• Title/Summary/Keyword: 5-hydroxy-7-(4

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Aroma Characteristic of Chungkukjang with Astragalus membranaceus (황기청국장의 향기특성)

  • Yoon Hyang-Sik;Choi Hye-Sun;Joo Seon-Jong;Kim Ki-Sik;Kim Sook-Jeong
    • Food Science and Preservation
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    • v.13 no.2
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    • pp.269-272
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    • 2006
  • Aroma compounds in chungkukjang with Astragalus membranaceus (Hwangki) were extracted by the simultaneous distillation and extraction (SDE), headspace and solid phase microextraction (SPME), and aroma compounds obtained by this method were identified with GC-MS. Thirty compounds were identified, including six ketones, eight alcohols, three heterocyclic compounds, three aldehydes, five hydrocarbones and five other compounds. Major aroma compounds were identified as 3-hydroxy-2-butanone, 2-furanmethanol, 2-methoxy-4-vinylphenol, and 4-vinylphenol in SDE, 2,3-butanedione, 3-hydroxy-2-butanone, ethanol, 2,6-dimethyl pyrazine and acetic acid in headspace and acetone, ethanol, 2,5-dimethyl pyrazine, tetramethyl pyrazine and acetic acid in SPME. The content of pyrazines identified in headspace and SPME methods was higher than that of SDE method, and the content of pyrazines containing 2,5-dimethyl pyrazine, 2,6-dimethyl pyrazine and tetramethyl pyrazine in chungkukjang was higher than that of Hwangki chungkukjang.

New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives

  • Xia, Likai;Narasimhulu, Manchala;Li, Xin;Shim, Jae-Jin;Lee, Yong-Rok
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.664-669
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    • 2010
  • This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.

Detection of 8-Hydroxy-2' -Deoxyguanosine in Human Peripheral Blood Leukocytes and Stomach Tissues (사람 백혈구 및 위 조직중의 8-Hydroxy-2'-Deoxyguanosine 측정에 관한 연구)

  • Kang Ho Il;Eom Mi Ok;Park Mi Sun;Ryeom Tai Kyung;Jee Seung Wan;Jeon Hea Myung;Kim Ok Hee
    • Environmental Mutagens and Carcinogens
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    • v.25 no.1
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    • pp.13-18
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    • 2005
  • In the present study, we have measured 8-hydroxy-2'-deoxyguanosine in DNA of stomach cancers, adjacent stomach cancer tissues, normal stomach tissues and peripheral blood leukocytes of the same stomach cancer patients (n = 48) to investigate their etiological association with gastric cancer and possibility whether peripheral blood leukocytes can use surrogate marker for early stomach cancer diagnosis by HPLC/ECD system. In normal stomach tissues, we found that 8-hydroxy-2'-deoxyguanosine levels in tissues infected with Helicobacter pylori were 1.4 fold higher than those in tissues without infected with Helicobacter pylori. However, in adjacent stomach cancer tissues, we found that 8-hydroxy-2'-deoxyguanosine levels in tissues infected with Helicobacter pylori were 1.5 fold lower than those in tissues without infected with Helicobacter pylori. In stomach cancer tissues, 8-hydroxy-2'-deoxyguanosine levels in tissues infected with Helicobacter pylori were not significantly different from those in tissues without infected with Helicobacter pylori. In Helicobacter pylori-negative specimens, 8­hydroxy-2'-deoxyguanosine levels of adjacent stomach cancer tissues were found to be significantly higher than those of normal stomach and cancer tissues. The 8-hydroxy-2'-deoxyguanosine levels of female were 1.7 fold higher than those of male in peripheral blood leukocytes of the same stomach cancer patients. The 8-hydroxy-2'­deoxyguanosine levels in Helicobacter pylori-negative specimens among adjacent stomach cancer tissues were found to be reversely correlated with those in peripheral blood leukocytes, suggesting that 8-hydroxy-2'-deox­yguanosine in peripheral blood leukocytes may not use as surrogate marker for the early diagnosis of human stomach cancer.

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Spectrophotometric Determination of Impurities such as Iron and Copper in High Purity of Antimony with 8-Hydroxy-quinoline (高純度안티몬 中의 不純物 (鐵 및 銅)의 8-Hydroxy-quinoline에 依한 吸光光度定量法)

  • Park, Kyu-Chang
    • Journal of the Korean Chemical Society
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    • v.11 no.4
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    • pp.132-137
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    • 1967
  • A spectrophotometric method for the determination of major impurities, such as iron and copper, in high purity of antimony with 8-hydroxyquinoline (oxine) has been studied. The iron-oxinate is stable at the pH range 5.0 to 5.7, and the copper-oxinate at the pH range 3.5 to 4.0. To mask antimony in sulfuric acid solution of sample, author has investigated the effect of tartaric acid on antimony, and found that 10ml of 0.5M tartaric acid solution could mask up to 600mg of antimony. The absorbance of iron-oxinate was measured at 580$m{\mu}$ and iron could be determined, but it is necessary for copper-oxinate to measure at 410 and 580m respectively after removing heavy metals other than copper by back extraction with 15% solution of sodium hydroxide, and copper could be determined by making a correction for the amounts of iron present. Up to 150 ${\mu}g$ of iron (0.005-0.03%), and 100 ${\mu}g$ of copper (0.005-0.016%), in 500mg of antimony could be determined.

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Degradation of the herbicide dicamba under sunlight and in soil (제초제 Dicamba의 자연광 및 토양 중 분해)

  • Oh, Kyeong-Seok;Oh, Byung-Youl;Park, Seung-Soon;Ihm, Yang-Bin;Kyung, Kee-Sung;Lee, Jae-Koo
    • The Korean Journal of Pesticide Science
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    • v.4 no.3
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    • pp.1-6
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    • 2000
  • In order to elucidate the degradation of the herbicide dicamba, the degradabilities of dicamba under sunlight and in soils were investigated. The photodegradation rate of the authentic dicamba under sunlight condition was only 3.3% after 9 weeks. 4-Hydroxy dicamba turned out to be the major product, and 5-hydroxy dicamba was also identified. Dicamba was degraded to 3,6-dichlorosalicylic acid by demethylation in the viable soil, which resulted in 14.7 to 23.2% degradation of the applied amount during 8 weeks of incubation. Meanwhile, the degradation was quite slow in the sterilize soil, which revealed that the soil microbes played a major role in dicamba degradation.

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Inhibitory Constituents against Cyclooxygenases from Aralia cordata Thunb

  • Dang Nguyen Hai;Zhang XinFeng;Zheng MingShan;Son Kun Ho;Chang Hyeun Wook;Kim Hyun Pyo;Bae KiHwan;Kang Sam Sik
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.28-33
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    • 2005
  • Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14), 15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), $7{\alpha}$-hydroxy-(-)-pimara-8(14), 15-dien-19-oic acid (10), $16\alpha$, 17 -dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19­oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarin­diol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to $PGE_2$ in a dose-dependent manner with $IC_{50}$ values of $134.2{\mu}M$, $121.6{\mu}M$, $170{\mu}M$, $50.4{\mu}M$, $11.7{\mu}M$, $99.6{\mu}M$, and $69.6{\mu}M$, respectively. But, most of these compounds weakly inhibited COX-2 dependent $PGE_2$ generation. Among them, only compound 4 showed relatively significant inhibitory activity $(IC_{50}\;:\;127.6{\mu}M)$.

Formation of Volatile Compounds from Maillard Reaction of D-Glucose with DL-Alanine in Propylene Glycol Solution (Propylene Glycol 용매계에서 DL-Alanine과 D-Glucose의 마이야르 반응에 의한 휘발성 화합물의 생성)

  • Kim, Young-Hoi;Kim, Ok-Chan;Lee, Jung-Il;Yang, Kwang-Ku
    • Korean Journal of Food Science and Technology
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    • v.20 no.2
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    • pp.157-163
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    • 1988
  • The volatile compounds produced from the browning reaction of 0.5M DL-alanine and 0.5M D-glucose mixture using propylene glycol as a reaction medium were analysed by gas chromatography and gas chromatography-mass spectrometry and effects of temperature($100^{\circ}C,\;120^{\circ}C,\;140^{\circ}C$) and time(20min, 2hours) on the formation of volatile compounds were investigated. Browning reaction were rapidly increased as the reaction temperature and time increased. From methylene chloride extracts, twenty six compounds, including 7 alkyl pyrazines. 4 pyrroles, 3 furans, 1 furanone and 11 miscellaneous compounds were identified. The relative amounts of pyrazines, pyrroles and furans were markedly increased as reaction temperature and time increased. The results showed that caramel-like and burnt sugar-like aroma produced by alanine -glucose reaction must be mainly comprised of nitrogeneous heterocyclic such as pyrazines, pyrroles and oxygen heterocyclic compounds such as 2-hydroxy-3-methyl-2-cyclopenten-1-one and 2,5-dimethyl-4-hydroxy-3(2H)-furanone.

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Complete $^1H$-NMR and $^{13}C$-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides

  • Yang, Heejung;Kim, Jeom Yong;Kim, Sun Ok;Yoo, Young Hyo;Sung, Sang Hyun
    • Journal of Ginseng Research
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    • v.38 no.3
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    • pp.194-202
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    • 2014
  • Background: Ginsenosides, the major ingredients of Panax ginseng, have been studied for many decades in Asian countries as a result of their wide range of pharmacological properties. The less polar ginsenosides, with one or two sugar residues, are not present in nature and are produced during manufacturing processes by methods such as heating, steaming, acid hydrolysis, and enzyme reactions. $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the identification of the less polar ginsenosides are often unavailable or incomplete. Methods: We isolated 21 compounds, including 10 pairs of 20(S) and 20(R) less polar ginsenosides (1-20), and an oleanane-type triterpene (21) from a processed ginseng preparation and obtained complete $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the following compounds, referred to as compounds 1-21 for rapid identification: 20(S)-ginsenosides Rh2 (1), 20(R)-Rh2 (2), 20(S)-Rg3 (3), 20(R)-Rg3 (4), 6'-O-acetyl-20(S)-Rh2 [20(S)-AcetylRh2] (5), 20(R)-AcetylRh2 (6), 25-hydroxy-20(S)-Rh2 (7), 25-hydroxy-20(S)-Rh2 (8), 20(S)-Rh1 (9), 20(R)-Rh1 (10), 20(S)-Rg2 (11), 20(R)-Rg2 (12), 25-hydroxy-20(S)-Rh1 (13), 25-hydroxy-20(R)-Rh1 (14), 20(S)-AcetylRg2 (15), 20(R)-AcetylRg2 (16), Rh4 (17), Rg5 (18), Rk1 (19), 25-hydroxy-Rh4 (20), and oleanolic acid 28-O-b-D-glucopyranoside (21).

Neuroprotective Compounds Isolated from Lysimachia christinae

  • Gahee Ryu;Choong Je Ma
    • Natural Product Sciences
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    • v.29 no.1
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    • pp.10-16
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    • 2023
  • We previously reported that dried Lysimachia christinae whole plant extract exerted significant neuroprotective activity. In this study, we tried to isolate neuroprotective compounds of L. christinae. We evaluated the neuroprotective activity of the four fractions (hexane, chloroform, ethyl acetate, and n-butanol fractions) of methanol extract. Among them, ethyl acetate and n-butanol fractions showed most potent neuroprotective activity against glutamate excitotoxicity. Nine compounds were isolated from ethyl acetate and n-butanol fractions of L. christinae extract and identified as cynaroside (1), (3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl-3-hydroxy-2-octyldopentaconta-23,33-dienoate (2), androst-16-ene-3,6-diol (3), 2-hydroxy-24-propoxytetracos-4-enoic acid (4), 2-hydroxy-24-methoxytetracos-4-enoic acid (5), 12-(stearoyloxy)octadec-9-enoic acid (6), β-sitosterol (7), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (8) and (1S,2S,3R,4R)-4-(((2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5R,6R)-2-(3,4-dimethoxyphenethoxy)-3,5-dihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-4-yl)oxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)cyclohexane-1,2,3-triol (9) by spectroscopic data such as UV, IR, NMR, Mass spectroscopy. Their neuroprotective activity was evaluated by MTT assay. Cynaroside (1) and androst-16-ene-3,6-diol (3) had significant neuroprotective activity against glutamate-injured HT22 cells. The neuroprotective efficacy of cynaroside (1) and androst-16-ene-3,6-diol (3) was related to their anti-oxidative activity.

Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

  • Cha, Joon Min;Kim, Dong Hyun;Lee, Tae Hyun;Subedi, Lalita;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.132-138
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    • 2018
  • Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.