New Clerodane Diterpenoids from Tinospora Capillipes with Antibacterial and Anti-Inflammatory Properties

Chem Biodivers. 2024 Sep;21(9):e202401033. doi: 10.1002/cbdv.202401033. Epub 2024 Aug 19.

Abstract

Four new clerodane diterpenoids, namely tinocapills A-D (1-4), and one known analogue (5) were isolated from the roots of Tinospora capillipes in the present study. The structures of these new compounds, including their absolute configurations, were determined through a combination of detailed spectroscopic analysis and theoretical statistical approaches, including electronic circular dichroism (ECD) analyses and quantum mechanical (QM)-NMR methods. Additionally, the stereostructure of 5 was confirmed via X-ray diffraction analysis. Furthermore, all these isolates were evaluated for their antibacterial and anti-inflammatory activities. Compounds 1, 2 and 5 demonstrated antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) with MICs ranging from 4-64 μg/mL, and compounds 3 and 4 exhibited potential anti-inflammatory effects by suppressing LPS-induced TNF-α and NO releases in RAW264.7 cells.

Keywords: Anti-inflammatory; Antibacterial; Clerodane diterpenoid; TNF-α and NO production; Tinospora capillipes.

MeSH terms

  • Animals
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Anti-Inflammatory Agents* / chemistry
  • Anti-Inflammatory Agents* / isolation & purification
  • Anti-Inflammatory Agents* / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Diterpenes, Clerodane* / chemistry
  • Diterpenes, Clerodane* / isolation & purification
  • Diterpenes, Clerodane* / pharmacology
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Methicillin-Resistant Staphylococcus aureus* / drug effects
  • Mice
  • Microbial Sensitivity Tests*
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Nitric Oxide / metabolism
  • Plant Roots / chemistry
  • RAW 264.7 Cells
  • Tinospora* / chemistry
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Anti-Bacterial Agents
  • Diterpenes, Clerodane
  • Anti-Inflammatory Agents
  • Nitric Oxide
  • Tumor Necrosis Factor-alpha
  • Lipopolysaccharides
  • Anti-Inflammatory Agents, Non-Steroidal