Cardioprotective 22-hydroxylanostane triterpenoids from the fruiting bodies of Phellinus igniarius

Seven undescribed 22-hydroxylanostane triterpenoids were isolated from the fruiting bodies of Phellinus igniarius, together with three known sterols. Their structures were assigned by extensive spectroscopic and HRESIMS data analyses. The absolute configurations of C-22 were determined by X-ray crystallography, chemical methods, and spectroscopic data comparison. Phellinol G was a 25,26,27-trinorlanostane triterpenoid glycoside. 22S/22R25,26,27- Trinorlanosta-8-en-3 beta,22,24-triols with the same side chain as that of phellinol G were stereoselectively synthesized from commercial lanosterol for the first time. The key step involved Sharpless asymmetrical epoxidation. Phellinols A, B, and F showed cardioprotective activity against oxygen-glucose deprivation/reoxygenation injury in H9c2 cells at a concentration of 20 mu M.

Automated summary

Seven undescribed 22-hydroxylanostane triterpenoids were isolated from the fruiting bodies of Phellinus igniarius, with their structures determined by extensive spectroscopic and HRESIMS data analyses. Stereoselective synthesis of 22S/22R25,26,27-Trinorlanosta-8-en-3 beta,22,24-triols was achieved for the first time, with cardioprotective activity demonstrated by Phellinols A, B, and F.