The discovery of an anti-inflammatory monoterpenoid, neoroseoside from the Zea mays

Bioorg Med Chem Lett. 2024 Jun 1:105:129737. doi: 10.1016/j.bmcl.2024.129737. Epub 2024 Apr 8.

Abstract

A new monoterpenoid, neoroseoside (1), along with two previously reported compounds, 2″-O-α-l-rhamnosyl-6-C-fucosylluteolin (2) and farobin A (3) were isolated from the Zea mays. The structure of compound 1 was determined through the analysis spectroscopic data, including mass spectrometry (MS), infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) data. The absolute configurations of 1 were deduced from the comparing the values of optical rotations and from the interpretation of electronic circular dichroism (ECD) spectra. Compounds 2 and 3 displayed moderate antibacterial activity against Streptococcus mutans ATCC 25175 (inhibition rates 24 % and 28 %, respectively) and Streptococcus sobrinus ATCC 33478 (inhibition rate of 26 %), at a concentration of 100 μg/mL, whereas compound 1 did not have any significant antibacterial activities. The compounds 1-3 also showed anti-inflammatory activity on cytokine IL-6 and TNF-α.

Keywords: Anti-inflammatory; ECD spectra; Monoterpenoid; Optical rotation; Zea mays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 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
  • Dose-Response Relationship, Drug
  • Drug Discovery
  • Interleukin-6 / antagonists & inhibitors
  • Interleukin-6 / metabolism
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Monoterpenes* / chemistry
  • Monoterpenes* / isolation & purification
  • Monoterpenes* / pharmacology
  • Streptococcus / drug effects
  • Streptococcus mutans / drug effects
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / metabolism
  • Zea mays* / chemistry

Substances

  • Anti-Bacterial Agents
  • Monoterpenes
  • Anti-Inflammatory Agents
  • Interleukin-6
  • Tumor Necrosis Factor-alpha