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Pyrrolizidine alkaloid profiles inCrotalariaspecies from Brazil: Chemotaxonomic significance

Authors
Journal
Biochemical Systematics and Ecology
0305-1978
Publisher
Elsevier
Publication Date
Volume
37
Issue
4
Identifiers
DOI: 10.1016/j.bse.2009.06.001
Keywords
  • 7-Hydroxy-1-Methylene-8-Pyrrolizidine
  • Calycinae
  • Gc–Ms
  • Chrysocalycinae
  • Crotalaria
  • Hedriocarpae
  • Monocrotaline
  • Secopyrrolizidine
  • Senecionine

Abstract

Abstract Gas chromatography–mass spectrometry analysis of seeds from 28 species of Crotalaria from Brazil (sections Calycinae, Crotalaria, Chrysocalycinae and Hedriocarpae) showed that pyrrolizidine alkaloids (PAs) are important as chemotaxonomic markers at the infrageneric level. The sections Calycinae and Crotalaria were characterized by 11-membered macrocyclic monocrotaline-type PAs. In the section Chrysocalycinae, a single species in the subsection Incanae, C. incana, showed integerrimine, a 12-membered macrocyclic senecionine-type, as main PA. The group close to the subsection Stipulosae ( C. micans and C. maypurensis) showed distinctive PA patterns: C. micans presented mainly the 12-membered macrocyclic integerrimine, and C. maypurensis the unusual 7-hydroxy-1-methylene-8-pyrrolizidine. In the group close to the subsection Glaucae, the PAs with otonecine as the necine base were the main alkaloids, except in C. rufipila which showed an assamicadine-like PA (monocrotaline-type). The section Hedriocarpae showed main 12-membered macrocyclic senecionine-type PAs.

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