AI-Accelerated Structure Elucidation of Boavistamides A–C, Cyclic Depsipeptides from a Marine Filamentous Cyanobacterium Collected in Cabo Verde
Year: 2026
Type: preprint
Abstract: ABSTRACT Boavistamide A ( 1 ), a new alkyne-containing cyclic depsipeptide featuring the rare 3-amino-2-methyl-7-octynoic acid (AMOYA) moiety, was discovered along with two structurally related analogs, boavistamides B and C ( 2 and 3 ), from a filamentous marine cyanobacterium collected on Boa Vista Island, Cabo Verde. Their isolation was guided by antiplasmodial activity, GNPS MS/MS molecular networking, LC-MS profiling, and dereplication using the MarinLit database. The planar structures of boavistamides A–C ( 1 – 3 ) were elucidated through comprehensive HRMS and 1D/2D NMR analyses, with annotation support from AI-based tools SMART-NMR 2.1 and DeepSAT. The absolute configurations were established using Marfey’s analysis and L-Phe-OMe coupling, complemented by NMR-based conformational studies. Boavistamides A and B exhibited moderate antiplasmodial activity with no mammalian cell cytotoxicity. Microscopic observations and metagenomic binning identified the producer strain as belonging to the genus Okeania (Microcoleaceae). These results expand the chemical diversity of AMOYA-containing cyanobacterial metabolites and highlight the utility of integrated metabolomics and AI-assisted workflows for natural product discovery from environmental samples. GRAPHICAL ABSTRACT
Authors: Marine Cuau, Nicole E. Avalon, Byeol Ryu, Evgenia Glukhov, Jehad Almaliti, Adriana Rego, Thaiz R. Teixeira, Mai Shingyoji, Mariana L. De Souza, Alma Trinidad-Javier, Krittikorn Kumpornsin, Joseph Chen, Case W. McNamara, Conor R. Caffrey, Elizabeth A. Winzeler, Vitor M. Vasconcelos, Pedro N. Leão, William H. Gerwick
Language: English
Subfield: Pharmacology
Field: Medicine
Domain: Health Sciences
Open Access status: green
Awards: The catalytic core of the proteasome as a drug target to treat Human African Trypanosomiasis, A Genomic Approach to Discovering Novel Cathepsin Inhibitors from Cyanobacteria, University of California San Diego - to discover novel therapeutic for the treatment of patients with malaria in the low and middle income countries
OpenAlex ID: W7164896785