Structural effects on the bioactivity of dehydroabietic acid derivatives.
The synthesis and the evaluation of the antimicrobial activity against a filamentous fungus, yeasts and bacteria of 15 hydrophenanthrene compounds derived from dehydroabietic acid, bearing different functional groups and different stereochemistry of the A/B ring junction are disclosed. The results obtained showed how their activity is dependent of the functionality at C-18, which can be increased by deisopropylation or introduction of other groups into the molecule. While the filamentous fungus tested is sensitive to almost all of the compounds under study, the aldehyde function showed to be of major importance to the inhibition of yeast. Alcohols and aldehyde C-18 derivatives also inhibit the growth of a Gram-positive bacteria, whereas Gram-negative are not sensitive.
Gigante
Bárbara
B
Departamento de Tecnologia de Indústrias Quimicas and Laboratório de Microbiologia Industrial, Instituto Nacional de Engenharia e Tecnologia Industrial, Lisboa, Portugal. barbara.gigante@ineti.pt
Silva
Ana M
AM
Marcelo-Curto
Maria João
MJ
Feio
Sónia Savluschinske
SS
Roseiro
José
J
Reis
Lucinda V
LV
D045784:Abietanes; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010946:Plants, Medicinal / Q000737:chemistry; D013329:Structure-Activity Relationship
D045784:Abietanes; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D004224:Diterpenes; C013913:dehydroabietic acid