Phytochemistry and constituents of Echinacea Purpurea.

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Phytochemistry and constituents of Echinacea Purpurea.:

Echinacea angustifolia Coneflower photo Content and Actions: GIycoside, echinacoside; echinacin; polysaccharides; polyacetylenes; essential oil, including humulene; caryophyllene; flavonoids. Antiseptic, antiviral, immune stimulant, alterative.
 Key Components of Echinacea Purpurea:Amides;antibiotic polyacetylenes; caffeic acid derivatives; flavonoids; glycosides; inulin; volatile oil; vitamins and minerals (especially chromium, iron, manganese, niacin, riboflavin, selenium, and vitamin C);
 Although each variety of Echinacea carries it's own unique phytochemical fingerprint, the classes of immunologically relevent compounds found in each are relatively consistent. There is some debate over which class of compounds is the most important in the medicinal effects of Echinacea. It is likely, however, that maximum benefit is derived from synergistic interactions between several compounds. The classes of compounds thought to contribute to the activity of Echinacea include approximately 20 different alkaloids3-5, polysaccharides6-10, and glycosides5 - in particular, the caffeic acid derivative echinacoside. Each of the nine different varieties of Echinacea have their own unique fingerprint of the various phytochemicals, in many cases lending differing activities to different species of the plant.

Chemistry

 Echinacea Purpurea Constituents picture Echinacea species contain a great variety of chemical components that contribute to their activity. Some of the constituents are unique to one species, while others occur in two or more of the commercially important species. Seven classes of secondary compounds are considered important to the therapeutic actions of Echinacea, and these have received the most intensive study (Bauer and Wagner, 1991).
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Phenolic Compounds

 Phenylpropanoids:
 Caffeic acid derivatives reported from Echinacea species include echinacoside, verbascoside, des-rhamnosylverbascoside and 6-O-caffeoylechinacoside, cynarin, cichoric acid, caftaric, chlorogenic and isochlorogenic acids, and others (Bauer and Wagner, 1991).

 Flavonoids:
 Rutoside is the major flavonoid found in the leaves of Echinacea angustifolia, E. pallida, and E. purpurea. In addition, the following flavonoids have been reported, and occur as both the aglycones and as conjugates with various sugars: luteolin, kaempferol, quercetin, quercetagetin, apigenin, isorhamnetin. The flavonoid content of the leaves, calculated as quercetin, has been estimated at 0.48% for E. purpurea and 0.38% for E. angustifolia (Bauer and Wagner, 1991).
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Terpenoid Compounds

 All 3 commercially important Echinacea species contain varying amounts of essential oils in the roots, leaves, flowers, and other aerial parts. Concentrations of total essential oil vary widely from species to species. Typical concentrations for fresh materials range from 0.05-0.48%, and in dried materials from less than 0.1% to 1.25%, depending on the plant part (Bauer and Wagner,1991).
 Essential oil components common to the 3 most investigated species (Echinacea angustifolia, E. pallida, and E. purpurea) include borneol, bornylacetate, pentadeca-8-ene-2-one, germacrene D, caryophyllene, caryophyllene epoxide, and palmitic acid. In addition to the above constituents, volatile components have been identified that are unique to each species (Bauer and Wagner, 1991).

Lipid Compounds

 Polyacetylenes:
 Polyacetylenes are widespread in the Asteraceae, and Shulte et al. (1967) determined the structures of 5 compounds in the series found in Echinacea. An additional 8 were partially elucidated. The main constituents were determined as trideca-1-en-3,5,7,9,10-pentayne and pontica-epoxide, present in Echinacea purpurea and E. angustifolia. The authors reported a total polyacetylene content of 2 mg% of the fresh roots and observed that the content decreases markedly during long-term storage of the ground root; 4 commercial samples of Echinacea preparations contained no detectable polyacetylenes.
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Nitrogenous Compounds

 Alkylamides:
 Natural alkylamides (or alkamides) are abundant in Echinacea species, as well as other members of the Compositae tribes, Anthemideae and Heliantheae. The first alkylamide isolated from Echinacea, echinacein (dodeca-(2E,6Z,8E,10E)-tetraenoic acid), was reported in the roots of E. angustifolia (0.01%) and E. pallida (0.001%). Numerous other alkylamides have since been identified by Bauer et al. (1989) in E. purpurea and E. angustifolia (Bauer, 1998). Determination of the major alkylamides showed that they accumulate primarily in the roots and inflorescences, with the highest content being found in the roots of E. angustifolia (0.009-0.15%); by contrast, E. pallida roots contain very low levels, and E. purpurea roots contain 0.004-0.039% (Bauer and Remiger, 1989). In a more extensive determination, Perry et al. (1997) found the major alkylamides in 1.5-year-old E. purpurea at highest levels (mean 14.1 mg/g) in the vegetative stems, with lesser amounts in the rhizome (mean 5.7 mg/g), flower (mean 2.7 mg/g), and root (mean 1.7 mg/g). The authors suggested that the higher levels of alkylamides in the New Zealand-grown samples of E. purpurea they examined, compared to earlier determinations of the species by Bauer and Remiger (1989), may owe to losses upon storage or differences in growing areas. Alkylamides are also present in other Echinacea species (Bauer and Remiger, 1989).
 Echinacea Purpurea photo Alkaloids:
 Early reports of an "alkaloid" in Echinacea species were subsequently shown to be due to the presence of betaine (Echinacea angustifolia) and/or glycine betaine (E. purpurea). Traces of the pyrrolizidine alkaloids (0.006% in dried materials) tussilagine and isotussilagine, were reported in both E. purpurea and E. angustifolia. According to structure/activity studies, a 1,2-unsaturated necine ring system is necessary for pyrrolizidine alkaloids to be hepatotoxic. Since neither of the pyrrolizidines from Echinacea have this structure, there is little risk of liver damage for consumers (Bauer and Wagner, 1991).

Carbohydrates

 Polysaccharides:
 Polysaccharides have been implicated as one of the primary classes of immunostimulatory compounds in Echinacea species. Two immunostimulatory polysaccharides, PS I and PS II, were isolated from the aerial parts of Echinacea purpurea. Structural studies revealed PS I to be a 4-O-methylglucuronoarabinoxylan with an average molecular weight (MW) of 35 kDa, while PS II is an acidic arabinorhamnogalactan of 50 kDa. A xyloglucan (79 kDa) was also isolated from the leaves and stems of E. purpurea. None of these are identical to a pectin-like polysaccharide, isolated from the expressed juice, which possessed only weak immunostimulatory activity (Bauer and Wagner, 1991). The immunostimulatory polysaccharides of Echinacea species can be produced in cell cultures of E. purpurea on an industrial scale (Bauer and Wagner, 1991).

 Echinacea also contain fructose and fructan polymers. Giger et al. (1989) reported that the total fructosan content of Echinacea purpurea increased during the winter, whereas this process occurred later in the season in E. angustifolia. The fructan content of the aerial parts of E. purpurea was 10 times less than that of the roots, and the leaves and stems of E. angustifolia contained practically none. Homeopathic tinctures were also found to contain fructans (Giger et al., 1989).
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Other constituents

 Echinacea Purpurea Coneflower picture Other constituents reported from Echinacea species include reducing sugars, phytosterols, a series of n-alkanes (see Essential oil) and inorganic constituents (potassium, calcium, magnesium, iron (III), aluminum, sulphate, carbonate, chloride, and silicate). Ascorbic acid has been found in the leaves of Echinacea purpurea (0.214% of dry weight). Sitosterol, myristic, and linoleic acid were detected in E. angustifolia. Cyanidin glycosides have been isolated from the flowers of E. purpurea and E. pallida. Three glycoproteins (MW 17, 21, and 30 kDa) were isolated from E. angustifolia (Bauer and Wagner, 1991).

 The sesquiterpene esters, echinadiol-, echinaxanthol-, and dihydroxynardol-cinnamate were originally described by Bauer et al. (1986) as constituents of Echinacea purpurea roots. These compounds are in fact derived from the adulterant, Parthenium integrifolium, which was mistakenly processed at the time when adulteration by this species was common in commercial Echinacea products (Bauer et al., 1987).
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Constituents and Echinacea species.

 Because of confusion in the literature due to misidentification of Echinacea spp. with Pathenium integrifolium only references used after 1986 are being used in this section:

 Echinacea angustifolia roots:
 polysaccharides (Inulin and fructose); phenylpropenoids (echinacoside, chicoric acid, cynarine and caffaric acid); alkamides ( complex of isobutylamide, the numbing taste); alkaloid (tussilagine 0.006%) and oils (0.1%, palmitic and linolenic acids).

 Echinacea Purpurea photo E. pallida roots:
 phenylpropenoids (echinacoside and chlorogenic acid); alkamides (trace amounts); polyacetylenes; oils (0.2 - 2.0% ketoalkenynes).

 E. purpurea root:
 polypropenoids (chichoric acid 0.6 - 2.1%); alkamides (complex of isobutylamides); alkaloid (tussilagine and isotussilagine); polysaccharide (fructose based) and oils (0.03 - 0.2%, caryphyllene, humulene, palmitic, linolenic acids and germacrene D.

 E. purpurea areal:
 polypropenoids (chichoric acid ); alkamides ( complex of isobutylamides); flavonoids (rutoside, quercitin, quercetin-7-glucoside and kaempferol-3-rutinoside and essential oils.

 It should be noted that the polysaccharides are not soluble in alcohol (Etol), polypropenoid soluble in medium strength Etol and Alkamides only in very strong Etol. The constituents desired in the final product will help determine if the product should be a powder (capsule or tablet), tea, or tincture.
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Reference:
  • 1.What is Echinacea Purpurea?Good function and application of Polyphenols and Chicoric acid from Echinacea Purpurea Extract?

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Available Product
  • Name:Echinacea Extract
  • Serie No:S-009.
  • Specifications:Polyphenols 4%UV;Chicoric Acid 2.0% HPLC;4:1TLC
  • INCI Name:ECHINACEA PURPUREA ROOT EXTRACT;ECHINACEA PURPUREA EXTRACT
  • EINECS/ELINCS No.:289-808-4
  • CAS:90028-20-9
  • Chem/IUPAC Name:Echinacea Purpurea Root Extract is an extract of the roots of Echinacea purpurea,Compositae.

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