Zur struktur der “agaricolsäure”

Schulte, K. E.; Rüċker, G.; Fachmann, Hans-Jürgen

doi:10.1016/s0040-4039(01)89611-8

Cited by 8 publications

(4 citation statements)

References 2 publications

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“…About 15 alkamides have been identified as major lipophilic constituents of E. angustifolia roots (40)(41)(42). They are mainly derived from undeca-and dodecanoic acid, and differ in the degree of unsaturation and the configuration of the double bonds ( Figure 8).…”

Section: R2mentioning

confidence: 99%

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Echinacea: Biological Effects and Active Principles

Bauer

1998

ACS Symposium Series

105

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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. Historical Use and Botanical Aspects of Echinacea SpeciesThe genus Echinacea is endemic to North America, where it occurs in the Great Plains in between the Appalachian Mountains in the east and the Rocky Mountains in the west. Its use can be traced back to the American Indians, who regarded Echinacea as one of the most favored remedies to treat wounds, snake bites, headache and the common cold (7). The territories of the tribes that most frequently used Echinacea, show a close correspondence with the distribution range of Echinacea angustifolia. Echinacea pallida and E. purpurea, and possibly other Echinacea species have also been used, however. 140

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Section: R2mentioning

confidence: 99%

“…In contrast to E. angustifolia, most of these alkamides possess a 2,4-diene moiety with the isomeric mixture of dodeca-2£:,4£,8Z,10£>Z-tetraenoic acid isobutylamides (36, 37) as the main compounds. Therefore, the roots of E. purpurea and E. angustifolia can clearly be discriminated also by HPLC of the lipophilic constituents (41,42).…”

Section: R2mentioning

confidence: 99%

Echinacea: Biological Effects and Active Principles

Bauer

1998

ACS Symposium Series

105

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“…2, were identified by mass and NMR spectroscopy as pentadeca-8Z-en-2 one (8) and heptadeca-8, 1 1-dien-2-one (9), respectively (10). Compounds 4-7 and 9 were new, while 8 has previously been described in Echinacea angustifolia roots by Schulte et al (11). According to the GC analysis, compound 8 can be regarded as the main constituent of the essential oil of E. pallida.…”

Section: Resultsmentioning

confidence: 78%

“…, which are formed in Echinacea pallida roots. Their structures turned out to be 8-hydroxy pentadeca-9E-ene-1 1,13diyn-2-one (10), 8-hydroxy pentadeca-9E,13Z-dien-11-yn-2one (11) (6), and 8-hydroxy tetradeca-9E-ene-11,13-diyn-2-HPLC separation of a methanolic extract of commercial Echinacea pallida root powder labelled as "E. angustifolia" [I = 8-hydroxytetradeca-9E-ene-11,13-diyn-2-one(12); II = 8-hydroxy-pentadeca-9E-ene-11,13-diyn-2-one (10); III = 8-hydroxy-pentadeca-9E, 13Zdien-1l-yn-2-one(11)…”

mentioning

confidence: 99%

TLC and HPLC Analysis ofEchinacea pallidaandE. angustifoliaRoots¹

Bauer¹,

Khan²,

Wagner³

1988

Planta Med

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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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