synthesis and natural distribution of anti-inflammatory alkamides from echinacea合成和天然抗炎alkamides从紫锥菊的分布.pdfVIP

Molecules 2006, 11, 758-767 molecules ISSN 1420-3049 Full Paper Synthesis and Natural Distribution of Anti-inflammatory Alkamides from Echinacea George A. Kraus 1,*, Jaehoon Bae 1, Lankun Wu 2 and Eve Wurtele 2 1 Iowa State University Department of Chemistry, Ames, IA 50011, USA. Tel. (+1) 515-294-7794; Fax: (+1) 515-294-0105 2 Iowa State University Department of Genetics, Development and Cell Biology, Ames, IA 50011, USA * Author to whom correspondence should be addressed; e-mail: gakraus@ Received: 2 September 2006; in revised form: 10 October 2006 / Accepted: 16 October 2006 / Published: 19 October 2006 Abstract: The synthesis of the alkamides 2Z,4E-undeca-2,4-dien-8,10-diynoic acid isobutyl amide (1) and 2Z,4E-undeca-2,4-dien-8,10-diynoic acid isobutyl amide (5) was accomplished by organometallic coupling followed by introduction of the doubly unsaturated amide moiety. The distribution of these two amides in accessions of the nine species of Echinacea was determined. Keywords: Echinacea, alkamides, synthesis. Introduction Echinacea angustifolia, Echinacea pallida and Echinacea purpurea are the main medicinal Echinacea species and have long been used to treat infections, to aid in wound healing and to enhance the immune system [1]. In 2005, Echinacea products ranked among the top botanical supplements sold in the United States. In recent years, treatment of rhinoviruses has been the focus of several studies, a number of which have failed to show the efficacy of Echinacea [2]. Commercial Echinacea products often are mixtures of the three main medicinal species and there is no regulation of t