Liriogerphines A–D, a Class of Sesquiterpene–Alkaloid Hybrids from the Rare Chinese Tulip Tree Plant
Yu‐Hang He, Qi-Xiu Li, Yufei Wu, Chun‐Xiao Jiang, Qi Zhou, Zexin Jin, Wenxue Chen, Yicheng Mao, Jin‐Feng Hu, Juan Xiong
Abstract
Liriogerphines A–D (1–4, respectively), an unprecedented class of hybrids of germacranolide-type sesquiterpenoids and aporphine-type alkaloids, were isolated from the rare medicinal plant Liriodendron chinense. Their structures were elucidated by comprehensive spectroscopic analyses combined with electronic circular dichroism calculations and X-ray crystallographic data. Biosynthetically, an aza-Michael addition reaction is proposed to be involved in the assemblies of this class of hybrids. Compound 4 exhibited cytotoxicity against leukemia cells via inducing apoptosis and inhibiting Bcl-2 expression.
Topics & Concepts
HybridAlkaloidStereochemistryGermacranolideCircular dichroismSesquiterpeneCytotoxicityChemistryAporphineBotanyBiologyBiochemistryIn vitroTraditional and Medicinal Uses of AnnonaceaePlant Toxicity and Pharmacological PropertiesSesquiterpenes and Asteraceae Studies