Long-chain acid amides, isolation from

In this chapter we describe cyclopeptide alkaloids, spermine and spermidine alkaloids, long-chain acid amides, and the cyclic oligopeptides isolated from higher plants since 1985. 

Plants of the Compositae, Piperaceae and Rutaceae families [2] have been used as ingredients in many medicinal preparations and as food spices and many of them are used as insecticides [6]. Several long-chain unsaturated amides have been isolated from these plants, and they can be classified into two main structural types (a) (2 , 4 )-dienamides derived from straight-chain fatty acids and isobutylamine, pyrrolidine or piperidine units (1-22) (Chart 1), and (b) amides with the piperonal unit derived mainly from piperic acid in combination with the above mentioned amines (23-34) (Chart 2). 

The genus Achillea (Compositae) has provided a large variety of amides derived from long-chain unsaturated acids. Investigations by Bohlmann and coworkers led to the isolation of the following bases tetradeca-(2E, 6E, %E, 122)-tetraen-10-ynoic acid 2, 3 -dehydropyrrolideide (38) from A. tomentosa L. (77),... 

In 1904, long before the advent of radioactive tracers, Knoop synthesized fatty acids labeled by chemical attachment of a benzene ring at the end opposite the carboxyl group. He prepared these compounds with both odd and even numbers of carbon atoms in straight chains and fed them to dogs. From the dogs urine he isolated hippuric acid and phenylaceturic acid, which are the amides of glycine with benzoic acid and phenylacetic acid, respectively. Knoop showed that the phenylacetic acid was produced from those fatty acids with an... 

Method 2. Place a 3 0 g. sample of the mixture of amines in a flask, add 6 g. (4-5 ml.) of benzenesulphonyl chloride (or 6 g. of j -toluenesulphonyl chloride) and 100 ml. of a 5 per cent, solution of sodium hydroxide. Stopper the flask and shake vigorously imtil the odour of the acid chloride has disappeared open the flask occasionally to release the pressure developed by the heat of the reaction. Allow the mixture to cool, and dissolve any insoluble material in 60-75 ml. of ether. If a solid insoluble in both the aqueoms and ether layer appears at this point (it is probably the sparingly soluble salt of a primary amine, e.g., a long chain compound of the type C,H5(CH,) NHj), add 26 ml. of water and shake if it does not dissolve, filter it off. parate the ether and aqueous layers. The ether layer will contain the imchanged tertiary amine and the sulphon-amide iff the secondary amine. Acidify the alkaline aqueous layer with dilate hydrochloric acid, filter off the sulphonamide of the primary amine, and recrystallise it from dilute alcohol. Extract the ether layer with sufficient 6 per cent, hydrochloric acid to remove all the tertiary amine preset. Evaporate the ether to obtain the sulphonamide of the secondary amine recrystallise it from alcohol or dilute alcohol. Finally, render the hydrochloric acid extract alkaline by the addition of dilute sodium hydroxide solution, and isolate the tertiary amine. 

Aurantoic acid isolated from the Indonesian Theondla swinhoei and motualevic acids and F isolated from a Fijian Siliquariaspongia sp. display unusual structures. Motualevic acid E is the acid part of linear amides (see below) and has only moderate antimicrobial activity (Angawi et al, 2009 Keffer et al, 2009). Motualevic add is the first long-chain 2H-azirine 2-carboxylic acid to be formd in nature. 

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