Reynosin and santamarine: two sesquiterpene lactones from Ambrosia confertiflora with bactericidal activity against clinical strains of Mycobacterium tuberculosis

References

• Ahmed SM, Abdelgaleil SAM. 2005. Antifungal activity of extracts and sesquiterpene lactones from Magnolia grandiflora L. (Magnoliaceae). Int J Agr Biol. 7:638–642.
   Google Scholar
• Asaruddin MR, Honda G, Tsubouchi A, Nakajima-Shinada J, Aoki T, Kiuchi F. 2003. Trypanocidal constituents from Michelia alba. Nat Med. 57:61–63.
   Google Scholar
• Cantrell CL, Franzblau SG, Fischer NH. 2001. Antimycobacterial plant terpenoids. Planta Med. 67:685–694.
   PubMed Web of Science ®Google Scholar
• Choi HG, Lee DS, Li B, Choi YH, Lee SH, Kim YC. 2012. Santamarin, a sesquiterpene lactone isolated from Saussurea lappa, represses LPS-induced inflammatory responses via expression of heme oxygenase-1 in murine macrophage cells. Int Immunopharmacol. 13:271–279.
   PubMed Web of Science ®Google Scholar
• Coll P. 2009. Fármacos con actividad frente a Mycobacterium tuberculosis. Enferm Infecc Microbiol Clin. 27:474–480.
   PubMed Web of Science ®Google Scholar
• Collins LA, Franzblau SG. 1997. Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother. 41:1004–1009.
   PubMed Web of Science ®Google Scholar
• Copp BR. 2003. Antimycobacterial natural products. Nat Prod Rep. 20:535–557.
   PubMed Web of Science ®Google Scholar
• De la Torre RYC, Martínez EFR, Flores SAE, Waksman DTN, Salazar AR. 2013. Larvicidal and cytotoxic activities of extracts from 11 native plants from northeastern Mexico. J Med Entomol. 50:310–313.
   PubMed Web of Science ®Google Scholar
• Duraipandiyan V, Al HNA, Ignacimuthu S, Muthukumar C. 2012. Antimicrobial activity of sesquiterpene lactones isolated from traditional medicinal plant, Costus speciosus (Koen ex.Retz.) Sm. BMC Complement Altern Med. 12:13.
   PubMed Web of Science ®Google Scholar
• El-Alfy TS, Shehata AH, Koheil MA, Dahmy SA. 1989. Constituents of Anthemis melampodina growing in Egypt. Fitoterapia. 60:556–558.
   Google Scholar
• El-Feraly FS, Benigni DA. 1980. Sesquiterpene lactones of Laurus nobilis leaves. J Nat Prod. 43:527–531.
   Web of Science ®Google Scholar
• Fang F, Sang SM, Chen KY, Gosslau A, Ho CT, Rosen RT. 2005. Isolation and identification of cytotoxic compounds from Bay leaf (Laurus nobilis). Food Chem. 93:497–501.
   Web of Science ®Google Scholar
• Fischer NH, Lu T, Cantrell CL, Castañeda-Acosta J, Quijano L, Franzblau SG. 1998. Antimycobacterial evaluation of germacranolides in honour of Professor G.H. Neil Towers 75th birthday. Phytochemistry. 49:559–564.
   PubMed Web of Science ®Google Scholar
• Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, Hernandez A, Degnan MT, Cook MB, Quenzer VK, Ferguson RM. 1998. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol. 36:362–366.
   PubMed Web of Science ®Google Scholar
• ITIS. 2014. Integrated Taxonomic Information System [cited 2015 Jun 21]. Available from: http://www.itis.gov/servlet/SingleRpt/SingleRpt?search_topic=TSN&search_value =36522
   Google Scholar
• Johnson J, Moreno SF, López R. 1996. Compendio fitoquímico de la medicina tradicional herbolaria de Sonora. Sonora: Universidad de Sonora Press.
   Google Scholar
• Lawn SD, Wilkinson R. 2006. Extensively drug resistant tuberculosis. Br Med J. 333:559–560.
   PubMed Web of Science ®Google Scholar
• Lim S, Lee SJ, Nam KW, Kim KH, Mar W. 2013. Hepatoprotective effects of reynosin against thioacetamide-induced apoptosis in primary hepatocytes and mouse liver. Arch Pharm Res. 36:485–494.
   PubMed Web of Science ®Google Scholar
• Ma G, Chong L, Li Z, Cheung AH, Tattersall MH. 2009. Anticancer activities of sesquiterpene lactones from Cyathocline purpurea in vitro. Cancer Chemother Pharmacol. 64:143–152.
   PubMed Web of Science ®Google Scholar
• Macías FA, Galindo JCG, Castellano D, Velasco RF. 1999. Natural products as allelochemicals. 11. Sesquiterpene lactones with potential use as natural herbicide models (I): trans,trans-germacranolides. J Agric Food Chem. 47:4407–4414.
   PubMed Web of Science ®Google Scholar
• Maruthi PP, Suresh KC. 2013. Antimycobacterial drug design: homology modeling and docking studies on Mycobacterium tuberculosis alanine racemase. Drug Discov. 3:27–36.
   Google Scholar
• Molina-Salinas GM, Ramos MC, Vargas J, Mata-Cárdenas BD, Becerril-Montes P, Said-Fernández S. 2006. Bactericidal activity of organic extracts from Flourensia cernua DC against strains of Mycobacterium tuberculosis. Arch Med Res. 37:45–49.
   PubMed Web of Science ®Google Scholar
• Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 65:55–63.
   PubMed Web of Science ®Google Scholar
• Orme I, Secrist J, Anathan S, Kwong C, Maddry J, Reynolds R, Poffenberger A, Michael M, Miller L, Krahenbuh J, et al. 2001. Search for new drugs for treatment of tuberculosis. Tuberculosis drug screening program. Antimicrob Agents Chemother. 45:1943–1946.
   PubMed Web of Science ®Google Scholar
• Pan E, Gorka AP, Alumasa JN, Slebodnick C, Harinantenaina L, Brodie PJ, Roepe PD, Randrianaivo R, Birkinshaw C, Kingston DGI. 2011. Antiplasmodial and antiproliferative pseudoguaianolides of Athroisma proteiforme from the Madagascar dry forest. J Nat Prod. 74:2174–2180.
   PubMed Web of Science ®Google Scholar
• Picman AK. 1986. Biological activities of sesquiterpene lactones. Biochem Syst Ecol. 14:255–281.
   Web of Science ®Google Scholar
• Ramachandran G, Swaminathan S. 2015. Safety and tolerability profile of second-line anti-tuberculosis medications. Drug Saf. 38:253–269.
   PubMed Web of Science ®Google Scholar
• Rascón VLA, Jiménez EM, Velázquez CCA, Garibay EA, Medina JLA, Gámez MN, Robles ZRE. 2015. Antiproliferative and apoptotic activities of extracts of Asclepias subulata. Pharm Biol. 53:1741–1751.
   PubMed Web of Science ®Google Scholar
• Rivero A, Quintana J, Eiroa JL, López M, Triana J, Bermejo J, Estévez F. 2003. Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. Eur J Pharmacol. 482:77–84.
   PubMed Web of Science ®Google Scholar
• Robles RE, Coronado EW, Velazquez CA, Ruiz BE, Navarro NM, Garibay EA. 2013. In vitro anti-mycobacterial activity of nine medicinal plants used by ethnic groups in Sonora, Mexico. BMC Complement Altern Med. 13:329.
   PubMed Web of Science ®Google Scholar
• Robles RE, Velázquez CCA, Garibay EA, Gálvez RJC, Ruíz BE. 2011. Antimicrobial activity of Northwestern Mexican plants against Helicobacter pylori. J Med Food. 14:1280–1283.
   PubMed Web of Science ®Google Scholar
• Romo de Vivar A, Jiménez H. 1965. Structure of santamarine, a new sesquiterpene lactone. Tetrahedron. 21:1741–1745.
   Web of Science ®Google Scholar
• Salazar AR, Waksman MN, Flores SAE, de la Torre RYC. 2014. Use of Ambrosia confertiflora extracts as larvicide agents. Mex. Pat. Appl. MX 2012012779 A20140521.
   Google Scholar
• Scheepers JC, Malan SF, Du PJL, Van DS. 2011. The high performance liquid chromatography (HPLC) analysis of ultraviolet (UV) irradiated chlorophyll a and secondary plant compounds. Afr J Biotechnol. 10:16976–16985.
   Google Scholar
• Schmidt TJ, Nour AMM, Khalid SA, Kaiser M, Brun R. 2009. Quantitative structure – antiprotozoal activity relationships of sesquiterpene lactones. Molecules. 14:2062–2076.
   PubMed Web of Science ®Google Scholar
• Seaman FC. 1982. Sesquiterpene lactones as taxonomic characters in the Asteraceae. Bot Rev. 48:121–595.
   Web of Science ®Google Scholar
• Seaman FC, Mabry TJ. 1979. Sesquiterpene lactones and species relationships among the Shrubby Ambrosia Taxa. Biochem Syst Ecol. 7:105–114.
   Web of Science ®Google Scholar
• SEINet. Southwest Environmental Information Network. 2014. Ambrosia confertiflora [cited 2015 Jun 21]. Available from: http://swbiodiversity.org/seinet/taxa/index.php?taxon=Ambrosia confertiflora.
   Google Scholar
• Silva GL, Lee IS, Kinghorn AD. 1998. Special problems with the extraction of plants. In: Cannell RJP, editor. Natural products isolation. Methods in biotechnology. New Jersey: Humana Press. p. 340.
   Google Scholar
• Udwadia ZF, Amale RA, Ajbani KK, Rodrigues C. 2012. Totally drug-resistant tuberculosis in India. Clin Infect Dis. 54:579–581.
   PubMed Web of Science ®Google Scholar
• Ueyama M, Chikamatsu K, Aono A, Murase Y, Kuse N, Morimoto K, Kudoh S. 2014. Sub-speciation of Mycobacterium tuberculosis complex from tuberculosis patients in Japan. Tuberculosis. 94:15–19.
   PubMed Web of Science ®Google Scholar
• Valencia D, Alday E, Robles R, Garibay-Escobar A, Gálvez-Ruíz JC, Salas-Reyes M, Jiménez-Estrada M, Velázquez-Contreras E, Hernández J, Velázquez C. 2012. Seasonal effect on propolis chemical composition and biological activities of Sonoran propolis. Food Chem. 131:645–651.
   Web of Science ®Google Scholar
• Velayati AA, Masjedi MR, Farnia P, Tabarsi P, Ghanavi J, ZiaZarifi AH, Hoffner SE. 2009. Emergence of new forms of totally drug-resistant tuberculosis bacilli: super extensively drug-resistant tuberculosis or totally drug-resistant strains in Iran. Chest. 136:420–425.
   PubMed Web of Science ®Google Scholar
• WHO, World Health Organization. Global tuberculosis report 2012 [cited 2015 Jun 21]. Available from: http://apps.who.int/iris/bitstream/10665/75938/1/9789241564502_eng.pdf .
   Google Scholar
• WHO, World Health Organization. Global Tuberculosis Report 2014 [cited 2015 Jun 21]. Available from: http://apps.who.int/iris/bitstream/10665/137094/1/9789241564809_eng.pdf .
   Google Scholar
• Yoshioka H, Renold W, Fischer NH, Higo A, Mabry TJ. 1970. Sesquiterpene lactones from Ambrosia confertiflora (Compositae). Phytochemistry. 9:823–832.
   Web of Science ®Google Scholar