Chemical and Biological Aspects of Different Species of the Genus Clinanthus Herb. (Amaryllidaceae) from South America

Abstract

The genus Clinanthus Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important structural diversity and pharmacological properties. It is possible to find some publications in the literature regarding the botanical aspects of Clinanthus species, although there is little information available about their chemical and biological activities. The aim of this work was to obtain the alkaloid profile and the anti-cholinesterase activity of four different samples of Clinanthus collected in South America: Clinanthus sp., Clinanthus incarnatus, and Clinanthus variegatus. The alkaloid extract of each sample was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and their potential against the enzymes acetyl- and butyrylcholinesterase were evaluated. Thirteen alkaloids have been identified among these species, while six unidentified structures have also been detected in these plants. The alkaloid extract of the C. variegatus samples showed the highest structural diversity as well as the best activity against AChE, which was likely due to the presence of the alkaloid sanguinine. The results suggest this genus as a possible interesting new source of Amaryllidaceae alkaloids, which could contribute to the development of new medicines.

Molecular Docking and GC/MS‐Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model

“…(Amaryllidaceae). [22] A detailed mass fragmentation mechanism supporting the structure suggested for alkaloid 21 is described in Figure 1.The mass spectrum of compound 23 (RI = 2999) exhibited a peak corresponding to the molecular ion at m/z 265 [M] + , differing from compound 21 by only 14 mass units. The base ion with m/z 264 [MÀ H] + , along with the ion at m/z 236 [MÀ CO] + indicated a hydroxy group at C2 in agreement with the loss of radical hydrogen and CO, respectively.…”

“…Griffinia liboniana was found to be composed by the alkaloids trisphaerdine (4), galanthamine (5), sanguinine (7), vittatinte(9a)/crinine (9b), narwerdine (10), nerinine (11), anhydrolycorine (12), crinan-3-one (13), pancratinine C (14) 11,12dehydroanhydrolycorine (15), 6α-hydroxyhippeastidine (16), haemanthamine (17), undulatiane diol (18), 11,12-dehydroassoanine (19), lycorine (20), 11,12-dehydro-2-methoxyanhydrolychorine (21), 11,12-dehydro-2-methoxyassoanine (22), 11,12dehydro-2-hydroxyanhydrolychorine (23), 11,12-dehydro-2-hydroxyasoanine (24) and 11,12-dihydro-2-methoxypratosine (25) in addition to the protoalkaloids hordeine (1) and methyltyramine isomer (2). To the best of our knowledge, there was no published chemical study of the species G. liboniana hitherto.…”

“…[32] The biplot of the PCs and their respective loadings resulted in a two-dimensional graph (Figure 4B) that was used to determine which compounds were discriminant for the cluster separation. Overall, 14 alkaloids showed major influence: galanthamine (5), lycoramine (6), norlycoramine (8), nerinine (11) and unknown E (30) for G. gardneriana; 11,12-dehydroassoanine (19), 11,12-dehydromethoxyassoanine (22), 11,12-dihydro-2-methoxypratosine (25), unknown A (26) and unknown H (33) for G. liboniana; besides 11,12-dehydrolycorene isomer (3), anhydrolycorine (12), unknown C (28) and unknown G (32) for G. nocturna.…”

Alkaloid Profiling and Anti-Cholinesterase Potential of Three Different Genera of Amaryllidaceae Collected in Ecuador: <em>Urceolina</em> Rchb., <em>Clinanthus</em> Herb., and <em>Stenomesson</em> Herb

“…According to the literature, C. incarnatus collected in Peru presented a high amount of lycorine (15), as well as seven other different alkaloids [27]. A current publication revealed the presence of two lycorine-type alkaloids in C. incarnatus collected in Ecuador, which are lycorine and 11,12-dehydroanhydrolycorine, and 4 unidentified structures, that probably belong to lycorine-and ismine-type skeleton [28].…”

“…Allen collected in Panama and evaluated by Calderón and co-authors showed activity against AChE though TLC bioautographic methodology, while the whole plant extract was inactive [29]. A currently publication described the IC50 values of the alkaloid extract of C. incarnatus as higher than 40 µg•ml -1 against AChE and BuChE, representing the low activity of this species against both enzymes [28]. Although the alkaloid profiling of S. aurantiacum have been previously reported in the literature, this is the first report about its anti-cholinestarase potential.…”