Thrysaxinones A–F: antibacterial phloroglucinol-terpenoid adducts from Thryptomene saxicola†

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI:10.1039/d5qo00172b

Wei-Fang Su , Ni-Ping Li , Rui-Qin Cui , Fen Liu , Mu Chen , Xin-Yue Wu , Min-Jing Cheng , Jia-Qing Cao , Wei Huang , Xiao-Qi Zhang , Wen-Cai Ye , Lei Wang

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Abstract

Thrysaxinones A–F (), six new phloroglucinol-terpenoid adducts (PTAs), were isolated from Thryptomene saxicola. Their structures and absolute configurations were elucidated by extensive spectroscopic analysis, X-ray crystallography, and quantum chemical calculations. Compounds represent unprecedented PTAs with gorgonane- or oplopane-type sesquiterpenoid moieties. Notably, compound features an unusual 11-oxa-tricyclo[6.2.1.0^4,9]undecane core. Compound is a unique PTA with a new carbon skeleton formed by an acylphloroglucinol unit coupled with a bicyclogermacrene-type sesquiterpenoid moiety. The plausible biogenetic pathways for compounds were proposed. Moreover, compounds , , , and exhibited significant antibacterial activities against clinical methicillin-resistant Staphylococcus aureus (MRSA) strains. Compound , the most potent one, could rapidly and effectively eradicate bacteria by inducing hyperpolarization and disrupting cell membrane integrity.

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赤霉素A - F：从赤霉中提取的抗菌间苯三酚萜类加合物

从沙红花中分离到6个新的间苯三酚萜类加合物（PTAs）——Thrysaxinones A-F（1-6）。通过广泛的光谱分析、x射线晶体学和量子化学计算，阐明了它们的结构和绝对构型。化合物1-3分别代表了前所未有的含有柳柑烷型或邻戊烷型倍半萜类成分的PTAs。值得注意的是，化合物1具有不寻常的11-氧-三环[6.2.1.04,9]十一烷核。化合物4是一种独特的PTA，由酰基间苯三酚单元与双环烷型倍半萜部分偶联形成新的碳骨架。提出了化合物1 ~ 6可能的生物发生途径。此外，化合物1、2、5和6对临床耐甲氧西林金黄色葡萄球菌（MRSA）具有显著的抗菌活性。其中最有效的化合物1可以通过诱导超极化和破坏细胞膜完整性来快速有效地消灭细菌。

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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Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

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0.00%

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