• Title/Summary/Keyword: beta-hydroxy acid

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The crystal and molecular structure of $\gamma$-hydroxy-.$\beta$-amino butyric acid

  • Kim, Yang-Bae
    • Archives of Pharmacal Research
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    • v.8 no.1
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    • pp.1-6
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    • 1985
  • The crystal structure or $\gamma$-hydroxy-$\betha$-aminobutyric acid was determined by MULTAN system with X-ray intensity data on a diffractometer and refined by the least-squares method to an R-value 0.034 for 711 reflections. The crystals were orthorhombic, space group $P2_{1}2_{1}2_{1}$, Z = 4, with a = 10.220, b = 8.257 and c = 6.556$\AA$. The molecule takes the zwitterionic form and skeletal conformation is trans-transform. The molecules are held together by intra-and intermolecular NH-O and OH--O hydrogen bonds.

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Triterpenes and Phenolic Constituents from Viscum album L. (상기생의 트라이테르펜 및 페놀성 성분)

  • 최상진;권학철;정애경;최상운;김경란;이선미;표석능;이강노
    • YAKHAK HOEJI
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    • v.45 no.6
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    • pp.591-598
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    • 2001
  • The photochemical study of Viscum album (Loranthaceae) led to the isolation of twelve compounds, lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$- spinasterol (7), oleanolic acid (8) , 5-hydroxy-1- (4′-hydoxyphenyl) -7- (4"-hydroxyphenyl) -hepta-1- en-3-on (9), 2′-hydroxy -4′, 6′- dimethoxychalcone -4-O-glycoside (10) ,2′-hydroxy-4′, 6′-dimethoxychalcone -4-O- [apiosal(1longrightarrow12)]glucoside (11) and syringin (12). Their structures were established by chemical and spectroscopic methods. The cytotoxicity of the isolated compounds was evaluated by sulforhodamine B assay against five cultured human tumor cell lines.

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Isolation and Structural Elucidation of Related Impurities in Canrenone

  • Yang, Ya-Xi;Chen, Guo-Rong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2398-2402
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    • 2009
  • Ten steroidal compounds as impurities in canrenone were isolated from the enriched mother liquor by using various chromatographic methods. Their structures were elucidated by spectrometric analysis, among which three new compounds were characterized as 3-(3-oxo-7$\alpha$-(ethoxycarbonyl)methyl-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (1), 3-(3-oxo-7$\alpha$-ethoxy-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (2) and 3-(3-oxo- 5$\beta$-propionic acid-$\gamma$-lactone-6$\beta$,17$\beta$-hydroxy-4-androstan-17$\alpha$-yl) propionic acid $\gamma$-lactone (3).

Cerebrosides and Terpene Glycosides from the Root of Aster scaber

  • Kwon, Hak-Cheol;Cho, Ock-Ryun;Lee, Kang-Choon;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.26 no.2
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    • pp.132-137
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    • 2003
  • Three cerebrosides 2, 3, and 5 and two terpene glycosides 1 and 4 have been isolated from the methanol extract of the root of Aster scaber. Their structures were determined as 3-Ο-$\beta$-D-glucuronopyranosyl-oleanolic acid methyl ester (1), (2S, 3S, 4R, 2 R, 8Z, 15 Z)-N-2 -hydroxy-15 -tetracosenoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (2), (2S, 3S, 4R, 8Z)-N-octadecanoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (3), 1$\alpha$-hydroxy-6$\beta$-Ο-$\beta$-D-glucosyl-eudesm-3-ene (4), and (2S, 3S, 4R, 2 R, 8Z)-N-2 -hydroxy-hexadecanoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (5) on the basis of spectroscopic methods.

Antioxidative Constituents from the Seeds of Cuscuta chinensis

  • Kwon, Yong-Soo;Chang, Bok-Sim;Kim, Chang-Min
    • Natural Product Sciences
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    • v.6 no.3
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    • pp.135-138
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    • 2000
  • MeOH extract of Cuscuta chinensis seeds was fractionated with n-hexane, EtOAc and BuOH successively, and antioxidant activities were tested for all fractions using DPPH free radical scavenging method. In the tested fractions, EtOAc fraction showed high antioxidant activity$(EC_{50},\;50\;{\mu}g)$ From the EtOAc fraction, five compounds have been isolated. On the basis of spectral data, these compounds were identified as ${\beta}-sitosterol$, methyl 4-hydroxy-3,5-dimethoxycinnamate, ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$, caffeic acid, quercetin, kaempferol and calycopteretin. Among these compounds, ${\beta}-sitosterol$ and ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$ showed no antioxidant activity. $EC_{50}$ values of methyl 4-hydroxy-3,5-dimethoxycinnamate, caffeic acid, quercetin, kaempferol and calycopteretin were 0.6, 8, 19, 17 and $12\;{\mu}g$, respectively.

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Studies on the Synthesis of Mannich Bases of Hexachlorophene and their Antimicrobial Activities (Hexachlorophene의 Mannich Bases 합성 및 항미생물작용에 관한 연구)

  • Kim, Jong-Ho;Bae, Moo;Lee, Gye-Jun
    • Microbiology and Biotechnology Letters
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    • v.1 no.1
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    • pp.43-50
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    • 1973
  • Thirty-three Mannich bases of 2,2'-methylene bis (3,4, 6-trichlorophenoxy-acetic acid) were synthesized hexachlorophene as potential antimicrobial agents and tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger and Aspergillus oryzae in vitro. It was found that: 1) 2,2'-Methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$- (N,N -diethylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(N, N-dimethynlamo) propionoic acid] were active against Staphylococcus aureus and Bacillus subtilis at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 2) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid] were active against Trichophyton-rubrum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 3) 2,2'-Methylene bis [${\alpha}$-3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenyl-amino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trcihlorophenoxy)-${\beta}$-(piperidino) propionic acid] were active against Microsporum gypseum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 4) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3, 4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxy phenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chlorophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chloro-p-nitrophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$- (3,4,6-trichlorophenoxy)-${\beta}$-(methylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorphenoxy)-${\beta}$-(morpholino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-sulfophenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(4-sulfu-l-nayphthlamino) aoi!c rppioncd (were active against Epidermophyton floccosum at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 5) 2,2'-Methlene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis (a-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-methylphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid] were active against Aspergillus niger and Aspergillus oryzae at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively.

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Two-Stage Microbial Biotransformation for the Production of 6-Dodecen-4-olide (Butter Lactone) from Plant Oils Containing Unsaturated Fatty Acids (불포화 지방산 함유 식물유를 이용한 천연 6-Dodecen-4-oilde (Butter Lactone) 생산을 위한 2-Stage Microbial Biotransformation)

  • Kwon, Soon-Hyang;Kim, Kyoung-Ju;Kim, Yang-Hwi Augustine
    • Korean Journal of Microbiology
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    • v.43 no.2
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    • pp.130-136
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    • 2007
  • Natural 6-dodecen-4-olide (Butte lactone) was produced from plant oils containing high unsaturated fatty acids via two-stage microbial hiotransformation. After unsaturated fatty acids were liberated from plant oil by microbial lipase, these were converted to optically active hydroxyl fatty acid (HFA) by hydroxylation reaction of Pseudomonas sp. NRRLB-2994. When safflower oil containing >75% unsaturated fatty acid, linoleoic acid wasused, Pseudomonas sp. produced 8g/L of 10-hydroxy-12(z)-octadecanoicacid with average of 39.2% bioconversion efficiency during 48 hr biotransformation period. The recovered 10-hydroxy-12-octadecanoic acid was further bioconverted to 4-hydroxy-6-dodecenoic acid via partial ${\beta}-oxidation$ by Yarriowia lipolytica ATCC34088. 4-hydroxy-6-dodecenoic acid in culture was lactonized by lowering pH to 4.0 using $4N\;H_{2}SO_{4}$ and heating for 5 min to 6-dodecen-4-olide (Butter lactone). Natural 6-dodecen-4-olide had characteristic aroma properties when compared to 6-dodecan-4-oilde (dodecalactone) and 4-decen-4-olide (decalactone).

A sapogenin of randia siamensis

  • Woo, Won-Sick;Choi, Jae-Sue;Tovivich, Phichai
    • Archives of Pharmacal Research
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    • v.7 no.1
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    • pp.57-60
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    • 1984
  • From the roots of Randia siamensis (Rubiaceae), 3${\beta}$, 30-dihydroxy-urs-12en-28-oic acid (30-hydroxy ursolic acid) was isolateed and characterized by spectral data.

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Synthesis of Substituted Pyridine-2, 4-dione Nucleosides

  • Joon, Joon-Kwang;Won, Jeong-Hee;Park, Jung-Sup;Hwang, Chang-Ho;Chung, K.H.;Ryu, Eung K.
    • Archives of Pharmacal Research
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    • v.15 no.1
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    • pp.87-90
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    • 1992
  • The syntheses of novel heterocyclic base modified pyrimidine nucleosides are described. 5, 6-dimethyl-4-hydroxy-3-methoxy-1-$(\beta$-D-ribofuranosyl)2(1H)-pyridinone 7 was synthesized by condensation of silylated 5, 6-dimethyl4-hydroxy-3-methoxy-2(1H)-pyridione 7 was synthesized by condensation of silylated 5, 6-dimethyl-4-hydroxy-3-methoxy-2(1H)-pyridinone with $\beta$-D-ribofuranose-1-acetate-2, 3, 5-tribenzoate in dichloroethane in the presence of Lewis acid followed by debenzoylation. The 2, 2'-anhydro-5, 6-dimethyl-2-hydroxy-3-methoxy-1-$\beta$-D-arabinofuranosyl-4-pyridinone 8 was obtained from the reaction of the free ribonucleoside 7 and diphenyl carbonate in DMF. None of these compounds showed any significant antiviral ad antitumor activities in vitro tests.

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