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Natural product chemistry

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https://www.readbyqxmd.com/read/28819353/a-metabolomics-guided-exploration-of-marine-natural-product-chemical-space
#1
Dimitrios J Floros, Paul R Jensen, Pieter C Dorrestein, Nobuhiro Koyama
INTRODUCTION: Natural products from culture collections have enormous impact in advancing discovery programs for metabolites of biotechnological importance. These discovery efforts rely on the metabolomic characterization of strain collections. OBJECTIVE: Many emerging approaches compare metabolomic profiles of such collections, but few enable the analysis and prioritization of thousands of samples from diverse organisms while delivering chemistry specific read outs...
September 2016: Metabolomics: Official Journal of the Metabolomic Society
https://www.readbyqxmd.com/read/28817221/neuroprotective-effects-of-honokiol-from-chemistry-to-medicine
#2
REVIEW
Sylwia Talarek, Joanna Listos, Davide Barreca, Ester Tellone, Antoni Sureda, Seyed Fazel Nabavi, Nady Braidy, Seyed Mohammad Nabavi
The incidence of neurological disorders is growing in developed countries together with increased lifespan. Nowadays, there are still no effective treatments for neurodegenerative pathologies, which make necessary to search for new therapeutic agents. Natural products, most of them used in traditional medicine, are considered promising alternatives for the treatment of neurodegenerative diseases. Honokiol is a natural bioactive phenylpropanoid compound, belonging to the class of neolignan, found in notable amounts in the bark of Magnolia tree, and has been reported to exert diverse pharmacological properties including neuroprotective activities...
August 17, 2017: BioFactors
https://www.readbyqxmd.com/read/28815919/graphene-oxide-as-a-carbocatalyst-for-diels-alder-reaction-in-aqueous-media
#3
Yarabhally R Girish, Subrata Pandit, Subhendu Pandit, Mrinmoy De
The [4+2] Cycloaddition reaction, known as Diels-Alder reaction, has a great importance in synthetic organic chemistry and frequently used in synthesis of natural products containing six-membered ring. Herein, we have reported an efficient protocol for Diels-Alder reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yield, wide substrate scope, low temperature, exceptional functional group tolerance, atom-economical, and water as a green solvent are the noteworthy features of this protocol...
August 16, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28814374/from-bench-laboratory-to-bed-hospital-home-how-to-explore-effective-natural-and-synthetic-pak1-blockers-longevity-promoters-for-cancer-therapy
#4
REVIEW
Hiroshi Maruta, Mok-Ryeon Ahn
PAK family kinases are RAC/CDC42-activated kinases that were first found in a soil amoeba 4 decades ago, and 2 decades later, were discovered in mammals as well. Since then at least 6 members of this family have been identified in mammals. One of them called PAK1 has been best studied so far, mainly because it is essential not only for malignant cell growth and metastasis, but also for many other diseases/disorders such as diabetes (type 2), AD (Alzheimer's disease), hypertension, and a variety of inflammatory or infectious diseases, which definitely shorten our lifespan...
August 9, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28809975/discovery-of-synthetic-small-molecules-that-enhance-the-number-of-stomata-c-h-functionalization-chemistry-for-plant-biology
#5
Asraa Ziadi, Naoyuki Uchida, Hiroe Kato, Rina Hisamatsu, Ayato Sato, Shinya Hagihara, Kenichiro Itami, Keiko U Torii
The increasing climate changes and global warming are leading to colossal agricultural problems such as abatement of food production and quality. As stomatal development is considered to play a key role in crop plant productivity and water-use efficiency, studying stomatal development is useful for understanding the productivity of plant systems for both natural and agricultural systems. Herein, we report the first-in-class synthetic small molecules enhancing the number of stomata in Arabidopsis thaliana that have been discovered by screening of the chemical library and further optimized by the Pd-catalyzed C-H arylation reaction...
August 15, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28809556/radical-chemistry-and-structural-relationships-of-ppcp-degradation-by-uv-chlorine-treatment-in-simulated-drinking-water
#6
Kaiheng Guo, Zihao Wu, Chii Shang, Bo Yao, Shaodong Hou, Xin Yang, Weihua Song, Jingyun Fang
The UV/chlorine process is an emerging advanced oxidation process (AOP) used for the degradation of micropollutants. However, the radical chemistry of this AOP is largely unknown for the degradation of numerous structurally diverse micropollutants in water matrices of varying quality. These issues were addressed by grouping 34 pharmaceuticals and personal care products (PPCPs) according to the radical chemistry of their degradation in the UV/chlorine process at practical PPCP concentrations (1 μg L-1) and in different water matrices...
August 15, 2017: Environmental Science & Technology
https://www.readbyqxmd.com/read/28803474/bioinspired-indole-prenylation-reactions-in-water
#7
Satomi Tanaka, Shinya Shiomi, Hayato Ishikawa
Isoprene units derived from dimethylallyl diphosphate (DMAPP) are an important motif in many natural products including terpenoids, carotenoids, steroids, and natural rubber. Understanding the chemical characteristics of DMAPP is an important topic in natural products chemistry, organic chemistry, and biochemistry. We have developed a direct bioinspired indole prenylation reaction using DMAPP or its equivalents as the electrophile in homogeneous aqueous acidic media in the absence of enzyme to provide prenylated indole products...
August 13, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28801573/a-structural-and-mechanistic-study-of-%C3%AF-clamp-mediated-cysteine-perfluoroarylation
#8
Peng Dai, Jonathan K Williams, Chi Zhang, Matthew Welborn, James J Shepherd, Tianyu Zhu, Troy Van Voorhis, Mei Hong, Bradley L Pentelute
Natural enzymes use local environments to tune the reactivity of amino acid side chains. In searching for small peptides with similar properties, we discovered a four-residue π-clamp motif (Phe-Cys-Pro-Phe) for regio- and chemoselective arylation of cysteine in ribosomally produced proteins. Here we report mutational, computational, and structural findings directed toward elucidating the molecular factors that drive π-clamp-mediated arylation. We show the significance of a trans conformation prolyl amide bond for the π-clamp reactivity...
August 11, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28797318/single-laboratory-validation-of-the-neogen-qualitative-lateral-flow-immunoassay-for-the-detection-of-paralytic-shellfish-toxins-in-mussels-and-oysters
#9
Alison R Turnbull, Jessica Y C Tan, Sarah C Ugalde, Gustaaf M Hallegraeff, Katrina Campbell, D Tim Harwood, Juan José Dorantes-Aranda
Detection of paralytic shellfish toxins (PSTs) in bivalve shellfish by analytical methods is complicated and costly, requiring specific expertise and equipment. Following extensive blooms of Alexandrium tamarense Group 1 in Tasmania, Australia, an investigation was made into commercially available screening test kits suitable for use with the toxin profiles found in affected bivalves. The qualitative Neogen rapid test kit, with a modified protocol to convert gonyautoxins GTX1&4 and GTX2&3 into neosaxitoxin and saxitoxin (STX), respectively, with higher cross-reactivities, was the best fit-for-purpose...
August 10, 2017: Journal of AOAC International
https://www.readbyqxmd.com/read/28794415/living-genochemetics-by-hyphenating-synthetic-biology-and-synthetic-chemistry-in-vivo
#10
Sunil V Sharma, Xiaoxue Tong, Cristina Pubill-Ulldemolins, Christopher Cartmell, Emma J A Bogosyan, Emma J Rackham, Enrico Marelli, Refaat B Hamed, Rebecca J M Goss
Marrying synthetic biology with synthetic chemistry provides a powerful approach toward natural product diversification, combining the best of both worlds: expediency and synthetic capability of biogenic pathways and chemical diversity enabled by organic synthesis. Biosynthetic pathway engineering can be employed to insert a chemically orthogonal tag into a complex natural scaffold affording the possibility of site-selective modification without employing protecting group strategies. Here we show that, by installing a sufficiently reactive handle (e...
August 9, 2017: Nature Communications
https://www.readbyqxmd.com/read/28792731/catalytic-enantioselective-carbonyl-allylation-and-propargylation-via-alcohol-mediated-hydrogen-transfer-merging-the-chemistry-of-grignard-and-sabatier
#11
Seung Wook Kim, Wandi Zhang, Michael J Krische
Merging the characteristics of transfer hydrogenation and carbonyl addition, we have developed a new class of catalytic enantioselective C-C bond formations. In these processes, hydrogen transfer between alcohols and π-unsaturated reactants generates carbonyl-organometal pairs that combine to deliver products of addition. On the basis of this mechanistic paradigm, lower alcohols are converted directly to higher alcohols in the absence of premetalated reagents or discrete alcohol-to-carbonyl redox reactions...
August 9, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28783877/macrocycles-all-aflutter-substitution-at-an-allylic-center-reveals-conformational-dynamics-of-13-macrodilactones
#12
Kelli M Rutledge, Trevor Hamlin, Donna Baldisseri, Matthias Bickelhaupt, Mark Wayne Peczuh
The shapes adopted by large-ring, macrocyclic compounds play a role in their reactivity and their ability to be bound by biomolecules. We investigate the synthesis, conformational analysis, and properties of a specific family [13]-macrodilactones as models of natural product macrocycles. The features of our macrodilactones enable us to study the relationship between stereogenic centers and planar chirality through the modular synthesis of new members of this family of macrocycles. Here we report on insights gained from a new [13]-macrodilactone that is substituted at a position adjacent to the alkene in the molecule...
August 7, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28782779/nucleophile-dependent-formation-of-6-and-7-membered-n-heterocycles-by-platinum-catalysed-cyclisation-of-1-5-bisallenes
#13
María Teresa Quirós, César Hurtado-Rodrigo, María Paz Muñoz
An unprecedented Pt-catalysed cyclisation of N-tethered 1,5-bisallenes in the presence of oxygen nucleophiles is reported, where formation of 6- or 7-membered rings is driven by the choice of nucleophile and the mechanism dictated by the nucleophile and the electronic properties of the bisallene. The reaction in the presence of alcohols gives preferentially vinyltetrahydropyridines with an extra alkoxy group and Pt-H as the active species in the catalytic cycle, while formation of di- and tetrahydroazepines with an extra hydroxyl group is favoured when water is used as nucleophile, via nucleophilic attack/carbocyclization as the favoured pathway...
August 16, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28782644/dmapt-inhibits-nf-%C3%AE%C2%BAb-activity-and-increases-sensitivity-of-prostate-cancer-cells-to-x-rays-in-vitro-and-in-tumor-xenografts-in-vivo
#14
Marc S Mendonca, William T Turchan, Melanie E Alpuche, Christopher N Watson, Neil C Estabrook, Helen Chin-Sinex, Jeremy B Shapiro, Imade E Imasuen-Williams, Gabriel Rangel, David P Gilley, Nazmul Huda, Peter A Crooks, Ronald H Shapiro
Constitutive activation of the pro-survival transcription factor NF-κB has been associated with resistance to both chemotherapy and radiation therapy in many human cancers, including prostate cancer. Our lab and others have demonstrated that the natural product parthenolide can inhibit NF-κB activity and sensitize PC-3 prostate cancers cells to X-rays in vitro; however, parthenolide has poor bioavailability in vivo and therefore has little clinical utility in this regard. We show here that treatment of PC-3 and DU145 human prostate cancer cells with dimethylaminoparthenolide (DMAPT), a parthenolide derivative with increased bioavailability, inhibits constitutive and radiation-induced NF-κB binding activity and slows prostate cancer cell growth...
August 3, 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28782567/ix-th-international-symposium-on-natural-products-chemistry-and-its-applications-ix-isnpca-termas-de-chillan-chillan-chile
#15
EDITORIAL
Carlos L Cespedes-Acuña, Julio E Alarcon-Enos
No abstract text is available yet for this article.
August 3, 2017: Food and Chemical Toxicology
https://www.readbyqxmd.com/read/28780689/can-radiation-chemistry-supply-a-highly-efficient-ao-r-p-process-for-organics-removal-from-drinking-and-waste-water-a-review
#16
Marek Trojanowicz, Anna Bojanowska-Czajka, Andrea G Capodaglio
The increasing role of chemistry in industrial production and its direct and indirect impacts in everyday life create the need for continuous search and efficiency improvement of new methods for decomposition/removal of different classes of waterborne anthropogenic pollutants. This review paper addresses a highly promising class of water treatment solutions, aimed at tackling the pressing problem of emerging contaminants in natural and drinking waters and wastewater discharges. Radiation processing, a technology originating from radiation chemistry studies, has shown encouraging results in the treatment of (mainly) organic water pollution...
August 5, 2017: Environmental Science and Pollution Research International
https://www.readbyqxmd.com/read/28777537/pushing-chemical-boundaries-with-n-heterocyclic-olefins-nhos-from-catalysis-to-main-group-element-chemistry
#17
Matthew M D Roy, Eric Rivard
N-Heterocyclic olefins (NHOs) have gone from the topic of a few scattered (but important) reports in the early 1990s to very recently being a ligand/reagent of choice in the far-reaching research fields of organocatalysis, olefin and heterocycle polymerization, and low oxidation state main group element chemistry. NHOs are formally derived by appending an alkylidene (CR2) unit onto an N-heterocyclic carbene (NHC), and their pronounced ylidic character leads to high nucleophilicity and soft Lewis basic character at the ligating carbon atom...
August 4, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28775335/nubbedb-an-updated-database-to-uncover-chemical-and-biological-information-from-brazilian-biodiversity
#18
Alan C Pilon, Marilia Valli, Alessandra C Dametto, Meri Emili F Pinto, Rafael T Freire, Ian Castro-Gamboa, Adriano D Andricopulo, Vanderlan S Bolzani
The intrinsic value of biodiversity extends beyond species diversity, genetic heritage, ecosystem variability and ecological services, such as climate regulation, water quality, nutrient cycling and the provision of reproductive habitats it is also an inexhaustible source of molecules and products beneficial to human well-being. To uncover the chemistry of Brazilian natural products, the Nuclei of Bioassays, Ecophysiology and Biosynthesis of Natural Products Database (NuBBEDB) was created as the first natural product library from Brazilian biodiversity...
August 3, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28774627/cho-cell-cytotoxicity-and-genotoxicity-analyses-of-disinfection-by-products-an-updated-review
#19
REVIEW
Elizabeth D Wagner, Michael J Plewa
The disinfection of drinking water is an important public health service that generates high quality, safe and palatable tap water. The disinfection of drinking water to reduce waterborne disease was an outstanding public health achievement of the 20th century. An unintended consequence is the reaction of disinfectants with natural organic matter, anthropogenic contaminants and bromide/iodide to form disinfection by-products (DBPs). A large number of DBPs are cytotoxic, neurotoxic, mutagenic, genotoxic, carcinogenic and teratogenic...
August 2017: Journal of Environmental Sciences (China)
https://www.readbyqxmd.com/read/28771898/olefins-from-natural-gas-via-oxychlorination-catalysis
#20
Guido Zichittella, Nicolas Aellen, Vladimir Paunović, Amol P Amrute, Javier Pérez-Ramírez
Ethylene and propylene are the key building blocks of the chemical industry, but current processes are unable to close the growing gap between demand and manufacture. Herein, we report an exceptional europium oxychloride (EuOCl) catalyst for the selective (≥95%) production of light olefins from ethane and propane via oxychlorination chemistry, achieving yields of ethylene (90%) and propylene (40%) unparalleled by any existing olefin production technology. The outstanding performance was rationalized by its bifunctional character, integrating the alkane oxychlorination into alkyl chloride and its dehydrochlorination into the olefin, thus recycling the halogen source...
August 3, 2017: Angewandte Chemie
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