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来自某菌株的色素菌素作为抗生物膜剂以及来自某菌株的一种新的糖基化asperfuran。

Pigmentosins from sp. as antibiofilm agents and a new glycosylated asperfuran from .

作者信息

Helaly Soleiman E, Kuephadungphan Wilawan, Phainuphong Patima, Ibrahim Mahmoud A A, Tasanathai Kanoksri, Mongkolsamrit Suchada, Luangsa-Ard Janet Jennifer, Phongpaichit Souwalak, Rukachaisirikul Vatcharin, Stadler Marc

机构信息

Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), Inhoffenstraße 7, 38124 Braunschweig, Germany.

Department of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt.

出版信息

Beilstein J Org Chem. 2019 Dec 16;15:2968-2981. doi: 10.3762/bjoc.15.293. eCollection 2019.

Abstract

In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A () and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (), were isolated from the spider-associated fungus sp. Furthermore, a new glycosylated asperfuran , together with one new () and two known ( and ) cyclodepsipeptides, was isolated from . The pigmentosins and showed to be active against biofilm formation of DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (), as well as the antimicrobial effect of pigmentosin A (), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming . The structure elucidation and determination of the absolute configuration were accomplished using a combination of spectroscopy, including 1D and 2D NMR, HRMS, Mosher ester analysis, and comparison of calculated/experimental ECD spectra. A chemotaxonomic investigation of the secondary metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC-DAD-MS) revealed that the production of pigmentosin B () was apparently specific for sp., while the glycoasperfuran was specific for .

摘要

在我们对泰国产的具有生物活性代谢产物的无脊椎动物致病真菌的探索过程中,从与蜘蛛相关的真菌 种中分离出了色素菌素A( )和一种新的双(萘并-α-吡喃酮)衍生物色素菌素B( )。此外,还从 中分离出了一种新的糖基化asperfuran ,以及一种新的( )和两种已知的( 和 )环缩肽。色素菌素A和B对嗜麦芽窄食单胞菌DSM1104的生物膜形成具有活性。色素菌素B( )对所研究的微生物和细胞系缺乏毒性,以及色素菌素A( )的抗菌作用,使其成为进一步开发用于涉及形成生物膜的嗜麦芽窄食单胞菌感染联合治疗的良好候选物。通过结合光谱学方法,包括一维和二维核磁共振、高分辨质谱、莫舍尔酯分析以及计算/实验电子圆二色光谱的比较,完成了结构解析和绝对构型的确定。使用配备二极管阵列检测和质谱的分析型高效液相色谱(HPLC-DAD-MS)对次生代谢产物谱进行的化学分类学研究表明,色素菌素B( )的产生显然是 种所特有的,而糖基化asperfuran 是 所特有的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b86/6941404/fc6ba56b577c/Beilstein_J_Org_Chem-15-2968-g002.jpg

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