COX-2 and iNOS inhibitory epimeric meroterpenoids from Ganoderma cochlear and structure revision of cochlearol Q

Fitoterapia. 2023 Jan:164:105390. doi: 10.1016/j.fitote.2022.105390. Epub 2022 Dec 10.

Abstract

Four novel epimeric meroterpenoids, ganadone A (1), 3',10'-di-epi-ganadone A (2), 10'-epi-ganadone A (3), and 3'-epi-ganadone A (4) as well as another pairs of epimers, ganadone B (5) and 10'-epi-ganadone B (6), with a same basic skeleton compound ganadone C (7), together with two lactonized meroterpenoids, ganadones D and E (8 and 9) were isolated from the fruiting bodies of Ganoderma cochlear. Compounds 1-7 were constructed with fascinating adjacent 6',7'-bifuran ring system. Fortunately, we have revised our previously reported structure cochlearol Q, which was proposed pyrano[6',7'-b]pyran ring system into 6',7'-bifuran motif. All the isolates were characterized by analysis of HRESIMS, NMR spectroscopy and 1 was supported by X-ray crystallography analysis. The absolute stereochemistry of 1-9 were assigned by quantum chemical calculations. Biological evaluation of 1-9 showed that 5, 6, and 9 have significant anti-inflammatory potentials.

Keywords: Anti-inflammatory activity; Epimers; Ganoderma cochlear; Meroterpenoids; Structure revision.

MeSH terms

  • Cyclooxygenase 2
  • Fruiting Bodies, Fungal / chemistry
  • Ganoderma* / chemistry
  • Molecular Structure
  • Terpenes* / chemistry

Substances

  • Terpenes
  • Cyclooxygenase 2