Sulfation mediates activity of zosteric acid against biofilm formation.
Zosteric acid (ZA), a metabolite from the marine sea grass Zostera marina, has attracted much attention due to its attributed antifouling (AF) activity. However, recent results on dynamic transformations of aromatic sulfates in marine phototrophic organisms suggest potential enzymatic desulfation of metabolites like ZA. The activity of ZA was thus re-investigated using biofilm assays and simultaneous analytical monitoring by liquid chromatography/mass spectrometry (LC/MS). Comparison of ZA and its non-sulfated form para-coumaric acid (CA) revealed that the active substance was in all cases the non-sulfated CA while ZA was virtually inactive. CA exhibited a strong biofilm inhibiting activity against Escherichia coli and Vibrio natriegens. The LC/MS data revealed that the apparent biofilm inhibiting effects of ZA on V. natriegens can be entirely attributed to CA released from ZA by sulfatase activity. In the light of various potential applications, the (a)biotic transformation of ZA to CA has thus to be considered in future AF formulations.
a Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics , Friedrich Schiller University Jena , Jena , Germany.
Caroline
C
Kurth
Levent
L
Cavas
Georg
G
Pohnert
D018441:Biofilms / Q000187:drug effects*; D002853:Chromatography, Liquid; D002934:Cinnamates / Q000138:chemical synthesis / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry; D011422:Propionates; D013429:Sulfatases; D013431:Sulfates / Q000737:chemistry*; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis / Q000737:chemistry*; D014733:Vibrio / Q000187:drug effects; D035962:Zosteraceae / Q000737:chemistry
D002934:Cinnamates; D003373:Coumaric Acids; D010936:Plant Extracts; D011422:Propionates; D013431:Sulfates; D013463:Sulfuric Acid Esters; C503399:zosteric acid; D013429:Sulfatases; C495469:p-coumaric acid
Escherichia coli; Vibrio natriegens; antifouling; biofilm inhibition; para-coumaric acid; sulfatase activity; zosteric acid