Structurally diverse ent-clerodanoids from the aerial parts of Isodon scoparius

Phytochemistry. 2024 Dec:228:114229. doi: 10.1016/j.phytochem.2024.114229. Epub 2024 Aug 8.

Abstract

Scoparodane C (1), a diterpenoid with a rare 3,4-seco-3-nor-2,11-epoxy-ent-clerodane scaffold, was obtained from the aerial parts of Isodon scoparius, along with isocopariusines A-E (2-6), five ent-clerodanoids featuring a 5/6-fused ring system, and isocopariusines F-H (7-9), three common ent-clerodanoids. The structures of these previously undescribed compounds were established by a combination of spectroscopic analysis, X-ray diffraction, chemical derivatization, and quantum chemical calculation. Remarkably, isocopariusine B (3) showed strong resistance reversal activity against fluconazole-resistant Candida albicans.

Keywords: Chemical derivatization; Fluconazole-resistance reversal in Candida albicans; Isodon scoparius; Quantum chemical calculation; ent-Clerodanoids.

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Candida albicans* / drug effects
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology
  • Isodon* / chemistry
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Plant Components, Aerial* / chemistry

Substances

  • Antifungal Agents
  • Diterpenes, Clerodane