Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis
文献类型：期刊论文
| 作者 | Sun, Dong-Yu2,3; Han, Guan-Ying1,3; Yang, Na-Na2; Lan, Le-Fu2 ; Li, Xu-Wen2; Guo, Yue-Wei2,4
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| 刊名 | ORGANIC CHEMISTRY FRONTIERS
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| 出版日期 | 2018-03-21 |
| 卷号 | 5期号:6页码:1022-1027 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/c7qo01091e |
| 文献子类 | Article |
| 英文摘要 | Two rare new furan butanolides, namely sponalisolides A (1) and B (2), characterized by an unprecedented furan-bearing trinorsesquiterpene alkyl chain connecting either a butanolide (1) or an N-acyl homoserine lactone moiety (2), were isolated in racemic forms from the Beihai sponge Spongia officinalis, and were further separated, by chiral-phase HPLC, to their corresponding enantiomers 1a/1b and 2a/2b, respectively. The structures, including the absolute stereochemistry, of the two pairs of enantiomeric compounds, were unambiguously established by extensive spectroscopic analysis and biomimetic total synthesis, involving a key Johnson-Claisen rearrangement and a lactone cyclization after epoxidation or dihydroxylation. All the new compounds exhibited the Pseudomonas aeruginosa quorum sensing inhibitory activity. |
| WOS关键词 | SOUTH CHINA SEA ; AXINYSSA-VARIABILIS ; FURANOTERPENOIDS ; SESQUITERPENES ; CYCLIZATIONS ; DITERPENES ; NUDIBRANCH ; TERPENOIDS ; LASA |
| 资助项目 | Natural Science Foundation of China[81520108028] ; Natural Science Foundation of China[41476063] ; Natural Science Foundation of China[41676073] ; NSFC-Shandong Joint Fund for Marine Science Research Centers[U1606403] ; STCSM Project[15431901000] ; SKLDR/SIMM Project[SIMM 1705ZZ-01] ; "Youth Innovation Promotion Association" from the Chinese Academy of Sciences[2016258] ; "Young Elite Scientists Sponsorship" from the China Association for Science and Technology[2016QNRC001] ; Shanghai "Pujiang Program"[16PJ1410600] ; SA-SIBS Scholarship Program[00000000] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000428091500020 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279844]  |
| 专题 | 天然药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Li, Xu-Wen; Guo, Yue-Wei |
| 作者单位 | 1.Jinzhou Med Univ, Affiliated Hosp 1, 2 Ren Min Rd, Jinzhou 121001, Peoples R China; 2.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 555 Chong Zhi Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China; 3.Jinzhou Med Univ, Sch Pharmaceut Sci, Jinzhou 121001, Peoples R China; 4.Qingdao Natl Lab Marine Sci & Technol, Open Studio Druggabil Res Marine Lead Cpds, 1 Wenhai Rd, Qingdao 266237, Shandong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Sun, Dong-Yu,Han, Guan-Ying,Yang, Na-Na,et al. Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis[J]. ORGANIC CHEMISTRY FRONTIERS,2018,5(6):1022-1027. |
| APA | Sun, Dong-Yu,Han, Guan-Ying,Yang, Na-Na,Lan, Le-Fu,Li, Xu-Wen,&Guo, Yue-Wei.(2018).Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis.ORGANIC CHEMISTRY FRONTIERS,5(6),1022-1027. |
| MLA | Sun, Dong-Yu,et al."Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis".ORGANIC CHEMISTRY FRONTIERS 5.6(2018):1022-1027. |
入库方式： OAI收割
来源：上海药物研究所
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