C28 steroids from the fruiting bodies of Ganoderma resinaceum with potential anti-inflammatory activity

Eight undescribed ergostane-type steroids, (22E,24R)-ergosta-7,22-dien-3 beta,5 alpha-diol- 6,5-olide, (22E,24R)-er-gosta-7,9(11),22-trien-3 beta,5 beta,6 beta-triol, (22E,24R)-6 beta-methoxy ergosta-7,9(11),22-trien-3 beta,5 alpha,14 beta-triol, (22E,24R)-9 alpha,15 alpha-dihydroxyergosta-4,6,8 (14),22-tetraen-3-one, (22E,24R)-ergosta-5,8,22-trien-3 beta,11 alpha-dihydroxyl-7-one, (22E,24R)-ergosta-4,7,22-trien-3 beta,9 alpha,14 beta-trihydroxy1-6-one, (22E,24R)-ergosta-7,22- dien-3 beta,9 alpha,14 beta-trihydroxy1-6-one, and (22E,24R)-6 beta-methoxyergosta-7,22-dien-3 beta, 5 alpha,9 alpha,14 beta-tetraol, and twentyone known analogues were isolated from the fruiting bodies of Ganoderma resinaceum Boud. Their chemical structures were determined on the basis of comprehensive spectroscopic analysis and X-ray crystal diffraction, as well as empirical pyridine-induced deshielding effects. Furthermore, selected compounds were evaluated for their inhibitory effects on macrophage activation using an inhibition of nitric oxide production assay. Finally, (22E,24R)-ergosta-5,8,22- trien-3/3,11 alpha-dihydroxy1-7-one, (22E,24R)-ergosta-4,7,22-trien-3 beta,9 alpha,14 beta-tri hydroxyl-6-one, (22E,24R)-6 beta-methoxyergosta-7,22-dien-3 beta,5 alpha,9 alpha,14 beta-tetrao1, (22E,24R)-ergosta-6,9,22-trien-3 beta,5 alpha,8 alpha-triol,ergost-6,22-dien-3 beta,5 alpha,8 alpha-triol, 5 alpha,6 alpha-epoxy-(22E,24R)-ergosta-8,22-diene-3 beta,7 alpha-diol, 5 alpha,6 alpha-epoxy-(22E,24R)- ergosta-8(14),22-diene-3 beta,7 alpha-diol, 5 alpha,6 alpha-epoxy-(22E,24R)-ergosta-8(14),22-diene-3 beta, 7 beta-diol, and 22E-7 alpha-methoxy-5 alpha,6 alpha-epoxyergosta-8(14),22-dien-3 beta-ol showed inhibitory effects on NO production with IC50 values ranging from 3.24 +/- 0.02 to 35.19 0.41 mu M compared with L-NMMA (IC50 49.86 +/- 2.13 mu M), indicating that they have potential anti-inflammatory activity.