• Title/Summary/Keyword: 5-hydroxy-2-methyl-1

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Isolation of COX-2 Inhibitors from Alpinia officinarum (양강으로부터 COX-2 억제활성물질의 분리)

  • Kim, Ju-Sun;Son, Kun-Ho;Kim, Hyun-Pyo;Chang, Hyeun-Wook;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.31 no.1
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    • pp.57-62
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    • 2000
  • By bioassay-guided fractionation followed by chromatographic separation of the MeOH extract of Alpinia Rhizome, five COX-2 inhibitors were isolated and characterized as pinocembrin, galangin 3-methyl ether, galangin, kaempferid, and 5-hydroxy-7-(4'-hydroxy-3'-methoxyphenyl)-1-phenyl-3-heptanone.

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Studies on Volatile Flavor Compounds of Soy Sauce Residue (간장박의 휘발성 향기성분에 관한 연구)

  • Cha, Yong-Jun;Wang, Wenfeng;Cha, Ha-Ram
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.12
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    • pp.1755-1761
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    • 2016
  • Volatile flavor compounds in soy sauce residue (SSR) and acid hydrolysate of SSR (AHSSR) were analyzed by solid phase micro extraction (SPME)/gas chromatography (GC)/mass spectrometry (MSD) methods. A total of 79 compounds were detected in samples (66 SSR and 60 AHSSR). Quantitatively, alcohols (433.37 ng/g), aldehydes (273.01 ng/g), esters (236.80 ng/g), and aromatic hydrocarbons (180.66 ng/g) were dominant in the volatiles of SSR, whereas furans (249.27 ng/g) were only dominant in AHSSR (P<0.05). Among these, four esters, 3-methylbutyl acetate (banana/pear-like), ethyl 3-methyl butanoate (fruity), ethylbenzene acetate (wine-like), and ethyl 3-methyl butanoate (apple-like), three alcohols, 3-methyl-1-butanol (fruity/whisky-like), 2-phenylethanol (floral/sweet), and 1-octen-3-ol (mushroom-like), four aldehydes, (E)-2-phenyl-2-butenal (chocolate-like), benzaldehyde (almond-like), 3-methylbutanal (malty), and 2-phenylacetaldehyde (floral), four aromatic hydrocarbons, 4-ethyl-2-methoxyphenol (smoky/soy sauce-like), 4-ethylphenol (medicine-like), 4-vinyl-2-methoxyphenol (woody), and phenol (woody), and two furans, furfural (almond-like) and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), were major compounds in SSR, whereas seven compounds, including furfural, 5-methylfurfural (almond-like), 3-methyl-1-butanol, 2-phenylethanol, 4-ethyl-2-methoxyphenol, 3-methylbutanal, and benzaldehyde were major compounds in AHSSR.

Phytochemical Constituents of the Leaves of Hosta longipes

  • Kim, Chung Sub;Kim, Ki Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.86-90
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    • 2014
  • Phytochemical investigation of the 80% MeOH extract from the leaves of Hosta longipes resulted in the isolation of sixteen compounds (1 - 16). The structures of the compounds were elucidated by spectroscopic methods to be methyl 10,10-dimethoxydecanoate (1), methyl 10-hydroxy-8E,12Z-octadecadienoate (2), methyl coriolate (3), trans-phytol (4), phytene-1,2-diol (5), phyton (6), (3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol (7), (3S,5R,6S,9R)-3,6,9-trihydroxymegastigman-7-ene (8), shikimic acid (9), p-coumaramide (10), trans-N-p-coumaroyltyramine (11), cis-N-coumaroyltyramine (12), tryptophan (13), thymidine (14), adenosine (15), and deoxyadenosine (16). Compound 1 was synthesized, but not yet isolated from natural source, and compounds 2-16 were isolated for the first time from this plant source.

Lignans from the Flower Buds of Magnolia fargesii

  • Lee, Jun;Yang, Min-Suk;Nam, Sang-Hae;Shon, Mi-Yae;Hwang, Seon-Woo;Park, Ki-Hun
    • Bulletin of the Korean Chemical Society
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    • v.26 no.6
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    • pp.913-915
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    • 2005
  • The three new lignans 1-3 were isolated from the methanol extracts of the flower buds of Magnolia fargesii. They were elucidated as (7S,8R)-1-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omegahydroxypropylphenyl) propane-1,3-diol, (7S,8S)-1-(4-hydroxy-3-methoxyphenyl)-2-O-(6-hydroxy-2-methoxy-4-omegahydroxypropylphenyl) propane-1,3-diol, and [tetrahydro-4-hydroxy-2-(3,4,5-trimethoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate by spectral analysis.

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 $9.70{\mu}M$.

Study for Total Synthesis of Bruceantin Analogue(Ⅰ) (Bruceantin 유사체의 전합성에 대한 연구 (Ⅰ))

  • Ju, Jeong Ho;Choe, Jeong Jin;Kim, Hong Beom
    • Journal of the Korean Chemical Society
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    • v.38 no.1
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    • pp.80-86
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    • 1994
  • The synthetic pathway of ethyl $({\pm})$-8-oxo-10-oxa-l'H-spiro[1, 3]dioxolane-4,4'-tricyclo [9.2.1.0 1,6]dodec-6-ene-9-carboxylate (7), an important intermediate for the total synthesis of bruceantin analogue, was developed. Ethyl 2-cyclohexanonecarboxylate and methyl vinyl ketone were employed as starting materials. Robinson annulation, allylic oxidation, regiospecific acylation and the formation of epoxy methano bridge ring were studied. 4,4a,5,6,7,8-Hexahydro-4a-hydroxy-2(3H)naphthalenone (14) was synthesized utilizing the unusual decarboethoxylation reaction discovered during ketalization of octalone (3).

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Antioxidative Effectiveness and Oxidized Products in Mixture of Methyl Linoleate and Phenolic Compounds (Methyl Linoleate에 대한 Phenol성 물질의 항산화성과 산화 생성물)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.379-385
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    • 1993
  • Antioxidative effectiveness and oxidized products in mixture of methyl linoleate(ML) and phenolic compounds were investigated under oxygen blowing at $37^{\circ}C$ for 9 days. Caffeic acid (3,4-dihydroxy cinnamate ; CML) and phloroglucinol(1,3,5-trihydroxy benzene ; PML) showed higher antioxidative effectiveness for methyl linoleate than 0.05% ${\alpha}-tocopherol$ (TML). Oxidized products in ML group were methyl 8-(2-furyl)-octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In CML group the oxidized products were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer and 9-trans, trans hydroperoxide isomer, but 13-hydroxy isomer was not identified. It was shown that CML were oxidized more slowly than ML group and at 6th day of oxidation, caffeic quinone was found to be major oxidized product of caffeic acid. Oxidixed Products in PML group were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer, and 9-trans, trans hydroperoxide isomer but phloroglucinol was not oxidized even at the 9th day of reaction.

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Synthesis of Substituted Arylazothioxanthones as Potential Schistosomicidal Agents

  • El-Kerdawy, M.M.;El-Emam, A.A.;El-Subbagh, H.I.;Abushanab, E.
    • Archives of Pharmacal Research
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    • v.12 no.1
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    • pp.5-7
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    • 1989
  • A series of 1-chloro-4-methyl-6-arylazo-9H-thioxanthen-9-ones were synthesized and schistosomicidal activity evaluated. It was found that, 1-chloro-4-methyl-6-(2-hydroxy-1-naphthylazo)-9H-thioxanthen-9-one possessed a promising activity against Schisto-soma mansoni in mice.

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