Antituberculosis activity of alkylated mulinane diterpenoids.
Natural azorellane and mulinane diterpenoids show antituberculosis activity, which is increased by methylation of their free carboxyl group. We have systematically investigated the effect of alkylation in this class of diterpenoids and found that the profile of bioactivity is relatively unaffected by the introduction of short alkyl groups, both linear and branched. In this investigation, three semisynthetic diterpenoids, 13 hydroxy-mulin-11-en-20-oic acid n-propyl ester (3) and the n-propyl (19) and n-butyl (20) esters of isomulinic acid, showed the strongest antituberculosis activity (MIC=6.25 microg/mL) against a drug-resistant strain of Mycobacterium tuberculosis.
Grupo de Química Orgánica, Unidad de Biotecnología del Centro de Investigación Científica de Yucatán, Calle 43 No 130, Colonia Chuburná, Mérida, Yucatán, 97200 México. gmolina70@gmail.com
Gloria María
GM
Molina-Salinas
Jorge
J
Bórquez
Salvador
S
Said-Fernández
Luis Alberto
LA
Loyola
Alejandro
A
Yam-Puc
Pola
P
Becerril-Montes
Fabiola
F
Escalante-Erosa
Luis Manuel
LM
Peña-Rodríguez
D000478:Alkylation; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D019661:Apiaceae / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D004351:Drug Resistance; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D010936:Plant Extracts / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*
C551169:13 hydroxy-mulin-11-en-20-oic acid n-propyl ester; D000995:Antitubercular Agents; D004224:Diterpenes; D010936:Plant Extracts; C551171:isomulinic acid n-butyl ester; C551170:isomulinic acid n-propyl ester