Fungal polyketides from a rhizospheric soil-derived Penicillium sp. YUD17004 associated with Gastrodia elata

Antifeedant, Antifungal Cryptic Polyketides with Six Structural Frameworks from Tea Endophyte Daldinia eschscholtzii Propelled by the Antagonistic Coculture with Phytopathogen Colletotrichum pseudomajus and Different Culture Methods

“…The NMR database by Kishi stated that the chemical shifts of C-3 can be used to determine the relative configuration of the 1,3,5-triol system with the scopes of δ C 68.5 ± 0.5 for an anti / syn or syn / anti , δ C 66.3 ± 0.5 for an anti / anti , and δ C 70.4 ± 0.5 for a syn / syn configuration (Figure ). , Because the chemical shift of C-5 in 18 was at δ C 69.6 (CD 3 OD), C-3/C-5 and C-5/C-7 were determined as an anti/syn or syn/anti relative configuration, and the absolute configuration of 18 was further confirmed by the biogenesis of pyranlyketide ( 24 ) …”

“…Other compounds were determined as (2 S ,4 S ,5 R )-hept-6-en-2,4,5-triol ( 4 ), hypoxylonol H ( 6 ), and 5-methyl-2-vinyltetrahydrofuran-3-ol ( 7 ), (2 R ,4 S )-2,3-dihydro-2-methyl-benzopyran-4, 5-diol ( 8 ), (2 S ,4 S )-3,4-dihydro-4-methoxy-2-methyl-2 H -1-benzopyran-5-ol ( 9 ), guhypoxylonol B ( 21 ), nodulisporol ( 22 ), and pyranlyketide ( 24 ) from the coculture of the endophytic fungus D. eschscholtzii and phytopathogen C.…”

“…18,19 Because the chemical shift of C-5 in 18 was at δ C 69.6 (CD 3 OD), C-3/C-5 and C-5/C-7 were determined as an anti/syn or syn/anti relative configuration, and the absolute configuration of 18 was further confirmed by the biogenesis of pyranlyketide (24). 20 The molecular formula C 12 H 20 O 4 of daldinrin J ( 19) was determined by 13 C NMR and HRESIMS data. 1 H and 13 C NMR spectroscopic analysis (Table 6) exhibited that the skeleton was highly similar to that of theissenepoxide.…”

“…The molecular formula C 19 H 30 O 7 of daldinrin L (23) was determined by 13 C NMR and HRESIMS data. The 1 H NMR and 13 C NMR spectra (Table 7) of 23 were similar to those of 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol, 23 Other compounds were determined as (2S,4S,5R)-hept-6en-2,4,5-triol (4), 11 hypoxylonol H (6), 24 and 5-methyl-2-vinyltetrahydrofuran-3-ol (7), 16 (2R,4S)-2,3-dihydro-2-methylbenzopyran-4, 5-diol (8), 15 (2S,4S)-3,4-dihydro-4-methoxy-2methyl-2H-1-benzopyran-5-ol (9), 14 guhypoxylonol B (21), 22 nodulisporol ( 22), 25 and pyranlyketide (24) 20 from the coculture of the endophytic fungus D. eschscholtzii and phytopathogen C. pseudomajus. D. eschscholzii was famous to producing abundant polyketides.…”