Lanesoic Acid: A Cytotoxic Zwitterion from Theonella sp.

• DOI: 10.1021/acs.orglett.6b02832
• Publication Date: 2016-11-01T18:58:46Z
• Authors: Jaime Rodríguez; Carlos Jiménez; María Blanco; Guillermo Tarazona; Rogelio Fernández; Carmen Cuevas
• Keywords: Zwitterion

Lanesoic acid (1) was isolated and characterized from Theonella sp. during PharmaMar's ongoing program to study cytotoxic substances marine sources. Its planar structure, elucidated by spectral analysis (NMR, IR, UV, MS), possesses an unusual skeleton containing a tetrahydropyrimidine cation that is stabilized as zwitterion internal carboxylate counterion. The stereostructure of 1 deduced ROESY-NOESY, J-based configurational (JBCA), density functional theory (DFT) computational calculations fitted using the recently published DP4+ parameter. Compound moderately active selective against pancreas PSN1 cells (IC50 = 8.9 μg/mL) inactive colon HT-29, breast MD-MB-23, NSCLC lung tumor cells.