Diterpenoids with Antibacterial Activities from the Fungus Trichoderma harzianum

J Agric Food Chem. 2024 Jul 10;72(27):15228-15236. doi: 10.1021/acs.jafc.4c00067. Epub 2024 Jun 27.

Abstract

A new fusicoccane diterpenoid, harziaderma A (1), two novel harziane diterpenoids, harzianones G and H (2 and 3), one revised harziane diterpenoid (4), and two known diterpenoids (5 and 6) were isolated from the fungus Trichoderma harzianum and established via NMR, HRESIMS, Mo2(OAc)4-induced circular dichroism (ICD) and electronic circular dichroism (ECD) calculations. It is worth noting that compound 1 represents the first instance of a fusicoccane-type diterpenoid derived from T. harzianum. The structure of furanharzianone B was revised to 4 via careful spectroscopic analyses. Additionally, compounds 2 and 5 could suppress the overall growth of the foodborne bacterial pathogen Bacillus cereus. Compound 4 showed a moderate suppressive impact on NO generation in lipopolysaccharide (LPS)-treated RAW 264.7 cells. The discoveries from the current study not only expanded the structural variety of diterpenoids isolated from T. harzianum but also laid a robust foundation for the development of harziane diterpenoids as anti-foodborne pathogen agents.

Keywords: ECD calculations; Trichoderma harzianum; biological activity; diterpenoids.

MeSH terms

  • Animals
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacillus cereus / drug effects
  • Diterpenes* / chemistry
  • Diterpenes* / pharmacology
  • Hypocreales / chemistry
  • Mice
  • Molecular Structure
  • RAW 264.7 Cells

Substances

  • Diterpenes
  • Anti-Bacterial Agents

Supplementary concepts

  • Trichoderma harzianum