title: Lanesoic Acid: A Cytotoxic Zwitterion from Theonella sp.
abstract: Lanesoic acid (1) was isolated and characterized from Theonella sp. during PharmaMar's ongoing program to study cytotoxic substances from marine sources. Its planar structure, elucidated by spectral analysis (NMR, IR, UV, and MS), possesses an unusual skeleton containing a tetrahydropyrimidine cation that is stabilized as a zwitterion by an internal carboxylate counterion. The stereostructure of 1 was deduced from ROESY-NOESY, J-based configurational analysis (JBCA), and density functional theory (DFT) computational calculations fitted using the recently published DP4+ parameter. Compound 1 was moderately active and selective against pancreas PSN1 cells (IC50= 8.9 μg/mL) and inactive against colon HT-29, breast MD-MB-23, and NSCLC lung tumor cells.
authors: Departamento de Química Fundamental, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA) Rua As Carballeiras s/n, Universidade da Coruña , 15071 A Coruña, Spain.
authors: Jaime
authors: J
authors: Rodríguez
authors: Departamento de Química Fundamental, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA) Rua As Carballeiras s/n, Universidade da Coruña , 15071 A Coruña, Spain.
authors: Carlos
authors: C
authors: Jiménez
authors: Departamento de Química Fundamental, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA) Rua As Carballeiras s/n, Universidade da Coruña , 15071 A Coruña, Spain.
authors: María
authors: M
authors: Blanco
authors: Natural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte , Avda de los Reyes 1, 28770 Colmenar Viejo, Spain.
authors: Guillermo
authors: G
authors: Tarazona
authors: Natural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte , Avda de los Reyes 1, 28770 Colmenar Viejo, Spain.
authors: Rogelio
authors: R
authors: Fernández
authors: Natural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte , Avda de los Reyes 1, 28770 Colmenar Viejo, Spain.
authors: Carmen
authors: C
authors: Cuevas
mesh_terms: D000072283:A549 Cells; D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D011743:Pyrimidines / Q000302:isolation & purification* / Q000494:pharmacology; D047232:Theonella / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D011743:Pyrimidines