Search results for " alkaloids"

Pharmacology of Ischemia-Reperfusion. Translational Research Considerations.

2016

Ischemia-reperfusion (IRI) is a complex physiopathological mechanism involving a large number of metabolic processes that can eventually lead to cell apoptosis and ultimately tissue necrosis. Treatment approaches intended to reduce or palliate the effects of IRI are varied, and are aimed basically at: inhibiting cell apoptosis and the complement system in the inflammatory process deriving from IRI, modulating calcium levels, maintaining mitochondrial membrane integrity, reducing the oxidative effects of IRI and levels of inflammatory cytokines, or minimizing the action of macrophages, neutrophils, and other cell types. This study involved an extensive, up-to-date review of the bibliography …

Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methox…

2013

The Stevens rearrangement of nitrile-stabilized ammonium ylides in conjunction with the reductive removal of the nitrile function permits the facile construction of α-branched amines from α-aminonitriles. We employed this reaction sequence for the preparation of (±)-laudanosine, (±)-laudanidine and (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine from two closely related and readily accessible bicyclic α-aminonitriles. The final products were obtained in high to almost quantitative yields (71–98%) from the quaternary ammonium salts obtained by N-alkylation of these starting materials.

Die direkte quantitative Auswertung von Dünnschichtchromatogrammen durch Remissions- und Fluoreszenzmessungen 3. Mitt.: Bestimmung von Morphin, Codei…

1971

Es wird ein Verfahren zur quantitativen Bestimmung verschiedener Opiumalkaloide nebeneinander beschrieben, das auf der direkten Auswertung von DC durch Remissionsmessung mit Hilfe eines Chromatogramm-Spektralphotometers beruht. Anstelle des bisher ublichen Messpaltes wurde fur die Auswertung eine Kreisblende benutzt. Hierbei ist vorteilhaft, das die Form der Absorptions-Orts-Kurven keinen Einflus auf die Mesgenauigkeit besitzt, da nur die Peakhohe ausgewertet wird. Quantitative Determination of Opium Alkaloids A method for the quantitative determination of a number of single alkaloids in opium alkaloid mixtures is described, which is based on the direct evaluation of TLC by reflectance with…

Therapeutic potential of alkaloids in autoimmune diseases: Promising candidates for clinical trials.

2020

Clinical investigations have characterized numerous disorders like autoimmune diseases, affecting the population at a rate of approximately 8-10%. These disorders are characterized by T-cell and auto-antibodies responses to self-molecules by immune system reactivity. Several therapeutic options have been adopted in clinics to combat such diseases, however, most of them are recurring. Thus, the discovery of new effective agents for the treatment of autoimmune diseases is paramount. In this context, natural products might be a useful alternative to the current therapies. Plant alkaloids with their substantial therapeutic history can be particularly interesting candidates for the alleviation o…

Mikrobiologische C-17-Oxidation von Clavinalkaloiden

1984

Metabolomics-assisted discovery of a new anticancer GLS-1 inhibitor chemotype from a nortopsentin-inspired library: From phenotype screening to targe…

2022

The enzyme glutaminase-1 (GLS-1) has shown a clear and coherent implication in the progression and exacerbation of different aggressive tumors such as glioblastoma, hepatocarcinoma, pancreas, bone, and triple-negative breast cancer. Few chemotypes are currently available as selective GLS-1 inhibitors, and still, fewer of them are at the clinical stage. In the present paper, starting from a naturally-inspired antitumor compound library, metabolomics has been used to putatively identify the molecular mechanism underlying biological activity. GLS-1 was identified as a potential target. Biochemical analysis confirmed the hypothesis leading to the identification of a new hit compound acting as a…

Cytotoxicity of ungeremine towards multi-factorial drug resistant cancer cells and induction of apoptosis, ferroptosis, necroptosis and autophagy

2018

Abstract Background Successful cancer chemotherapy is hampered by resistance of cancer cells to established anticancer drugs. Numerous natural products reveal cytotoxicity towards tumor cells. Purpose The present study was aimed to determine the cytotoxicity of a betaine-type alkaloid, ungeremine, towards 9 cancer cell lines including various sensitive and drug-resistant phenotypes. The mode of action of this compound was further investigated. Methods The cytotoxicity, ferroptotic and necroptotic cell death were determined by the resazurin reduction assay. Caspase activation was evaluated using the caspase-Glo assay. Flow cytometry was applied for the analysis of cell cycle analysis (PI sta…

A one-pot cascade to protoberberine alkaloids via Stevens rearrangement of nitrile-stabilized ammonium ylides.

2015

A facile one-pot synthesis of protoberberines from readily accessible 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles and 1,2-bis(bromomethyl)arenes is described. The reaction cascade comprises four consecutive transformations, all of which can be effected under a single set of conditions. Ten protoberberines, including the alkaloids pseudopalmatine and pseudoepiberberine, were prepared in yields up to 86% according to this strategy. No chromatographic purification of the products is required, and the route is devoid of any protecting group manipulations.

Molecular cloning and functional bacterial expression of a plant glucosidase specifically involved in alkaloid biosynthesis.

2000

Monoterpenoid indole alkaloids are a vast and structurally complex group of plant secondary compounds. In contrast to other groups of plant products which produce many glycosides, indole alkaloids rarely occur as glucosides. Plants of Rauvolfia serpentina accumulate ajmaline as a major alkaloid, whereas cell suspension cultures of Rauvolfia mainly accumulate the glucoalkaloid raucaffricine at levels of 1.6 g/l. Cell cultures do contain a specific glucosidase. known as raucaffricine-O-beta-D-glucosidase (RG), which catalyzes the in vitro formation of vomilenine, a direct intermediate in ajmaline biosynthesis. Here, we describe the molecular cloning and functional expression of this enzyme in…

Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling

2021

The morphinans are an important class of structurally fascinating and physiologically important natural products as exemplified by the famous opium alkaloids of the morphine family. Although this class of secondary metabolites from the juice of the opium poppy capsule was already used for medicinal purposes thousands of years ago, chemical modifications are still being applied to the core structure today in order to achieve the most specific effect on the various receptor subtypes possible with the fewest possible side effects. The unusual architecture of the morphinan core has also proven to be a highly challenging target for total synthesis. This review highlights electrosynthetic approac…