Further bioactive piperidine alkaloids from the flowers and green fruits of Cassia spectabilis.
The flowers of Cassia spectabilis yielded three new piperidine alkaloids, (-)-3-O-acetylspectaline (1), (-)-7-hydroxyspectaline (2), and iso-6-spectaline (3), together with the known (-)-spectaline (4). The green fruits of this plant were also investigated, resulting in the isolation of 1 and 4. Their structures were elucidated using a combination of multidimensional NMR and MS techniques, and relative stereochemistries were established by NOESY correlations and analysis of coupling constants. The DNA-damaging activity of these compounds was evaluated using a mutant yeast, Saccharomyces cerevisiae, assay.
Viegas
Claudio
C
Instituto de Química, Universidade Estadual Paulista (UNESP), CP 359, 14800-900, Araraquara, SP, Brazil.
da S  Bolzani
Vanderlan
V
Furlan
Maysa
M
Barreiro
Eliezer J
EJ
Young
Maria Claudia M
MC
Tomazela
Daniela
D
Eberlin
Marcos N
MN
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D002366:Cassia / Q000737:chemistry*; D004249:DNA Damage; D035264:Flowers / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000235:genetics; D013237:Stereoisomerism
C487262:3-O-acetylspectaline; C487263:7-hydroxyspectaline; D000470:Alkaloids; D010880:Piperidines; C487264:iso-6-spectaline; C480880:spectaline