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Chitosan

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File:Chitosan2.jpg
Chemical formula of chitosan

Chitosan (Template:PronEng) is a linear polysaccharide composed of randomly distributed β-(1-4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It has a number of commercial and possible biomedical uses.

Manufacture and properties

Commercial chitosan is derived from the shells of shrimp and other sea crustaceans, including Pandalus borealis, pictured here.[1]

Chitosan is produced commercially by deacetylation of chitin , which is the structural element in the exoskeleton of crustaceans (crabs, shrimp, etc.) and cell walls of fungi. The degree of deacetylation (%DA) can be determined by NMR spectroscopy, and the %DA in commercial chitosans is in the range 60-100 %.

The amino group in chitosan has a pKa value of ~6.5, thus, chitosan is positively charged and soluble in acidic to neutral solution with a charge density dependent on pH and the %DA-value. This makes chitosan a bioadhesive which readily binds to negatively charged surfaces such as mucosal membranes. Chitosan enhances the transport of polar drugs across epithelial surfaces, and is biocompatible and biodegradable. Purified qualities of chitosans are available for biomedical applications.

Chitosan and its derivatives such as trimethylchitosan (where the amino group has been trimethylated) have been used in non-viral gene delivery. Trimethylchitosan, or quaternised chitosan, has been shown to transfect breast cancer cells; with increased degree of trimethylation increasing the cytotoxicity and at approximately 50% trimethylation the derivative is the most efficient at gene delivery. Oligomeric derivatives (3-6 kDa) are relatively non-toxic and have good gene delivery properties.[2]

Usage

Agricultural & Horticultural use

Natural Biocontrol & Elicitor

In agriculture, chitosan is used primarily as a natural seed treatment and plant growth enhancer, and as a substance that boosts the ability of plants to defend against fungal infections.[3] The natural biocontrol active ingredient, chitin/chitosan, are found in the shells of crustaceans, such as lobsters, crabs, and shrimp, and many other organisms including insects and fungi. It is one of the most abundant bio-gradable materials in the world. Degraded molecules of chitin/chitosan exist in soil and water. Chitosan applications for plants and crops are regulated by the EPA and the USDA National Organic Program regulates its use on organic certified farms and crops.[4] It is approved for use outdoors and indoors on plants and crops grown commercially and by consumers. The natural biocontrol ability of chitosan should not be confused with the effects of fertilizers or pesticides upon plants or the environment. It represents a new tier of cost effective biological control of crops.[5]

File:YEA! treated broccoli.JPG
Day 30: non-treated broccoli vs. YEA!® (chitosan) treated broccoli (Research Trial by Colorado State University)

Its known benefits for agriculture and horticulture are extensive. The biocontrol mode of action of chitosan elicits natural defense responses within plant to resist against insects, pathogens, and soil borne diseases.[6] Chitosan increases photosynthesis, promotes and enhances plant growth, stimulates nutrient uptake, increases germination and sprouting, and boost plant vigor. When used as seed treatment or seed coating on cotton, corn, seed potatoes, soybean, sugar beet, tomato, wheat and many other seeds it elicits an innate immunity response in developing roots which destroy parasitic cyst nematodes without harming beneficial nematodes and organisms.[7][8] Agricultural applications of chitosan can reduce environmental stress due to drought and soil deficiencies, strengthen seed vitality, improve stand quality, increase yields, and reduce fruit decay of vegetables, fruits and citrus crops (see photo right).[9] Horticultural applications of chitosan increases blooms, extends the life of cut flowers and Christmas trees, as well eliciting pine tree resin flow to resist pine beetle infestation.[10]

NASA life support GAP technology with untreated beans (left tube) and ODC™ chitosan biocontrol treated beans (right tube) returned from the Mir space station aboard the space shuttle – September 1997 [11]

Chitosan has a rich history of being researched for applications in agriculture and horticulture dating back to the 1980s. By 1989 Bentech Labs patented chitosan salt solutions applied to crops for improved freeze protection or to crop seed for seed priming.[12] Shortly thereafter Bentech's chitosan salt received the first ever biopesticide label from the EPA. Numerous other chitosan patents for plants soon followed. Chitosan applications to protect plants have been used in space as well. NASA first flew a chitosan experiment to protect adzuki beans grown aboard the space shuttle and Mir space station in 1997 (see photo left).[13] NASA results revealed chitosan induces increased growth (biomass) and pathogen resistance due to elevated levels of beta 1-3 glucanase enzymes within plant cells. NASA confirmed chitosan elicits the same effect in plants on earth.[14] Over 20 years of R&D by DuPont/ConAgra Ventures (DCV) and AgriHouse Inc have gone into developing non-toxic low molecular weight chitosan polymer solutions safe enough for broad spectrum agricultural and horticultural use.[15][16] In 2008, AgriHouse Inc, Denver [Berthoud], Colorado, was granted EPA natural broad spectrum elicitor status for YEA!® Yield Enhancing Agent, a liquid solution containing an active ingredient of 0.25% chitosan. YEA!® is a next generation natural elicitor solution for agriculture and horticultural. A milliliter of YEA!® contains over 14.4 X 10¹³ bio-active low molecular weight chitosan molecules. YEA!® is 600 times more effective than common chitosan.[17] Given its low potential for toxicity and its abundance in the natural environment, chitosan does not harm people, pets, wildlife, or the environment when used according to label directions.[18] Agricultural chitosan facts are located on USDA and EPA web sites.[19][20]

Water Filtration

Chitosan can also be used in water processing engineering as a part of a filtration process. Chitosan causes the fine sediment particles to bind together and is subsequently removed with the sediment during sand filtration. Chitosan also removes phosphorus, heavy minerals, and oils from the water. Chitosan is an important additive in the filtration process. Sand filtration apparently can remove up to 50% of the turbidity alone while the chitosan with sand filtration removes up to 99% turbidity.[21] Chitosan has been used to precipitate caseins from bovine milk and cheese making[1][2]

Chitosan is also useful in other filtration situations, where one may need to remove suspended particles from a liquid. Chitosan, in combination with bentonite, gelatin, silica gel, isinglass, or other fining agents is used to clarify wine, mead, and beer. Added late in the brewing process, chitosan improves flocculation, and removes yeast cells, fruit particles, and other detritus that cause hazy wine. Chitosan combined with colloidal silica is becoming a popular fining agent for white wines, because chitosan does not require acidic tannins (found primarily in red wines) to flocculate with.[22]

Industrial use

Scientists have recently developed a polyurethane coating that heals its own scratches when exposed to sunlight, offering the promise of scratch-free cars and other products. The self-healing coating uses chitosan incorporated into traditional polymer materials, such as those used in coatings on cars to protect paint. When a scratch damages the chemical structure, the chitosan responds to ultraviolet light by forming chemical chains that begin bonding with other materials in the substance, eventually smoothing the scratch. The process can take less than an hour.[23]

Marek W. Urban, a scientist working on this project said that the polymer can only repair itself in the same spot once, and would not work after repeated scratches.[24]

Biomedical use

Chitosan's properties allow it to rapidly clot blood, and has recently gained approval in the USA for use in bandages and other hemostatic agents. Chitosan purified from shrimp shells is used in the range of hemostatic products sold under the Celox name. Celox is made by Medtrade Products Ltd of Crewe, England[25] and in the chitosan dressings made by HemCon Medical Technologies Inc. of Portland, OR, USA [26]. Celox has been shown in testing by the US Marines to quickly stop bleeding and result in 100% survival of otherwise lethal arterial wounds and to reduce blood loss[27]. The Celox and Hemcon products reduce blood loss in comparison to gauze dressings and increases patient survival[28]. Celox and Hemcon products have been sold to the United States Army, who have already used the bandages on the battlefields of Iraq [29]. Chitosan is hypoallergenic, and has natural anti-bacterial properties, further supporting its use in field bandages.[30]

Claimed health benefits

Chitosan is frequently sold in tablet form at health stores as a 'fat attractor': It is supposed to have the capability of attracting fat from the digestive system and expelling it from the body so that users can, it is claimed, lose weight without eating less. However, some scientific research suggests that these claims are likely without substance. The FDA has issued warning letters to several companies who make claims that are not supported by reliable scientific evidence to the benefits of chitosan as a fat blocker.[31] At best, unmodified chitosan would remove roughly 10 calories per day from a person's diet.[32] Modified chitosan is claimed to absorb anywhere up to three to six times its weight in fat and oils. Detractors claim[who?] that using chitosan may have the deleterious effect of rendering ineffective certain minerals found in foodstuffs and required by the body in order to remain healthy.

Discussion of medical research on chitosan

With the unavailability of specific research studies to support the claims made on chitosan as a revolutionary weight loss supplements, one must be careful on what is fact and what is speculation. The following are conclusions and specific discussion made from researchers, although take note that their specific studies were not given with precise accounts of their experimentation.

It is now generally accepted that soluble dietary fibers increase gastrointestinal lumen viscosity (Edwards, 1990) and delay gastric emptying (Chang, 1983)[citation needed]. Chitosans have specifically been shown to alter bile acid composition, increase neutral sterol excretion and reduce ileal fat digestibility (Fukada, 1991; Maezaki, 1993; Razdan & Pettersson, 1994)[citation needed]. The mechanisms by which chitosans achieve these effects are not fully established, although increased intestinal viscosity and increased bile acid-binding capacity are two proposals currently favored (Furda, 1990)[citation needed]. Since polyglucosamines are the second-most-ubiquitous dietary fiber after cellulose, it is reasonable to assume that much more research regarding the nutritional significance of these important dietary fibers is to be expected (Knorr, 1991)[citation needed]. Chitosan has such characteristics that are associated with a dietary fiber which are assumed to be related to the reductions in cholesterol as well as increases in the excretion of neutral steroids observed in animal experiments (Furda, 1990; Ikeda, 1993; Razdan & Pettersson, 1994)[citation needed]. Chitosan, which is largely deacetylated, contains cationic groups located on the polyglucosamine chain (Sugano, 1993)[citation needed]. Thus, chitosan may have a bile acid-binding capacity, causing entrapment or disintegration of mixed micelles in the duodenum and ileum (Furda, 1990)[citation needed]. This interruption in bile acid circulation would lead to reduced lipid absorption and increased sterol excretion. Chitosan is relatively insoluble in water but is soluble in dilute acids, giving rise to highly-viscous dietary fibers (Furda, 1990)[citation needed]. It has been suggested that viscous dietary fibers such as chitosan inhibit uptake of dietary lipids by increasing the thickness of the intestinal lumen boundary layer, a proposal again supported by numerous animal experiments (Sugano, 1993; Ikeda, 1993)[citation needed].

  • [3] Video of self-healing action
  • [4] Jamie Fritch's take on chitosan
  • The Chitosanase Web Page – dedicated to the enzymatic hydrolysis of chitosan.
  • ScienCentral News "But now, scientists have created a bandage that is actually able to clot a bullet wound in less than a minute. The bandages are laced with a mixture of ground shrimp shells and vinegar, a concoction that has been found to clot blood instantly. The key ingredient in the shrimp shells is called chitosan."
  • A Critical look on ChitosanA critical look on the claims how chitosan can be used for weight management
  • [5] Catalyst (an ABC-TV Program) looked at chitosan's potential as a surgical adhesive in theatre.

See also

Footnotes

  1. ^ Shahidi, F. and Synowiecki, J. (1991). "Isolation and characterization of nutrients and value-added products from snow crab (Chionoecetes opilio) and shrimp (Pandalus borealis) processing discards" (PDF). Journal of Agricultural and Food Chemistry. 39 (8). American Chemical Society: 1527–1532. doi:10.1021/jf00008a032.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Kean T, Roth S, Thanou M (2005). "Trimethylated chitosans as non-viral gene delivery vectors: cytotoxicity and transfection efficiency". J Control Release. 103 (3): 643–53. doi:10.1016/j.jconrel.2005.01.001. PMID 15820411. {{cite journal}}: |access-date= requires |url= (help)CS1 maint: multiple names: authors list (link)
  3. ^ "Linden, J., Stoner, R., Knutson, K. Gardner-Hughes, C. "Organic Disease Control Elicitors". Agro Food Industry Hi-Te (p12-15 Oct 2000)" (PDF). {{cite web}}: Cite has empty unknown parameter: |1= (help)
  4. ^ "USDA NOP and EPA Rule on Chitosan, Federal Register/Vol. 72, No. 236/Monday, December 10, 2007/Rules and Regulation". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  5. ^ "Goosen, M. F., 1996, Applications of Chitin and Chitosan, pp 132-139, CRC Press". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  6. ^ "Linden, J.C. and Stoner, R.J. 2005. Proprietary Elicitor Affects Seed Germination and Delays Fruit Senescence. Journal of Food, Agriculture & Environment (in press)" (PDF). {{cite web}}: Cite has empty unknown parameter: |1= (help).
  7. ^ "Smiley R., Cook R.J., Pauliz T., Seed Treatment for Sample Cereal Grains Oregon State University, 2002, EM 8797" (PDF). {{cite web}}: Cite has empty unknown parameter: |1= (help)
  8. ^ "Stoner R., Linden J., Micronutrient elicitor for treating nematodes in field crops, 2006, Patent Pending, Pub. no.: US 2008/0072494 A1". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  9. ^ "Linden, J.C. and Stoner, R.J. 2007. Pre-harvest application of proprietary elicitor delays fruit senescence. A. Ramina et al. (eds.). Advances in Plant Ethylene Research: Proceedings of the 7th International Symposium on the Plant Hormone Ethylene. pp 301-302. Springer: Dordrecht, The Netherlands". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  10. ^ "YouTube video / Chitosan Extends the Life of Plants and Trees". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  11. ^ "NASA aeroponic and biocontrols in space". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  12. ^ "Treatment of Plants with Chitosan Salts, 1989, Patent WO/1989/007395". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  13. ^ "Stoner, R., Progressive Plant Growing Has Business Blooming, Environmental and Agricultural Resources NASA Spinoff 2006, pp68-71". {{cite web}}: Cite has empty unknown parameter: |1= (help).
  14. ^ "Linden, J., Stoner, R., YEA!® Elicitor Response Comparison to Chitin / Chitosan in Mung Bean and Adzuki Bean Germination Experiments, 2008" (PDF). {{cite web}}: Cite has empty unknown parameter: |1= (help)
  15. ^ "BIOPOLYMERS Making Materials Nature's Way". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  16. ^ "SeedQuest Press Release: AgriHouse Acquires DCV Chitosan IP and Patents". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  17. ^ "Linden, J., Stoner, R., YEA!® Elicitor Response Comparison to Chitin / Chitosan in Mung Bean and Adzuki Bean Germination Experiments, 2008, page 2" (PDF). {{cite web}}: Cite has empty unknown parameter: |1= (help)
  18. ^ "Chitosan Exemption from the Requirement of a Tolerance". {{cite web}}: Cite has empty unknown parameter: |1= (help)
  19. ^ "Control Strategies to reduce postharvest decay of fresh fruits and vegetables".
  20. ^ "Chitosan; Poly-D-glucosamine (128930) Fact Sheet". US Environmental Protection Agency. 2006. Retrieved 2006-07-10. {{cite web}}: Unknown parameter |month= ignored (help)
  21. ^ Alan Woodmansey (Highway Engineer) (2002). "Chitosan Treatment of Sediment Laden Water - Washington State I-90 Issaquah Project". Federal Highway Administration. U.S. Department of Transportation. Retrieved 2006-07-10. {{cite web}}: Unknown parameter |month= ignored (help)
  22. ^ Rayner, Terry. "Fining and Clarifying Agents". Retrieved 2006-07-18.
  23. ^ Self-Repairing Oxetane-Substituted Chitosan Polyurethane Networks
  24. ^ Coating makes scratches on cars disappear
  25. ^ CELOX Emergency Hemostatic Agent Controls Serious Bleeding Fast
  26. ^ "HemCon Medical Technologies Inc". 2004.
  27. ^ Journal of Emergency Medicine: 74–81. 2008. {{cite journal}}: Missing or empty |title= (help); Unknown parameter |month= ignored (help)
  28. ^ Pusateri, A. E., S. J. McCarthy, K. W. Gregory, R. A. Harris, L. Cardenas, A. T. McManus & C. W. Goodwin Jr. (2003). "Effect of a chitosan-based hemostatic dressing on blood loss and survival in a model of severe venous hemorrhage and hepatic injury in swine". Journal of Trauma. 4 (1): 177–182. doi:10.1097/00005373-200301000-00023. {{cite journal}}: Unknown parameter |quotes= ignored (help)CS1 maint: multiple names: authors list (link)
  29. ^ Karen Lurie. "War Bandages".
  30. ^ Kevin McCue (2003). "New Bandage Uses Biopolymer" ([dead link] – Scholar search). Chemistry.org. American Chemical Society. Retrieved 2006-07-10. {{cite journal}}: External link in |format= (help); Unknown parameter |month= ignored (help)
  31. ^ "Warning Letter for Weight Loss Products". Retrieved 2006-07-10.
  32. ^ Matthew D. Gades and Judith S. Stern (2003). "Chitosan supplementation and fecal fat excretion in men". Obesityresearch.org. Obesity Research. Retrieved 2008-02-18.

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