Anti-Acanthamoeba castellanii activity of alkaloid-enriched extracts and lycorine from the Amaryllidaceae species

Abstract Free-living amoebae of the genus Acanthamoeba are the causative agents of granulomatous encephalitis and keratitis, severe human infections. Bioactive compounds from plants are recognized as an alternative source for the development of new drugs. The Amaryllidaceae is a botanical family able to synthesize a very specific and consistent group of biologically active isoquinoline-like alkaloids. The alkaloidal fractions from the Brazilian species Hippeastrum canastrense, H. diniz-cruziae, H. puniceum, and Crinum x amabile, along with the alkaloid lycorine, were investigated against Acanthamoeba castellanii. The in vitro assays were performed with distinct concentrations of lycorine and alkaloidal fractions, while the cell viability was evaluated by the MTT method upon MDCK cells. Chlorhexidine 0.02% was used as the positive control. The effect of alkaloid fractions was concentration dependent, and 2000 µg mL-1 of H. canastrense and H. diniz-cruziae provided a 100% inhibition. At concentrations of 250, 500, and 1000 µg mL-1, the H. diniz-cruziae alkaloidal fraction showed the lowest cytotoxic effect (5%-7%) and remarkable anti-amoebic activity, demonstrating values of IC50 285.61 µg mL-1, low cytotoxicity (5%-7%), and selectivity index (7.0). Taken together, the results are indicative of the great potential that the alkaloids from H. diniz-cruziae have as new candidates for anti-amoebicidal compounds

Chemical evaluation and anticholinesterase activity of Hippeastrum puniceum (Lam. ) Kuntz bulbs (Amaryllidaceae)

Hippeastrum puniceum is a species that belongs to the Amaryllidaceae family. A particular characteristic of this family is the consistent and very specific presence of isoquinoline alkaloids, which have demonstrated a wide range of biological activities such as antioxidant, antiviral, antifungal, antiparasitic, and acetylcholinesterase inhibitory activity, among others. In the present work, fifteen alkaloids were identified from the bulbs of Hippeastrum puniceum (Lam.) Kuntz using a GC-MS approach. The alkaloids 9-O-demethyllycoramine, 9-demethyl-2α-hydroxyhomolycorine, lycorine and tazettine were isolated through chromatographic techniques. The typical Amaryllidaceae alkaloids lycorine and tazettine, along with the crude and ethyl acetate extract from bulbs of the species were evaluated for their inhibitory potential on α-amylase, α-glucosidase, tyrosinase and acetylcholinesterase activity. Although no significant inhibition activity was observed against α-amylase, α-glucosidase and tyrosinase from the tested samples, the crude and ethyl acetate extracts showed remarkable acetylcholinesterase inhibitory activity. The biological activity results that correlated to the alkaloid chemical profile by GC-MS are discussed herein. Therefore, this study contributed to the knowledge of the chemical and biological properties of Hippeastrum puniceum (Lam.) and can subsidize future studies of this species

Taxonomical Investigation on Some Species of Genus Allium Based on the Pollen Morphology

Aims: The aim of this research was to investigate the morphological characteristics of the pollen grain of some species of genus Allium. Methodology: The pollen grains were examined by using Light Microscopy (LM), Scanning Electron Microscopy (SEM) and the pollen grains of one species under Transmission Electron Microscopy (TEM). Results: The pollen grains were oblate and medium in shape and size. The pollen ornamentation of exine surface, exine ornamentation on sulcus edge, lumina number in the exine surface and the state of pollen grain apex in the examined species were different. Semitectate and columellate ectexine with discontinuous endexine were seen in the pollen wall structure (sporoderm). The dendrogram obtained from the pollen characters in SEM observations by using the numerical taxonomy system (NTSYS) software placed the studied species in two types. Conclusion: Our palynological dendrogram can be used for segregation the sections and subgenera taxonomical levels in the studied species of genus Allium and confirmed the phylogram of the recent phylogenetic research.

Rhodolirium andicola: a new renewable source of alkaloids with acetylcholinesterase inhibitory activity, a study from nature to molecular docking

ABSTRACT Acetylcholinesterase is an important target for control of neurodegenerative diseases causing cholinergic signaling deficit. Traditionally, galanthamine has been used as an Amaryllidaceae-derived acetylcholinesterase inhibitor, although new Amaryllidaceae plants could serve as source for better acetylcholinesterase inhibitors. Therefore, the objective of this study was to characterize the alkaloid composition from bulbs of Rhodolirium andicola (Poepp.) Traub, a native Chilean Amaryllidaceae specie, and assess their inhibitory activity on acetylcholinesterase by in vitro and in silico methodologies. Alkaloidal extracts from R. andicola exhibited an inhibitory activity with IC50 values between 11.25 ± 0.04 and 57.78 ± 1.92 µg/ml that included isolated alkaloid, galanthamine (2.3 ± 0.18 µg/ml), Additionally, 12 alkaloids were detected using gas chromatography-mass spectrometry and identified by comparing their mass fragmentation patterns with literature and database NIST vs.2.0. To better understand the bioactivity of isolated compounds and alkaloidal extracts against acetylcholinesterase, a molecular docking approach was performed. Results suggested that alkaloids such as lycoramine, norpluvine diacetate and 6α-deoxy-tazettine expand the list of potential acetylcholinesterase inhibitors to not only galanthamine. The role of R. andicola as a source for acetylcholinesterase inhibitors is further discussed in this study.

Amaryllidaceae alkaloids from Lycoris radiata / 中国中药杂志

Three aporphine-type alkaloids (1-3), three lycorine-type alkaloids (4-6), two crinane type alkaloids (7, 8) and one phenanthridine-type alkaloid (9) were isolated from the chloroform soluble fraction of 70% ethanol extract of the bulbs of Lycoris radiata through various column chromatographies over silica gel, ODS, Sephadex LH-20 and MCI. Their structures were elucidated as (+)-N-methoxylcarbonyl-1,2-methylenedioxyl-isocorydione (1), isocorydione (2), 8-demethyl-dehydrocrebanine (3), (+)-3-hydroxy-anhydrolycorine N-oxide (4), vasconine (5), pancratinine D (6), yemenine A (7), 11-O-acetylhaemanthamine (8), and 5,6-dihydro-5-methyl-2-hydroxyphenanthridine (9) based on their chemical and physicochemical properlies and spectroscopic data. Compound 1 was a new compound and alkaloids 2-9 were isolated and identified from this plant for the first time.

Application of HPLC-DAD for the quantification of Lycorine in Galanthus elwesii Hook

ABSTRACT In the present study, a reversed-phase high-performance liquid chromatographic method has been used for the quantitative determination of lycorine in the aerial parts and bulbs of G. elwesii Hook. A simple method for the extraction of lycorine in low mass plant samples was employed utilizing pre-packed columns with diatomaceous earth (Extrelut(r)). The chromatographic separation was performed using an isocratic system with a mobile phase of trifluoroacetic acid-water-acetonitrile (0.01:92.5:7.5, v/v/v) applied at a flow rate 1 mL min-1 using diode array detector. The content of lycorine in the bulbs and aerial parts of G. elwesii collected from Demirci (Manisa) was found as 0.130 and 0.162 %, respectively. Additionally, in the bulbs of the specimens collected from Sogucak (Balikesir), lycorine was quantified as 0.055 %, whereas in the aerial parts, it was determined as 0.006 %. The method was validated partially with respect to system specificity, linearity, accuracy, precision, limits of detection (LOD) and quantitation (LOQ). Validation procedures displayed that the method was specific, accurate and precise.

New lycosinine derivative from Hippeastrum breviflorum

AbstractA new lycosinine derivative, 9-O-demethyllycosinine B, was isolated from the native Brazilian Hippeastrum breviflorumHerb., Amaryllidaceae, along with the well-known alkaloids lycosinine B and lycorine. The structure of the new compound was established by physical and spectroscopic methods. 9-O-demethyllycosinine B is the third lycosinine variant identified in the Amaryllidaceae family.

A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata / 中国天然药物

AIM@#To study the Amaryllidaceae alkaloids of the bulbs of Lycoris radiata.@*METHODS@#The chemical constituents were isolated and purified by various chromatographic techniques, and the chemical structures were elucidated on the basis of spectroscopic methods. In addition, the antiviral activities of alkaloids 1-10 were evaluated using flu virus A.@*RESULTS@#One new homolycorine-type alkaloid 2α-methoxy-6-O-ethyloduline (1), together with nine known alkaloids 2α-methoxy-6-O-methyloduline (2), trispherine (3), 8-O-demethylhomolycorine (4), homolycorine (5), 9-O-demethylhomolycorine (6), oduline (7), lycorenine (8), 6α-O-methyllycorenine (9) and O-ethyllycorenine (10) were obtained.@*CONCLUSION@#Alkaloid 1 is a new compound, and 1-3 were major alkaloids in this plant. Alkaloids 1-3 showed weak antiviral activities against flu virus A with IC50 values of 2.06, 0.69, and 2.71 μg·mL-1 and CC50 values of 14.37, 4.79, and 80.12 μg·mL-1, respectively.

Analysis of Amaryllidaceae alkaloids from Zephyranthes grandiflora by GC/MS and their cholinesterase activity

Amaryllidaceae are known as ornamental plants, furthermore some species of this family contain galanthamine, an acetylcholinesterase inhibitor approved for the treatment of Alzheimer's disease, and other alkaloids with interesting pharmacological activity. The chemical composition of alkaloids from Zephyranthes grandiflora Lindl. was analyzed by GC/MS. Seven known compounds, belonging to five structural types of Amaryllidaceae alkaloids, were identified. The alkaloid extract from the bulbs showed promising cholinesterase inhibitory activities against human blood acetylcholinesterase (HuAChE; IC50 39.2±3.0 µg/mL) and human plasma butyrylcholinesterase (HuBuChE; IC50 356±9.3 µg/mL).

Benzylphenethylamine Alkaloids from the Bulbs and Flowers of Lycoris radiata / 中草药·英文版

Objective To study the benzylphenethylamine alkaloids from the bulbs and flowers of Lycoris radiata.Methods Alkaloids were isolated by various column chromatographic methods and their structures were identified by spectral data.Results Fifteen known benzylphenethylamine alkaloids were isolated and identified as lycoramine(1),O-demethyllycoramine(2),N-demethyllycoramine(3),galanthamine(4),lycorine(5),caranine(6),ungminorine(7),narciclasine(8),5-hydroxy-10-O-demethyl-homolycorine(9),hippeastrine(10),ungerine(11),hippeastrine N-oxide(12),O-demethylhaemanthamine(13),haemanthidine(14),and 8-demethoxybostasine(15).Conclusion Compound 15 is first isolated from the plants in Amaryllidaceae,compounds 3,6,9,and 11 are first reported from the plants in Lycoris Herb.,and compounds 2,7,and 14 are isolated from L.radiata for the fast time.The 13C-NMR data of compouds 3,7,and 12 are first reported in the present study.Furthermore,the galasine-type alkaloid is isolated from the plants of Lycoris Herb.for the first time.

Non-alkaloids in Hippeastrun vittatum / 中草药

Objective To investigate the non-alkaloid constituent of Hippeastrun vittatum (Amaryllidaceae). Methods Solvent extraction and column chromatography were used to isolate the non-alkaloid constituents, and physicochemical constants and spectroscopic analysis were employed for structural elucidation. Results Five glycosphingosilipids were isolated, and their structures were elucidated to be (2S,3R, 4E, 8Z)-2-[(2R-2-hydroxyhexadecanoyl) amido ]-4, 8-octadecadiene-1, 3-diol 1-O-β-D-glucopyranoside ( Ⅰ ), (2S, 3R, 4E, 8E)-2-[(2R-2-hydroxyhexadecanoyl) amido]-4, 8-octadecadiene-1, 3-diol 1O-β-D-glucopyranoside ( Ⅱ ), (2S, 3R, 4E, 8Z)-2-[(2R-2-hydroxyoctadecanoyl) amido]-4, 8-octadecadiene-1, 3-diol 1-O-β-D-glucopyranoside (Ⅲ), (2S, 3R, 4E, 8E)-2-[(2R-2-hydroxyoctadecanoyl)amido]4, 8-octadecadiene-1, 3-diol 1-O-β-D-glucopyranoside ( Ⅳ ), (2S, 3R, 4E, 8Z)-2-[(2R-2-hydroxyeicosadecanoyl) amido]-4, 8-octadecadiene-1, 3-diol 1-O-β-D-glucopyranoside (Ⅴ), respectively. Conclusion They are all isolated from the fresh bulbs of H. vittatum for the first time.

Avaliação da atividade antiviral e determinação do perfil cromatográfico de Hippeastrum glaucescens (Martius) Herbert (Amaryllidaceae) / Evaluation of antiviral activity and determination of the chromatographic profile of Hippeastrum glaucescens (Martius) Herbert (Amaryllidaceae)

Plantas da família Amaryllidaceae são caracterizadas pela presença de alcalóides isoquinolínicos. Desde o primeiro estudo envolvendo alcalóides desta família em 1877, um grande número destas plantas tem sido analisado quimicamente. Estes compostos apresentam uma ampla variedade de atividades biológicas, tais como: antiviral, citotóxica, antitumoral e analgésica. Neste trabalho, foram avaliados o perfil cromatográfico e a potencial atividade antiviral das frações diclorometano A e B, isoladas dos diferentes órgãos vegetais (bulbos, raízes, folhas e flores) de Hippeastrum glaucescens (Martius) Herbert, assim como dos alcalóides licorina, tazetina e pretazetina, previamente isolados desta planta. A extração dos alcalóides de H. glaucescens foi realizada por métodos clássicos, a partir de bulbos, raízes, folhas e flores fornecendo rendimentos totais em alcalóides de 0,53 por cento; 0,81 por cento; 0,29 por cento e 0,12 por cento, respectivamente. Empregando-se cromatografia em camada delgada, verificou-se que os bulbos e as raízes apresentam perfis cromatográficos semelhantes e que os alcalóides licorina, tazetina e pretazetina estão presentes em todas as partes testadas do vegetal. As frações diclorometano A e B, de cada órgão vegetal, e os alcalóides isolados (licorina, tazetina e pretazetina) não inibiram a replicação do herpesvírus simples humano tipo 1 (HSV-1) cepa KOS, quando avaliados através do método de inibição do efeito citopático viral.

Plants of Amaryllidaceae are characterized by isoquinoline alkaloids. Since the first study with Amaryllidaceae alkaloids in 1877, a large number of these plants have been chemically investigated. These compounds have shown a wide range of biological activities such as: antiviral, cytotoxic, antitumoral and analgesic. In this work, the dichloromethane (CH2Cl2) extracts obtained from different parts of the Hippeastrum glaucescens (Martius) Herbert (bulbs, roots, leaves and flowers) and the isolated alkaloids lycorine, tazettine and pretazettine were analyzed by a chromatographic method (TLC) and tested for antiviral activity. The extraction of alkaloids from bulbs, roots, leaves and flowers of H. glaucescens was performed by classic methods and yields 0.53 percent, 0.81 percent, 0.29 percent and 0.12 percent, respectively. Through TLC, bulbs and roots revealed similar chromatographic profiles and lycorine, tazettine and pretazettine were found in all the parts analyzed. The CH2Cl2-A and CH2Cl2-B extracts from each part of the plant and the isolated alkaloids (lycorine, tazettine and pretazettine) did not inhibit the HSV-1 strain KOS replication, when evaluated through the inhibition of cytophatic viral effect.