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

Autor: 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
Rok vydání: 2023
Předmět:
Zdroj: Marine Life Science & Technology. 5:85-93
ISSN: 2662-1746
DOI: 10.1007/s42995-022-00157-8
Popis: 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.
Databáze: OpenAIRE