Pregnane-type steroids from the inedible mushroom Thelephora terrestris.
Chromatographic fractionation of the methanol extract of fruiting bodies of the inedible Japanese mushroom Thelephora terrestris (Thelephoraceae) has led to the isolation and characterization of two unusual new pregnane-type steroids, 2beta,3alpha-dihydroxypregna-4,7,16-trien-12,20-dione (2) and 1alpha,2beta,3alpha-trihydroxypregna-4,7,16-trien-12,20-dione (3) named terresterones A and B (2, 3), as well as the previously known compound stizophyllin, now assigned as 2beta,3alpha,12beta-trihydroxypregna-4,7,16-trien-20-one (1). Elucidation of their structures and the revision of the stereochemical assignment of stizophyllin were achieved by means of extensive 1D and 2D NMR, UV, CD, IR, MS and molecular modeling experiments. This paper presents the first report on the isolation of true pregnane-type steroids from the Fungi kingdom.
Radulović
Niko
N
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Dang
Ngoc Quang
NQ
Hashimoto
Toshihiro
T
Nukada
Makiko
M
Tanaka
Masami
M
Asakawa
Yoshinori
Y
D001487:Basidiomycota / Q000737:chemistry*; D048690:Fruiting Bodies, Fungal / Q000737:chemistry; D007564:Japan; D011277:Pregnanediones / Q000737:chemistry* / Q000302:isolation & purification*; D011281:Pregnatrienes / Q000737:chemistry* / Q000302:isolation & purification*
C502849:1alpha,2beta,3alpha-trihydroxypregna-4,7,16-trien-12,20-dione; C502850:2beta,3alpha-dihydroxypregna-4,7,16-trien-12,20-dione; D011277:Pregnanediones; D011281:Pregnatrienes; C071134:stizophyllin