Citation: Meijia Zheng, Yingjie Liu, Chunmei Chen, Qin Li, Xinran Zhang, Xiaotian Zhang, Weiguang Sun, Yonghui Zhang, Hucheng Zhu. Ophiobolin-type sesterterpenoids with unprecedented chemical architectures from Bipolaris oryzae and their inflammatory activity[J]. Chinese Chemical Letters, ;2025, 36(12): 110904. doi: 10.1016/j.cclet.2025.110904 shu

Ophiobolin-type sesterterpenoids with unprecedented chemical architectures from Bipolaris oryzae and their inflammatory activity

Meijia Zheng ^{, 1} ,
Yingjie Liu ^{, 1} ,
Chunmei Chen ^{, 1} ,
Qin Li ,
Xinran Zhang ,
Xiaotian Zhang ^{, *,} ,
Weiguang Sun ^{, *,} ,
Yonghui Zhang ^{, *,} ,
Hucheng Zhu ^{, *,}

.
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

2024520732@hust.edu.cn

weiguangsun@hust.edu.cn

zhangyh@mails.tjmu.edu.cn

zhuhucheng@hust.edu.cn

Received Date: 1 December 2024
Revised Date: 22 January 2025
Accepted Date: 27 January 2025
Available Online: 28 January 2025

Figures(4)

Bipolarpenoids A–J (1–10), ten undescribed ophiobolin-derived sesterterpenoids, were identified from the fungus Bipolaris oryzae. Their structures were elucidated by high resolution electrospray ionization mass spectrometry (HRESIMS), spectroscopic analyses, quantum chemical ¹³C nuclear magnetic resonance (NMR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analyses. Notably, compounds 1 and 2 were uniquely characterized by a multicyclic caged pentacyclo[8.4.0.0^1,5.0^4,9.0^7,11]tetradecane-bridged system; compounds 4–6 featured unprecedented 5/8/5/6 and 5/8/5/5 fused cores, respectively; compound 7 represented the first example of 3,4-seco-ophiobolin-alkaloid hybrid with a modified 5/6/8/5/5 fused carbon skeleton. Compound 9 showed potential anti-inflammatory effect in RAW264.7 macrophages and ulcerative colitis mice.
- Bipolaris oryzae,
- Ophiobolin-derived sesterterpenoids,
- Structure elucidation,
- Anti-inflammatory activities,
- Putative biosynthetic pathways
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