Tricyclic and Spirobicyclic Norsesquiterpenes from the Endophytic Fungus Pseudolagarobasidium acaciicola

Abstract

The new tricyclic and spirobicyclic norsesquiterpenes 1 and 2 and the new nor-chamigrane endoperoxide 3, together with the known sesquiterpenes steperoxide A (4), merulin B (5), and merulin C (6), were isolated from the endophytic fungus Pseudolagarobasidium acaciicola. The structures and absolute configurations of 1-3 were determined by analysis of spectroscopic data, as well as by single-crystal X-ray

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

“…373 A novel norsesquiterpenes, acaciicolin A ( 1011 ) with an undescribed acaciicolane norsesquiterpene skeleton featuring 6/5/5 fused tricyclic ring system, was isolated from the endophytic fungus P. acaciicola , whose structure and configuration was assigned by single-crystal X-ray analysis. 358…”

“…The Penicillium strains yielded three sulfur-containing cytotoxic curvularin macrolides, sumalarins A-C (352-354), 180 one simple curvularin macrolide 345, 64 and a 10-membered macrodiolide, mangrovlide A (356). 181 Investigation of the Pestalotiopsis strains PSU-MA92 and PSU-MA119 resulted in the isolation of two new seiricuprolides, pestalotioprolides A (357) and B (358). 182 From another Pestalotiopsis strain, seven new 14-membered macrolides, pestalotioprolides C-H (359-364), and 7-O-methylnigrosporolide (365), were isolated and compounds 360-362 and 365 showed signicant cytotoxicity against the murine lymphoma cell line L5178Y with IC 50 values of 5.6, 3.4, 3.9, and 0.7 mM.…”

“…356 Recently, an endophytic fungus Pseudolagarobasidium acaciicolat could powerfully produce a series of nor-chamigrane endoperoxides and chamigrane sesquiterpenes 928-949. 357,358 Compound 945 displayed cytotoxicity against eight cancer lines with IC 50 ranging from 0.28-37.46 mM and normal cell line (IC 50 17.92 mM). 357 The result suggested that 945 displayed selective cytotoxicity against the HL-60 cell line (IC 50 0.28 mM) with the selectivity index (SI) value of 64.0.…”

Structure and absolute configuration assignments of ochracines F–L, chamigrane and cadinane sesquiterpenes from the basidiomycete Steccherinum ochraceum HFG119

“…2,3 Most reported chamigranes are generally produced by the red alga of the genus Laurencia (Family Rhodomelaceae) [4][5][6][7][8] and endophytic fungi. [9][10][11][12][13][14] Our previous chemical study on Steccherinum ochraceum resulted in the isolation of four rare endoperoxide type chamigranes, namely steperoxides A-D, of which steperoxides C and D exhibited antimicrobial activity. 2,3 Since natural endoperoxides are of special interest, they have attracted and continue to attract considerable attention for their bioactivities.…”

Hot off the press

“…Acaciicolin A 1 and spiroacaciicolide A 2 are metabolites of the endophytic fungus Pseudolagarobasidium acaciicola with new skeletons. 1 A biosynthetic pathway to these norsesquiterpenoid metabolites from the co-occurring norchamigrane derivative 3 has been proposed. The Chinese medicinal plant Croton crassifolius is the source of crocrassin A 4 that has a new sesquiterpenoid skeleton.…”