• 제목/요약/키워드: 2H-benzopyran

검색결과 43건 처리시간 0.022초

Deuterium-labeling Toward Robust Function of Organic Molecules: Enhanced Photo-stability of Partially Deuterated 1', 3', 3'-Trimethyl-6-nitrospiro[2H-1- benzopyran-2, 2'-indoline]

  • Kawanishi, Yuji;Inoue, Kyoko;Ohta, Shin-Ichi;Miyazawa, Akira
    • Rapid Communication in Photoscience
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    • 제3권4호
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    • pp.64-66
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    • 2014
  • Synthesis of a deuterium-labeled derivative of nitrospirobenzopyran (NSP), one of representative photochromic compounds, has been described. Four deuteriums were successfully introduced on 1-methyl and ${\alpha}$-methyne relative to spiro-carbon in the title compound with more than 95atom%D purity. Main photodegraded products of NSP were two oxindoles in acetonitrile, and additional products were formed in poly(isobutyl-methacrylate) films possibly due to restricted molecular motion in polymer matrix. Quantitative HPLC analysis revealed that partial introduction of deuterium to NSP brought a noticeable isotope effect, recognizable enhancement in photo-resistivity of NSP, i.e.,8.3% in solutions and 29% in polymeric films.

Chemical Constituents of the Fruiting Body of Xylaria polymorpha

  • Jang, Yun-Woo;Lee, In-Kyoung;Kim, Young-Sook;Seok, Soon-Ja;Yu, Seung-Hun;Yun, Bong-Sik
    • Mycobiology
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    • 제37권3호
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    • pp.207-210
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    • 2009
  • Xylaria, belonging to the Ascomycotina, is known to produce diverse classes of bioactive substances. In an effort to identify the chemical constituents of the fruiting bodies of Xylaria polymorpha, linoleic acid (1), linoleic acid methyl ester (2), ergosterol (3), 4-acetyl-3,4-dihydro-6,8-dihydroxy-3-methoxy-5-methyl-1H-2-benzopyran-1-one (4), and 4-hydroxyscytalone (5) were isolated from its methanolic extract. Their structures were assigned on the basis of various spectroscopic studies.

박하(Mentha arvensis) 향료의 향기성분이 정신적 스트레스 완화에 미치는 효과 (Fragrance Chemicals in the Essential Oil of Mentha arvensis Reduce Levels of Mental Stress)

  • 조해미;칸다사미 손하라라잔;정지욱;주진우;김성문
    • 생명과학회지
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    • 제23권7호
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    • pp.933-940
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    • 2013
  • 본 연구는 박하(Mentha arvensis) 식물 유래 향료의 향기성분을 구명하고, 향기성분들이 인간의 뇌파에 어떠한 영향을 미치는지를 이해하고자 수행하였다. 초임계추출기를 이용하여 박하 식물(Mentha arvensis L. f. piperascens)로부터 에센셜오일을 얻었으며, 최적 회수율은 $70^{\circ}C$, 200 bar 조건에서 2.38%이었다. 박하 에센셜오일에 함유되어 있는 향기 화합물을HS-SPME/GC-MS로 분석한 결과, 총 32종의 화합물이 검출되었는데 alcohol 류가 6종(67.11%), hydrocarbon 류가 13종(17.05%), ester 류가 9종(11.50%), ketone 류가 2종(7.16%), oxide가 1종(2.77%) 그리고 aldehyde가 1종(0.56%)이었다. 박하 에센셜오일에 함유된 주된 향기 화합물은 (Z,Z,Z)-9,12,15-octadecatrien-1-ol (50.06%), 2-hydroxy-4-methoxyacetophenone (7.50%)과 3,4-dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one (6.60%) 이었다. 총 20명의 피험자(남녀 각 10명)를 대상으로 박하 에센셜오일 향기 흡입 전과 흡입 중에 뇌파분석을 수행한 결과, 향기를 흡입 중에는, 흡입 전과 비교하여, relative fast alpha power spectrum이 유의성 있게 증가하는 반면(p<0.05), gamma power spectrum과 spectral edge frequency 90% 지표는 유의성 있게 감소하는 결과를 얻었다(p<0.05). 본 연구의 결과들은 박하의 향기성분이 정신적 긴장을 완화시킨다는 것을 시사하여 준다.

옻나무류의 항산화력 및 항산화 효소 활성 (Evaluation of the antioxidant potential and enzyme activities in species of Rhus)

  • 정형진;김은희;이건주;정규영;임종국;유정민;심영은;박재호
    • 한국자원식물학회지
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    • 제14권3호
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    • pp.220-228
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    • 2001
  • 한국에서 자라고 있는 옻나무속 3종의 항산화력을 조사하여 본 결과, 옻나무속 3종의 각 부위별 ethyl acetate 추출물에 대한 항산화능은 개옻나무의 경우 잎과 줄기에서 각각 32, 34 $\mu\textrm{g}$/$m\ell$, 옻나무의 경우 잎과 줄기에서 각각 39,21 $\mu\textrm{g}$/$m\ell$의 활성을 나타내었다. Sephadex LH-20 column chromatography를 이용하여 줄기 부위의 추출물을 12개의 fraction으로 분리하여 항산화능을 측정한 결과, fraction No.3이 가장 높은 항산화 활성을 나타내었으며, 옻나무가 1.5, 붉나무가 1.9, 개옻나무가 2.3 ug/$m\ell$ DPPH가를 나타내었다. 줄기 추출물로부터 2-propenoic acid (Caffeic acid), Benzoic acid (Gallic acid), 7-hydroxy-6- methoxy-2H-1-Benzopyran-2-one (Scopoletin) 등과 같은 phenol계 물질들이 동정되었다. 옻나무속 3종의 부위별 POD 활성 은 잎에 비해 줄기에서 193배 활성이 높게 나타났고 종간에는 붉나무가 0.58 unit/mg protein로 가장 높게 나타났으며 옻나무, 개옻나무 순으로 높게 나타났다. SOD 활성은 옻나무와 붉나무의 잎에 비해 줄기에서 높은 활성이 나타났으나,개옻나무는 잎이 줄기에 비해 25배 높게 나타났다.

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Antimicrobial Activities of (-)Epicatechin from Ulmus davidiana var. japonica Cortex

  • Lee, Gyu-Hee;Shim, Chang-Ju;Chang, Yeong-Il;Park, Seong-Hyun;Oh, Hong-Rock;Oh, Man-Jin
    • Preventive Nutrition and Food Science
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    • 제6권4호
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    • pp.230-234
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    • 2001
  • The extract of Ulmus davidiana var. japonica cortex has known as natural anti-inflammatory substance in East Asia. For the identification of antimicrobial substance, it was extracted by using methanol and fractionated by using different organic solvents. The fraction of butanol was represented the highest antimicrobial activities. Therefore, the butanol fraction was purified and identified the chemical structure by $^1$H and $^{13}$ C-NMR spectra, FT-IR and EI/MS spectroscopies. The isolated antimicrobial substance was identified as cis-2-[3,4-dihydroxy phenyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol, which has commonly known as (-)epicatechin. Its minimum inhibitory concentrations (MICs) against Staphylococcus aureus and Listeria monocytogenes were shown as 100 $\mu\textrm{g}$/mL, respectively.

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Protective Effect of KR-31378 on Oxidative Stress in Cardiac Myocytes

  • Kim Mi-Young;Lee Sunkyung;Yi Kyu Yang;Yoo Sung Eun;Lee Dong-Ha;Lim Hong;Kim Ho Soon;Lee Soo Hwan;Baik Eun Joo;Moon Chang-Hyun;Jung Yi-Sook
    • Archives of Pharmacal Research
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    • 제28권12호
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    • pp.1358-1364
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    • 2005
  • In this study, we investigated whether a novel anti-ischemic $K_{ATP}$ opener KR-31378 [(2S,3S,4R)­N'-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2 -methly-2-dimethoxymethly-2H-benzopyran-4-yl)­N'-benzylguanidine] has protective effect against oxidative stress-induced death in heart-derived H9c2 cells. Cell death was induced by BSO, butionine sulfoximine, which inhibits GSH synthesis and subsequently increases reactive oxygen species (ROS) level. Cell death was quantitatively determined by measuring lactate dehydrogenase (LDH) activity and stained by Hoechst 33258. BSO-induced ROS production and mitochondrial membrane potential (MMP) were measured using 2',7'-dichlorofluorescein diacetate oxidation and rhodamine 123, respectively. Both the LDH release and the ROS elevation induced by treatment of H9c2 cells with 10 mM BSO, were significantly decreased by KR-31378. These protective effect and antioxidant effect of KR-31378 appeared to be independent on $K_{ATP}$ channel opening. Cells exposed to BSO showed an early reduction in MMP, and this reduction in MMP was significantly reversed by treatment with KR-31378. Caspase-3 activity in BSO treated H9c2 cells was remarkably increased, and this increased caspase-3 activity was significantly reversed by KR-31378. In conclusion, our results suggest that KR-31378 can produce cardioprotective effect against oxidative stress-induced cell death through antioxidant mechanism.

In Vitro Metabolism of a New Neuroprotective Agent, KR-31543 in the Human Liver Microsomes : Identification of Human Cytochrome P450

  • Ji, Hye-Young;Lee, Seung-Seok;Yoo, Sung-Eun;Kim, Hosoon;Lee, Dong-Ha;Lim, Hong;Lee, Hye-Suk
    • Archives of Pharmacal Research
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    • 제27권2호
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    • pp.239-245
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    • 2004
  • KR-31543, (2S,3R,4S)-6-amino-4-[N-(4-chlorophenyl)-N-(2 -methyl-2H-tetrazol-5-ylmethyl) amino]-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-1-benzopyran, is a new neuroprotective agent for preventing ischemia-reperfusion damage. This study was performed to identify the metabolic pathway of KR-31543 in human liver microsomes and to characterize cytochrome P450 (CYP) enzymes that are involved in the metabolism of KR-31543. Human liver microsomal incubation of KR-31543 in the presence of NADPH resulted in the formation of two metabolites, M1 and M2. M1 was identified as N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amine on the basis of LC/MS/MS analysis with a synthesized authentic standard, and M2 was suggested to be hydroxy-KR-31543. Correlation analysis between the known CYP enzyme activities and the rates of the formation of M 1 and M2 in the 12 human liver microsomes have showed significant correlations with testosterone 6$\beta$-hydroxylase activity (a marker of CYP3A4). Ketoconazole, a selective inhibitor of CYP3A4, and anti-CYP3A4 monoclonal antibodies potently inhibited both N-hydrolysis and hydroxylation of KR-31543 in human liver microsomes. These results provide evidence that CYP3A4 is the major isozyme responsible for the metabolism of KR-31543 to M1 and M2.

Characterization of Forest Fire Emissions and Their Possible Toxicological Impacts on Human Health

  • Kibet, Joshua;Bosire, Josephate;Kinyanjui, Thomas;Lang'at, Moses;Rono, Nicholas
    • Journal of Forest and Environmental Science
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    • 제33권2호
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    • pp.113-121
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    • 2017
  • In flight particulate matter particularly emissions generated by incomplete combustion processes has become a subject of global concern due to the health problems and environmental impacts associated with them. This has compelled most countries to set standards for coarse and fine particles due to their conspicuous impacts on environment and public health. This contribution therefore explores forest fire emissions and how its particulates affects air quality, damage to vegetation, water bodies and biological functions as architects for lung diseases and other degenerative illnesses such as oxidative stress and aging. Soot was collected from simulated forest fire using a clean glass surface and carefully transferred into amber vials for analysis. Volatile components of soot were collected over 10 mL dichloromethane and analyzed using a QTOF Premier-Water Corp Liquid Chromatography hyphenated to a mass selective detector (MSD), and Gas Chromatograph coupled to a mass spectrometer (GC-MS). To characterize the size and surface morphology of soot, a scanning electron microscope (SEM) was used. The characterization of molecular volatiles from simulated forest fire emissions revealed long chain compounds including octadec-9-enoic acid, octadec-6-enoic acid, cyclotetracosane, cyclotetradecane, and a few aromatic hydrocarbons (benzene and naphthalene). Special classes of organics (dibenzo-p-dioxin and 2H-benzopyran) were also detected as minor products. Dibenzo-p-dioxin for instance in chlorinated form is one of the deadliest environmental organic toxins. The average particulate size of emissions using SEM was found to be $11.51{\pm}4.91{\mu}m$. This study has shown that most of the emissions from simulated forest fire fall within $PM_{10}$ particulate size. The molecular by-products of forest fire and particulate emissions may be toxic to both human and natural ecosystems, and are possible precursors for various respiratory ailments and cancers. The burning of a forest by natural disasters or man-made fires results in the destruction of natural habitats and serious air pollution.

제제헝태에 따른 이프리플라본의 생체이용률 비교 (Comparative Bioavailability of Ipriflavone by Pharmaceutical Preparation Types)

  • 정제교;강길선;이종문;신호철;이해방
    • Journal of Pharmaceutical Investigation
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    • 제30권1호
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    • pp.21-26
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    • 2000
  • Bioavailability of ipriflavone (3-phenyl-7-isopropoxy-4H-I-benzopyran-4-one, IP), an antiosteoporotic drug with poor water-solubility, was studied for various types of pharmaceutical preparation in SD rats. The IP preparation types included (1) intact IP, (2) freezer milled IP (FIP), (3) freezer milled IP physically mixed with freezer milled poly-N-vinylpyrrolidone (PVP) (FIP+FPVP) and (4) spray-dried IP with PVP (SIP). Upon oral administration, SIP showed significantly higher absorption and elimination half-lives and the lag time $(t_{lag})$ than those of FIP+FPVP (approximately 2-fold). These results may be due to a sustained releasing effect of IP in the gastrointestinal tract by spray-drying with PVP. The $C_{max}$ of SIP was about 2 and 10 times higher than those of FIP+FPVP and FIP, respectively. The AUC of SIP was about 6 times higher than that of FIP+FPVP and 60 times that of FIP. Scanning electron microscopy (SEM) showed that SIP consisted of the finest particle size and minimal aggregation than other IP preparations. It is concluded that the IP formula prepared by the spray-drying method with PVP is the most effective approach to the improvement of bioavailability of IP.

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Neuroprotective Effect of Visnagin on Kainic Acid-induced Neuronal Cell Death in the Mice Hippocampus

  • Kwon, Min-Soo;Lee, Jin-Koo;Park, Soo-Hyun;Sim, Yun-Beom;Jung, Jun-Sub;Won, Moo-Ho;Kim, Seon-Mi;Suh, Hong-Won
    • The Korean Journal of Physiology and Pharmacology
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    • 제14권5호
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    • pp.257-263
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    • 2010
  • Visnagin (4-methoxy-7-methyl-5H-furo[3,2-g][1]-benzopyran-5-one), which is an active principle extracted from the fruits of Ammi visnaga, has been used as a treatment for low blood-pressure and blocked blood vessel contraction by inhibition of calcium influx into blood cells. However, the neuroprotective effect of visnagin was not clearly known until now. Thus, we investigated whether visnagin has a neuroprotective effect against kainic acid (KA)-induced neuronal cell death. In the cresyl violet staining, pre-treatment or post-treatment visnagin (100 mg/kg, p.o. or i.p.) showed a neuroprotective effect on KA ($0.1{\mu}g$) toxicity. KA-induced gliosis and proinflammatory marker (IL-$1{\beta}$, TNF-${\alpha}$, IL-6, and COX-2) inductions were also suppressed by visnagin administration. These results suggest that visnagin has a neuroprotective effect in terms of suppressing KA-induced pathogenesis in the brain, and that these neuroprotective effects are associated with its anti-inflammatory effects.