Americanin, a bioactive dibenzylbutyrolactone lignan, form the seeds of Centaurea americana

M. Shoeb, S. M. MacManus, Y. Kumarasamy, Marcel Jaspars, L. Nahar, P. K. Thoo-Lin, H. Nazemiyeh, S. D. Sarker

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32 Citations (Scopus)

Abstract

The reversed-phase preparative HPLC analysis of the methanol (MeOH) extract of the seeds of Centaurea americana afforded a dibenzylbutyrolactone lignan, 3"-O-caffeoyl arctiin (named americanin), together with five known lignans, arctiin, arctigenin, matairesinol, matairesinoside and lappaol A, and two known phytoecdysteroids, 20-hydroxyecdysone and makisterone A. While the structures of the known compounds were determined by direct comparison of the spectral data with published data, the structure of americanin was elucidated by UV, MS and a combination of I D and 2D NMR spectral analyses. The antioxidant properties and toxicity of the extracts and the isolated compounds were determined by the DPPH and the brine shrimp lethality assays, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2370-2375
Number of pages5
JournalPhytochemistry
Volume67
Issue number21
Early online date22 Sep 2006
DOIs
Publication statusPublished - Nov 2006

Keywords

  • Centaurea americana
  • Asteraceae
  • Compositae
  • lignan
  • phytoecdysteroid
  • DPPH
  • brine shrimp lethality assay
  • makisterone A
  • antioxidant
  • chemotaxonomy
  • sesquiterpene lactones
  • chemical-constituents
  • secondary metabolites
  • structure elucidation
  • antifungal activity
  • biological-activity
  • indole alkaloids
  • aerial parts
  • guaianolides
  • compositae

Cite this

Shoeb, M., MacManus, S. M., Kumarasamy, Y., Jaspars, M., Nahar, L., Thoo-Lin, P. K., Nazemiyeh, H., & Sarker, S. D. (2006). Americanin, a bioactive dibenzylbutyrolactone lignan, form the seeds of Centaurea americana. Phytochemistry, 67(21), 2370-2375. https://doi.org/10.1016/j.phytochem.2006.08.012