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 Paré

doi:10.1016/j.phytochem.2014.03.029

Biofilm blocking sesquiterpenes from Teucrium polium

Phytochemistry. 2014 Jul:103:107-113. doi: 10.1016/j.phytochem.2014.03.029. Epub 2014 Apr 12.

Authors

Wael A Elmasri¹, Mohamed-Elamir F Hegazy², Mina Aziz¹, Ekrem Koksal¹, Wail Amor³, Yehia Mechref¹, Abdul N Hamood³, David B Cordes¹, Paul W Paré⁴

Affiliations

¹ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
² Chemistry of Medicinal Plants/Center Excellence Science, National Research Centre, El-Tahrir St, Dokki, Giza 12311, Egypt.
³ Department of Microbiology and Immunology, Texas Tech University Health Sciences Center, Lubbock, TX 79430, USA.
⁴ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA. Electronic address: Paul.Pare@ttu.edu.

PMID: 24735824
DOI: 10.1016/j.phytochem.2014.03.029

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 4β,5α-epoxy-7αH-germacr-10(14)-en-6β-ol-1-one, 4β,5α-epoxy-7αH-germacr-10(14)-en,1β-hydroperoxyl,6β-ol, 4β,5β-epoxy-7αH-germacr-10(14)-en,1β-hydroperoxyl,6β-ol and 4α,5β-epoxy-7αH-germacr-10(14)-en,1β-hydroperoxyl,6α-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, (1)H and (13)C NMR) data, as well as two-dimensional NMR ((1)H-(1)H COSY, HMQC, NOESY and HMBC), and ESI-MS analysis. The relative stereochemistry 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 μMol range. Diverse sesquiterpene-skeleton structure and corresponding comprehensive enzyme capacity is discussed.

Keywords: Biofilm blocking; Lamiaceae; Sesquiterpenes; Teucrium polium.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology*
Biofilms / drug effects*
Magnetic Resonance Spectroscopy
Molecular Structure
Sesquiterpenes / chemistry*
Sesquiterpenes / pharmacology*
Staphylococcus aureus / drug effects
Teucrium / chemistry*

Substances

Anti-Bacterial Agents
Sesquiterpenes