• Title/Summary/Keyword: 3'-deoxyadenosine

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Cordycepin (3'-deoxyadenosine) Has an Anti-platelet Effect by Regulating the cGMP-Associated Pathway of Human Platelet Activation

  • Cho, Hyun-Jeong;Rhee, Man-Hee;Cho, Jae-Youl;Kim, Hyeong-Soo;Ok, Woo-Jeong;Kang, Hee-Jin;Park, Hwa-Jin
    • Preventive Nutrition and Food Science
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    • v.12 no.3
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    • pp.141-147
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    • 2007
  • Cordycepin (3'-deoxyadenosine), which comes from Cordyceps militaris, the Chinese medicinal fungal genus Cordyceps, is used in the treatment of various diseases such as cancer and chronic inflammation. We recently reported that cordycepin has a novel antiplatelet effect through the down regulation of $[Ca^{2+}]_{i}$ and the elevation of cGMP/cAMP production. In this study, we further investigated the effect of cordycepin on collagen-induced platelet aggregation in the presence of cGMP-dependent protein kinase (PKG)- or cAMP-dependent protein kinase (PKA)-inhibitor. PKG inhibitor Rp-8-pCPT-cGMPS potentiated the collagen-induced platelet aggregation, but PKA inhibitor Rp-8-Br-cAMPS did not. However, both Rp-8-pCPT-cGMPS and Rp-8-Br-cAMPS reduced inhibition by cordycepin of collagen-induced platelet aggregation. Moreover, cordycepin inhibited $Ca^{2+}-dependent$ phosphorylation of both 47 kDa- and 20 kDa-protein in the presence of both PKG inhibitor and PKA inhibitor. Taken altogether, these results suggest that the inhibitory effect of cordycepin on collagen-induced platelet aggregation is associated with cGMP/PKG- and cAMP/PKA-pathways, and thus cordycepin may be an efficacious intervention against platelet aggregation-mediated thrombotic disease.

Visible and Fast Assay System for Tobacco Transformant Introduced with Adenosine Deaminase Marker Gene (Adenosine Deaminase 표지유전자로 형질전환된 연초의 신속한 Assay 방법)

  • 양덕춘;김용환;임학태;방극수;배창휴
    • Korean Journal of Plant Tissue Culture
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    • v.28 no.3
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    • pp.165-171
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    • 2001
  • New visible and fast assay system have been developed for tobacco transformant introduced with adenosine deaminase (ADA) marker gene, which converts cytotoxic adenosine analogues to non-toxic inosine analogues and ammonia. Ammonia was changed to blue color in the solution of phenol-nitoprusside and alkaline-hypochlorite. It was possible to detect activity of ADA visibly on the holes of 96 well plate using tiny explant of transgenic tobacco leaves within 1 hour incubation time. As substrates of ADA enzyme from transgenic plant on the plate, a number of adenosine analogues such as 9-D-arabinofuranosyl adenine, cordycepin, 2'-deoxyadenosine, adenosine and xylofuranosyl adenine were possible for detection of ADA activity. Optimal condition of substrate for ADA enzyme was each 10 mM and pH 7.5 in adenosine solution. Especially, transgenic plant did not convert adenosine to inosine and ammonia in the presence of ADA inhibitor deoxycoformycin, which means that ammonia produced from transgenic plant is due to expression of ADA gene. Now, we show that this detection system can be easily, sensitively, fast and cheaply as well as visibly assayed in vitro as GUS gene system with very small size of transformant explant.

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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.

Nucleoside Constituents of the Egyptian Tunicate Eudistoma laysani

  • Abou-Hussein, Dina R.;Badr, Jihan M.;Youssef, Diaa T.A.
    • Natural Product Sciences
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    • v.13 no.3
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    • pp.229-233
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    • 2007
  • Chemical investigation of the crude extract of the Egyptian marine tunicate Eudistoma laysani led to the isolation of a new nucleoside; 3-deazainosine and four known ones; inosine, 2'-deoxyuridine, adenosine and 2'-deoxyadenosine. Structural elucidation of the isolated compounds was based on intensive studies of their spectral data including 1D ($^{1}H$ and $^{13}C$) and 2D ($^{1}H-^{1}H$ COSY, HMQC, HMBC) NMR together with mass spectra. The antioxidant effects of the isolated compounds were determined using DPPH, where they exhibited significant activities.

Development of an Efficient Synthetic Method for a Novel Anticancer Substance Isolated from Insect-flower (동충하초에서 분리된 신규 항암물질의 효율적 합성법 개발)

  • Che, Hai-Yan;Truong, Ngoc Tuyen;Yoon, Deok-Hyo;Kim, Tae-Woong;Sung, Gi-Ho;Park, Hae-Il
    • YAKHAK HOEJI
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    • v.56 no.2
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    • pp.71-73
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    • 2012
  • Cordyceps militaris, a caterpillar-grown traditional medicinal mushroom, produces important bioactive compounds, cordycepin (3'-deoxyadenosine) and militarin. Militarin is reported to possess anticancer activities against several tumor cells. An efficient synthetic method of militarin was developed to prepare muti-gram scale sample for bioassay. Militarin was successfully synthesized from commercial starting materials in 5 steps and 29.3% overall yields.

Enzymatic Properties of Intracellular Adenosine Deaminase from Nocardioides sp. J-326TK

  • Hong-Ki Jun;Tae-Sook Kim
    • Journal of Life Science
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    • v.9 no.1
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    • pp.64-68
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    • 1999
  • The properties of purified intracellular adenosine deaminase (adenosine aminohydrolase, EC 3.5.4.4) of Nocardioides sp. J-326TK isolated from soil have been studied. The enzyme deaminated adenosine and 2`-deoxyadenosine and the respective {TEX}$K_{M}${/TEX} values were 4.0×{TEX}$10^{-4}${/TEX} M and 5.0× {TEX}$10^{-4}${/TEX} M, but the enzyme was not active on 8-bromoadenosine, 6-methylaminopurine riboside, ATP, ADP, 2`-AMP, 3`-AMP, 5`-AMP, dAMP, cAMP, NAD, FAD, NADP and adenine. The enzyme activity was strongly inhibited by the addition of {TEX}$Hg^{2+}${/TEX} and {TEX}$Ag^{+}${/TEX}, {TEX}$Cu^{2+}${/TEX}, {TEX}$Co^{2+}${/TEX} and {TEX}$Mn^{2+}${/TEX} also inhibited the activity but much less extent. The effect of alkyl reagents, metal chelating reagents and certain other compounds on the enzyme activity were also examined. No reagent activated the enzyme. On the contrary, the enzyme reaction was slightly inhibited by o-phenanthroline and 6-benzyladenosine.

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Flavobacterium meningosepticum의 Nucleoside Oxidase와 Peroxidase 생산특성

  • 최양문;조홍연;양한철
    • Microbiology and Biotechnology Letters
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    • v.24 no.6
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    • pp.693-698
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    • 1996
  • Optimal cultural conditions were investigated for the maximal productivity of nucleoside oxidase and peroxidase from Flavobacterium meningosepticum. Sucrose and Polypepton were the best as a carbon source and a nitrogen source. Fe$^{2+}$, Fe$^{3+}$ and Cu$^{2+}$ increased the activities of the two enzymes and were essential in medium containing peptone as a nitrogen source. Nucleoside derivatives such as 2'-deoxyguanosine, 2'-deoxyadenosine, N$^{6}$ -methyladenosine and 1-methyladenosine were effective for the production of the two enzymes. Especially, the addition of N$^{6}$ -methyladenosine and 1-methyladenosine decreased cell growth, but increased the two enzyme activities. High level of oxygen also was an essential factor for formation and/or induction of these enzymes. From the summary of this study about optimal medium and environmental conditions, nucleoside oxidase was biosynthesized in proportion to peroxidase. These results suggested that the role of peroxidase should be degradation of H$_{2}$O$_{2}$ generated by nucleoside oxidase in the cell of Flavobacterium meningosepticum.

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Cholinesterase Inhibitory Constituents from Capsosiphon fulvescens

  • Fang, Zhe;Jeong, Su Yang;Choi, Jae Sue;Min, Byung Sun;Min, Bo Kyung;Woo, Mi Hee
    • Natural Product Sciences
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    • v.18 no.4
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    • pp.233-238
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    • 2012
  • Nine compounds (1 - 9), ${\alpha}$-linolenic acid (1), cis-5,8,11,14,17-elcosapentaenoic acid (2), phytol (3), loliolide (4), uridine (5), thymidine (6), deoxyadenosine (7), adenine (8), and adenosine (9), were isolated from the n-hexane, methylene chloride, ethyl acetate and n-butanol fractions of Capsosiphon fulvescens. The structures of these compounds were elucidated on the basis of spectroscopic evidence. Compounds 1 - 9 exhibited acetylcholinesterase (AChE) inhibitory activities with $IC_{50}$ values ranging from 114.91 to $252.40{\mu}M$, whereas 2 - 4 showed butyrylcholinesterase (BChE) inhibitory activities with $IC_{50}$ values ranging from 251.18 to $499.16{\mu}M$.

Synthesis and Configurational Analysis of Diastereomers of $5^{\prime}-O-(2^{\prime}-Deoxyadenosyl)-3^{\prime}-O-(2^{\prime}$-deoxyadenosyl)-Phosphorothioate

  • Byung Jo Moon;Kyung Lan Huh;Sang Kook Kim
    • Bulletin of the Korean Chemical Society
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    • v.14 no.1
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    • pp.52-55
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    • 1993
  • A procedure is described for the synthesis of the title compound via phosphotriester intermediates. The preparation of $R_p\;and\;S_p$ diastereomeric dinucleotide of d[Ap(S)A] was performed by the condensation of protected deoxyadenosine, 2,5-dichlorophenylphosphorodichloridothioate and 1-hydroxybenzotriazole in THF. Their designation of configuration at phosphorus as $R_p\;and\;S_p$ follows from analysis of $^{31}P$-NMR spectroscopy and reversed-phase HPLC and the stereospecificity in the hydrolysis catalyzed by nuclease Pl.

Effect of Cordycepin on the Expression of the Inflammatory Cytokines TNF-alpha, IL-6, and IL-17A in C57BL/6 Mice

  • Seo, Min Jeong;Kim, Min Jeong;Lee, Hye Hyeon;Park, Jeong Uck;Kang, Byoung Won;Kim, Gi-Young;Rhu, En Ju;Kim, Jung-In;Kim, Kwang Hyuk;Jeong, Yong Kee
    • Journal of Microbiology and Biotechnology
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    • v.23 no.2
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    • pp.156-160
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    • 2013
  • Culture supernatants of splenocytes from C57BL/6 mice were exposed to 0.3, 1.0, and 3.0 ${\mu}g/ml$ cordycepin plus 3.0 ${\mu}g/ml$ lipopolysaccharide (LPS) to investigate the effects of cordycepin (3'-deoxyadenosine) on the production of inflammatory cytokines. Coadministration of 3.0 ${\mu}g/ml$ cordycepin with LPS in cultured murine spleen cells significantly diminished expression of the inflammatory cytokines tumor necrosis factor-${\alpha}$ and interleukin-6 (IL-6) in a time-dependent manner. Expression of the inflammatory cytokine IL-17A was substantially downregulated in a timeand concentration-dependent manner at all cordycepin concentrations. These findings suggest that cordycepin downregulates the immediate hypersensitivity reaction stimulated by LPS.