Amaryllidaceae alkaloids: Absolute configuration and biological activity

Plants belonging to the Amaryllidaceae family are well known for their ornamental and medicinal use. Plant members of this group are distributed through both tropical and subtropical regions of the world and are dominant in Andean South America, the Mediterranean basin, and southern Africa. Amarylli...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2017-09, Vol.29 (9), p.486-499
Main Authors: Cimmino, Alessio, Masi, Marco, Evidente, Marco, Superchi, Stefano, Evidente, Antonio
Format: Article
Language:English
Subjects:
Absolute configuration
Acetylcholinesterase
Alkaloids
Alzheimer's disease
Amaryllidaceae
Amaryllidaceae Alkaloids - chemistry
Amaryllidaceae Alkaloids - pharmacology
Anticancer properties
Antitumor activity
Biological activity
Configurations
Medicinal plants
Neurodegenerative diseases
Ornamental plants
Plants (botany)
relative and/or absolute configuration
Solid tumors
Stereochemistry
Stereoisomerism
Structure-Activity Relationship
structure‐activity relationships
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Summary:Plants belonging to the Amaryllidaceae family are well known for their ornamental and medicinal use. Plant members of this group are distributed through both tropical and subtropical regions of the world and are dominant in Andean South America, the Mediterranean basin, and southern Africa. Amaryllidaceae plants have been demonstrated to be a good source of alkaloids with a large spectrum of biological activities, the latter being strictly related to the absolute stereochemistry of the alkaloid scaffold. Among them, great importance for practical applications in medicine has galanthamine, which has already spawned an Alzheimer's prescription drug as a potent and selective inhibitor of the enzyme acetylcholinesterase. Furthermore, lycorine as well as its related isocarbostyryl analogs narciclasine and pancratistatine have shown a strong anticancer activity in vitro against different solid tumors with malignant prognosis. This review addresses the assignment of the absolute configuration of several Amaryllidaceae alkaloids and its relationship with their biological activities.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22719