Unsaturated Alkyl Amides

Secondary substituents of this type have a somewhat restricted distribution in higher plants. They are, however, fairly common in Echinacea species and are

Formula Chart No. 4 Unsaturated keto alcohols of echinacea.

Formula Chart No. 4 Unsaturated keto alcohols of echinacea.

Formula Chart No. 5 Unsaturated polyenes and acetylenes of echinacea.

believed to be primarily responsible for the tingling and local anesthetic effects observed on the tongue when these materials and plants are placed in the mouth. Herbalists often use this effect as an indication that the plants are mature enough to harvest. Interestingly, these kinds of compound are present in spicy plants as well and a number of such species (pepper, containing piperine and chavacine, for example, but not Echinacea species) are used in cooking. Despite their evident ability to undergo Michael-type addition reactions, they are apparently not especially toxic to humans in the doses normally applied. The first of these to be characterized chemically from echinacea is echinacein (69). It was shown to be toxic to houseflies. Subsequently a large number of other polyunsaturated amides of echinacea have been characterized. Because they have excellent ultraviolet (UV) chromophores and their specific distribution among the Echinacea species is characteristic, they have been popular HPLC fingerprinting substances to demonstrate which species of Echinacea is present (70). (Formula Charts 6 and 7).

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