7,7-Dimethylaporphine alkaloids from the stem of Guatteriopsis friesiana.
Phytochemical investigation of a methanolic extract of the stem of Guatteriopsis friesiana afforded two new 7,7-dimethylaporphine alkaloids, 6,6a-dihydrodemethoxyguadiscine (1) and guatteriopsiscine (3), together with demethoxyguadiscine (2), liriodenine (4), corypalmine (5), and coreximine (6). Their structures were elucidated on the basis of spectroscopic methods (UV, IR, EIMS, HRESIMS, 1D/2D NMR). The absolute configurations of 1 and 3 were determined from the circular dichroism curves. The presence of 7,7-dimethylaporphine alkaloids in this species is important for the chemotaxonomy of Guatteriopsis. Antimicrobial activity of compounds 1-5 was investigated, and 4 showed activity against Rhodococcus equi, with a MIC value of 10 microg x mL(-1).
Costa
Emmanoel Vilaça
EV
Departamento de Quimica, Universidade Federal do Parana, Centro Politecnico, P.O. Box 19081, 81531-990 Curitiba, PR, Brazil.
Marques
Francisco A
FA
Pinheiro
Maria Lúcia B
ML
Vaz
Nelissa P
NP
Duarte
Marta Cristina T
MC
Delarmelina
Camila
C
Braga
Raquel M
RM
Maia
Beatriz Helena L N Sales
BH
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029061:Annonaceae / Q000737:chemistry* / Q000145:classification; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018547:Plant Stems / Q000737:chemistry; D016929:Rhodococcus equi / Q000187:drug effects*
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D001060:Aporphines; C026980:liriodenine