Chitin: A Structural Biopolysaccharide with Multiple Applications

Abstract

Chitin is a naturally occurring fibre‐forming polymer that plays a protective role in many lower eukaryotes similar to that of cellulose in plants. Chemically it is a long‐chain unbranched polysaccharide made of N‐acetylglucosamine residues linked through β‐1,4 covalent bonds; it is the second most abundant organic compound in nature, after cellulose. Taking into account the role played by chitin in different biological structures (i.e. fungal cell walls, insect peritrophic matrix, insect and crustacean cuticles, eggshells from nematodes, cyst wall of protozoa), its metabolism (biosynthesis and degradation) is essential for different morphogenetic events. Absent in vertebrates and plants, chitin participates in host–parasite interactions and represents a parasite‐specific target for chemotherapeutic attack and also plays a role in host immune responses. Because of its abundance in nature and its properties, biotechnological applications of chitin derivatives, such as chitosan and chito‐oligosaccharides, are currently an expanding area in biomedicine, pharmaceutical and food technology and agro‐biosciences.

Key Concepts:

  • Chitin is a long‐chain unbranched polysaccharide made of β‐1,4‐linked anhydro‐2‐acetamido‐2‐deoxy‐d‐glucose (GlcNAc) which forms crystalline fibrillar structures following association of adjacent chains through hydrogen bonds between the N–H and the CO groups.

  • Nascent chitin is a growing chitin chain which is being synthesised by the chitin synthase and it represents a good substrate for chitinolytic enzymes.

  • Microfibrillar chitin is a crystalline structure formed by chains of the polysaccharide which associate through hydrogen bonds between adjacent chains and it is responsible for the physico‐chemical properties of the polymer.

  • The fungal cell wall is a supramolecular network outside the plasma membrane, formed by structural polysaccharides, including chitin, and proteins and glycoproteins, that protects the fungal cell and determines morphology, similarly to cuticle (exosqueleton) in insects.

  • Insect cuticle (exosqueleton) is an extracellular matrix covering the epidermis and trachea, composed mainly by chitin (and proteins), which protects the animal and confers morphology.

  • The peritrophic membrane (matrix) is an extracellular layer that covers the midgut in most arthropods and it is made of chitin, proteins and proteoglycans, and provides protection to the underlaying digestive cells.

  • Chitin biosynthesis is a strongly regulated process, both spatially and temporally, as chitin deposition is essential for fungal growth and development (moulting) in arthropods. Chitin synthases are membrane bound enzymes that incorporate the substrate (UDP‐N‐acetylglucosamine) from the cytosol to the nascent chitin chain that is extruded outside the membrane.

  • Chitinases are chitin‐hydrolysing enzymes that play important roles in the physiology of chitin‐containing eukaryotes, and chitinolytic bacteria are active in a scavenging role by degrading massive amounts of chitin in marine and soil biomass, avoiding its accumulation and favouring the utilisation of chitin as a renewable source.

  • The absence of chitin in vertebrates and plants makes the chitin metabolism a potentially useful parasite‐specific target for chemotherapeutic attack. In mammals, chitin regulates immune responses playing a role in inflammation, and allergic diseases. In plants, chitin elicits defence responses, and in leguminous plants, chitin oligosaccharides produced by rhizobia promote plant nodulation.

  • Owing to their abundance in nature and properties, chitin, chitosan and their derivatives have gained potential interest for a wide range of areas, including biopharmaceutical and biomedical applications.

Keywords: polysaccharide; chitosan; chitinase; chitin synthetase

Figure 1.

Chemical structures of the repeating units of idealised chitin, chitosan and cellulose.

Figure 2.

Orientation of the molecular chains in α‐, β‐ and γ‐chitin.

Figure 3.

General pathway of chitin biosynthesis in biological systems.

Figure 4.

Electron microscopic observation of chitin microfibrils (arrowheads) synthesised in vitro after proteolytic activation with trypsin of a chitosomal (see text) zymogenic chitin synthetase preparation obtained from a fungal species (Candida albicans), bar, 100 nm.

Figure 5.

Chemical structures of some inhibitors of chitin metabolism. (a) Polyoxin D, (b) nikkomycins, (c) benzoylphenylurea derivative and (d) allosamidin.

close

References

Adrangi S and Faramarzi MA (2013) From bacteria to human: a journey into the world of chitinases. Biotechnology Advances 31: 1786–1795.

Aguilar‐Díaz H, Carreero JC, Argüello‐García R, Laclette JP and Morales‐Montoro J (2011) Cyst and encystment in protozoan parasites: optimal targets for new life‐cycle interrupting strategies? Trends in Parasitology 27: 450–458.

Arakane Y and Muthukrishnan S (2010) Insect chitinase and chitinase‐like proteins. Cellular and Molecular Life Sciences 67: 201–216.

Arakane Y, Taira T, Ohnuma T and Fukamizo T (2012) Chitin-related enzymes in agro-biosciences. Current Drug Targets 13: 442–470.

Bhattacharya D, Nagpure A and Gupta RK (2007) Bacterial chitinases: properties and potential. Critical Reviews in Biotechnology 27: 21–28.

Bo M, Bavestrello G, Kurek D et al. (2012) Isolation and identification of chitin in the black coral Parantipathes larix (Anthozoa: Cnidaria). International Journal of Biological Macromolecules 51: 129–137.

Brinchmann BC, Bayat M, Brogger T et al. (2011) A possible role of chitin in the pathogenesis of asthma and allergy. Annals of Agricultural and Environmental Medicine 18: 7–12.

Chaudhary PM, Tupe SG and Deshpande MV (2013) Chitin synthase inhibitors as antifungal agents. Mini‐Reviews in Medicinal Chemistry 13: 222–236.

Cohen E (2001) Chitin synthesis and inhibition: a revisit. Pesticide Management Science 57: 946–950.

D'Haeze W and Holsters M (2002) Nod factors structures, responses, and perception during initiation of nodule development. Glycobiology 12: 79R–105R.

Dutta J, Tripathi S and Dutta PK (2012) Progress in antimicrobial activities of chitin, chitosan and its oligosaccharides: a systematic study needs for food applications. Food Science and Technology International 18: 3–34.

Eijsink V, Hoell I and Vaaje‐Kolstada G (2010) Structure and function of enzymes acting on chitin and chitosan. Biotechnology and Genetic Engineering Reviews 27: 331–366.

Foster JM, Zang Y, Kumar S and Carlow CK (2005) Parasitic nematodes have two distinct chitin synthases. Molecular and Biochemical Parasitology 142: 126–132.

Free SJ (2013) Fungal cell wall organization and biosynthesis. Advances in Genetics 81: 33–82.

Hamel LP and Beaudoin N (2010) Chito‐oligosaccharide sensing and downstream signaling: contrasted outcomes in pathogenic and beneficial plant‐microbe interactions. Planta 232: 787–806.

Hartl L, Zach S and Seidl‐Seiboth V (2012) Fungal chitinases: diversity, mechanistic properties and biotechnological potential. Applied Microbiology and Biotechnology 93: 533–543.

Huang CJ, Beasley KN, Acevedo EO et al. (2014) Chitin enhances obese inflammation ex vivo. Human Immunology 75: 41–46.

Jang MK, Kong BG, Jeong YI, Lee CH and Nah JW (2004) Physicochemical characterization of α‐chitin, β‐chitin, and γ‐chitin separated from natural resources. Journal of Polymer Science Part A: Polymer Chemistry 42: 3423–3432.

Jarmila V and Vavriková E (2011) Chitosan derivatives with antimicrobial, antitumour and anti‐oxidant activities, a review. Current Pharmaceutical Design 17: 3596–3607.

Kasprzewska A (2003) Plant chitinases: regulation and function. Cell and Molecular Biology Letters 8: 809–824.

Khoushab F and Yamabhai M (2010) Chitin research revisited. Marine Drugs 8: 1988–2012.

Kneipp LF, Andrade AFB, de Souza W et al. (1998) Trichomonas vaginalis and Tritrichomonas foetus: expression of chitin at the cell surface. Experimental Parasitology 89: 195–204.

Kombrink A, Sánchez‐Vallet A and Thomma BP (2011) The role of chitin detection in plant‐pathogen interactions. Microbes and Infection 13: 1168–1176.

Kumar MN, Muzzarelli RA, Muzzarelli C, Sashiwa H and Domb AJ (2004) Chitosan chemistry and pharmaceutical perspectives. Chemistry Reviews 104: 6017–6084.

Kurita K (2006) Chitin and chitosan: functional biopolymers from marine crustaceans. Marine Biotechnology 8: 203–226.

Lee CG (2009) Chitin, chitinases and chitinase‐like proteins in allergic inflammation and tissue remodeling. Yonsei Medical Journal 50: 22–30.

Lee CG, Da Silva CA, De la Cruz CS et al. (2011) Role of chitin and chitinase/chitinase‐like proteins in inflammation, tissue remodeling, and injury. Annual Review of Physiology 73: 479–501.

Lee CG, Da Silva CA, Lee JY, Hartl D and Elias JA (2008) Chitin regulation of immune responses: an old molecule with new roles. Current Opinion in Immunology 20: 684–689.

Martínez JP and Gozalbo D (1994) Chitin synthetases in Candida albicans: a review on their subcellular distribution and biological function. Microbiologia SEM 10: 239–248.

Merzendorfer H (2011) The cellular basis of chitin synthesis in fungi and insects: common principles and differences. European Journal of Cell Biology 90: 759–769.

Muzzarelli RA, Jenieux R and Gooday GW (1986) Chitin in Nature and Technology. New York, NY: Plenum Press.

Nagasawa H (2012) The crustacean cuticle: structure, composition and mineralization. Frontiers in Bioscience 4: 711–720.

Nishimura S, Nishi N, Tokura S, Nishimura K and Azuma I (1984) Immunological activity of chitin and its derivatives. Vaccine 2: 93–99.

Prabaharan M (2008) Review paper: chitosan derivatives as promising materials for controlled drug delivery. Journal of Biomaterials Applications 23: 5–36.

Ruiz‐Herrera J and Ortíz‐Castellanos L (2010) Analysis of the genetic relationships and evolution of the cell walls from yeasts and fungi. FEMS Yeast Research 10: 225–243.

Ruiz‐Herrera J and San Blas G (2003) Chitin synthesis as target for antifungal drugs. Current Drug Targets: Infectious Disorders 3: 77–91.

Ruiz‐Herrera J, Sentandreu R and Martínez JP (1992) Chitin biosynthesis in fungi. In: Arora DK, Elander RP and Mukerji KG (eds) Handbook of Applied Mycology. Fungal Biotechnology, pp. 281–312. New York, NY: Marcel Dekker.

Saranya N, Moorthi A, Saravanan S, Devi MP and Selvamurugan N (2011) Chitosan and its derivatives for gene delivery. International Journal of Biological Macromolecules 48: 234–238.

Snaar‐Jagalska BE, Krens SFG, Robina I, Wang LX and Spaink HP (2003) Specific activation of ERK pathways by chitin oligosaccharides in embrionic zebrafish cell lines. Glycobiology 13: 725–733.

Sobotnik J, Kudlikova‐Krizkova I, Vancova M, Munzbergova Z and Hubert J (2008) Chitin in the peritrophic membrane of Acarus siro (Acari: Acaridae) as a target for novel acaricides. Journal of Economic Entomology 101: 1028–1033.

Spindler KD, Spindler‐Barth M and Londershausen M (1990) Chitin metabolism: a target for drugs against parasites. Parasitology Research 76: 283–288.

Vogan CL, Powell A and Rowley AF (2008) Shell disease in crustaceans: just chitin recycling gone wrong? Environmental Microbiology 10: 826–835.

Wan ACA and Tai BCU (2013) Chitin, a promising biomaterial for tissue engineering and stem cell technologies. Biotechnology Advances 31: 1776–1785.

Weiss IM, Lüke F, Eichner N, Guth C and Clausen‐Schaumann H (2013) On the function of chitin synthase extracellular domains in biomineralization. Journal of Structural Biology 183: 216–225.

Wu Y, Adam R, Williams SA and Bianco AE (1996) Chitinase genes expressed in infective larvae of the filarial nematodes, Acanthocheilonema viteae and Onchocerca volvulus. Molecular and Biochemical Parasitology 75: 207–219.

Yi H, Wu LQ, Bentley WE et al. (2005) Biofabrication with chitosan. Biomacromolecules 6: 2882–2884.

Yilmaz E (2004) Chitosan: a versatile biomaterial. Advances in Experimental Medicine and Biology 553: 59–68.

Zhang J, Xia W, Liu P et al. (2010) Chitosan modification and pharmaceutical/biomedical applications. Marine Drugs 8: 1962–1987.

Zhang Y, Foster JM, Nelson LS, Ma D and Carlow CK (2005) The chitin synthase genes chs‐1 and chs‐2 are essential for C. elegans development and responsibly for chitin deposition in the eggshell and pharynx, respectively. Developmental Biology 15: 330–339.

Zhao Y, Park RD and Muzzarelli RA (2010) Chitin deacetylases: properties and applications. Marine Drugs 8: 24–46.

Further Reading

Aam BB, Heggset EB, Norberg AL et al. (2010) Production of chito‐oligosaccharides and their potential applications in medicine. Marine Drugs 8: 1452–1557.

Bartnicki‐Garcia S (2006) Chitosomes: past, present and future. FEMS Yeast Research 6: 957–965.

Dahiya N, Tewari R and Hoondal GS (2006) Biotechnological aspects of chitinolytic enzymes: a review. Applied Microbiology and Biotechnology 71: 773–782.

Ghatak AS, Koch M, Guth C and Weiss IM (2013) Peptide induced crystallization of calcium carbonate on wrinkle patterned substrate: implications for chitin formation in mollusk. International Journal of Molecular Science 14: 11842–11860.

Hegedus D, Erlandson M, Gillot C and Toprak V (2009) New inshights into perithrophic matrix synthesis, architecture and function. Annual Review of Entomology 54: 285–302.

Jayakumar R, New N, Tokura S and Tamura H (2007) Sulfated chitin and chitosan as novel biomaterials. International Journal of Biological Macromolecules 40: 175–181.

Je JY and Kim SK (2012) Chitosan as potential marine nutraceutical. Advances in Food and Nutrition Research 65: 121–135.

Kaur S and Dhillon GS (2014) The versatile biopolymer chitosan: potential sources, evaluation of extraction methods and applications. Critical Reviews in Microbiology 40: 155–175.

Muzzarelli RA (2010) Chitins and chitosans as immunoadjuvants and non‐allergic drug carriers. Marine Drugs 8: 292–312.

Venkatesan J and Kim SK (2010) Chitosan composites for bone tissue engineering, an overview. Marine Drugs 8: 2252–2266.

Contact Editor close
Submit a note to the editor about this article by filling in the form below.

* Required Field

How to Cite close
Martínez, José P, Falomir, María Pilar, and Gozalbo, Daniel(Aug 2014) Chitin: A Structural Biopolysaccharide with Multiple Applications. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1002/9780470015902.a0000694.pub3]