Pyrrolizidine alkaloid profiles in Crotalaria species from Brazil: Chemotaxonomic significance |
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Authors: | Andria Silva Flores Ana Maria Goulart de Azevedo Tozzi Jos Roberto Trigo |
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Institution: | aMuseu Integrado de Roraima, Av. Brigadeiro Eduardo Gomes s.n., Parque Anauá, 69305-010 Boa Vista, RR, Brazil;bDepartamento de Botânica, Instituto de Biologia, Universidade Estadual de Campinas, CP 6109, 13083-970 Campinas, SP, Brazil;cLaboratório de Ecologia Química, Departamento de Biologia Animal, Instituto de Biologia, Universidade Estadual de Campinas, CP 6109, 13083-970 Campinas, SP, Brazil |
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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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Keywords: | 7-Hydroxy-1-methylene-8-pyrrolizidine Calycinae GC– MS Chrysocalycinae Crotalaria Hedriocarpae Monocrotaline Secopyrrolizidine Senecionine |
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