Mass spectrometry-guided isolation of thiodiketopiperazines from an EtOAc-extract of Setosphaeria rostrata culture medium and their anti-skin aging effects on TNF-α-induced human dermal fibroblasts

IF 2.1 4区医学 Q3 BIOTECHNOLOGY & APPLIED MICROBIOLOGY

Journal of Antibiotics Pub Date : 2024-01-19 DOI:10.1038/s41429-023-00702-2

Haeun Kwon, Hee Woon Ann, Sojung Park, Jaeyoung Kwon, Keunwan Park, Seung Mok Ryu, Yuanqiang Guo, Jae-Jin Kim, Joung Han Yim, Il-Chan Kim, Sang Hee Shim, Sullim Lee, Dongho Lee

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Abstract

Using mass spectrometry (MS)-guided isolation methods, a new thiodiketopiperazine derivative (1) and exserohilone (2) were isolated from an EtOAc-extract of Setosphaeria rostrata culture medium. The chemical structure of the new compound was elucidated by MS and NMR spectroscopy, and the absolute configurations were established by the quantum mechanical calculations of electronic circular dichroism. All isolated compounds were examined for their effects on reactive oxygen species (ROS) production, matrix metalloproteinase 1 (MMP-1) secretion, and procollagen type I α1 secretion in tumor necrosis factor (TNF)-α-induced human dermal fibroblasts. Compound 1 and exserohilone (2) exhibited the inhibition of TNF-α-induced ROS generation and MMP-1 secretion. Additionally, compound 1 and exserohilone (2) increased the procollagen type I α1 secretion. Compound 1 docked computationally into the active site of MMP-1 (−6.0 kcal/mol).

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在质谱法指导下从 Setosphaeria rostrata 培养基的乙酸乙酯提取物中分离硫代二酮哌嗪及其对 TNF-α 诱导的人真皮成纤维细胞的抗皮肤老化作用

利用质谱（MS）引导的分离方法，从Setosphaeria rostrata培养基的乙酸乙酯提取物中分离出了一种新的硫代二酮哌嗪衍生物（1）和exserohilone（2）。通过质谱和核磁共振光谱阐明了新化合物的化学结构，并通过电子圆二色性量子力学计算确定了其绝对构型。研究了所有分离化合物对肿瘤坏死因子（TNF）-α诱导的人真皮成纤维细胞中活性氧（ROS）产生、基质金属蛋白酶 1（MMP-1）分泌和 I 型胶原蛋白 α1 分泌的影响。化合物 1 和 exserohilone (2) 具有抑制 TNF-α 诱导的 ROS 生成和 MMP-1 分泌的作用。此外，化合物 1 和 exserohilone (2) 还能增加 I 型胶原蛋白 α1 的分泌。化合物 1 通过计算与 MMP-1 的活性位点对接（-6.0 kcal/mol）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Antibiotics 医学-免疫学

CiteScore

6.60

自引率

3.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Antibiotics seeks to promote research on antibiotics and related types of biologically active substances and publishes Articles, Review Articles, Brief Communication, Correspondence and other specially commissioned reports. The Journal of Antibiotics accepts papers on biochemical, chemical, microbiological and pharmacological studies. However, studies regarding human therapy do not fall under the journal’s scope. Contributions regarding recently discovered antibiotics and biologically active microbial products are particularly encouraged. Topics of particular interest within the journal''s scope include, but are not limited to, those listed below: Discovery of new antibiotics and related types of biologically active substances Production, isolation, characterization, structural elucidation, chemical synthesis and derivatization, biological activities, mechanisms of action, and structure-activity relationships of antibiotics and related types of biologically active substances Biosynthesis, bioconversion, taxonomy and genetic studies on producing microorganisms, as well as improvement of production of antibiotics and related types of biologically active substances Novel physical, chemical, biochemical, microbiological or pharmacological methods for detection, assay, determination, structural elucidation and evaluation of antibiotics and related types of biologically active substances Newly found properties, mechanisms of action and resistance-development of antibiotics and related types of biologically active substances.