Hemicellulose

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A hemicellulose (also known as polyose) is one of a number of heteropolymers (matrix polysaccharides), such as arabinoxylans, present along with cellulose in almost all terrestrial plant cell walls. [1] Cellulose is crystalline, strong, and resistant to hydrolysis. Hemicelluloses are branched, shorter in length than cellulose, and also show a propensity to crystallize. [2] They can be hydrolyzed by dilute acid or base as well as a myriad of hemicellulase enzymes.

Contents

Most common molecular motif of hemicellulose Hemicellulose.png
Most common molecular motif of hemicellulose

Composition

Diverse kinds of hemicelluloses are known. Important examples include xylan, glucuronoxylan, arabinoxylan, glucomannan, and xyloglucan.

Hemicelluloses are polysaccharides often associated with cellulose, but with distinct compositions and structures. Whereas cellulose is derived exclusively from glucose, hemicelluloses are composed of diverse sugars, and can include the five-carbon sugars xylose and arabinose, the six-carbon sugars glucose, mannose and galactose, and the six-carbon deoxy sugar rhamnose. Hemicelluloses contain most of the D-pentose sugars, and occasionally small amounts of L-sugars as well. Xylose is in most cases the sugar monomer present in the largest amount, although in softwoods mannose can be the most abundant sugar. Not only regular sugars can be found in hemicellulose, but also their acidified forms, for instance glucuronic acid and galacturonic acid can be present. [3] [4]

Structural comparison to cellulose

Unlike cellulose, hemicelluloses consist of shorter chains – 500–3,000 sugar units. In contrast, each polymer of cellulose comprises 7,000–15,000 glucose molecules. [5] In addition, hemicelluloses may be branched polymers, while cellulose is unbranched. Hemicelluloses are embedded in the cell walls of plants, sometimes in chains that form a 'ground' – they bind with pectin to cellulose to form a network of cross-linked fibres.[ citation needed ]

Section of a cell wall; hemicellulose in green Plant cell wall diagram-en.svg
Section of a cell wall; hemicellulose in green

Based on the structural difference, like backbone linkages and side groups, as well as other factors, like abundance and distributions in plants, hemicelluloses can be categorized into four groups as following: [4] 1) xylans, 2) mannans; 3) mixed linkage β-glucans; 4) xyloglucans.

Xylans

Xylans usually consist of a backbone of β-(1→4)-linked xylose residues and can be further divided into homoxylans and heteroxylans. Homoxylans have a backbone of D-xylopyranose residues linked by β(1→4) glycosidic linkages. Homoxylans mainly have structural functions. Heteroxylans such as glucuronoxylans, glucuronoarabinoxylans, and complex heteroxylans, have a backbone of D-xylopyranose and short carbohydrate branches. For example, glucuronoxylan has a substitution with α-(1→2)-linked glucuronosyl and 4-O-methyl glucuronosyl residues. Arabinoxylans and glucuronoarabinoxylans contain arabinose residues attached to the backbone [6]

Xylan in hardwood Xylan hardwood.svg
Xylan in hardwood

Mannans

The mannan-type hemicellulose can be classified into two types based on their main chain difference, galactomannans and glucomannans. Galactomannans have only β-(1→4) linked D-mannopyranose residues in linear chains. Glucomannans consist of both β-(1→4) linked D-mannopyranose and β-(1→4) linked D-glucopyranose residues in the main chains. As for the side chains, D-galactopyranose residues tend to be 6-linked to both types as the single side chains with various amount. [1]

Mixed linkage β-glucans

The conformation of the mixed linkage glucan chains usually contains blocks of β-(1→4) D-Glucopyranose separated by single β-(1→3) D-Glucopyranose. The population of β-(1→4) and β-(1→3) are about 70% and 30%. These glucans primarily consist of cellotriosyl (C18H32O16) and cellotraosyl (C24H42O21)segments in random order. There are some study show the molar ratio of cellotriosyl/cellotraosyl for oat (2.1-2.4), barley (2.8-3.3), and wheat (4.2-4.5). [1] [5]

Beta-D-glucopyranose with carbon positions. Beta-D-glucopyranose-2D-skeletal.svg
Beta-D-glucopyranose with carbon positions.

Xyloglucans

Xyloglucans have a backbone similar to cellulose with α-D-xylopyranose residues at position 6. To better describe different side chains, a single letter code notation is used for each side chain type. G -- unbranched Glc residue; X -- α-d-Xyl-(1→6)-Glc. L -- β-Gal , S -- α-l-Araf, F-- α-l-Fuc. These are the most common side chains. [5]

The two most common types of xyloglucans in plant cell walls are identified as XXXG and XXGG. [1]

Biosynthesis

Hemicelluloses are synthesised from sugar nucleotides in the cell's Golgi apparatus. [8] Two models explain their synthesis: 1) a '2 component model' where modification occurs at two transmembrane proteins, and 2) a '1 component model' where modification occurs only at one transmembrane protein. After synthesis, hemicelluloses are transported to the plasma membrane via Golgi vesicles.

Each kind of hemicellulose is biosynthesized by specialized enzymes. [8] [9]

Mannan chain backbones are synthesized by cellulose synthase-like protein family A (CSLA) and possibly enzymes in cellulose synthase-like protein family D (CSLD). [8] [9] Mannan synthase, a particular enzyme in CSLA, is responsible for the addition of mannose units to the backbone. [8] [9] The galactose side-chains of some mannans are added by galactomannan galactosyltransferase. [8] [9] Acetylation of mannans is mediated by a mannan O-acetyltransferase, however, this enzyme has not been definitively identified. [9]

Xyloglucan backbone synthesis is mediated by cellulose synthase-like protein family C (CSLC), particularly glucan synthase, which adds glucose units to the chain. [8] [9] Backbone synthesis of xyloglucan is also mediated in some way by xylosyltransferase, but this mechanism is separate to its transferase function and remains unclear. [9] Xylosyltransferase in its transferase function is, however, utilized for the addition of xylose to the side-chain. [8] [9] Other enzymes utilized for side-chain synthesis of xyloglucan include galactosyltransferase (which is responsible for the addition of [galactose and of which two different forms are utilized), fucosyltransferase (which is responsible for the addition of fucose), and acetyltransferase (which is responsible for acetylation). [8] [9]

Xylan backbone synthesis, unlike that of the other hemicelluloses, is not mediated by any cellulose synthase-like proteins. [9] Instead, xylan synthase is responsible for backbone synthesis, facilitating the addition of xylose. [9] Several genes for xylan synthases have been identified. [9] Several other enzymes are utilized for the addition and modification of the side-chain units of xylan, including glucuronosyltransferase (which adds [glucuronic acid units), xylosyltransferase (which adds additional xylose units), arabinosyltransferase (which adds arabinose), methyltransferase (responsible for methylation), and acetyltransferase] (responsible for acetylation). [9] Given that mixed-linkage glucan is a non-branched homopolymer of glucose, there is no side-chain synthesis, only the addition of glucose to the backbone in two linkages, β1-3 and β1-4. [9] Backbone synthesis is mediated by enzymes in cellulose synthase-like protein families F and H (CSLF and CSLH), specifically glucan synthase. [8] [9] Several forms of glucan synthase from CSLF and CSLH have been identified. [8] [9] All of them are responsible for addition of glucose to the backbone and all are capable of producing both β1-3 and β1-4 linkages, however, it is unknown how much each specific enzyme contributes to the distribution of β1-3 and β1-4 linkages. [8] [9]

Applications

In the sulfite pulp process the hemicellulose is largely hydrolysed by the acid pulping liquor ending up in the brown liquor where the fermentable hexose sugars (around 2%) can be used for producing ethanol. This process was primarily applied to calcium sulfite brown liquors. [10]

Arabinogalactans can be used as emulsifiers, stabilizers and binders according to the Federal Food, Drug and Cosmetic Act. Arabinogalactans can also be used as bonding agent in sweeteners. [11]

The films based on xylan show low oxygen permeability and thus are of potential interest as packaging for oxygen-sensitive products. [12]

A Petri dish with bacterial colonies on an agar-based growth medium Agar plate with colonies.jpg
A Petri dish with bacterial colonies on an agar-based growth medium

Agar is used in making jellies and puddings. It is also growth medium with other nutrients for microorganisms. [13]

Curdlan can be used in fat replacement to produce diet food while having a taste and a mouth feel of real fat containing products. [13]

b-glucans have an important role in food supplement while b-glucans are also promising in health-related issues, especially in immune reactions and the treatment of cancer. [14]

Xanthan, with other polysaccharides can form gels that have high solution viscosity which can be used in the oil industry to thicken drilling mud. In the food industry, xanthan is used in products such as dressings and sauces. [15]

Alginate is an important role in the development of antimicrobial textiles due to its characteristics of environmental friendliness, and high industrialization level as a sustainable biopolymer. [16]

Natural functions

Hemicellulose contribution to structural support within plant cells Hemicellulose acting in the plant cell wall.jpg
Hemicellulose contribution to structural support within plant cells

As a polysaccharide compound in plant cell walls similar to cellulose, hemicellulose helps cellulose in the strengthening of plant cell walls. [6] Hemicellulose interacts with the cellulose by providing cross-linking of cellulose microfibrils: hemicellulose will search for voids in the cell wall during its formation and provide support around cellulose fibrils in order to equip the cell wall with the maximum possible strength it can provide. [6] Hemicellulose dominates the middle lamella of the plant cell, unlike cellulose which is primarily found in the secondary layers. This allows for hemicellulose to provide middle-ground support for the cellulose on the outer layers of the plant cell. In few cell walls, hemicellulose will also interact with lignin to provide structural tissue support of more vascular plants. [3] [17]

Extraction

There are many ways to obtain hemicellulose; all of these rely on extraction methods through hardwood or softwood trees milled into smaller samples. In hardwoods the main hemicellulose extract is glucuronoxlyan (acetylated xylans), while galactoglucomannan is found in softwoods. [18] [19] Prior to extraction the wood typically must be milled into wood chips of various sizes depending on the reactor used. Following this, a hot water extraction process, also known as autohydrolysis or hydrothermal treatment, is utilized with the addition of acids and bases to change the yield size and properties. [18] [19] The main advantage to hot water extraction is that it offers a method where the only chemical that is needed is water, making this environmentally friendly and cheap. [20]

The goal of hot water treatment is to remove as much hemicellulose from the wood as possible. This is done through the hydrolysis of the hemicellulose to achieve smaller oligomers and xylose. Xylose when dehydrated becomes furfural. [21] When xylose and furfural[ check spelling ] are the goal, acid catalysts, such as formic acid, are added to increase the transition of polysaccharide to monosaccharides. This catalyst also has been shown to also utilize a solvent effect to be aid the reaction. [21]

One method of pretreatment is to soak the wood with diluted acids (with concentrations around 4%). This converts the hemicellulose into monosaccharides. When pretreatment is done with bases (for instance sodium or potassium hydroxide) this destroys the structure of the lignin. [19] This changes the structure from crystalline to amorphous. Hydrothermal pretreatment is another method.[ further explanation needed ] This offers advantages such as no toxic or corrosive solvents are needed, nor are special reactors, and no extra costs to dispose of hazardous chemicals. [18]

The hot water extraction process is done in batch reactors, semi-continuous reactors, or slurry continuous reactors. For batch and semi-continuous reactors wood samples can be used in conditions such as chips or pellets while a slurry reactor must have particles as small as 200 to 300 micrometers. [19] While the particle size decreases the yield production decreases as well. [22] This is due to the increase of cellulose.[ citation needed ]

The hot water process is operated at a temperature range of 160 to 240 degrees Celsius in order to maintain the liquid phase. This is done above the normal boiling point of water to increase the solubilization of the hemicellulose and the depolymerization of polysaccharides. [21] This process can take several minutes to several hours depending on the temperature and pH of the system. [19] Higher temperatures paired with higher extraction times lead to higher yields. A maximum yield is obtained at a pH of 3.5. [18] If below, the extraction yield exponentially decreases. In order to control pH, sodium bicarbonate is generally added. [18] The sodium bicarbonate inhibits the autolysis of acetyl groups as well as inhibiting glycosyl bonds. Depending on the temperature and time the hemicellulose can be further converted into oligomers, monomers and lignin. [18]

See also

Related Research Articles

<span class="mw-page-title-main">Cell wall</span> Outermost layer of some cells

A cell wall is a structural layer that surrounds some cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, and functions as a selective barrier. Another vital role of the cell wall is to help the cell withstand osmotic pressure and mechanical stress. While absent in many eukaryotes, including animals, cell walls are prevalent in other organisms such as fungi, algae and plants, and are commonly found in most prokaryotes, with the exception of mollicute bacteria.

<span class="mw-page-title-main">Cellulose</span> Polymer of glucose and structural component of cell wall of plants and green algae

Cellulose is an organic compound with the formula (C
6H
10O
5)
n, a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. Some species of bacteria secrete it to form biofilms. Cellulose is the most abundant organic polymer on Earth. The cellulose content of cotton fibre is 90%, that of wood is 40–50%, and that of dried hemp is approximately 57%.

<span class="mw-page-title-main">Polysaccharide</span> Long carbohydrate polymers such as starch, glycogen, cellulose, and chitin

Polysaccharides, or polycarbohydrates, are the most abundant carbohydrates found in food. They are long-chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with water (hydrolysis) using amylase enzymes as catalyst, which produces constituent sugars. They range in structure from linear to highly branched. Examples include storage polysaccharides such as starch, glycogen and galactogen and structural polysaccharides such as hemicellulose and chitin.

<span class="mw-page-title-main">Mannans</span> Polysaccharides formed from mannose

Mannans are polymers containing the sugar mannose as a principal component. They are a type of polysaccharide found in hemicellulose, a major source of biomass found in higher plants such as softwoods. These polymers also typically contain two other sugars, galactose and glucose. They are often branched.

In polymer science, the polymer chain or simply backbone of a polymer is the main chain of a polymer. Polymers are often classified according to the elements in the main chains. The character of the backbone, i.e. its flexibility, determines the properties of the polymer. For example, in polysiloxanes (silicone), the backbone chain is very flexible, which results in a very low glass transition temperature of −123 °C. The polymers with rigid backbones are prone to crystallization in thin films and in solution. Crystallization in its turn affects the optical properties of the polymers, its optical band gap and electronic levels.

<span class="mw-page-title-main">Cellulase</span> Enzymes that catalyze cellulolysis

Cellulase is any of several enzymes produced chiefly by fungi, bacteria, and protozoans that catalyze cellulolysis, the decomposition of cellulose and of some related polysaccharides:

<span class="mw-page-title-main">Glycogen branching enzyme</span> Mammalian protein involved in glycogen production

1,4-alpha-glucan-branching enzyme, also known as brancher enzyme or glycogen-branching enzyme is an enzyme that in humans is encoded by the GBE1 gene.

A glucan is a polysaccharide derived from D-glucose, linked by glycosidic bonds. Glucans are noted in two forms: alpha glucans and beta glucans. Many beta-glucans are medically important. They represent a drug target for antifungal medications of the echinocandin class.

<span class="mw-page-title-main">Xylan</span> A plant cell wall polysaccharide

Xylan is a type of hemicellulose, a polysaccharide consisting mainly of xylose residues. It is found in plants, in the secondary cell walls of dicots and all cell walls of grasses. Xylan is the third most abundant polysaccharide on Earth, after cellulose and chitin.

β-Glucosidase Class of enzymes

β-Glucosidase is an enzyme that catalyses the following reaction:

<span class="mw-page-title-main">Lignocellulosic biomass</span> Plant dry matter

Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Any biomass rich in cellulose, hemicelluloses, and lignin are commonly referred to as lignocellulosic biomass. Each component has a distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers and they are covalently bound to lignin.

Xyloglucan is a hemicellulose that occurs in the primary cell wall of all vascular plants; however, all enzymes responsible for xyloglucan metabolism are found in Charophyceae algae. In many dicotyledonous plants, it is the most abundant hemicellulose in the primary cell wall. Xyloglucan binds to the surface of cellulose microfibrils and may link them together. It is the substrate of xyloglucan endotransglycosylase, which cuts and ligates xyloglucans, as a means of integrating new xyloglucans into the cell wall. It is also thought to be the substrate of alpha-expansin, which promotes cell wall enlargement.

<span class="mw-page-title-main">Beta-glucan</span> Class of chemical compounds

Beta-glucans, β-glucans comprise a group of β-D-glucose polysaccharides (glucans) naturally occurring in the cell walls of cereals, bacteria, and fungi, with significantly differing physicochemical properties dependent on source. Typically, β-glucans form a linear backbone with 1–3 β-glycosidic bonds but vary with respect to molecular mass, solubility, viscosity, branching structure, and gelation properties, causing diverse physiological effects in animals.

<span class="mw-page-title-main">Cellulose synthase (UDP-forming)</span> Cellulose synthesizing enzyme in plants and bacteria

The UDP-forming form of cellulose synthase is the main enzyme that produces cellulose. Systematically, it is known as UDP-glucose:(1→4)-β-D-glucan 4-β-D-glucosyltransferase in enzymology. It catalyzes the chemical reaction:

Homopolysaccharides are polysaccharides composed of a single type of sugar monomer. For example, cellulose is an unbranched homopolysaccharide made up of glucose monomers connected via beta-glycosidic linkages; glycogen is a branched form, where the glucose monomers are joined by alpha-glycosidic linkages. Depending upon the molecules attached that are of the following types:

  1. Glucan - A polysaccharide of glucose
  2. Fructan - A polysaccharide of fructose
  3. Galactan - A polysaccharide of galactose
  4. Araban - A polysaccharide of arabinose
  5. Xylan - A polysaccharide of xylose

Oligosaccharides and polysaccharides are an important class of polymeric carbohydrates found in virtually all living entities. Their structural features make their nomenclature challenging and their roles in living systems make their nomenclature important.

Mixed-linkage glucan : xyloglucan endotransglucosylase (MXE) is a plant cell wall-modifying enzyme found in plants of the genus Equisetum. The enzyme is proposed, in vivo, to catalyse the endotransglucosylation of two different hemicellulose polysaccharides, mixed-linkage glucan and xyloglucan, by effectively 'stitching' them together. However only the 'stitching' of a mixed-linkage glucan polysaccharide to a xyloglucan oligosaccharide has actually been witnessed to date.

Mixed-linkage glucan (MLG), sometimes incorrectly referred to as beta-glucan, is a hemicellulosic polysaccharide consisting of β-D(1-3) and β-D(1-4) linked glucosyl residues. MLG is highly prevalent within the Poales, where it has important properties in the diet. In addition, although thought to be confined to the Poales, MLG has been found to be highly prevalent in plants of the distantly related genus Equisetum.

Arabinoxylan is a form of the hemicellulose xylan found in both the primary and secondary cell walls of plants which in addition to xylose contains substantial amounts of another pentose sugar, arabinose. The term arabinoxylan usually refers to feruloyl-arabinoxylan from grasses and other commelinids containing moieties of the phenolic ferulic acid that can undergo oxidative coupling forming crosslinks between arabinoxylan chains and with lignin. Whilst arabinose has been found linked to xylan in non-commelinid plants, ferulic acid has not been reported on these and unlike feruloyl-arabinoxylan these arabinoxylans are not monophyletic. The remainder of this article refers to feruloyl-arabinoxylan from cell walls of grasses and other commelinid species.

<span class="mw-page-title-main">Glucanase</span>

Glucanases are enzymes that break down large polysaccharides via hydrolysis. The product of the hydrolysis reaction is called a glucan, a linear polysaccharide made of up to 1200 glucose monomers, held together with glycosidic bonds. Glucans are abundant in the endosperm cell walls of cereals such as barley, rye, sorghum, rice, and wheat. Glucanases are also referred to as lichenases, hydrolases, glycosidases, glycosyl hydrolases, and/or laminarinases. Many types of glucanases share similar amino acid sequences but vastly different substrates. Of the known endo-glucanases, 1,3-1,4-β-glucanase is considered the most active.

References

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  2. ↑ Smith, Peter J.; Curry, Thomas M.; Yang, Jeong-Yeh; Barnes, William J.; Ziegler, Samantha J.; Mittal, Ashutosh; Moremen, Kelley W.; York, William S.; Bomble, Yannick J.; Peña, Maria J.; Urbanowicz, Breeanna R. (2022-07-13). "Enzymatic Synthesis of Xylan Microparticles with Tunable Morphologies". ACS Materials Au. 2 (4): 440–452. doi:10.1021/acsmaterialsau.2c00006. ISSN   2694-2461. PMC   9284610 . PMID   35856073.
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  14. ↑ Vetvicka, V., Vannucci, L., Sima, P., & Richter, J. (2019). Beta Glucan: Supplement or Drug? From Laboratory to Clinical Trials. Molecules, 24(7), 1251. https://doi.org/10.3390/molecules24071251
  15. ↑ Navarrete, R. C., Himes, R. E., & Seheult, J. M. (2000). Applications of Xanthan Gum in Fluid-Loss Control and Related Formation Damage. SPE Permian Basin Oil and Gas Recovery Conference. SPE Permian Basin Oil and Gas Recovery Conference. https://doi.org/10.2118/59535-ms
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  17. ↑ Plaza, Merichel; Turner, Charlotta (2015). "Pressurized hot water extraction of bioactives". Trends in Analytical Chemistry. 71: 39–54. doi: 10.1016/j.trac.2015.02.022 .
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  20. ↑ Gianluca Gallinaa Álvaro Cabezaa Henrik Grénmanbc Pierdomenico Biasibd Juan García-Sernaa Tapio Salmi (March 2018). "Hemicellulose extraction by hot pressurized water pretreatment at 160 °C for 10 different woods: Yield and molecular weight" (PDF). The Journal of Supercritical Fluids. 133 (Part 2): 716–725. doi:10.1016/j.supflu.2017.10.001 . Retrieved 7 October 2017.
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  22. ↑ Ayrilmis N, Kwon J, Han T (October 2017). "Effect of Wood Chip Size on Hemicellulose Extraction and Technological Properties of Flakeboard". Turkish Journal of Agriculture & Forestry. 41: 331–337. doi: 10.3906/tar-1704-63 .{{cite journal}}: CS1 maint: multiple names: authors list (link)
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