title: Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species.
abstract: Broad-based phytochemical investigations on 31 Stemona species and geographical provenances led to an overview concerning characteristic accumulation trends and the distribution of different Stemona alkaloids. Two major metabolic differences suggested a taxonomic segregation of the complex Stemona tuberosa group from the other species, and was supported by morphological characters. Whereas most of the Stemona species were characterised by protostemonine type alkaloids, the S. tuberosa group clearly deviated by accumulation trends towards tuberostemonine or croomine derived alkaloids belonging to two different skeletal types. Also of chemotaxonomic relevance was the structural divergence of protostemonine type alkaloids into pyrrolo- or pyridoazepine derivatives represented by stemofoline or oxystemokerrine, respectively, as major constituents. Their common occurrence in different provenances of S. curtisii, also deviating from the other species by various chromosome numbers, deserves special taxonomic attention. Species specific chemical markers were given by the unique accumulation of didehydrostemofoline (=asparagamine A) in S. collinsae and stemokerrine in S. kerrii. In contrast to previous reports, no bisdehydro derivatives with an aromatic pyrrole ring were detected supporting the hypothesis that these alkaloids are artifacts. A new stereoisomer of tuberostemonine was isolated and identified by spectroscopic methods.
authors: Comparative and Ecological Phytochemistry Section, Faculty Center of Botany, University of Vienna, Rennweg 14, A-1030 Wien, Austria.
authors: Johann
authors: J
authors: Schinnerl
authors: Brigitte
authors: B
authors: Brem
authors: Paul Pui-Hay
authors: PP
authors: But
authors: Srunya
authors: S
authors: Vajrodaya
authors: Otmar
authors: O
authors: Hofer
authors: Harald
authors: H
authors: Greger
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D015415:Biomarkers; D002851:Chromatography, High Pressure Liquid; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013045:Species Specificity; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D041901:Stemonaceae / Q000033:anatomy & histology / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000470:Alkaloids; D015415:Biomarkers; D010936:Plant Extracts; D011759:Pyrrolidines; D013141:Spiro Compounds; C034243:tuberostemonine; C082845:croomine