Atlanticones, New Protoilludane Sesquiterpenes from the MushroomLactarius atlanticus (Basidiomycetes

Abstract

A chemical investigation of the fruiting bodies of Lactarius atlanticus (Russulaceae, Basidiomycetes) resulted in the isolation of new protoilludane sesquiterpenes, namely esters of atlanticones A (1) and B (2), and atlanticones C (3) and D (4). The former two compounds were isolated from intact carpophores, whereas the remaining two were isolated from

Sesquiterpenes of Lactarius and Russula (Mushrooms): An Update[1]

“…Four years after this discovery, a chemical investigation of the fruiting bodies of Lactarius atlanticus allowed us to isolate four new protoilludane sesquiterpenes, named atlanticones A-D (38)(39)(40)(41) [30]. Extraction of undamaged fruiting bodies afforded enone 38 and the corresponding β-epoxide 39, both as a mixture of oleate and linoleate esters, in a ratio of 9:1.…”

“…The structures of rulepidadienes A(30) and B(32), were established by standard NMR techniques. Nardosinane sesquiterpenes, as 31 and 32, are believed to derive in nature from aristolane precursors.…”

Terpenoids and Sterols from Mushrooms

“…atlanticus ( Fig. The former two compounds were isolated from intact carpophores, whereas the remaining two were isolated from injured fruiting bodies [25]. The former two compounds were isolated from intact carpophores, whereas the remaining two were isolated from injured fruiting bodies [25].…”

“…Thus, there are monoterpenoids (C 10 ), sesquiterpenoids (C 15 ), diterpenoids (C 20 ), sesterterpenoids (C 25 ), triterpenoids (C 30 ), and tetraterpenoids (C 40 ). Terpenoids are divided into families based on the number of isoprene units from which they are formed.…”

Synthesis of Multisubstituted Silyloxy‐based Donor‐Acceptor Cyclobutanes by an Acid‐Catalyzed [2+2] Cycloaddition

“…The [2+2] cycloadduct 7la possesses the same relative configuration as members of the sterpurane natural product family (e.g., sterpuric acid) (entry 8) . Also, tricyclic cyclobutane 7ma , which has the core structure of the protoilludanes (e.g., atlanticone D), was obtained (entry 9). In contrast, only trace amounts of cycloadducts 7la and 7ma were generated when EtAlCl 2 was used.…”