Aleutianamine B, A Novel Chiral Sulfoxide Isolated from Latrunculia spp. and Generated via Semi-Synthesis, Exhibits Selectivity for Ovarian Cancer Cells

We report a new optically active sulfoxide containing natural product isolated from an Alaskan Latrunculia spp. collection off the shores of the Aleutian Islands which we term aleutianamine B. It was identified and characterized in part via contemporary computational tools. Global Natural Products Social Molecular Networking (GNPS) analysis was a key tool used in identifying aleutianamine B in the crude extract. The relative configuration of the unique stereogenic sulfur atom was determined by DFT computational analysis. We also report the synthesis of aleutianamine B from aleutianamine. Aleutianamine B was evaluated against ovarian cancer and normal cell lines. This revealed that aleutianamine B retained submicromolar potency against A2780 cells while being ≥50-fold less potent on noncancerous cells; this was in stark contrast to the parent compound, aleutianamine, which displayed potent cytotoxicity against normal cell lines. Overall, the pyrroloiminoquinone (PIQ) class increasingly reveals unique selectivity and potency for tumor cell groups that are currently resistant to available chemotherapy, providing significant leads for therapeutics and biochemical probes.