Chapter

Echinacea

Chapter

Echinacea

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Abstract

Echinacea is one of the best-selling herbal preparations in many developed countries. Nowadays, the immunomodulatory effects of Echinacea are a prime concern for research, mainly linked to upper respiratory tract infections. Recent findings have also revealed that certain standardized preparations of Echinacea contain potent and selective antiviral, antifungal, antimicrobial, antiinflammatory, immunomodulatory, antitumor, antioxidant, mosquitocidal, and psychoactive activities, among others activities. Considering on the available, albeit limited, safety data, Echinacea appears to be well tolerated. Nevertheless, further investigation and surveillance are necessary to inaugurate the safety profiles of different Echinacea preparations. This chapter reviews the data for this medicinal plant on its source and availability, phytochemistry, morphological characteristics, health benefits, and possible interactions with drugs, foods, and other supplements.

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... EP has also been prepared for use as a topical treatment for skin and wound inflammation. In addition, Echinacea products are licensed in Europe to heal infections of the upper respiratory tract and wound healing [59][60][61][62]. The chemical components responsible for the immunomodulatory activities of purple coneflower roots are glycoproteins, alkylamides and polysaccharides [39]. ...
... EP has also been prepared for use as a topical treatment for skin and wound inflammation. In addition, Echinacea products are licensed in Europe to heal infections of the upper respiratory tract and wound healing [59][60][61][62]. ...
... Preparations containing EP are among the best-selling herbal medications in Europe and the United States [60,66]. EP supplementation may decrease the severity and duration of acute respiratory tract infections, according to current research; however, no studies have been identified using Echinacea to prevent or treat the SARS-CoV virus infection [67]. ...
Article
Full-text available
Echinacea purpurea (L.) Moench (EP)is a perennial herbaceous flowering plant, commonly known as purple coneflower and it belongs to the Asteraceae family. The Echinacea genus is originally from North America, in the United States, and its species are widely distributed throughout. There are nine different species of Echinacea, but only three of them are used as medicinal plants with wide therapeutic uses: Echinacea purpurea (L.) Moench, Echinacea pallida (Nutt.) Nutt. and Echinacea angustifolia DC. Several significant groups of bioactive compounds with pharmacological activities have been isolated from Echinacea species. Numerous beneficial effects have been demonstrated about these compounds. The immunomodulatory effect was initially demonstrated, but over time other effects have also been highlighted. The present review gives a comprehensive summary of the chemical constituents, bioactive compounds, biological effects and therapeutical uses of purple coneflower. Research shows that such a well-known and recognized species needs to be further studied to obtain efficient products with a guarantee of the safety.
Article
The Echinacea (coneflower) genus includes herbaceous flowering species mainly used for medicinal purposes, as well as the ornamental plants. Morphological similarities between Echinacea species often lead to their incorrect identification and characterization. Genome size and SCoT markers were used for identification and establishing the taxonomic relationships within Echinacea genus. The analysis of the nuclear DNA content indicated, that the majority of Echinacea species possessed intermediate genomes, and only E. pallida has a large genome size. 2C DNA content ranged from 14.31 pg/2C (E. simulata) to 28.59 pg/2C (E. pallida). Based on flow cytometric measurements (FCM) of the nuclear DNA content it was possible to distinguish three coneflower species, E. simulata, E. pallida and E. sanguinea, confirming validity of the method for initial species identification. Whereas, SCoT-PCR analysis enabled the identification of all studied accessions. Nine primers revealed polymorphism both between species, as well as varieties of E. angustifolia and E. paradoxa, demonstrating the usefulness of SCoT primers for genetic diversity studies in this genus. The phylogenetic analysis confirmed, that Echinacea species are closely related and within the investigated accessions two main phylogenetic groups exist, with one species (E. purpurea) being not clustered to any of the groups. Two methods, FCM and SCoT-PCR, can be successfully applied in identification and taxonomic relationship assessment, as well as in determination of the genetic diversity of Echinacea genus. Moreover, this is the first report on genome size that includes eight Echinacea accessions.
Chapter
In recent years, Echinacea preparations have developed into the best selling herbal immunostimulants. Most of the products are derived from either the aerial or the underground parts of Echinacea purpurea, and from the roots of E. angustifolia or E. pallida. The common products in Europe mainly represent expressed juice preparations or alcoholic tinctures. The different species and preparations can be clearly distinguished phytochemically by their typical constituents. The most relevant compounds for standardization are caffeic acid derivatives (cichoric acid, echinacoside), alkamides, polyacetylenes, and glycoproteins/polysaccharides. Pharmacological studies have shown that cichoric acid, alkamides, and glycoproteins/polysaccharides possess immunomodulatory activity. Therefore they might be considered as active principles and best suited for standardization purposes. Clinical effects have been demonstrated for the expressed juice of the aerial parts of Echinacea purpurea in the adjuvant therapy of relapsing infections of the respiratory and urinary tracts, as well as for alcoholic tinctures of E. pallida and E. purpurea roots as adjuvants in the therapy of common cold and flu.
Article
An analytical method based on gas chromatography-mass spectral (GC-MS) analysis was developed as a fast screening tool in order to verify the authenticity of extracts of roots from different species of Echinacea, namely E. angustifolia, E. pallida and E. purpurea. Various extraction methods, i.e. soxhlet extraction, supercritical fluid extraction and maceration with three different solvents, were applied and the extracts were analysed by GC-MS. The chromatograms were evaluated by multivariate data analysis, i.e. cluster analysis, principal component analysis and discriminant analysis, in order to reveal if a classification into the three main species of Echinacea was possible using the information obtained. GC-MS analysis of the extracts of Echinacea, together with multivariate data analysis, displayed substantial classification power since a good separation of the three different species was achieved. This analytical approach was not only suitable for classification but was also sufficiently robust such that no distortion of root samples by ageing occurred. © 1998 John Wiley & Sons, Ltd.
Article
A morphometric analysis was conducted of Echinacea Moench (Asteraceae) to measure variation between native populations for taxonomic purposes. Data were collected from living and herbarium specimens. From a matrix of 321 specimens by 74 characters, a pair-wise distance matrix was computed using Gower's coefficient. Cluster strategies were explored from the distance matrix. MODECLUS clustering separated the data into two clusters, and a flexible agglomerative clustering method separated the data into the same two clusters, which were broken into four sub-clusters. Canonical discriminant analysis gave significant support for the two- and the four-cluster solutions. Canonical discriminant analysis also showed support for eight smaller clusters identified using McGregor's 1968 classification. We recognize two subgenera and four species: Echinacea subg. Echinacea contains only E. purpurea; Echinacea subg. Pallida contains E. atrorubens, E. laevigata, and E. pallida. The revised varieties are as follows: E. atrorubens var. atrorubens, E. atrorubens var. neglecta, E. atrorubens var. paradoxa, E. pallida var. angustifolia, E. pallida var. pallida, E. pallida var. sanguinea, E. pallida var. simulata, and E. pallida var. tennesseensis. A cladistic analysis was done on the four species. In the most parsimonious solution, E. purpurea was basally divergent to a clade of the other three species (70% bootstrap value), and all four were distinguishable by at least one apomorphy. A key to Echinacea taxa is provided, which should be valuable given the pharmaceutical and horticultural importance of Echinacea. Communicating Editor: Paul Wilson
Article
The major flavonoid of the aerial parts of Echinacea angustifolia was found to be patuletin-3- O -rutinoside (1), rather than rutin (2), as reported previously. The related amount of patuletin-3- O -rutinoside is 5-8-times higher than that of rutin in the tested samples. Patuletin-3- O -rutinoside also existed in the aerial parts of E. purpurea and E. pallida, and the first complete NMR assignment of patuletin-3- O -rutinoside was made by using 2D NMR techniques. This is the first report of the occurrence of patuletin-3- O -rutinoside in Echinacea species.
Article
A new method is described combining solid-phase extraction (SPE) and reversed-phase high-performance liquid chromatography (RP-HPLC) for the isolation, purification as well as qualitative and quantitative determination of free phenolic acids in six Echinacea species. Plant extracts were purified and phenolic acids isolated on octadecyl and quaternary amine Bakerbond SPE columns; final eluates were analysed by RP-HPLC. Significant differences in the composition and amount of phenolic acids within Echinacea genus have been shown. The method can be used for quick screening analysis of the content of phenolic acids in plant material.
Article
The isolation and structure elucidation of 15 alkamides from the roots of Echinacea angustifolia is reported. In addition to several compounds previously found in E. purpurea the new undeca-2Z-en-8,10-diynoic acid isobutylamide, dodeca-2E-en-8,10-diynoic acid isobutylamide, undeca-2Z-en-8,10-diynoic acid 2-methylbutylamide, dodeca-2E-en-8,10-diynoic acid 2-methylbutylamide, hexadeca-2E,9Z-dien-12,14-diynoic acid isobutylamide and dodeca-2E,4Z,10Z-trien-8-ynoic acid isobutylamide were isolated. The isobutylamide of undeca-2E-en-8,10-diynoic acid was found for the first time in Echinacea species. All structures were established by UV, IR, NMR and mass spectroscopy.
Article
Echinacea preparations are traditionally used to treat upper respiratory infections and inflammations. No psychotropic effects of Echinacea have been reported so far, although some recently reported active constituents are behaviorally active. Prompted by these findings, the anxiolytic potential of five different Echinacea preparations was evaluated. Three of these decreased anxiety but two of them had a very narrow effective dose range. Only one extract decreased anxiety within a wide dose-range (3-8 mg/kg). Anxiolytic effects were consistently seen in three different tests of anxiety, the elevated plus-maze, social interaction and shock-induced social avoidance tests. No locomotor suppressant effects were seen at any dose. Noteworthy, the doses that showed anxiolytic effects in the present study were much lower than those used in the laboratory models of the traditional indications. Chlordiazepoxide robustly decreased anxiety-like behavior in all tests but suppressed locomotion at higher doses. Perceived and real risks of conventional medications increase the demand for alternative therapies, provided that these are safe and efficient. Earlier evidence shows that Echinacea preparations have an excellent safety profile, while our findings suggest for the first time that certain preparations have a considerable anxiolytic potential. Further research is required to identify factors that differentiate efficient and inefficient preparations.
Article
The anti-inflammatory activity of a polysaccharidic fraction (EPF) obtained from Echinacea angustifolia roots has been examined using the carrageenan paw oedema and the croton oil ear test. EPF (0.5 mg kg-1 i.v.) almost inhibited the carrageenan-induced oedema over 8 h and furthermore, EPF, topically applied, inhibited mouse ear oedema induced by croton oil. EPF also reduced the leukocytic infiltration of the croton oil dermatitis, evaluated both as peroxidase activity and histologically. After topical application EPF appears to be slightly inferior in potency to indomethacin. The results suggest that the anti-inflammatory activity of E. angustifolia resides in its polysaccharidic content.
Article
The roots of Echinacea angustifolia (fam. Compositae) were used to obtain an antiphlogistic, immunostimulating and skin repairing extract. On the basis of these potential actions, the extract is used in cosmetic preparations. The aim of this study was to evaluate the anti-inflammatory activity of the extract using different irritation tests. The irritation reaction was induced by application of 0.015 ml of 0.25% croton oil in water to the ears of mice. The raw extract (Echinacina B), topically applied, inhibited oedema both at the maximum (6 hr) and in the decreasing phase (18 hr), and this effect was directly proportional to the doses used. Echinacina B was found to be more potent than the positive control, benzidamine, a topical non-steroidal anti-inflammatory drug. In addition, the extract given iv 1 hr before injection of 0.05 ml of 1% carrageenan into the hind paws of rats inhibited oedema in the histaminic and in the later phases of the phlogistic process. These data show the qualitative value of irritation tests for studying the anti-inflammatory action of a natural plant extract.
Article
A constituent of the root oil of Echinacea angustifolia DC. and E. pallida (Nutt.) Britt. inhibitory to Walker carcinosarcoma 256 and P-388 lymphocytic leukemia was isolated and identified as (Z)-1,8-pentadecadiene (2). This compound occurs in these oils to the extent of approximately 44% and appears to be the first diene olefin reported to show in vivo antitumor activity. The corresponding trans isomer (16) is less active. Both isomers were synthesized.
Article
Echinacea purpurea, a plant originally used by native Americans to treat respiratory infections, was evaluated for its ability to stimulate the production of cytokines by normal human peripheral blood macrophages in vitro. Commercial preparations of echinacea fresh pressed juice and dried juice were tested at concentrations ranging from 10 micrograms/ml to 0.012 microgram/ml and compared to endotoxin stimulated and unstimulated controls. Cytokine production was measured by ELISA after 18 h of incubation for IL-1 and 36 and 72 h for TNF-alpha, IL-6, and IL-10. Macrophages cultured in concentrations of echinacea as low as 0.012 microgram/ml produced significantly higher levels of IL-1, TNF-alpha, IL-6 and IL-10 (P < 0.05) than unstimulated cells. The high levels of IL-1, TNF-alpha, and IL-10 induced by very low levels of echinacea are consistent with an immune activated antiviral effect. Echinacea induced lower levels of IL-6 in comparison to the other cytokines measured. These results demonstrate the immune stimulatory ability of the unpurified fresh pressed juice of Echinacea purpurea and offer some insight into the nature of the resulting immune response as compared to endotoxin.
Article
This study demonstrated that plant extracts containing acetylenic isobutylamides and polyacetylenes, previously reported as occurring in Echinacea, have phototoxic antimicrobial activity against fungi, including clinically relevant pathogenic fungi. Results show that hexane extracts of Echinacea variably inhibit growth of yeast strains of Saccharomyces cerevisiae, Candida shehata, C. kefyr, C. albicans, C. steatulytica and C. tropicalis under near UV irradiation (phototoxicity) and to a lower extent without irradiation (conventional antifungal activity). The presence of polyacetylenes and alkylamides in extracts of different organs was confirmed in Echinacea purpurea by HPLC in agreement with previously reported data in the literature, and was related to phototoxic activity. Two representative pure compounds, undeca-2E,4Z-diene-8,10-diynoic acid isobutylamide and dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide, were isolated from Echinacea purpurea root extracts, and compared in a disk assay (5 micrograms/disk) with the highly conjugated trideca-1-ene-3,5,7,9,10-pentayne (previously isolated in our laboratory and found here in E. purpurea). Significant phototoxicity was demonstrated by pure trideca-1-ene-3,5,7,9,10-pentayne, while only minor phototoxicity was induced by the other two acetylenic compounds. Phototoxic activity of Echinacea spp. is primarily attributed to the ketoalkenes and ketoalkynes abundantly present in the roots.
Article
Alcoholic extracts of the roots and leaves of three Echinacea species (E. purpurea, E. angustifolia and E. pallida) were analysed for the presence of characteristic chemicals by HPLC directly coupled to ultraviolet absorbance and electrospray mass spectrometric detectors. The method permitted rapid characterization and tentative identification of a large number of caffeoyl conjugates and alkamides in all the samples investigated. The roots of the three species differed markedly in their contents of characteristic compounds. Cichoric acid and verbascoside predominated in extracts of E. purpurea root whereas cynarine and dodeca-2E,4E,8Z,10Z/E-tetraenoic acid isobutylamide were the major chemicals characteristic of E. angustifolia root extracts. Echinacoside and 6-O-caffeoylechinacoside predominated in extracts of E. pallida roots. Characteristic alkamides were also examined by electrospray tandem mass spectrometry (MS/MS) and these compounds provided characteristic fragmentation patterns. Extracts of the roots and leaves of all three species were found to have antioxidant properties in a free radical scavenging assay and in a lipid peroxidation assay.
Article
Alkamides from the roots of Echinacea purpurea (L.) Moench were examined for anti-inflammatory activity in an in vitro model system. Cyclooxygenase-I (COX-I) and cyclooxygenase-II (COX-II) inhibitory activities were assessed at pH 7 for alkamides isolated from E. purpurea roots to compare inhibitory activities between the two cyclooxygenase isozymes. At 100 microg/ml, several E. purpurea alkamides inhibited COX-I and COX-II enzymes in the range of 36-60% and 15-46%, respectively, as compared to controls. Mosquitocidal activity was assessed at 100 and 10 microg/ml, with 100% mortality against Aedes aegyptii L. larvae noted for several E. purpurea alkamides at 100 microg/ml.
Article
Extracts of 8 taxa of the genus Echinacea were found to have antiviral activity against Herpes simplex (HSV) virus Type I in vitro when exposed to visible and UV-A light. n-Hexane extracts of roots containing alkenes and amides were more active in general than ethyl acetate extracts containing caffeic acids. The most potent inhibitors of HSV were E. pallida var. sanguinea crude (70 % ethanol) inflorescence extract (MIC = 0.026 mg/mL), cichoric acid (MIC = 0.045 mg/mL) and Echinacea purpurea n-hexane root extract (MIC = 0.12 mg/mL).
Article
Preparations from Echinacea purpurea are among the most widely used herbal medicines. Most uses of E. purpurea are based on the reported immunological properties. A series of experiments have demonstrated that E. purpurea extracts do indeed demonstrate significant immunomodulatory activities. Among the many pharmacological properties reported, macrophage activation has been demonstrated most convincingly. Phagocytotic indices and macrophage-derived cytokine concentrations have been shown to be Echinacea-responsive in a variety of assays. Activation of polymorphonuclear leukocytes and natural killer cells has also been reasonably demonstrated. Changes in the numbers and activities of T- and B-cell leukocytes have been reported, but are less certain. Despite this cellular evidence of immunostimulation, pathways leading to enhanced resistance to infectious disease have not been described adequately. Several dozen human experiments--including a number of blind randomized trials--have reported health benefits. The most robust data come from trials testing E. purpurea extracts in the treatment for acute upper respiratory infection. Although suggestive of modest benefit, these trials are limited both in size and in methodological quality. Hence, while there is a great deal of moderately good-quality scientific data regarding E. purpurea, effectiveness in treating illness or in enhancing human health has not yet been proven beyond a reasonable doubt.
Article
Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system--the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found in ethanolic liquid extracts. To investigate the absorption of these two groups of compounds using Caco-2 monolayers, which are a model of the intestinal epithelial barrier. The caffeic acid conjugates (caftaric acid, echinacoside and cichoric acid) permeated poorly through the Caco-2 monolayers although one potential metabolite, cinnamic acid, diffused readily with an apparent permeability (Papp) of 1 x 10(-4) cm/s. Alkylamides were found to diffuse through Caco-2 monolayers with Papp ranging from 3 x 10(-6) to 3 x 10(-4) cm/s. This diversity in Papp for the different alkylamides correlates to structural variations, with saturation and N-terminal methylation contributing to decreases in Papp. The transport of the alkylamides is not affected by the presence of other constituents and the results for synthetic alkylamides were in line with those for the alkylamides in the echinacea preparation. Alkylamides but not caffeic acid conjugates are likely to cross the intestinal barrier.
Article
The distribution pattern of caffeic acid derivatives in Echinacea species is complex, and problems with the identity of each drug have been recognized. Micellar electrokinetic chromatography (MEKC) has been applied to define the fingerprints of Echinacea angustifolia, Echinacea pallida, and Echinacea purpurea, and their mixtures. The results obtained evidence that MEKC is a valuable tool for the characterization of these drugs.
Article
The roots of ECHINACEA PALLIDA are characterized by TLC and HPLC fingerprints of the polyacetylenes, polyenes, and the caffeic acid derivatives. The fingerprints can also be used for the differentiation between E. PALLIDA and E. ANGUSTIFOLIA root extracts. The main constituents of E. PALLIDA roots are tetradeca-8 Z-ene-11,13-diyn-2-one ( 2), pentadeca-8 Z-ene-11,13-diyn-2-one ( 3), pentadeca-8 Z,13 Z-dien-11-yn-2-one ( 4), pentadeca-8 Z,11 Z,13 E-trien-2-one ( 5), pentadeca-8 Z,11 E,13 Z-trien-2-one ( 6), pentadeca-8 Z,11 Z-dien-2-one ( 7), and echinacoside ( 13). E. ANGUSTIFOLIA is usually void of these polyacetylenes and polyenes and is characterized by isobutylamides, echinacoside, and cynarine. The polyacetylenes of E. PALLIDA are very susceptible to autoxidation to the 8-hydroxy-9-ene derivatives. Thus, the chemical composition of the roots depends on the storage conditions.
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