In vitro antifungal activity of the diterpenoid 7 alpha-hydroxy-8(17)-labden-15-oic acid and its derivatives against Botrytis cinerea.
We investigated the inhibitory effect of the natural diterpenoids, 7alpha-hydroxy-8(17)-labden-15-oic acid (salvic acid, 1), 7alpha-acetanoyloxy-8(17)-labden-15-oic acid (acetylsalvic acid, 2) and the hemisynthetic diterpenoids 7alpha-acyloxy-8(17)-labden-15-oic acids derivatives, 7alpha-propanoyloxy-8(17)-labden-15-oic acid (propanoylsalvic acid, 3), 7alpha-butanoyloxy-8(17)-labden-15-oic acid (butanoylsalvic acid, 4) and 7alpha-isopentanoyloxy-8(17)-labden-15-oic acid (isopentanoylsalvic acid, 5), against Botrytis cinerea. Diterpenoid fungitoxicity was assessed using the radial growth test method. All diterpenoids, with the exception of isopentenoylsalvic acid, inhibited the mycelial growth of B. cinerea in solid media. Shortest side-chain diterpenoids were more effective than the derivatives with longer chains in the inhibition of B. cinerea mycelial growth. The results suggest that hydrophobicity and structural features would be important factors in the antifungal effect of these diterpenoids. Studies on a possible action mechanism of natural diterpenoids, salvic acid and acetylsalvic acid, showed that these diterpenoids exerted their effect by a different mechanism. Salvic acid did not alter cytoplasmic membrane or cause respiratory chain inhibition. Instead, acetylsalvic acid affected the cytoplasmic membrane producing leakage of 260-nm absorbing compounds.
Mendoza
Leonora
L
Facultad de Química y Biología, Universidad de Santiago de Chile, Avenida Bernardo O'Higgins 3363, Santiago, Chile. leonora.mendoza@usach.cl
Espinoza
Pamela
P
Urzua
Alejandro
A
Vivanco
Marcela
M
Cotoras
Milena
M
D000935:Antifungal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects* / Q000254:growth & development; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D036602:Eupatorium / Q000737:chemistry; D018551:Solanum lycopersicum / Q000382:microbiology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018515:Plant Leaves / Q000382:microbiology
D000935:Antifungal Agents; D004224:Diterpenes