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indole hydroxylation

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https://www.readbyqxmd.com/read/27919656/biotransformation-of-isofraxetin-6-o-%C3%AE-d-glucopyranoside-by-angelica-sinensis-oliv-diels-callus
#1
Di Zhou, Yuhua Zhang, Zhe Jiang, Yue Hou, Kun Jiao, Chunyan Yan, Ning Li
Isofraxetin-6-O-β-d-glucopyranoside, identified from traditional medicinal herbal Xanthoceras sorbifolia Bunge, has been demonstrated to be a natural neuroinflammatory inhibitor. In order to obtain more derivatives with potential anti-neuroinflammatory effects, biotransformation was carried out. According to the characteristics of coumarin skeleton, suspension cultures of Angelica sinensis (Oliv.) Diels callus (A. sinensis callus) were employed because of the presence of diverse phenylpropanoids biosynthetic enzymes...
November 24, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27810943/methyl-transfer-in-glucosinolate-biosynthesis-mediated-by-indole-glucosinolate-o-methyltransferase-5
#2
Marina Pfalz, Maisara Mukhaimar, François Perreau, Jayne Kirk, Cecilie Ida Cetti Hansen, Carl Erik Olsen, Niels Agerbirk, Juergen Kroymann
Indole glucosinolates (IGs) are plant secondary metabolites that are derived from the amino acid tryptophan. The product of Arabidopsis (Arabidopsis thaliana) IG core biosynthesis, indol-3-ylmethyl glucosinolate (I3M), can be modified by hydroxylation and subsequent methoxylation of the indole ring in position 1 (1-IG modification) or 4 (4-IG modification). Products of the 4-IG modification pathway mediate plant-enemy interactions and are particularly important for Arabidopsis innate immunity. While CYP81Fs encoding cytochrome P450 monooxygenases and IGMTs encoding indole glucosinolate O-methyltransferases have been identified as key genes for IG modification, our knowledge about the IG modification pathways is not complete...
December 2016: Plant Physiology
https://www.readbyqxmd.com/read/27810600/chemical-exploration-of-4-4-fluorobenzyl-piperidine-fragment-for-the-development-of-new-tyrosinase-inhibitors
#3
Stefania Ferro, Laura De Luca, Maria Paola Germanò, Maria Rosa Buemi, Laura Ielo, Giovanna Certo, Margarita Kanteev, Ayelet Fishman, Antonio Rapisarda, Rosaria Gitto
Tyrosinase is involved in the production of melanin through the hydroxylation of monophenols to o-diphenols. The role of this enzyme was extensively studied in order to identify new therapeutics preventing skin pigmentation and melanoma. In this work we initially identified the 3-(4-benzylpiperidin-1-yl)-1-(1H-indol-3-yl)propan-1-one (1a) as promising mushroom tyrosinase inhibitor (IC50 = 252 μM). Then, several chemical modifications were performed and new analogues related to compound 1a were synthesized...
October 18, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27776479/enhanced-metabolic-process-to-indole-alkaloids-in-clematis-terniflora-dc-after-exposure-to-high-level-of-uv-b-irradiation-followed-by-the-dark
#4
Cuixia Gao, Bingxian Yang, Dandan Zhang, Meng Chen, Jingkui Tian
BACKGROUND: Indole alkaloids, which characteristically contain an indole nucleus, have pharmaceutical potential in a diverse range of applications. UV-B can elicit the accumulation of indole alkaloids. The indole alkaloid (6-hydroxyl-1H-indol-3-yl) carboxylic acid methyl ester with cytotoxic activity was found to accumulate in Clematis terniflora DC. leaves after exposure to high level of UV-B irradiation and the dark. However, a more in-depth analysis of the process behind this response has not yet been performed...
October 24, 2016: BMC Plant Biology
https://www.readbyqxmd.com/read/27766872/pharmacokinetics-and-metabolism-of-selective-oxoeicosanoid-oxe-receptor-antagonists-and-their-effects-on-5-oxo-6-8-11-14-eicosatetraenoic-acid-5-oxo-ete-induced-granulocyte-activation-in-monkeys
#5
Chantal Cossette, Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Vivek Gore, Sylvie Gravel, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell
The potent eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that acts via the selective OXE receptor, which is present in many species, but not rodents. We previously reported that the indole 230 is a potent human OXE receptor antagonist. The objective of the present study was to determine whether the monkey would be a suitable animal model to investigate its pharmaceutical potential. We found that monkey leukocytes synthesize and respond to 5-oxo-ETE, and that 230 is a potent antagonist of the OXE receptor in monkey eosinophils...
October 21, 2016: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27743600/glucosinolate-diversity-within-a-phylogenetic-framework-of-the-tribe%C3%A2-cardamineae-brassicaceae-unraveled-with-hplc-ms-ms-and%C3%A2-nmr-based-analytical-distinction-of-70-desulfoglucosinolates
#6
Carl Erik Olsen, Xiao-Chen Huang, Cecilie I C Hansen, Don Cipollini, Marian Ørgaard, Annemarie Matthes, Fernando Geu-Flores, Marcus A Koch, Niels Agerbirk
As a basis for future investigations of evolutionary trajectories and biosynthetic mechanisms underlying variations in glucosinolate structures, we screened members of the crucifer tribe Cardamineae by HPLC-MS/MS, isolated and identified glucosinolates by NMR, searched the literature for previous data for the tribe, and collected HPLC-MS/MS data for nearly all glucosinolates known from the tribe as well as some related structures (70 in total). This is a considerable proportion of the approximately 142 currently documented natural glucosinolates...
October 13, 2016: Phytochemistry
https://www.readbyqxmd.com/read/27632559/biosynthesis-of-shearinine-diversification-of-a-tandem-prenyl-moiety-of-fungal-indole-diterpenes
#7
Chengwei Liu, Atsushi Minami, Tohru Dairi, Katsuya Gomi, Barry Scott, Hideaki Oikawa
The late-stage biosynthetic pathway of the indole diterpene shearinine involving four enzymatic reactions (JanQDOJ) was elucidated by an efficient heterologous expression system using Aspergillus oryzae. Key oxidative cyclization, forming a characteristic A/B bicyclic shearinine core by flavoprotein oxidase, was studied using a substrate analogue and a buffer containing H2(18)O. These experimental data provided evidence that JanO catalyzes two-step oxidation via a hydroxylated product and that the JanO reaction involves the hydride-transfer mechanism...
October 7, 2016: Organic Letters
https://www.readbyqxmd.com/read/27619234/metabolism-of-melatonin-in-the-skin-why-is-it-important
#8
Andrzej T Slominski, Igor Semak, Tobias W Fischer, Tae-Kang Kim, Konrad Kleszczyński, Ruediger Hardeland, Russel J Reiter
Melatonin is produced in almost all living taxa and is probaly 2-3 billion years old. Its pleiotropic activities are related to its local concentration that is secondary to its local synthesis, delivery from distant sites and metabolic or non-enzymatic consumption. This consumption generates metabolites through indolic, kynuric and cytochrome P450 (CYP) mediated hydroxylations and O-demethylation or non-enzymatic processes, with potentially diverse phenotypic effects. While melatonin acts through receptor dependent and independent mechanism, receptors for melatonin metabolites remain to be identified, while their receptor independent activities are well documented...
September 13, 2016: Experimental Dermatology
https://www.readbyqxmd.com/read/27504870/phase-i-metabolism-of-the-highly-potent-synthetic-cannabinoid-mdmb-chmica-and-detection-in-human-urine-samples
#9
Florian Franz, Verena Angerer, Bjoern Moosmann, Volker Auwärter
Among the recently emerged synthetic cannabinoids, MDMB-CHMICA (methyl N-{[1-(cyclohexylmethyl)-1H-indol-3-yl]carbonyl}-3-methylvalinate) shows an extraordinarily high prevalence in intoxication cases, necessitating analytical methods capable of detecting drug uptake. In this study the in vivo phase I metabolism of MDMB-CHMICA was investigated using LC-ESI-MS/MS and LC-ESI-Q-ToF-MS techniques. The main metabolites are formed by hydrolysis of the methyl ester and oxidation of the cyclohexyl methyl side chain...
August 9, 2016: Drug Testing and Analysis
https://www.readbyqxmd.com/read/27477667/concise-synthesis-of-2r-4r-monatin
#10
Yusuke Amino
Monatin, 4-hydroxy-4-(3-indolylmethyl)-glutamic acid, is a naturally occurring sweet amino acid. The (2R,4R)-monatin isomer has been found to be the sweetest among its four stereoisomers. A concise and efficient synthesis of (2R,4R)-monatin was accomplished by the alkylation of (4R)-N-tert-butoxycarbonyl (tBoc)-4-tert-butyldimethylsilyoxy-D-pyroglutamic acid methyl ester with tert-butyl 3-(bromomethyl)-1H-indole-1-carboxylate to give (4R)-N-tBoc-4-tert-butyldimethylsilyloxy-4-(N-tBoc-3-indolylmethyl)-D-pyroglutamic acid methyl ester, i...
2016: Chemical & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/27328899/metabolic-patterns-of-jwh-210-rcs-4-and-thc-in-pig-urine-elucidated-using-lc-hr-ms-ms-do-they-reflect-patterns-in-humans
#11
Nadine Schaefer, Andreas G Helfer, Mattias Kettner, Matthias W Laschke, Julia Schlote, Andreas H Ewald, Markus R Meyer, Michael D Menger, Hans H Maurer, Peter H Schmidt
The knowledge of pharmacokinetic (PK) properties of synthetic cannabinoids (SCs) is important for interpretation of analytical results found for example in intoxicated individuals. In the absence of human data from controlled studies, animal models elucidating SC PK have to be established. Pigs providing large biofluid sample volumes were tested for prediction of human PK data. In this context, the metabolic fate of two model SCs, namely 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-210) and 2-(4-methoxyphenyl)-1-(1-pentyl-indol-3-yl)methanone (RCS-4), was elucidated in addition to Δ(9) -tetrahydrocannabinol (THC)...
June 22, 2016: Drug Testing and Analysis
https://www.readbyqxmd.com/read/27312859/the-anti-estrogenic-activity-of-indole-3-carbinol-in-neonatal-rat-osteoblasts-is-associated-with-the-estrogen-receptor-antagonist-2-hydroxyestradiol
#12
J Enríquez, R Velázquez-Cruz, A Parra-Torres, R Gutiérrez-Sagal, F Larrea
PURPOSE: To gain new insight into the roles of cruciferous vegetable-derived bioactive phytochemicals in bone cells, we investigated the effects of indole-3-carbinol (I3C) on cell proliferation and differentiation in estradiol (E2)-exposed calvarial osteoblasts that were obtained from neonatal rats. METHODS: Osteoblast activity was assessed by analyzing cellular DNA, cell-associated osteocalcin (OC) levels and alkaline phosphatase (AP) activity. We also examined [(3)H]-estrone (E1) metabolism and estrogen-agonistic and estrogen-antagonistic activities of 2-hydroxy (OH) E1 and 2-OHE2 and their capacity to displace [(3)H]-E2 at ER binding sites using competition studies...
October 2016: Journal of Endocrinological Investigation
https://www.readbyqxmd.com/read/27311563/saturation-mutagenesis-on-tyr205-of-the-cyclic-dipeptide-c2-prenyltransferase-ftmpt1-results-in-mutants-with-strongly-increased-c3-prenylating-activity
#13
Kang Zhou, Wei Zhao, Xiao-Qing Liu, Shu-Ming Li
The fungal indole prenyltransferase FtmPT1 is involved in the biosynthesis of fumitremorgins and catalyzes, in the presence of dimethylallyl diphosphate, a predominant regular prenylation of cyclo-L-Trp-L-Pro (brevianamide F) at position C-2 of the indole nucleus. Analysis of the substrate-bound structure of FtmPT1 revealed that brevianamide F forms a hydrogen bond via its carbonyl oxygen in the diketopiperazine moiety with the hydroxyl group of Tyr205 near the center of the prenyltransferase (PT) barrel. In this study, Tyr205 was mutated to 19 other proteinogenic amino acids by one-step site-directed mutagenesis...
June 16, 2016: Applied Microbiology and Biotechnology
https://www.readbyqxmd.com/read/27194519/development-of-a-mass-spectrometric-hydroxyl-position-determination-method-for-the-hydroxyindole-metabolites-of-jwh-018-by-gc-ms-ms
#14
Maiko Kusano, Kei Zaitsu, Mayumi Yamanaka, Kazuaki Hisatsune, Tomomi Asano, Kentaro Taki, Yumi Hayashi, Hitoshi Tsuchihashi, Akira Ishii
One of the many issues of designer drugs of abuse like synthetic cannabinoids (SCs) such as JWH-018 is that details on their metabolism has yet to be fully elucidated and that multiple metabolites exist. The presence of isomeric compounds poses further challenges in their identification. Our group has previously shown the effectiveness of gas chromatography-electron ionization-tandem mass spectrometry (GC-EI-MS/MS) in the mass spectrometric differentiation of the positional isomers of the naphthoylindole-type SC JWH-081, and speculated that the same approach could be used for the metabolite isomers...
May 2016: Journal of Mass Spectrometry: JMS
https://www.readbyqxmd.com/read/27136975/the-conformational-space-of-the-neurotransmitter-serotonin-how-the-rotation-of-a-hydroxyl-group-changes-all
#15
Martin Wilke, Christian Brand, Josefin Wilke, Michael Schmitt
The 5-hydroxytryptamine receptors (5HTn) are optimized for 5-hydrotryptamine molecules, resulting in a significantly enhanced psychoactive response compared with the 4-, 6-, 7-isomers. This is despite their relatively similar energetic stabilities, excited state lifetimes and emission characteristics. In this work we investigate the conformational space of serotonin (5-hydroxytryptamine) using a combination of rotationally resolved electronic spectroscopy and ab initio calculations. The geometries of the four most abundant conformers are assigned from their molecular parameters in the electronic ground and excited state...
May 11, 2016: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/27124734/interactions-of-indole-derivatives-with-%C3%AE-cyclodextrin-a-quantitative-structure-property-relationship-study
#16
Milan Šoškić, Ivana Porobić
Retention factors for 31 indole derivatives, most of them with auxin activity, were determined by high-performance liquid chromatography, using bonded β-cyclodextrin as a stationary phase. A three-parameter QSPR (quantitative structure-property relationship) model, based on physico-chemical and structural descriptors was derived, which accounted for about 98% variations in the retention factors. The model suggests that the indole nucleus occupies the relatively apolar cavity of β-cyclodextrin while the carboxyl group of the indole -3-carboxylic acids makes hydrogen bonds with the hydroxyl groups of β-cyclodextrin...
2016: PloS One
https://www.readbyqxmd.com/read/27064507/synthesis-of-benzofuranyl-and-indolyl-methyl-azides-by-tandem-silver-catalyzed-cyclization-and-azidation
#17
Gadi Ranjith Kumar, Yalla Kiran Kumar, Ruchir Kant, Maddi Sridhar Reddy
Ag(i)-catalyzed synthesis of 2-azidomethyl benzofurans/indoles from linear and readily available hydroxyl/amino-phenyl propargyl alcohols is described via a highly regioselective C-O and C-N bond formation. Control experiments reveal that the reaction involves the sequential Ag(i)-catalyzed 5-exo-dig cyclization and a catalyst free γ-allylic azidation. The synthetic utility of this method has been demonstrated by using the azidomethyl unit of the above synthesized heterocycles as the base for a variety of other functionalizations, such as triazole-, tetrazole-, amide-, amine-, and pyrido-derivatives...
April 26, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27040658/design-synthesis-and-cytotoxicity-of-pyrano-4-3-b-indol-1-5h-ones-a-hybrid-pharmacophore-approach-via-gold-catalyzed-cyclization
#18
Chandrasekar Praveen, D Babu Ananth
Reported herein is the gold(III)-catalyzed 6-endo-dig cycloisomerization of 2-alkynyl-indole-3-carboxylic acids to form pyrano[4,3-b]indol-1(5H)-ones, which are pharmaceutically important structural motifs. The hitherto unknown substrates required for this methodology were conveniently synthesized in five steps with good overall yields. The utility of this new cycloisomerization is demonstrated by the excellent regioselectivity obtained using a range of substrates. The mildness of the method allowed functional group compatibility towards hydroxyl tether, displaying exquisite chemoselectivity...
May 15, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27032077/bioactivation-of-heterocyclic-aromatic-amines-by-udp-glucuronosyltransferases
#19
Tingting Cai, Lihua Yao, Robert J Turesky
2-Amino-9H-pyrido[2,3-b]indole (AαC) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are carcinogenic heterocyclic aromatic amines (HAA) that arise during the burning of tobacco and cooking of meats. UDP-glucuronosyltransferases (UGT) detoxicate many procarcinogens and their metabolites. The genotoxic N-hydroxylated metabolite of AαC, 2-hydroxyamino-9H-pyrido[2,3-b]indole (HONH-AαC), undergoes glucuronidation to form the isomeric glucuronide (Gluc) conjugates N(2)-(β-d-glucosidurony1)-2-hydroxyamino-9H-pyrido[2,3-b]indole (AαC-HON(2)-Gluc) and O-(β-d-glucosidurony1)-2-hydroxyamino-9H-pyrido[2,3-b]indole (AαC-HN(2)-O-Gluc)...
May 16, 2016: Chemical Research in Toxicology
https://www.readbyqxmd.com/read/27002397/antifungal-indole-alkaloids-from-winchia-calophylla
#20
Mei-Li Yang, Jia Chen, Meng Sun, Dong-Bo Zhang, Kun Gao
Ten indole alkaloids (1-10) were obtained from an antifungal extract of Winchia calophylla, of which two (2 and 4) were new. N(4)-Methyl-10-hydroxyl-desacetylakuammilin (2) was an akuammiline-type indole alkaloid. N(1)-Methyl-echitaminic acid (4) was an unusual zwitterion with a basic vincorine-type skeleton. This is the first report of 10 in W. calophylla. The structures of all of the compounds were determined based on spectroscopic data, and their bioactivities were assessed. Compound 1 showed potent activity against the plant pathogenic fungi of Penicillium italicum and Fusarium oxysporum f...
May 2016: Planta Medica
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