A series of D-glucosamine derivatives were synthesized (2–4) and evaluated for their antimicrobial activity. Some of the compounds investigated have shown significant antimicrobial activity against Gram-positive and Gram-negative bacterial strains as well as a few fungal strains. The results suggest that the presence of sugar moiety is necessary to biological activity. 1. Introduction Carbohydrates are the most abundant class of biomolecules, making up 75% of the biomass on Earth [1]. Carbohydrates are used to store energy but also perform other important functions to life [2]. Recently, carbohydrates and their derivatives have emerged as an important tool for stereoselective synthesis and as a chiral pool for the design of chiral ligands. They are used as chiral building blocks, precursors for drug synthesis and chiral catalysts in asymmetric catalysis [3–8]. Despite the importance of carbohydrates in biological events, the pace of development of carbohydrate based therapeutics has been relatively slow. This is mainly due to practical synthetic and analytical difficulty. Recent advances in the field, however, have demonstrated that many of these problems can be circumvented and evidence the importance of carbohydrates as bioactive substances, with regard to antibacterial, antiviral, antineoplastic, antiprotozoal, and antifungal activity among others, related recently in literature [9, 10]. On the other hand, imines or Schiff bases are easily generated by condensation of carbonyl groups and primary amines. In carbohydrate chemistry, a large number of imines have been reported, both by reaction of sugar aldehydes with amines and by reaction of aminosugars with aldehydes [11–16]. Schiff bases and their metal complexes have several applications as catalysts in oxygenations, hydrolysis, and other reactions, antimicrobial and antiviral activities, among other applications [15–17]. Preparation of 4-anisaldehyde and cinnamaldehyde glucosamine imines and their acetylated derivatives is usually used as a convenient strategy for selective protecting of the amino group of the aminosugar [11, 18, 19]. Recent studies have shown that Schiff bases derived from glucosamine have antifungal [20] and antibacterial activity [21]. On the other hand, aldehydes present in essential oils may also have action against different microorganisms. Cinnamaldehyde, the main component of Cinnamomum zeylanicum essential oil, specie of Lauraceae family, has several activities such as antioxidant, antibacterial, and antifungal [22]. This field has been explored by our research group and
References
[1]
V. F. Ferreira, D. R. da Rocha, and F. De Carvalho Da Silva, “Potentiality and opportunity in chemistry of sucrose and other sugars,” Quimica Nova, vol. 32, no. 3, pp. 623–638, 2009.
[2]
R. V. Stick, Carbohydrates: The Sweet Molecules of Life, Academic Press, 2001.
[3]
M. Diéguez, O. Pàmies, A. Ruiz, Y. Díaz, S. Castillón, and C. Claver, “Carbohydrate derivative ligands in asymmetric catalysis,” Coordination Chemistry Reviews, vol. 248, pp. 2165–2192, 2004.
[4]
M. Diéguez, O. Pàmies, and C. Claver, “Ligands derived from carbohydrates for asymmetric catalysis,” Chemical Reviews, vol. 104, no. 6, pp. 3189–3216, 2004.
[5]
S. Woodward, M. Diéguez, and O. Pàmies, “Use of sugar-based ligands in selective catalysis: recent developments,” Coordination Chemistry Reviews, vol. 254, pp. 2007–2030, 2010.
[6]
M. Diéguez, C. Claver, and O. Pàmies, “Recent progress in asymmetric catalysis using chiral carbohydrate-based ligands,” European Journal of Organic Chemistry, vol. 2007, no. 28, pp. 4621–4634, 2007.
[7]
M. M. K. Boysen, “Carbohydrates as synthetic tools in organic chemistry,” Chemistry, vol. 13, no. 31, pp. 8648–8659, 2007.
[8]
H. R. Appelt, J. B. Limberger, M. Weber et al., “Carbohydrates in asymmetric synthesis: enantioselective allylation of aldehydes,” Tetrahedron Letters, vol. 49, no. 33, pp. 4956–4957, 2008.
[9]
C. M. Nogueira, B. R. Parmanhan, P. P. Farias, and A. G. Corrêa, “A importancia crescente dos carboidratos em química medicinal,” Revista Virtual de Química, vol. 1, no. 2, p. 149, 2009.
[10]
C.-H. Wong, Ed., Carbohydrate-Based Drug Discovery, Wiley-VCH, Weinheim, Germany, 2003.
[11]
M. Bergmann and L. Zervas, “Synthesen mit glucosamin,” Berichte der Deutschen Chemischen Gesellschaft, vol. 64, no. 5, pp. 975–980, 1931.
[12]
Z. E. Jolles and W. T. Morgan, “The isolation of small quantities of glucosamine and chondrosamine,” Biochemical Journal, vol. 34, no. 8-9, pp. 1183–1190, 1940.
[13]
A. N. Bedekar, A. N. Naik, and A. C. Pise, “Schiff base derivatives of 2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose,” Asian Journal of Chemistry, vol. 21, no. 9, pp. 6661–6666, 2009.
[14]
E. M. S. Pérez, M. ávalos, R. Babiano et al., “Schiff bases from d-glucosamine and aliphatic ketones,” Carbohydrate Research, vol. 345, pp. 23–32, 2010.
[15]
J. Costamagna, L. E. Lillo, B. Matsuhiro, M. D. Noseda, and M. Villagrán, “Ni(II) complexes with Schiff bases derived from amino sugars,” Carbohydrate Research, vol. 338, no. 15, pp. 1535–1542, 2003.
[16]
J. Costamagna, N. P. Barroso, B. Matsuhiro, and M. Villagrán, “Copper(II) complexes with aminosugar derived Schiff bases as ligands,” Inorganica Chimica Acta, vol. 273, no. 1-2, pp. 191–195, 1998.
[17]
S. Kumar, D. N. Dhar, and P. N. Saxena, “Applications of metal complexes of Schiff bases—a review,” Journal of Scientific and Industrial Research, vol. 68, pp. 181–187, 2009.
[18]
G. Chauvière, B. Bouteille, B. Enanga, et al., “Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead,” Journal of Medicinal Chemistry, vol. 46, pp. 427–440, 2003.
[19]
M. ávalos, R. Babiano, P. Cintas, et al., “Synthesis of sugar isocyanates and their application to the formation of ureido-linked disaccharides,” European Journal of Organic Chemistry, vol. 3, pp. 657–671, 2006.
[20]
Y. Xue-Qiong, H. Jian, Y. Chang-Jiang, L. Fang, and L. Qiang, “Synthesis and antifungal activity of D-glucosamine Schiff base,” Chemical Reagents, vol. 32, no. 11, pp. 961–964, 2010.
[21]
L. Shurong, J. Shuxing, X. Yang, and L. Pu, “Detection of antibacterial activity of some new Schiffbase derivative,” Journal of Zhengzhou University Medical Sciences, no. 4, pp. 787–789, 2008.
[22]
H. B. Singh, M. Srivastava, A. B. Singh, and A. K. Srivastava, “Cinnamon bark oil, a potent fungitoxicant against fungi causing respiratory tract mycoses,” Allergy, vol. 50, no. 12, pp. 995–999, 1995.
[23]
E. Margery Linday, Practical Introduction to Microbiology, E & FN Spon, London, UK, 1962.
[24]
C. Perez, M. Paul, and P. Bazerque, “An antibiotic assay by the agar well-diffusion method,” Acta Biologiae et Medicine Experimentalis, vol. 15, pp. 113–115, 1990.
[25]
D. Kalemba and A. Kunicka, “Antibacterial and antifungal properties of essential oils,” Current Medicinal Chemistry, vol. 10, no. 10, pp. 813–829, 2003.
[26]
E. A. Bancroft, “Antimicrobial resistance: it's not just for hospitals,” The Journal of the American Medical Association, vol. 298, no. 15, pp. 1803–1804, 2007.
[27]
R. M. Klevens, M. A. Morrison, J. Nadle et al., “Invasive methicillin-resistant Staphylococcus aureus infections in the United States,” The Journal of the American Medical Association, vol. 298, no. 15, pp. 1763–1771, 2007.
[28]
K. Bush, “Alarming β-lactamase-mediated resistance in multidrug-resistant Enterobacteriaceae,” Current Opinion in Microbiology, vol. 13, no. 5, pp. 558–564, 2010.
