Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Steichen, D. S. in Handbook of Applied Surface and Colloid Chemistry (ed. Holmberg, K. 310–347 John Wiley & Sons, Ltd., New York, (2002).
Walker, E. B. & Paulson, D. Quaternary Ammonium Compounds, Marcel Dekker, New York, (2002).
Guani-Guerra, E., Santos-Mendoza, T., Lugo-Reyes, S. O. & Teran, L. M. Antimicrobial peptides: general overview and clinical implications in human health and disease. Clin. Immun. 135, 1–11 (2010).
Rochfort, S. J. et al. Latifolians A and B, novel JNK3 kinase inhibitors from the papua new guinean plant Gnetum latifolium. J. Nat. Prod. 68, 1080–1082 (2005).
Martin, F. et al. Alkaloids from the Chinese Vine Gnetum montanum. J. Nat. Prod. 74, 2425–2430 (2011).
Čerňáková, M. & Košťálová, D. Antimicrobial activity of berberine—a constituent of Mahonia aquifolium. Folia Microbiol. 47, 375–378 (2002).
Wabo, H. K. et al. Tabouensinium chloride, a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis. Nat. Prod. Res. 19, 591–595 (2005).
Kozlovsky, A. G., Zhelifonova, V. P. & Antipova, T. V. The fungus Penicillium citrinum, isolated from permafrost sediments, as a producer of ergot alkloids and new quinoline alkalods quinocitrinines. Appl. Biochem. Microbiol 41, 499–502 (2005).
Hertiani, T. et al. From anti-biofouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian Agelas sponges. Bioorg. Med. Chem. 18, 1297–1311 (2010).
Park, C. H. et al. Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. Planta Med. 62, 405–409 (1996).
Jennings, M. C., Minbiole, K. P. C. & Wuest, W. M. Quaternary ammonium compounds: an antimicrobial mainstay and platform for innovation to address bacterial resistance. ACS Infect. Dis 1, 288–303 (2015).
Palomo, C., Oiarbide, M. & López, R. Asymmetric organocatalysis by chiral Bronsted bases: implications and applications. Chem. Soc. Rev. 38, 632–653 (2009).
Lv, J., Qian, Y., Liu, T. & Wang, Y. Synthesis and evaluation of amphiphilic cationic quinine-derived for antibacterial activity against methicillin-resistance Staphylococcus aureus. Bioorg. Med. Chem. Lett. 17, 4102–4106 (2007).
Coates, W. J. et al. The antimicrobial activity of Q-7,0 appeared in a patent. Preparation of piperidinylalkylquinolines as antibacterials. WO 9937635 (1999).
Shibagaki, M. et al. The selectivity in N-alkylation of nicotine. Heterocycles 19, 1641–1645 (1982).
Baidya, M., Horn, M., Zipse, H. & Mayr, H. Organocatalytic activity of cinchona alkaloids: which nitrogren is more nucleophilic? J. Org. Chem. 74, 7157–7164 (2009).
Crooks, P. A., Dwoshin, L., Xu, R. & Ayers, J. Chain-modified pyridine-N substituted nicotine compounds for use in the treatment of CNS pathologies. US Pat. Appl. Publ. 20030225142 (2003).
Crooks, P. A. et al. Development of subtype-selective ligands as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release. Bioorg. Med. Chem. Lett. 14, 1869–1874 (2004).
Singh, P. & Arora, G. Organic synthesis under PTC: part 6—preparation and decomposition of chiral phase transfer catalysts derived from quinine. Indian J. Chem. Sect. B 25B, 1034–1037 (1986).
Gavrilov, K. N., Mikhel, I. S., Lechkin, D. V. & Timofeeva, G. I. Quinine-based dioxaphospholane with N-decylquinuclidine fragment. Phosphorus Sulfur Silicon Relat. Elem. 108, 285–287 (1996).
Acknowledgements
This work was funded by a University City Science Center QED Proof of Concept Grant (Grant S1403 to WMW), as well as by Temple and Villanova Universities. MCJ acknowledges a National Science Foundation Pre-Doctoral Fellowship (DGE1144462). The authors thank CW Ross (Temple Mass Spectrometry Facility) for obtaining MS data.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Competing interests
The authors declare no conflict of interest.
Additional information
Supplementary Information accompanies the paper on The Journal of Antibiotics website
Supplementary information
Rights and permissions
About this article
Cite this article
Joyce, M., Jennings, M., Santiago, C. et al. Natural product-derived quaternary ammonium compounds with potent antimicrobial activity. J Antibiot 69, 344–347 (2016). https://doi.org/10.1038/ja.2015.107
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/ja.2015.107
This article is cited by
-
Synthesis and characterization of bio-based quaternary ammonium salts with gibberellate or l-tryptophanate anion
Monatshefte für Chemie - Chemical Monthly (2020)
