Levan polysaccharide
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Levan is a naturally occurring
fructan A fructan is a polymer of fructose molecules. Fructans with a short chain length are known as fructooligosaccharides. Fructans can be found in over 12% of the angiosperms including both monocots and dicots such as agave, artichokes, asparagus, l ...
present in many plants and microorganisms. This polymer is made up of
fructose Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorb ...
, a monosaccharide sugar, connected by 2,6 beta glycosidic linkages. Levan can have both branched and linear structures of relatively low molecular weight. Branched levan forms a very small, sphere-like structure with basal chains 9 units long. The 2,1 branching allows methyl ethers to form and create a spherical shape. The ends of levan also tend to contain a glucosyl residue. Branched levan tends to be more stable than the linear structure. However, the amount of branching and length of polymerization tends to vary among different species. The shortest levan is 6-
kestose Kestose is a class of sugars that belongs to a group of fructooligosaccharides. Chemical properties Kestoses are typical fructooligosaccharides, and in its structure, one fructose molecule is combined with sucrose to form a trisaccharide. In ...
, a chain of two fructose molecules and a terminal glucose molecule.


Discovery

Levan was first discovered through research on nattō, a traditional Japanese dish. Natto was known as a "
superfood Superfood is a marketing term for food claimed to confer health benefits resulting from an exceptional nutrient density. The term is not commonly used by experts, dietitians and nutrition scientists, most of whom dispute that particular foods ...
" which promoted health and longevity in Japan during the late 1800s. In 1881, Lippmann first discovered "lävulan" (levan) as the remaining gum from
molasses Molasses () is a viscous substance resulting from refining sugarcane or sugar beets into sugar. Molasses varies in the amount of sugar, method of extraction and age of the plant. Sugarcane molasses is primarily used to sweeten and flavour foods ...
in sugar beet production. Later in 1901, Greig-Smith coined the name “levan” based on the levorotatory properties of this substance in
polarized light Polarization ( also polarisation) is a property applying to transverse waves that specifies the geometrical orientation of the oscillations. In a transverse wave, the direction of the oscillation is perpendicular to the direction of motion of t ...
.


Production

Levan is synthesized in
archaea Archaea ( ; singular archaeon ) is a domain of single-celled organisms. These microorganisms lack cell nuclei and are therefore prokaryotes. Archaea were initially classified as bacteria, receiving the name archaebacteria (in the Archaeba ...
, fungi, bacteria, and a limited number of plant species. Fructans such as levan are synthesized from
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refine ...
, a
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...
containing glucose and fructose. In plants, the
vacuole A vacuole () is a membrane-bound organelle which is present in plant and fungal cells and some protist, animal, and bacterial cells. Vacuoles are essentially enclosed compartments which are filled with water containing inorganic and organic m ...
is where fructan production occurs. Sucrose:sucrose/fructan 6-fructosyltransferase is the fructosyltransferase in the vacuole which creates the beta 2,6 linkages to form the linear form of levan. Bacteria also use a fructosyltransferase known as levansucrase to form levan. These enzymes in bacteria form the 2,1 linkages in the linear basal chains of levan to allow for branching points to occur. Many bacteria produce levan in the cell exterior. This production can be sensitive to temperature, oxygen concentration, pH, and other factors. Levan production in bacteria is typically a sign of growth in population. There are also possible ways to produce by fracturing
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu ...
mucilage Mucilage is a thick, gluey substance produced by nearly all plants and some microorganisms. These microorganisms include protists which use it for their locomotion. The direction of their movement is always opposite to that of the secretion of m ...
. Levans are produced by microbes during colonization of a food substrate. ''
Erwinia amylovora Fire blight, also written fireblight, is a contagious disease affecting apples, pears, and some other members of the family Rosaceae. It is a serious concern to apple and pear producers. Under optimal conditions, it can destroy an entire orchard ...
'' exudes levan and amylovoran as part of its
biofilm A biofilm comprises any syntrophic consortium of microorganisms in which cells stick to each other and often also to a surface. These adherent cells become embedded within a slimy extracellular matrix that is composed of extracellular po ...
. Together they contribute to its pathogenicity. In 2016, Ua-Arak et al. developed a
sourdough Sourdough or sourdough bread is a bread made by the fermentation of dough using wild lactobacillaceae and yeast. Lactic acid from fermentation imparts a sour taste and improves keeping qualities. History In the ''Encyclopedia of Food Microbio ...
method with high levan output (among other exopolysaccharides).


Properties

The beta 2,6 linkages of levan allow for it to be soluble in both water and oil; however, the water temperature varies the degree of
solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...
. Levan also is insoluble in many organic solvents such as methanol, ethanol, and isopropanol. The branching of levan allows it to have a high tensile and cohesive strength, while the hydroxyl groups contribute to adhesion with other molecules. The intrinsic viscosity n, a measure of the substance effect on viscosity of a solution, tends to be very low for levan. This allows levan to be utilized in a pharmaceutical setting.


Real world implications

Many industries such as
food Food is any substance consumed by an organism for nutritional support. Food is usually of plant, animal, or fungal origin, and contains essential nutrients, such as carbohydrates, fats, proteins, vitamins, or minerals. The substance is in ...
, beverages, cosmetics, and even medicine utilize levan in their products. One of the reasons levan is able to be used in such a versatile way is that it fulfills all safety guidelines. Levan does not cause any form of skin or
eye irritation The human eye is a sensory organ, part of the sensory nervous system, that reacts to visible light and allows humans to use visual information for various purposes including seeing things, keeping balance, and maintaining circadian rhythm. T ...
, has not shown any allergenic effects, and poses no threat of
cytotoxicity Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa''). Cell physiology Treating c ...
.


Food

In the food industry, levan is incorporated due to its prebiotic effects,
cholesterol lowering Lipid-lowering agents, also sometimes referred to as hypolipidemic agents, cholesterol-lowering drugs, or antihyperlipidemic agents are a diverse group of pharmaceuticals that are used to lower the level of lipids and lipoproteins such as cholestero ...
ability, and adhesive properties. It also occurs naturally in low amounts in food for human consumption. Levan is also included in many dairy products as fiber or sweetener. Commercial, non-alcoholic beverages use levan as well in ultra-high-fructose-syrups. Interestingly, levan causes useful bacterial growth and proliferation which can be especially important in the gut because it causes a decrease in population of the pathogenic bacteria.


Cosmetics

Levan can be used for
hair care Hair care is an overall term for hygiene and cosmetology involving the hair which grows from the human scalp, and to a lesser extent facial, pubic and other body hair. Hair care routines differ according to an individual's culture and the p ...
and
skin whitening Skin whitening, also known as skin lightening and skin bleaching, is the practice of using chemical substances in an attempt to lighten the skin or provide an even skin color by reducing the melanin concentration in the skin. Several chemicals ha ...
. In hair care products, levan acts to form a film which creates a hair holding effect utilized in various gels and mousses. Levan is used as a skin whitener as well because it has been tested to show inhibition on melanin production by decreasing the activity of the enzyme
tyrosinase Tyrosinase is an oxidase that is the rate-limiting enzyme for controlling the production of melanin. The enzyme is mainly involved in two distinct reactions of melanin synthesis otherwise known as the Raper Mason pathway. Firstly, the hydroxy ...
which is responsible for
melanogenesis Melanocytes are melanin-producing neural crest-derived cells located in the bottom layer (the stratum basale) of the skin's epidermis, the middle layer of the eye (the uvea), the inner ear, vaginal epithelium, meninges, bones, and hear ...
.


Medicine

Levan has shown uses for burned tissue,
anti-inflammation Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as op ...
, and
aquaculture Aquaculture (less commonly spelled aquiculture), also known as aquafarming, is the controlled cultivation ("farming") of aquatic organisms such as fish, crustaceans, mollusks, algae and other organisms of value such as aquatic plants (e.g. lot ...
. By combining levan into a thin film, it is able to activate an enzyme known as metalloproteinase which increases the recovery and healing process. In the case of inflammation, levan interacts with the aggregating cells and affects their adhesion to the blood vessel causing reduced accumulation. In aquaculture, results have shown that levan incorporated diets could possibly cause an increase in aggregation of viruses allowing for easier
phagocytic Phagocytosis () is the process by which a cell uses its plasma membrane to engulf a large particle (≥ 0.5 μm), giving rise to an internal compartment called the phagosome. It is one type of endocytosis. A cell that performs phagocytosis is c ...
removal. Levan produced by ''Pantoea agglomerans'' ZMR7 was reported to decrease the viability of rhabdomyosarcoma (RD) and breast cancer (MDA) cells compared with untreated cancer cells. In addition, it has high antiparasitic activity against the promastigote of ''Leishmania tropica''


See also

* Food microbiology * Industrial microbiology


References

{{Carbohydrates Biochemistry Polysaccharides