title: Biofilm blocking sesquiterpenes from Teucrium polium.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Wael A
authors.initials: WA
authors.lastname: Elmasri
authors.affiliation: Chemistry of Medicinal Plants/Center Excellence Science, National Research Centre, El-Tahrir St, Dokki, Giza 12311, Egypt.
authors.forename: Mohamed-Elamir F
authors.initials: MF
authors.lastname: Hegazy
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Mina
authors.initials: M
authors.lastname: Aziz
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Ekrem
authors.initials: E
authors.lastname: Koksal
authors.affiliation: Department of Microbiology and Immunology, Texas Tech University Health Sciences Center, Lubbock, TX 79430, USA.
authors.forename: Wail
authors.initials: W
authors.lastname: Amor
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Yehia
authors.initials: Y
authors.lastname: Mechref
authors.affiliation: Department of Microbiology and Immunology, Texas Tech University Health Sciences Center, Lubbock, TX 79430, USA.
authors.forename: Abdul N
authors.initials: AN
authors.lastname: Hamood
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA. Electronic address: Paul.Pare@ttu.edu.
authors.forename: Paul W
authors.initials: PW
authors.lastname: Paré
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D031367:Teucrium / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D012717:Sesquiterpenes
keywords: Biofilm blocking; Lamiaceae; Sesquiterpenes; Teucrium polium