Diacetylenic isobutylamides of Echinacea: synthesis and natural distribution

Wu, Lankun; Bae, Jaehoon; Kraus, George A.; Wurtele, Eve Syrkin

doi:10.1016/j.phytochem.2004.06.027

Cited by 33 publications

(36 citation statements)

References 17 publications

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“…Bohlmann synthesized 1 and 5 in low overall yields, in part because the Wittig reactions that installed the cis-amide moiety produced the cis-isomers in only 13-14% yields [13]. Kraus and Bae have reported syntheses of amides 2 and 3 and ketone 4 [14,15]. We report herein the preparation of diacetylenic amides 1 and 5.…”

Section: Synthesis Of Alkamidesmentioning

confidence: 94%

“…Six-month-old roots, flowers and leaves from each species/accessions were used. Specific plant growth conditions, plant material harvest and extraction method are the same as those in our previously published work [15]. 7-Hydroxy-(E)-Nisobutylundeca-2-ene-8,10-diynamide (C 15 H 21 O 2 ) was added as an internal standard prior to extraction for quantification purposes.…”

Section: Plant Materials and Extractionmentioning

confidence: 99%

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Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Kraus

Bae

et al. 2006

Molecules

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Section: Synthesis Of Alkamidesmentioning

confidence: 94%

Section: Plant Materials and Extractionmentioning

confidence: 99%

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Kraus

Bae

et al. 2006

Molecules

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“…The identity of select alkamides was determined by running unknown extracts with individual synthesized alkamide standards (nos. 1, 2, 3, 4, 7, 8, 9, 10, and 11) provided by colleagues at Iowa State University (Kraus and Bae 2003;Wu et al 2004).…”

Section: Methodsmentioning

confidence: 99%

Alkamide production from hairy root cultures of Echinacea

Romero

Delate

Kraus

et al. 2009

In Vitro Cell.Dev.Biol.-Plant

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Hairy root cultures of Echinacea, one of the most important medicinal plants in the US, represent a valuable alternative to field cultivation for the production of bioactive secondary metabolites. In this study, the three most economically important species of Echinacea (Echinacea purpurea, Echinacea pallida, and Echinacea angustifolia) were readily transformed with two strains of Agrobacterium that produce the hairy root phenotype. Transformed roots of all three species exhibited consistent accelerated growth and increased levels of alkamide production. Optimization of the culture of Echinacea hairy roots was implemented to enhance both growth and alkamide production concomitantly. The use of halfstrength Gamborg's B5 medium supplemented with 3.0% sucrose was twice as effective in maintaining hairy root production than any other media tested. The addition of indolebutyric acid increased the growth rate of roots by as much as 14-fold. Alkamide production increased severalfold in response to the addition of the elicitor, jasmonic acid, but did not respond to the addition of indolebutyric acid. Induced accumulation of the important bioactive compounds, alkamides 2 and 8, was observed both in transformed roots and in response to jasmonic acid treatments. The results of this study demonstrate the efficacy of hairy root cultures of Echinacea for the in vitro production of alkamides and establish guidelines for optimum yield.

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“…The instrumentation and solvent system for HPLC separation were the same as those previously published (23). For compound identification, Bauer alkamides 8/9, cichoric acid, echinacoside, caftaric acid, and cynarin were purchased from Phytolab (Vestenbergsgreuth, Germany); chlorogenic acid was purchased from Sigma-Aldrich; and Bauer alkamides 2 and 10-14 and ketones 20-22 were synthesized (17,18). Peaks were identified according to retention time and mass spectra obtained from LC-MS and/or GC-MS.…”

Section: Plantmentioning

confidence: 99%

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

LaLone

Hammer

et al. 2007

J. Agric. Food Chem.

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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 μg/ mL from E. angustifolia, E. pallida, E. simulata, and E. sanguinea significantly inhibited PGE 2 production. In further studies, PGE 2 production was significantly reduced by all synthesized alkamides assayed at 50 μM, by Bauer alkamides 8, 12A analogue, and 14, Chen alkamide 2, and Chen alkamide 2 analogue at 25 μM and by Bauer alkamide 14 at 10 μM. Cytotoxicity did not play a role in the noted reduction of PGE 2 production in either the Echinacea extracts or synthesized alkamides. High-performance liquid chromatography analysis identified individual alkamides present at concentrations below 2.8 μM in the extracts from the six Echinacea species (15 μg/mL crude extract). Because active extracts contained 2, it is likely that alkamides may contribute toward the anti-inflammatory activity of Echinacea in a synergistic or additive manner.

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Diacetylenic isobutylamides of Echinacea: synthesis and natural distribution

Cited by 33 publications

References 17 publications

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Alkamide production from hairy root cultures of Echinacea

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

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Diacetylenic isobutylamides of Echinacea: synthesis and natural distribution

Cited by 33 publications

References 17 publications

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Alkamide production from hairy root cultures of Echinacea

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

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Product

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