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tropane alkaloids

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
Harald John, Michael Rychlik, Horst Thiermann, Christian Schmidt
RATIONALE: Atropine (Atr) and scopolamine (Scp) are toxic secondary plant metabolites of species within the Solanaceae genus that can accidentally or intentionally reach the food store chain by inaccurate harvesting of any plant material, e.g. for herbal tea infusions. Ingestion may cause severe anticholinergic poisoning thus requiring risk-oriented determination in food and beverages. The suitability of matrix-assisted laser desorption/ionization time-of-flight (tandem) mass spectrometry, MALDI-TOF MS(/MS), should be characterized for simultaneous analysis...
November 30, 2018: Rapid Communications in Mass Spectrometry: RCM
Gabrielle Macedo Pereira, Letícia Gondim Lambert Moreira, Themístocles da Silva Negreiros Neto, Wamberto Alristenio Moreira de Almeida, Jailma Almeida-Lima, Hugo Alexandre Oliveira Rocha, Euzébio Guimarães Barbosa, José Angelo S Zuanazzi, Mauro Vieira de Almeida, Richard Michael Grazul, Armando Navarro-Vázquez, Fernando Hallwass, Leandro de Santis Ferreira, Matheus de Freitas Fernandes-Pedrosa, Raquel Brandt Giordani
Stem bark, root bark, and leaf extracts of Erythroxylum pungens were subjected to phytochemical analysis. N,N-dimethyltryptamine (DMT) was isolated and characterized from E. pungens roots. This unprecedented result is remarkable since no indole alkaloid has been previously reported from Erythroxylaceae so far. Eleven known tropane alkaloids were identified by their mass spectra and 3-(2-methylbutyryloxy)tropan-6,7-diol as well as 3-(2-methylbutyryloxy)nortropan-6,7-diol were isolated and characterized based on mass spectrometry, 1 H, 13 C, COSY, and NOESY NMR analysis...
November 2018: Phytochemistry
Eszter Borbála Both, David Moreno-González, Juan F García-Reyes, Mihály Dernovics
The spread of Datura sp. in European countries influences crop management and implies continuous food safety issues because of tropane alkaloids, atropine and scopolamine, the most relevant natural toxic compounds of this weed. These alkaloids can contaminate cereals to such a level that hampers food/feed related use and diverts batches of contaminated raw materials towards ultimate disposal such as burning. As no unambiguous information has been available on the fate of tropane alkaloids in soils, our study focused on the quantification and follow-up of these toxic residues in a soil experiment where the tropane alkaloids were mixed to the soil in the form of naturally contaminated unhulled millet in 1:40 millet:soil ratio - this approach provides a more realistic scenario compared to standard solution based spiking...
June 1, 2018: Science of the Total Environment
Ophélie Fliniaux, Albrecht Roscher, Dominique Cailleu, François Mesnard
Cell suspensions initiated from Duboisia myoporoides -a shrub belonging to the Solanaceae family and being a rich source of tropane alkaloids-previously showed their ability to glycosylate scopoletin into scopolin, which represent coumarins showing health benefits. To investigate the time course of this glycosylation reaction, an in vivo NMR approach was developed using a perfusion system in an 8-mm NMR tube and 1 H NMR with 1D and 2D (TOCSY and NOESY) experiments. The time course of metabolic changes could therefore be followed without any labeling...
August 2018: Planta Medica
Ana Romera-Torres, Roberto Romero-González, José Luis Martínez Vidal, Antonia Garrido Frenich
In the last years, the interest in secondary metabolites from plants has been growing, and even more if they have or would have medical applications, as it happens with tropane alkaloids and calystegines. Therefore, the number of analytical methods for the analysis of these compounds has been increasing. In this review, the extraction methods as well as the chromatographic separation and detection techniques based on mass spectrometry to determine tropane alkaloids and calystegines in plant raw material and food have been described...
August 24, 2018: Journal of Chromatography. A
Jesús Marín-Sáez, Roberto Romero-González, Antonia Garrido Frenich, Francisco Javier Egea-González
Homeopathic products are still a controversial issue in modern medicine, understood as complementary or alternative medicine (CAM). In this particular case, homeopathic products prepared from Atropa belladonna extracts may present specific problems due to the effects derived from its components. This article applies a simple, rapid, reliable method to the analysis of different homeopathic products obtained from Atropa belladonna; drugs containing high concentration of plant extracts; and Atropa belladonna seeds...
October 2018: Drug Testing and Analysis
Shuang Guo, Yi Yang, Xing Liu, Neng-Biao Wu
In order to study the mechanism of nitrogen metabolism and secondary metabolism in Atropa belladonna hairy roots treated with yeast extract, yeast extract(YE) was added to the culture medium. Then the changes of physiological and biochemical indexes of A. belladonna hairy roots after treatment with YE were detected. The results are as follows,the activity of key enzymes of nitrogen metabolism changed differently. Compared with the control group (CK), the activity of nitrate reductase (NR) and glutamine synthetase (GS) were significantly increased, while the activity of glutamate dehydrogenase (GDH) was not changed significantly...
April 2018: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
F Driehuis, J M Wilkinson, Y Jiang, I Ogunade, A T Adesogan
Silage may contain several agents that are potentially hazardous to animal health, the safety of milk or other animal food products, or both. This paper reviews published literature about microbial hazards, plant toxins, and chemical hazards. Microbial hazards include Clostridium botulinum, Bacillus cereus, Listeria monocytogenes, Shiga toxin-producing Escherichia coli, Mycobacterium bovis, and various mold species. High concentrations of C. botulinum in silage have been associated with cattle botulism. A high initial concentration of C...
May 2018: Journal of Dairy Science
Gunnar F Kwakye, Jennifer Jiménez, Jessica A Jiménez, Michael Aschner
Atropa belladonna, commonly known as belladonna or deadly nightshade, ranks among one of the most poisonous plants in Europe and other parts of the world. The plant contains tropane alkaloids including atropine, scopolamine, and hyoscyamine, which are used as anticholinergics in Food and Drug Administration (FDA) approved drugs and homeopathic remedies. These alkaloids can be very toxic at high dose. The FDA has recently reported that Hyland's baby teething tablets contain inconsistent amounts of Atropa belladonna that may have adverse effects on the nervous system and cause death in children, thus recalled the product in 2017...
June 2018: Food and Chemical Toxicology
Tianxiang Lei, Huan Wang, Songling Li, Jianwei Shen, Shilong Chen, Xiaojian Cai, Dangwei Zhou
To achieve a high yield of tropane alkaloids (TA) and exploit the alpine plant sustainably, an optimized protocol for induction and establishment of hairy roots culture of Prezwalskia tangutica Maxim was developed through selection of appropriate Agrobacterium strain and the explant type. The hypocotyl is more readily facile to induce the HR than the cotyledon is when infected with the three different agrobacterium strains. MUS440 has an efficiency (of up to 20%), whereas the ATCC10060 (A4) can induce HR on both types of explants with the highest frequency (33...
March 2018: 3 Biotech
Chen Geng, Tengfei Zhao, Chunxian Yang, Qiaozhuo Zhang, Feng Bai, Junlan Zeng, Fangyuan Zhang, Xiaoqiang Liu, Xiaozhong Lan, Min Chen, Zhihua Liao
N-methylputrescine is the precursor of nicotine and pharmaceutical tropane alkaloids such as hyoscyamine. Putrescine N-methyltransferase (PMT) catalyzes the N-methylation of putrescine to form N-methylputrescine. While the role of PMT in nicotine biosynthesis is clear, knowledge of PMT in the biosynthesis of tropane alkaloids (TAs) and the regulation of polyamines remains limited. We characterized a PMT gene from Hyoscyamus niger, designated HnPMT that was specifically expressed in roots, especially in the secondary roots and dramatically induced by methyl jasmonate (MeJA)...
June 2018: Plant Physiology and Biochemistry: PPB
J K Wilson, A S Tseng, K A Potter, G Davidowitz, J G Hildebrand
Plants have evolved many defenses against insect herbivores, including numerous chemicals that can reduce herbivore growth, performance, and fitness. One group of chemicals, the tropane alkaloids, is commonly found in the nightshade family (Solanaceae) and has been thought to reduce performance and fitness in insects. We examined the effects of the tropane alkaloid scopolamine, the alkaloid constituent of Datura wrightii , which is the most frequent host plant for the abundant and widespread insect herbivore Manduca sexta in the southwestern United States...
February 2018: Arthropod-plant Interactions
Zahra Shakeran, Mehrnaz Keyhanfar, Mustafa Ghanadian
The (-)-hyoscyamine, atropine and scopolamine (hyoscine) are three valuable tropane alkaloids while scopolamine is the most important member of this group for the pharmaceutical industry due to its higher demand compared to hyoscyamine and atropine. Scopolamine is an anticholinergic reagent with several therapeutic applications. In the current study, the hairy roots culture of Datura metel was used as an advantageous method for production of scopolamine. The hairy roots are formed by Agrobacterium rhizogenes and have genetic stability, high growth rate and lateral branching...
December 2017: Molecular Biology Research Communications
Xiaozhong Lan, Junlan Zeng, Ke Liu, Fangyuan Zhang, Ge Bai, Min Chen, Zhihua Liao, Luqi Huang
Scopolia lurida, a medicinal plant native to the Tibetan Plateau, is among the most effective producers of pharmaceutical tropane alkaloids (TAs). The hyoscyamine 6β-hydroxylase genes of Hyoscyamus niger (HnH6H) and S. lurida (SlH6H) were cloned and respectively overexpressed in hairy root cultures of S. lurida, to compare their effects on promoting the production of TAs, especially the high-value scopolamine. Root cultures with SlH6H/HnH6H overexpression were confirmed by PCR and real-time quantitative PCR, suggesting that the enzymatic steps defined by H6H were strongly elevated at the transcriptional level...
February 26, 2018: Biochemical and Biophysical Research Communications
Camila Sanz, Enzo Tagliazucchi
Ever since the modern rediscovery of psychedelic substances by Western society, several authors have independently proposed that their effects bear a high resemblance to the dreams and dreamlike experiences occurring naturally during the sleep-wake cycle. Recent studies in humans have provided neurophysiological evidence supporting this hypothesis. However, a rigorous comparative analysis of the phenomenology ("what it feels like" to experience these states) is currently lacking. We investigated the semantic similarity between a large number of subjective reports of psychoactive substances and reports of high/low lucidity dreams, and found that the highest-ranking substance in terms of the similarity to high lucidity dreams was the serotonergic psychedelic lysergic acid diethylamide (LSD), whereas the highest-ranking in terms of the similarity to dreams of low lucidity were plants of the Datura genus, rich in deliriant tropane alkaloids...
2018: Frontiers in Neuroscience
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