%0 Journal Article
%T Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC-MS/MS-based molecular networking.
%A Han YQ
%A Zhang Q
%A Xu WF
%A Hai Y
%A Chao R
%A Wang CF
%A Hou XM
%A Wei MY
%A Gu YC
%A Wang CY
%A Shao CL
%J Mar Life Sci Technol
%V 5
%N 1
%D 2023
%M 36713278
%F 5
%R 10.1007/s42995-022-00157-8
%X 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.
UNASSIGNED: The online version contains supplementary material available at 10.1007/s42995-022-00157-8.