Статья

Emeridones A–F, a Series of 3,5-Demethylorsellinic Acid-Based Meroterpenoids with Rearranged Skeletons from an Endophytic Fungus <i>Emericella</i> sp. TJ29

Qin LiHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaChunmei ChenHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaCheng LiCollege of Pharmacy, Hubei University of Medicine, Shiyan 442000, ChinaMengsha WeiHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaChong DaiHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaYan HeTongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaJiaojiao GongHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaRunqi ZhuHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaXiao‐Nian LiState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, ChinaJunjun LiuHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaJianping WangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHucheng ZhuHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaYonghui ZhangHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

2019en

ABI

Аннотация

Six new 3,5-demethylorsellinic acid-based meroterpenoids, emeridones A–F (1–6), and eight known analogues (7–14) were isolated from Emericella sp. TJ29. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism calculations. Emeridone A (1) represents the first meroterpenoid featuring a unique rigid 6/6/5/6 tetracyclic carbon ring system with two additional lactone rings. Emeridones B and C (2 and 3) possess a 2,6-dioxabicyclo[2.2.1]heptane and a spiro[bicyclo[3.2.2]nonane-2,1′-cyclohexane] moiety, respectively, and both functionalities were found for the second time in meroterpenoids. These new compounds were evaluated for their cytotoxic activities against five human cancer cells, and compounds 2, 4, and 6 exhibited moderate cytotoxic activities, with IC50 values ranging from 8.19 to 18.80 μM.

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Идентификаторы

DOI: 10.1021/acs.joc.8b02830

Цитирования и источники

Цитирований: 2Использованных источников: 0

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