Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti
- Shuyuan Mo
Shuyuan MoHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Shuyuan Mo
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- Yaxin Zhang
Yaxin ZhangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Yaxin Zhang
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- Rui Jiang
Rui JiangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Rui Jiang
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- Hanxiao Zeng
Hanxiao ZengHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Hanxiao Zeng
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- Zhihong Huang
Zhihong HuangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Zhihong Huang
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- Jie Yin
Jie YinHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Jie Yin
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- Sitian Zhang
Sitian ZhangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Sitian Zhang
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- Jun Yao
Jun YaoHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Jun Yao
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- Jianping Wang*
Jianping Wang*Email: [email protected]Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Jianping Wang
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- Zhengxi Hu*
Zhengxi Hu*Email: [email protected]Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Zhengxi Hu
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- Yonghui Zhang*
Yonghui Zhang*Email: [email protected]. Tel: 86-27-83692892. Fax: 86-27-83692762.Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People’s Republic of ChinaMore by Yonghui Zhang
Abstract
Guided by the Global Natural Products Social (GNPS) molecular networking strategy, five undescribed eremophilane-type sesquiterpenoid derivatives (1–5) were isolated and identified from fungus Penicillium roqueforti, which was separated from the root soil of plant Hypericum beanii collected in Shennongjia Forestry District, Hubei Province. Dipeniroqueforins A–B (1–2), representing a lactam-type sesquiterpenoid skeleton with a highly symmetrical and homodimeric 5/6/6–6/6/5 hexacyclic system, are reported within the eremophilane-type family for the first time. Peniroqueforin D (5) represents the first example of a 1,2-seco eremophilane-type sesquiterpenoid derivative featuring an undescribed 7/6-fused ring system. The structures of these compounds were elucidated by various spectroscopic analyses, DP4+ probability analyses, ECD calculations, and single-crystal X-ray diffraction experiments. Furthermore, these isolates were evaluated for cytotoxicity, and the result uncovered that compound 1 displayed broad-spectrum activity. Further mechanistic study revealed that compound 1 could significantly upregulate the mRNA expression of genes related to the oxidative induction, leading to the abnormal ROS levels in tumor cells and ultimately causing tumor cell apoptosis.
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