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The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template
Mailar, K.,Choi, W.J. Elsevier Scientific Pub 2016 Carbohydrate research Vol.432 No.-
<P>A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the beta-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, beta-hydroxyl gamma-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate. (C) 2016 Elsevier Ltd. All rights reserved.</P>
Kim, Jiseon,Min, Jee Sun,Kim, Doyun,Zheng, Yu Fen,Mailar, Karabasappa,Choi, Won Jun,Lee, Choongho,Bae, Soo Kyung Elsevier 2017 Journal of pharmaceutical and biomedical analysis Vol.134 No.-
<P><B>Abstract</B></P> <P>In this study, a simple and sensitive liquid chromatography-tandem mass spectrometry (LC–MS/MS) method for the quantification of <I>trans</I>-ε-viniferin in small volumes (10μl) of mouse plasma using chlorpropamide as an internal standard was developed and validated. Plasma samples were precipitated with acetonitrile and separated using an Eclipse Plus C<SUB>18</SUB> column (100×4.6mm, 1.8-μm) with a mobile phase consisting of 0.1% formic acid in acetonitrile and 0.1% formic acid in water (60:40v/v) at a flow rate of 0.5ml/min. A triple quadrupole mass spectrometer operating in positive ion mode with selected reaction-monitoring mode was used to determine <I>trans</I>-ε-viniferin and chlorpropamide transitions of 455.10→215.05 and 277.00→111.00, respectively. The lower limit of quantification was 5ng/ml with a linear range of 5–2500ng/ml (<I>r</I> ≥0.9949). All validation data, including the selectivity, precision, accuracy, recovery, dilution integrity, and stability, conformed to the acceptance requirements. No matrix effects were observed. The developed method was successfully applied to pharmacokinetic studies of <I>trans</I>-ε-viniferin following intravenous (2.5mg/kg), intraperitoneal (2.5, 5 and 10mg/kg), and oral (40mg/kg) administration in mice. This is the first report on the pharmacokinetic properties of <I>trans</I>-ε-viniferin. The results provide a meaningful basis for evaluating the pre-clinical or clinical applications of <I>trans</I>-ε-viniferin.</P> <P><B>Highlights</B></P> <P> <UL> <LI> First LC–MS/MS method for <I>trans</I>-ε-viniferin quantification in mouse plasma. </LI> <LI> A simple protein precipitation that allowed for efficient/reproducible recovery yields was used. </LI> <LI> The small plasma volume (10μl) supports the ability to examine pharmacokinetics in mice. </LI> </UL> </P>