Highly oxygenated steroids with immunosuppressive activity from Solanum undatum
文献类型：期刊论文
| 作者 | Chen, Shu-Shuai1,2; Zheng, Cheng-Yu2; Yang, Guan-Zhou2; Zhou, Jun-Su2; He, Shi-Jun3; Fan, Yao-Yue1,2; Yue, Jian-Min1,2
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| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
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| 出版日期 | 2024-11-05 |
| 页码 | 7 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/d4ob01642d |
| 英文摘要 | Solanum undatum is a medicinal plant used for the treatment of oedema, rheumatoid arthritis and toothache, from which seven highly oxygenated steroids (1-7), including three new ones (1-3), have been characterized. Compound 1 is a new steroidal carboxylic acid featuring a cyclohexa-2,5-dien-1-one moiety and compounds 2 and 3 are new withanolide analogs with a 1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-ol terminus. Their structures and absolute configurations were determined by a combination of spectroscopic data, quantum chemical calculations, single-crystal X-ray diffraction, and the NMR-based phenylglycine methyl ester (PGME) method. An immunosuppressive activity assay revealed that compounds 2-7 exhibited substantial activities against the proliferation of T and B lymphocytes in vitro, with IC50 values ranging from 1.60 to 7.89 mu M and 0.90 to 6.90 mu M, respectively. Notably, compound 6 showed selective inhibitory effect toward B cells with the highest selective index (SI = 40.5). Preliminary structure-activity relationships of compounds 1-7 suggest that the terminal 1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-ol or 5,5-spiroacetal moiety is critical for immunosuppressive activity. Our study indicated that they could be promising lead compounds for immunosuppressive agents. |
| WOS关键词 | GLYCOSIDES ; FRUITS ; SAPONINS |
| 资助项目 | National Key Research and Development Program of China[2023YFE0206100] ; National Key Research and Development Program of China[22237007] ; National Key Research and Development Program of China[82122062] ; National Natural Science Foundation |
| WOS研究方向 | Chemistry |
| WOS记录号 | WOS:001350068700001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/314333]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | He, Shi-Jun; Fan, Yao-Yue; Yue, Jian-Min |
| 作者单位 | 1.Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Shandong, Peoples R China 2.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 3.Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Chen, Shu-Shuai,Zheng, Cheng-Yu,Yang, Guan-Zhou,et al. Highly oxygenated steroids with immunosuppressive activity from Solanum undatum[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2024:7. |
| APA | Chen, Shu-Shuai.,Zheng, Cheng-Yu.,Yang, Guan-Zhou.,Zhou, Jun-Su.,He, Shi-Jun.,...&Yue, Jian-Min.(2024).Highly oxygenated steroids with immunosuppressive activity from Solanum undatum.ORGANIC & BIOMOLECULAR CHEMISTRY,7. |
| MLA | Chen, Shu-Shuai,et al."Highly oxygenated steroids with immunosuppressive activity from Solanum undatum".ORGANIC & BIOMOLECULAR CHEMISTRY (2024):7. |
入库方式： OAI收割
来源：上海药物研究所
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