TY - JOUR
T1 - Antimycobacterial metabolites from Plectranthus
T2 - Royleanone derivatives against Mycobacterium tuberculosis strains
AU - Rijo, Patrícia
AU - Simões, M. Fátima
AU - Francisco, A. Paula
AU - Rojas, Rosario
AU - Gilman, Robert H.
AU - Vaisberg, Abraham J.
AU - Rodríguez, Benjamín
AU - Moiteiro, Cristina
PY - 2010/4
Y1 - 2010/4
N2 - The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.
AB - The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.
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U2 - 10.1002/cbdv.200900099
DO - 10.1002/cbdv.200900099
M3 - Article
C2 - 20397225
AN - SCOPUS:77951197862
SN - 1612-1872
VL - 7
SP - 922
EP - 932
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
IS - 4
ER -