Synthesis and natural distribution of anti-inflammatory alkamides from Echinacea.
نویسندگان
چکیده
The synthesis of the alkamides 2Z,4E-undeca-2,4-dien-8,10-diynoic acid isobutyl amide (1) and 2Z,4E-undeca-2,4-dien-8,10-diynoic acid isobutyl amide (5) was accomplished by organometallic coupling followed by introduction of the doubly unsaturated amide moiety. The distribution of these two amides in accessions of the nine species of Echinacea was determined.
منابع مشابه
Echinacea species and alkamides inhibit prostaglandin E(2) production in RAW264.7 mouse macrophage cells.
Inhibition of prostaglandin E(2) (PGE(2)) production in lipopolysaccharide-stimulated RAW264.7 mouse macrophage cells was assessed with an enzyme immunoassay following treatments with Echinacea extracts or synthesized alkamides. Results indicated that ethanol extracts diluted in media to a concentration of 15 microg/mL from E. angustifolia, E. pallida, E. simulata, and E. sanguinea significantl...
متن کاملEchinacea sanguinea and Echinacea pallida extracts stimulate glucuronidation and basolateral transfer of Bauer alkamides 8 and 10 and ketone 24 and inhibit P-glycoprotein transporter in Caco-2 cells.
The use of Echinacea as a medicinal herb is prominent in the United States, and many studies have assessed the effectiveness of Echinacea as an immunomodulator. We hypothesized that Bauer alkamides 8, 10, and 11 and ketone 24 were absorbed similarly either as pure compounds or from Echinacea sanguinea and Echinacea pallida ethanol extracts, and that these Echinacea extracts could inhibit the P-...
متن کاملThe role of alkamides as an active principle of echinacea.
Alkamides are the major lipophilic constituents of ECHINACEA preparations, which are widely used in some European countries and in North America for common colds. In earlier investigations they have been shown to possess stimulatory effects on phagocytosis. Recent experiments have demonstrated that alkamides are detectable in human blood in relevant concentrations after oral administration of E...
متن کاملEchinacea increases arginase activity and has anti-inflammatory properties in RAW 264.7 macrophage cells, indicative of alternative macrophage activation.
ETHNOPHARMACOLOGICAL RELEVANCE The genus Echinacea is a popular herbal immunomodulator. Recent reports indicate that Echinacea products inhibit nitric oxide (NO) production in activated macrophages. AIM OF THE STUDY In the present study we determined the inhibitory effects of alcohol extracts and individual fractions of alcohol extracts of Echinacea on NO production, and explored the mechanis...
متن کاملBioavailability of dodeca-2E, 4E, 8E, 10E/Z-tetraenoic acid isobutylamides after oral administration in rats and distribution in various tissues
Background Preparations from Echinacea are among the best-selling phytopharmaceuticals worldwide and have been widely used for the treatment of common cold and various upper respiratory infections. The most relevant active principles of Echinacea extracts are alkamides, caffeic acid derivatives (CADs) and glycoproteins/polysaccharides [1]. The main alkamides in Echinacea preparations are the is...
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ورودعنوان ژورنال:
- Molecules
دوره 11 10 شماره
صفحات -
تاریخ انتشار 2006