubefaciens NNIBRFG5039 may be used in functional materials for antimicrobial-related applications.

Isolation and Identification Antifungal Compounds from Vitex trifolia L. (만형자(Vitex trifolia L.)로부터 항균활성물질의 분리 및 구조결정)

  • Park, Young-Sik;Hwang, Joo-Tae;Kim, Young-Shin;Kim, Jin-Cheol;Lim, Chi-Hwan
    • The Korean Journal of Pesticide Science
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    • v.16 no.4
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    • pp.267-272
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    • 2012
  • Vitex trifolia L. is a full grown fruit of Vitex rotundifolia L. (Verbenaceae). It has been used for treating headache, dizziness, toothache and removal of fever as a traditional medicine in Korea. V. trifolia (500 g) were extracted three times with 80% aqueous MeOH at room temperature. The MeOH extract (38 g) was successively partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$. Both n-hexane and EtOAc fractions showed more than 80% antifungal activity in vivo against several plant pathogens at 2000 ppm. Successive repeated silica gel, Sephadex LH-20, preparative TLC, and preparative HPLC of these fractions led to isolation of three compounds. Using mainly mass spectroscopy and nuclear magnatic resonance (NMR) spectroscopy, their chemical structures were determined as agnuside(1), chrysosplenol B(2), and artemetin(3). Compound 2 was isolated for the first time from V. trifolia. Study on in vitro and in vivo antifungal activities of the isolated compounds is in progress.