Clinanthus microstephus, an Amaryllidaceae species with cholinesterase inhibitor alkaloids: structure-activity analysis of haemanthamine skeleton derivatives

TONINO ADESSI; JOSE BORIONI; NATALIA PIGNI; JAUME BASTIDA; VALERIA CAVALLARO; ANA PAULA MURRAY; MARCELO PUIATTI; JUAN OBERTI; SEGUNDO LEIVA; VIVIANA NICOTRA; MANUELA GARCIA

Chemistry and Biodiversity

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2019 vol. 16

1612-1872

Plants of the Amaryllidaceae family are well-known (not only) for their ornamental value but also for the alkaloids they produce. In this report, the first phytochemical study of Clinanthus genus was carried out. The chemical composition of alkaloid fractions from Clinanthus microstephus was analyzed by GC-MS and NMR. Seven known compounds belonging to three structural types of Amaryllidaceae alkaloids were identified. An epimeric mixture of a haemanthamine-type compound (6-hydroxymaritidine) was tested as an inhibitor against acetyl and butyryl cholinesterase enzymes (AChE and BChE, respectively), two enzymes relevant in the treatment of Alzheimer?s Disease, with good results. Structure-activity relationships through molecular docking studies with this alkaloid and other structurally related compounds were discussed.