Identification of Corosolic and Oleanolic Acids as Molecules Antagonizing the Human RORγT Nuclear Receptor Using the Calculated Fingerprints of the Molecular Similarity

Int J Mol Sci. 2022 Feb 8;23(3):1906. doi: 10.3390/ijms23031906.

Abstract

RORγT is a protein product of the RORC gene belonging to the nuclear receptor subfamily of retinoic-acid-receptor-related orphan receptors (RORs). RORγT is preferentially expressed in Th17 lymphocytes and drives their differentiation from naive CD4+ cells and is involved in the regulation of the expression of numerous Th17-specific cytokines, such as IL-17. Because Th17 cells are implicated in the pathology of autoimmune diseases (e.g., psoriasis, inflammatory bowel disease, multiple sclerosis), RORγT, whose activity is regulated by ligands, has been recognized as a drug target in potential therapies against these diseases. The identification of such ligands is time-consuming and usually requires the screening of chemical libraries. Herein, using a Tanimoto similarity search, we found corosolic acid and other pentacyclic tritepenes in the library we previously screened as compounds highly similar to the RORγT inverse agonist ursolic acid. Furthermore, using gene reporter assays and Th17 lymphocytes, we distinguished compounds that exert stronger biological effects (ursolic, corosolic, and oleanolic acid) from those that are ineffective (asiatic and maslinic acids), providing evidence that such combinatorial methodology (in silico and experimental) might help wet screenings to achieve more accurate results, eliminating false negatives.

Keywords: RORC; RORgammaT; Th17; calculated fingerprints of the molecular similarity; corosolic acid; inverse agonist; oleanolic acid; tanimoto similarity.

MeSH terms

  • CD4-Positive T-Lymphocytes / cytology*
  • CD4-Positive T-Lymphocytes / drug effects
  • CD4-Positive T-Lymphocytes / metabolism
  • Cell Differentiation / drug effects
  • Cell Survival / drug effects
  • Cells, Cultured
  • Computer Simulation
  • Drug Evaluation, Preclinical
  • Drug Inverse Agonism
  • Humans
  • Interleukin-17 / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / agonists
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / chemistry*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology*
  • Peptide Mapping
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology
  • Th17 Cells / cytology*
  • Th17 Cells / drug effects
  • Th17 Cells / immunology
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • Interleukin-17
  • Nuclear Receptor Subfamily 1, Group F, Member 3
  • RORC protein, human
  • Small Molecule Libraries
  • Triterpenes
  • Oleanolic Acid
  • corosolic acid