Flueggines A and B, two new dimeric indolizidine alkaloids from Flueggea virosa

Org Lett. 2011 Aug 5;13(15):3888-91. doi: 10.1021/ol201410z. Epub 2011 Jul 5.

Abstract

Two unprecedented C,C-linked dimeric indolizidine alkaloids, flueggines A (1) and B (2), were isolated from the twigs and leaves of Flueggea virosa. The structures and absolute configurations were elucidated by means of NMR, single-crystal X-ray diffraction, and CD analyses. Compound 1 is the first example of Securinega alkaloids bearing an isoxazolidine ring, the plausible biogenetic pathway of which is also proposed. Compound 2 exhibited growth inhibitory activity against MCF-7 and MDA-MB-231 human breast cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dimerization
  • Humans
  • Indolizidines / chemistry*
  • Indolizidines / pharmacology
  • Indolizines / chemistry*
  • Indolizines / pharmacology
  • Magnoliopsida / chemistry*
  • Models, Molecular
  • Molecular Structure

Substances

  • Alkaloids
  • Indolizidines
  • Indolizines
  • flueggine A
  • flueggine B