• Title/Summary/Keyword: 2-D NMR

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Analysis of Sugar Chain Structure of PAS-7 Glycoprotein from Bovine Milk Fat Globule Membrane by US RAAM 2000 (OGS RAAM2000을 이용한 유지방구막 PAS-7 당단백질의 당쇄구조 해석)

  • 석진석
    • Food Science of Animal Resources
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    • v.21 no.4
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    • pp.367-373
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    • 2001
  • Glycoproteins PAS-6(50 kDa) and -7(47 kDa) from the bovine milk fat globule membrane share a common protein core but differ in their carbohydrate moiety. We have analyzed and proposed the structures of the N-linked sugar chains of PAS-7 by Oxford Glyco System(OGS) RAAM2000. The N-linked sugar chains were liberated from PAS-7 by hydrazinolysis and, after modifying the reducing ends with 2-aminobenzamide(2-AB), were separated into one neutral(7N, 55%) and two acidic(7M, mono-, 43%; 7D, di-, 2%) sugar chain groups. 7N was finally separated into 5 chains(a, b, c, d, and e), respectively. The structure of this 2AB-neutral sugar chain was determined by sugar analysis, exoglycosidase digestion with OGS glycosidase Kit and OGS RAAM2000 system. The results show that fraction e was the same of reported 7N1A, the biantennary complex type with a fucose on reducing end and two N-acetyllactosamine branch on non-reducing end. Therefore, it was proved that OGS RAAM2000 method is in conformity with conventional analysis of sugar chain structure from bovine PAS-7.

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Di- and Sesqui-Terpenoids Isolated from the Pods of Sindora sumatrana and Their Potential to Inhibit Lipopolysaccharide-Induced Nitric Oxide Production

  • Jang, Dae-Sik;Min, Hye-Young;Jeong, Yeon-Hee;Lee, Sang-Kook;Seo, Eun-Kyoung
    • Archives of Pharmacal Research
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    • v.27 no.3
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    • pp.291-294
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    • 2004
  • Activity-guided fractionation of the n-hexane and ${CHCl_3}-soluble$ fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, $(+)-7{\beta}-acetoxy-15,16-epoxy-3$, 13(16), 14-clero-datriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3, 13-clerodadiene-16,15-olide-18-oic acid (3), $(+)-7{\beta}-acetoxy-3$,13-clerodadiene-16,15-olide-18-oic acid (4), $(+)-7{\beta}-acetoxy-16-hydroxy-3$,13-clerodadiene-16, 15-olide-18-oic acid (5), ${\beta}-caryophyllene$ oxide (6), $clovane-2{\beta},9{\beta}-diol (7),{\;}and{\;}caryolane-1,9{\beta}-diol$ (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with $IC_{50}$/ value of $51.6{\;}\mu\textrm{m}M$.

Sesquiterpene Glycosides from the whole Plant Extract of Youngia japonica (뽀리뱅이 전초로부터 분리한 Sesquiterpene 배당체)

  • Kim, Mi-Ri;Cha, Mi-Ran;Choi, Yeon-Hee;Choi, Chun-Whan;Choi, Sang-Un;Kim, Young-Sup;Kim, Young-Kyoon;Kim, Young-Ho;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.41 no.2
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    • pp.103-107
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    • 2010
  • Extensive phytochemical investigation of the methanol extract from the whole plant of Youngia japonica (Asteraceae) led us to the isolation of a new guaiane-type sesquiterpene (1), together with three related guaianolides, youngiajaponicoside A (2), crepiside H (3) and crepeside E (4). The chemical structure of 1 was elucidated by the aid of spectroscopic analyses including 2D-NMR experiments (COSY, HMBC, HMQC and ROESY). The isolated components (1-4) were evaluated for the inhibitory effect on the proliferation of four cultured human tumor cell lines such as A549, SK-OV-3, SK-MEL-2 and HCT-15, in vitro.

Phytochemical and biological investigations of Polygonum lanatum

  • Chowdhury, Sadia A.;Sohrab, Mohammad H.;Haque, Mohammad R.;Hasan, Choudhury M.;Rashid, Mohammad A.
    • Advances in Traditional Medicine
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    • v.8 no.1
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    • pp.97-102
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    • 2008
  • A total of five compounds namely, 2-methylanthracene-9, 10-dione (1), 1-hydroxy-6-methylanthracene-9,10-dione (2), $\beta$-sitosterol (3), stigmasterol (4) and sitosterone (5) were isolated from the stem extracts of Polygonum lanatum for the first time. The structures of the isolated compounds (1-5) were established by extensive spectroscopic studies, including 2D NMR such as $^{1}H-^{1}H$ COSY, HSQC and HMBC studies. The crude extracts and purified compound (1) were screened for antimicrobial activity against a wide range of Gram-positive and Gram-negative bacteria and fungi by the disc diffusion method. The n-hexane and dichloromethane soluble partitionates of the methanolic extract revealed mild to moderate inhibition of growth of the test organisms. The cytotoxic potential of the extractives and compound 1 was also determined by using brine shrimp lethality bioassay, where the extractives demonstrated significant cytotoxic activities.

테트라키스 피콜리나토류 텅그스텐(Ⅳ) 착물의 Inertness에 관한 연구

  • Jang, Ju Hwan;Ronald D. Archer
    • Journal of the Korean Chemical Society
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    • v.34 no.1
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    • pp.85-90
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    • 1990
  • The inertness of eight-coordinate tetrakis(picolinato)tungsten(IV) complex has been investigated by spectroscopic method in nonpolar solvent at 60$^{\circ}C$, 75$^{\circ}C$, 90$^{\circ}C$, 120$^{\circ}C$, and reflux condition. Until 2 days, showed the inertness whether existance of oxygen or not. After 2 days, showed the oxidation of W(IV) complex much more rapidly than substitution, which had $k_{obs}(sec^{-1}) {\varpropto} 1/[ligand]^2$. On sealing the sample under Ar gas, showed the inertness until 50 days, which had $k_{obs}(sec^{-1}) = 8.8{\times} 10^{-7}$. The$^1H$-NMR peak of $H_6$ in complex was diminished, otherwise that of free ligand was grown up. This result indicated that this complex was very inert.

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Biochemical Studies on the Sugar Chain Structure of Glycoproteins with the Same Protein Core of Bovine Milk Fat Globule Membrane (공통의 1차 구조를 가진 우유 지방구막 구성단백질의 당쇄 구조에 관한 생화학적 연구)

  • Seok, Jin-Seok
    • Journal of Dairy Science and Biotechnology
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    • v.21 no.2
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    • pp.138-147
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    • 2003
  • We here analyzed and proposed the structures of the N-linked sugar chains of PAS-7 from bovine milk fat globule membrane. The N-linked sugar chains were liberated from PAS-7 by hydrazinolysis and, after modifying the reducing ends with 2-aminopyridine (PA), were separated into one neutral (7N,55%) and two acidic (7M mono-, 43%; 7D, di-, 2%) sugar chain roups. The latter were converted into neutral groups (7MN and 7DN) by sialidase digestion. The structure of each of these PA-neutral sugar chains was determined by sugar analysis, sequential exoglycosidase digestion, partial acetolysis, and 1H-NMR spectroscopy. The results show that the 10 sugar chains were of the biantennary complex type with and without fucose. The structure of 7N2A one of the major sugar chains, was proposed as; [structure: see text] A structural comparison between PAS-6 and -7 indicated that although they shared the same protein core, their sugar moiety was markedly different, involving the existence of a different pathway during the post-transcriptional modification.

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Isolation of Daucosterol and Naphthalene glucoside from Seeds of Cassia mimosoides var. nomame Makino (차풀 종자로부터 Daucosterol과 Naphthalene glucoside의 분리)

  • Park, Jun-Hong;Kwon, Sun-Jin
    • Korean Journal of Plant Resources
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    • v.22 no.1
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    • pp.26-30
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    • 2009
  • Daucosterol and naphthalene glycoside were isolated from the seeds of Cassia mimosoides var. nomame Makino. The isolated compounds were identified by spectral means including 1D, 2D-NMR and FAB-MS experiments. Daucosterol was characterized as ${\beta}$-sitosterol-3-O-${\beta}$-D-glucoside and naphthalene glucoside was done as 2-acetyl-3-methyl-6-methoxynaphthalene-1,8-diol 8-O-glucosyl-(1${\rightarrow}$6)-glucoside. These compounds were isolated for the first time from Cassia mimosoides var. nomame Makino.

Antimicrobial Properties and Cytotoxicity of Sulfated (1,3)-β-D-Glucan from the Mycelium of the Mushroom Ganoderma lucidum

  • Wan-Mohtar, Wan Abd Al Qadr Imad;Young, Louise;Abbott, Grainne M.;Clements, Carol;Harvey, Linda M.;McNeil, Brian
    • Journal of Microbiology and Biotechnology
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    • v.26 no.6
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    • pp.999-1010
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    • 2016
  • Ganoderma lucidum BCCM 31549 has a long established role for its therapeutic activities. In this context, much interest has focused on the possible functions of the (1,3)-β-D-glucan (G) produced by these cultures in a stirred-tank bioreactor and extracted from their underutilized mycelium. In the existing study, we report on the systematic production of G, and its sulfated derivative (GS). The aim of this study was to investigate G and its GS from G. lucidum in terms of their antibacterial properties and cytotoxicity spectrum against human prostate cells (PN2TA) and human caucasian histiocytic lymphoma cells (U937). 1H NMR for both G and GS compounds showed β-glycosidic linkages and structural similarities when compared with two standards (laminarin and fucoidan). The existence of characteristic absorptions at 1,170 and 867 cm-1 in the FTIR (Fourier Transform Infrared Spectroscopy) for GS demonstrated the successful sulfation of G. Only GS exhibited antimicrobial activity against a varied range of test bacteria of relevance to foodstuffs and human health. Moreover, both G and GS did not show any cytotoxic effects on PN2TA cells, thus helping demonstrate the safety of these polymers. Moreover, GS showed 40% antiproliferation against cancerous U937 cells at the low concentration (60 μg/ ml) applied in this study compared with G (10%). Together, this demonstrates that sulfation clearly improved the solubility and therapeutic activities of G. The water-soluble GS demonstrates the potential multifunctional effects of these materials in foodstuffs.

Isoflavanones from the Stem of Cassia siamea and Their Anti-tobacco Mosaic Virus Activities

  • Hu, Qiu-Fen;Niu, De-Yun;Zhou, Bin;Ye, Yan-Qing;Du, Gang;Meng, Chun-Yang;Gao, Xue-Mei
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.3013-3016
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    • 2013
  • Two new isoflavanones, (3R) 7,2',4'-trihydroxy-3'-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R) 7,2'-dihydroxy-3',4'-dimethoxy-5-methoxycarbonyl-isoflavanone (2), together with six known isoflavanones (3-8), were isolated from the stems of Cassia siamea. The structure of 1-8 was elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1, 2, 5-8 were evaluated for their anti-tobacco mosaic virus (Anti-TMV) activity. The results showed that compounds 1 and 6 showed potential anti-TMV activity with inhibition rates of 24.6% and 26.9%, respectively. Compounds 2, 5, 7, 8 also showed anti-TMV activity with inhibition rates in the range of 11.8-18.6%.

Efficient Purification and Chemical Structure ldentification of Carthamin from Carthamus tinctorius (홍화적색소 Carthamin의 효과적인 분리 및 화학구조 분석)

  • Kim, Jun-Beom;Cho, Man-Ho;Hahn, Tae-Ryong;Paik, Young-Sook
    • Applied Biological Chemistry
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    • v.39 no.6
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    • pp.501-505
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    • 1996
  • 우리나라에서 오랫동안 적색 및 황색색소원으로 널리 사용하여 왔던 홍화(Carthamus tinctorius)로부터 전통적인 추출방법을 응용한 새로운 방법을 사용하여 적색소를 효과적으로 분리정제하였다. 홍화꽃잎을 물 및 메탄올로 처리하여 황색소를 제거한 다음 건조파쇄하여 0.5 M $Na_2CO_3$로 홍색소를 추출하고 0.5 M citrate 수용액으로 침전시킨 후 cellulose 흡착, Sephadex LH-20 관크로마토그라피로 분리정제하였다. 분리정제된 적색소는 $300^{\circ}C$에서 분해되었고 silica gel TLC 상에서 BAW(n-BuOH : HOAc : $H_2O$=4 : 1 : 5)로 전개하였을 때 $R_f$값이 0.56이었다. 에탄올 용액에 녹인 적색소의 UV/Vis 흡수스펙트럼은 519, 372, 311, 244 nm에서 최대 흡수피크를 나타내었고, IR 스펙트럼은 특히 $3400\;cm^1$ 넓은 영역에서 hydroxyl기에 의한 강한 흡수띠를 보여주었다. $^{1}H$$^{13}C$ NMR data로 부터 enolized ${\beta}-triketone$, p-hydroxycinnamoyl, methine 및 glucosyl moieties를 확인하였고 그 값을 제시하였다. 이상의 data를 문헌과 비교한 결과 분리한 홍화적색소의 화학구조는 $6-{\beta}-D-glucopyranosyl-2-[[3-{\beta}-D-glucopyranosyl-2,3,4-trihydroxy-5-[3#-(4@-hydroxyphenyl)-1#-oxo-2#-propenyl]-6-oxo-1,4-cyclohexadien-1-yl]methylene]-5,6-dihydroxy-4-[3#-(4@-hydroxyphenyl)-1#-oxo-2#-propenyl]-4-cyclohexene-1,3-dione$인 carthamin으로 확인하였다.

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