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Bipoladien A, a Sesterterpenoid Containing an Undescribed 5/8/5/7 Carbon Skeleton from Bipolaris maydis
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-02-07 , DOI: 10.1021/acs.jafc.3c08134 Yong Shen 1 , Chunmei Chen 1 , Ziming Zhao 1 , Yu Liang 1 , Qin Li 1 , Xian Xia 2 , Peng Wu 3 , Feng He 3 , Qingyi Tong 1 , Hucheng Zhu 1 , Yonghui Zhang 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-02-07 , DOI: 10.1021/acs.jafc.3c08134 Yong Shen 1 , Chunmei Chen 1 , Ziming Zhao 1 , Yu Liang 1 , Qin Li 1 , Xian Xia 2 , Peng Wu 3 , Feng He 3 , Qingyi Tong 1 , Hucheng Zhu 1 , Yonghui Zhang 1
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Bipoladiens A–E (1–5), five new ophiobolin-derived sesterterpenoids, and a known compound 6 (bipolaricin R) were isolated from the cultures of the phytopathogenic fungus Bipolaris maydis. Their structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, HRESIMS, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analyses. Notably, compound 1 has an undescribed tetracyclic 5/8/5/7 fused carbon skeleton, and compound 2 possesses a rare multicyclic caged ring system. The biosynthetic pathway of 1 was proposed starting from 6 via a series of oxidation and cyclization reactions. Compound 6 showed excellent antiproliferation and apoptosis induction effects against A549 cell line. Additionally, compounds 5 and 6 exhibited noticeable antimicrobial ability against Bacillus cereus, Staphylococcus aureus, and Staphylococcus epidermidis. These findings not only developed the chemical and bioactivities diversities of ophiobolin-sesterterpenoid but also provided an idea to boost the application of natural products in the control of food pathogens.
中文翻译：
Bipoladien A，一种二萜类化合物，含有未描述的来自玉米双极菌的 5/8/5/7 碳骨架
Bipoladiens A–E ( 1–5 )、五种新的源自 ophiobolin 的二倍萜类化合物和一种已知的化合物6 （双极霉素 R）是从植物病原真菌玉米双极菌的培养物中分离出来的。基于综合光谱分析、HRESIMS、电子圆二色性（ECD）计算和单晶 X 射线衍射分析，阐明了它们的结构和绝对构型。值得注意的是，化合物1具有未描述的四环5/8/5/7稠合碳骨架，化合物2具有罕见的多环笼环系统。 1的生物合成途径被提出从6开始，通过一系列氧化和环化反应。化合物6对A549细胞系表现出优异的抗增殖和诱导凋亡作用。此外，化合物5和6对蜡样芽孢杆菌、金黄色葡萄球菌和表皮葡萄球菌表现出显着的抗菌能力。这些发现不仅开发了蛇草酚二倍萜化学和生物活性的多样性，而且为促进天然产物在食品病原体控制中的应用提供了思路。
更新日期：2024-02-07
中文翻译：
Bipoladien A，一种二萜类化合物，含有未描述的来自玉米双极菌的 5/8/5/7 碳骨架
Bipoladiens A–E ( 1–5 )、五种新的源自 ophiobolin 的二倍萜类化合物和一种已知的化合物6 （双极霉素 R）是从植物病原真菌玉米双极菌的培养物中分离出来的。基于综合光谱分析、HRESIMS、电子圆二色性（ECD）计算和单晶 X 射线衍射分析，阐明了它们的结构和绝对构型。值得注意的是，化合物1具有未描述的四环5/8/5/7稠合碳骨架，化合物2具有罕见的多环笼环系统。 1的生物合成途径被提出从6开始，通过一系列氧化和环化反应。化合物6对A549细胞系表现出优异的抗增殖和诱导凋亡作用。此外，化合物5和6对蜡样芽孢杆菌、金黄色葡萄球菌和表皮葡萄球菌表现出显着的抗菌能力。这些发现不仅开发了蛇草酚二倍萜化学和生物活性的多样性，而且为促进天然产物在食品病原体控制中的应用提供了思路。
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