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tropane alkaloids

Monika Asztemborska, Magdalena Ceborska, Mariusz Pietrzak
Complexes of atropine, homatropine, scopolamine, and ipratropium with cyclodextrins were investigated by NMR and capillary electrophoresis. It has been demonstrated that tropane alkaloids form complexes with β- and γ-cyclodextrins of 1:1 stoichiometry. NMR measurements indicate the formation of complexes where both aliphatic and aromatic parts of tropane alkaloids interact with β-cyclodextrin. The stability constants of the investigated alkaloids with β- and γ-cyclodextrins were determined by capillary electrophoresis...
April 1, 2019: Carbohydrate Polymers
Jesús Marín-Sáez, Roberto Romero-González, Antonia Garrido Frenich
Cereal based foods are a major part of the infant diet and they can be contaminated with Solanaceae and other plants containing tropane alkaloids. This study was focused on the optimisation of an extraction procedure based on a solid-liquid method and an online SPE system, directly coupled to different mass spectrometry analysers as Orbitrap and triple quadrupole (QqQ), removing the chromatographic separation step. Total running analysis time was 15.8 min (17.3 min in the QqQ system). The developed method was validated obtaining recoveries ranging from 66 to 98% and 68-97% for the Orbitrap and QqQ respectively (RSD lower than 14...
March 1, 2019: Food Chemistry
Emily E Wrenbeck, Matthew A Bedewitz, Justin R Klesmith, Syeda Noshin, Cornelius S Barry, Timothy A Whitehead
Enzymes are the ultimate entities responsible for chemical transformations in natural and engineered biosynthetic pathways. However, many natural enzymes suffer from suboptimal functional expression due to poor intrinsic protein stability. Further, stability enhancing mutations often come at the cost of impaired function. Here we demonstrate an automated protein engineering strategy for stabilizing enzymes while retaining catalytic function using deep mutational scanning coupled to multiple-filter based screening and combinatorial mutagenesis...
February 8, 2019: ACS Synthetic Biology
Yu Ping, Xiaodong Li, Baofu Xu, Wei Wei, Wenping Wei, Guoyin Kai, Zhihua Zhou, Youli Xiao
N-Methylpyrrolinium-derived alkaloids like tropane alkaloids, nicotine, and calystegines are valuable plant source specialized metabolites bearing pharmaceutical or biological activity. Microbial synthesis of the critical common intermediate N-methylpyrrolinium would allow for sustainable production of N-methylpyrrolinium-derived alkaloids. Here, we achieve the production of N-methylpyrrolinium both in Escherichia coli and in Saccharomyces cerevisiae by employing the biosynthetic genes derived from three different plants...
January 31, 2019: ACS Synthetic Biology
Samson Afewerki, Jia-Xin Wang, Wei-Wei Liao, Armando Córdova
Tropanes are an important class of alkaloid natural products that are found in plants all over the world. These compounds can exhibit significant biological activity and are among the oldest known medicines. In the early 19th century, tropanes were isolated, characterized, and synthesized by notable chemical researchers. Their significant biological activities have inspired tremendous research efforts toward their synthesis and the elucidation of their pharmacological activity both in academia and in industry...
2019: Alkaloids. Chemistry and Biology
Nana Du, Weijia Zhou, Hongli Jin, Yanfang Liu, Han Zhou, Xinmiao Liang
Scopolia tangutica is a traditional Chinese medicine used for antispasmodic, anesthesia, analgesia and sedation. Its medicinal activity is associated to alkaloid constituents, including tropane and cinnamamide types. Low content of alkaloids in plant makes them difficult to be isolated and identified. The present work developed an effective method to quickly characterize alkaloids from Scopolia tangutica by HPLC coupled with quadrupole time-of-flight tandem mass spectrometry. Thirteen reference compounds were studied for their fragmentation pathways, including five tropane alkaloids and eight cinnamamide ones...
January 14, 2019: Journal of Separation Science
Abigail Moreno-Pedraza, Ignacio Rosas-Román, Nancy Shyrley García-Rojas, Héctor Guillén-Alonso, Cesaré Ovando-Vázquez, David Díaz-Ramírez, Jessica Cuevas-Contreras, Fredd Vergara, Nayelli Marsch-Martínez, Jorge Molina-Torres, Robert Winkler
Secondary metabolites of plants have important biological functions, which often depend on their localization in tissues. Ideally, a fresh untreated material should be directly analyzed to obtain a realistic view of the true sample chemistry. Therefore, there is a large interest for ambient mass-spectrometry-based imaging (MSI) methods. Our aim was to simplify this technology and to find an optimal combination of desorption/ionization principles for a fast ambient MSI of macroscopic plant samples. We coupled a 405-nm continuous-wave (CW) ultraviolet (UV) diode laser to a three-dimensionally (3D) printed low-temperature-plasma (LTP) probe...
January 14, 2019: Analytical Chemistry
Michael Urban, Stephan Hann, Helmut Rost
In this study, a two-dimensional liquid chromatography tandem mass spectrometry method was developed and validated for the determination of pesticide residues and contaminants in whole wheat grains and oats. The samples were extracted with a mixture of acetonitrile and water and were injected into the two-dimensional LC-MS/MS system without any further clean-up or sample preparation. Samples were analyzed with four different matrix matched calibrations. Matrix effects were evaluated by comparing analyte signals in the respective matrix matched standard with the neat solvent standards...
January 2, 2019: Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes
Madineh Khezerluo, Bahman Hosseini, Jafar Amiri
Hyoscyamus reticulatus L. is a herbaceous biennial belonging to the solanaceae family. Hyoscyamine and scopolamine as main tropane alkaloids accumulated in henbane are widely used in medicine to treat diseases such as parkinson's or to calm schizoid patients. Hairy roots media manipulation which uses elicitors to activate defense mechanisms is one of the main strategies for inducing secondary metabolism as well as increasing the production of valuable metabolites. Cotyledon-derived hairy root cultures were transformed by Agrobacterium rhizogenes...
December 2018: Acta Biologica Hungarica
Szymon Chowański, Joanna Pacholska-Bogalska, Grzegorz Rosiński
Synthetic insecticides are still widely used in plant protection. The main target for their action is the nervous system, in which the cholinergic system plays a vital role. Currently available insecticides have low selectivity and act on the cholinergic systems of invertebrates and vertebrates. Acetylcholine, a cholinergic system neurotransmitter, acts on cells by two types of receptors: nicotinic and muscarinic. In mammals, the role of muscarinic acetylcholine receptors (mAChRs) is quite well-known but in insects, is still not enough...
December 20, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Zhiying Guo, Hexin Tan, Zongyou Lv, Qian Ji, Yuxiang Huang, Jingjing Liu, Donghong Chen, Yong Diao, Jinping Si, Lei Zhang
Under hypoxic conditions, the expression of Vitreoscilla hemoglobin (VHb) in plants is proposed to increase the productivity of certain oxygen-requiring metabolic pathways by promoting the delivery of oxygen. Tropane alkaloids (TAs) are a class of important plant secondary metabolites with significant medicinal value; the final step in their biosynthesis requires oxygen. Whether heterologous expression of VHb, especially in different subcellular compartments, can accelerate the accumulation of TAs is not known...
December 19, 2018: Scientific Reports
Anton Lakstygal, Tatyana Kolesnikova, Sergey Khatsko, Konstantin Zabegalov, Andrey Volgin, Konstantin Demin, Vadim Shevyrin, Edina Wappler-Guzzetta, Allan Kalueff
Anticholinergic drugs based on tropane alkaloids, including atropine, scopolamine and hyoscyamine, have been used for various medicinal and toxic purposes for millennia. These drugs are competitive antagonists of acetylcholine muscarinic (M-) receptors that potently modulate the central nervous system (CNS). Currently used clinically to treat vomiting, nausea and bradycardia, as well as alongside other anesthetics to avoid vagal inhibition, these drugs also evoke potent psychotropic effects, including characteristic delirium-like states with hallucinations, altered mood and cognitive deficits...
December 19, 2018: ACS Chemical Neuroscience
Boualem Harfi, Lakhdar Khelifi, Majda Khelifi-Slaoui, Corinne Assaf-Ducrocq, Eric Gontier
Plant secondary metabolites play a major role in plant adaptation to stress. Species belonging to Solanaceae family and Datura genus produce tropane alkaloids: D. stramonium, D. tatula and D. innoxia. These species are cultivated for their hyoscyamine (HS) content, whence the interest of this study to induce transformed roots of these species with strain A4 of Agrobacterium rhizogenes. Hairy roots (HRs) of Datura were established at high frequency by infecting vitroplants. All HRs (343 independent lines) were next employed to study the production of HS and growth...
December 18, 2018: Scientific Reports
Ryad Amdoun, Lakhdar Khelifi, Majda Khelifi-Slaoui, Samia Amroune, Mark Asch, Corinne Assaf-Ducrocq, Eric Gontier
Background: The use of the desirability function approach combined with the response surface methodology (RSM), also called Desirability Optimization Methodology (DOM), has been successfully applied to solve medical, chemical, and technological questions. It is particularly efficient for the determination of the optimal conditions in natural or industrial processes involving different factors leading to the antagonist responses. Objectives: Surprisingly, DOM has never been applied to the research programs devoted to the study of plant responses to the complex environmental changes, and thus to biotechnological questions...
April 2018: Iranian Journal of Biotechnology
Matthew A Bedewitz, A Daniel Jones, John C D'Auria, Cornelius S Barry
Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive. In this study, we identify a root-expressed type III polyketide synthase from Atropa belladonna (AbPYKS) that catalyzes the formation of 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid...
December 11, 2018: Nature Communications
Fei Qiu, Chunxian Yang, Lina Yuan, Dan Xiang, Xiaozhong Lan, Min Chen, Zhihua Liao
Solanaceous medicinal plants produce tropane alkaloids (TAs). We discovered a novel gene from Atropa belladonna, AbPPAR, which encodes a phenylpyruvic acid reductase required for TA biosynthesis. AbPPAR was specifically expressed in root pericycles and endodermis. AbPPAR was shown to catalyze reduction of phenylpyruvic acid to phenyllactic acid, a precursor of TAs. Suppression of AbPPAR disrupted TA biosynthesis through reduction of phenyllactic acid levels. In summary, we identified a novel enzyme involved in TA biosynthesis...
December 4, 2018: Organic Letters
Yi Yang, Cui-Ping Zhang, Xing Liu, Yue Wei, Neng-Biao Wu
Hyoscyamine and scopolamine are important secondary metabolites of tropane alkaloid in Atropa belladonna with pharmacological values in many aspects.In this study, the seedlings of A.belladonna were planted by soil culture and treated with different concentrations of methyl jasmonate (MeJA). The contents of hyoscyamine and scopolamine,the upstream products in alkaloid synthesis,and the expression levels of key enzyme genes PMT, TR Ⅰ and H6H in secondary metabolites of A. belladonna seedlings were measured to clarify the mechanism of MeJA regulating alkaloids synthesis...
October 2018: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Jie Tang, Siwei Liang, Bing Dong, Yao Li, Shun Yao
Emulsion liquid membrane (ELM) coupled with tropine-based ionic liquid was prepared and successfully adopted for the extraction and quantitative analysis of tropane alkaloids (TA) in Radix physochlainae. Effects of formation conditions of ELM were explored and then optimized; the ideal oil-water mass ratio was determined to be 1:2.5, chloroform, Span 80 and 0.05 mol L-1 N-propyl-tropine hexafluorophosphate ([C3 Tr][PF6 ]) aqueous solution were stirred for 30 min with the speed of 1500 r min-1 . In order to extract and enrich TA with ELM efficiently, key factors related with their extraction efficiency such as stirring speed, volume of the extracts (feed solution), migration time and initial concentration of TA were systematically investigated...
November 3, 2018: Journal of Chromatography. A
Pooja Singh, Ratnum Prasad, Rashi Tewari, Meraj Jaidi, Susheel Kumar, P K Rout, Laiq Ur Rahman
Scopolamine is a pharmaceutically important tropane alkaloid which is used therapeutically in the form of an anesthetic and antispasmodic drug. The present study demonstrates enhanced scopolamine production from transgenic hairy root clones of Duboisia leichhardtii wherein the expression of quinolinate phosphoribosyl transferase (QPT) gene was silenced using the QPT-RNAi construct under the control of CaMV 35 S promoter. The RNAi hairy roots clones viz. P4, P7, P8, and P12 showed the enhanced synthesis of scopolamine with significant inhibition of nicotine biosynthesis...
September 17, 2018: Scientific Reports
Joshua M Henkin, Yulin Ren, Djaja Djendoel Soejarto, A Douglas Kinghorn
Many of the clinically used anticancer agents in Western medicine are derived from secondary metabolites found in terrestrial microbes, marine organisms, and higher plants, with additional compounds of this type being currently in clinical trials. If plants are taken specifically, it is generally agreed that the prospects of encountering enhanced small organic-molecule chemical diversity are better if tropical rather than temperate species are investigated in drug discovery efforts. Plant collection in tropical source countries requires considerable preparation and organization to conduct in a responsible manner that abides by the provisions of the 1992 Rio Convention of Biological Diversity and the 2010 Nagoya Protocol on Access to Genetic Resources...
2018: Progress in the Chemistry of Organic Natural Products
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