• 제목/요약/키워드: pyrone

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Advances in the Field of Thermal Procedures in Direct Combination with Thin-layer Chromatography

  • Stahl, Egon
    • 생약학회지
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    • 제7권1호
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    • pp.3-13
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    • 1976
  • The hitherto existing gap in the field of chromatographic methods has been filled by the direct coupling of a suitable oven (TAS-oven) with TLC. The sample to be examined is heated either isothermally or linearly within the temperature gradient of $50{\sim}450^{\circ}C$. The volatile and/or thermolytically evolved substances are fractionated on the TLC-layer and subsequently chromatographed under standard conditions. Transport mechanisms from the sample to the TLC-layer, applications of the TAS-procedure and further developments are discussed. Thermofractography, developed from the TAS-procedure, is demonstrated on different groups of natural substances such as alkaloids, amino acids, nucleic acids. nucleosides, nucleotides, triglycerides and other lipids, pyrone glycosides and aglycon. Experimental work and results on the thermolysis of macromolecular natural and synthetic substances, natural polyphenols, tanning agents and leather and the possibilities of differentiating various lignins, carbohydrate and synthetic polymers are reported. Further, it is shown that classical reactions in the microgram range, e.g. zinc dust distillation, sulphur-and selenium dehydrogenation and catalytic dehydrogenation, can be coupled directly with TLC. Also described is a method which allows to investigate the gaseous compounds evolved during thermofractography in the range of up to $450^{\circ}C$. Thermal procedures coupled with TLC open up the following new possibilities for chemical microanalysis: fractionated separation of distillable and sublimable components, fractionated thermolysis and carrying out of thermal reactions in the ultra micro range.

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Chemical Constituents of Abies koreana Leaves with Inhibitory Activity against Nitric Oxide Production in BV2 Microglia Cells

  • Baek, Sa-Wang;Kim, E. Ray;Kim, Jin-Woong;Kim, Young-Choong
    • Natural Product Sciences
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    • 제17권3호
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    • pp.175-180
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    • 2011
  • Eleven compounds were isolated from fresh leaves of Abies koreana (Pinaceae), and structures of these compounds were determined to be 3-hydroxy-2-methyl-4-pyrone (1), maltol-3-O-${\beta}$-D-glucoside (2), (-)-epicatechin (3), naringenin 7-O-${\beta}$-D-glucopyranoside (4), naringenin-7-O-rhamnoglucoside (5), kaempferol 3-O-${\beta}$-D-glucopyranoside (6), (+)-isolariciresinol (7), secoisolariciresinol (8), rhododendrol (9), ferulic acid (10) and 4-(4-hydroxyphenyl)butan-2-one (rheosmin) (11) by comparing $^1H$-, $^{13}C$-NMR and MS spectroscopic data with reference values. Compounds 3, 5, 7, 8, 9, 10, 11 were isolated for the first time from A. koreana. Among eleven isolates, compounds 1, 7 and 11 showed inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia in a concentration dependent manner.

플라보노이드에 의한 사람 Low Density Lipoprotein 변형에 대한 항산화 효과 (Antioxidative Effects of Flavonoids toward Modification of Human Low Density Lipoprotein)

  • 류병호
    • 한국식품영양학회지
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    • 제12권3호
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    • pp.320-327
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    • 1999
  • The flavonoids are one of the most numberous and widespread groups of natural consituents. The low molecular weight of benzo-${\gamma}$-pyrone derivative are ubiquitous in plants and are vegetables nuts, seeds, leaves, flowers, and bark. The flavonoids constitute of a large class of compounds ubiquitous in plants containing a number of phenolic hydroxyl groups attached to ring structures conferring the antioxidant activity. Epidemiologic studies suggest that the dietary intake of antioxidants constitutes a risk factor for vasclar disease indicating that oxidation may be important in the pathogenesis of human athero-sclerosis. Elevated plasma low density lipoprotein (LDL) cholesterol concentration are associated with accelerated atherosclerosis, LDL is oxidized by smooth muscle cells resulting in several chemicals and physical changes of LDL. Oxidized LDL is responsible for cholesterol loading of macrophages foam cells formation and atherogenesis. There have been insulficient tests of the protective effects of flavonoids against LDL oxidation to make definitive statements about their structure activity relationships. How-ever hydroxylation of the flavone uncleas can appears to be advantageous because polyhydroxylated aglycone flavonoids are potent inhibitor of LDL modification. This identification may lead to new and more effective antioxidant strategies for abrogating the atherosclerotic process the leading cause of death and disability in industrialized societies.

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Development of Novel Pyrone Derivative Retaining Retinoidal Anti-aging Activity with Low Skin Irritation

  • Rho, H.S;Kim, D.H;Kim, S.N;Kim, S.J;Chang, I.S;Kang, H.H;Lee, O.S
    • 대한화장품학회:학술대회논문집
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    • 대한화장품학회 2003년도 IFSCC Conference Proceeding Book II
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    • pp.184-191
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    • 2003
  • New pyranone derivative, 2-((3E)-4(2H, 3H, -benzo[3, 4-d] 1, 3-dioxolan-5-yl)-2-oxo-but-3-enyloxy)-5-hydroxy-4H-pyran-4-one (Seletinoid $G^{TM}$), was designed as a novel retinoid on the assumption that the pyranone ring may mimic the carboxylic acid moiety in retinoid structure. The enolic hydroxy of pyranone at five position was easily deprotonated to form an enolate. The role of enolate was similar to that of carboxylic acid. To evaluate the value of Seletinoid G as an anti-aging ingredient, various tests were performed for example inhibitory effect for MMP-l expression, anti-oxidative activity, procollagen synthesis in hairless mouse and primary skin irritation. The result of this study suggested that our new synthetic retinoid could be used as a safe material for anti-aging cosmetics.

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Crystal and Molecular Structure of 12-(2-Methoxyphenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo [12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carbonitrile

  • Ganapathy, Jagadeesan;Damodharan, Kannan;Manickam, Bakthadoss;Sanmargam, Aravindhan
    • 통합자연과학논문집
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    • 제7권3호
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    • pp.149-158
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    • 2014
  • The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=$8.5775(4){{\AA}$, b=$24.9943(13){\AA}$ and c=$13.7319(7){\AA}$ [alpha & gamma=$90^{\circ}$ beta=$103.558(2)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [$121.08(1)^{\circ}$] and N1-S1-C5 [$105.85(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($354.9^{\circ}$) indicates that N1 is in $sp^2$ hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. Crystal structure is stabilized by C-H...O intra molecular hydrogen bond interactions.

산소중독에 대한 MALTOL의 보호효과에 관한 실험적 연구 (An Experimental Study on the Effect of Maltol against Oxygen Toxicity)

  • 황성주;조수헌;윤덕로
    • Journal of Preventive Medicine and Public Health
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    • 제26권4호
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    • pp.551-564
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    • 1993
  • Since the widespread application of hyperbaric oxygenation in clinical medicine, the problems of oxygen toxicity have been attracting a deep interest from the researchers on hyperbaric medicine as a practical issue. Among extensive research trials, the study on the protective agents oxygen toxicity occupied one of the most challenging field. As the mechanisms of oxygen toxicity, the role of the oxygen free radicals produced by peroxidation process are strongly accepted by the leading researchers on oxygen toxicity, the probable protective effects of antioxidant against oxygen toxicity are sustaining a sufficient rational. Maltol ($2-methyl-3-hydroxy-{\gamma}-pyrone$) which is known to be a component of Korean red ginseng has been reporting to have an antioxidant action. But, further study is needed to provide definite evidence for this compound to be an antioxidant, since the action was based on the results which were obtained under in vitro experiment. In this study, the author attempted to evaluate the effect of maltol as protective agent against oxygen toxicity through the observation of death rate, convulsion rate, time to convulsion and microscopic pathological changes in some organs of experimental rats exposed to various conditions. The findings observed are as follows : 1) The death rate, convulsion rate, time to convulsion, lung/weight ratio and microscopic pathological finding of lung were identified as reliable objective and quantitative indices for oxygen toxicity. 2) Maltol showed excellent protective effect against pulmonary oxygen toxicity as an antioxidant.

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4',5'-디히드로소랄렌과 테트라메틸에틸렌의 광고리화 첨가반응에 관한 연구 (Photocycloaddition Reaction of 4',5'-Dihydropsoralen to Tetramethylethylene)

  • 심상철;고종성
    • 대한화학회지
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    • 제26권3호
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    • pp.172-178
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    • 1982
  • 4',5'-디히드로소랄렌(DHP)을 합성하여 상온 및 77K에서 이 화합물의 형광 양자수율은 0.08, 인광양자수율은 0.013, 형광수명은 0.95ns, 인광수명은 0.039s 임을 알았다. 이 결과로부터 형광수명은 5,7-디메톡시쿠마린보다 작은반면 소랄렌보다 크고 반면 인광수명은 DMC 보다 크고 소랄렌보다 작음을 알았다. 소랄렌 유도체들의 광독성을 분자적 차원에서 규명하고 DNA에의 광부가 반응을 알아내기 위하여 DHP와 TME의 광부가 반응을 연구하였다. 주 생성물은 TLC로 분석하고 Preparative TLC와 용매추출로 분리해냈다. 분리된 생성물의 구조는 질량분석기, UV, IR, NMR 그리고 원소분석결과에 의해 DHP와 TME외 광고리화첨가반응에 의한 생성물 임을 알았다. DHP는 형광의 자체소광 효과를 볼 수 없으며 TME, 에틸푸마레이트, 푸마로니트릴에 의해 형광이 효과적으로 소광된다. 광부가 반응의 양자수율과 소광실험에서 DHP의 광첨가반응은 단일상태와 삼중상태에서 다 일어나는 것으로 추측된다.

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효소분해법에 의한 개량어장유의 속성제조 및 품질에 관한 연구 4. 정어리 전어체를 이용한 어장유의 냄새 성분 (Conditions for Rapid Processing of Modified Fish Sauce using Enzymatic Hydrolysis and Improvement of Product Quality 4. Flavor Components of Fish Sauce from Whole Sardine)

  • 배태진;한봉호;조현덕;김병삼;이현숙
    • 한국수산과학회지
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    • 제23권5호
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    • pp.373-377
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    • 1990
  • Volatile components of whole sardine sauce which was prepared with $7\%$ of complex enzyme-2000($2.18{\cdot}10^4\;U/g solid$), mixed with $6\%$ of invert sugar and heated at $90^{\circ}C$ for 2 hours were compared with those of without invert sugar. Thirty seven kinds were identified from the whole volatile components of hydrolysate heated without invert sugar and fourty three kinds were identified from the hydrolysate heated with $6\%$ of invert sugar. Amines were not detected from the whole volatile components of the chopped whole sardine hydrolysate. Considerable amount of 2,3-dihydrobenzofuran and 2-acetylpyrrole, a little amount of 2,5-hydrofuran, 2-ethylbutanol, 2-pyrone, 2-acetylfuran, 2,6-dimethylpyrazine, 2-acetylpyrazine, 5-methyl-2-furfural, furfuryl acetate, butylpyrrole and 2-methyl-3-hydroxypyrone were detected in the hydrolysate thermally treated with $6\%$ of invert sugar while these were not found in the hydrolysate heated without invert sugar. But the amount of 2-methyt-1-propa-not, hexane, butyl acetate and butyl alcohol were decreased, and acetic acid and butanoic acid were detected as volatile fatty acids.

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Crystal and Molecular Structure of Methyl 12-(3-bromophenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carboxylate

  • Kothandan, Gugan;Ganapathy, Jagadeesan;Damodharan, Kannan;Sanmargam, Aravindhan
    • 통합자연과학논문집
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    • 제7권2호
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    • pp.92-102
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    • 2014
  • The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a = 28.633(3) ${\AA}$, b= 9.3215(7) ${\AA}$ and c= 24.590(2) ${\AA}$ [alpha & gamma=$90^{\circ}$ beta= $115.976(3)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [119.74 $(2)^{\circ}$] and N1-S1-C5 [$105.57(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($316.2(1)^{\circ}$) indicates that N1 is in sp2 hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. The carboxylate group of atoms were disordered over two positions with site occupancy factors 0.598 (9):0.402 (9). Crystal structure and packing is stabilized by $C-H{\ldots}O$ intra and inter molecular hydrogen bond interactions.

Optimization of Agrobacterium tumefaciens-Mediated Transformation of Xylaria grammica EL000614, an Endolichenic Fungus Producing Grammicin

  • Jeong, Min-Hye;Kim, Jung A.;Kang, Seogchan;Choi, Eu Ddeum;Kim, Youngmin;Lee, Yerim;Jeon, Mi Jin;Yu, Nan Hee;Park, Ae Ran;Kim, Jin-Cheol;Kim, Soonok;Park, Sook-Young
    • Mycobiology
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    • 제49권5호
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    • pp.491-497
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    • 2021
  • An endolichenic fungus Xylaria grammica EL000614 produces grammicin, a potent nematicidal pyrone derivative that can serve as a new control option for root-knot nematodes. We optimized an Agrobacterium tumefaciens-mediated transformation (ATMT) protocol for X. grammica to support genetic studies. Transformants were successfully generated after co-cultivation of homogenized young mycelia of X. grammica with A. tumefaciens strain AGL-1 carrying a binary vector that contains the bacterial hygromycin B phosphotransferase (hph) gene and the eGFP gene in T-DNA. The resulting transformants were mitotically stable, and PCR analysis showed the integratin of both genes in the genome of transformants. Expression of eGFP was confirmed via fluorescence microscopy. Southern analysis showed that 131 (78.9%) out of 166 transformants contained a single T-DNA insertion. Crucial factors for producing predominantly single T-DNA transformants include 48 h of co-cultivation, pretreatment of A. tumefaciens cells with acetosyringone before co-cultivation, and using freshly prepared mycelia. The established ATMT protocol offers an efficient tool for random insertional mutagenesis and gene transfer in studying the biology and ecology of X. grammica.