Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica.,Beilstein Journal of Organic Chemistry

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Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2019-12-16 , DOI: 10.3762/bjoc.15.293
Soleiman E Helaly _{1,

2} , Wilawan Kuephadungphan _{1,

3} , Patima Phainuphong ₄ , Mahmoud A A Ibrahim ₅ , Kanoksri Tasanathai ₆ , Suchada Mongkolsamrit ₆ , Janet Jennifer Luangsa-Ard ₆ , Souwalak Phongpaichit ₃ , Vatcharin Rukachaisirikul ₇ , Marc Stadler ₁

Affiliation

In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming S. aureus. 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 (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica.

中文翻译：

来自 Gibellula sp. 的色素素。作为抗生物膜剂和来自爪哇虫草的新型糖基化阿哌呋喃。

在我们探索泰国无脊椎动物致病真菌的生物活性代谢物过程中，从与蜘蛛相关的真菌中分离出了色素A (1) 和一种新的双(萘并-α-吡喃酮) 衍生物色素B (2)吉贝鲁拉属此外，从爪哇冬虫夏草中分离出一种新的糖基化 asperfuran 3 以及一种新的 (6) 和两种已知的 (4 和 5) 环缩缩肽。色素蛋白 1 和 2 对金黄色葡萄球菌 DSM1104 生物膜的形成具有活性。色素蛋白 B (2) 对所研究的微生物和细胞系没有毒性，并且色素蛋白 A (1) 具有抗菌作用，这使得它们成为进一步开发用于涉及生物膜形成 S 的感染联合治疗的良好候选者。 .金黄色葡萄球菌。结构阐明和绝对构型的测定是通过结合光谱学来完成的，包括一维和二维核磁共振、高分辨质谱、莫舍酯分析以及计算/实验 ECD 光谱的比较。使用分析型 HPLC 结合二极管阵列检测和质谱 (HPLC-DAD-MS) 对次生代谢物谱进行的化学分类学研究表明，色素蛋白 B (2) 的产生显然是 Gibellula sp. 特异的，而 gluasperfuran 3 则是特异的对于爪哇咖啡。

更新日期：2019-12-17

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