共查询到20条相似文献,搜索用时 15 毫秒
1.
G. S. Prasad S. Girisham S. M. Reddy K. Srisailam 《World journal of microbiology & biotechnology》2008,24(10):2055-2059
A filamentous fungus Cunninghamella blakesleeana was screened for its ability to biotransform the anthelmintic drug albendazole. The fungus produced three metabolites in
the presence of the carbon and nitrogen sources studied. The transformation was identified by HPLC and the structures of the
transformation products were assigned by LC-MS-MS analysis and on the basis of previous reports. The results indicated that
the fungus metabolized albendazole into albendazole sulfoxide (M1), albendazole sulfone (M2) and an N-methyl metabolite of albendazole sulfoxide (M3). The effect of carbon and nitrogen source on the biotransformation of albendazole
was significant. Among the carbon and nitrogen sources studied, fructose and urea respectively produced maximum extent of
biotransformation in terms of substrate depletion. Among the carbon sources studied, maltose produced a higher percentage
of M1 whereas M2 and M3 were produced to their maximum extent in presence of d-fructose in terms of metabolite per unit quantity of biomass. In the case of nitrogen sources, ammonium acetate, calcium
nitrate and barium nitrate produced maximum percentage of M1, M2 and M3 respectively. The results reveal that the carbon and
nitrogen source significantly influence the microbial transformation both qualitatively and quantitatively. 相似文献
2.
Bonato PS Lanchote VL Takayanagui OM 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》2003,783(1):237-245
This paper describes a simple, fast, sensitive and reliable method for the simultaneous determination of albendazole sulfoxide (ASOX) and albendazole sulfone (ASON), the two most important metabolites of the drug albendazole (ABZ), in plasma samples using liquid chromatography and tandem mass spectrometry. After liquid-liquid extraction with dichloromethane, the two albendazole metabolites and the internal standard phenacetin were resolved in a CN column using the mobile phase methanol-water (4:6, v/v) acidified with 1% acetic acid. Detection by electrospray mass spectrometry was carried out in the positive ion mode. The method was linear up to 2500 and 250 ng/ml for ASOX and ASON, respectively, with mean recoveries of more than 85%. The precision and accuracy data, based on within- and between-day variations over 5 days, were lower than 15%. The quantitation limits of 0.5 and 5.0 ng/ml for ASON and ASOX are low enough for the method to be suitable for pharmacokinetic studies. Pharmacokinetic data obtained with the proposed method following oral administration of ABZ to a patient with neurocysticercosis are also reported. 相似文献
3.
S. B. Chincholkar R. Seeta Laxman R. D. Wakharkar 《World journal of microbiology & biotechnology》1995,11(3):357-358
Progesterone was completely hydroxylated, principally to 11,14 dihydroxyprogesterone by Cunninghamella blakesleeana NCIM 687 in 48h.S.B. Chincholkar is with the Microbiology Division, Department of Life Sciences, North Maharashtra University, Jalgaon 425 001, India. R. Seeta Laxman is with the Division of Biochemical Sciences, National Chemical Laboratory, Pune 411 008, India. R.D. Wakharkar is with Organic Chemistry. Technology Division, National Chemical Laboratory, Pune 411 008. India 相似文献
4.
M. Iqbal Choudhary Saira Erum Muhammad Atif Rizwana Malik Naik Tameen Khan Atta-ur-Rahman 《Steroids》2011,76(12):1288-1296
Microbial transformation of (20S)-20-hydroxymethylpregna-1,4-dien-3-one (1) by four filamentous fungi, Cunninghamella elegans, Macrophomina phaseolina, Rhizopus stolonifer, and Gibberella fujikuroi, afforded nine new, and two known metabolites 2–12. The structures of these metabolites were characterized through detailed spectroscopic analysis. These metabolites were obtained as a result of biohydroxylation of 1 at C-6β, -7β, -11α, -14α, -15β, -16β, and -17α positions, except metabolite 2 which contain an O-acetyl group at C-22. These fungal strains demonstrated to be efficient biocatalysts for 11α-hydroxylation. Compound 1, and its metabolites were evaluated for the first time for their cytotoxicity against the HeLa cancer cell lines, and some interesting results were obtained. 相似文献
5.
Ghasemi Younes Mohagheghzadeh Abdolali Moshavash Maryam Ostovan Zahra Rasoul-Amini Sara Morowvat Mohammad Hossein Ghoshoon Mohammad Bagher Raee Mohammad Javad Mosavi-Azam Seyed Bagher 《World journal of microbiology & biotechnology》2009,25(7):1301-1304
The biotransformation of several monoterpenes by the locally isolated unicellular microalga, Oocystis pusilla was investigated. The metabolites were identified by thin layer chromatography and GC/MS. The results showed that O. pusilla had the ability to reduce the C=C double bond in (+)-carvone to yield trans-dihydrocarvone and traces of cis-dihydrocarvone. O. pusilla also converted (+)-limonene to trans-carveol, as the main product, and yielded carvone and trans-limonene oxide. Furthermore, (−)-linalool was converted to trans-furanoid and trans-pyranoid linalool oxide, thymol was converted to thymoquinone, (−)-carveol was converted to carvone and trans-dihydrocarvone, (−)-menthone and (+)-pulegone were converted to menthol, (L)-citronellal was converted to citronellol, and
(+)-β-pinene was converted to trans-pinocarveol. 相似文献
6.
Biotransformation of betulinic and betulonic acids by fungi 总被引:1,自引:0,他引:1
Betulinic acid (1), a triterpenoid found in many plant species, has attracted attention due to its important pharmacological properties, such as anti-cancer and anti-HIV activities. The closely related, betulonic acid (2) also has similar properties. In order to obtain derivatives potentially useful for detailed pharmacological studies, both compounds were submitted to incubations with selected microorganisms. In this work, both were individually metabolized by the fungi Arthrobotrys, Chaetophoma and Dematium, isolated from the bark of Platanus orientalis as well as with Colletotrichum, obtained from corn leaves; such fungal transformations are quite rare in the scientific literature. Biotransformations with Arthrobotrys converted betulonic acid (2) into 3-oxo-7beta-hydroxylup-20(29)-en-28-oic acid (3), 3-oxo-7beta,15alpha-dihydroxylup-20(29)-en-28-oic acid (4) and 3-oxo-7beta,30-dihydroxylup-20(29)-en-28-oic acid (5); Colletotrichum converted betulinic acid (1) into 3-oxo-15alpha-hydroxylup-20(29)-en-28-oic (6) acid whereas betulonic acid (2) was converted into the same product and 3-oxo-7beta,15alpha-dihydroxylup-20(29)-en-28-oic acid (4); Chaetophoma converted betulonic acid (2) into 3-oxo-25-hydroxylup-20(29)-en-28-oic acid (7) and both Chaetophoma and Dematium converted betulinic acid (1) into betulonic acid (2). Those fungi, therefore, are useful for mild, selective oxidations of lupane substrates at positions C-3, C-7, C-15, C-25 and C-30. 相似文献
7.
Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae 总被引:1,自引:0,他引:1
Wang H Liu L Guo YX Dong YS Zhang DJ Xiu ZL 《Applied microbiology and biotechnology》2007,75(4):763-768
Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae was investigated in this study. Resveratrol is widely used in medicine, food, and cosmetic because of its pharmacological
properties. However, it has a much lower content in plants compared with its glucoside piceid, which has a much lower bioavailability.
Traditionally, the aglycone is acquired by acid or enzymatic hydrolysis of its glucoside, but the violent condition and the
acid pollution in hydrolytic reaction and the high cost of the enzyme limit their industrial development. In this paper, fermentation
of P. cuspidatum by A. oryzae was successfully performed, during which, piceid was converted to resveratrol with the highest yield of trans-resveratrol 1.35%, 3.6 times higher than that obtained from raw herb by microwave-assisted extraction. Scale-up production
was also performed and the yield of trans-resveratrol was 3.1 times higher after 24 h incubation. Therefore, biotransformation is a better method to increase the yield
of resveratrol because of its high yield and mild conditions. 相似文献
8.
Xing Zhang Min Ye Yu-jing Gong Lin-Min Feng Si-Jia Tao Jun Yin De-an Guo 《Process Biochemistry》2011,46(10):2064-2067
Pseudolaric acid B (1) is a natural product with potent antifungal activity. We discovered that pseudolaric acid B did not kill but only suppress the growth of the filamentous fungus Chaetomium globosum. It was proposed that pseudolaric acid B was converted to metabolites with decreased antifungal activities. In this study, a scaled-up biotransformation of pseudolaric acid B by C. globosum produced five metabolites, including three new compounds, pseudolaric acid I (2), pseudolaric acid B 18-oyl-alanine (4) and pseudolaric acid B 18-oyl-serine (6), together with two known compounds, pseudolaric acid F (3) and pseudolaric acid B 18-oyl-glycine (5). The structures were characterized by NMR and MS spectroscopy. The major biotransformation reaction was conjugation with amino acids. None of the metabolites showed inhibitory effects on the growth of Candida albicans. The results suggested that biotransformation might be a detoxification process for fungi to resist antifungal drugs. 相似文献
9.
Shyam Prasad G Narasimha Rao K Preethi R Girisham S Reddy SM 《Indian journal of microbiology》2011,51(1):82-87
Influence of carbon and nitrogen source, on biotransformation of meloxicam was studied by employing Cunninghamella blakesleeana NCIM 687 with an aim to achieve maximum transformation of meloxicam and in search of new metabolites. The transformation
was confirmed by HPLC and based on LC–MS–MS data and previous reports the metabolites were predicted as 5-hydroxymethyl meloxicam,
5-carboxy meloxicam and a novel metabolite. The quantification of metabolites was performed using HPLC peak areas. The results
obtained indicate that glucose as carbon source, ammonium nitrate as nitrogen source, were found to be optimum for maximum
transformation of meloxicam. The study suggests the significance of these factors in biotransformation of meloxicam using
microbial cultures. The fermentation was scaled up to 1 l level. 相似文献
10.
Cystic echinococcosis (CE) is caused by the larval stage of Echinococcus granulosus, which in this disease the metacestode develop in visceral organs especially liver and lungs. The disease is present worldwide and affects humans as well as herbivores including cattle, sheep, camels, horses and others. Benzimidazole carbamate derivatives, such as mebendazole and albendazole, are currently used for chemotherapeutic treatment of CE in inoperable patients and have to be applied in high doses for extended periods of time, and therefore adverse side effects are frequently observed. This study was designed to evaluate and compare the in vivo effects of 0.5 mg/kg, BID, albendazole sulfoxide (ricobendazole) and two different therapeutic regimens of 0.5 mg/kg BID and 2 mg/kg every 48 h of albendazole sulfoxide loaded solid lipid nanoparticles. Albendazole sulfoxide loaded solid lipid nanoparticles was prepared by solvent diffusion–evaporation method. Fifty Balb/c mice were infected by intraperitoneal injection of protoscoleces and 8 months post infection, the infected mice were treated for 15 days with the above mentioned regimens. They were then euthanized and the size and weight of the cysts as well as their ultrastructural changes were investigated. Although the cysts showed reduced size and weight in the treated animals but these reductions were not statistically significant. The cysts in the animals which received albendazole sulfoxide loaded SLN every 48 h showed more ultrastructural modification. However, these ultrastructural changes should be supported by further biochemical and molecular studies before introducing it as an efficient therapeutic regimen for treatment of human and animal hydatid disease. 相似文献
11.
Hsu FL Yang LM Chang SF Wang LH Hsu CY Liu PC Lin SJ 《Applied microbiology and biotechnology》2007,74(3):659-666
Preparative-scale fermentation of gallic acid (3,4,5-trihydroxybenzoic acid) (1) with Beauveria sulfurescens ATCC 7159 gave two new glucosidated compounds, 4-(3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-methoxy-benzoic
acid (4), 3-hydroxy-4,5-dimethoxy-benzoic acid 3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yl ester (7), along with four known compounds, 3-O-methylgallic acid (2), 4-O-methylgallic acid (3), 3,4-O-dimethylgallic acid (5), and 3,5-O-dimethylgallic acid (6). The new metabolite genistein 7-O-β-D-4″-O-methyl-glucopyranoside (8) was also obtained as a byproduct due to the use of soybean meal in the fermentation medium. The structural elucidation of
the metabolites was based primarily on 1D-, 2D-NMR, and HRFABMS analyses. Among these compounds, 2, 3, and 5 are metabolites of gallic acid in mammals. This result demonstrated that microbial culture parallels mammalian metabolism;
therefore, B. sulfurescens might be a useful tool for generating mammalian metabolites of related analogs of gallic acid (1) for complete structural identification and for further use in investigating pharmacological and toxicological properties
in this series of compounds. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter gene assay
was used to initially screen for the biological activity of the 6 compounds, 2–6 and 8, along with 1 and its chemical O-methylated derivatives 9–13. Among the 12 compounds tested, 11–13 were found to be significant, but less active than the reference compounds of methylprednisolone and dexamethasone. 相似文献
12.
García-Granados A Fernández A Gutiérrez MC Martínez A Quirós R Rivas F Arias JM 《Phytochemistry》2004,65(1):107-115
Biotransformation of ent-3beta,12alpha-dihydroxy-13-epi-manoyl oxide with Fusarium moniliforme gave the regioselective oxidation of the hydroxyl group at C-3 and the ent-7beta-hydroxylation. The action of Gliocladium roseum in the 3,12-diketoderivative originated monohydroxylations at C-1 and C-7, both by the ent-beta face, while Rhizopus nigricans produced hydroxylation at C-7 or C-18, epoxidation of the double bond, reduction of the keto group at C-3, and combined actions as biohydroxylation at C-2/epoxidation of the double bond and hydroxylation at C-7/reduction of the keto group at C-3. In the ent-3-hydroxy-12-keto epimers, G. roseum originated monohydroxylations at C-1 and C-7 and R. nigricans originated the oxidation at C-3 as a major transformation, epoxidation of double bond and hydroxylation at C-2. Finally, in the ent-3beta-hydroxy epimer R. nigricans also originated minor hydroxylations at C-1, C-6, C-7 and C-20 and F. moniliforme produced an hydroxylation at C-7 and a dihydroxylation at C-7/C-11. 相似文献
13.
Microbial transformation of adrenosterone (1) by suspended-cell cultures of the filamentous fungus Cunninghamella elegans resulted in the production of five metabolites 2-6, which were identified as 9alpha-hydroxyadrenosterone (2), 11-ketotestosterone (3), 6beta-hydroxyadrenosterone (4), 9alpha-hydroxy-11-ketotestosterone (5), and 6beta-hydroxy-11-ketotestosterone (6). Structures of new metabolites 2, 5, and 6 were established by single-crystal X-ray diffraction analysis. 相似文献
14.
Merino G Molina AJ García JL Pulido MM Prieto JG Alvarez AI 《Comparative biochemistry and physiology. Toxicology & pharmacology : CBP》2003,136(1):9-15
Herbal products show potential drug interactions, some of them with adverse effects. The main aim of this work was to study the effect of Panax ginseng on the intestinal elimination of the benzimidazole derivative albendazole sulfoxide (ABZSO). An upper small intestine segment was isolated and perfused in situ with saline, while ABZSO solution (10 mg/kg i.v.) was administered intravenously. Blood samples and intestinal secretion were collected over 60 min and analysed by HPLC. The intestinal clearance of ABZSO was 0.106+/-0.010 ml/min. Systemic co-administration of ginseng (10 mg/kg i.v.) increased significantly (P<0.05) the clearance of ABZSO (0.132+/-0.005 ml/min). The increase in ABZSO elimination could be the result of the effect of ginseng on metabolic pathways. These results highlight the interactions between herbal products (sometimes dietary constituents) and drugs such as benzimidazoles, since ginseng modifies the luminal clearance of this anthelminthic drug and could potentially interfere with drugs that undergo the same intestinal processes. 相似文献
15.
Suspension cultured cells of Caragana chamlagu (Leguminosae) converted zerumbone (1) into zerumbone epoxide (2) as the intermediate, (2R,3R,7R)-2,3-epoxy-9-humulen-8-one (3) and (2R,3S,7R)-2,3-epoxy-9-humulen-8-one (4) as new sesquiterpenes in 11%, 36% and 21% yields, respectively. 相似文献
16.
Toyokazu Yoshida Mitsuaki Kito Masahiko Tsujii Toru Nagasawa 《Biotechnology letters》2001,23(15):1217-1222
Microbial oxidation of 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylthiobenzimidazole to a useful proton pump inhibitor, sodium 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl] methylsulfinyl]-1H benzimidazole (Rabeprazole), was examined in over 650 microorganisms. Rabeprazole-forming activity was distributed in molds. The mold with the highest activity was identified as Cunninghamella echinulata. Glucose, when added to the reaction mixture, gave the highest accumulation of Rabeprazole (6.9 mM, 2.5 g l–1) with a molar conversion ratio of 92% without the formation of the sulfone form as undesired product and resulted in the exclusive formation of (S) enantiomer (>99% e.e.). 相似文献
17.
Andrew S. Lamm Avril R.M. Chen William F. Reynolds Paul B. Reese 《Journal of Molecular Catalysis .B, Enzymatic》2009,59(4):292-296
Santonin (1) was incubated with separate growing cultures of Aspergillus niger ATCC 9142, Mucor plumbeus ATCC 4740, Whetzelinia sclerotiorum ATCC 18687, Cunninghamella echinulata var. elegans ATCC 8688a and Phanerochaete chrysosporium ATCC 24725. Three novel metabolites were isolated: 11β,13-dihydroxysantonin (3), 6,7-dehydosantonin (5) and 3,6-dihydroxy-9-keto-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (7). 11β-Hydroxysantonin (2), 14-hydroxysantonin (4) and 3,6,9-trihydroxy-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (6) were also isolated. Hydroxylation at C-9 followed by a retro-aldol reaction was postulated to have produced 6 and 7. Through the synthesis and fermentation of the santonin analogues: tetrahydrosantonin (8) and α-desmotroposantonin (12), several new compounds were obtained; the most significant being 9-keto-desmotroposantonin (14), which was indicative of C-9 monohydroxylation. 相似文献
18.
Huifeng Li Min Ye Hongzhu Guo Yin Tian Jie Zhang Jianping Zhou Yuchi Hu Dean Guo 《Phytochemistry》2009,70(11-12):1416-1420
Biotransformation of 20(S)-protopanaxadiol (1) by the fungus Mucor spinosus AS 3.3450 yielded eight metabolites (2–9). On the basis of NMR and MS analyses, the metabolites were identified as 12-oxo-15α,27-dihydroxyl-20(S)-protopanaxadiol (2), 12-oxo-7β,11α,28-trihydroxyl-20(S)-protopanaxadiol (3), 12-oxo-7β,28-dihydroxyl-20(S)-protopanaxadiol (4), 12-oxo-15α,29-dihydroxyl-20(S)-protopanaxadiol (5), 12-oxo-7β,15α-dihydroxyl-20(S)-protopanaxadiol (6), 12-oxo-7β,11β-dihydroxyl-20(S)-protopanaxadiol (7), 12-oxo-15α-hydroxyl-20(S)-protopanaxadiol (8), and 12-oxo-7β-hydroxyl-20(S)-protopanaxadiol (9), respectively. Among them, 2–5, 7, and 8 are new compounds. These results indicated that M. spinosus could catalyze the specific C-12 dehydrogenation of 20(S)-protopanaxadiol, as well hydroxylation at different positions. These biocatalytic reactions may be difficult for chemical synthesis. The biotransformed products showed weak in vitro cytotoxic activities. 相似文献
19.
D.J. Fletouris N.A. Botsoglou I.E. Psomas A.I. Mantis 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》1996,687(2):713
Analytical methodology for determination of albendazole and its sulphoxide and sulphone metabolites in milk at levels down to 2–5 ng/ml has been developed. Extraction was carried out with ethyl acetate under alkaline conditions, and extracts were analyzed on a silica-based C18 column in the presence of positively-charged pairing ions. Accuracy data showed overall recoveries ranged from 78.4% to 100%, whereas precision data, based on within- and between-day variation, suggested overall precision values better than 4.9%. The method was successfully applied to determine residues in milk of a dairy cow orally given albendazole. 相似文献
20.
Biotransformation of low-molecular-weight alcohols by Coleus forskohlii hairy root cultures 总被引:1,自引:0,他引:1
Coleus forskohlii hairy root cultures were shown to biotransform methanol and ethanol to the corresponding beta-D-glucopyranosides and beta-D-ribo-hex-3-ulopyranosides, and 2-propanol to its beta-D-glucopyranoside. 相似文献