Triterpenes from the Mushroom Hypholoma lateritium : Isolation, Structure Determination and Investigation in Bdelloid Rotifer Assays.

Twelve compounds ( 1 ⁻ 12 ) were isolated from the methanol extract of brick cap mushroom ( Hypholoma lateritium (Schaeff.) P. Kumm.). The structures of the compounds were elucidated using extensive spectroscopic analyses, including NMR and MS measurements. Lanosta-7,9(11)-diene-12β,21α-epoxy-2α,3β,24β,25-tetraol ( 1 ) and 8-hydroxy-13-oxo-9 E ,11 E -octa-decadienoic acid ( 2 ) were identified as new natural products, together with ten known compounds, from which 3β-hydroxyergosta-7,22-diene ( 4 ), demethylincisterol A2 ( 5 ), cerevisterol ( 6 ), 3β- O -glucopyranosyl-5,8-epidioxyergosta-6,22-diene ( 7 ), fasciculol E ( 9 ), and uridine ( 12 ) were identified in this species for the first time. The isolated triterpenes ( 1 , 3 ⁻ 11 ) were investigated for their toxicity in vivo using bdelloid rotifer assays. Most of the examined steroids in general showed low toxicity, although the effects of the compounds varied in a wider range from the non-toxic lanosta-7,9(11)-diene-12β,21α-epoxy-2α,3β,24β,25-tetraol ( 1 ) to the significantly toxic cerevisterol ( 6 ), with substantial dependence in some cases on the presence of nutrient in the experimental environment.