Chitin

Chitin (C8H13O5N)n (/ˈkaɪtɪn/ KY-tin), a long-chain polymer of N-acetylglucosamine, is a derivative of glucose. It is a primary component of cell walls in fungi, the exoskeletons of arthropods, such as crustaceans and insects, the radulae of molluscs, cephalopod beaks, and the scales of fish and lissamphibians.[1] The structure of chitin is comparable to another polysaccharide—cellulose, forming crystalline nanofibrils or whiskers. In terms of function, it may be compared to the protein keratin. Chitin has proved useful for several medicinal, industrial and biotechnological purposes.

Not to be confused with chiton, chitlin, or keratin.

Structure of the chitin molecule, showing two of the N-acetylglucosamine units that repeat to form long chains in β-(1→4)-linkage.
Haworth projection of the chitin molecule.
A close-up of the wing of a leafhopper; the wing is composed of chitin.

Etymology

The English word "chitin" comes from the French word chitine, which was derived in 1821 from the Greek word χιτών (chiton), meaning covering.[2]

A similar word, "chiton", refers to a marine animal with a protective shell.

Chemistry, physical properties and biological function
Chemical configurations of the different monosaccharides (glucose and N-acetylglucosamine) and polysaccharides (chitin and cellulose) presented in Haworth projection

The structure of chitin was determined by Albert Hofmann in 1929.[3]

Chitin is a modified polysaccharide that contains nitrogen; it is synthesized from units of N-acetyl-D-glucosamine (to be precise, 2-(acetylamino)-2-deoxy-D-glucose). These units form covalent β-(1→4)-linkages (like the linkages between glucose units forming cellulose). Therefore, chitin may be described as cellulose with one hydroxyl group on each monomer replaced with an acetyl amine group. This allows for increased hydrogen bonding between adjacent polymers, giving the chitin-polymer matrix increased strength.

A cicada emerges from its chitinous larval exoskeleton.

In its pure, unmodified form, chitin is translucent, pliable, resilient, and quite tough. In most arthropods, however, it is often modified, occurring largely as a component of composite materials, such as in sclerotin, a tanned proteinaceous matrix, which forms much of the exoskeleton of insects. Combined with calcium carbonate, as in the shells of crustaceans and molluscs, chitin produces a much stronger composite. This composite material is much harder and stiffer than pure chitin, and is tougher and less brittle than pure calcium carbonate.[4] Another difference between pure and composite forms can be seen by comparing the flexible body wall of a caterpillar (mainly chitin) to the stiff, light elytron of a beetle (containing a large proportion of sclerotin).[5]

In butterfly wing scales, chitin is organized into stacks of gyroids constructed of chitin photonic crystals that produce various iridescent colors serving phenotypic signaling and communication for mating and foraging.[6] The elaborate chitin gyroid construction in butterfly wings creates a model of optical devices having potential for innovations in biomimicry.[6] Scarab beetles in the genus Cyphochilus also utilize chitin to form extremely thin scales (five to fifteen micrometres thick) that diffusely reflect white light. These scales are networks of randomly ordered filaments of chitin with diameters on the scale of hundreds of nanometres, which serve to scatter light. The multiple scattering of light is thought to play a role in the unusual whiteness of the scales.[7][8] In addition, some social wasps, such as Protopolybia chartergoides, orally secrete material containing predominantly chitin to reinforce the outer nest envelopes, composed of paper.[9]

Chitosan is produced commercially by deacetylation of chitin; chitosan is soluble in water, while chitin is not.[10]

Nanofibrils have been made using chitin and chitosan.[11]

Health effects

Chitin-producing organisms like protozoa, fungi, arthropods, and nematodes are often pathogens in other species.[12]

Humans and other mammals

Humans and other mammals have chitinase and chitinase-like proteins that can degrade chitin; they also possess several immune receptors that can recognize chitin and its degradation products in a pathogen-associated molecular pattern, initiating an immune response.[12]

Chitin is sensed mostly in the lungs or gastrointestinal tract where it can activate the innate immune system through eosinophils or macrophages, as well as an adaptive immune response through T helper cells.[12] Keratinocytes in skin can also react to chitin or chitin fragments.[12] According to in vitro studies, chitin is sensed by receptors, such as FIBCD1, KLRB1, REG3G, Toll-like receptor 2, CLEC7A, and mannose receptors.[12][13]

The immune response can sometimes clear the chitin and its associated organism, but sometimes the immune response is pathological and becomes an allergy;[14] allergy to house dust mites is thought to be driven by a response to chitin.[13]

Plants

Plants also have receptors that can cause a response to chitin, namely chitin elicitor receptor kinase 1 and chitin elicitor-binding protein.[12] The first chitin receptor was cloned in 2006.[15] When the receptors are activated by chitin, genes related to plant defense are expressed, and jasmonate hormones are activated, which in turn activate systematic defenses.[16] Commensal fungi have ways to interact with the host immune response that as of 2016 were not well understood.[15]

Some pathogens produce chitin-binding proteins that mask the chitin they shed from these receptors.[16][17] Zymoseptoria tritici is an example of a fungal pathogen that has such blocking proteins; it is a major pest in wheat crops.[18]

Fossil record

Chitin was probably present in the exoskeletons of Cambrian arthropods such as trilobites. The oldest preserved chitin dates to the Oligocene, about 25 million years ago, consisting of a scorpion encased in amber.[19]

Uses

Agriculture

Chitin is a good inducer of plant defense mechanisms for controlling diseases.[20] It has potential for use as a soil fertilizer or conditioner to improve fertility and plant resilience that may enhance crop yields.[21][22]

Industrial

Chitin is used in industry in many processes. Examples of the potential uses of chemically modified chitin in food processing include the formation of edible films and as an additive to thicken and stabilize foods and food emulsions.[23][24] Processes to size and strengthen paper employ chitin and chitosan.[25][26]

Research

How chitin interacts with the immune system of plants and animals has been an active area of research, including the identity of key receptors with which chitin interacts, whether the size of chitin particles is relevant to the kind of immune response triggered, and mechanisms by which immune systems respond.[14][18] Chitin and chitosan have been explored as a vaccine adjuvant due to its ability to stimulate an immune response.[12]

Chitin and chitosan are under development as scaffolds in studies of how tissue grows and how wounds heal, and in efforts to invent better bandages, surgical thread, and materials for allotransplantation.[10][27] Sutures made of chitin have been explored for many years, but as of 2015, none were on the market; their lack of elasticity and problems making thread have prevented commercial development.[28]

In 2014, a method for using chitosan as a reproducible form of biodegradable plastic was introduced.[29] Chitin nanofibers are extracted from crustacean waste and mushrooms for possible development of products in tissue engineering, medicine, and industry.[30]

See also
  • Biopesticide
  • Chitobiose
  • Lorica
  • Sporopollenin
  • Tectin

References
  1. Tang, WJ; Fernandez, JG; Sohn, JJ; Amemiya, CT (2015). "Chitin is endogenously produced in vertebrates". Curr Biol. 25 (7): 897–900. doi:10.1016/j.cub.2015.01.058. PMC 4382437. PMID 25772447.
  2. Auguste Odier (presented: 1821 ; published: 1823) "Mémoire sur la composition chimique des parties cornées des insectes" (Memoir on the chemical composition of the horny parts of insects), Mémoires de la Société d'Histoire Naturelle de Paris, 1 : 29-42. From page 35: "… la Chitine (c'est ainsi que je nomme cette substance de chiton, χιτον, enveloppe) …" (… chitine (it is thus that I name this substance from chiton, χιτον, covering) …)
  3. Hofmann hydrolyzed chitin using a crude preparation of the enzyme chitinase, which he obtained from the snail Helix pomatia. See:
    • A. Hofmann (1929) "Über den enzymatischen Abbau des Chitins und Chitosans" (On the enzymatic degradation of chitin and chitosan), Ph.D. thesis, University of Zurich (Zurich, Switzerland).
    • P. Karrer and A. Hofmann (1929) "Polysaccharide XXXIX. Über den enzymatischen Abbau von Chitin and Chitosan I," Helvetica Chimica Acta, 12 (1) : 616-637.
    • Nathaniel S. Finney and Jay S. Siegel (2008) "In Memorian: Albert Hofmann (1906-2008)," Chimia, 62 (5) : 444-447 ; see page 444. Available on-line at: University of Zurich
  4. Campbell, N. A. (1996) Biology (4th edition) Benjamin Cummings, New Work. p.69 ISBN 0-8053-1957-3
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