Five new alkaloids from the leaves of Remijia peruviana.
Three new indolylquinuclidine-type alkaloids, remijinine (1), epiremijinine (2), and 5-acetyl-apocinchonamine (3), and two new cinchonine-derived alkaloids, N-acetyl-deoxycinchonicinol (4) and N-acetyl-cinchonicinol (5), as well as the known alkaloids quinamine, conquinamine, cinchonine, and quinidine were isolated from the leaves of Remijia peruviana. The structures of the new alkaloids were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC, and HMBC). The relative configuration at C-7 for remijinine (1) and, in consequence, for epiremijinine (2) was established by X-ray crystal structure analysis of the former.
Díaz
Jesús G
JG
Instituto de Bio-Orgánica Antonio González, Universidad de La Laguna, Carretera de La Esperanza 2, 38206, Tenerife, Spain. jglezd@ull.es
Sazatornil
José Gavin
JG
Rodríguez
Matías López
ML
Mesía
Lastenia Ruiz
LR
Arana
Gabriel Vargas
GV
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D019666:Rubiaceae / Q000737:chemistry*
C493623:5-acetyl-apocinchonamine; D000470:Alkaloids; D007211:Indoles; C493622:epiremijinine; C493621:remijinine