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Synthesis and Antitumor Evaluation of N-Alkyl-N-Nitrosocarbamoyl-$\alpha$-Amino- and 3$\beta$-Amino-$\alpha$-Cholestane Derivatives (N-Alkyl-N-Nitrosocarbamoyl-3$\alpha$-Amino-와 3$\beta$-Amino-5$\alpha$-Cholestane 유도체들의 합성 및 항암작용 평가)

  • 김정균;최순규;조인섭;유동식;유성호;문경호
    • YAKHAK HOEJI
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    • v.29 no.2
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    • pp.62-69
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    • 1985
  • The isomeric intermediates, $3{\alpha}$and $3{\beta}-amino-5{\alpha}-cholestane required for the synthesis of N-nitrosoureas, N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\alpha}-amino-5{\alpha}$-cholestane (9), N-methyl-N-nitrosocarbamoyl-3${\alpha}-amino-5{\alpha}-cholestane$ (10), N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$: (7), and N-methyl-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$ (8) were obtained through the $LiAlH_{4}$ reduction of $5{\alpha}$-cholestan-3-one oxime, followed by the chromatographic separation: the assignment of the stereochemistry of both isomers were based on the shape and chemical shift of $C_{3}$-proton resonances on their NMR spectra and on the elution mobility on the TLC. The urea intermediates, N-(2-chloroethyl) carbamoyl-3.alpha.-amino-5.alpha.-cholestane (13), N-methylcarbamoyl-$3{\alpha}-amino-5{\alpha}-cholestane$ (14), N-(2-chloroethyl) carbamoyl-$3{\beta}-amino-5{\alpha}-cholestane (11) and N-methyl-$3{\beta}-amino-5{\alpha}$-cholestane (12) were prepared by the treatment of each isomers ($3{\alpha}$-amino-and $3{\beta}-amino-5{\alpha}$-cholestane) with alkyl isocyanates in anhydrous $CHCl_{3}$, and the corresponding nitrosoureas, 7-10 were obtained by the nitrosation of the ureas, 11-14, with AcOH (or HCOOH)/$NaNO_{2}$ in ice-cold condition. The inhibitory activity of the nitrosoureas, 7-10, and their intermediates, 12-14 towards the growth of L1210 murine leukemia cells, were examined. Among them, the compounds 9 and 10 exhibited high activity having $ED_{50}$ to be 5.5g/ml and 6.1g/ml, respectively.

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Flavonol Glycosides of Maesa Lanceolata Leaves

  • Manguro, Lawrence O. Arot;Lemmen, Peter;Ugi, Ivar;Kraus, Wolfgang
    • Natural Product Sciences
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    • v.8 no.3
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    • pp.77-82
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    • 2002
  • An investigation of the methanolic extract of Maesa lanceolata leaves has led to the isolation of four novel flavonol glycosides characterised as myricetin 3-0-2', 3', 4'-triacetylxylopyranoside (1), quercetin $3-O-{\beta}-3'$, $6'-diacetylglucopyranosyl-(1{\longrightarrow}4)-{\alpha}-2'$, 3'-diacetylrhamnopyranoside (2), myricetin $3-O-xylopyranosyl-(1{\to}3)-{\alpha}-rhamnopyranoside$ (3) and quercetin $3-O-{\beta}-ga1actopyranosyl-(1{\to}4)-{\alpha}-rhamnopyranoside-7-O-{\beta}-galactopyranoside$ (4). Also isolated from the same extract were known flavonols; quercetin (5), myricetin (6), quercetin 3-O-xylopyranoside (7), quercetin $3-O-{\alpha}-rhamnopyranoside$ (8), myricetin $3-O-{\alpha}-rhamnopyranoside$ (9), myricetin $3-O-{\beta}-galactopyranoside$ (10) and quercetin 3-O-rutinoside (11).

Enhanced Sialylation of Recombinant Erythropoietin in CHO Cells by Human Glycosyltransferase Expression

  • Jeong, Yeon-Tae;Choi, One;Lim, Hye-Rim;Son, Young-Dok;Kim, Hong-Jin;Kim, Jung-Hoe
    • Journal of Microbiology and Biotechnology
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    • v.18 no.12
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    • pp.1945-1952
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    • 2008
  • Sialylation, the attachment of sialic acid residues to a protein, can affect the biological activity and in vivo circulatory half-life of glycoproteins. Human ${\alpha}2$,3-sialyltransferase (${\alpha}2$,3-ST) and ${\beta}1$,4-galactosyltransferase (${\beta}1$,4-GT) are responsible for terminal sialylation and galactosylation, respectively. Enhanced sialylation of human erythropoietin (EPO) by the expression of ${\alpha}2$,3-ST and ${\beta}1$,4-GT was achieved using recombinant Chinese hamster ovary (CHO) cells (EC1). The sialic acid content and sialylation of N-glycans were evaluated by HPLC. When ${\alpha}2$,3-ST was expressed in CHO cells (EC1-ST2), the sialic acid content (moles of sialic acid/mole of EPO) increased from 6.7 to 7.5. In addition, the amount of trisialylated glycans increased from 17.3% to 26.1 %. When ${\alpha}2$,3-ST and ${\beta}1$,4-GT were coexpressed in CHO cells (EC1-GTST15), the degree of sialylation was greater than that in EC1-ST2 cells. In the case of EC1-GTST15 cells, the sialic acid content increased to 8.2 and the proportion of trisialylated glycans was markedly increased from 17.3% to 35.5%. Interestingly, the amount of asialoglycans decreased only in the case of GTST15 cells (21.4% to 14.2%). These results show that coexpression of ${\alpha}2$,3-ST and ${\beta}1$,4-GT is more effective than the expression of ${\alpha}2$,3-ST alone. Coexpression of ${\alpha}2$,3-ST and ${\beta}1$,4-GT did not affect CHO cell growth and metabolism or EPO production. Thus, coexpression of ${\alpha}2$,3-ST and ${\beta}1$,4-GT may be beneficial for producing therapeutic glycoproteins with enhanced sialylation in CHO cells.

The Volatile Composition of Kiyomi Peel Oil (Citrus unshiu Marcov×C. sinensis Osbeck) Cultivated in Korea

  • Song, Hee-Sun
    • Preventive Nutrition and Food Science
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    • v.13 no.4
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    • pp.292-298
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    • 2008
  • The volatile composition of Kiyomi peel oil cultivated in Korea was studied by using gas chromatography and gas chromatography-mass spectrometry. The peel oil from the Kiyomi fruit was prepared by using a cold-pressing extraction method. Among the 65 components quantified in Kiyomi oil, 25 terpene hydrocarbons and 40 oxygenated compounds were identified, with peak weight percentages measuring 94.5% and 4.9%, respectively. Limonene was the predominant compound (87.5%), followed by myrcene (2.4%), sabinene (0.9%), $\alpha$-pinene (0.8%), $\beta$-sinensal (0.8%), (Z)-$\beta$-farnesene (0.7%), neryl acetate (0.6%), valencene (0.5%), $\alpha$-farnesene (0.5%), and $\alpha$-sinensal (0.5%). A unique characteristic of the volatile profile of the Kiyomi oil was the proportion of aldehydes (2.7%), which resulted from the relative abundance of $\alpha$- and $\beta$-sinensal. Another unique characteristic of the Korean Kiyomi oil was its relative abundance of $\beta$-sinensal, (Z)-$\beta$-farnesene, neryl acetate, valencene, $\alpha$-sinensal and nootkatone. Valencene and $\alpha$- and $\beta$-sinensal were regarded as the influential components of Korean Kiyomi peel oil.

Constituents of Aerial Parts from Erechtites hieracifolia (붉은서나물 지상부의 성분)

  • 이재훈;권학철;최상진;이원빈;방은정
    • YAKHAK HOEJI
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    • v.45 no.4
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    • pp.339-346
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    • 2001
  • A new oxygenated monoterpene (4) was isolated from the methanol extract of the aerial part of Erechtites hieracifolia together with six known components, a dimethylheptane (1), three ionone derivatives (2, 3 and 7) and two phenylpropanoids (5 and 6). Their structures were identified by means of physico-chemical and spectral data to be (2E, 5E)-6-hydroxy-2,6-dimethylhepta-2,4-dienal (1), 3(R)-hydroxy-5,6-epoxy-$\beta$-ionone (2), 3(R)-hydroxy-5,6-epoxy-7-ionol (3), (3E, 6E)-3,7-dimethylocta-3,5-dien-1,2,7-triol(4), 2-hydroxy-4-(2-propenyl)phenyl-$\beta$-D-glucopyranoside (5), 2-methoxy-4-(2-propenyl)phenyl -$\beta$-D-glucopyra-noside (6) and (6R, 9R)-3-oxo-$\beta$-ionol-$\alpha$-D -glucopyranoside (7).

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Opposing Effects of Arkadia and Smurf on TGFβ1-induced IgA Isotype Expression

  • Choi, Seo-Hyun;Seo, Goo-Young;Nam, Eun-Hee;Jeon, Seong-Hyun;Kim, Hyun-A;Park, Jae-Bong;Kim, Pyeung-Hyeun
    • Molecules and Cells
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    • v.24 no.2
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    • pp.283-287
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    • 2007
  • $TGF-{\beta}1$ induces Ig germ-line ${\alpha}$ ($GL{\alpha}$) transcription and subsequent class switching recombination (CSR) to IgA. In the present study, we investigated the roles of two E3-ubiquitin ligases, Smurfs (HECT type) and Arkadia (RING finger type) on $TGF{\beta}1$-induced IgA CSR. We found that over-expression of Smurf1 and Smurf2 decreased $TGF{\beta}1$-induced $GL{\alpha}$ promoter activity and strengthened the inhibitory effect of Smad7 on the promoter activity. Further, over-expression of Smurf1 and Smurf2 decreased both Smad3/4-mediated and Runx3-mediated $GL{\alpha}$ promoter activities, suggesting that the Smurfs can down-regulate the major $TGF-{\beta}1$ signaling pathway and decrease $GL{\alpha}$ gene expression. In parallel, the over-expressed Smurf1 decreased the expression of endogenous IgA CSR-predictive transcripts ($GLT_{\alpha}$, $PST_{\alpha}$, and $CT_{\alpha}$) and also $TGF{\beta}1$-induced IgA secretion. Conversely over-expression of Arkadia abolished the inhibitory effect of Smad7 on $TGF{\beta}1$-induced $GLT_{\alpha}$ expression and IgA secretion. Similar results were obtained in the presence of over-expressed Smad7 and Smurf1. These results indicate that Arkadia can amplify $TGF{\beta}1$-induced IgA CSR by degrading Smad7, which interacts with Smurf1. We conclude that Smurf and Arkadia have opposite roles in the regulation of $TGF{\beta}1$-induced IgA isotype expression.

Stabilization of Barley $\beta$-Amylase by Modification with $IO_4$-Oxidized Starch ($IO_4$-산화전분 변형에 의한 보리 $\beta$-Amylase의 안정성 증가)

  • 안용근
    • The Korean Journal of Food And Nutrition
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    • v.13 no.4
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    • pp.342-347
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    • 2000
  • The stabilization of barley $\beta$-amylase(Biozyme ML, Amano) was attained by modification with periodate-oxidized soluble starch. The specific activities of modified enzyme at pH 9.7 and pH 8.0 were 42% and 92%, respectively, compared with that of native enzyme. The pH stability of modified enzyme was increased at pH 2~5 and 7~12 in the presence of $\alpha$-cyclodextrin( $\alpha$ -CD) compared wish that of native enzyme. Thermal stability of the modified enzyme was increased. After treatment at 6$0^{\circ}C$ for 10min. the activity remained 8% for the enzyme modified at pH 8.0 in the presence of $\alpha$-CD, 4.5% for the native enzyme. The native enzyme and modified enzyme showed two peak in HPLC. The molecular weight of the modified enzyme was slightly increased in HPLC analysis.

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High temperature deformation behavior of $\alpha\;and\;\beta$ phase of Ti-6Al-4V alloy with an equiaxed microstructure (등축정 Ti-6Al-4V 합금의 $\alpha,\;\beta$ 구성상의 고온변형거동 규명)

  • Lee, You-Hwan;Yeom, Jong-Taek;Park, Nho-Kwang;Lee, Chong-Soo;Kim, Jeoung-Han
    • Proceedings of the Korean Society for Technology of Plasticity Conference
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    • 2005.05a
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    • pp.295-298
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    • 2005
  • High temperature deformation behavior of $\alpha\;and\;\beta$ phase of Ti-6Al-4V was investigated within the framework of a self-consistent approach at various temperature ranges. To examine the flow behavior of u-phase, Ti-7.0Al-1.5V alloy was used, whose chemical composition is close to that of the $\alpha$ phase in Ti-6Al-4V at hot working temperatures. The flow stress of $\beta$ phase was predicted by using self-consistent approach. The flow stress of $\alpha$ phase was higher than that of $\beta$ phase above $750^{\circ}C$, while the $\beta$ phase revealed higher flow stress than a phase at $650^{\circ}C$. It was found that the relative strength and strain rate ratio between $\alpha\;and\;\beta$ phase significantly varied with temperature. From this approach, the mode for grain matrix deformation was proposed as a mixed type of both iso-stress and iso-strain rate modes.

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The Effect of Acupuncture at PC7(Daereung) on EEG in Normal Human Subject (대릉(大陵)(PC7) 침자가 뇌파에 미치는 영향)

  • Park, Cheol-Jin;Lee, Sang-Ryong
    • Korean Journal of Acupuncture
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    • v.27 no.2
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    • pp.141-157
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    • 2010
  • Objectives : The aim of this study is to examine the effects of acupuncture at PC7(Daereung) on normal human EEG using power spectral analysis. Methods : EEG power spectrum exhibits site-specific and state-related differences in specific frequency bands. In this study, power spectrum was used as a measure of complexity. 30 subjects (16 males and 14 females; averaged age = 23.4 years) were engaged with thirty channel EEG study. Results : In $\alpha$(alpha) band, the power values at Fp1, Fp2, F7, F8 channels(p<0.05) during PC7 treatment were significantly decreased. But, the power values at Fz channel(p<0.05) during non-acupoint treatment was significantly decreased. In $\beta$(beta) band, the power values at Fp1, Fp2 channels(p<0.05) during PC7 treatment were significantly decreased. But, the power values at Fz channel(p<0.05) during non-acupoint treatment was significantly decreased and at F8, TCP2 channels(p<0.05) during non-acupoint treatment were increased. In $\theta$(theta) band, the power values at Fp1, Fp2, F7, F8 channels(p<0.05) during PC7 treatment were significantly decreased. But, the power values at Fz channel(p<0.05) during non-acupoint treatment was significantly decreased. In $\delta$(delta) band, the power values at Fp1, Fp2, F7, Fz, F8 channels (p<0.05) during PC7 treatment were significantly decreased. But, the power values at Fz channel (p<0.05) during non-acupoint treatment was significantly decreased. $\alpha/\beta$ values during PC7 treatment were decreased. $\beta/\theta$ values during PC7 treatment were decreased. Conclusion : These results suggest that acupuncture at PC7 induce the change on $\alpha$(alpha), $\beta$(beta), $\theta$ (theta), $\delta$(delta) wave values being decreased and and bothe $\alpha/\beta$ and $\beta/\theta$ values being decreased respectively. This is considered that acupuncture at PC7 affects the activity of cerebral cortex and endocrine system.

Synthesis and $5{\alpha}$-Reductase Inhibitory Activity of $3{\beta}$-Substituted 5-Androstene-17-Carboxamides ($3{\beta}$-치환 5-Androstene-17-Carboxamides 합성과 $5{\alpha}$-Reductase 저해 활성)

  • Jo, Ik-Sung;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.54 no.6
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    • pp.466-473
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    • 2010
  • A series of $3{\beta}$-substituted 5-androstene-$17{\beta}$-carboxamides were synthesized from analogs of $3{\beta}$-hydroxy-5-androstene-$17{\beta}$-carboxylic acid (1) with tert-butylamine, N,N-diethylamine and 3-aminopyridine and some compounds were epoxidized with mCPBA. A rat prostate testosterone $5{\alpha}$-reductase inhibitory activity of synthesized compounds was assessed by radioimmunoassay using [1,2,6,7-3H]-testosterone as substrate. All synthesized compounds showed lower activity than finasteride and the N-(3-pyridino)-$3{\beta}$-carboxycarbonyloxy-5-androstene-$17{\beta}$-carboxamide (12) showed weak inhibitory activity ($IC_{50}$: $2.4{\times}10^{-7}M$).