Structurally diverse phenylpropanoyl phloroglucinol derivatives from Mallotus philippensis and their anti-bacterial activities.

IF 4.5 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2024-12-01 Epub Date: 2024-10-28 DOI:10.1016/j.bioorg.2024.107918

Yeqi Chen, Wenlin Zheng, Xun Song, Dabo Pan, Yue Zhuo, Zhenzhen Yang, Qi Wang, Yan Wu, Jihong Gu

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Abstract

Fifteen undescribed phenylpropanoyl phloroglucinol derivatives featuring modified isoprenyl and/or geranyl units (1-15), in conjunction with thirteen known analogues (16-28), were obtained from the glandular hairs of the fruit of Mallotus philippensis. Meanwhile, fourteen pairs of new enantiomers [(±)-1-9, (±)-11-15] were further resolved by chiral purification. Their structures were determined by comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments and quantum chemical calculations. Bioactivity evaluation showed that compound 17 exhibited significant anti-bacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) with MIC of 6 μg/mL, while compounds 3, 4, 8 and 18 displayed moderate effects with MIC of 24, 12, 24, and 12 μg/mL, respectively. The KEGG enrichment analysis of 17 revealed that the phosphotransferase system (PTS) pathway was significantly enriched. In addition, compound 17 was found to affect the amino acids biosynthesis and amino acids/carbohydrate metabolism, and the qRT-PCR verified the accuracy of the transcriptome analysis.

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来自菲利蒲草的结构多样的苯基丙酰基氯葡萄糖醇衍生物及其抗菌活性。

从菲利蒲桃（Mallotus philippensis）果实的腺毛中获得了 15 种未曾描述过的苯基丙酰基氯代葡萄糖苷醇衍生物，这些衍生物具有经过修饰的异戊烯基和/或香叶基单元（1-15），以及 13 种已知的类似物（16-28）。同时，通过手性纯化进一步分离出了 14 对新的对映体 [(±)-1-9、(±)-11-15]。通过综合光谱分析、单晶 X 射线衍射实验和量子化学计算，确定了它们的结构。生物活性评价表明，化合物 17 对耐甲氧西林金黄色葡萄球菌（MRSA）具有显著的抗菌活性，MIC 为 6 μg/mL，而化合物 3、4、8 和 18 的抗菌效果一般，MIC 分别为 24、12、24 和 12 μg/mL。对 17 的 KEGG 富集分析表明，磷酸转移酶系统（PTS）途径被显著富集。此外，还发现化合物 17 影响氨基酸生物合成和氨基酸/碳水化合物代谢，qRT-PCR 验证了转录组分析的准确性。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.