Synthesis of N-(2-methylpropyl)-2E-undecene-8,10-diynamide, a novel constituent of Echinacea angustifolia

Kraus, George A.; Bae, Jaehoon

doi:10.1016/s0040-4039(03)01253-x

Cited by 22 publications

(14 citation statements)

References 7 publications

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“…Bohlmann synthesized 1 and 5 in low overall yields, in part because the Wittig reactions that installed the cis-amide moiety produced the cis-isomers in only 13-14% yields [13]. Kraus and Bae have reported syntheses of amides 2 and 3 and ketone 4 [14,15]. We report herein the preparation of diacetylenic amides 1 and 5.…”

Section: Synthesis Of Alkamidesmentioning

confidence: 93%

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Kraus

Bae

et al. 2006

Molecules

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Section: Synthesis Of Alkamidesmentioning

confidence: 93%

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Kraus

Bae

et al. 2006

Molecules

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“…The identity of select alkamides was determined by running unknown extracts with individual synthesized alkamide standards (nos. 1, 2, 3, 4, 7, 8, 9, 10, and 11) provided by colleagues at Iowa State University (Kraus and Bae 2003;Wu et al 2004).…”

Section: Methodsmentioning

confidence: 99%

“…The extraction of compounds from whole plants has been the traditional method of isolating bioactive secondary metabolites. Because of the complexity of many of these compounds (Kraus and Bae 2003), chemical synthesis has been limited. In vitro technology has provided a valuable alternative for the production of natural, bioactive secondary compounds (Bourgaud et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Alkamide production from hairy root cultures of Echinacea

Romero

Delate

Kraus

et al. 2009

In Vitro Cell.Dev.Biol.-Plant

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Hairy root cultures of Echinacea, one of the most important medicinal plants in the US, represent a valuable alternative to field cultivation for the production of bioactive secondary metabolites. In this study, the three most economically important species of Echinacea (Echinacea purpurea, Echinacea pallida, and Echinacea angustifolia) were readily transformed with two strains of Agrobacterium that produce the hairy root phenotype. Transformed roots of all three species exhibited consistent accelerated growth and increased levels of alkamide production. Optimization of the culture of Echinacea hairy roots was implemented to enhance both growth and alkamide production concomitantly. The use of halfstrength Gamborg's B5 medium supplemented with 3.0% sucrose was twice as effective in maintaining hairy root production than any other media tested. The addition of indolebutyric acid increased the growth rate of roots by as much as 14-fold. Alkamide production increased severalfold in response to the addition of the elicitor, jasmonic acid, but did not respond to the addition of indolebutyric acid. Induced accumulation of the important bioactive compounds, alkamides 2 and 8, was observed both in transformed roots and in response to jasmonic acid treatments. The results of this study demonstrate the efficacy of hairy root cultures of Echinacea for the in vitro production of alkamides and establish guidelines for optimum yield.

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“…Isobutylamides from the roots of E. purpurea contain mainly 2,4-dienoic units, while those of E. angustifolia contain mainly 2-monoene units . The synthesis of the acetylenic amide N-(2-methylpropyl)-2E-undecene-8,10-diynamide, a constituent of E. angustifolia root, has been reported (Kraus & Bae 2003). E. purpurea root reportedly contains 0.01-0.04% alkamides (European Scientific Co-operative on Phytotherapy 2003).…”

Section: Alkamidesmentioning

confidence: 99%

Echinaceaspecies (Echinacea angustifolia(DC.) Hell.,Echinacea pallida(Nutt.) Nutt.,Echinacea purpurea(L.) Moench): a review of their chemistry, pharmacology and clinical properties

Barnes

Anderson²,

Gibbons

et al. 2005

Journal of Pharmacy and Pharmacology

356

310

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This paper reviews the chemistry, pharmacology and clinical properties of Echinacea species used medicinally. The Echinacea species Echinacea angustifolia, Echinacea pallida and Echinacea purpurea have a long history of medicinal use for a variety of conditions, particularly infections, and today echinacea products are among the best-selling herbal preparations in several developed countries. Modern interest in echinacea is focused on its immunomodulatory effects, particularly in the prevention and treatment of upper respiratory tract infections. The chemistry of Echinacea species is well documented, and several groups of constituents, including alkamides and caffeic acid derivatives, are considered important for activity. There are, however, differences in the constituent profile of the three species. Commercial echinacea samples and marketed echinacea products may contain one or more of the three species, and analysis of samples of raw material and products has shown that some do not meet recognized standards for pharmaceutical quality. Evidence from preclinical studies supports some of the traditional and modern uses for echinacea, particularly the reputed immunostimulant (or immunomodulatory) properties. Several, but not all, clinical trials of echinacea preparations have reported effects superior to those of placebo in the prevention and treatment of upper respiratory tract infections. However, evidence of efficacy is not definitive as studies have included different patient groups and tested various different preparations and dosage regimens of echinacea. On the basis of the available limited safety data, echinacea appears to be well tolerated. However, further investigation and surveillance are required to establish the safety profiles of different echinacea preparations. Safety issues include the possibility of allergic reactions, the use of echinacea by patients with autoimmune diseases and the potential for echinacea preparations to interact with conventional medicines.

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Synthesis of N-(2-methylpropyl)-2E-undecene-8,10-diynamide, a novel constituent of Echinacea angustifolia

Cited by 22 publications

References 7 publications

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea

Alkamide production from hairy root cultures of Echinacea

Echinaceaspecies (Echinacea angustifolia(DC.) Hell.,Echinacea pallida(Nutt.) Nutt.,Echinacea purpurea(L.) Moench): a review of their chemistry, pharmacology and clinical properties

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