Institutional Repository of Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences
| Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina | |
Du, Feng-Yu1,2,3; Mandi, Attila3,4; Li, Xiao-Ming1,2,5; Meng, Ling-Hong1,2,5 ; Kurtan, Tibor3,4; Wang, Bin-Gui1,2,5,6
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| 2021-12-18 | |
| 发表期刊 | CHINESE JOURNAL OF CHEMISTRY
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| ISSN | 1001-604X |
| 页码 | 7 |
| 通讯作者 | Wang, Bin-Gui(wangbg@ms.qdio.ac.cn) |
| 摘要 | Comprehensive Summary Chemical investigation of Beauveria felina, a marine-derived entomopathogenic fungus, obtained two new destruxin hexadepsipeptides (1 and 2) containing an L-Ala(5) residue instead of the usual N-Me-L-Ala(5). Interestingly, the presence of the L-Ala(5) residue enabled two slowly-exchanging solution conformers with cis/trans (ILE3)-(N-Me-Val(4)) amide bond for 1 and 2 with 1.5 : 1 and 1 : 1 cis/trans ratios, respectively, while only the conformer with cis amide bond was found in the solid-state. The solution and solid-state conformers were studied by NMR, X-ray diffraction and solution and solid-state ECD measurements, as well as by TDDFT-ECD calculations. Structural (conformational) parameter-activity correlations suggested that the extended destruxin geometry with the preferred cis (ILE3)-(N-Me-Val(4)) bond probably resulted in improved bioactivity and reduced toxicity for the destruxin class. This was the first report on the interconversion phenomenon of cis/trans amide bonds of destruxin class, which could give insights in the development of bioactive destruxin agents with lower toxicity. |
| 关键词 | Beauveria felina Natural products Destruxin hexadepsipeptides Structure elucidation Conformation analysis |
| DOI | 10.1002/cjoc.202100586 |
| 收录类别 | SCI |
| 语种 | 英语 |
| 资助项目 | National Natural Science Foundation of China[31270104] ; NSFC-Shandong Joint Fund for Marine Science Research Centers[U1606403] ; Oceanographic Data Center at IOCAS ; National Research, Development and Innovation Office[NKFI K120181] ; National Research, Development and Innovation Office[FK134653] ; Governmental Information- Technology Development Agency |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Multidisciplinary |
| WOS记录号 | WOS:000731309500001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.qdio.ac.cn/handle/337002/177441 |
| 专题 | 实验海洋生物学重点实验室 |
| 通讯作者 | Wang, Bin-Gui |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, CAS & Shandong Prov Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China 2.Chinese Acad Sci, Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China 3.Qingdao Agr Univ, Coll Chem & Pharm, Qingdao 266109, Shandong, Peoples R China 4.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary 5.Univ Chinese Acad Sci, Coll Marine Sci, Yuquan Rd 19A, Beijing 100049, Peoples R China 6.Chinese Acad Sci, Ctr Ocean Mega Sci, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China |
| 第一作者单位 | 中国科学院海洋研究所 |
| 通讯作者单位 | 中国科学院海洋研究所 |
| 推荐引用方式 GB/T 7714 | Du, Feng-Yu,Mandi, Attila,Li, Xiao-Ming,et al. Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina[J]. CHINESE JOURNAL OF CHEMISTRY,2021:7. |
| APA | Du, Feng-Yu,Mandi, Attila,Li, Xiao-Ming,Meng, Ling-Hong,Kurtan, Tibor,&Wang, Bin-Gui.(2021).Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina.CHINESE JOURNAL OF CHEMISTRY,7. |
| MLA | Du, Feng-Yu,et al."Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina".CHINESE JOURNAL OF CHEMISTRY (2021):7. |
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