Tryptophan structural classification

Table I is a compilation of plant species which contain the simple indole alkaloid types of Fig. 1. As mentioned earlier, the main requirement for the inclusion of a certain simple indole alkaloid into Table I is that it contain a tryptamine unit as a readily distinguishable feature in its structure. That tryptamine is a precursor in the biosynthesis of many of the b, c, d, and e type simple indole bases is yet to be shown although it is felt that future work will prove the correctness of such a view. Gramine, the simplest indole alkaloid, has been included in the tryptamine classification a because it is biosynthetically related to tryptophan cryptole-pine has been likewise included therein although its structural relationship to tryptophan appears more obscure (Volume VIII, Chapter 1, pp. 4, 19). The calycanthine type does not possess a tryptamine structure but it is included in the simple indole alkaloid b classification since most of its congeners are tryptamine derivatives and since it exhibits a close biogenetic relationship to this latter (chimonanthine) type (Volume VIII, Chapter 16). Type d is represented by the small number of the so-called canthin-6-one alkaloids (Volume VIII, pp. 260-252, 497-498). The most recent variation of the simple indole alkaloids is found in the Anacardiaceae family. Its indoloquinolizidine nucleus suggests inclusion with type d on the basis of structural and biogenetic similarity. Finally, simple indole alkaloid type e is composed of the well-defined evodiamine (rutaecarpine) structural form (Volume VIII, Chapter 4).

Presently, alkaloids are classified into three main categories as shown in Fig. 8.2 [6]. This chemical classification of alkaloids is universally adapted and mainly depends on the type of heterocyclic ring structure present (Fig. 8.3). Alkaloids are further classified according to the amino acids (or their derivatives) from which they originate (Fig. 8.4) [6]. The most important classes are derived from the amino acids, ornithine and lysine, or from the aromatic amino acids, phenylalanine and tyrosine, or from tryptophan and a moiety of mavelonoid origin. A number of alkaloid-based compounds are also derived from anthranilic acid or from nicotinic acid. 

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