Isolation Of Alkaloids Research Articles

A Brief Up-to-Date Overview of Amaryllidaceae Alkaloids: Phytochemical Studies of Narcissus tazetta subsp. tazetta L., Collected in Turkey:

A brief up-to-date overview on the isolation, and chemical and biological characterization of new and known alkaloids from different Amaryllidaceae species, including Brunsvigia, Crinum, Cyrtanthus...

Isolation and structure elucidation of cyclopeptide alkaloids from the leaves of Heisteria parvifolia

Heisteria parvifolia Sm. is prescribed in traditional medecine against numerous diseases in Côte d'Ivoire. Due to the shortcoming in scientifical knowledge of use of this species, our investigations revealed five undescribed cyclopeptide alkaloids added to one known derivative namely anorldianine. These compounds were elucidated by 1D and 2D-NMR experiments and comparison with literature data, and confirmed by HR-ESI-MS. Cytotoxic activity evaluation of these compounds against the chronic myeloid leukemia (K565) cell line exhibited an antiproliferative activity with cell growth inhibition from 13% to 46%.

A Brief Up-to-Date Overview of Amaryllidaceae Alkaloids: Phytochemical Studies of Narcissus tazetta subsp. tazetta L., Collected in Turkey

A brief up-to-date overview on the isolation, and chemical and biological characterization of new and known alkaloids from different Amaryllidaceae species, including Brunsvigia, Crinum, Cyrtanthus, Narcissus, and Nerine genera, was reported. Furthermore, the isolation and chemical characterization of alkaloids extracted from bulbs of Narcissus tazetta subsp. tazetta L. collected from Muğla, Turkey were described.

Isolation of Alkaloids, Saponins and Tannins from Plants

Current study involves the detection and estimation of alkaloids, saponins and tannins in the 3 plant species vis., Oxalis debilis, Chenopodium vulvaria and Malva neglecta were taken as sample study. All the selected plant samples were brought to the labortary of university and were oven dried at 70°C. Following standard method of Eluyode and Alabithe, detection and estimation of alkaloid, saponin and tannin was carried out. The results showed variation in all the plant species of 3 families containing different concentration of alkaloids, saponins and tannins. The study symbolise the variation along with the level and concentration of alkaloids, saponins and tannins..

Purification of tertiary and quaternary alkaloids from Rhizoma Corydalis using reversed-phase/weak cation-exchange mixed-mode class separation combined with preparative C18 and silica based strong cation-exchange chromatography

A new optimization strategy for purification of alkaloids from Rhizoma Corydalis using preparative liquid chromatography was developed, featuring a selective separation of different types of alkaloids into different parts by a reversed-phase/weak cation-exchange mixed-mode column (named C18WCX) at first. The total alkaloids of Rhizoma Corydalis were divided into four fractions with fraction III and IV corresponding to the tertiary type medium bases and the quaternary type strong bases, respectively. For fraction III, a conventional C18 column was used to isolate tertiary alkaloids using acetonitrile and 0.1% phosphoric acid (adjusted with triethylamine to pH 6.0) as mobile phases. High selectivity and symmetrical peak shapes of tertiary alkaloids were obtained, resulting in six main tertiary alkaloids isolated in a single run. As strong bases, quaternary alkaloids often suffer from serious peak tailing problem on conventional C18 columns. Therefore, a silica-based strong cation-exchange (SCX) column was used for purification of fraction IV. On the SCX column, good peak shapes in high sample loading were achieved. Five main quaternary alkaloids were isolated and identified from the fraction in one-step. The procedures presented effective for the preparative isolation and purification of alkaloids from Rhizoma Corydalis.

Utilization of electrocoagulation for the isolation of alkaloids from the aerial parts of Stemona aphylla and their mosquitocidal activities against Aedes aegypti

The electrocoagulation (EC) technique is an alternative method of isolating natural products with the advantage of minimizing the amounts of organic solvents required for this process, which are often harmful to the environment. In this research, the EC and the conventional solvent extraction methods were used in the isolation of Stemona alkaloids from the aerial parts of Stemona aphylla. A comparison was made between the amounts of the isolated alkaloids and the solvents used. The isolated alkaloids were evaluated for their larvicidal, ovicidal and oviposition-deterrent activities against the dengue vector, Aedes aegypti. The morphology and histopatology of the alkaloid treated larvae were also investigated. Two Stemona alkaloids, (2′S)-hydroxystemofoline and stemofoline, were isolated from both the EC and the conventional method. The amounts of (2′S)-hydroxystemofoline from the EC method was about the same as that obtained from the conventional method. However, the amounts of stemofoline obtained from the EC method were about two times larger than those obtained from the conventional method. Importantly, the EC method required six times less total organic solvents. The larvicidal activity assays of (2′S)-hydroxystemofoline and stemofoline showed that these were highly effective against Aedes aegypti larvae with LC50 values of 3.91 μg/ml and 4.35 μg/ml, respectively. Whereas, the crude EC extract (LC50 = 11.86 μg/ml) showed greater larvicidal activity than the crude extract obtained from the conventional extraction method (LC50 = 53.40 μg/ml). The morphological observations of the (2′S)-hydroxystemofoline and the stemofoline treated larvae revealed that the anal gills were the sites of aberrations. A histopathological study showed that larvae treated with these alkaloids had cytopathological alterations to the epithelial cells of the midgut. At a concentration 40 μg/ml (2′S)-hydroxystemofoline showed 100% ovicidal activity on 24 h old eggs while stemofoline showed 97.2%. Furthermore, the oviposition-deterrent effects of (2′S)-hydroxystemofoline and stemofoline, at a concentration of 80 μg/ml were 99.5% and 97.2%, respectively.

Isolation of Oxoaphorpine Alkaloid from Bark of Cryptocarya Ferrea

Isolation of Oxoaphorpine Alkaloid from Bark of Cryptocarya Ferrea

Cytotoxic and Genotoxic Activities of Alkaloids from the Bulbs of Griffinia gardneriana and Habranthus itaobinus (Amaryllidaceae).

Amaryllidaceae plants are known to be a great source of alkaloids, which are considered an extensive group of compounds encompassing a wide range of biological activities. The remarkable cytotoxic activities observed in most of the Amaryllidaceae alkaloids derivatives have prompt the chemical and biological investigations in unexplored species from Brazil. To evaluate the cytotoxic and genotoxic properties of alkaloids of Griffinia gardneriana and Habranthus itaobinus bulbs and study the role of caspase-3 as a molecular apoptosis mediator. Methanolic crude extracts of Griffinia gardneriana and Habranthus itaobinus bulbs were submitted to acid-base extraction to obtain alkaloid-enriched fractions. The obtained fractions were fractionated using chromatographic techniques leading to isolation and identification of some alkaloids accomplished via HPLC and 1H-NMR, respectively. Molecular docking studies assessed the amount of free binding energy between the isolated alkaloids with the caspase-3 protein and also calculated the theoretical value of Ki. Studies have also been developed to evaluate in vitro cytotoxicity and genotoxicity in such alkaloids and apoptosis activation via the caspase pathway using both tumor and normal cell lines. Seven alkaloids were isolated and identified. Among these, 11-hydroxyvittatine and 2-α-7- dimethoxyhomolycorine were not cytotoxic, whereas tazettine, trisphaeridine, and sanguinine only showed activity against the fibroblast lineage. Lycorine and pretazettine were 10 to 30 folds more cytotoxic than the other alkaloids, including cancerous lines, and were genotoxic and capable of promoting apoptosis via the caspase-3 pathway. This result supports data obtained in docking studies wherein these two compounds exhibited the highest free energy values. The cytotoxicity assay revealed that, among the seven alkaloids isolated, only lycorine and pretazettine were active against different cell lines, exhibiting concentration- and time-dependent cytotoxic actions alongside genotoxic action and the ability to induce apoptosis by caspase-3, a result consistent with those obtained in docking studies.

Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea

Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC50 = 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.

Proteome study of embryogenic competence acquisition in the callus cultures of Nothapodytes nimmoniana (J. Graham) Mabberly

Among the alternative plant sources of camptothecin (CPT), Nothapodytes nimmoniana is regarded as the most convenient source for large-scale isolation of the monoterpenoid indole anticancer alkaloid. As a result, CPT annual trade value has grossed over billion US Dollars in recent years. Somatic embryogenesis (SE) offers potential application in the rapid clonal propagation of the tree and production of the alkaloid, so as to mitigate indiscriminate harvest of its endangered natural population to meet industrial demand. However, response to the production of embryogenic callus (EC) in the in vitro cultures of N. nimmoniana is poor to scant. In the present study, two-dimensional electrophoresis (2-DE) and mass spectrometry (MaSp/MaSp) were employed in studying proteome expression changes between EC and non-embryogenic callus (NEC) of the forest tree. The results of the study showed higher metabolic and physiological processes associated with embryogenic competence acquisition in the callus cultures; high cellular oxidative stress, energy metabolism, protein synthesis, and other metabolic processes played a key role in upregulated expression of the identified proteins in EC over NEC. Putative role of the expressed proteins during embryogenic competence acquisition by N. nimmoniana callus cultures has provided some insight into the physiology of the competence acquisition through cellular roles played by oxidative stress and metabolic processes. Further studies on metabolic physiological processes associated with EC production could have application in optimizing culture conditions for mass propagation through the SE, so as to mitigate the indiscriminate harvest of endangered N. Nimmoniana natural population for CPT.

Isolation and Identification of Alkaloids from Poisons of Fire Salamanders ( Salamandra salamandra).

Fire salamanders ( Salamandra salamandra) are conspicuously colored amphibians secreting a skin poison that contains unique steroid alkaloids such as samandarine (1) and samadarone (2), exhibiting toxic as well as antimicrobial activities. Because of their antipredatory and anti-infectious functions, alkaloids from Salamandra poison are of interest with regard to the threat that the lethal fungus Batrachochytrium salamandrivorans ( Bsal) poses to salamanders. Nevertheless, reliable data on the biological activity of Salamandra alkaloids are scarce, in part due to the difficulty to obtain and study those substances. Thus, isolation of pure salamander alkaloids is an important task that might directly contribute to the understanding of Bsal infections. Here we present a noninvasive isolation procedure for samandarine (1) and O-acetylsamandarine (3), as well as for two new alkaloids, O-3-hydroxybutanoylsamandarine (4) and samanone (6), using HPLC. For the first time, high-field NMR data are presented for these alkaloids. Analysis using GC/MS and ESI+-MS, provided important information on the structural variability of these salamander alkaloids.

Isolation of erythrinan alkaloids from the leaves and flowers of Erythrina speciosa

In this paper, we describe the extraction of three alkaloids from the leaves and flowers of Erythrina speciosa, a plant documented in the literature to possess a range of potential medicinal applications. Two alkaloids were isolated from both leaves and flowers, with erythrartine being isolated from both plant parts. In agreement with the literature, we also isolated erysotrine from the flowers. The second alkaloid isolated from the leaves, and reported in this species for the first time, was (+)-11β-hydroxyerysotramidine.

ISOLATION OF BENZOPHENANTHRIDINE ALKALOIDS FROM MACLEAYA LEAVES WITHOUT USING TOXIC SOLVENTS

This study aims to develop a new method for isolation of benzophenanthridine alkaloids from Macleaya leaves, which do not use toxic or ecologically dangerous solvents or reagents. According to this method, the extraction of alkaloids from the plant material is performed with 90% ethanol by percolation at 40±2 °C until 5–8 parts (V/M) of extract is obtained. The extract is acidified with sulphuric acid to pH 4.0–4.5 for sedimentation of ballast substances. After filtration or centrifugation, sulphuric acid is added to the extract to obtain the concentration of 0.1–0.12 M. Crystallisation of bisulphates of alkaloids occurs during 14 days at room temperature, then is finished in 7 days at 2–8 °C. The crude product is separated by filtration, washed with 96% ethanol and dried.
 Upon purification, alkaloids pass into a concentrated aqueous solution in the form of sulphates. A major part of impurities is removed by sedimentation, the remainder – by sorption on activated carbon. Than alkaloids are crystallised again in the form of bisulphates or other salts as required.
 The procedure has been created to obtain the sum of benzophenanthridine alkaloids of Macleaya in form of salicylates. This substance, named "Sanguirisal", is proposed as an active substance for preparation of pharmaceutical forms for topic administration, being much more lipophilic than sanguiritrine.

Phytochemical and pharmacological activities of Solanum surattense Burm. f.–A review

Medicinal plants are unique in having the ability to produce diverse chemical compounds with remarkable biological activities. Investigations of medicinal plants resulted in the discovery of a large number of bioactive compounds with excellent therapeutic properties. Solanum surattense, a perennial wild growing medicinal herb, widely used in traditional medicine. Exhaustive literature availability reveals the presence of phytochemical compounds from different plant parts like roots, stem, leaves, fruits and seeds and also reported to possess a wide range of pharmacological activities, like, hepatoprotective, cardioprotective, antiasthmatic and mosquito repellents properties. Intensive investigation on phytochemical constituents resulted in isolation of alkaloid and steroidal compounds Solasonoine, solamargine, Campesterol & diosgenin. Evaluation of therapeutic activity of isolated compounds proved as potent ones with reference to standard. Current literature on pharmacological activity of S. surattense confirms the scientific validation of folklore claims and its traditional use to cure various ailments. Present review is undertaken to summarize all the available information on pharmacological activities, which provide a baseline support for further exploration of its unexplored therapeutic effects like immunomodulation, antipiles activity, antianaphylactic activity and sexual behavior claimed by folklore.

LC-MS guided isolation and dereplication of Lycopodium alkaloids from Lycopodium cernuum var. sikkimense of different geographical origins

Lycopodium alkaloids (LAs) are the characteristic metabolites of club mosses. Chemical differences often exist in different specimens of a single plant species collected from different geographic origins. In this study, a preliminary LC-MS detection and dereplication analyses of alkaloidal constituents of Lycopodium cernuum var. sikkimense (Müll. Hal.) C.B. Clarke (LCVS2) collected from Fujian province led to the isolation and characterization of three undescribed LAs, lycocernuskines A–C, and six known cernuane-type LAs. The known compounds were previously isolated from the same plant species (LCVS1) collected from Chongqing, and so their dereplication in LCVS2 was accomplished based on their retention times (tR) and the quasi-molecular ion peaks in the LC-MS fingerprint. Chemical structures were identified by spectroscopic methods, single-crystal X-ray diffraction analysis, and electronic circular dichroism calculations. Lycocernuskines A and B are the first two examples of C-12 hydroxylated phlegmarane-type LAs bearing a nitrone residue at the quinoline ring. The isolates were evaluated for their anti-AChE and neuroprotective effects.

Isolation, Purification and Complex Formation of Nicotine Alkaloid

Isolation, Purification and Complex Formation of Nicotine Alkaloid

Morphinandienone and aporphine alkaloids from Corydalis decumbens

Phytochemical examination of Corydalis decumbens has afforded two new morphinandienone alkaloids, namely, (-)-pallidine N-oxide (1) and (-)-salutaridine N-oxide (2), together with one known analogue, (-)-pallidine (3), and three known aporphine alkaloids (4−6). Their structures were elucidated via comprehensive spectroscopic analysis and chemical correlation. This study represents the first isolation of morphinandienone alkaloids from the title plant. All isolates were tested for their activities towards neuronal excitability in primary cultured neocortical neurons.

Isolation of indole alkaloid and anthranilic acid derivatives from Indigo Pulverata Levis

A new indole alkaloid, pulveratinol (1), and two new anthranilic acid derivatives (2 and 3) were isolated from Indigo Pulverata Levis, together with 12 known compounds (4–15). The structures of the new compounds (1–3) were determined through spectroscopic methods. The absolute configuration of 1 was confirmed further by electronic circular dichroism (ECD) data analysis and computational method with advanced statistics (DP4). All isolated compounds (1–15) were evaluated for their potential neuroprotective effects through induction of nerve growth factor (NGF) in C6 glioma cells.

Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS.

To assess the antiplasmodial activity of the ethanol extract of Xylopia sericea leaves, Annonaceae, often associated with antimalarial use and to perform a bioguided isolation of active compounds. Dereplication of ethanol extract by the UPLC-DAD-ESI-MS/MS technique allowed the identification of the major constituents, isolation and identification of alkaloids. The antiplasmodial and cytotoxic activity of the extract, fractions and isolated compounds was evaluated against the chloroquine-resistant W2 strain Plasmodium falciparum and HepG2 cells, respectively. Ethanol extract showed high reduction of parasitemia as well as moderate cytotoxicity (86.5±3.0% growth inhibition at 50μg/ml and CC50 72.1±5.1μg/ml, respectively). A total of eight flavonoids were identified, and two aporphine alkaloids, anonaine and O-methylmoschatoline, were isolated. Anonaine disclosed significant antiplasmodial effect and moderate cytotoxicity (IC50 23.2±2.7μg/ml, CC50 38.3±2.3μg/ml, SI 1.6) while O-methylmoschatoline was not active against P.falciparum and showed a low cytotoxicity (33.5±1.9% growth inhibition at 50μg/ml, CC50 274.4±0.5μg/ml). Characterization of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS as well as its antiplasmodial activity and the occurrence of anonaine and O-methylmoschatoline in this Xylopia species are reported by the first time.

DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective.

Opium is the latex from the opium poppy Papaver somniferum L., which humankind has utilized since ancient Mesopotamia all the way to modern times. Opium used to be surrounded in divine mystery or magic-like abilities and was given to cure a wide variety of diseases until its analgesic, antitussive, and antidiarrheal properties were understood, the resulting alkaloids were isolated, and their structure and properties unmasked. Opium went from being sold in any store front in the form of pills or tinctures with no prescription necessary for purchase or smoked in an opium den down the street, to then bringing about consumer advocacy and the right to know what is in a medication. Legislation was created to limit the prescribing and selling of medications to doctors and pharmacists as well as outlawing opium dens and smoking opium. This review focuses primarily on the uses of opium throughout history, the isolation of the principle alkaloids, and their structure elucidation.