α-Glucosidase Inhibitors fromPreussia minimoides

Abstract

Extensive fractionation of an extract from the grain-based culture of the endophytic fungus Preussia minimoides led to the isolation of two new polyketides with novel skeletons, minimoidiones A (1) and B (2), along with the known compounds preussochromone C (3), corymbiferone (4), and 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (5). The structures of 1 and 2 were elucidated using 1D and 2D NMR data analysis, along with DFT calculations of H NMR chemical shifts. The absolute configuration of 1 was established by a single-crystal X-ray diffraction analysis and TDDFT-ECD calculations. Compounds 1-4 significantly inhibited yeast α-glucosidase.

Natural Products from Endophytic Fungi Associated with Rubiaceae Species

“…-dihydroxybut-3-enyl)-5H-furan-2-one (21) and (2E,4R)-2,4dimethylnon-2-enoic acid (22); seven phenolic derivatives: p-hydroxyphenyllactic acid (23), phenyllactic acid (24), p-hydroxybenzoic acid (25), p-hydroxybenzaldehyde (26), n-butyl-3,4dihydroxybenzoate (27), n-hexyl-3,4-dihydroxybenzoate (28) and n-octyl-3,4-dihydroxybenzoate (29); and the known compound (2E,4S)-2,4-dimethyloct-2-enoic acid (30) ( Figure 5) [102]. Extracts of solid cultures of Sporormiella minimoides (Sporormiaceae), isolated as an endophytic fungus from leaves Hintonia latiflora collected in Mexico, yielded five polyketides, 3,6-dimethoxy-8methyl-1H,6Hbenzo[de]isochromene-1,9-dione (31), 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3Hbenzo[de]isochromen-9-one (32), 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (33), minimoidiones A (34) and B (35), along with four known compounds: corymbiferone (36), ziganein (37), brocaenol B (38) and preussochromone C (39) [103][104][105]. Two other compounds, 9S,11R(+)-ascosalitoxin (40) and vermelhotin (41), were also produced by endophytes from this plant [105,106].…”

“…In addition, the compounds (3S,4S)-4-hydroxymellein (9), (3S)-8-methylmellein (10), and the quinone derivatives 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione (47), 4S,5S,6S-4hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-en-1-one (48), and 4R,5R-dihydroxy-3-methoxy-5methylcyclohexen-2-en-1-one (49) were obtained ( Figure 6) [108]. Extracts of solid cultures of Sporormiella minimoides (Sporormiaceae), isolated as an endophytic fungus from leaves Hintonia latiflora collected in Mexico, yielded five polyketides, 3,6-dimethoxy-8methyl-1H,6Hbenzo[de]isochromene-1,9-dione (31), 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3Hbenzo[de]isochromen-9-one (32), 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (33), minimoidiones A (34) and B (35), along with four known compounds: corymbiferone (36), ziganein (37), brocaenol B (38) and preussochromone C (39) [103][104][105]. Two other compounds, 9S,11R(+)ascosalitoxin (40) and vermelhotin (41), were also produced by endophytes from this plant [105,106].…”

“…Extracts of solid cultures of Sporormiella minimoides (Sporormiaceae), isolated as an endophytic fungus from leaves Hintonia latiflora collected in Mexico, yielded five polyketides, 3,6-dimethoxy-8-methyl-1H,6Hbenzo[de]isochromene-1,9-dione ( 31 ), 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3H-benzo[de]isochromen-9-one ( 32 ), 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone ( 33 ), minimoidiones A ( 34 ) and B ( 35 ), along with four known compounds: corymbiferone ( 36 ), ziganein ( 37 ), brocaenol B ( 38 ) and preussochromone C ( 39 ) [ 103 , 104 , 105 ]. Two other compounds, 9S,11R(+)-ascosalitoxin ( 40 ) and vermelhotin ( 41 ), were also produced by endophytes from this plant [ 105 , 106 ].…”

“…The best treatment for type 2 diabetes mellitus (TII-DM) involves hyperglycemic control using appropriate therapies. In recent years, substantial efforts to discover effective inhibitors of α-glucosidases from natural sources have been made [ 103 , 104 ]. The polyketide mimimoidione A ( 34 ) isolated from S. minimoides showed an excellent activity against Saccharomyces cerevisiae α-glucosidase (α-GHY), with an IC 50 of 2.9 μM [ 104 ].…”

Insights in Fungal Bioprospecting in Mexico

“…A previous chemical investigation performed by other authors resulted in the isolation of a depsipeptide and two polyketides, sporminarins A and B [16], with antifungal properties against Aspergillus flavus Link [17]. In our exploration, extensive fractionation of an extract from the grain-based culture of P. minimoides led to the isolation of five new polyketides, two of them with novel skeletons, minimoidiones A (4) and B (5), corymbiferone C (6), corymbiferan lactone E (7), and 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (8), along with the known compounds preussochromone C (9), corymbiferone (10), brocaenol B (11), and ziganein (12) [18,19] (▶ Fig. 2).…”