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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, ...201323515836
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 ...201323455027
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 ...201323391590
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 ...201323299916
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 ...201323153056
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 ...201324038685
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 ...201424012108
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 ...201423872898
synthesis of two new hydroxylated derivatives of spironolactone by microbial transformation.spironolactone is a medicinally important molecule that is clinically used in the treatment and management of many diseases such as oedema and ascites in cirrhosis of the liver, malignant ascites, nephrotic syndrome, chronic lung disease, resistant hypertension, congestive heart failure, and primary hyperaldosteronism. microbial transformations of spironolactone by cunninghamella elegans atcc 9245 was carried out. two new hydroxylated derivatives, 12β-hydroxy-spironolactone and 2α-hydroxy-spiron ...201424894559
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 ...201424590203
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 ...201424474678
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 ...201424306727
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 ...201424291799
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 ...201424134149
isolation and characterization of a β-glucuronide of hydroxylated sarm s1 produced using a combination of biotransformation and chemical oxidation.in this study, using mass spectrometry and nuclear magnetic resonance (nmr) spectroscopy, it has been confirmed that biotransformation with the fungus cunninghamella elegans combined with chemical oxidation with the free radical tetramethylpiperidinyl-1-oxy (tempo) can produce drug glucuronides of β-configuration. glucuronic acid conjugates are a common type of metabolites formed by the human body. the detection of such conjugates in doping control and other kinds of forensic analysis would be b ...201424879518
green conversion of agroindustrial wastes into chitin and chitosan by rhizopus arrhizus and cunninghamella elegans strains.this article sets out a method for producing chitin and chitosan by cunninghamella elegans and rhizopus arrhizus strains using a green metabolic conversion of agroindustrial wastes (corn steep liquor and molasses). the physicochemical characteristics of the biopolymers and antimicrobial activity are described. chitin and chitosan were extracted by alkali-acid treatment, and characterized by infrared spectroscopy, viscosity and x-ray diffraction. the effectiveness of chitosan from c. elegans and ...201424853288
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 ...201424841967
biotransformation of dianabol with the filamentous fungi and β-glucuronidase inhibitory activity of resulting metabolites.biotransformation of the anabolic steroid dianabol (1) by suspended-cell cultures of the filamentous fungi cunninghamella elegans and macrophomina phaseolina was studied. incubation of 1 with c. elegans yielded five hydroxylated metabolites 2-6, while m. phaseolina transformed compound 1 into polar metabolites 7-11. these metabolites were identified as 6β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (2), 15α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (3), 11α,17β-dihydroxy-17α-methylandros ...201424755238
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 ...201424321603
a new and fast dllme-ce method for the enantioselective analysis of zopiclone and its active metabolite after fungal biotransformation.zopiclone (zo) is a chiral drug that undergoes extensive metabolism to n-desmethylzopiclone (n-des-zo) and zopiclone-n-oxide (n-ox-zo). pharmacological studies have shown (s)-n-des-zo metabolite presents anxiolytic activity and a patent for this metabolite was requested for anxiety treatment and related disorders. in this context, biotransformation employing fungi may be a promising strategy to obtain n-des-zo. to perform the biotransformation study in this work, an enantioselective method based ...201525778930
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).201526044265
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 ...201525665503
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 ...201525209992
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 ...201525025602
studies on drug metabolism by fungi colonizing decomposing human cadavers. part ii: biotransformation of five model drugs by fungi isolated from post-mortem material.the present study investigated the in vitro metabolic capacity of 28 fungal strains isolated from post-mortem material towards five model drugs: amitriptyline, metoprolol, mirtazapine, promethazine, and zolpidem. each fungal strain was incubated at 25 °c for up to 120 h with each of the five models drugs. cunninghamella elegans was used as positive control. aliquots of the incubation mixture were centrifuged and 50 μl of the supernatants were diluted and directly analyzed by liquid chromatograph ...201524898183
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 ...201526195554
combat-related pythium aphanidermatum invasive wound infection: case report and discussion of utility of molecular diagnostics.we describe a 22-year-old soldier with 19% total body surface area burns, polytrauma, and sequence- and culture-confirmed pythium aphanidermatum wound infection. antemortem histopathology suggested disseminated pythium infection, including brain involvement; however, postmortem pcr revealed cunninghamella elegans, lichtheimia corymbifera, and saksenaea vasiformis coinfection. the utility of molecular diagnostics in invasive fungal infections is discussed.201525832301
carbazole hydroxylation by the filamentous fungi of the cunninghamella species.nitrogen heterocyclic compounds, especially carbazole, quinolone, and pyridine are common types of environmental pollutants. carbazole has a toxic influence on living organisms, and the knowledge of its persistence and bioconversion in ecosystems is still not complete. there is an increasing interest in detoxification of hazardous xenobiotics by microorganisms. in this study, the ability of three filamentous fungi of the cunninghamella species to eliminate carbazole was evaluated. the cunningham ...201526276273
the potentiality of cross-linked fungal chitosan to control water contamination through bioactive filtration.water contamination, with heavy metals and microbial pathogens, is among the most dangerous challenges that confront human health worldwide. chitosan is a bioactive biopolymer that could be produced from fungal mycelia to be utilized in various applied fields. an attempt to apply fungal chitosan for heavy metals chelation and microbial pathogens inhibition, in contaminated water, was performed in current study. chitosan was produced from the mycelia of aspergillus niger, cunninghamella elegans, ...201626995612
new insight into microbial diversity and functions in traditional vietnamese alcoholic fermentation.the roles of microorganisms in traditional alcoholic fermentation are often assumed based on abundance in the starter and activity in pure culture. there is a serious lack of hard evidence on the behavior and activity of individual microbial species during the actual fermentation process. in this study, microbial succession and metabolite changes during 7days of traditional vietnamese alcoholic fermentation were monitored. special attention was devoted to starch degradation. in total, 22 microbi ...201627236224
bio-clarification of water from heavy metals and microbial effluence using fungal chitosan.water pollution is among the most hazardous problems that threaten human health worldwide. chitosan is a marvelous bioactive polymer that could be produced from fungal mycelia. this study was conducted to produce chitosan from cunninghamella elegans and to use it for water pollutants elimination, e.g. heavy metals and waterborne microorganisms, and to investigate its antibacterial mode of action against escherichia coli. the produced fungal chitosan had a deacetylation degree of 81%, a molecular ...201626645148
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 ...201627541932
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 ...201627285201
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 ...201627020303
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].201626977432
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 ...201626907475
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 ...201626810790
evaluation of diuron tolerance and biotransformation by fungi from a sugar cane plantation sandy-loam soil.microorganisms capable of degrading herbicides are essential to minimize the amount of chemical compounds that may leach into other environments. this work aimed to study the potential of sandy-loam soil fungi to tolerate the herbicide herburon (50% diuron) and to degrade the active ingredient diuron. verticillium sp. f04, trichoderma virens f28, and cunninghamella elegans b06 showed the highest growth in the presence of the herbicide. the evaluation of biotransformation showed that aspergillus ...201627960295
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 ...201727918992
biotransformation of bromhexine by cunninghamella elegans, c. echinulata and c. blakesleeana.fungi is a well-known model used to study drug metabolism and its production in in vitro condition. we aim to screen the most efficient strain of cunninghamella sp. among c. elegans, c. echinulata and c. blakesleeana for bromhexine metabolites production. we characterized the metabolites produced using various analytical tools and compared them with mammalian metabolites in rat liver microsomes (rlm). the metabolites were collected by two-stage fermentation of bromhexine with different strains o ...201727988088
can fungi compete with marine sources for chitosan production?chitosan, a β-1,4-linked glucosamine polymer is formed by deacetylation of chitin. it has a wide range of applications from agriculture to human health care products. chitosan is commercially produced from shellfish, shrimp waste, crab and lobster processing using strong alkalis at high temperatures for long time periods. the production of chitin and chitosan from fungal sources has gained increased attention in recent years due to potential advantages in terms of homogenous polymer length, high ...201728143744
enantioselective resolution of (r,s)-carvedilol to (s)-(-)-carvedilol by biocatalysts.among the microorganisms employed in the study, aspergillus niger (gufcc5443), escherichia coli (atcc9637), streptomyces halstedii (ckm-2), pseudomonas putida (ncib9494), cunninghamella elegans (ncim689) and sphingomonas paucimobilis (nctc11030) were capable for the enantioselective conversion of racemic carvedilol. immobilization technique enhanced the enantioselectivity of microorganisms and thus increased the enantiomeric purity of the drug. excellent enantiomeric ratios (e) were found in rea ...201728064425
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 ...201728373049
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 ...201728216250
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