Ergostane-Type Steroids from Korean Wild MushroomXerula furfuraceathat Control Adipocyte and Osteoblast Differentiation

Abstract

As part of our current work to discover structurally and/or biologically novel compounds from Korean wild mushrooms, we isolated five ergostane-type steroids (1-5) from the fruiting bodies of Xerula furfuracea via repeated column chromatographic separations and HPLC purification. The chemical structures of the isolated steroids were shown to be (22E,24R)-24-methylcholesta-4,22diene-3,6-dione (1), ergosta-7,22-diene-3β,5α,6β-triol (2), ergosta-7,22-diene-3β,5α,6β,9α-tetraol (3), (22E,24R)-5α,8α-epidioxyergosta-6,22-diene-3β-ol-3-O-β-D-glucopyranoside (4), and (22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (5) based on comparison of the data regarding their spectroscopic and physical properties with those of previous studies. Notably, this is the first report on the presence of the identified steroids (1-5) in this mushroom. We tested compounds 1-5 to determine their effects on adipogenesis and osteogenesis in the mouse mesenchymal stem cell line C3H10T1/2 and found that compounds 4 and 5 suppressed the differentiation of stem cells into adipocytes. Notably, in addition to its suppressive effect on adipogenesis, compound 5 was also shown to promote the osteogenic differentiation of stem cells. These findings demonstrate that the bioactive compounds isolated might be effective for the treatment of menopause-associated syndromes, such as osteoporosis and obesity, as the isolated compounds were shown to suppress adipogenesis and/or promote osteogenesis of stem cells.

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

“…Kim et al isolated glucosides 21b and 22b from the Korean wild fungus Xerula furfuracea and tested their effects on adipogenesis and osteogenesis in a mouse mesenchymal stem cell line [ 10 ]. Both compounds were found to inhibit the differentiation of stem cells into adipocytes, which is of interest in the treatment of syndromes associated with menopause.…”

“…The latter is the main sterol of fungi involved in the regulation of membrane fluidity and structure as well as performing immunological functions [ 4 ]. Fungal ergosterol derivatives are often referred to as “ergostane-type steroids” [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ] or “ergosteroids” [ 13 , 14 , 15 , 16 , 17 ]. One should bear in mind, however, that the application of the term “ergosteroids” can be confusing, as it was also suggested by Lardy et al [ 18 ] to structurally different dehydroepiandrosterone derivatives based on their mode of action (influence on energy metabolism).…”