Biofilm blocking sesquiterpenes from Teucrium polium

Elmasri, Wael A.; Hegazy, Mohamed‐Elamir F.; Aziz, Mina; Köksal, Ekrem; Amor, Wail; Mechref, Yehia; Hamood, Abdul N.; Cordes, David B.; Paré, Paul W.

doi:10.1016/j.phytochem.2014.03.029

Cited by 42 publications

(42 citation statements)

References 38 publications

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“…Moreover, these data revealed that 2 is similar to 1 except for an absence of the monosaccharide attached to position C‐5 of the basic skeleton; the presence of a methoxy group in 2 is supported by ion peaks at m/z 195, 155 and 127. In combination with previous NMR analyses of 7,8‐cyclopentene‐type IGs for stereochemical determination, the structure of 2 was assigned as teuhircoside; (1 S )‐5 α ‐methoxy‐1‐( β ‐D‐glucopyranosyloxy)‐5,9 α ‐dihydro‐8‐methylcyclopenta[c]pyran‐5(1 H )‐one.…”

Section: Resultsmentioning

confidence: 88%

“…Diagnostic MS/MS fragments allowed for the identification of IG components as well as plausible sugar‐iridoid linkages. In combination with previous NMR analyses of 7,8‐cyclopentene‐type IGs for stereochemical determination, 1 was assigned as teucardoside; (1 S )‐5 α ‐[(6‐deoxy‐ α ‐L‐mannopyranosyl)oxy]‐1‐( β ‐D‐glucopyranosyloxy)‐5,9 α ‐dihydro‐8‐methylcyclopenta[c]pyran‐5(1 H )‐one.…”

Section: Resultsmentioning

confidence: 90%

“…(c)). In combination with previous NMR analyses of 7,8‐cyclopentene‐type IGs for stereochemical determination, 3 was assigned as 1 α ‐( β ‐D‐glucopyranoxy)‐7 α ,8 α ‐epoxy‐5 β ,6 α ‐dihydroxy‐8‐methyl‐1,5,6,7,8,9 β ‐hexahydrocyclopenta[ c ]pyran.…”

Section: Resultsmentioning

confidence: 93%

“…Based on the fragmentation pattern and previously reported NMR data, 4 is similar to 1 except for a dihydropyran unit opening at an ether linkage and unsaturation of the C9–C1 bond. In combination with previous NMR analyses of 7,8‐cyclopentene‐type IGs for stereochemical determination, 4 was assigned as 1 α ‐( β ‐D‐glucopyranoxy)‐7 α ,8 α ‐epoxy‐5 β ,6 α ‐dihydroxy‐8‐methyl‐1,5,6,7,8,9 β ‐hexahydrocyclopenta[ c ]pyran.…”

Section: Resultsmentioning

confidence: 93%

“…Teucrium polium, a member of the Lamiaceae family, is a traditional medicinal herbal with solvent extracts exhibiting antibacterial and antitumor activity . In addition to the expected chemical profile of flavonoids and phenylpropanoid glycosides, aerial portions of the plant contain a less common class of compounds called iridoid glycosides (IGs) . The name originates from the ant genus Iridomyrmex , from which the original iridoid structure was identified .…”

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confidence: 99%

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Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization

Elmasri

Yang

Hegazy

et al. 2016

Rapid Comm Mass Spectrometry

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RATIONALE While natural products isolated from medicinal plants can serve as a rich source of biologically active metabolites, mixtures of structurally related compounds of a polar nature are often difficult to chemically resolve by traditional separation techniques. Chemical derivatization to reduce metabolite polarity combined with liquid chromatography is the strategy presented here to resolve a mixture of structurally related natural product glycosides solvent extracted from the medicinal herb Teucrium polium for mass spectroscopy characterization. METHODS The partially-purified plant extract was chemical derivatization and electrospray ionization mass spectrometry (ESI-MS) fragmentation-pattern analysis allowed for structural characterization of iridoid and secoiridoid glycosides. Select ions were subjected to tandem MS analysis with a relatively higher-energy collision dissociation to assist in structural elucidation. RESULTS Permethylation replaced all protons from free hydroxyl and amino groups with methyls and resulted in increases in both hydrophobicity, for facilitated chromatographic separation, and proton affinity, for enhanced chemical ionization. Protonated and/or sodiated adducts were observed for the six compounds detected in positive ion mode ESI-MS with a mass accuracy of less than 2 ppm. CONCLUSIONS Permethylation combined with LC-MS analysis is shown here to be an effective chemical practice for separating and characterizing iridoid glucosinolates and is expected to be well suited for the chemical characterization of other polar natural-product mixtures of closely related compounds.

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 93%

mentioning

confidence: 99%

See 3 more Smart Citations

Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization

Elmasri

Yang

Hegazy

et al. 2016

Rapid Comm Mass Spectrometry

Self Cite

View full text Add to dashboard Cite

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Therapeutics studies and biological properties of Teucrium polium (Lamiaceae)

2021

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Teucrium polium has been used in traditional medicine as antifungal, antipyretic, antispasmodic, and antibacterial. It is consumed by many jordanians for the treatment of many diseases. The effects of this plant have been investigated in kidney, liver, and brain. Its antidiabetic, antimicrobial, antioxidant, and anticancer effects have been introduced. Polyphenolic compound, flavonoids, monoterpenes, alkanoides, and essential oils were identified. Several studies revealed that this plant has a hypoglycemic effect and can help to control blood sugar. It was reported that plants containing flavonoids and phenolics compounds exhibit a large array of biological activities like genotoxicity (chromosomal aberrations and sister chromatid exchange) and oxidative stress damage. These phytochemicals are found in herbal and vegetables plants, as well as being reliably protective against oxidative stress damage and lipid peroxidation. In addition, T. polium has secondary effects on different organs, namely liver, kidney and at high doses this plant becomes toxic. In conclusion, this review investigates many pharmacologicals properties and side effects of T. polium.

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Antibacterial and Antifungal Activity of Secondary Metabolites of Teucrium Species

Stefanović

2020

Teucrium Species: Biology and Applications

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Biofilm blocking sesquiterpenes from Teucrium polium

Cited by 42 publications

References 38 publications

Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization

Iridoid glycoside permethylation enhances chromatographic separation and chemical ionization

Therapeutics studies and biological properties of Teucrium polium (Lamiaceae)

Antibacterial and Antifungal Activity of Secondary Metabolites of Teucrium Species

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