ARABINOGALACTAN

Molecular Formula: C20H36O14
Molecular Weight: 500.5
CAS Number: 9036-66-2
EC Number: 232-910-0
MDL number: MFCD00062638

Arabinogalactan is a biopolymer consisting of arabinose and galactose monosaccharides. 
Two classes of arabinogalactans are found in nature: plant arabinogalactan and microbial arabinogalactan. 
In plants, it is a major component of many gums, including gum arabic and gum ghatti. 
Galactoarabinan is often found attached to proteins, and the resulting arabinogalactan protein (AGP) functions as both an intercellular signaling molecule and a glue to seal plant wounds.
The microbial arabinogalactan is a major structural component of the mycobacterial cell wall.
Both the arabinose and galactose exist solely in the furanose configuration. 
The galactan portion of microbial arabinogalactan is linear, consisting of approximately 30 units with alternating β-(1-5) and β-(1-6) glycosidic linkages. 
The arabinan chain, which consists of about 30 residues, is attached at three branch points within the galactan chain, believed to be at residues 8, 10 and 12.
The arabinan portion of the polymer is a complex branched structure, usually capped with mycolic acids; the arabinan glycosidic linkages are α-(1-3), α-(1-5), and β-(1-2).

The mycobacterial arabinogalactan is recognized by a putative immune lectin intelectin present in chordates.
Arabinogalactan is a polysaccharide extracted by water from Western larch wood, having galactose units and arabinose units in the approximate ratio of six to one.
Galactoarabinan is used in the following foods in the minimum quantity required to produce its intended effect as an emulsifier, stabilizer, binder, or bodying agent: Essential oils, nonnutritive sweeteners, flavor bases, nonstandardized dressings, and pudding mixes.

Commercial applications
Currently, Arabinogalactan is used in many ways. 
As an additive in food, animal feed, cosmetic, pharmacy, construction, pulp production, oil production, plant grow, etc. 
Arabinogalactan can be used as an additive in the way it is or in combination.
Research, biochemical enzyme assays and in vitro diagnostic analysis
For use as a dietary fiber standard
Arabinogalactan main use is as a replacement for gum arabic, guar gum, and starch in food, cosmetic and pharmaceutical products. 
Using Arabinogalactan leads to more efficient land distribution, leaving more land for agricultural purposes. 
Galactoarabinan plays an essential role in environment preservation, as manufacturers use non-polluting biorefinery processes.

What is Arabinogalactan?
Arabinogalactan is a natural compound found in many plants and a key ingredient in plant gums, such as gum arabic.
Certain species of bacteria have arabinogalactan in their cell walls for structural support.
A major commercial source of arabinogalactan is the North American larch tree. Extracts from this tree are referred to as larch arabinogalactan.
Arabinogalactan has several unique properties, including high solubility and stability. 
This makes Galactoarabinan useful as a thickening and stabilizing agent.
There is some evidence that arabinogalactan may have several health benefits such as improving the immune system and cholesterol levels. 
However, it’s not clear how strong these health claims are due to a lack of clinical research.

Food Sources
Varying concentrations of arabinogalactan are contained in the seeds, leaves, roots, fruit, and sap of many plants, including:
Leek seeds
Radish
Carrots
Pears
Maize
Wheat
Tomatoes

Arabinogalactan is also found in several medicinal herbs, such as:
Echinacea
Turmeric
Wild indigo
Angelica acutiloba
Terminalia arjuna
Commercially, arabinogalactan is typically extracted from the North American larch tree. 
This specific larch species contains a very high concentration (up to 35%) of arabinogalactan.

What Does Arabinogalactan Contain?
Arabinogalactan is a polysaccharide, meaning Galactoarabinan is made up of many smaller sugar molecules. 
More specifically, Galactoarabinan contains long chains of the sugars arabinose and galactose, which is how arabinogalactan got name.
The composition of these sugars can vary depending on the species of plant. For example, larch arabinogalactan contains galactose and arabinose in a 6:1 ratio.
Arabinogalactan is also commonly found in combination with proteins. Research is finding that arabinogalactan-proteins have their own unique functions in plants.
This means that different sources of arabinogalactan can have different concentrations of sugars and other compounds. 
This is important because researchers often use different plant sources for their studies, which can complicate their results.

How Does Arabinogalactan Work?
Arabinogalactan primarily works as a dietary fiber. 
Humans lack the enzymes to break down arabinogalactan, making arabinogalactan difficult to digest.
When arabinogalactan is consumed, arabinogalactan sits in the colon and is slowly fermented by the bacteria there. 
This fermentation produces short-chain fatty acids (SCFA), such as butyrate, which play an important role in colon health. 
For example, butyrate acts as an energy source for colon cells [7, 8].
Arabinogalactan may also interact with M-cells. 
These M-cells are part of the gut-associated lymphoid tissue, a system that plays an important role in the immune response in the digestive tract.
According to some researchers, arabinogalactan molecules may stimulate M-cells, which go on to activate T cells, B cells, and other cells of the immune system. 
This way, gut immunity potentially extends to affect whole-body immunity.

USES & EFFECTIVENESS
High cholesterol. 
Early research shows that taking larch arabinogalactan does not lower total cholesterol, low-density lipoprotein (LDL or “bad”) cholesterol, other blood fats called triglycerides, body weight, blood pressure, or sugar levels in healthy people. 
It is not yet known whether larch arabinogalactan improves these outcomes in people with high cholesterol.
Pneumonia. 
Early research shows that taking a specific larch arabinogalactan product (ResistAid) increases the immune system response to shots (vaccines) used to prevent pneumonia in healthy adults.
Common cold.
Flu.
H1N1 (swine) flu.
Liver disease.
Liver cancer.
Earache (otitis media).
HIV/AIDS.
Dietary fiber supplementation.
Boosting the immune system.
Inflammation.
Other conditions.

Structure of microbial arabinogalactan
Structure of arabinogalactan
The reducing end of microbial arabinogalactan consists of the terminal sequence →5)-D-Galf-(1→4)-L-Rhap-(1→3)-D-GlcNAc[citation needed]. 
A muramyl-6-P is also found within the peptidoglycan functional group. 
The mycolylarabinogalactan of mycobacteria is attached to the peptidoglycan by the actinomycete-specific diglycosylphosphoryl bridge, L-Rhap-(1→3)-D-GlcNAc-(1→P).

Arabinogalactan contains a galactan chain, with alternating 5-linked β-D-galactofuranosyl (Galf) and 6-linked β-D-Galf residues. 
The arabinan chains are attached to C-5 of some of the 6-linked Galf residues. 
There are three major structural domains for arabinan. The first is a domain consisting of linear 5-linked α-D-Araf residues. 
The second is a domain with branched 3,5 linked α-D-Araf residues substituted with 5-linked α-D-Araf units at both branched positions, and the third is A terminal non-reducing domain for end arabinan consisting of a 3,5-linked α-D-Araf residue substituted at both branched positions with the disaccharide β-D Araf-(1→2)- α-D-Araf. 
These three arabinan chains are attached to the galactan at residues 8, 10, and 12.

The non-reducing end of arabinogalactan is covalently attached to the mycolic acids of the outer membrane. 
The hydrophobicity of mycolic acids is a barrier to drug entry. 
Additionally, the mycolyl arabinogalactan peptidoglycan is responsible for aspects of disease pathogenesis and much of the antibody response in infections. 
The mycolyl substituents are selectively and equally distributed on the 5-hydroxyl functions of terminal- and the penultimate 2-linked Araf residues. 
The mycolyl residues are clustered in groups of four on the non reducing terminal pentaarabinosyl unit (β-Araf-(1→2)-α-Araf)2-3,5-α-Araf . 
Thus, the majority (66%) of the pentaarabinosyl units are substituted by mycolic acids, leaving the minority (33%) available for interaction with the immune system.
Approximately one of the three arabinosyl chains attached to the galactan chain contains succinyl groups. 
Although one succinyl group is most common, up to three succinyl groups per released arabinan fragment can be found on oligo-arabinans. 
However, arabinan fragments substituted with GalNH2 are not succinylated. 
Importantly, in the case of M. tuberculosis, and most likely in all slow growing organisms, both positive charge (protonated GalNH2 as GalNH3+) and negative charge (succinyl) are present in the middle regions of the arabinan, specifically at O-2 of the inner 3,5-α-D-Araf units. 
The succinyl residues are on the non-mycolylated chain. Recently, a complete primary model of arabinogalactan has been proposed.

Overview
Arabinogalactan is a starch-like chemical that is found in many plants. 
Arabinogalactan is found in highest concentrations in larch trees. 
Most of the larch arabinogalactan found in stores is produced from western larch or eastern larch trees. 
But larch arabinogalactan can also be produced by other larch tree species. Larch arabinogalactan is sometimes used for medicine.
Larch arabinogalactan is used for common cold, flu (influenza), ear infection (otitis media), and many other conditions, but there is no good scientific evidence to support its use.
In foods, larch arabinogalactan is used as a stabilizer, binder, and sweetener.

How does arabinogalactan work ?
Larch arabinogalactan is a fiber that ferments in the intestine. 
It might increase intestinal bacteria, such as Lactobacillus, and have other effects that could be beneficial to digestive tract health. 
There is also information that suggests larch arabinogalactan might boost the immune system and help prevent cancer cells in the liver from growing.

About Arabinogalactan
Prebiotic fiber for GI and immune support derived from the larch tree.
Arabinogalactan is a starch-like fiber found in many plants, and is in highest concentrations in larch trees. 
Larch arabinogalactans possess important immune-enhancing properties and are an excellent source of prebiotic fiber.

The Thorne Difference
arabinogalactan is a patented larch arabinogalactan that is used in Thorne products. 
Arabinogalactan is produced by steam-heating larch wood chips to extract the phenolic and arabinogalactan compounds and then drying the resulting extract. 
This patented extraction method is unique because it requires no harsh chemicals to release the compounds from the wood matrix, and it means the product remains pure and is structurally unaltered post-extraction.

Description and Biochemistry
Pharmaceutical-grade larch arabinogalactan is a fine, dry, off-white powder with a slightly sweet taste and mild pine-like odour. 
Galactoarabinan dissolves completely in water or juice, is low in viscosity and therefore easy to administer, even to children. 
Galactoarabinan is composed of galactose and arabinose molecules in a 6:1 ratio, with a small amount of glucuronic acid. 
Arabinogalactans are long, densely branched polysaccharides of varying molecular weights (10,000-120,000).  
Lower molecular weight polysaccharides typically exhibit an anti-inflammatory, anti-complement, anti-allergy effect, while those of higher weights stimulate natural killer (NK) cell cytotoxicity and reticuloendothelial cells. 
In the case of larch arabinogalactan, molecular weights of the two major fractions are 16,000 and 100,000, perhaps accounting for its wide range of therapeutic properties.

Pharmacokinetics
Human studies on the pharmacokinetics of Galactoarabinan are scarce and the amount absorbed following an oral dose remains unclear. 
Animal studies indicate that intravenous injection of purified larch arabinogalactan results in 52.5% of the dose being present in the liver and 30% in the urine 90 minutes after dosing. Hepatic clearance occurred with a half-life of 3.42 days.
Non-absorbed Galactoarabinan is actively fermented by intestinal microflora and is particularly effective at increasing beneficial anaerobes such as Bifidobacteria and Lactobacillus.

Computed Properties    
Molecular Weight: 500.5    
XLogP3-AA: -4.2    
Hydrogen Bond Donor Count: 7    
Hydrogen Bond Acceptor Count:  14    
Rotatable Bond Count: 8    
Exact Mass: 500.21050582    
Monoisotopic Mass: 500.21050582    
Topological Polar Surface Area: 206 Ų    
Heavy Atom Count: 34    
Formal Charge: 0    
Complexity: 626    
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 0    
Undefined Atom Stereocenter Count: 14    
Defined Bond Stereocenter Count: 0    
Undefined Bond Stereocenter Count: 0    
Covalently-Bonded Unit Count: 1    
Compound Is Canonicalized: Yes    

Application:
(+)-Arabinogalactan is an excellent dietary fiber
CAS Number:9036-66-2
Purity:≥99%
Molecular Weight:500.50
Molecular Formula:C20H36O14

Description
Free flowing powder    
Colour: White to light brown
Odour: Organoleptic    

Characteristics
Bulk density: 0.27 - 0.40 g/mL
Viscosity (30%):  2.2.8    ≤ 15 mPas
Loss on drying:  2.2.32    ≤ 6.0%
Solubility in water: Freely soluble in water

Identification
Test 1: IR        
Test 2: 1H-NMR    NMR
Assay
Polysaccharides (as arabinogalactan): HPLC ≥ 85.0%

Dietary Fiber
Larch arabinogalactan is an excellent source of dietary fiber that is able to increase short-chain fatty acid production (primarily butyrate) via its vigorous fermentation by intestinal microflora. 
It is well documented that butyrate is essential for proper colon health, as Galactoarabinan is the preferred substrate for energy generation by colonic epithelial cells. 
Butyrate also acts as a protectant for the intestinal mucosa against disease and cancer-promoting agents. 
Larch arabinogalactan given to human subjects increased levels of beneficial intestinal anaerobes, particularly Bifidobacterium longum, via their fermentation specificity for arabinogalactan compared to other complex carbohydrates.

Cancer Adjunct
Larch arabinogalactan may be an effective adjunct to cancer therapies due to Galactoarabinan's ability to stimulate NK cell cytotoxicity, stimulate the immune system, and block metastasis of tumor cells to the liver. 
Tumor metastasis to the liver is more common than to other organ sites, probably due to tumor cell specificity for lectin-like receptor sites found in liver parenchyma. 
Animal studies have demonstrated arabinogalactan’s ability to inhibit or block lectin receptor Larch Arabinogalactan sites, thereby reducing tumor cell colonization of the liver and also increasing survival time of the subjects. 
Pretreatment with larch arabinogalactan was found to stimulate NK cell cytotoxicity via potentiation of the cytokine network, primarily via an increase in the release of gamma interferon.

Pediatric Otitis Media
Recurrent otitis media is common in pediatric populations and it appears that improving immune system function might lead to a decrease in both frequency and severity of this condition.
Research has demonstrated larch and other arabinogalactans to be capable of enhancing the immune response to bacterial infection via stimulation of phagocytosis, competitive binding of bacterial fimbriae, or bacterial opsonization. 
This was found to be particularly true for infection by gram negative organisms such as Escherichia coli and Klebsiella species. 
In addition, a decrease in occurrence and severity of otitis media in pediatric patients supplemented prophylactically with larch arabinogalactan. 
Larch arabinogalactan’s mild taste and excellent solubility in water and juice make Galactoarabinan a relatively easy therapeutic tool to employ in pediatric populations.

TECHNICAL DATA
CAS No:    9036-66-2
Product Code:    YL29121
MDL No:    MFCD00062638
Shipping temperature: ambient
Storage temperature: ambient
CAS: 9036-66-2
Physical form: powder
Purity: > 95%
Molecular weight: 47,000
Source: larch tree
Monosaccharides (%) : galactose: arabinose: other sugars = 81: 14: 5
Main chain glycosidic linkage: α-1,5
Viscosity: ~ 0,1 cSt
Substrate for enzyme: endo-1,3-β-galactanase
Stability: > 10 years under recommended storage conditions

What is Arabinogalactan?
While Arabinogalactan and Arabinogalactan's constituent parts are common in nature, the commercial extraction is taken from a Larch Tree. 
Larch Trees are native to most colder parts of the Northern Hemisphere. 
Arabinogalactan is common in Europe, but rarely found in the US.  
Larch Arabinogalactan is so mild and has so many benefits, we use Arabinogalactan as a natural and beneficial base and binder in many of our products, as well as offer Arabinogalactan as a single ingredient product. 

THE MANY BENEFITS OF ARABINOGALACTAN
Arabinogalactan has so many benefits. 
Arabinogalactan is a water soluble fiber, a prebiotic, and a supporter of immune competence. 
Arabinogalactan is a long chain polysaccharides containing arabinose and galactose mono-saccharides. 
Larch Arabinogalactan is a fiber-rich complex carbohydrate that ferments in the intestine. 
Arabinogalactan might increase intestinal bacteria, such as Lactobacillus, and have other effects that could be beneficial to digestive tract health. 
Arabinogalactan is actively fermented by intestinal micro-flora and is effective at increasing beneficial anaerobes such as those in Pet Flora.
There is also information that suggests larch Arabinogalactan might boost the immune system and help prevent cancer cells in the liver from growing. 
Many alternative medicine practitioners believe it can protect against common and uncommon infections.
Arabinogalactan is thought to stimulate the immune system by increasing the amount of probiotic bacteria in the gut as it undergoes fermentation. 
For reasons not entirely understood, this action triggers a dramatic increase in defensive antibodies, including immunoglobulin G (IgG), as well as inflammatory proteins such as tumor necrosis factor (TNF).
You can find Arabinogalactan in most of Vitality Science’s products or you could buy it separately to add to food or water. 

Synonyms    
Galactoarabinan
9036-66-2
(+)-Arabinogalactan
(+)-Arabinogalactan from Larch Wood,
ARABINOGALACTAN
4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol
Larch arabinogalactan
YL29121
FT-0604415