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Total Synthesis,Absolute Configuration,and Biological Activity of Xyloallenoide A
Authors:San‐Yong Wang  Zhong‐Liang Xu  Hui Wang  Chun‐Rong Li  Li‐Wu Fu  Ji‐Yan Pang  Jing Li  Zhi‐Gang She  Yong‐Cheng Lin
Institution:1. School of Chemistry and Chemical Engineering, Sun Yat‐sen University, 135 Xingang West Road, Guangzhou 510275, P.?R. China (phone/fax: +86‐20‐84039623);2. Guangdong Food Industry Institute, Guangzhou 510308, P.?R. China;3. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P.?R. China
Abstract:The novel natural product xyloallenoide A, isolated from the marine mangrove endophytic fungus from the South China Sea, and its diastereoisomer xyloallenoide A1, which contain N‐methyl‐substituted amino acids, were synthesized. The absolute configurations of the amino acid units of xyloallenoide A were finally confirmed to be L ‐Lys, Me‐D ‐Val, and Me‐L ‐Ala. This report represents a practical and attractive alternative for the synthesis of N‐methyl‐substituted cyclotripeptides. In the preliminary bioassay, synthetic xyloallenoide A showed marginal activities against KB (IC50=9.6 μM ) and KBv200 cells (IC50=10.3 μM ), and xyloallenoide A1 was inactive against KB and KBv200 cells.
Keywords:Xyloallenoides A and A1  Cyclopeptides  Cytotoxic activity
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