Three neo-Clerodane Diterpenoids from Tinospora cordifolia Stems and Their Arginase Inhibitory Activities

Chem Pharm Bull (Tokyo). 2024;72(6):540-546. doi: 10.1248/cpb.c24-00240.

Abstract

Three neo-clerodane diterpenoids, including two new tinocordifoliols A (1) and B (2) and one known tinopanoid R (3), were isolated from the ethyl acetate-soluble fraction of the 70% ethanol extract of Tinospora cordifolia stems. The structures were elucidated by various spectroscopic methods, including one dimensional (1D) and 2D-NMR, high resolution-electrospray ionization (HR-ESI)-MS, and electronic circular dichroism (ECD) data. The T. cordifolia extract and all isolated compounds 1-3 possessed arginase I inhibitory activities. Among them, 3 exhibited moderate competitive inhibition of human arginase I (IC50 = 61.9 µM). Furthermore, docking studies revealed that the presence of a β-substituted furan in 3 may play a key role in the arginase I inhibitory activities.

Keywords: Tinospora cordifolia; arginase inhibitory activity; clerodane diterpenoid; neo-clerodane diterpenoid.

MeSH terms

  • Arginase* / antagonists & inhibitors
  • Arginase* / metabolism
  • Diterpenes, Clerodane* / chemistry
  • Diterpenes, Clerodane* / isolation & purification
  • Diterpenes, Clerodane* / pharmacology
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors* / chemistry
  • Enzyme Inhibitors* / isolation & purification
  • Enzyme Inhibitors* / pharmacology
  • Humans
  • Molecular Conformation
  • Molecular Docking Simulation*
  • Molecular Structure
  • Plant Stems* / chemistry
  • Structure-Activity Relationship
  • Tinospora* / chemistry

Substances

  • Arginase
  • Diterpenes, Clerodane
  • Enzyme Inhibitors