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

doi:10.1016/j.phytochem.2014.03.029

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 journal › Article › peer-review

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 language	English
Pages (from-to)	107-113
Number of pages	7
Journal	Phytochemistry
Volume	103
Early online date	12 Apr 2014
DOIs	https://doi.org/10.1016/j.phytochem.2014.03.029
Publication status	Published - 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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10.1016/j.phytochem.2014.03.029

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@article{50f8b7d8e8014cc598a25646e87ebc4b,

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 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. ",

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

author = "Elmasri, {Wael A.} and Hegazy, {Mohamed-Elamir F.} and Mina Aziz and Ekrem Koksal and Wail Amor and Yehia Mechref and Hamood, {Abdul N.} and Cordes, {David B.} and Pare, {Paul W.}",

note = "This research was supported in part by the Robert Welch Foundation (D-1478), NSF equipment grant CHE-1048553 and NSF CRIF program. We are grateful to and Tianjiao Yang for providing massspectral technical support. ",

year = "2014",

month = jul,

doi = "10.1016/j.phytochem.2014.03.029",

language = "English",

volume = "103",

pages = "107--113",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier",

}

TY - JOUR

T1 - Biofilm blocking sesquiterpenes from Teucrium polium

AU - Elmasri, Wael A.

AU - Hegazy, Mohamed-Elamir F.

AU - Aziz, Mina

AU - Koksal, Ekrem

AU - Amor, Wail

AU - Mechref, Yehia

AU - Hamood, Abdul N.

AU - Cordes, David B.

AU - Pare, Paul W.

N1 - This research was supported in part by the Robert Welch Foundation (D-1478), NSF equipment grant CHE-1048553 and NSF CRIF program. We are grateful to and Tianjiao Yang for providing massspectral technical support.

PY - 2014/7

Y1 - 2014/7

N2 - 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.

AB - 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.

KW - Teucrium polium

KW - Lamiaceae

KW - Sesquiterpenes

KW - Biofilm blocking

KW - Essential oil

KW - Antioxidant activity

KW - Cichorium-intybus

KW - Mass-spectrometry

KW - L.

KW - Biotransformation

KW - 7-EPI-eudesmanes

KW - Constituents

KW - Diterpenoids

KW - Glycosides

U2 - 10.1016/j.phytochem.2014.03.029

DO - 10.1016/j.phytochem.2014.03.029

M3 - Article

SN - 0031-9422

VL - 103

SP - 107

EP - 113

JO - Phytochemistry

JF - Phytochemistry

ER -

Biofilm blocking sesquiterpenes from Teucrium polium

Abstract

Keywords

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