Bioactive 1,4-Dihydroxy-5-phenyl-2-pyridinone Alkaloids from Septoria pistaciarum (Ascomycetes)

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

“…In conclusion, this work separated and fully identified fourteen eremophilane sesquiterpenoids (1−14), including nine new ones, septoreremophilanes A−I (1−9), one known eduesmane-type sesquiterpene (15), two known guaiane-type sesquiterpenes (16,17), two described tetralone congeners (18,19), and two known cholesterol derivatives (20,21) from cultures of the S. rudbeckiae fungus. The effects of all metabolites against eight bacteria were estimated in vitro, and the novel metabolites (1−9) were tested for antineuroinflammatory…”

“…The computed ECD curve (Figure S81) for the model molecule of 9 comparable with the experimental ECD curve established the chiral centers to be 4R, 5S, 7R, and 8R configuration. The remaining reported metabolites were affirmed as dihydrobipolaroxin D (10), 33 2β-hydroxyeremophila-1(10),11-(13)-dien-12-oic acid (11), 34 7-epi-tessaric acid (12), 34 (1β,4aβ,7β,8aβ)-octahydro-7-[1-(hydroxymethyl)ethenyl]-1,8α-dimethylnaphthalen-4α(2H)-ol (13), 35 debneyol ( 14), 1 cyperusol C (15), 36 epi-guaidiol (16), 37 guaidiol (17), 36 4,8dihydroxy-3,4-dihydro-2H-naphthalen-1-one ( 18), 38 trans-3,4dihydro-3,4,8-trihydroxynaphthalene-1-(2H)-one (19), 39 (22E)-3β-hydroxy-26,27-bisnorcholesta-5,22-dien-24-one (20), 40 and cholesterine (21), 41 according to the comparison of those data of NMR and specific rotations with the publications.…”

“…18 Moreover, a series of 5-phenyl-2-pyridinone alkaloids from the fungus Septoria pistaciarum displayed antibacterial and antimalarial effects. 19,20 The perennial shrub Karelinia caspia (Pallas) Lessing (Asteraceae) possesses both salt-alkali and drought-resistant effects, which allows it to play an important role in improving the saline-alkali soil, reducing wind erosion and desertification, and conservating water and soil in agriculture. 21,22 In the Xinjing Uyghur Autonomous Region located on western China, the fungus S. rudbeckiae widely invaded the halophyte K. caspia and caused critical stem decay and leaf spot disease.…”

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Fourteen eremophilane sesquiterpenoids (1−14), including nine new congeners, septoreremophilanes A−I (1−9), together with three known sesquiterpenes (15−17), two known tetralone derivatives (18,19), and two known cholesterol analogues (20, 21), were isolated from the endophytic fungus Septoria rudbeckiae. Compounds 1−6 and 7a belong to the family of the highly oxygenated eremophilane sesquiterpenoids with a 6/6/5 tricyclic system and bearing a hemiacetal moiety.

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Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues

“…In addition to their antiviral activity, 2-pyridinone derivatives are known to possess activity against wild type [9,10] and resistant [11] bacterial strains. The derivatives have also been shown to be antifungal [12] and antiprotozoal agents [13,14].…”