From Echinacea angustifolia

Fig. 2.77 Compounds 246-249, caffeic-acid derivatives from Echinacea angustifolia. Compounds 250 and 251, sweet principals from Lippia dulcis...

Facino, R.M., Carini, M., Aldini, G., Marinello, C., Arlandini, E., Franzoi, L., Colombo, M., Pietta, P., and Mauri, P. 1993. Direct characterization of caffeoyl esters with antihyaluronidase activity in crude extracts from Echinacea angustifolia roots by fast atom bombardment tandem mass spectrometry. Farmaco 48, 1447-1461. 

Sun, L., Rezaei, K., Temelli, F., and Ooraikul, B. 2002. Supercritical fluid extraction of alkylamides from Echinacea angustifolia. J. Agric. Food Chem. 50, 3947-3953. 

In an in vitro study involving alkamides from Echinacea angustifolia and several Achillea species, 20 compounds tested were relatively potent inhibitors of cyclooxygenase, while a few also inhibited 5-lipoxygenase (Muller-Jakic et al. 1994). The two enzymes are involved in the metabolism of arachidonic acid, the major pathway to inflammation. Considering the structural similarities to arachidonic acid, the authors propose the alkamides act as analogues, competitively inhibiting the enzymes. 

Preparations from Echinacea angustifolia roots Chemical constituents and analysis Essential oil... 

HPLC separation of an alcoholic extract from Echinacea angustifolia roots with alkamides. From [4]. 

Jacobson M, Redfern RE, Mills GDjr (1975) Naturally occurring insect growth regulators. - III. Echinolone, a highly active juvenile hormone mimic from Echinacea angustifolia roots. Lloydia 38 473-476... 

Facino RM, Sparatore A, Carini M, Gioia B, Arlandini E, Franzoi L (1991) Field desorption mass spectrometry, fast atom bombardment mass spectrometry and fast atom bombardment tandem mass spectrometry of echinacoside, the main caffeoyl-glycoside from Echinacea angustifolia roots (Asteraceae). Org Mass Spectrom 26 951-955... 

Turner et al. (2005) evaluated the efficacy of Echinacea angustifolia in experimental rhinovirus infections. The results of this study indicate that extracts of E. angustifolia root, either alone or in combination, did not have clinically significant effects on the infection or on the clinical illness that results from it. Be that as it may, many believe in echinacea and used it routinely to avert the common cold. 

Bauer, R., Remiger, P., and Wagner, H. 1989. Alkamides from the roots of Echinacea angustifolia. Phytochemistry 28, 505-508. 

To date, only one study has evaluated the pharmacokinetics of the alkamides contained in the Echinacea products administered to humans (27). Subjects (n - 11) received a single oral 2.5-mL dose of the 60% ethanolic extract from E. angustifolia roots or placebo (60% ethanol). Six different alkamides were analyzed (1) Undeca-2D/Z-ene-8,10-diynoic acid isobutylamides (2) Dodeca-2D,4Z-diene-8,10-diynoic acidisobutylamide (3) Dodeca-2E-ene-8,10-diynoic acid isobutylamide (4) Dodeca-2E,4E,8Z,10E/ Z-tetraenoic acid isobutylamides (5) Dodeca-2E,4E,8Z-trienoic acid isobutylamide and (6) Dodeca-2E,4E-dienoic acid isobutylamide. The extract contained approx 2.5 mg of (4), and approx 0.5 mg of all other components. The Cmax and area under the curve (AUC) for (4) were approx 10-fold that achieved with each of the other components. Thus, despite a fivefold higher amount per dose, the 10-fold greater Cmax and AUC achieved with (4) suggest it exhibits a greater bioavailability than the other components. 

Woelkart K, Koidl C, Grisold A, et al. Bioavailability and pharmacokinetics of alkamides from the roots of Echinacea angustifolia in humans. J Clin Pharmacol 2005 45 683-689. 

Little, R. 1999. Taming Echinacea angustifolia research at SDSU and insights from a grower, http //www.abs.sdstate.edu/bio/reesen/Echinaca/newsletter.htm. 

In spite of its great difference from the structural features of natural juvenile hormones, ( )-4,10-dimethyl-10-hydroxy-4,1 l-dodecadien-2-one (32), isolated by Jacobson and Redfern (1974) from the root of Echinacea angustifolia, exhibited a strong morphogenetic action. 

In vitro studies on the effect of Echinacea purpurea on GYP enzymes have given mixed results. Results from one study on the effects of a preparation of the aerial parts of Echinacea purpurea on CYP3A4 differed according to the model substrate used one substrate (7-benzyloxy-4-trifluoromethyl-coumarin) indicated induction, while the other (resorufin benzyl ether) indicated inhibition (Yale and Gulrich 2005). Another study showed significant inhibition by a "commercial grade extract" (no other description provided) of Echinacea angustifolia root (Budzinski et al. 2000). 

Isol. from roots of Echinacea angustifolia and from Cistanche salsa. Needles (EtOH). [a] —56.5 (H2O). 

The roots of Echinacea angustifolia usually contain only ca. 0.1% essential oil [5, 14, 15]. Bischoff [16], who reported an essential oil content of 1.25-1.5%, must have used the roots of . pallida for his studies. The main components of the essential oil of . angustifolia are compounds such as dodeca-2,4-diene-l-yl-isovalerate, as well as palmitic and linoleic acids [14]. One other major constituent (44% of the oil) has been identified as pentadeca-l,8Z-diene, a minor one as 1-pentadecene [17]. A further volatile compound, ( )-10-hydroxy-4,10-dimethyl-4,ll-dodecadiene-2-one ( Echinolon ), published as a constituent of "Echinacea angustifolia roots [18], is probably from the adulterant . pallida. Pentadeca-8Z-en-2-one, already reported by Schulte et al. [19] as a major constituent of "Echinacea angustifolia"", is presumably derived from . pallida, since Heinzer et al. [14] found it as one of the main components only in the root oil of . pallida. It is also very probable that this compound is identical with the substance reported by Verelis [20] as geranyl-isobutyrate, because Heinzer et al. [14] failed to detect geranyl-isobutyrate... 

According to our present knowledge, the polyacetylenes published as constituents of Echinacea angustifolia roots [19, 22] are presumably derived from . pallida. It was shown by Heinzer et al. [14] that authentic Echinacea angustifolia contains only traces of pentadeca-8Z,llZ-dien-2-one, pentadeca-8Z,13Z-dien-ll-yn-2-one and tetradeca-8Z-en-ll,13-diyn-2-one which can be detected by GC (Fig. 1). 

Gas chromatograms of the essential oils from the roots of Echinacea angustifolia (a), E. pallida (b) and E. purpurea (c). From [14]. 

Stoll et al. [39] isolated echinacoside from the roots of Echinacea angustifolia. It is the major polar constituent and is present at a concentration of 0.3-1.7% [15, 31, 39-41]. It occurs in . pallida at a similar concentration and is therefore not suitable for the discrimination of these two species [42]. However, they can be distinguished by the occurrence of 1,3- and 1,5-O-dicaffeoyl-quinic acids (Fig. 3), which are only present in the roots of . angustifolia [31]. 

Heyl and Staley [34] reported an inulin content of 5.9% for the roots of Echinacea angustifolia, Bonadeo et al. [49] isolated a pseudocrystalline substance ( echinacina B ) from . angustifolia with weak anti-hyaluronidase activity. It was characterized as a polysaccharide mixture, consisting mainly of an acidic mucopolysaccharide. A raw polysaccharide fraction from . angustifolia roots was also isolated by Wagner et al. [50]. However, this has not yet been characterized in detail. 

Three randomized trials have been published which have investigated the effectiveness of the combination of Echinaceae angustifoliae and . pallidat radix with Bap-tisia Thuja [21-23]. Freitag and Stammwitz randomized 52 children with pertussis to receive either erythromycin only, erythromycin and the Echinacea combination orally, or erythromycin and the Echinacea combination injected intramuscularly [21]. The duration of the illness was significanly shorter in the group which received intramuscular injections in addition to antibiotic treatment, while there was no sign-ficant effect obtained from the oral application of the combination. 

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