Cage-Monoterpenoid Quinoline Alkaloids with Neurite Growth Promoting Effects from the Fruits of <i>Melodinus yunnanensis</i>
Jing Wu, Simeng Zhao, Bao‐Bao Shi, Mei‐Fen Bao, Johann Schinnerl, Xiang‐Hai Cai
Abstract
Meloyunnanines A–C, three alkaloids with an unprecedented skeleton, were isolated from fruits of Melodinus yunnanensis. The structures featuring a caged-6/6/5/6/5/5 ring system were elucidated by the analysis of comprehensive spectroscopic and X-ray data. Biosynthetically, meloyunnanines A–C were assigned to monoterpenoid quinoline alkaloids (MQAs), derived from monoterpenoid indole alkaloids through oxidation and rearrangement. These compounds together with three known Melodinus MQAs were evaluated for their neurotrophic activity and scandine N4-oxide exhibited significant effect.
Topics & Concepts
ChemistryQuinolineStereochemistryIndole testAlkaloidOrganic chemistryAlkaloids: synthesis and pharmacologyTraditional and Medicinal Uses of AnnonaceaeChemical synthesis and alkaloids