Fragment-Based Online OzESI-MS, NMR, and Computational DP4+/DFT Approaches to the Characterization of the Putative Biosynthetic Lipid Precursor of Atkamine from Alaskan Latrunculia Sponges

ACS Omega 2026 Open access

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Authors: Menny M. Benjamin, Cody F. Dickinson, Jared S. Wood, R. Thomas Williamson, George S. Hanna, Ahmed S. Alford, R. S. Stone, Gerald R. Hoff, Abhi R. Samala, Fayaj A. Mulani, Qibin Zhang, Mark T. Hamann
DOI: 10.1021/acsomega.5c11024
Cited by: 3
References: 55

Abstract

Abstract The extraction of Latrunculia sponges collected along the coast of the Aleutian Islands of Alaska yielded a lipid fraction, in which a natural long-chain monounsaturated aldehyde, (Z)-docos-15-enal (1), was isolated for the first time from this genus of sponge. Experimental, DP4+/DFT structure-probability calculations, and ab initio NMR chemical shift (CS) computational data comparing (Z)-docos-15-enal isolated from a natural sponge source with the previously reported synthetic material, confirmed the cis (Z) configuration of the double bond. Online ozonolysis LC-ESI-MS (OzESI) data validated the assignment of the C-15/C-16 olefin along the lipid chain. Aldehyde-based metabolites may serve as biosynthetic precursors for complex lipid alkaloids such as the atkamine pyrroloiminoquinone (PIQ).

Fields of Study & Subjects

Marine Sponges and Natural Products Seaweed-derived Bioactive Compounds Synthesis and Characterization of Pyrroles

Publication details

Journal / source
ACS Omega
Publisher
American Chemical Society (ACS)
Volume
11
Issue
9
Pages
14797–14805
Publication date
25 February 2026
Language
EN