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The Alkaloids. Chemistry and Biology 2018This chapter covers the literature since the advent, in the 21st century, of total syntheses of alkaloids using enantio- or diastereoselective organocatalytic reactions... (Review)
Review
This chapter covers the literature since the advent, in the 21st century, of total syntheses of alkaloids using enantio- or diastereoselective organocatalytic reactions to construct the alkaloid scaffolds. The details of these alkaloid syntheses are described separately for each basic skeleton, including indole, indoline, oxindole, and piperidine alkaloids.
Topics: Alkaloids; Catalysis; Chemistry Techniques, Synthetic; Molecular Structure; Stereoisomerism
PubMed: 29455834
DOI: 10.1016/bs.alkal.2017.12.001 -
Annual Review of Plant Biology 2008Alkaloids represent a highly diverse group of compounds that are related only by the occurrence of a nitrogen atom in a heterocyclic ring. Plants are estimated to... (Review)
Review
Alkaloids represent a highly diverse group of compounds that are related only by the occurrence of a nitrogen atom in a heterocyclic ring. Plants are estimated to produce approximately 12,000 different alkaloids, which can be organized into groups according to their carbon skeletal structures. Alkaloid biosynthesis in plants involves many catalytic steps, catalyzed by enzymes that belong to a wide range of protein families. The characterization of novel alkaloid biosynthetic enzymes in terms of structural biochemistry, molecular and cell biology, and biotechnological applications has been the focus of research over the past several years. The application of genomics to the alkaloid field has accelerated the discovery of cDNAs encoding previously elusive biosynthetic enzymes. Other technologies, such as large-scale gene expression analyses and metabolic engineering approaches with transgenic plants, have provided new insights into the regulatory architecture of alkaloid metabolism.
Topics: Alkaloids; Isoquinolines; Kinetics; Models, Molecular; Plant Roots; Plants; Structure-Activity Relationship
PubMed: 18251710
DOI: 10.1146/annurev.arplant.59.032607.092730 -
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 -
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 -
The Alkaloids. Chemistry and Biology 2021This chapter provides a short overview of the history of morphine since it's isolation by Sertürner in 1805. The biosynthesis of the title alkaloid as well as all total... (Review)
Review
This chapter provides a short overview of the history of morphine since it's isolation by Sertürner in 1805. The biosynthesis of the title alkaloid as well as all total and formal syntheses of morphine and codeine published after 1996 are discussed in detail. The last section of this chapter provides a detailed overview of medicinally relevant derivatives of the title alkaloid.
Topics: Alkaloids; Biology; Codeine; Morphine
PubMed: 34565506
DOI: 10.1016/bs.alkal.2021.04.001 -
Organic & Biomolecular Chemistry Jan 2016Over the last decade, several excellent enantioselective total syntheses of important alkaloids using asymmetric reactions mediated by chiral secondary amine... (Review)
Review
Over the last decade, several excellent enantioselective total syntheses of important alkaloids using asymmetric reactions mediated by chiral secondary amine organocatalysts as a key step have been accomplished. This perspective article examines the full strategies of these alkaloid syntheses, especially the application of the organocatalytic reaction to construct the alkaloid scaffolds.
Topics: Alkaloids; Amines; Catalysis; Molecular Structure
PubMed: 26625722
DOI: 10.1039/c5ob02021b -
Molecules (Basel, Switzerland) Nov 2016The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties... (Review)
Review
The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties and their scattered distribution among angiosperms suggest that their biosynthesis may share common ancestry in some orders, while they may be independently derived in others. Tropane and granatane alkaloid diversity arises from the myriad modifications occurring to their core ring structures. Throughout much of human history, humans have cultivated tropane- and granatane-producing plants for their medicinal properties. This manuscript will discuss the diversity of their biological and ecological roles as well as what is known about the structural genes and enzymes responsible for their biosynthesis. In addition, modern approaches to producing some pharmaceutically important tropanes via metabolic engineering endeavors are discussed.
Topics: Alkaloids; Biosynthetic Pathways; Metabolic Engineering; Plant Extracts; Secondary Metabolism; Tropanes
PubMed: 27845728
DOI: 10.3390/molecules21111510 -
Current Opinion in Plant Biology Aug 2023Plants synthesize tens of thousands of bioactive nitrogen-containing compounds called alkaloids, including some clinically important drugs in modern medicine. The... (Review)
Review
Plants synthesize tens of thousands of bioactive nitrogen-containing compounds called alkaloids, including some clinically important drugs in modern medicine. The discovery of new alkaloid structures and their metabolism in plants have provided ways to access these rich sources of bioactivities including new-to-nature compounds relevant to therapeutic and industrial applications. This review discusses recent advances in alkaloid biosynthesis discovery, including complete pathway elucidations. Additionally, the latest developments in the production of new and established plant alkaloids based on either biosynthesis or semisynthesis are discussed.
Topics: Biosynthetic Pathways; Drug Repositioning; Alkaloids; Plants
PubMed: 37182414
DOI: 10.1016/j.pbi.2023.102379 -
Phytochemistry Jul 2013An overview is presented of the studies related to the biosynthesis of alkaloids published in Phytochemistry in the past 50 years. (Review)
Review
An overview is presented of the studies related to the biosynthesis of alkaloids published in Phytochemistry in the past 50 years.
Topics: Alkaloids; Plants
PubMed: 22721782
DOI: 10.1016/j.phytochem.2012.05.012 -
Current Opinion in Biotechnology Apr 2003The biosynthetic pathway of plant alkaloids is composed of several distinct enzymes of varying substrate specificities. Homology-based cloning of candidate genes and... (Review)
Review
The biosynthetic pathway of plant alkaloids is composed of several distinct enzymes of varying substrate specificities. Homology-based cloning of candidate genes and their subsequent functional testing in heterologous expression systems are accelerating the pace at which the gene catalogues of alkaloid biosynthesis are expanding. Availability of diverse genes involved in the biosynthesis, catabolism, transport, and regulation of pharmaceutically important alkaloids should steadily advance our molecular understanding of alkaloid biology and will enable us to devise more rational strategies for metabolic engineering.
Topics: Alkaloids; Biological Transport, Active; Cloning, Molecular; Gene Expression Regulation, Plant; Genetic Engineering
PubMed: 12732317
DOI: 10.1016/s0958-1669(03)00027-2