The present study was aimed at evaluating the antibacterial activity of mulinane and azorellane diterpenes isolated from the Andean plants Azorella compacta and A. trifoliolata and semisynthetic derivatives against reference and multidrug-resistant strains. The results revealed that the semisynthetic compound 7-acetoxy-mulin-9,12-diene (5) exhibited antibacterial activity against reference and multidrug-resistant strains of Staphylococcus aureus and moderate antimycobacterial activity against Mycobacterium smegmatis ATCC 14468.
LoyolaL.A., MoralesG., RodriguezB., Jimenez-BarberoJ., DelatorreM.C., PeralesA., TorresM.R. (1990) Mulinic and isomulinic acids - rearranged diterpenes with a new carbon skeleton from Mulinum crassifolium.Tetrahedron, 46, 5413–5420.
2.
Molina-SalinasG., BorquezJ., ArdilesA., Said-FernandezS., LoyolaL., Yam-PucA., Becerril-MontesP., Escalante-ErosaF., San-MartínA., Gonzalez-ColladoI., Pena-RodriguezL. (2010) Bioactive metabolites from the Andean flora. Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids. Phytochemistry Reviews, 9, 271–278.
3.
(a) LoyolaL., BorquezJ., MoralesG., San-MartínA., ManriquezV., WittkeO. (1998) Azorellanol: A diterpenoid with a new carbon skeleton from Azorella compacta.Tetrahedron, 54, 15533–15540; (b) Astudillo L, Gutiérrez M, Quesada L, San-Martín A, Espinoza L, Peñailillo P. (2014) New diterpenes from Azorella spinosa. Natural Product Communications, 9, 9-12.
4.
LoyolaL., BorquezJ., MoralesG., ArayaJ., GonzalezJ., NeiraI., SaguaH., San-MartínA. (2001) Azorellane diterpenoids from Lareta acaulis, and its toxoplasmacidal activity. Boletin de la Sociedad Chilena de Quimica, 46, 9–13.
5.
LoyolaL., BorquezJ., MoralesG., ArayaJ., GonzalezJ., NeiraI., SaguaH., San-MartínA. (2001) Diterpenoids from Azorella yareta and their trichomonicidal activities. Phytochemistry, 56, 177–180.
Guzman-BlancoM., MejiaC., IsturizR., AlvarezC., BavestrelloL., GotuzzoE., LabarcaJ., LunaC., Rodriguez-NoriegaE., SallesM., ZuritaJ., SeasC. (2009) Epidemiology of methicillin-resistant Staphylococcus aureus (MRSA) in Latin America. International Journal of Antimicrobial Agents, 34, 304–308.
8.
DhedaK., GumboT., GandhiN.R., MurrayM., TheronG., UdwadiaZ., MiglioriG.B., WarrenR. (2014) Global control of tuberculosis: from extensively drug-resistant to untreatable tuberculosis. Lancet Respiratory Medicine, 2, 321–338.
9.
SatorresS., ChiaramelloA., MattanaC., AlcarazL., RossomandoP., TonnC., LaciarA. (2013) Azorella trifurcata and Mulinum echegarayii obtained from central region of Argentina: Antibacterial activity of their organic extracts. Emirates Journal of Food and Agriculture, 25, 457–462.
10.
LópezS., LimaB., AragónL., EspinarL.A., TapiaA., ZacchinoS., ZygadloJ., FeresinG.E., LópezM.L. (2012) Essential oil of Azorella cryptantha collected in two different locations from San Juan Province, Argentina: chemical variability and anti-insect and antimicrobial activities. Chemistry & Biodiversity, 9, 1452–1464.
11.
WachterG., MatooqG., HoffmannJ., MaieseW., SinghM., MontenegroG., TimmermannB. (1999) Antibacterial diterpenoid acids from Azorella compacta.Journal of Natural Products, 62, 1319–1321.
12.
BórquezJ., ArdilesA., LoyolaL.A., Peña-RodriguezL.M., Molina-SalinasG.M., VallejosJ., ColladoI.G., SimirgiotisM.J. (2014) Further mulinane and azorellane diterpenoids isolated from Mulinum crassifolium and Azorella compacta.Molecules, 19, 3898–3908.
13.
NewtonS., LauC., GurchaS., BesraG., WrightC. (2002) The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis.Journal of Ethnopharmacology, 79, 57–67.
14.
ChaturvediV., DwivediN., TripathiR., SinhaS. (2007) Evaluation of Mycobacterium smegmatis as a possible surrogate screen for selecting molecules active against multi-drug resistant Mycobacterium tuberculosis.Journal of General and Applied Microbiology, 53, 333–337.
15.
StephanJ., MailaenderC., EtienneG., DaffeM., NiederweisM. (2004) Multidrug resistance of a porin deletion mutant of Mycobacterium smegmatis.Antimicrobial Agents and Chemotherapy, 48, 4163–4170.
16.
Clinical, and Laboratory Standards Institute (CLSI). (2009) Performance standards for antimicrobial susceptibility testing. Approved standard M100-S19. 19th informational supplement. In Clinical and Laboratory Standards Institute.Wayne, PA.