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Tetrasubstituted α-pyrone derivatives from the endophytic fungus, Neurospora udagawae

2019; Elsevier BV; Volume: 35; Linguagem: Inglês

10.1016/j.phytol.2019.11.010

1876-7486

Allan Patrick G. Macabeo, Allaine Jean C. Cruz, Abolfazl Narmani, Mahdi Arzanlou, Asadollah Babai‐Ahari, Luis Agustin E. Pilapil, Katherine Yasmin M. Garcia, Volker Hüch, Marc Stadler,

Chemical synthesis and alkaloids

Two new α-pyrone derivatives, udagawanones A (1) and B (2), along with the known compounds (Z)-4-hydroxy-3-(3-hydroxy-3-methylbut-1-en-1-yl)benzoic acid (3), isosclerone (4), cyclo-(L-Leu-L-Pro) (5), and cyclo-(L-Pro-L-Tyr) (6), were isolated from cultures of the endophyte Neurospora udagawae. Their structures were elucidated by extensive spectroscopic methods and single crystal X-ray diffraction. Both compounds feature oxidized functionalities at the C-2 position not previously observed in other tetrasubstituted α-pyrones from fungi. Compound 1 exhibited moderate antibacterial (vs. Staphylococcus aureus) and antifungal (vs. Rhodoturula glutinis) activities and cytotoxicity against KB3.1 cells.