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  4. 新药研究国家重点实验室
Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired total synthesis and antitumor immunity

文献类型：期刊论文

作者Zheng, Cheng-Yu2,4; Zhao, Jin-Xin4; Yuan, Chang-Hao1,2,4; Peng, Xia4; Geng, Meiyu1,2,4; Ai, Jing2,4; Fan, Yao-Yue2,4; Yue, Jian-Min2,3,4
刊名CHEMICAL SCIENCE
出版日期2023-11-06
页码9
ISSN号2041-6520
DOI10.1039/d3sc04238c
通讯作者Ai, Jing(jai@simm.ac.cn) ; Fan, Yao-Yue(s040500290@126.com) ; Yue, Jian-Min(jmyue@simm.ac.cn)
英文摘要Sesterterpenoids are a very rare class of important natural products. Three new skeletal spiro sesterterpenoids, named orientanoids A-C (1-3), were isolated from Hedyosmum orientale. Their structures were determined by a combination of spectroscopic data, X-ray crystallography, and total synthesis. To obtain adequate materials for biological research, the bioinspired total syntheses of 1-3 were effectively achieved in 7-8 steps in overall yields of 2.3-6.4% from the commercially available santonin without using any protecting groups. In addition, this work also revised the stereochemistry of hedyosumins B (6) and C (10) as 11R-configuration. Tumor-associated macrophages (TAMs) have emerged as important therapeutic targets in cancer therapy. The in-depth biological evaluation revealed that these sesterterpenoids antagonized the protumoral and immunosuppressive functional phenotype of macrophages in vitro. Among them, the most potent and major compound 1 inhibited protumoral M2-like macrophages and activated cytotoxic CD8+ T cells, and consequently inhibited tumor growth in vivo. We report a holistic study of the isolation, structure elucidation, total syntheses, and biological evaluation of three unprecedented sesterterpenoids, orientanoids A-C (1-3).
WOS关键词STRUCTURAL ELUCIDATION ; DIELS
资助项目This work was financially supported by the National Natural Science Foundation (22237007, 81821005, and 82122062) of the Peopleapos;s Republic of China, the CAMS Innovation Fund for Medical Sciences (2019-I2M-5-080), the CAS Biological Resources Program ([22237007] ; This work was financially supported by the National Natural Science Foundation (22237007, 81821005, and 82122062) of the Peopleapos;s Republic of China, the CAMS Innovation Fund for Medical Sciences (2019-I2M-5-080), the CAS Biological Resources Program ([81821005] ; This work was financially supported by the National Natural Science Foundation (22237007, 81821005, and 82122062) of the Peopleapos;s Republic of China, the CAMS Innovation Fund for Medical Sciences (2019-I2M-5-080), the CAS Biological Resources Program ([82122062] ; National Natural Science Foundation[2019-I2M-5-080] ; CAMS Innovation Fund for Medical Sciences[KFJ-BRP-008] ; CAS Biological Resources Program[2020CXJQ02] ; Collaborative Innovation Cluster Project of Shanghai Municipal Commission of Health and Family Planning ; Shanghai Municipal Science and Technology Major Project
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001102198300001
出版者ROYAL SOC CHEMISTRY
源URL[http://119.78.100.183/handle/2S10ELR8/307863]  
专题新药研究国家重点实验室
通讯作者Ai, Jing; Fan, Yao-Yue; Yue, Jian-Min
作者单位1.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
2.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
3.Chinese Acad Med Sci, Res Units Discovery New Drug Lead Mol, Shanghai 201203, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Zheng, Cheng-Yu,Zhao, Jin-Xin,Yuan, Chang-Hao,et al. Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired total synthesis and antitumor immunity[J]. CHEMICAL SCIENCE,2023:9.
APA Zheng, Cheng-Yu.,Zhao, Jin-Xin.,Yuan, Chang-Hao.,Peng, Xia.,Geng, Meiyu.,...&Yue, Jian-Min.(2023).Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired total synthesis and antitumor immunity.CHEMICAL SCIENCE,9.
MLA Zheng, Cheng-Yu,et al."Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired total synthesis and antitumor immunity".CHEMICAL SCIENCE (2023):9.

入库方式： OAI收割

来源：上海药物研究所

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