Anti-Respiratory Syncytial Virus Prenylated Dihydroquinolone Derivatives from the Gorgonian-Derived Fungus Aspergillus sp. XS-20090B15

Journal of Natural Products
2014.0

Abstract

Two new prenylated dihydroquinolone derivatives, 22-O-(N-Me-l-valyl)aflaquinolone B (1) and 22-O-(N-Me-l-valyl)-21-epi-aflaquinolone B (2), and two known analogues, aflaquinolones A (3) and D (or a diastereomer of D, 4), were isolated from the mycelia of a gorgonian-derived Aspergillus sp. fungus. The structures of the new compounds were elucidated by spectroscopic methods, ECD spectra, Marfey's method, and chemical conversion. Compounds 1 and 2 display an unusual esterification of N-Me-l-Val to the side-chain prenyl group. Compound 2 exhibited outstanding anti-RSV activity with an IC50 value of 42 nM, approximately 500-fold stronger than that of the positive control ribavirin (IC50 = 20 μM), and showed a comparatively higher therapeutic ratio (TC50/IC50 = 520).

Knowledge Graph

Similar Paper

Anti-Respiratory Syncytial Virus Prenylated Dihydroquinolone Derivatives from the Gorgonian-Derived Fungus <i>Aspergillus</i> sp. XS-20090B15
Journal of Natural Products 2014.0
Anti-Respiratory Syncytial Virus Prenylated Dihydroquinolone Derivatives from the Gorgonian-Derived Fungus <i>Aspergillus</i> sp. XS-20090B15
Journal of Natural Products 2014.0
Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of <i>Aspergillus</i> spp.
Journal of Natural Products 2012.0
Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of <i>Aspergillus</i> spp.
Journal of Natural Products 2012.0
Synthesis and antiviral activity of a series of novel quinoline derivatives as anti-RSV or anti-IAV agents
European Journal of Medicinal Chemistry 2021.0
4-Phenyl-3,4-dihydroquinolone Derivatives from<i>Aspergillus nidulans</i>MA-143, an Endophytic Fungus Isolated from the Mangrove Plant<i>Rhizophora stylosa</i>
Journal of Natural Products 2013.0
4-Phenyl-3,4-dihydroquinolone Derivatives from<i>Aspergillus nidulans</i>MA-143, an Endophytic Fungus Isolated from the Mangrove Plant<i>Rhizophora stylosa</i>
Journal of Natural Products 2013.0
Prenylated quinolinone alkaloids and prenylated isoindolinone alkaloids from the fungus Aspergillus nidulans
Phytochemistry 2020.0
Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502
Bioorganic &amp; Medicinal Chemistry Letters 2017.0
Dysoxylins A−D, Tetranortriterpenoids with Potent Anti-RSV Activity from <i>Dysoxylum </i><i>gaudichaudianum</i>
Journal of Natural Products 2007.0