Biofilm blocking sesquiterpenes from Teucrium polium

Wael A. Elmasri, Mohamed-Elamir F. Hegazy, Mina Aziz, Ekrem Koksal, Wail Amor, Yehia Mechref, Abdul N. Hamood, David B. Cordes, Paul W. Pare*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

The chemical composition and antibacterial activity of Teucrium polium L. (Lamiaceae) were assessed; sixteen compounds were isolated from a CH2Cl2/MeOH extract of the aerial parts of the plant including four sesquiterpenes 4 beta,5 alpha-epoxy-7 alpha H-germacr-10(14)-en-6 beta-ol-1-one, 4 beta,5 alpha-epoxy-7 alpha H-germacr-10(14)-en,1 beta-hydroperoxy1,6 beta-ol, 4 beta,5 alpha-epoxy-7 alpha H-germacr-10(14)-en,1 beta-hydroperoxy1,6 beta-ol and 4 beta,5 alpha-epoxy-7 alpha H-germacr-10(14)-en,1 beta-hydroperoxyl,6 alpha-ol, together with seven known sesquiterpenes, one known iridoid glycoside, two known flavonoids, and one known phenylpropanoid glycoside. Structures were elucidated on the basis of spectroscopic (UV, H-1 and C-13 NMR) data, as well as two-dimensional NMR (H-1-H-1 COSY, HMQC, NOESY and HMBC), and ESI-MS analysis. The relative stereochemistiy of the ketone was established by X-ray crystallography, while its absolute configuration was attained by a modified Mosher's method. Antibacterial activity of the crude extract, as well as with four of the isolated metabolites, was observed with Staphylococcus aureus anti-biofilm activity in the low mu Mol range. Diverse sesquiterpene-skeleton structure and corresponding comprehensive enzyme capacity is discussed.

Original languageEnglish
Pages (from-to)107-113
Number of pages7
JournalPhytochemistry
Volume103
Early online date12 Apr 2014
DOIs
Publication statusPublished - Jul 2014

Keywords

  • Teucrium polium
  • Lamiaceae
  • Sesquiterpenes
  • Biofilm blocking
  • Essential oil
  • Antioxidant activity
  • Cichorium-intybus
  • Mass-spectrometry
  • L.
  • Biotransformation
  • 7-EPI-eudesmanes
  • Constituents
  • Diterpenoids
  • Glycosides

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