Five New Meroterpenoids from the Fruiting Bodies of the Basidiomycete Clitocybe clavipes with Cytotoxic Activity

Abstract

Five new meroterpenoids, clavipols A–B (1–2) with a 12-membered ether ring and clavilactones G–I (3–5) having a 10-membered carbocycle connected to a hydroquinone and an α,β-epoxy/unsaturated lactone, were obtained from the fruiting bodies of the basidiomycete Clitocybe clavipes. Their structures were determined by comprehensive analysis of their spectroscopic data, and the absolute configuration of 1 was established by quantum chemical calculations of electronic circular dichroism (ECD). All the isolated compounds (1–5) were tested for their cytotoxic activity against three human tumor cell lines (Hela, SGC-7901, and SHG-44) in vitro after treatment for 48 h. Compound 4 exhibited moderate cytotoxic activity against Hela and SGC-7901 tumor cell lines, with IC50 values of 23.5 and 14.5 µM, respectively.

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

“…Subsequently, clavipols A-B (13-14) containing a 12-membered ether ring and clavilactones G-I (15)(16)(17) were isolated from the fruiting bodies of A. clavipes collected in China. Compound 16 exhibited moderate cytotoxic activity against Hela and SGC-7901 cancer cell lines, with IC 50 values of 23.5 and 14.5 µM, respectively [71]. Five fatty acid derivatives, isolated from A. clavipes have been reported to have potent strong inhibitory activity against aldehyde dehydrogenase [65].…”

Four Meroterpenoids with Novel Aminoglycoside Moiety from the Basidiomycete Clitocybe clavipes with Cytotoxic Activity

“…Our group has long been interested in this type of structure and discovered several kinds of novel clavilactones from Clitocybe clavipes . For instance, clavilactones G-K were isolated, which all possessed a 10-membered carbocycle connected to a hydroquinone with moderate cytotoxic activities [ 17 , 18 ]. Previously, we have reported the isolation of two kinds of novel nitrogen-containing meroterpenoids, clavipyrrine A [ 19 ] and clavipines A–C [ 20 ], from the basidiomycete Clitocybeclavipes .…”

ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp.

“…The clavilactones are a family of meroterpenoids containing a constrained 10-membered ring fused to a 2,3-epoxy-γ-lactone and a benzoquinone or hydroquinone from cultures of the edible mushroom Ampulloclitocybe clavipes (synonym Clitocybe clavipes ). , Since the initial isolation of clavilactones A–C, derivatives clavilactone D, , E, F, G–I, and J and K have been isolated from the same producing species. The derivatives differ from parental clavilactones A and B by hydroxylation or amination at different locations (Figure S23).…”