Nodulisporipyrones A–D, new bioactive α-pyrone derivatives fromNodulisporiumsp.

Abstract

Four new α-pyrone derivatives, nodulisporipyrones A-D (1-4), were isolated from the extract of an endolichenic fungal strain Nodulisporium sp. (65-12-7-1) that was fermented with rice. The structures of 1-4 were elucidated by extensive spectroscopic analysis, and the absolute configurations were determined by modified Mosher's method and electronic circular dichroism experiments. Their antimicrobial activities against Staphylococcus aureus 209P, Escherichia coli ATCC0111, Aspergillus niger R330, and Candida albicans FIM709 were evaluated using a paper disk diffusion method. Nodulisporipyrones A-D (1-4) are the first α-pyrone derivatives from Nodulisporium fungi.

Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-Ones Chemodiversity in a Marine-Sourced Penicillium restrictum

“…The coupling constant 3 J H1’-H2’ = 4.0 Hz and a correlation observed between H-1’ and H-2’ in the NOESY spectrum experiment of 5 indicated that they were syn and that the relative configuration of 5 was 1’ R *,2’ S * or 1’ S *,2’ R *. The optical rotation of compound 5 , with [α] + 63 (c 1.0, MeOH), had the same sign than (1’ R ,2’ S )-LL-P880γ and (1’ R ,2’ R )-LL-P880γ and the ECD spectrum of compound 5 (Δε 281.9nm = +2.042) exhibited a positive Cotton effect at 282 nm already described for 6-(1 R , 2’ R -dihydroxyheptyl)-4-methoxy-2 H -pyran-2-one and 6-(1 R , 2’ S -dihydroxyheptyl)-4-methoxy-2 H -pyran-2-one [ 64 ]. These observations allowed the assignment of the structure and absolute configuration of 5 as the new natural product (1’ R , 2’ S )-LL-P880γ, previously described as a synthetic compound [ 69 ] and reported from Xylaria feejeenisis but without stereochemistry data [ 70 ].…”

“…Their absolute configuration has been, for most of them, deduced from diagnostic coupling constants of the H-6-H-1’-H2’ system, which we investigated in the 1 H NMR spectrum of 2 . The 3 J H-6-H-1’ ( J = 2.0 Hz) of 2 was different to that of (6 S ,1’ R ,2’ S )-nodulisporipyrone D ( 3 J H-6-H-1’ = 6.5 Hz) [ 64 ] and (6 R , 1’ S , 2’ R )-LL-P880 β ( 3 J H-6-H-1’ = 6.7 Hz) [ 65 ] but similar to that of (6 S ,1’ S ,2’ S )-LL-P880 β ( 3 J H-6-H-1’ = 1.1 Hz) [ 66 ], which indicated that the relationship between H-6 and H-1’ was syn . Moreover, the 3 J H-1’-H-2’ ( J = 6,7 Hz) of 2 was equivalent to that of (6 S ,1’ R ,2’ R )-LL-P880 β ( 3 J H-1’-H-2’ = 6.1 Hz) [ 67 ] and in the same order as that of (6 R ,1’ R ,2’ R )-LL-P880 β ( 3 J H-1’-H-2’ = 9.2 Hz) [ 67 ] and (6 S ,1’ S ,2’ S )-LL-P880 β ( 3 J H-1’-H-2’ = 9.1 Hz) [ 66 ], which identified that the relationship between H-1’ and H-2’ was anti .…”

Co-cultivation With 5-Azacytidine Induced New Metabolites From the Zoanthid-Derived Fungus Cochliobolus lunatus

“…These spectroscopic and structure features of α-pyrone moiety were almost identical to the reported 4-methoxy-6-subtituted α-pyrones, nodulisporipyrones B–C from fungus Nodulisporium sp. (Zhao et al, 2015). The analysis of contiguous sequence of 1 H– 1 H COSY correlations from H-7 to H-13 allowed us to establish a spin system from C-7 to C-13 belonging to a seven numbered aliphatic side-chain (Figure 3).…”

Osteoclastogenesis Inhibitory Polyketides from the Sponge‐Associated Fungus Xylaria feejeensis

“…[1] Secondary metabolites reported from this genus include polyketides, [2,3] terpenoids [4,5] and sterols. [6] Polyketides of α-pyrone derivatives are one class of the most important secondary metabolites, showing a broad spectrum of biological activities, such as cytotoxic, [7] antifungal, [8] anti-inflammatory and immunomodulatory activities. [9] As part of our continuous search for bioactive metabolites from marine invertebrates and associated fungi, [10 -13] a strain of X. feejeensis was isolated from the sponge Stylissa massa collected from the Dongsha in the South China Sea.…”