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BMC Research Notes Sep 2021Papaver decaisnei Hochst. & Steud. Ex Elkan and Papaver glaucum Boiss. & Hausskn. growing wild in Northern Iraq have been historically used for medicinal purposes. In...
OBJECTIVE
Papaver decaisnei Hochst. & Steud. Ex Elkan and Papaver glaucum Boiss. & Hausskn. growing wild in Northern Iraq have been historically used for medicinal purposes. In this study, both species were evaluated for their alkaloid content and antimicrobial activities.
RESULTS
Alkaloids were extracted and isolated by preparative thin-layer chromatography (TLC). Identification was carried out by comparing spectral data (UV and H-NMR) and TLC Rf values with those of authentic samples. Two alkaloids, proapaorphine-type mecambrine and aporphine-type roemerine were isolated from P. decaisnei. Two benzylisoquinoline type alkaloids papaverine (major alkaloid) and palaudine as well as aporphine-type N-methylasimilobine have been obtained in P. glaucum. Both P. glaucum and P. decaisnei extracts revealed strong antimicrobial activity on Pseudomonas aeruginosa ATCC 27853 and Enterococcus faecalis ATCC 29212. Collectively these results indicate that P. glaucum and P. decaisnei are promising sources of alkaloids that could further be investigated for medicinal purposes.
Topics: Alkaloids; Anti-Infective Agents; Chromatography, Thin Layer; Papaver; Plant Extracts
PubMed: 34496958
DOI: 10.1186/s13104-021-05762-x -
Natural Product Reports Jan 2021Alkaloids from plants are characterised by structural diversity and bioactivity, and maintain a privileged position in both modern and traditional medicines. In recent... (Review)
Review
Alkaloids from plants are characterised by structural diversity and bioactivity, and maintain a privileged position in both modern and traditional medicines. In recent years, there have been significant advances in elucidating the biosynthetic origins of plant alkaloids. In this review, I will describe the progress made in determining the metabolic origins of the so-called true alkaloids, specialised metabolites derived from amino acids containing a nitrogen heterocycle. By identifying key biosynthetic steps that feature in the majority of pathways, I highlight the key roles played by modifications to primary metabolism, iminium reactivity and spontaneous reactions in the molecular and evolutionary origins of these pathways.
Topics: Aldehydes; Alkaloids; Amines; Amino Acids; Biosynthetic Pathways; Enzymes; Evolution, Molecular; Plant Proteins; Plants
PubMed: 32745157
DOI: 10.1039/d0np00031k -
Mini Reviews in Medicinal Chemistry 2021Pityriacitrin is a natural marine alkaloid with a typical β-carboline scaffold, and which has been demonstrated to exhibit diverse biological functions. The special... (Review)
Review
Pityriacitrin is a natural marine alkaloid with a typical β-carboline scaffold, and which has been demonstrated to exhibit diverse biological functions. The special structural features for pityriacitrin lead to the increasing research interest and the emergence of versatile derivatives, and many pityriacitrin analogues have been isolated or synthesized over the past decades. The structural diversity and evolved biological activity of these natural alkaloids can offer opportunities for the development of highly potential novel drugs with a new mechanism of action, and therefore, the aim of this brief review is to describe the discovery, synthesis, and biological properties of natural pityriacitrin and its derivatives, as well as the isolation source.
Topics: Alkaloids; Antineoplastic Agents; Antioxidants; Cell Survival; Drug Evaluation, Preclinical; Humans; Indole Alkaloids; Receptors, Aryl Hydrocarbon; Signal Transduction; Structure-Activity Relationship
PubMed: 33200706
DOI: 10.2174/1389557520666201116144156 -
The Journal of Organic Chemistry Jun 2022Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical, and efficient (= short) synthetic pathways is of...
Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical, and efficient (= short) synthetic pathways is of high interest in organic chemistry. Here, we describe an operationally simple and short synthesis of the privileged scaffold dihydropyrrolo[1,2-]pyrazine-dione from readily accessible starting materials. The alkaloid-type polycyclic scaffold with potential bioactivity was achieved by a multicomponent reaction (MCR)-based protocol via a Ugi four-component reaction and Pictet-Spengler sequence under different conditions, yielding a diverse library of products.
Topics: Alkaloids
PubMed: 35549475
DOI: 10.1021/acs.joc.2c00244 -
Natural Product Research Oct 2019A new aporphine glycoside, (-)anolobine-9-D-glucopyranoside was isolated from the twigs of pawpaw () along with 7 known alkaloids including five aporphine alkaloids...
A new aporphine glycoside, (-)anolobine-9-D-glucopyranoside was isolated from the twigs of pawpaw () along with 7 known alkaloids including five aporphine alkaloids (anolobine, nornuciferine, norushinsunine, liriodenine, and lysicamine), a proaporhine alkaloid (stepharine), and a tetrahydrobenzylisoquinoline alkaloid (coclaurine). Among these compounds, nornuciferine, lysicamine, stepharine, and coclaurine are reported for the first time from this plant. The structure of the new compound was elucidated by spectroscopic methods, including 1 D, 2 D NMR, and HRESI-MS. The absolute configuration of compounds , , and was determined by CD experiment.
Topics: Alkaloids; Aporphines; Asimina; Isoquinolines; Magnetic Resonance Spectroscopy; Molecular Structure; Spectrometry, Mass, Electrospray Ionization
PubMed: 30453785
DOI: 10.1080/14786419.2018.1504045 -
Phytochemistry Dec 2023Crinum x powellii 'Album' belongs to the Amaryllidaceae medicinal plant family that produces a range of structurally diverse alkaloids with potential therapeutic...
Crinum x powellii 'Album' belongs to the Amaryllidaceae medicinal plant family that produces a range of structurally diverse alkaloids with potential therapeutic properties. The optimal conditions for in vitro tissue growth, morphogenesis, and alkaloid biosynthesis remain unclear. Auxin and light play critical roles in regulating plant growth, development, and alkaloid biosynthesis in several Amaryllidaceae plants. Here, we have succeeded in showing, for the first time, that the combination of auxin and light significantly influence C. x powellii "Album" in vitro tissue growth, survival, and morphogenesis compared to individual treatments. Furthermore, this combination also upregulates the expression of alkaloid biosynthetic genes and led to an increase in the content of certain alkaloids, suggesting a positive impact on the defense and therapeutic potential of the calli. Our findings provide insights into the regulation of genes involved in alkaloid biosynthesis in C. x powellii "Album" callus and underline the potential of auxin and light as tools for enhancing their production in plants. This study provides a foundation for further exploration of C. x powellii "Album" calli as a sustainable source of bioactive alkaloids for pharmaceutical and agricultural applications. Furthermore, this study paves the way to the discovery of the biosynthetic pathway of specialized metabolites from C. x powellii "Album", such as cherylline and lycorine.
Topics: Crinum; Indoleacetic Acids; Amaryllidaceae Alkaloids; Alkaloids; Plant Extracts; Morphogenesis
PubMed: 37820888
DOI: 10.1016/j.phytochem.2023.113883 -
Molecules (Basel, Switzerland) Jul 2023The natural alkaloid gramine has attracted significant attention in both academic and industrial circles because of its potential and diverse biological activities,... (Review)
Review
The natural alkaloid gramine has attracted significant attention in both academic and industrial circles because of its potential and diverse biological activities, including antiviral, antibacterial, antifungal, anti-inflammatory and antitumor activities; application in therapy for Alzheimer's disease; serotonin-receptor-related activity; insecticidal activity; and application as an algicide. In this review, we focus on the research advances that have been made for gramine-based molecules since their discovery, providing key information on their extraction and separation, chemical synthesis and diverse biological activities. Data regarding their mechanisms of action are also presented. This comprehensive and critical review will serve as a guide for developing more drug candidates based on gramine skeletons.
Topics: Indole Alkaloids; Alkaloids
PubMed: 37570664
DOI: 10.3390/molecules28155695 -
Molecules (Basel, Switzerland) Jul 2023Cancer is a neoplastic disease that remains a global challenge with a reported prevalence that is increasing annually. Though existing drugs can be applied as single or... (Review)
Review
Cancer is a neoplastic disease that remains a global challenge with a reported prevalence that is increasing annually. Though existing drugs can be applied as single or combined therapies for managing this pathology, their concomitant adverse effects in human applications have led to the need to continually screen natural products for effective and alternative anticancer bioactive principles. Alkaloids are chemical molecules that, due to their structural diversity, constitute a reserve for the discovery of lead compounds with interesting pharmacological activities. Several in vitro studies and a few in vivo findings have documented various cytotoxic and antiproliferative properties of alkaloids. This review describes chaetocochin J, neopapillarine, coclaurine, reflexin A, 3,10-dibromofascaplysin and neferine, which belong to different alkaloid classes with antineoplastic properties and have been identified recently from plants. Despite their low solubility and bioavailability, plant-derived alkaloids have viable prospects as sources of viable lead antitumor agents. This potential can be achieved if more research on these chemical compounds is directed toward investigating ways of improving their delivery in an active form close to target cells, preferably with no effect on neighboring normal tissues.
Topics: Humans; Alkaloids; Antineoplastic Agents; Neoplasms; Plant Extracts
PubMed: 37513450
DOI: 10.3390/molecules28145578 -
Nature Dec 2023Plants synthesize numerous alkaloids that mimic animal neurotransmitters. The diversity of alkaloid structures is achieved through the generation and tailoring of unique...
Plants synthesize numerous alkaloids that mimic animal neurotransmitters. The diversity of alkaloid structures is achieved through the generation and tailoring of unique carbon scaffolds, yet many neuroactive alkaloids belong to a scaffold class for which no biosynthetic route or enzyme catalyst is known. By studying highly coordinated, tissue-specific gene expression in plants that produce neuroactive Lycopodium alkaloids, we identified an unexpected enzyme class for alkaloid biosynthesis: neofunctionalized α-carbonic anhydrases (CAHs). We show that three CAH-like (CAL) proteins are required in the biosynthetic route to a key precursor of the Lycopodium alkaloids by catalysing a stereospecific Mannich-like condensation and subsequent bicyclic scaffold generation. Also, we describe a series of scaffold tailoring steps that generate the optimized acetylcholinesterase inhibition activity of huperzine A. Our findings suggest a broader involvement of CAH-like enzymes in specialized metabolism and demonstrate how successive scaffold tailoring can drive potency against a neurological protein target.
Topics: Animals; Acetylcholinesterase; Alkaloids; Carbonic Anhydrases; Cholinesterase Inhibitors; Gene Expression Regulation, Plant; Models, Neurological; Neurotransmitter Agents; Plants; Sesquiterpenes; Lycopodium
PubMed: 37938780
DOI: 10.1038/s41586-023-06716-y -
Microbial Biotechnology Apr 2023Ergot alkaloids are a large family of fungal specialized metabolites that are important as toxins in agriculture and as the foundation of powerful pharmaceuticals. Fungi... (Review)
Review
Ergot alkaloids are a large family of fungal specialized metabolites that are important as toxins in agriculture and as the foundation of powerful pharmaceuticals. Fungi from several lineages and diverse ecological niches produce ergot alkaloids from at least one of several branches of the ergot alkaloid pathway. The biochemical and genetic bases for the different branches have been established and are summarized briefly herein. Several pathway branches overlap among fungal lineages and ecological niches, indicating activities of ergot alkaloids benefit fungi in different environments and conditions. Understanding the functions of the multiple genes in each branch of the pathway allows researchers to parse the abundant genomic sequence data available in public databases in order to assess the ergot alkaloid biosynthesis capacity of previously unexplored fungi. Moreover, the characterization of the genes involved in the various branches provides opportunities and resources for the biotechnological manipulation of ergot alkaloids for experimentation and pharmaceutical development.
Topics: Ergot Alkaloids; Fungi
PubMed: 36636806
DOI: 10.1111/1751-7915.14214