Mappianines A-E, structurally diverse monoterpenoid indole alkaloids from Mappianthus iodoides
Gui-Jie Zhang1, Feng Hu2, Huan Jiang2
1State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, People's Republic of China; College of Pharmacy, Guilin Medical University, Guilin 541004, People's Republic of China.
Abstract:
Five previously undescribed monoterpenoid indole alkaloids, mappianines A-E, along with twelve known analogues, were isolated from the stems of Mappianthus iodoides Hand.-Mazz. Their structures and absolute configurations were determined by spectroscopic analysis, single-crystal X-ray diffraction, and ECD calculations. The plausible biogenetic pathway of mappianine A was proposed. All the isolated compounds were evaluated for their cytotoxic effects on MGC-803, Bel-7404, A549, NCI-H460, and HepG2 cancer cell lines. Mappianine B, tetrahydroalstonine, β-carbolin-1-one, and 1,2,3,4-tetrahydronorharman-1-one displayed moderate cytotoxicity against all cell lines tested, with IC50 values ranging from 5.19 to 42.86 μM.
Related Concept Videos
Nomenclature of Aryl and Heterocyclic Amines
Nomenclature of Primary Amines
Basicity of Heterocyclic Aromatic Amines
Amines: Introduction
Opioid Analgesics: Morphine and Other Natural Cogeners
Cholinergic Antagonists: Chemistry and Structure-Activity Relationship


