title: Anti-respiratory syncytial virus prenylated dihydroquinolone derivatives from the gorgonian-derived fungus Aspergillus sp. XS-20090B15.
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).
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Min
authors.initials: M
authors.lastname: Chen
authors.forename: Chang-Lun
authors.initials: CL
authors.lastname: Shao
authors.forename: Hong
authors.initials: H
authors.lastname: Meng
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: She
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000382:microbiology; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry; D004151:Dipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D015363:Quinolones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012136:Respiratory Syncytial Viruses / Q000187:drug effects*; D012254:Ribavirin / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C000595543:22-O-(N-Me-L-valyl)-21-epi-aflaquinolone B; C000595542:22-O-(N-Me-L-valyl)aflaquinolone B; D000998:Antiviral Agents; D004151:Dipeptides; D015363:Quinolones; C585308:aflaquinolone A; D012254:Ribavirin