Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
Twenty-three hydroquinone and quinone derivatives were assayed for antimicrobial effects and brine shrimp and fish lethalities, to establish relevant structure-activity relationships (SAR). Linear 2-prenyl-1,4-hydroquinones used for bioassay were obtained either by isolation from the sponge Ircinia spinosula or by synthesis. Corresponding quinones, as well as hydroquinones possessing saturated side-chains composed of one to eight isopentane units, were also synthesized and biologically evaluated. Terpenoid 1,4-benzoquinones displayed moderate antimicrobial activity against three microorganisms, SAR studies indicate the optimum length of the side-chain is in the range of five to fifteen carbon atoms.
De Rosa
S
S
Istituto per la Chimica di Molecole di Interesse Biologico CNR, Napoli, Italy.
De Giulio
A
A
Iodice
C
C
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001156:Artemia; D001419:Bacteria / Q000187:drug effects*; D003532:Cyprinodontiformes / Q000502:physiology*; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects*; D006873:Hydroquinones / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D008826:Microbial Sensitivity Tests; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D006873:Hydroquinones; D013729:Terpenes