| biotransformation of synthetic cannabinoids jwh-018, jwh-073 and am2201 by cunninghamella elegans. | being marketed as "legal" smoking blends or mixtures, synthetic cannabinoids are abused widely owing to its cannabis-like effect. due to the rapid introduction of new generation analogues of synthetic cannabinoids to escape from legislative/judicial control, the investigation of the metabolic pathways of these substances is of particular importance for drug control, abstinence and forensic toxicology purposes. in this study, the in vitro metabolism of jwh-018, jwh-073 and am2201 by the fungus cu ... | 2016 | 26907475 |
| targeted fluorination of a nonsteroidal anti-inflammatory drug to prolong metabolic half-life. | in drug design, one way of improving metabolic stability is to introduce fluorine at a metabolically labile site. in the early stages of drug design, identification of such sites is challenging, and a rapid method of assessing the effect of fluorination on a putative drug's metabolic stability would be of clear benefit. one approach to this is to employ micro-organisms that are established as models of drug metabolism in parallel with the synthesis of fluorinated drug analogues. in this study, w ... | 2014 | 24474678 |
| tributyltin (tbt) induces oxidative stress and modifies lipid profile in the filamentous fungus cunninghamella elegans. | to investigate the response of the tributyltin-degrading fungal strain cunninghamella elegans to the organotin, a comparative lipidomics strategy was employed using an lc/ms-ms technique. a total of 49 lipid species were identified. individual phospholipids were then quantified using a multiple reaction monitoring method. tributyltin (tbt) caused a decline in the amounts of many molecular species of phosphatidylethanolamine or phosphatidylserine and an increase in the levels of phosphatidic acid ... | 2014 | 24306727 |
| characterization of in vitro and in vivo metabolites of carnosic acid, a natural antioxidant, by high performance liquid chromatography coupled with tandem mass spectrometry. | carnosic acid (ca) is a widely employed antioxidant and the main active component in rosemary and sage, but its metabolism remains largely unknown. the present study investigated the metabolism of ca in vitro and in vivo for the first time, using high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry (hplc-q-trap-ms). a couple of scan modes were adopted in mass spectrometer domain, including q1 full scan, neutral loss scan-information depen ... | 2014 | 24291799 |
| microbial transformation of acetyl-11-keto-boswellic acid by cunninghamella elegans. | microbial biotransformation of acetyl-11-keto-boswellic acid by cunninghamella elegans as 3.1207 was carried out, and totally four transformed products were isolated. on the basis of the extensive spectral data, their structures were characterized as 7β-hydroxy-11-keto-boswellic acid (1), 7β,30-dihydroxy-11-keto-boswellic acid (2), 7β,16α-dihydroxy-3-acetyl-11-keto-boswellic acid (3), and 7β,15α,21β-trihydroxy-3-acetyl-11-keto-boswellic acid (4), respectively. among them, products 1 and 2 are th ... | 2013 | 24168329 |
| evaluation of dispersive liquid-liquid microextraction in the stereoselective determination of cetirizine following the fungal biotransformation of hydroxyzine and analysis by capillary electrophoresis. | we developed a capillary electrophoresis (ce) and dispersive liquid-liquid microextraction (dllme) method to stereoselectively analyze hydroxyzine (hz) and cetirizine (ctz) in liquid culture media. the ce analyses were performed on an uncoated fused-silica capillary; 50mmoll(-1) sodium borate buffer (ph 9.0) containing 0.8% (w/v) s-β-cd was used as the background electrolyte. the applied voltage and temperature were +6 kv and 15 °c, respectively, and the uv detector was set to 214 nm. chloroform ... | 2013 | 24148469 |
| tolerance and growth of 11 trichoderma strains to crude oil, naphthalene, phenanthrene and benzo[a]pyrene. | petroleum hydrocarbons (phs) are major organic contaminants in soils, whose degradation process is mediated by microorganisms such as the filamentous fungi cunninghamella elegans and phanerochaete chrysosporium. however, little is known about the tolerance and the degradation capability of trichoderma species when exposed to ph. this research evaluated the tolerance and growth of 11 trichoderma strains to crude oil (coil), naphthalene (naph), phenanthrene (phe) and benzo[a]pyrene (b[a]p) by usin ... | 2010 | 20869805 |
| effects of 7-hydroxycalamenene isolated from croton cajucara essential oil on growth, lipid content and ultrastructural aspects of rhizopus oryzae. | the leaves and bark of croton cajucara, a shrub from the amazon region, have been used in folk medicine to treat diabetes, malaria, and gastrointestinal and liver disorders. the essential oil from the leaves, rich in linalool, presented antileishmanial and antimicrobial activities. a chemotype of this species was found with an essential oil rich in 7-hydroxycalamenene. during our studies of the c. cajucara essential oil, we isolated 7-hydroxycalamenene at > 98 % purity. the minimum inhibitory co ... | 2014 | 24841967 |
| butyltins degradation by cunninghamella elegans and cochliobolus lunatus co-culture. | organotin compounds are ubiquitous in environment. however, biodegradation of tributyltin (tbt) and dibutyltin (dbt) to non toxic metabolites by fungi has been seldom observed. in this study we constructed a fungal co-culture with an efficient ability of tbt and its metabolites removal. the microscopic fungus strain cunninghamella elegans degraded tbt via hydroxybutyldibutyltin (ohbudbt) to its metabolites: dbt and monobutyltin (mbt), which were then transformed by cochliobolus lunatus. the sequ ... | 2012 | 23314396 |
| enhanced biotransformation of fluoranthene by intertidally derived cunninghamella elegans under biofilm-based and niche-mimicking conditions. | the aims of the investigation were to ascertain if surface attachment of cunninghamella elegans and niche intertidal conditions provided in a bioreactor influenced biotransformation of fluoranthene by c. elegans. a newly designed polymethylmethacrylate (pmma) conico-cylindrical flask (ccf) holding eight equidistantly spaced rectangular strips mounted radially on a circular disc allowed comparison of fluoranthene biotransformation between ccfs with a hydrophobic surface (pmma-ccf) and a hydrophil ... | 2013 | 24038685 |
| the legionella pneumophila siderophore legiobactin is a polycarboxylate that is identical in structure to rhizoferrin. | legionella pneumophila, the agent of legionnaires' disease, secretes a siderophore (legiobactin) that promotes bacterial infection of the lung. in past work, we determined that cytoplasmic lbta (from legiobactin gene a) promotes synthesis of legiobactin, inner membrane lbtb aids in export of the siderophore, and outer membrane lbtu and inner membrane lbtc help mediate ferrilegiobactin uptake and assimilation. however, the past studies examined legiobactin contained within bacterial culture super ... | 2015 | 26195554 |
| biotransformation of bavachinin by three fungal cell cultures. | biotransformation of bavachinin (1) was investigated using three fungal cell cultures of aspergillus flavus atcc 30899, cunninghamella elegans cicc 40250 and penicillium raistrickii atcc 10490, respectively. two major converted products were identified by lc/ms, (1)h nmr and (13)c nmr and x-ray diffraction. two biocatalyst systems, a. flavus atcc 30899 and c. elegans cicc 40250 cell cultures, showed a great capacity of hydroxylation and two hydroxyl groups were attached at c-2″ and c-3″ position ... | 2014 | 24012108 |
| studies on the metabolism of five model drugs by fungi colonizing cadavers using lc-esi-ms/ms and gc-ms analysis. | it is well-known that cadavers may be colonized by microorganisms, but there is limited information if or to what extent these microbes are capable of metabolizing drugs or poisons, changing the concentrations and metabolic pattern of such compounds in postmortem samples. the aim of the present study was to develop a fungal biotransformation system as an in vitro model to investigate potential postmortem metabolism by fungi. five model drugs (amitriptyline, metoprolol, mirtazapine, promethazine, ... | 2012 | 22825674 |
| effects of chitosan from cunninghamella elegans on virulence of post-harvest pathogenic fungi in table grapes (vitis labrusca l.). | this study aimed to obtain chitosan (chi) from cunninghamella elegans cultivated in corn step liquid (csl)-based medium under optimized conditions and to assess the efficacy of the obtained chi in inhibiting botrytis cinerea and penicillium expansum in laboratory media and when applied as a coating on table grapes (vitis labrusca l.). moreover, the influence of chi-based coatings on several physical, physicochemical and sensory characteristics of the fruits during storage was assessed. according ... | 2014 | 24321603 |
| investigation of the metabolites of the hif stabilizer fg-4592 (roxadustat) in five different in vitro models and in a human doping control sample using high resolution mass spectrometry. | fg-4592 is a hypoxia-inducible factor (hif) stabilizer, which can increase the number of red blood cells in the body. it has not been approved by regulatory authorities, but is available for purchase on the internet. due to its ability to improve the oxygen transportation mechanism in the body, fg-4592 is of interest for doping control laboratories, but prior to this study, little information about its metabolism was available. in this study, the metabolism of fg-4592 was investigated in a human ... | 2017 | 27918992 |
| in vitro metabolism of monensin a: microbial and human liver microsomes models. | 1. monensin a, an important antibiotic ionophore that is primarily employed to treat coccidiosis, selectively complexes and transports sodium cations across lipid membranes and displays a variety of biological properties. 2. in this study, we evaluated the fungi cunninghamella echinulata var. elegans atcc 8688a, cunninghamella elegans nrrl 1393 atcc 10028b and human hepatic microsomes as cyp-p450 models to investigate the in vitro metabolism of monensin a and compare the products with the metabo ... | 2014 | 24134149 |
| dna barcoding in mucorales: an inventory of biodiversity. | the order mucorales comprises predominantly fast-growing saprotrophic fungi, some of which are used for the fermentation of foodstuffs but it also includes species known to cause infections in patients with severe immune or metabolic impairments. to inventory biodiversity in mucorales its barcodes of 668 strains in 203 taxa were generated covering more than two thirds of the recognised species. using the its sequences, molecular operational taxonomic units were defined by a similarity threshold ... | 2013 | 24027345 |
| biotransformation of fluorophenyl pyridine carboxylic acids by the model fungus cunninghamella elegans. | 1. fluorine plays a key role in the design of new drugs and recent fda approvals included two fluorinated drugs, tedizolid phosphate and vorapaxar, both of which contain the fluorophenyl pyridyl moiety. 2. to investigate the likely phase-i (oxidative) metabolic fate of this group, various fluorinated phenyl pyridine carboxylic acids were incubated with the fungus cunninghamella elegans, which is an established model of mammalian drug metabolism. 3. (19)f nmr spectroscopy established the degree o ... | 2016 | 27541932 |
| biotransformation of salpichrolides a, c, and g by three filamentous fungi. | incubation of salpichrolide a (1) with rhizomucor miehei produced hydroxylation in rings b and c (c-7 and c-12) and led to c-5-c-6 epoxide opening, while incubation of salpichrolides c (2) and g (3) with r. miehei led to epoxide opening at the c-24-c-25 and c-5-c-6 positions, respectively. biotransformation of salpichrolide a (1) with cunninghamella elegans produced stereoselective hydroxylated, oxidized, and reduced derivatives in different positions of the a, b, and c rings and c-5-c-6 epoxide ... | 2016 | 27285201 |
| evaluation of fluorinated biphenyl ether pro-drug scaffolds employing the chemical-microbial approach. | incorporation of fluorine in a drug can dramatically affect its metabolism and methods to assess the effect of fluorine substitution on drug metabolism are required for effective drug design. employing a previously developed chemical-microbial method the metabolism of a series of fluorinated biphenyl ethers was determined. the substrates were synthesized via ullmann-type condensation reactions between bromotoluene and fluorophenol. the ethers were incubated with the fungus cunninghamella elegans ... | 2016 | 27020303 |
| data on individual metabolites of synthetic cannabinoids jwh-018, jwh-073 and am2201 by cunninghamella elegans. | synthetic cannabinoids jwh-018, jwh-073 and am2201 were metabolised by the fungus cunninghamella elegans. in this article, data on individual metabolites of their retention times, mass accuracies, major product ions and structures indicated by product ions are presented. the data in this article is related to "biotransformation of synthetic cannabinoids jwh-018, jwh-073 and am2201 by cunninghamella elegans" [1]. | 2016 | 26977432 |
| cunninghamella as a microbiological model for metabolism of histamine h(3) receptor antagonist 1-[3-(4-tert-butylphenoxy)propyl]piperidine. | the aim of the study was to analyze the ability of the microorganism cunninghamella to carry out the biotransformation of 1-[3-(4-tert-butylphenoxy)propyl]piperidine (dl76) and to compare the obtained results with in silico models. biotransformation was carried out by three strains of filamentous fungus: cunninghamella echinulata, cunninghamella blakesleeana, and cunninghamella elegans. most probable direction of dl76 metabolic transition was the oxidation of the methyl group in the tert-butyl m ... | 2012 | 22983742 |
| enhancement of cunninghamella elegans ucp/wfcc 0542 biomass and chitosan with amino acid supply. | studies were carried out with cunninghamella elegans ucp/wfcc 0542 to evaluate the effects of an abundant supply of amino acids, asparagine and corn steep liquor associated with sucrose on the production of biomass and chitosan by submerged fermentation. the concentrations of the components of the culture medium which were determined by a 2³ full factorial design evaluated the interactions and effects of the independent variables of the sucrose, asparagine and corn steep liquor in relation to ca ... | 2013 | 23973987 |
| fungal chitosan based nanocomposites sponges-an alternative medicine for wound dressing. | the porous structured and cell proliferative biodegradable fungal chitosan (fcs) based composites with potential antibacterial property was prepared with aloe vera extract (ale) and the plant cuscuta reflexa mediated biosynthesized silver nanoparticles (cus-agnps) were developed for wound dressing applications by freeze drying method. fungal chitosan was derived from cunninghamella elegans a species belongs the family of zygomycetes. the cus-agnps were characterized by the uv-vis spectrum, xrd a ... | 2017 | 28373049 |
| quinoline biodegradation by filamentous fungus cunninghamella elegans and adaptive modifications of the fungal membrane composition. | quinoline, which belongs to n-heterocyclic compounds, occurs naturally in the environment and is used in numerous industrial processes. the structures of various chemicals, such as dyes and medicines, are based on this compound. due to that fact, quinoline and its derivatives are widely distributed in environment and can exert toxic effects on organisms from different trophic levels. the ability of the filamentous fungus cunninghamella elegans im 1785/21gp to degrade quinoline and modulate the m ... | 2016 | 26810790 |
| characterization of a non-approved selective androgen receptor modulator drug candidate sold via the internet and identification of in vitro generated phase-i metabolites for human sports drug testing. | potentially performance-enhancing agents, particularly anabolic agents, are advertised and distributed by internet-based suppliers to a substantial extent. among these anabolic agents, a substance referred to as lgd-4033 has been made available, comprising the core structure of a class of selective androgen receptor modulators (sarms). | 2015 | 26044265 |
| synthesis, characterization, and detection of new oxandrolone metabolites as long-term markers in sports drug testing. | the discovery and implementation of the long-term metabolite of metandienone, namely 17β-hydroxymethyl-17α-methyl-18-norandrost-1,4,13-trien-3-one, to doping control resulted in hundreds of positive metandienone findings worldwide and impressively demonstrated that prolonged detection periods significantly increase the effectiveness of sports drug testing. for oxandrolone and other 17-methyl steroids, analogs of this metabolite have already been described, but comprehensive characterization and ... | 2013 | 23877183 |
| microbial biotransformation of aryl sulfanylpentafluorides. | we report, for the first time, the biotransformation of potential pollutants bearing the pentafluorosulfanyl (sf5-) functional group in a fungus and bacteria. cunninghamella elegans transformed p-methoxy phenyl sf5 via demethylation; pseudomonas knackmussii and p. pseudoalcaligenes kf707 transformed amino-, hydroxyamino- and diamino- substituted phenyl sf5, forming the n-acetylated derivatives as the main product. cell-free extract of streptomyces griseus transformed 4-amino-3-hydroxy-phenyl sf5 ... | 2014 | 23872898 |
| effect of corn steep liquor (csl) and cassava wastewater (cw) on chitin and chitosan production by cunninghamella elegans and their physicochemical characteristics and cytotoxicity. | microbiological processes were used for chitin and chitosan production with cunninghamella elegans ucp/wfcc 0542 grown in different concentrations of two agro-industrial wastes, corn steep liquor (csl) and cassava wastewater (cw) established using a 2² full factorial design. the polysaccharides were extracted by alkali-acid treatment and characterized by infrared spectroscopy, viscosity, thermal analysis, elemental analysis, scanning electron microscopy and x-ray diffraction. the cytotoxicity of ... | 2014 | 24590203 |
| production of drug metabolites by immobilised cunninghamella elegans: from screening to scale up. | cunninghamella elegans is a fungus that has been used extensively as a microbial model of mammalian drug metabolism, whilst its potential as a biocatalyst for the preparative production of human drug metabolites has been often proposed, little effort has been made to enable this. here, we describe a workflow for the application of c. elegans for the production of drug metabolites, starting from well-plate screening assays leading to the preparative production of drug metabolites using fungus imm ... | 2015 | 25665503 |
| a novel trapping system for the detection of reactive drug metabolites using the fungus cunninghamella elegans and high resolution mass spectrometry. | a new model is presented that can be used to screen for bioactivation of drugs. the evaluation of toxicity is an important step in the development of new drugs. one way to detect possible toxic metabolites is to use trapping agents such as glutathione. often human liver microsomes are used as a metabolic model in initial studies. however, there is a need for alternatives that are easy to handle, cheap, and can produce large amounts of metabolites. in the presented study, paracetamol, mefenamic a ... | 2015 | 25209992 |
| mass spectrometric characterization of glucuronides formed by a new concept, combining cunninghamella elegans with tempo. | a new concept for the production of drug glucuronides is presented and the products formed were characterized using ultra high performance liquid chromatography-high resolution mass spectrometry (uplc-hrms). glucuronic acid conjugates are important phase ii metabolites of a wide range of drugs. there is a lack of commercially available glucuronides and classic synthetic methods are tedious and expensive. thus, new methods of glucuronide synthesis are needed. selective androgen receptor modulator ... | 2013 | 23867089 |
| cadmium tolerance and removal from cunninghamella elegans related to the polyphosphate metabolism. | the aim of the present work was to study the cadmium effects on growth, ultrastructure and polyphosphate metabolism, as well as to evaluate the metal removal and accumulation by cunninghamella elegans (ifm 46109) growing in culture medium. the presence of cadmium reduced growth, and a longer lag phase was observed. however, the phosphate uptake from the culture medium increased 15% when compared to the control. moreover, c. elegans removed 70%-81% of the cadmium added to the culture medium durin ... | 2013 | 23538844 |
| filamentous fungal biofilm for production of human drug metabolites. | in drug development, access to drug metabolites is essential for assessment of toxicity and pharmacokinetic studies. metabolites are usually acquired via chemical synthesis, although biological production is potentially more efficient with fewer waste management issues. a significant problem with the biological approach is the effective half-life of the biocatalyst, which can be resolved by immobilisation. the fungus cunninghamella elegans is well established as a model of mammalian metabolism, ... | 2013 | 23515836 |
| biotransfomation of cyperenoic acid by cunninghamella elegans as 3.2028 and the potent anti-angiogenic activities of its metabolites. | cyperenoic acid (1) is one of the major sesquiterpenes isolated from croton crassifolius, which exhibited potent anti-angiogenic activity. traditional structural modification of 1 is difficult to perform by chemical technology due to the remarkable stability of the patchoulane skeleton. in order to overcome chemical synthesis difficulties and obtain structurally diverse derivations, microbial transformation of 1 by using cunninghamella elegans as 3.2028 was studied for the first time. five new h ... | 2017 | 28216250 |
| polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants. | this study investigated the sorption to soil of water-soluble metabolites from polycyclic aromatic compounds (pacs). the soil fungus cunninghamella elegans was used to produce pac metabolites from two un-substituted pacs (phenanthrene, pyrene), three alkyl-substituted pacs (2-methylnaphthalene, 1-methylphenanthrene, 1-methylpyrene), and one sulfur-containing heterocyclic pac (dibenzothiophene). fifty-eight metabolites were tentatively identified; metabolites from the un-substituted pacs were hyd ... | 2015 | 25025602 |
| fungal transformation of cedryl acetate and α-glucosidase inhibition assay, quantum mechanical calculations and molecular docking studies of its metabolites. | the fungal transformation of cedryl acetate (1) was investigated for the first time by using cunninghamella elegans. the metabolites obtained include, 10β-hydroxycedryl acetate (3), 2α, 10β-dihydroxycedryl acetate (4), 2α-hydroxy-10-oxocedryl acetate (5), 3α,10β-dihydroxycedryl acetate (6), 3α,10α-dihydroxycedryl acetate (7), 10β,14α-dihydroxy cedryl acetate (8), 3β,10β-cedr-8(15)-ene-3,10-diol (9), and 3α,8β,10β -dihydroxycedrol (10). compounds 1, 2, and 4 showed α-glucosidase inhibitory activi ... | 2013 | 23455027 |
| microbial transformation of acetyl-11-keto-β-boswellic acid and their inhibitory activity on lps-induced no production. | the capabilities of 20 strains of fungi to transform acetyl-11-keto-β-boswellic (akba) were screened. and biotransformation of akba by cunninghamella blakesleana as 3.970 afforded five metabolites (1-5), while two metabolites (6, 7) were isolated from biotransformation of cunninghamella elegans as 3.1207. the chemical structures of these metabolites were identified by spectral methods including 2d nmr and their structures were elucidated as 7β-hydroxy-3-acety-11-keto-β-boswellic acid (1), 21β-di ... | 2013 | 23391590 |
| a convenient chemical-microbial method for developing fluorinated pharmaceuticals. | a significant proportion of pharmaceuticals are fluorinated and selecting the site of fluorine incorporation can be an important beneficial part a drug development process. here we describe initial experiments aimed at the development of a general method of selecting optimum sites on pro-drug molecules for fluorination, so that metabolic stability may be improved. several model biphenyl derivatives were transformed by the fungus cunninghamella elegans and the bacterium streptomyces griseus, both ... | 2013 | 23299916 |
| the fungus cunninghamella elegans can produce human and equine metabolites of selective androgen receptor modulators (sarms). | 1. selective androgen receptor modulators (sarms) are a group of substances that have potential to be used as doping agents in sports. being a relatively new group not available on the open market means that no reference materials are commercially available for the main metabolites. in the presented study, the in vitro metabolism of sarms by the fungus cunninghamella elegans has been investigated with the purpose of finding out if it can produce relevant human and equine metabolites. 2. three di ... | 2013 | 23153056 |
| characterization of a new anticancer agent, eapb0203, and its main metabolites: nuclear magnetic resonance and liquid chromatography-mass spectrometry studies. | the present study was conducted to assess the structures of the main unknown oxygenated metabolites of eapb0203. the first step was to assign all the (1)h and (13)c nmr of both eapb0203 and its demethylated metabolite (eapb0202) to the corresponding atoms in their molecular structures and to elucidate the fragmentation pathways for the [m + h](+) ions of these compounds using high-resolution mass spectrometry (ms). ms/ms spectra showed that both protonated molecules possessing an even number of ... | 2012 | 23072539 |
| biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures. | | 2012 | 23021311 |
| microbial transformation of 2-amino-4-methyl-3-nitropyridine. | biotransformation of the highly substituted pyridine derivative 2-amino-4-methyl-3-nitropyridine by cunninghamella elegans atcc 26269 yielded three products each with a molecular weight of 169 da which were identified as 2-amino-5-hydroxy-4-methyl-3-nitropyridine, 2-amino-4-hydroxymethyl-3-nitropyridine, and 2-amino-4-methyl-3-nitropyridine-1-oxide. biotransformation by streptomyces antibioticus atcc 14890 gave two different products each with a molecular weight of 169 da; one was acid labile an ... | 2012 | 22926342 |
| structural elucidation of phase i and ii metabolites of bupivacaine in horse urine and fungi of the cunninghamella species using liquid chromatography/multi-stage mass spectrometry. | bupivacaine is a local anaesthetic prohibited in equine sports. it is highly metabolized in the horse but a thorough description of its metabolite profile is lacking. an administration study should find appropriate analytical targets for doping control. furthermore, knowledge of an in vitro system for production of metabolites would be beneficial. | 2012 | 22555927 |