Polyketides from the Littoral Plant Associated Fungus Pseudallescheria boydii

Abstract

Four previously unreported chemical entities, boydone A (1), boydone B (2), botryorhodine F (3), and botryorhodine G (4), along with five known compounds, fusidilactone A (5), (R)-(-)-mevalonolactone (6), (R)-(-)-lactic acid (7), ovalicin (8), and botryorhodine C (9), were isolated from the ethyl acetate extracts of the fermented broths of the fungal strain Pseudallescheria boydii NTOU2362. The structures of 1-9 were characterized on the basis of their spectroscopic data analyses. The absolute configurations of 1 and 2 were established by comparison with the literature and the modified Mosher's method. The growth inhibitory activities of 1-9 against the A549 non-small-cell lung cancer cell line were evaluated, and 2 and 8 exhibited moderate to potent bioactivities with GI₅₀ values of 41.3 and 4.1 μM, respectively, in comparison with fluorouracil (GI₅₀ = 3.6 μM).

Pseudaboydins A and B: Novel Isobenzofuranone Derivatives from Marine Fungus Pseudallescheria boydii Associated with Starfish Acanthaster planci

“…Pseudallescheria boydii is deemed to be a human pathogenic fungus and can cause a variety of infections, especially in the immunocompromised and immunocompetent patients. However, up to now, the literature reports on the secondary metabolites of this fungus are still limited [8,9,10,11,12,13]. The literature survey prompted us to investigate the metabolites of the fungus, Pseudallescheria boydii .…”

Antibacterial epipolythiodioxopiperazine and unprecedented sesquiterpene from Pseudallescheria boydii, a beetle (coleoptera)-associated fungus

“…10,11 Concerning its generation of bioactive secondary metabolites, the antifungal tyroscherin and N-methyltyroscherin have been characterized from a culture of P. boydii isolated from a termite Nasutitermes sp. ; 12 the P. boydii strain residing in the littoral plant Sesuvium portulacastrum is able to produce cytotoxic polyketide boydone B; 13 another P. boydii strain isolated from afflicted patients generates cyclic peptides pseudacyclins A-E. 14 Few attempts, however, have been focused on the small molecule compounds biosynthesized by any P. boydii strain associated with insects. In the light of the speedier gene modification of symbionts, 15,16 the intricate interaction of P. boydii with its insect host was presumed to facilitate the production of a uniquely structured compound library, from which new bioactive molecules may be screened.…”

Phaeophleospora vochysiae Savi & Glienke sp. nov. Isolated from Vochysia divergens Found in the Pantanal, Brazil, Produces Bioactive Secondary Metabolites

“…Finally, the relative configuration at the stereocenters were indirectly established through the analyses of NOESY correlations (Figure S3 ), and by comparison to those of the reported cyclopentenone ring-contracted analogues, such as similin A ( 4 ) (produced by the fungus Sporormiella similis ) 18 , phomapentenone A ( 5 ) (produced by the fungus Phoma sp. NRRL 25697) 19 and boydone B ( 6 ) (produced by the plant associated Pseudallescheria boydii NTOU2362) 20 (Figure S41 ). Thus, thorough cumulative analyses of 1D ( 1 H 13 ,C) and 2D (HSQC 1 ,H 1 ,H-COSY, TOCSY, HMBC and NOESY) NMR spectra established the structure of 3 as -( sec -butyl)-6-ethyl-4,5-dihydroxy-2-methoxy-6-methylcyclohex-2-enone (Fig.…”

“…ring-contracted analogues compared to 3 , such as similin A ( 4 , produced by the fungus Sporormiella similis ) 18 , phomapentenone A ( 5 , produced by the fungus Phoma sp. NRRL 25697) 19 and boydone B ( 6 , produced by the plant associated Pseudallescheria boydii NTOU2362) 20 (Figure S41 ). The cercosporins are photosensitizing compounds that interact with molecular oxygen to produce highly toxic singlet oxygen 32 .…”