Six novel steroids from culture of basidiomycete Polyporus ellisii

Abstract

Investigation of the culture of basidiomycete Polyporus ellisii led to the isolation of a novel compound 3β,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (1) with a new 5/7/6/5 ring system of ergosterol skeleton. In addition, five new steroids, 5β,6β-epoxy-3β,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5β,6β-epoxy-3β,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 5α,6α-epoxy-3β,9α,15α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (4), 15α-acetoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), 15β-methoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), along with four known ergosterols (7-10), were obtained. All structures were elucidated based on 1D and 2D NMR spectral data. New compounds were evaluated for cytotoxicity against five human cancer cell lines, only compound 4 was found to exhibit a favorable cytotoxicity profile toward all tested tumor cell lines.

Lipid Metabolic Versatility in Malassezia spp. Yeasts Studied through Metabolic Modeling

“…These reactions were almost negligible in the other three species studied. Differences in the fungal steroid biosynthesis between M. furfur and the other three Malassezia species studied may be explained by (i) the production of steroid-like fungal hormones in M. furfur for sexual reproduction, as happens in ascomycetes ( Gooday, 1974 ); (ii) fungal steroids perhaps being a constitutive component of M. furfur , as is the case of the fruiting body of the basidiomycete Sarcodon joedes ( Liu et al, 2013 ); and most likely, (iii) steroids in M. furfur perhaps acting as secondary metabolites, as previously reported in the basidiomycete Polyporus ellisii ( Wang et al, 2012 ). Finally, the differences in arachidonic acid lipid metabolism found in the atypical M. furfur strain may be related to the presence of precursors of eicosanoids that may act as an alternative lipid compound in this strain ( Bajpai et al, 1991 ).…”

Two New Ergosterol Derivatives from the Basidiomycete Cortinarius glaucopus

“…Compounds 2 and 4 belong to a restricted group of fungal ergosta-6,8(14)-dien-15-one derivatives, [17] [24] and the finding in C. glaucopus represents, to the best of our knowledge, the first isolation of such compounds from terrestrial mushrooms. Interestingly, the cytostatic sterol 4 was first isolated from a spongederived fungus grown on a malt extract medium, [17] suggesting that marine-derived fungi and terrestrial fungi likely share the same steroid biosynthetic pathways.…”

“…2 as (23R*)-1A and (23R*)-1B, respectively, were largely predominant, together representing ˃ 95% of the entire rotamer population of (23R*)-1. It was characterized by dihedral angles of À179.7°between CH(22)-CH(23), 57.9°between CH(23)-CH (24), and 68.7°between CH(24)-CH(25) (Fig. It was characterized by dihedral angles of À179.7°between CH(22)-CH(23), 57.9°between CH(23)-CH (24), and 68.7°between CH(24)-CH(25) (Fig.…”

“…It was characterized by dihedral angles of À179.7°between CH(22)-CH(23), 57.9°between CH(23)-CH (24), and 68.7°between CH(24)-CH(25) (Fig. The dihedral angles in this conformer were equal to À79.1°between CH(22)-CH(23), 168.6°b etween CH(23)-CH (24), and 64.1°between CH(24)-CH(25) (Fig. On the other hand, the abundance of (23R*)-1B was 40% in gas phase and 33.2% in CHCl 3 .…”

Polyellisin, a novel polyketide from cultures of the basidiomycete Polyporus ellisii

“…At rst, a number of biologically active cerebrosides were isolated from its fruiting bodies. [2][3][4] Aer that, a number of ergosterols 5 and sesquiterpenoids 6 were obtained from cultures of this fungus in 2013. In our continuing search for structurally interesting and biologically active natural products from higher fungi, [5][6][7][8][9][10][11][12] an unprecedented polyketide, named polyellisin (1, Fig.…”