α‐Pyrones and Pyranes from the Plant Pathogenic Fungus Pestalotiopsis scirpina

Abstract

Three new α‐pyrones, scirpyrones A–C (1–3), and four new pyranes, scirpyranes A–D (4–7), were isolated from solid cultures of the plant pathogen Pestalotiopsis scirpina. Their structures were elucidated primarily by NMR experiments. The absolute configurations of C‐7 and C‐2′ in 1, C‐7 in 2, and C‐6 and C‐7 in 3 were deduced on the basis of circular dichroism (CD) data, whereas those of the secondary alcohols in 4–7 were determined by a modification of Mosher's method. Compound 1 is the first described 6‐(5‐oxotetrahydrofuran‐2‐yl)‐2H‐pyran‐2‐one. Compounds 4–6 showed significant cytotoxicity towards MCF‐7 cells.

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

“…Compounds 3 -6 were identified as LL-P880g (3) [13], scirpyrone A (4) [15], scirpyrone B (5) [15], and 6-pentyl-4-methoxy-pyran-2-one (6) [16] by comparison of their NMR and MS data with those reported.…”

Bioactive Natural Compounds from the Plant Endophytic Fungi Pestalotiopsis spp.

“…6 exhibited moderate cytotoxicity against the murine cancer cell line L5178Y with an EC 50 value of 8.93 ,g/mL. Studies on the plant endophyte P. fici have yielded [12][13][14] sixteen new chromone derivatives pestaloficiols A-P (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23) [15] four new metabolites pestalotheols A-D (24)(25)(26)(27). Pestalotheol C (26) displayed an inhibitory effect on HIV-1 LAI replication in C8166 cells.…”

“…The investigation of the chemical constituents of the plant endophytic fungus P. zonata, isolated from Cyrtotachys lakka in Hainan, China, resulted in the isolation [22] [24]. Chloropupukeananin (59), the first pupukeanane chloride with highly functionalized tricyclo-[4.3.1.0 3,7 ]decane skeleton, has been isolated [25] from the plant endophyte P. fici.…”

Synthesis of Bioactive Side‐Chain Analogues of TAN‐2483B

“…Structurally, TAN‐2483A and B contain a furo[3,4‐ b ]pyran‐5‐one core, which is common to a small family of bioactive fungal metabolites including members of the waols, massarilactones, fusidilactones, scirpyranes and thiessenolactones (Figure b) …”