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51.
Evaluation of the Synthetic Potential of an AHBA Knockout Mutant of the Rifamycin Producer Amycolatopsis mediterranei 下载免费PDF全文
Ilona Bułyszko Dr. Gerald Dräger Anja Klenge Prof. Dr. Andreas Kirschning 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(52):19231-19242
Supplementing an AHBA(?) mutant strain of Amycolatopsis mediterranei, the rifamycin producer, with a series of benzoic acid derivatives yielded new tetraketides containing different phenyl groups. These mutasynthetic studies revealed unique reductive properties of A. mediterranei towards nitro‐ and azidoarenes, leading to the corresponding anilines. In selected cases, the yields of mutaproducts (fermentation products isolated after feeding bacteria with chemically prepared analogs of natural building blocks) obtained are in a range (up to 118 mg L?1) that renders them useful as chiral building blocks for further synthetic endeavors. The configuration of the stereogenic centers at C6 and C7 was determined to be 6R,7S for one representative tetraketide. Importantly, processing beyond the tetraketide stage is not always blocked when the formation of the bicyclic naphthalene precursor cannot occur. This was proven by formation of a bromo undecaketide, an observation that has implications regarding the evolutionary development of rifamycin biosynthesis. 相似文献
52.
Acyl‐Chain Elongation Drives Ketosynthase Substrate Selectivity in trans‐Acyltransferase Polyketide Synthases 下载免费PDF全文
Matthew Jenner Dr. José Pedro Afonso Hannah R. Bailey Sarah Frank Dr. Annette Kampa Prof. Dr. Jörn Piel Dr. Neil J. Oldham 《Angewandte Chemie (International ed. in English)》2015,54(6):1817-1821
Type I modular polyketide synthases (PKSs), which are responsible for the biosynthesis of many biologically active agents, possess a ketosynthase (KS) domain within each module to catalyze chain elongation. Acylation of the KS active site Cys residue is followed by transfer to malonyl‐ACP to yield an extended β‐ketoacyl chain (ACP=acyl carrier protein). To date, the precise contribution of KS selectivity in controlling product fidelity has been unclear. Six KS domains from trans‐acyltransferase (trans‐AT) PKSs were subjected to a mass spectrometry based elongation assay, and higher substrate selectivity was identified for the elongating step than in preceding acylation. A close correspondence between the observed KS selectivity and that predicted by phylogenetic analysis was seen. These findings provide insights into the mechanism of KS selectivity in this important group of PKSs, can serve as guidance for engineering, and show that targeted mutagenesis can be used to expand the repertoire of acceptable substrates. 相似文献
53.
Abeer Abas Abd El Aty Naglaa Salah El-Deen Mohamed Ibrahim Ahmed Saleh Ahmed Atef El-Beih Mohamed Helmy Abdelrazik Taha Abdelrahim Hussien Mahmoud Moustafa 《中国化学会会志》2020,67(4):652-657
Due to the rapidly increasing number of pathogenic bacteria, viruses, and tumor cells that possess resistance toward established therapies, lead structures for the development of new drugs are in high demand. The plant material of Tanacetum sinaicum is considered a prolific source of the potent biologically active sesquiterpene Tanacetolide A ( 1 ). In our research, we focused on the structural transformation of the substrate Tanacetolide A (compound 1 ) by suspended culture of the novel locally isolated terrestrial fungus Rhizopus oryzae KX685359. The fungal transformation resulted in the formation of 1β,3α-dihydroxy-6α-hydroperoxy-eudsm-4(15)-ene 12-oic acid ( 2 ) with higher antiproliferative activity against colon cancer cell line (Caco-2) than that of the parent compound ( 1 ). 相似文献
54.
Changsheng Wu Helga U. vanderHeul Alexey V. Melnik Jens Lübben Pieter C. Dorrestein Adriaan J. Minnaard Young Hae Choi Gilles P. vanWezel 《Angewandte Chemie (International ed. in English)》2019,58(9):2809-2814
The angucyclines form the largest family of polycyclic aromatic polyketides, and have been studied extensively. Herein, we report the discovery of lugdunomycin, an angucycline‐derived polyketide, produced by Streptomyces species QL37. Lugdunomycin has unique structural characteristics, including a heptacyclic ring system, a spiroatom, two all‐carbon stereocenters, and a benzaza‐[4,3,3]propellane motif. Considering the structural novelty, we propose that lugdunomycin represents a novel subclass of aromatic polyketides. Metabolomics, combined with MS‐based molecular networking analysis of Streptomyces sp. QL37, elucidated 24 other rearranged and non‐rearranged angucyclines, 11 of which were previously undescribed. A biosynthetic route for the lugdunomycin and limamycins is also proposed. This work demonstrates that revisiting well‐known compound families and their producer strains still is a promising approach for drug discovery. 相似文献
55.
Kalpani K. Somarathne Jordan A. J. McCone Amira Brackovic Jos Luis Pinedo Rivera J. Robin Fulton Euan Russell Jessica J. Field Christopher L. Orme Hedley L. Stirrat Jasmin Riesterer Paul H. Teesdale‐Spittle John H. Miller Joanne E. Harvey 《化学:亚洲杂志》2019,14(8):1230-1237
The fungal metabolite TAN‐2483B has a 2,6‐trans‐relationship across the pyran ring of its furo[3,4‐b]pyran‐5‐one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side‐chain analogues of TAN‐2483B. The synthesis relies on ring expansion of a reactive furan ring‐fused dibromocyclopropane and alkynylation of the resulting pyran. The furan ring is constructed by palladium‐catalysed carbonylative lactonisation. Various side‐chains are appended through Wittig‐type chemistry. The prepared analogues showed micromolar activity towards cancer cell lines HL‐60, 1A9 and MCF‐7 and certain human disease‐relevant kinases, including Bruton's tyrosine kinase (Btk). 相似文献
56.
近红外光谱技术的花生产毒霉菌侵染快速检测 总被引:1,自引:0,他引:1
为了能够快速、无损地评价花生的质量,确保储藏与食用安全,开发了一种基于近红外光谱技术的花生产毒霉菌污染程度的定性定量分析方法。首先对经过Co-60强辐射杀菌后的新鲜花生样品分别接种谷物中五种常见产毒霉菌(黄曲霉3.17、黄曲霉3.3950、寄生曲霉3.395、寄生曲霉3.0124、赭曲霉3.6486),并于适宜条件下(26 ℃、RH 80%)储藏9 d。其次,利用近红外光谱仪采集了不同时期花生样品在12 000~4 000 cm-1波段范围内的漫反射光谱,运用主成分分析(PCA)、判别分析(DA)和偏最小二乘回归(PLSR)建立了分析模型。结果显示,接种不同霉菌的样品随着储藏时间的延长均能得到有效区分,DA模型对储藏0,3,6与9 d花生的感染单一霉菌和多种霉菌的总体判别正确率分别达到100%和99.17%,PLSR模型对样品中的菌落总数的预测结果为:有效决定系数(R2P)为0.874 1、交互验证均方根误差(RMSECV)为0.276 Log CFU·g-1,剩余预测偏差(RPD)为1.92。结果表明,近红外光谱技术可以作为一种可靠的分析方法对花生受霉菌侵染的状况进行快速分析,从而确保贮藏期间花生的质量安全。 相似文献
57.
Yi Ren Ling-Hui Chao Jing Sun Xiao-Nan Chen Hui-Na Yao Zhi-Xiang Zhu 《Natural product research》2019,33(3):347-353
Two new polyketides, penicilloxalones A (1) and B (2), together with 13 known compounds (3–15), were isolated from the ethyl acetate extract of the solid substrate fermentation cultures of the fungus Penicillium oxalicum MHZ153. The structures of the isolates were determined by spectroscopic analysis and comparison of their spectroscopic and physicochemical data with the literature values. Compounds 7 and 11 showed inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC50 values of 0.9 ± 0.2 μM and 87.9 ± 0.7 μM, respectively. 相似文献
58.
Ahmed B.M. Ibrahim Amna S.A. Zidan Aref A.M. Aly Hanan K. Mosbah Ghada Abd-Elmonsef Mahmoud 《应用有机金属化学》2020,34(2):e5391
A cadmium complex of the general formula Cd(C13H9O2NCl)2(H2O)2 {C13H9O2NCl = 2-(4-chlorophenylamino)benzoate} was synthesized and characterized regarding its CHN data, solution molar conductivity and spectroscopic (UV–Vis. and IR) properties. Cadmium sulfide nanoparticles (CdS NPs) were grown form the microcrystalline complex and thiourea via a hydrothermal route. The as-prepared NPs were assigned based on X-ray powder diffraction (PXRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FE-SEM) and Brunauer – Emmett – Teller (BET) surface area measurements. The CdS absorption and emission spectra were also recorded that revealed an energy gap of 2.47 eV and large Stokes shift of 130 nm. For the as-prepared NPs, the measurements have also indicated a mesoporous structure and an average particle size of 20–28 nm associated with an average pore diameter of 11.21 nm. The as-synthesized CdS NPs acted as antifungal controlling agent against human and plant pathogenic fungi of serious environmental and health concerns. The NPs at concentration of 200 ppm inhibited several fungi with inhibition efficiency of 100% against Aspergillus ustus Au-28. The nanoparticles induced morphological abnormalities in fungal mycelia, conidia and vesicle. Additionally, they inhibited the conidia septum formation, accelerated the chlamydospores generation and enlarged the yeast cells. 相似文献
59.
AbstractPholiotone A (1), a new polyketide derivative, with tetrahydrobenzofuran-4(2H)-one skeleton, together with four known compounds, trichodermatides A (2) and B (3) and koninginins B (4) and E (5), were isolated from the crude extract of Pholiota sp. The structures of all the isolated compounds were determined mainly by NMR experiments, the modified Mosher method and electronic circular dichroism (ECD) calculations. The antifungal and cytotoxicity of all isolates were evaluated. 相似文献
60.
Juliana Feijó de Souza Daniel Adriano Vinícius Scalco Roberto Molina de Souza Fernanda Maria Marins Ocampos Andersson Barison Luis Francisco Angeli Alves 《Natural product research》2019,33(20):3033-3036
Alphitobius diaperinus is an important pathogen with worldwide distribution that causes severe economic loss of efficiency in broilers. This study evaluates the potential of organic extracts of two strains entomopathogenic fungus Beauveria bassiana (CG71 and UNI40) as a biocontrol agent on A. diaperinus and promotes the phytochemical investigation. The effective percentages of mortalities were 95.97% (UNI40 methanolic extract), 69.23, 64.64, and 50.39% (CG 71 methanolic, ethyl acetate and butanol extracts). However, there was a decrease in the lesser mealworms susceptibility in relation to the use of insecticides and extracts. The metabolites 5-hydroxymethyl-2-furanoic acid, dipicolinic acid and monomethyl dipicolinate were isolated from ethyl acetate extract, and β-adenosine of butanolic extract of B. bassiana CG 71. In addition, the cyclodepsipeptides were identified in methanolic extracts of the two strains. The insecticide activity results indicated that the B. bassiana extracts are an alternative to A. diaperinus control.