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Natural product chemistry

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https://www.readbyqxmd.com/read/28230296/plants-to-polyelectrolytes-theophylline-polymers-and-their-microsphere-synthesis
#1
Ryan Guterman, Markus Antonietti, Jiayin Yuan
To extend fossil oil supplies, sustainable feed stocks for the production of useful reagents and polymers should be harnessed. In this regard, chemicals derived from plants are excellent candidates. While the vast majority of plant sources used for polymer science only contain C x H y O z , alkaloids such as caffeine, nicotine, and theophylline possess nitrogen functionality that can provide new functions for bioderived polymers and their synthesis. In this context, the chemistry of theophylline, a natural product found in chocolate and tea, is exploited to create a cationic "poly(theophylline)" in a straightforward fashion for the first time...
February 23, 2017: Macromolecular Rapid Communications
https://www.readbyqxmd.com/read/28228228/molecular-hybridization-conceded-exceptionally-potent-quinolinyl-oxadiazole-hybrids-through-phenyl-linked-thiosemicarbazide-antileishmanial-scaffolds-in-silico-validation-and-sar-studies
#2
Muhammad Taha, Nor Hadiani Ismail, Muhammad Ali, Umer Rashid, Syarul Imran, Nizam Uddin, Khalid Mohammed Khan
The high potential of quinoline containing natural products and their derivatives in medicinal chemistry led us to discover a novel series of compounds 6-23 based on the concept of molecular hybridization. Most of the synthesized analogues exhibited potent leishmanicidal potential. The most potent compound (23, IC50=0.10±0.001μM) among the series was found ∼70 times more lethal than the standard drug. The current series 6-23 conceded in the development of fourteen (14) extraordinarily active compounds against leishmaniasis...
February 19, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/28225616/a-straightforward-approach-for-3d-bacterial-printing
#3
Benjamin A E Lehner, Dominik T Schmieden, Anne Sara Meyer
Sustainable and personally tailored materials production is an emerging challenge to society. Living organisms can produce and pattern an extraordinarily wide range of different molecules in a sustainable way. These natural systems offer an abundant source of inspiration for the development of new environmentally-friendly materials production techniques. In this paper, we describe the first steps towards the 3-dimensional printing of bacterial cultures for materials production and patterning. This methodology combines the capability of bacteria to form new materials with the reproducibility and tailored approach of 3D printing systems...
February 22, 2017: ACS Synthetic Biology
https://www.readbyqxmd.com/read/28221353/from-helical-to-planar-chirality-by-on-surface-chemistry
#4
Oleksandr Stetsovych, Martin Švec, Jaroslav Vacek, Jana Vacek Chocholoušová, Andrej Jančařík, Jiří Rybáček, Krzysztof Kosmider, Irena G Stará, Pavel Jelínek, Ivo Starý
The chirality of molecular structures is paramount in many phenomena, including enantioselective reactions, molecular self-assembly, biological processes and light or electron-spin polarization. Flat prochiral molecules, which are achiral in the gas phase or solution, can exhibit adsorption-induced chirality when deposited on surfaces. The whole array of such molecular adsorbates is naturally racemic as spontaneous global mirror-symmetry breaking is disfavoured. Here we demonstrate a chemical method of obtaining flat prochiral molecules adsorbed on the solid achiral surface in such a way that a specific adsorbate handedness globally dominates...
March 2017: Nature Chemistry
https://www.readbyqxmd.com/read/28218831/new-possibilities-for-magnetic-control-of-chemical-and-biochemical-reactions
#5
Anatoly Buchachenko, Ronald G Lawler
Chemistry is controlled by Coulomb energy; magnetic energy is lower by many orders of magnitude and may be confidently ignored in the energy balance of chemical reactions. The situation becomes less clear, however, when reaction rates are considered. In this case, magnetic perturbations of nearly degenerate energy surface crossings may produce observable, and sometimes even dramatic, effects on reactions rates, product yields, and spectroscopic transitions. A case in point that has been studied for nearly five decades is electron spin-selective chemistry via the intermediacy of radical pairs...
February 20, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28217773/finding-food-how-marine-invertebrates-use-chemical-cues-to-track-and-select-food
#6
REVIEW
Michiya Kamio, Charles D Derby
Benthic marine invertebrates sense molecules from other organisms and use these molecules to find and evaluate the organisms as sources of food. These processes depend on the detection and discrimination of molecules carried in sea water around and in the mouths of these animals. To understand these processes, researchers have studied how molecules released from food distribute in the sea water as a plume, how animals respond to the plume, the molecular identity of the attractants in the plume, the effect of turbulence on food-searching success, and how animals evaluate the quality of food and make decisions to eat or not...
February 20, 2017: Natural Product Reports
https://www.readbyqxmd.com/read/28199101/fungal-identification-using-molecular-tools-a-primer-for-the-natural-products-research-community
#7
Huzefa A Raja, Andrew N Miller, Cedric J Pearce, Nicholas H Oberlies
Fungi are morphologically, ecologically, metabolically, and phylogenetically diverse. They are known to produce numerous bioactive molecules, which makes them very useful for natural products researchers in their pursuit of discovering new chemical diversity with agricultural, industrial, and pharmaceutical applications. Despite their importance in natural products chemistry, identification of fungi remains a daunting task for chemists, especially those who do not work with a trained mycologist. The purpose of this review is to update natural products researchers about the tools available for molecular identification of fungi...
February 15, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28198919/natural-compounds-from-mexican-medicinal-plants-as-potential-drug-leads-for-anti-tuberculosis-drugs
#8
Rocio Gómez-Cansino, Silvia Laura Guzmán-Gutiérrez, María Guadalupe Campos-Lara, Clara Ines Espitia-Pinzón, Ricardo Reyes-Chilpa
In Mexican Traditional Medicine 187 plant species are used in the treatment of respiratory conditions that may be associated with tuberculosis. In this contribution, we review the ethnobotany, chemistry and pharmacology of 63 species whose extracts have been assayed for antimycobacterial activity in vitro. Among these, the most potent is Aristolochia brevipes (MIC= 12.5 µg/mL), followed by Aristolochia taliscana, Citrus sinensis, Chrysactinia mexicana, Persea americana, and Olea europaea (MIC<64 µg/mL)...
February 9, 2017: Anais da Academia Brasileira de Ciências
https://www.readbyqxmd.com/read/28198609/an-unusual-flavin-dependent-halogenase-from-the-metagenome-of-the-marine-sponge-theonella-swinhoei-wa
#9
Duncan R M Smith, Agustinus R Robert Uria, Eric J N Helfrich, Daniela Milbredt, Karl-Heinz van-Pee, Joern Piel, Rebecca J M Goss
Uncultured bacteria from sponges have been demonstrated to be responsible for the generation of many potent, bioactive natural products including halogenated metabolites.1 The identification of gene clusters from the metagenomes of such bacterial communities enables the discovery of enzymes that mediate new and useful chemistries and allows insight to be gained into the biogenesis of potentially pharmacologically important natural products. Here we report a new pathway to the keramamides (krm); the first functional evidence for the existence of a distinct producer in the Theonella swinhoei WA chemotype is revealed, and a key enzyme on the pathway, a unique flavin dependent halogenase with a broad substrate specificity, and with potential as a useful new biocatalytic tool is described...
February 15, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28194563/a-critical-evaluation-of-the-quality-of-published-13-c-nmr-data-in-natural-product-chemistry
#10
Wolfgang Robien
Nuclear Magnetic Resonance spectroscopy contributes very efficiently to the structure elucidation process in organic chemistry. Carbon-13 NMR spectroscopy allows direct insight into the skeleton of organic compounds and therefore plays a central role in the structural assignment of natural products. Despite this important contribution, there is no established and well-accepted workflow protocol utilized during the first steps of interpreting spectroscopic data and converting them into structural fragments and then combining them, by considering the given spectroscopic constraints, into a final proposal of structure...
2017: Progress in the Chemistry of Organic Natural Products
https://www.readbyqxmd.com/read/28191843/production-of-stealthin-c-involves-an-s-n-type-smiles-rearrangement
#11
Peng Wang, Gloria J Hong, Matthew R Wilson, Emily P Balskus
The kinamycin family of aromatic polyketide natural products contains an atypical angucycline ring system substituted with a diazo group. The enzymatic chemistry involved in constructing both of these structural features has been largely unexplored. Here we report the in vivo and in vitro production of seongomycin, a shunt product from this pathway, and stealthin C, a proposed biosynthetic precursor to the kinamycins. We show that a single enzyme, the flavin-dependent monooxygenase AlpJ, can generate these metabolites from N-acetyl-l-cysteine and l-cysteine, respectively, and that the synthesis of stealthin C likely proceeds via a nonenzymatic S-N-type Smiles rearrangement...
February 16, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28182436/kinetics-chemistry-and-morphology-of-syngas-photoinitiated-chemical-vapor-deposition
#12
Donya Farhanian, Gregory De Crescenzo, Jason R Tavares
Syngas is the product of gasification processes and is used for the production of petrochemicals. Little attention has been paid to its use in the production of oligomeric thin films under ambient conditions. Herein, the nature of the photoinitiated chemical vapor deposition of films made from syngas using high-wavelength ultraviolet light is discussed, including an exploration of the oligomeric films' structure, synthesis mechanism, and growth kinetics. Specifically, X-ray photoelectron spectroscopy and time-of-flight secondary ion mass spectrometry analyses provide insight into the chemical structure, illustrating the effect of photogenerated radicals in the formation of aliphatic, anhydride, and cyclic structures...
February 17, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/28181828/synthesis-of-sericin-based-conjugates-by-click-chemistry-enhancement-of-sunitinib-bioavailability-and-cell-membrane-permeation
#13
Luca Scrivano, Domenico Iacopetta, Maria Stefania Sinicropi, Carmela Saturnino, Pasquale Longo, Ortensia Ilaria Parisi, Francesco Puoci
Sericin is a natural protein that has been used in biomedical and pharmaceutical fields as raw material for polypeptide-based drug delivery systems (DDSs). In this paper, it has been employed as pharmaceutical biopolymer for the production of sunitinib-polypeptide conjugate. The synthesis has been carried out by simple click reaction in water, using the redox couple l-ascorbic acid/hydrogen peroxide as a free radical grafting initiator. The bioconjugate molecular weight (50 kDa < Mw < 75 kDa) was obtained by SDS-PAGE, while the spectroscopic characteristics have been studied in order to reveal the presence of grafted sunitinib...
November 2017: Drug Delivery
https://www.readbyqxmd.com/read/28181080/madurastatin-b3-a-rare-aziridine-derivative-from-actinomycete-nocardiopsis-sp-ls150010-with-potent-anti-tuberculosis-activity
#14
Xinjun Zhang, Hongtao He, Rong Ma, Zengchun Ji, Qi Wei, Huanqin Dai, Lixin Zhang, Fuhang Song
Since the discovery of the first antibiotic, natural products have played an important role in chemistry, biology and medicine. To explore the potential of bioactive compounds from microbes isolated from the southeast of Tibet, China, a crude extract library was constructed and screened against Staphylococcus aureus. The strain Nocardiopsis sp. LS150010 was scaled up and subjected to further chemical studies, resulting in the identification of N-salicyloyl-2-aminopropan-1,3-diol (2) and its rare aziridine derivative, madurastatin B3 (1)...
February 8, 2017: Journal of Industrial Microbiology & Biotechnology
https://www.readbyqxmd.com/read/28178813/effect-of-the-nature-of-the-substrate-on-the-surface-chemistry-of-atomic-layer-deposition-precursors
#15
Yunxi Yao, Jason P Coyle, Seán T Barry, Francisco Zaera
The thermal chemistry of Cu(I)-sec-butyl-2-iminopyrrolidinate, a promising copper amidinate complex for atomic layer deposition (ALD) applications, was explored comparatively on several surfaces by using a combination of surface-sensitive techniques, specifically temperature-programmed desorption and x-ray photoelectron spectroscopy (XPS). The substrates explored include single crystals of transition metals (Ni(110) and Cu(110)), thin oxide films (NiO/Ni(110) and SiO2/Ta), and oxygen-treated metals (O/Cu(110))...
February 7, 2017: Journal of Chemical Physics
https://www.readbyqxmd.com/read/28171830/a-review-on-antioxidant-potential-of-bioactive-heterocycle-benzofuran-natural-and-synthetic-derivatives
#16
REVIEW
Karam Chand, Rajeshwari, Asha Hiremathad, Mahak Singh, M Amelia Santos, Rangappa S Keri
The majority of heterocycle compounds and typically common heterocycle fragments present in most pharmaceuticals currently marketed, alongside with their intrinsic versatility and unique physicochemical properties, have poised them as true cornerstones of medicinal chemistry. In this context, oxygen heterocycles exhibit diverse biological and pharmacological activities due in part to the similarities with many natural and synthetic molecules with known biological activity. Among oxygen containing heterocycles, benzofuran (synthetic and natural isolated) and its derivatives have attracted medicinal chemists and pharmacologists due to their pronounced biological activities and their potential applications as pharmacological agents such as antioxidant, antitumor, antiplatelet, antimalarial, antiinflammatory, antidepressant and anticonvulsant properties...
November 18, 2016: Pharmacological Reports: PR
https://www.readbyqxmd.com/read/28170012/understanding-fts-selectivity-the-crucial-role-of-surface-hydrogen
#17
C J Weststrate, J W Niemantsverdriet
Monomeric forms of carbon play a central role in the synthesis of long chain hydrocarbons via the Fischer-Tropsch synthesis (FTS). We explored the chemistry of C1Hxad species on the close-packed surface of cobalt. Our findings on this simple model catalyst highlight the important role of surface hydrogen and vacant sites for product selectivity. We furthermore find that COad affects hydrogen in multiple ways. It limits the adsorption capacity for Had, lowers its adsorption energy and inhibits dissociative H2 adsorption...
February 7, 2017: Faraday Discussions
https://www.readbyqxmd.com/read/28166535/onset-of-the-aerobic-nitrogen-cycle-during-the-great-oxidation-event
#18
Aubrey L Zerkle, Simon W Poulton, Robert J Newton, Colin Mettam, Mark W Claire, Andrey Bekker, Christopher K Junium
The rise of oxygen on the early Earth (about 2.4 billion years ago) caused a reorganization of marine nutrient cycles, including that of nitrogen, which is important for controlling global primary productivity. However, current geochemical records lack the temporal resolution to address the nature and timing of the biogeochemical response to oxygenation directly. Here we couple records of ocean redox chemistry with nitrogen isotope ((15)N/(14)N) values from approximately 2.31-billion-year-old shales of the Rooihoogte and Timeball Hill formations in South Africa, deposited during the early stages of the first rise in atmospheric oxygen on the Earth (the Great Oxidation Event)...
February 6, 2017: Nature
https://www.readbyqxmd.com/read/28160211/natural-product-molecular-fossils
#19
Heinz Falk, Klaus Wolkenstein
The natural products synthesized by organisms that were living a long time ago gave rise to their molecular fossils. These can consist of either the original unchanged compounds or they may undergo peripheral transformations in which their skeletons remain intact. In cases when molecular fossils can be traced to their organismic source, they are termed "geological biomarkers".This contribution describes apolar and polar molecular fossils and, in particular biomarkers, along the lines usually followed in organic chemistry textbooks, and points to their bioprecursors when available...
2017: Progress in the Chemistry of Organic Natural Products
https://www.readbyqxmd.com/read/28154844/de-orphaning-the-marine-natural-product-%C3%A2-marinopyrrole-a-by-computational-target-prediction-and-biochemical-validation
#20
P Schneider, G Schneider
Exploring the full potential of bioactive natural products and phenotypic screening hits for drug discovery and design requires profound understanding of the macromolecular targets involved. We present a computational method for target prediction, and showcase its practical applicability, taking the marine anticancer compound (±)-marinopyrrole A as an example. With an overall accuracy of 67%, the ligand-based method employed identified the natural product as a potent glucocorticoid, cholecystokinin, and orexin receptor antagonist...
February 3, 2017: Chemical Communications: Chem Comm
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