Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family

Abstract

Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer’s disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type.

Amaryllidaceae Alkaloids of Norbelladine-Type as Inspiration for Development of Highly Selective Butyrylcholinesterase Inhibitors: Synthesis, Biological Activity Evaluation, and Docking Studies

“…Lycorine, haemanthamine, pancratistatine, and narciclasine are known to possess antiproliferative properties [ 30 , 31 , 32 ]. Montanine governs antidepressive, anticonvulsive, anti-rheumatic, antimicrobial, and antitumor activities [ 33 ]. The emerging data and potential applicability of AAs spur the search for new alkaloids from this family.…”

Semisynthetic Derivatives of Selected Amaryllidaceae Alkaloids as a New Class of Antimycobacterial Agents

“…Derivatives of 3- O -methylpancracine were originally synthesized to study the cytotoxic potential of montanine-type Amaryllidaceae alkaloids. The promising antiproliferative properties of some representatives of this structural type of AA, and the limited presence of these alkaloids in plant material, initiated the total synthesis and production of synthetic analogues of these alkaloids [ 22 , 23 ]. Among these, the montanine-type structure was successfully achieved with intramolecular rearrangement of haemanthamine, which is considered a convenient semi-synthetic method for achieving the montanine-type skeleton due to the ready availability of haemanthamine from plants of the Amaryllidaceae family [ 23 ].…”

Pancracine, a Montanine-Type Amaryllidaceae Alkaloid, Inhibits Proliferation of A549 Lung Adenocarcinoma Cells and Induces Apoptotic Cell Death in MOLT-4 Leukemic Cells

“…Thirteen years later, in 1968, Wildman and coworkers described another AA of a montanine type, pancracine, which they isolated from Pancratium maritimum, Narcissus poeticus, and Rhodophiala bifida [4]. Since then, attention has turned to investigations performed to gain a deeper understanding of montanine-type alkaloids, including either the possibility of isolation from other plants of the Amaryllidaceae family [6], preparing them by chemical de novo synthesis [5], or exploring their biological activity [6,[8][9][10]. In our previous work, we screened the cytotoxicity of AA of various structural types isolated from bulbs of Narcissus cv.…”