| Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi | |
| Tang, Ying1; Xue, Yongbo2; Du, Guang1; Wang, Jianping2; Liu, Junjun2; Sun, Bin2; Li, Xiao-Nian3; Yao, Guangmin2; Luo, Zengwei2; Zhang, Yonghui2 | |
| 2016-03-14 | |
| 发表期刊 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 卷号 | 55期号:12页码:4069-4073 |
| 摘要 | The reisolation and structural revision of brassiciceneD is described, and inspired us to reassign the core skeletons of brassicicenes C-H, J and K, ranging from dicyclopenta[a,d]cyclooctane to tricyclo[9.2.1.0(3,7)]tetradecane using quantum-chemical predictions and experimental validation strategies. Three novel, highly modified fusicoccanes, brassicicenesL-N, were also isolated from the fungus Alternaria brassicicola, and their structures were unequivocally established by spectroscopic data, ECD calculations, and crystallography. The reassigned structures represent the first class of bridgehead double-bond-containing natural products with a bicyclo[6.2.1]undecane carbon skeleton. Furthermore, their stabilities were first predicted with olefin strain energy calculations. Collectively, these findings extend our view of the application of computational predictions and biosynthetic logic-based structure elucidation to address problems related to the structure and stability of natural products. |
| 关键词 | Computational Chemistry Natural Products Nmr Spectroscopy Structure Elucidation Terpenoids |
| DOI | 10.1002/anie.201600313 |
| 收录类别 | SCI ; IC |
| 语种 | 英语 |
| WOS记录号 | WOS:000372660400038 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/26192 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.Huazhong Univ Sci & Technol, Tongji Hosp, Tongji Med Coll, Wuhan 430074, Peoples R China 2.Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China 3.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming, Peoples R China |
| 推荐引用方式 GB/T 7714 | Tang, Ying,Xue, Yongbo,Du, Guang,et al. Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(12):4069-4073. |
| APA | Tang, Ying.,Xue, Yongbo.,Du, Guang.,Wang, Jianping.,Liu, Junjun.,...&Zhang, Yonghui.(2016).Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,55(12),4069-4073. |
| MLA | Tang, Ying,et al."Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.12(2016):4069-4073. |
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