Cytotoxic Drimane Sesquiterpenoids Isolated from Perenniporia maackiae

Abstract

A chemical investigation of a basidiomycetes fungus, Perenniporia maackiae, led to the discovery of 12 drimane sesquiterpenoids, including seven new constituents (1-7). The elucidation of the structures was performed via interpreting extensive spectroscopic methods, including ECD calculations. Among all isolated compounds, 1, 2, and 6 exhibited cytotoxicity toward six carcinoma cells, including ACHN, HCT-15, MDA-MB-231, NCI-H23, NUGC-3, and PC-3 cells, with half-maximal inhibition of cell proliferation values of 1.2-6.0 μM.

Xylodon flaviporus-Derived Drimane Sesquiterpenoids That Inhibit Osteoclast Differentiation

“…The 1 H NMR data (Table ) showed three methyl signals (δ H 1.30, 1.19, and 0.98), five methylene signals, including one oxymethylene (δ H 4.63, 4.57, 2.97, 2.64, 2.37, 1.68, 1.56, 1.47, 1.33, and 1.27), and two methine signals, including one oxymethine (δ H 5.54 and 1.75). In particular, the appearance of three characteristic methyl signals was indicative of a drimane sesquiterpenoid derivative, in accordance with our previous report . In addition, cinnamoyl group signals (δ H 7.73, 7.56, 7.42, and 6.45) were present.…”

Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

“…These compounds display a diverse array of biological activities, including cytotoxic [6], antibacterial [4], nitric oxide inhibitory [5], nematicidal [7], anti-inflammatory [8], and growth inhibition of marine phytoplankton activities [9], which continues to stimulate efforts to discover new sesquiterpenes from nature. Drimane sesquiterpenes, as an important family of sesquiterpenes, showed potent cytotoxic activities against a wide cell variety, including HL-60, SMMC-721, A-549, ACHN, HCT-15, MDA-MB-231, NCI-H23, NUGC-3, and PC-3 cells [10,11].…”

Biosynthesis of Fungal Drimane‐Type Sesquiterpene Esters

“…The here identified compounds 1-6, 8-10, 12-14 and 16,h ave already been reported in Aspergillus ustus, [14] with 5 and 6 also having been identified in Aspergillus flavus. [15] However,w e also isolated af ew novel derivatives,n amed calidoustene A (7), calidoustene B( 11)a nd calidoustene C( 15,S cheme 1).…”

“…[12] Thep revious studies on the biosynthesis of astellolides suggested that drim-8-ene-11-ol is the used precursor,p roduced by the haloacid dehalogenase-like (HAD-like) terpene cyclase AstC and two dephosphorylases. Nonetheless,w hile astellolides harbor a D 8,9 double bond, other isolated compounds like nanangenines,2 2-hydroxyxylodonin Band purpuride Fcontain adouble bond at adifferent position (D 7,8 ), suggesting ad ifferent biosynthesis (Figure 1).…”

“…Drimane-type sesquiterpenes are alarge group of natural products with unique C 15 bicyclic skeletons.T hey have been identified in various eukaryotes including plants, [1] liverworts, [2] molluscs, [2] sponges, [2] and fungi (primarily Aspergillus [3] and Penicillium [4] species). Many of them possess "druglike" chemical properties and display diverse biological activities,i ncluding antimicrobial, [5] anti-inflammatory, [6] cytotoxic, [7] neurotransmission, [8] anti-diabetic, [1a] and antihyperlipidemic [9] activity.M oreover,t he well-known drimane dialdehydes act as antifeedants against insects and have potential to be used as alternative insecticides. [10] Because of their interesting structural features and biological activities,f ungi-derived drimanes have attracted increasing attention.…”