The Synthesis and Natural Distribution of the Major Ketone Constituents in Echinacea pallida

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

doi:10.3390/12030406

Cited by 9 publications

(6 citation statements)

References 18 publications

(19 reference statements)

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“…The purified glycoproteins (arabinogalactans, fructofuranosides and heteroxylans), as well as alkylamides, especially isobutylamides and ketones (only in EPAL), in Echinacea plants appear to play important roles on phagocytic stimulation (Classen et al, 2006;Kraus et al, 2007). The supplementation of arabinogalactan-protein from an EPAL extract has been seen to increase the production of IL-6 and nitrite, which are by-products of activated macrophages (Classen et al, 2006).…”

Section: Blood Parameters and Immunological Testmentioning

confidence: 99%

Rabbit dietary supplementation with pale purple coneflower. 2. Effects on the performances, bacterial community, blood parameters and immunity of growing rabbits

Kovitvadhi

Gai

Dabbou

et al. 2016

Animal

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Echinacea pallida (EPAL), a herbaceous flowering plant with immunomodulatory properties, has been chosen to determine the pre-and post-supplementary effects on the growth performances, bacterial community, blood parameters and immunity of growing rabbits. The same Grimaud does (14-week-old) from the studied in the first part of this study were randomly divided into two groups (n = 50/group). The first group was fed a basal diet without supplementation (Control group, C) while the another group was fed a basal diet supplemented with 3 g EPAL/kg diet (Echinacea group, E). From the second parturition, 80 weaned kits (40 from the C does and 40 from the E does) were randomly assigned to four groups of 20 animals each and were fed a growing commercial diet supplemented with or without a 3 g EPAL/kg diet: the CC group (rabbits from the C does fed the control diet), CE group (rabbits from the C does fed the supplemented diet), EC (rabbits from the E does fed the control diet) and EE group (rabbits from the E does fed the supplemented diet). The dietary EPAL treatment did not affect the growth performance. Ten fattening rabbits from each group were selected to evaluate the bacterial community and blood parameters, while the remaining rabbits (n = 10/group) were used to study phagocytosis and the humoral immune response. The variability was evaluated from hard faeces at 35, 49 and 89 days, and the caecal content at 89 days. The variability of the bacterial community of the EE group was higher than that of the other groups. The phagocytic activity was higher in the CE and EE groups than in the CC and EC ones (30.9 and 29.7 v. 21.2 and 21.8%; P < 0.05), whereas no statistically significant difference was observed for the blood parameters or humoral immune response against vaccination (rabbit haemorrhagic disease virus) at 95 days old which the serum was collected at 88, 102, 109, 116 and 123 days old. In conclusion, no impact of EPAL dietary supplementation has been observed on the growth performances, bacterial community, blood parameters or humoral immune responses in growing rabbits, except for an increase in phagocytic activities.

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Section: Blood Parameters and Immunological Testmentioning

confidence: 99%

Rabbit dietary supplementation with pale purple coneflower. 2. Effects on the performances, bacterial community, blood parameters and immunity of growing rabbits

Kovitvadhi

Gai

Dabbou

et al. 2016

Animal

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“…We used as standards authentic alkamides and ketones that were purchased or synthesized by our group [17], [18], [19], as well as structural information obtained by a combination of HPLC-PDA and GC-MS, for more comprehensive compound identification. Because we lacked reference standards for many of the metabolites reported in this study (43 in all), we used relative instead of absolute metabolite concentrations to compare overall lipophilic-metabolite profiles across the 40 accessions.…”

Section: Introductionmentioning

confidence: 99%

Metabolic Profiling ofEchinaceaGenotypes and a Test of Alternative Taxonomic Treatments

Wu¹,

Dixon²,

Nikolau³

et al. 2008

Planta Med

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The genus Echinacea is used as an herbal medicine to treat a variety of ailments. To better understand its potential chemical variation, 40 Echinacea accessions encompassing broad geographical and morphological diversity were evaluated under controlled conditions. Metabolites of roots from these accessions were analyzed by HPLC-photo diode array (HPLC-PDA), GC-MS, and multivariate statistical methods. In total, 43 lipophilic metabolites, including 24 unknown compounds, were detected. Weighted principal component analysis (WPCA) and clustering analysis of the levels of these metabolites across Echinacea accessions, based on Canberra distances, allowed us to test two alternative taxonomic treatments of the genus, with the further goal of facilitating accession identification. A widely used system developed by McGregor based primarily on morphological features was more congruent with the dendrogram generated from the lipophilic metabolite data than the system more recently developed by Binns et al. Our data support the hypothesis that Echinacea pallida is a diverse allopolyploid, incorporating the genomes of Echinacea simulata and another taxon, possibly Echinacea sanguinea. Finally, most recognized taxa of Echinacea can be identified by their distinct lipophilic metabolite fingerprints.

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“…The syntheses of monoalkene 1 and bisacetylenes 2 and 3 have recently been reported by Dickschat et al [13] and Kraus et al [14,15] Despite the large interest in obtaining synthetic samples of the remaining unsaturated compounds for biological evaluation the other ketoalkenes have not been prepared so far. We therefore planned to synthesize the polyenes 5--8 and test their activity at the human cannabinoid receptors in a functional GTPase assay.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cannabinoid Receptor Activity of Ketoalkenes from Echinacea pallida and Nonnatural Analogues

Egger

Pellett

Nickl

et al. 2008

Chemistry A European J

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Despite its popularity and widespread use, the efficacy of Echinacea products remains unclear and controversial. Among the various compounds isolated from Echinacea, ketoalkenes and ketoalkenynes exclusively found in the pale purple coneflower (E. pallida) are major components of the extracts. In contrast to E. purpurea alkamides, these compounds have not been synthesized and studied for immunostimulatory effects. We present a practical and useful synthetic approach to the ketoalkenes using palladium-catalyzed cross-coupling reactions and the pharmaceutical results at the human cannabinoid receptors. The synthetic route developed provides overall good yields for the ketoalkenes and is applicable to other natural products with similar 1,4-diene motifs. No significant activity was observed at either receptor, indicating that the ketoalkenes from E. pallida are not responsible for immunomodulatory effects mediated via the cannabinergic system. However, newly synthesized non-natural analogues showed micro-molar potency at both cannabinoid receptors.

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The Synthesis and Natural Distribution of the Major Ketone Constituents in Echinacea pallida

Abstract: Abstract:The first synthesis of a series of ketones naturally occurring in E. pallida is described. The natural distribution of these ketones among different Echinacea species is also reported.

Cited by 9 publications

References 18 publications

Rabbit dietary supplementation with pale purple coneflower. 2. Effects on the performances, bacterial community, blood parameters and immunity of growing rabbits

Rabbit dietary supplementation with pale purple coneflower. 2. Effects on the performances, bacterial community, blood parameters and immunity of growing rabbits

Metabolic Profiling ofEchinaceaGenotypes and a Test of Alternative Taxonomic Treatments

Synthesis and Cannabinoid Receptor Activity of Ketoalkenes from Echinacea pallida and Nonnatural Analogues

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