Isoechinulin-Type Diketopiperazines with Anti-monocyte Adhesion Activities from a Sponge-Associated Aspergillus sp.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-24 DOI:10.1021/acs.jnatprod.5c00077

Weihao Chen, Jianheng Ma, Mengjing Cong, Xiaoyan Pang, Xiuping Lin, Shengrong Liao, Bin Yang, Xuefeng Zhou, Junfeng Wang, Yonghong Liu

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引用次数: 0

Abstract

Seven new isoechinulin-type diketopiperazines (DKPs), asperfatsines A-G (1-7), along with five known analogues (8-12), were isolated from cultures of a sponge-associated Aspergillus sp. SCSIO41034. The structural elucidations, including the determination of absolute configurations, were accomplished by comprehensive analyses utilizing NMR spectroscopy, HRESIMS, gas chromatography-mass spectrometry (GC-MS), Marfey's method, Mo₂(OAc)₄-induced circular dichroism, modified Mosher's method, and electronic circular dichroism (ECD) calculations. Asperfatsines A-C represent the first three cases of isoechinulin-type DKPs possessing three distinct long-chain fatty acid moieties. Pretreatment with 1, 3, 4, and 8 in tumor necrosis factor α (TNF-α)-stimulated human umbilical vein endothelial cells led to a reduction in the adhesion of THP-1 monocytes. Compound 4 downregulates the gene expression of cell adhesion molecules in a dose-dependent manner. These findings suggest that isoechinulin-type DKPs represent promising candidates with core molecular frameworks that may serve as a foundation for developing antivascular inflammation therapies.

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海绵相关曲霉菌抗单核细胞粘附活性的异青霉素型二酮哌嗪类。

从海绵相关曲霉sp. SCSIO41034的培养物中分离出7个新的异青霉素型双酮哌嗪（DKPs）， asperfatsines a - g(1-7)，以及5个已知的类似物（8-12）。通过核磁共振光谱、hremms、气相色谱-质谱（GC-MS）、Marfey法、Mo2(OAc)4诱导圆二色性、改进的Mosher法和电子圆二色性（ECD）计算等综合分析，完成了结构解析，包括绝对构型的确定。天冬氨酸A-C代表具有三个不同长链脂肪酸片段的异紫雏菊素型DKPs的前三种情况。用1、3、4和8预处理肿瘤坏死因子α (TNF-α)刺激的人脐静脉内皮细胞导致THP-1单核细胞粘附减少。化合物4以剂量依赖的方式下调细胞粘附分子的基因表达。这些发现表明，异紫皮苷型DKPs具有核心分子框架，可能作为开发抗血管炎症治疗的基础。

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 Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.