Chemical investigation of Beauveria felina,a marine-derived entomopathogenic fungus,obtained two new destruxin hexadepsipep-tides(1 and 2)containing an L-Ala5 residue instead of the usual N-Me-L-Ala5.Interestingly,the presence of the L-Ala5 residue enabled two slowly-exchanging solution conformers with cis/trans(ILE3)-(N-Me-Val4)amide bond for 1 and 2 with 1.5∶1 and 1∶1 cis/trans ra-tios,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、Struc-tural(conformational)parameter-activity correlations suggested that the extended destruxin geometry with the preferred cis(ILE3)-(N-Me-Val4)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 bio-active destruxin agents with lower toxicity.

Feng-Yu Du;Attila Mándi;Xiao-Ming Li;Ling-Hong Meng;Tibor Kurtán;Bin-Gui Wang

CAS&Shandong Province Key Laboratory of Experimental Marine Biology,Institute of Oceanology,Chinese Academy of Sciences,and Laboratory of Marine Biology and Biotechnology,Qingdao National Laboratory for Marine Science and Technology,Nanhai Road 7,Qingdao,Shandong 266071,China;College of Chemistry and Pharmacy,Qingdao Agricultural University,Qingdao,Shandong 266109,China;Department of Organic Chemistry,University of Debrecen,POB 400,4002 Debrecen,Hungary;College of Marine Science,University of Chinese Academy of Sciences,Yuquan Road 19A,Beijing 100049,China;Center for Ocean Mega-Science,Chinese Academy of Sciences,Nanhai Road 7,Qingdao,Shandong 266071,China

中国化学（英文版）

[1]Feng-Yu Du;Attila Mándi;Xiao-Ming Li;Ling-Hong Meng;Tibor Kurtán;Bin-Gui Wang-.Experimental and Computational Analysis of the Solution and Solid-State Conformations of Hexadepsipeptides from Beauveria felina)[J].中国化学（英文版）,2022(03):378-384

Conformations,Hexadepsipeptides,felina,destruxin,hexadepsipep,Ala5,ILE3,Val4,Struc

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