Lanesoic Acid: A Cytotoxic Zwitterion from Theonella sp

Org Lett. 2016 Nov 18;18(22):5832-5835. doi: 10.1021/acs.orglett.6b02832. Epub 2016 Nov 1.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • HT29 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Pyrimidines / isolation & purification*
  • Pyrimidines / pharmacology
  • Theonella / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Pyrimidines