Abdel-Malek S, Bastien JW, Mahler WF, Jia Q, Reinecke MG, Robinson WE Jr, Shu YH, Zalles-Asin J (1996) Drug leads from the Kallawaya herbalists of Bolivia. 1. Background, rationale, protocol and anti-HIV activity. J Ethnopharmacol 50:157–166. https://doi.org/10.1016/0378-8741(96)01380-3

Article  CAS  Google Scholar 

Araya JE, Neira I, Silva SD, Mortara RA, Manque P, Cordero E, Sagua H, Loyola A, Bórquez J, Morales G, González J (2003) Diterpenoids from Azorella compacta (Umbelliferae) active on Trypanosoma cruzi. Mem Inst Oswaldo Cruz 98:413–418. https://doi.org/10.1590/s0074-02762003000300022

Article  CAS  Google Scholar 

Areche C, Loyola LA, Borquez J, Rovirosa J, San-Martin A (2008) Microbial transformation of the diterpene mulin-11,13-dien-20-oic acid by Mucor plumbeus. Magn Reson Chem 46:765–768. https://doi.org/10.1002/mrc.2238

Article  CAS  Google Scholar 

Bórquez J, Bartolucci NL, Echiburú-Chau C, Winterhalter P, Vallejos J, Jerz G, Simirgiotis MJ (2016) Isolation of cytotoxic diterpenoids from the Chilean medicinal plant Azorella compacta Phil from the Atacama desert by high-speed counter-current chromatography. J Sci Food Agric 96:2832–2838. https://doi.org/10.1002/jsfa.7451

Article  CAS  Google Scholar 

De Carvalho CCCR, Da Fonseca MMR (2006) Biotransformation of terpenes. Biotechnol Adv 24:134–142. https://doi.org/10.1016/j.biotechadv.2005.08.004

Article  CAS  Google Scholar 

Delporte C, Backhouse N, Salinas P, San-Martín A, Bórquez J, Loyola A (2003) Pharmaco-toxicological study of diterpenoids. Bioorg Med Chem 11:1187–1190. https://doi.org/10.1016/s0968-0896(02)00645-4

Article  CAS  Google Scholar 

Dzul-Beh ADJ, Uc-Cachón AH, Bórquez J, Loyola LA, Peña-Rodríguez LM, Molina-Salinas GM (2020) Mulinane-and azorellane-type diterpenoids: a systematic review of their biosynthesis, chemistry, and pharmacology. Biomolecules 10:1333. https://doi.org/10.3390/biom10091333

Article  CAS  Google Scholar 

Fuentes NL, Sagua H, Morales G, Borquez J, Martin AS, Soto J, Loyola LA (2005) Experimental antihyperglycemic effect of diterpenoids of llareta Azorella compacta (Umbelliferae) Phil in rats. Phytother Res 19:713–716. https://doi.org/10.1002/ptr.1740

Article  CAS  Google Scholar 

Hegazy MEF, Mohamed TA, ElShamy AI, Mohamed AEHH, Mahalel UA, Reda EH, Shaheen AM, Tawfik WA, Shahat AA, Shams KA, Abdel-Azim NS, Hammouda FM (2015) Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: a review. J Adv Res 6:17–33. https://doi.org/10.1016/j.jare.2014.11.009

Article  CAS  Google Scholar 

Herrera-Canché SG, Sánchez-González M, Loyola LA, Bórquez J, García-Sosa K, Peña-Rodríguez LM (2020) Biotransformation of a mulinane diterpenoid by Aspergillus alliaceus and Mucor circinelloides. Biocatal Biotransformation 38:1–6. https://doi.org/10.1080/10242422.2019.1596083

Article  CAS  Google Scholar 

Loyola LA, Borquez J, Morales G, Araya J, Gonzalez J, Neira I, Sagua H, San-Martin A (2001) Azorellane diterpenoids from Laretia acaulis, and its toxoplasmacidal activity. Bol Soc Chil Quim 46:9–13. https://doi.org/10.4067/S0366-16442001000100003

Article  CAS  Google Scholar 

Marcos IS, Moro RF, Gil-Mesón A, Díez D (2016) 7-6-5 tricarboxylic diterpenes: valparanes, mulinanes, cyathanes, homoverrucosanes and relate ones. In Atta-ur-Rahman FRS (ed) Studies in Natural Products Chemistry, vol 48. Elsevier, Amsterdam, pp 137–208. https://doi.org/10.1016/B978-0-444-63602-7.00005-9

Martínez-González MA, Peña-Rodríguez LM, Uc-Cachón AH, Bórquez J, Simirgiotis MJ, Barrios-García HB, Hernández-Pando R, Loyola LA, Areche C, Dzul-Beh AJ, Barrios-Payán JA, Mata-Espinosa D, Escalante-Erosa F, García-Sosa K, Molina-Salinas GM (2021) Activity of semi-synthetic mulinanes against MDR, Pre-XDR, and XDR strains of Mycobacterium tuberculosis. Metabolites 11:876. https://doi.org/10.3390/metabo11120876

Article  CAS  Google Scholar 

Molina-Salinas GM, Bórquez J, Ardiles A, Said-Fernández S, Loyola LA, Yam-Puc A, Becerril-Montes P, Erosa-Escalante F, San-Martin A, González-Collado I, Peña-Rodríguez LM (2010) Bioactive metabolites from the Andean flora. Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids. Phytochem Rev 9:271–278. https://doi.org/10.1007/s11101-010-9162-4

Article  CAS  Google Scholar 

Mongelli E, Desmarchelier C, Coussio J, Ciccia G (1997) Biological studies of Bolax gummifera, a plant of the Falkland Islands used as a treatment of wounds. J Ethnopharmacol 56:117–121. https://doi.org/10.1016/s0378-8741(97)01516-x

Article  CAS  Google Scholar 

Morales P, Kong M, Pizarro E, Pasten C, Morales G, Borquez J, Loyola LA (2003) Effect of azorellanone, a diterpene from Azorella yareta Hauman, on human sperm physiology. J Androl 24:364–370. https://doi.org/10.1002/j.1939-4640.2003.tb02684.x

Article  Google Scholar 

Mutafova B, Mutafov S, Fernandes P, Berkov S (2016) Microbial transformations of plant origin compounds as a step in preparation of highly valuable pharmaceuticals. J Drug Metab Toxicol 7:204. https://doi.org/10.4172/2157-7609.1000204

Article  CAS  Google Scholar 

Neira I, Poblete L, Porcille P, Silva P, Araya J, Bórquez J, Morales G, Loyola LA, Sagua H (1998) Activity of diterpenoids isolated from Azorella compacta (Llareta) on Trypanosoma cruzi amastigotes. Bol Chil Parasitol 53:9–13

CAS  Google Scholar 

Rico-Martínez M, Medina FG, Marrero JG, Osegueda-Robles S (2014) Biotransformation of diterpenes. RSC Adv 4:10627-10647. https://doi.org/10.1039/C3RA45146A

Sepúlveda B, Quispe C, Simirgiotis M, García-Beltrán O, Areche C (2016) Gastroprotective effects of new diterpenoid derivatives from Azorella cuatrecasasii Mathias & Constance obtained using a β-cyclodextrin complex with microbial and chemical transformations. Bioorg Med Chem Lett 26:3220–3222. https://doi.org/10.1016/j.bmcl.2016.05.081

Article  CAS  Google Scholar 

Simoneit BR, Oros DR, Jaffé R, Didyk-Peña A, Areche C, Sepúlveda B, Didyk BM (2019) Mulinane and azorellane diterpenoid biomarkers by GC-MS from a representative Apiaceae (Umbelliferae) species of the Andes. Molecules 24:684. https://doi.org/10.3390/molecules24040684

Article  CAS  Google Scholar 

Wächter GA, Franzblau SG, Montenegro G, Suarez E, Fortunato RH, Saavedra E, Timmermann, N (1998) A new antitubercular mulinane diterpenoid from Azorella madreporica Clos. J Nat Prod 61:965-968. https://doi.org/10.1021/np980066w