title: Influence of tryptophan and related compounds on ergot alkaloid formation in Claviceps purpurea (FR.) Tul.
abstract: L-Tryptophan did not exert any influence on peptide alkaloid formation in an ergotamine and in an ergosine-accumulating C. purpurea strain. A different picture was observed in a series of related C. purpurea strains. Tryptophan showed a slight stimulatory effect on the ergotoxine producer Pepty 695/S. A blocked mutant of it, designated as Pepty 695/ch which was able to accumulate secoclavines gave similar results. In a high-yielding elymoclavine strain Pepty 695/e, the progeny of the former one, tryptophan up to a concentration of 25 mM stimulated remarkably clavine biosynthesis. Furthermore, tryptophan could overcome the block of synthesis by inorganic phosphate. Increased specific activities of chanoclavine cyclase but not DMAT synthetase were observed in cultures of strain Pepty 695/e supplemented with tryptophan. 5-Methyltryptophan and bioisosteres of tryptophan were ineffective in alkaloid stimulation. These results are compared with those obtained with the grass ergot strain SD 58 and discussed with the relation to other induction phenomena.
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D002967:Claviceps / Q000187:drug effects* / Q000235:genetics / Q000378:metabolism; D003470:Culture Media; D004873:Ergolines / Q000096:biosynthesis; D004876:Ergot Alkaloids / Q000096:biosynthesis*; D009154:Mutation; D010710:Phosphates / Q000494:pharmacology; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000494:pharmacology*
chemical_list: D003470:Culture Media; D004873:Ergolines; D004876:Ergot Alkaloids; D010710:Phosphates; C006959:chanoclavine; C007586:elymoclavine; C028129:tryptophan methyl ester; D014364:Tryptophan; C004465:agroclavine