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  • 标题:(+)/(−)-Phaeocaulin A-D, four pairs of new enantiomeric germacrane-type sesquiterpenes from Curcuma phaeocaulis as natural nitric oxide inhibitors
  • 本地全文:下载
  • 作者:Gui-yang Xia ; De-juan Sun ; Jiang-hao Ma
  • 期刊名称:Scientific Reports
  • 电子版ISSN:2045-2322
  • 出版年度:2017
  • 卷号:7
  • 期号:1
  • DOI:10.1038/srep43576
  • 语种:English
  • 出版社:Springer Nature
  • 摘要:Germacrane-type sesquiterpenes, with a flexible 10-membered ring unit as the structural and conformational features, play a central role in the biosynthesis and synthesis of other sesquiterpenes. In this report, two pairs of new sesquiterpene alkaloids, (+)/(-)-phaeocaulin A [(+)-1/(-)-1] and B [(+)-2/(-)-2], and two pairs of new sesquiterpenes, (+)/(-)-phaeocaulin C [(+)-3/(-)-3] and D [(+)-4/(-)-4], along with one related known analog (5), were isolated from the rhizomes of Curcuma phaeocaulis. The absolute configurations of (+)-1/(-)-1, (+)-2/(-)-2, (+)-3/(-)-3 and (+)-4/(-)-4 were unambiguously determined by analysis of single-crystal X-ray diffractions and quantum chemical electronic circular dichroism (ECD) method. It is noteworthy that (+)/(-)-phaeocaulin A [(+)-1/(-)-1] and B [(+)-2/(-)-2] are two pairs of rare N-containing germacrane-type sesquiterpenes. A possible biogenetic pathway for 1-5 was postulated. All of the isolated compounds were tested for their inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages.
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