Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina

doi:10.1002/cjoc.202100586

CORC > 海洋研究所 > 中国科学院海洋研究所 > 实验海洋生物学重点实验室

	Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina
	Du, Feng-Yu 1,5,6; Mandi, Attila 4,5; Li, Xiao-Ming 1,3,6; Meng, Ling-Hong 1,3,6; Kurtan, Tibor 4,5; Wang, Bin-Gui 1,2,3,6
刊名	CHINESE JOURNAL OF CHEMISTRY
	2021-12-18
页码	7
关键词	Beauveria felina Natural products Destruxin hexadepsipeptides Structure elucidation Conformation analysis
ISSN号	1001-604X
DOI	10.1002/cjoc.202100586
通讯作者	Wang, Bin-Gui(wangbg@ms.qdio.ac.cn)
英文摘要	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.
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
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000731309500001
内容类型	期刊论文
源URL	[http://ir.qdio.ac.cn/handle/337002/177440]
专题	海洋研究所_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, Ctr Ocean Mega Sci, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China 3.Univ Chinese Acad Sci, Coll Marine Sci, Yuquan Rd 19A, Beijing 100049, Peoples R China 4.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary 5.Qingdao Agr Univ, Coll Chem & Pharm, Qingdao 266109, Shandong, Peoples R China 6.Chinese Acad Sci, Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China
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.