TY - JOUR
T1 - Configurational study of an aporphine alkaloid from annona purpurea
AU - Ontiveros-Rodríguez, Julio C.
AU - Burgueño-Tapia, Eleuterio
AU - Porras-Ramírez, Javier
AU - Joseph-Nathan, Pedro
AU - Zepeda, L. Gerardo
N1 - Publisher Copyright:
© 2018 Natural Product Incorporation. All rights reserved.
PY - 2018/7
Y1 - 2018/7
N2 - Purpureine (1), norpurpureine (2), and 3-hydroxyglaucine (4) were isolated from the leaves of Annona purpurea. A vibrational circular dichroism study for the absolute configuration determination of 1 provides evidence for the mutually dependent atropisomerism, local chirality of the sole stereogenic center, and the geometry of the tetrahedral nitrogen atom in aporphine alkaloids. The observed change in the optical rotation sign between 2 and its hydrochloride 3 might explain why this compound has been reported as dextrorotatory and levorotatory from the same botanical source. Furthermore, 1H and 13C NMR spectra of 1, 2 and 4 were fully assigned for the first time.
AB - Purpureine (1), norpurpureine (2), and 3-hydroxyglaucine (4) were isolated from the leaves of Annona purpurea. A vibrational circular dichroism study for the absolute configuration determination of 1 provides evidence for the mutually dependent atropisomerism, local chirality of the sole stereogenic center, and the geometry of the tetrahedral nitrogen atom in aporphine alkaloids. The observed change in the optical rotation sign between 2 and its hydrochloride 3 might explain why this compound has been reported as dextrorotatory and levorotatory from the same botanical source. Furthermore, 1H and 13C NMR spectra of 1, 2 and 4 were fully assigned for the first time.
KW - Absolute configuration
KW - Annona purpurea
KW - Aporphine alkaloids
KW - NMR assignments
KW - Vibrational circular dichroism
UR - http://www.scopus.com/inward/record.url?scp=85049027632&partnerID=8YFLogxK
U2 - 10.1177/1934578x1801300711
DO - 10.1177/1934578x1801300711
M3 - Artículo
SN - 1934-578X
VL - 13
SP - 831
EP - 836
JO - Natural Product Communications
JF - Natural Product Communications
IS - 7
ER -