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
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume55Issue:12Pages:4069-4073
AbstractThe 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.
KeywordComputational Chemistry Natural Products Nmr Spectroscopy Structure Elucidation Terpenoids
DOI10.1002/anie.201600313
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000372660400038
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/26192
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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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