{Reference Type}: Journal Article
{Title}: Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC-MS/MS-based molecular networking.
{Author}: Han YQ;Zhang Q;Xu WF;Hai Y;Chao R;Wang CF;Hou XM;Wei MY;Gu YC;Wang CY;Shao CL;
{Journal}: Mar Life Sci Technol
{Volume}: 5
{Issue}: 1
{Year}: 2023
{Factor}: 5
{DOI}: 10.1007/s42995-022-00157-8
{Abstract}: 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.