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Total Synthesis, Absolute Configuration, and Biological Activity of Xyloallenoide A
Author(s) -
Wang SanYong,
Xu ZhongLiang,
Wang Hui,
Li ChunRong,
Fu LiWu,
Pang JiYan,
Li Jing,
She ZhiGang,
Lin YongCheng
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100437
Subject(s) - chemistry , absolute configuration , diastereomer , natural product , stereochemistry , total synthesis , bioassay , amino acid , mangrove , biochemistry , ecology , biology
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 ( IC 50 =9.6 μ M ) and KBv200 cells ( IC 50 =10.3 μ M ), and xyloallenoide A1 was inactive against KB and KBv200 cells.
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