In vitro anti-influenza screening of several Euphorbiaceae species: structure of a bioactive Cyanoglucoside from Codiaeum variegatum.
A bio-guided screening against influenza A virus (FLUAV) was carried out with seven Euphorbiaceae species. The results showed that chromatographic fractions from Phyllantus niruri, Euphorbia pulcherrima and Codiaeum variegatum had relevant anti-FLUAV activity, although only chromatographical subfractions from C. variegatum kept the activity. From this plant, the active compound against FLUAV was isolated. Its structure was assigned as 2-(3,4,5)-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxymethyl)acrylonitrile (1) on the basis of NMR, mass spectrometry and X-ray diffraction analysis. The compound displayed virucidal activity without impairment of haemagglutination properties of the used virus strain. This is the first report indicating antiviral activity of a cyanoglucoside.
Forero
Jorge Eduardo
JE
Grupo de Inmunovirología, Sede de Investigaciones Universitarias, Universidad de Antioquia, Medellín, Colombia.
Avila
Liliana
L
Taborda
Natalia
N
Tabares
Paula
P
López
Albeiro
A
Torres
Fernando
F
Quiñones
Winston
W
Bucio
María A
MA
Mora-Pérez
Yolanda
Y
Rugeles
Maria Teresa
MT
Joseph-Nathan
Pedro
P
Echeverri
Fernando
F
D000181:Acrylonitrile / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D004285:Dogs; D019665:Euphorbiaceae / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006601:Hexoses / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009980:Influenza A virus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D019906:Nuclear Magnetic Resonance, Biomolecular; D014961:X-Ray Diffraction
C534607:2-((3,4,5)-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxymethyl)acrylonitrile; D000998:Antiviral Agents; D005960:Glucosides; D006601:Hexoses; D000181:Acrylonitrile