• Title/Summary/Keyword: 2H-benzopyran

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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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    • v.3 no.4
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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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    • v.37 no.3
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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.

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

  • Cho, Haeme;Sowndhararajan, Kandhasamy;Jung, Ji-Wook;Jhoo, Jin-Woo;Kim, Songmun
    • Journal of Life Science
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    • v.23 no.7
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    • pp.933-940
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    • 2013
  • The aim of this work was to determine the chemical composition of essential oil from aerial partsof Mentha arvensis L. f. piperascens (MAO) and to evaluate the effect of its fragrant chemicals on electroencephalographic (EEG) activity of human brain. The MAO was obtained by supercritical $CO_2$ extraction. The maximum yield was 2.38% at conditions of $70^{\circ}C$ and 200 bar. There were 32 volatile chemicals with 6 alcohols (67.11%), 13 hydrocarbons (17.05%), 9 esters (11.50%), 2 ketones (7.16%), 1 oxide (2.77%), and 1 aldehyde (0.56%). The major components were (Z,Z,Z)-9,12,15-octadecatrien-1-ol (50.06%), 2-hydroxy-4-methoxyacetophenone (7.50%), and 3,4-dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one (6.60%). Results of the EEG study showed that inhalation of MAO significantly changed the EEG power spectrum values of relative gamma, relative fast alpha, and spectral edge frequency 90%. During the inhalation of MAO, the value of relative fast alpha was significantly increased (p<0.05). On the other hand, the values of gamma and the spectral edge frequency 90% were significantly decreased (p<0.05). The present study suggests that fragrant chemicals of essential oil of M. arvensis reduce the level of mental stress and that they could be used in the treatment of psychophysiological disorders.

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

  • 정형진;김은희;이건주;정규영;임종국;유정민;심영은;박재호
    • Korean Journal of Plant Resources
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    • v.14 no.3
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    • pp.220-228
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    • 2001
  • Comparison of the antioxidant potential and enzyme activities of the extracts of Rhus showed considerable differences. The antioxidative activities of Rhus javanica were the highest of three species tried (7 $\mu\textrm{g}$/$m\ell$). The highest activities showed in fraction No.3 of 12 fractions by Sephadex LH-20 column chromatography and the antioxidative activity showed, in purified extract of each stem,1.5 $\mu\textrm{g}$/$m\ell$ (in Rhus verniciflua), 1.9 $\mu\textrm{g}$/$m\ell$ (in Rhus javanica) and 2.3 $\mu\textrm{g}$/$m\ell$ (in Rhus tricocarpa) respectively. These were identificated as phenolic compounds which are well known antioxidant compounds such as 2-propenoic acid (Caffeic acid), Benzoic acid (Gallic acid), 7-hydroxy- 6methoxy-2H-1-Benzopyran-2-one (Scopoletin). POD activities of stem were higher than leaf. Especially, POD activity in stem of Rhus javanica was 193 times higher than leaf. Rhus tricocarpa, however, showed very low POD activity. SOD activities of stem were higher than that of leaf in Rhus javanica and Rhus verniciflua but in Rhus tricocarpa, the activity of leaf was 25 times higher than that of stem.

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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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    • v.6 no.4
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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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    • v.28 no.12
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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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    • v.27 no.2
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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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    • v.33 no.2
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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.

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

  • Jeong, Je-Kyo;Khang, Gil-Son;Rhee, John M.;Shin, Ho-Chul;Lee, Hai-Bang
    • Journal of Pharmaceutical Investigation
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    • v.30 no.1
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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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    • v.14 no.5
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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.