Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids

Fitoterapia

Volumn 81, Issue 1, 2010, Pages 50-54

  Molina Salinas, Gloria María ^a,b   Bórquez, Jorge ^c   Ardiles, Alejandro ^c   Said Fernández, Salvador ^b   Loyola, Luis Alberto ^c   San Martín, Aurelio ^d   González Collado, Isidro ^e   Peña Rodríguez, Luis Manuel ^a  

^a CENTRO DE INVESTIGACIÓN CIENTÍFICA DE YUCATÁN   (Mexico)

^b INSTITUTO MEXICANO DEL SEGURO SOCIAL   (Mexico)

^c Facultad de Ciencias   (Chile)

^d UNIVERSITY OF CHILE   (Chile)

^e UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

Apiaceae; Azorella spp; Azorellane; Mulinane; Mulinum spp; Mycobacterium tuberculosis

Indexed keywords

13 EPI AZORELLANOL; 13 HYDROXY MULIN 11 EN 20 OIC ACID METHYL ESTER; 13,14 DIHYDROXY MULINIC 11 EN 20 OIC ACID; 13,20 DIHYDROXYMULIN 11 EN; 13BETA HYDROXY AZORELLANONE; 17 ACETOXY 13ALPHA HYDROXY AZORELLANE; 17 ACETOXY MULINIC ACID; 17 ACETOXY MULINIC ACID METHYL ESTER; 7 ACETOXY MULIN 9,12 DIENE; 7 DEACETYL AZORELLANOL; AZORELLANE DITERPENOID; AZORELLANOL; AZORELLANONE; ETHAMBUTOL; HERBACEOUS AGENT; ISONIAZID; MULIN 11,13 DIEN 20 OIC ACID METHYL ESTER; MULINANE DITERPENOID; MULINENIC ACID; MULINENIC ACID METHYL ESTER; MULINIC ACID; OFLOXACIN; PYRAZINAMIDE; RIFAMPICIN; STREPTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; YARETOL;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ANTITUBERCULOSIS ACTIVITY; ARTICLE; AZORELLA COMPACTA; AZORELLA MADREPORICA; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG ISOLATION; DRUG POTENCY; IN VITRO STUDY; LARETIA ACAULIS; MEDICINAL PLANT; MINIMUM INHIBITORY CONCENTRATION; MULINUM CRASSIFOLIUM; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL;

ANTITUBERCULAR AGENTS; APIACEAE; DITERPENES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PLANT EXTRACTS;

APIACEAE; AZORELLA; AZORELLA COMPACTA; AZORELLA MADREPORICA; LARETIA ACAULIS; MULINUM; MULINUM CRASSIFOLIUM; MYCOBACTERIUM TUBERCULOSIS;

EID: 70449709053     PISSN: 0367326X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fitote.2009.07.005     Document Type: Article

References (23)

1. Neira I., Pobleta L., Porcille P., Silva P., Araya J., Bórquez J., Morales G., Loyola L.A., and Sagua H. Activity of diterpenoids isolated from Azorella compacta (Llareta) on Trypanosoma cruzi amastigotes. Bol Chil Parasitol 53 (1998) 9-13
2. Loyola L.A., Borquez J., Morales G., Araya J., Gonzalez J., Neira I., Sagua H., and San-Martín A. Diterpenoids from Azorella yareta and their trichomonicidal activities. Phytochemistry 56 (2001) 177-180
3. Loyola L.A., Borquez J., Morales G., Araya J., Gonzalez J., Neira I., Sagua H., and San Martin A. Azorellane diterpenoids from Laretia acaulis and its toxoplamacidal activity. Bol Soc Chil Quím 46 (2001) 9-13
4. Loyola L.A., Borquez J., Morales G., San-Martin A., Darias J., Flores N., and Gimenez A. Muliane-type diterpenoids from Azorella compacta display antiplasmodial activity. Phytochemistry 65 (2004) 1931-1935
5. Wächter G.A., Matooq G., Hoffmann J.J., Maiese W.M., Singh M.P., Montenegro G., and Timmermann B.N. Antibacterial diterpenoid acids from Azorella madreporica. J Nat Prod 62 (1999) 1319-1321
6. Abdel-Malek S., Bastien J.W., Mahler W.F., Jia Q., Reinecke M.G., Robinson Jr. W.E., et al. Drug leads from the Kallawaya herbalists of Bolivia. Background, rationale, protocol and anti-HIV activity. J Ethopharmacol 50 (1996) 157-166
7. Morales P., Kong M., Pizarro E., Pasten C., Morales G., Borquez J., et al. Effect of azorellanone, a diterpene from Azorella yareta Hauman on human sperm physiology. J Androl 24 (2003) 364-370
8. Mongelli E., Desmarchelier C., Coussio J., and Ciccia G. Biological studies of Bolax gummifera, a plant of the Falkland Islands used as a treatment of wounds. J Ethnopharmacol 56 (1997) 117-121
9. Mongelli E., Pampero S., Coussio J., Salomon H., and Ciccia G. Cytotoxic and DNA interaction activities of extracts from medical plants used in Argentina. J Ethnopharmacol. 71 (2000) 145-151
10. Fuentes N.L., Sagua H., Morales G., Borquez J., San-Martín A., Soto J., et al. Experimental antihyperglycemic effect of diterpenoids of llareta Azorella compacta (Umbelliferae) Phil in rats. Phytother Res 19 (2005) 713-716
11. Delporte C., Backhouse N., Salinas P., San-Martin A., and Borquez J. Pharmaco-toxicological study of diterpenoids. Bioorg Med Chem 11 (2003) 1187-1190
12. Borquez J., Loyola L.A., Morales G., San-Martín A., Roldan R., Marquez N., et al. Azorellane diterpenoids from Laretia acaulis inhibit nuclear factor-kappa B activity. Phytother Res 21 (2007) 1082-1086
13. Wächter G.A., Franzblau S.G., Montenegro G., Suarez E., Fortunato R.H., Saavedra E., et al. Timmermann, a new antitubercular mulinane diterpenoid from Azorella madreporica Clos. J Nat Prod 61 (1998) 965-968
14. Loyola L.A., Bórquez J., Morales G., San-Martín A., and Manríquez V. O Wittke, Azorellanol: a diterpenoid with a new carbon skeleton from Azorella compacta. Tetrahedron 54 (1998) 15533-15540
15. Bórquez J, Molina-Salinas GM, Loyola LA, San-Martín A, Peña-Rodríguez LM, Said-Fernández S. A new azorellane diterpenoid from Azorella madreporica, J Brazil Chem Soc Submitted.
16. Loyola L.A., Bórquez J., Morales G., San Martín A., Manríquez V., Boys D., et al. Yaretol, a norditerpenoid from Azorella madreporica. J Nat Prod 65 (2002) 1678-1680
17. Loyola L.A., Bórquez J., Morales G., and San Martín A. Mulinolic acid, a diterpenoid from Mulinum crassifolium. Phytochemistry 43 (1996) 165-168
18. Loyola L.A., Bórquez J., Morales G., and San Martín A. Diterpenoids from Azorella compacta. Phytochemistry 44 (1997) 649-651
19. Loyola L.A., Morales G., Rodriguez B., Jimenez-Barbero J., de la Torre M.C., Perales A., et al. Mulinic and isomulinic acids. Rearranged diterpenes with a new skeleton from Mulinum crassifolium. Tetrahedron 46 (1990) 5413-5420
20. Loyola L.A., Morales G., De la Torre M.C., Pedreros S., and Rodríguez B. 17-acetoxymulinic acid, a rearranged diterpenoid from Mulinum crassifolium. Phytochemistry 29 (1990) 3950-3951
21. Loyola L.A., Bórquez J., Morales G., and San Martín A. Mulinol, a diterpenoid from Azorella compacta. Phytochemistry 45 (1997) 1465-1467
22. Loyola L.A., Morales G., Rodríguez B., Jiménez-Barbero J., Pedreros S., de la Torres M.C., et al. Mulinenic acid, a rearranged diterpenoid from Mulinum crassifolium. J Nat Prod 54 (1991) 1404-1408
23. . Mycobacterium tuberculosis. Arch Med Res 37 (2006) 45-49