Dimeric Acylphloroglucinol Derivatives with Anti-MRSA Activities from Chamelaucium uncinatum.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-05-05 DOI:10.1021/acs.jnatprod.5c00163

Qian Huang, Ni-Ping Li, Song Ang, Wei Huang, Jia-Qing Cao, Ji-Hong Gu, Lei Wang, Zhen-Long Wu, Wen-Cai Ye

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引用次数: 0

Abstract

Chamelauciumols A-I (1-9), nine undescribed dimeric acylphloroglucinol derivatives, were isolated from the aerial parts of Chamelaucium uncinatum. Structurally, compound 1 featured a new carbon skeleton characterized by an unprecedented prenyl-substituted methanodibenzo[b,f][1,5]dioxocin core. Compounds 2 and 3 represented new dimeric scaffolds, consisting of two methylated acylphloroglucinol derivatives linked via prenyl units. Compounds 4-9 were new phloroglucinol dimers with various linkage patterns. The structures and absolute configurations of these compounds were elucidated by comprehensive spectroscopic data, single-crystal X-ray diffraction analysis, and electronic circular dichroism calculation. Besides, the antibacterial activities against Gram-positive and Gram-negative bacterial strains of the isolates were evaluated. Compounds 3 and 4 exhibited potent inhibitory effects against methicillin-resistant Staphylococcus aureus with minimum inhibitory concentration values ranging from 0.5 to 1 μg/mL. A preliminary study on the mechanism of action revealed that compounds 3 and 4 exerted anti-MRSA effects through disrupting bacterial cell membrane integrity. Additionally, compounds 3 and 4 also demonstrated remarkable antibiofilm activities.

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具有抗mrsa活性的二聚酰基间苯三酚衍生物。

Chamelauciumols A-I（1-9）是9个未被描述的二聚酰基间苯三酚衍生物。在结构上，化合物1具有新的碳骨架，其特征是前所未有的戊酰取代的甲烷二苯并[b，f][1,5]二恶英核。化合物2和3是新的二聚体支架，由两个甲基化的酰基间苯三酚衍生物通过戊烯基单元连接而成。化合物4 ~ 9为新型间苯三酚二聚体，具有不同的连锁模式。通过综合光谱数据、单晶x射线衍射分析和电子圆二色性计算，对这些化合物的结构和绝对构型进行了分析。此外，对分离物对革兰氏阳性菌和革兰氏阴性菌的抑菌活性进行了评价。化合物3和4对耐甲氧西林金黄色葡萄球菌具有较强的抑制作用，最小抑制浓度为0.5 ~ 1 μg/mL。对其作用机制的初步研究表明，化合物3和4通过破坏细菌细胞膜完整性发挥抗mrsa作用。此外，化合物3和4也表现出显著的抗生物膜活性。

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.