Macrophage Activating Effects of New Alkamides from the Roots of Echinacea Species

Abstract

Chemical investigation of the roots of Echinacea angustifolia, E. purpurea, and E. pallida yielded two new alkamides, identified by analysis of spectroscopic data and comparison with reported alkamides. The new compounds were dodeca-2Z,4E,10Z-trien-8-ynoic acid isobutylamide (1) from E. angustifolia and dodeca-2Z,4E-diene-8,10-diynoic acid isobutylamide (2) from E. purpurea and E. pallida. These two components, as well as previously identified alkamides, exerted inhibition on LPS-mediated activation of a murine macrophage line, RAW264.7. These data suggest that these alkamides may have anti-inflammatory activity. The cytotoxicity of these alkamides using MTT assays was also investigated.

Echinacea Species and Alkamides Inhibit Prostaglandin E2 Production in RAW264.7 Mouse Macrophage Cells

“…The results presented in this study demonstrate the inhibition of PGE 2 by several Echinacea species, which may be one process contributing to the reported anti-inflammatory capabilities of these herbs (12). All Soxhlet EtOH extracts from the six species screened, when tested at their highest concentration, reduced PGE 2 levels, except E. purpurea.…”

“…A study performed by Chen et al (12) indicated that alkamides had anti-inflammatory activity as measured by inhibition of nitric oxide (NO) production in LPS-stimulated RAW264.7 cells. NO is a pro-inflammatory mediator that was significantly reduced by total alkamide (a mixture consisting of several alkamides) ranging from 1.6 to 30 µg/mL.…”

“…It was also important to determine whether specific alkamides play a clear role in the anti-inflammatory properties of six Echinacea species. To this end, we have conducted (to our knowledge) the first large-scale screen of nine synthesized alkamides found in Echinacea, three synthesized analogues, two of Bauer alkamide 12 (14) and one of Chen alkamide 2, and one synthesized isomer of Chen alkamide 1 (12) for their ability to reduce LPS-stimulated PGE 2 production. (PI 631250).…”

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

“…The recent discovery that dodecadiendiynoic amide 1 from E. purpurea and E. pallida inhibited LPS-mediated activation of a murine macrophage line, RAW264.7, suggests that this alkamide may have anti-inflammatory activity [7]. …”

Echinacea Inhibits Adenosine Deaminase Enzyme in Cancerous Human Gastric Tissue

“…Several classes of active constituents have been identified in Echinacea species including caffeic acid derivatives, alkylamides, polyacetylenes, and polysaccharides which are responsible for the anti-inflammatory, immunostimulatory, antioxidant and cicatrising activities of this plant [10]. Actually, the therapeutic use of Echinacea extracts is mostly for the prevention and treatment of upper respiratory tract infections and influenza symptoms [11][12][13]. Echinacea preparations are widely used remedies in Complementary and Alternative Medicine [14].…”