Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog,asperpyrroindotide A,using LC–MS/MS-based molecular networking  

作　　者：Yi-Qian Han Qun Zhang Wei-Feng Xu Yang Hai Rong Chao Cui-Fang Wang Xue-Mei Hou Mei-Yan Wei Yu-Cheng Gu Chang-Yun Wang Chang-Lun Shao 

机构地区：[1]Key Laboratory of Marine Drugs,the Ministry of Education of China,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China [2]State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,Guilin 541004,China [3]College of Food Science and Engineering,Ocean University of China,Qingdao 266003,China [4]Syngenta Jealott’s Hill International Research Centre,Bracknell,Berkshire RG426EY,UK [5]Laboratory for Marine Drugs and Bioproducts,Qingdao National Laboratory for Marine Science and Technology,Qingdao 266237,China

出　　处：《Marine Life Science & Technology》2023年第1期85-93,共9页海洋生命科学与技术（英文）

基　　金：This work was supported by the Program of National Natural Science Foundation of China(Nos.41906090,81874300,42006092,U1706210,41776141 and 41322037);the Program of Natural Science Foundation of Shandong Province of China(Nos.JQ201510 and ZR2019BD047);Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education,Hainan Normal University(RDZH2021003);the Taishan Scholars Program,China(No.tsqn20161010).

摘　　要：Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides,namely,asperversiamides A–C(1–3)and asperheptatides A–D(4–7)and an unusual pyrroloindoline-containing new cycloheptapeptide,asperpyrroindotide A(8).The structure of 8 was elucidated by comprehensive spectroscopic data analysis,and its absolute configuration was determined by advanced Marfey’s method.The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized.Additionally,a series of new derivatives(10−19)of asperversiamide A(1)was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra.The preliminary structure−activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.

关 键 词：Marine natural product MS/MS-based molecular networking Cycloheptapeptides SEMI-SYNTHESIS Anti-tubercular activity 

分 类 号：Q178[生物学—水生生物学]