LC–MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol

Boonen, Jente; Baert, Bram; Burvenich, Christian; Blondeel, Phillip; Saeger, Sarah De; Spiegeleer, Bart De

doi:10.1016/j.jpba.2010.02.010

Cited by 92 publications

(89 citation statements)

References 16 publications

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“…Furthermore, the interaction of eight Echinacea alkamides with P-glycoprotein, a major constituent of the blood-brain barrier, showed that four derivatives inhibited P-glycoprotein in primary endothelial cells freshly isolated from porcine brain blood vessels . The transdermal permeation behavior of spilanthol (92a) from Acmella paniculata (=Spilanthes acmella) extracts was investigated by Boonen et al (2010a, b), who reported on the influence of ethanol (65 %) and propylene glycol (10 %) as solvents. Similar permeation properties were recently also described for the Anacyclus pyrethrum extract and the main alkamide pellitorine (101a) (Veryser et al 2014).…”

Section: Pharmacokinetics and Bioavailabilitymentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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Alkamides are natural products formed by connecting straight-chain, mostly unsaturated, aliphatic acids with various amines by an amide linkage. More than 300 derivatives are known from eight plant families consisting of various combinations of 200 acids with 23 amines. Apart from a few saturated derivatives alkamides with unsaturated acid parts are grouped into compounds with purely olefinic patterns and those with olefinic and acetylenic linkages. Derived from C 18 oleic acid the acid parts are modified either by chain elongations to C 28 or by oxidative shortenings to C 4 acid residues. Substrate and regiospecific desaturases and acetylenases are responsible for their characteristic patterns of unsaturation. Amine parts are derived from various amino acids by decarboxylation. Beside the widespread isobutylamines alkamides with six-and five-membered ring amines and those with phenylalanine derived amines are characteristic for the Asteraceae and Piperaceae while benzylamines are restricted to the Brassicaceae. Within the Asteraceae 2-methylbutylamine distinguishes the tribe Heliantheae from Anthemideae characterized by ring amines. Alkamides with elongated olefinic acid parts are mainly found in Piperaceae and Brassicaceae while acetylenic acid parts are typical for Asteraceae. A wide variety of biological activities ranges from the characteristic pungent/ tingling property and high insecticidal toxicity to significant antifungal, antibacterial, antiprotozoal, molluscicidal, cercaricidal, and acaricidal activity. They also act as plant growth-promoting substances. Position and stereochemistry of the double bonds are essential for the different qualities of the pungent taste. Medically alkamides possess anti-inflammatory and analgesic properties and are responsible for immunomodulatory and cannabinomimetic effects.

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Section: Pharmacokinetics and Bioavailabilitymentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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“…The N-alkylamides, a natural group of secondary metabolites found in different genera of plants (Echinacea, Zanthoxylum, Heliopsis andSpilanthes), are new and promising bioactive molecules (BOONEN et al, 2010a). The principle or metabolite that is considered more active in SpilanthesoleraceaL.…”

Section: Chemical Composition Of the Plantmentioning

confidence: 99%

Jambu drying with cold air circulation

et al. 2015

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“…Generally, coupling the sensitivity and specificity of the mass spectrometer with the effective separation of LC can obtain online qualitative profile of phytochemicals in botanical extracts [133][134][135][136][137][138][139][140][141]. In some cases, LC-MS/MS methods are also used for profiling of bioactive components in herbs on a LTQ Orbitrap instrument [142,143].…”

Section: Miscellaneous Compoundsmentioning

confidence: 99%

Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography–mass spectrometry

Guo

Chen

et al. 2013

Journal of Pharmaceutical and Biomedical Analysis

166

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LC–MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol

Cited by 92 publications

References 16 publications

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Jambu drying with cold air circulation

Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography–mass spectrometry

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