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Bile (from Latin ''bilis''), or gall, is a dark-green-to-yellowish-brown fluid produced by the liver of most vertebrates that aids the
digestion Digestion is the breakdown of large insoluble food molecules into small water-soluble food molecules so that they can be absorbed into the watery blood plasma. In certain organisms, these smaller substances are absorbed through the small intes ...
of lipids in the
small intestine The small intestine or small bowel is an organ in the gastrointestinal tract where most of the absorption of nutrients from food takes place. It lies between the stomach and large intestine, and receives bile and pancreatic juice through the ...
. In humans, bile is produced continuously by the liver (liver bile) and stored and concentrated in the
gallbladder In vertebrates, the gallbladder, also known as the cholecyst, is a small hollow organ where bile is stored and concentrated before it is released into the small intestine. In humans, the pear-shaped gallbladder lies beneath the liver, altho ...
. After eating, this stored bile is discharged into the
duodenum The duodenum is the first section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear, and the terms anterior intestine or proximal intestine ...
. The composition of hepatic bile is (97–98)% water, 0.7%
bile salts Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary b ...
, 0.2%
bilirubin Bilirubin (BR) (Latin for "red bile") is a red-orange compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from t ...
, 0.51% fats (cholesterol, fatty acids, and
lecithin Lecithin (, from the Greek ''lekithos'' "yolk") is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances (and so ar ...
), and 200 meq/L inorganic salts. The two main pigments of bile are bilirubin, which is yellow, and its oxidised form
biliverdin Biliverdin ( latin for green bile) is a green tetrapyrrolic bile pigment, and is a product of heme catabolism.Boron W, Boulpaep E. Medical Physiology: a cellular and molecular approach, 2005. 984-986. Elsevier Saunders, United States. It is the ...
, which is green. When mixed, they are responsible for the brown color of feces. About 400 to 800 millilitres of bile is produced per day in adult human beings.


Function

Bile or gall acts to some extent as a surfactant, helping to
emulsify An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althoug ...
the lipids in food. Bile salt
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
s are
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are no ...
on one side and
hydrophobic In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, t ...
on the other side; consequently, they tend to aggregate around droplets of lipids ( triglycerides and
phospholipid Phospholipids, are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
s) to form
micelle A micelle () or micella () (plural micelles or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension (also known as associated coll ...
s, with the hydrophobic sides towards the fat and hydrophilic sides facing outwards. The hydrophilic sides are negatively charged, and this charge prevents fat droplets coated with bile from re-aggregating into larger fat particles. Ordinarily, the micelles in the duodenum have a diameter around 1–50 μm in humans. The dispersion of food fat into micelles provides a greatly increased surface area for the action of the enzyme pancreatic lipase, which digests the triglycerides, and is able to reach the fatty core through gaps between the bile salts. A triglyceride is broken down into two fatty acids and a monoglyceride, which are absorbed by the villi on the intestine walls. After being transferred across the intestinal membrane, the fatty acids reform into triglycerides (re-esterified), before being absorbed into the lymphatic system through
lacteal A lacteal is a lymphatic capillary that absorbs dietary fats in the villi of the small intestine. Triglycerides are emulsified by bile and hydrolyzed by the enzyme lipase, resulting in a mixture of fatty acids, di- and monoglycerides. These ...
s. Without bile salts, most of the lipids in food would be excreted in feces, undigested. Since bile increases the absorption of fats, it is an important part of the absorption of the fat-soluble substances, such as the vitamins A, D, E, and K. Besides its digestive function, bile serves also as the route of excretion for bilirubin, a byproduct of
red blood cells Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...
recycled by the liver. Bilirubin derives from hemoglobin by glucuronidation. Bile tends to be
alkaline In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a basic, ionic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of ...
on average. The pH of common duct bile (7.50 to 8.05) is higher than that of the corresponding gallbladder bile (6.80 to 7.65). Bile in the gallbladder becomes more
acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
ic the longer a person goes without eating, though resting slows this fall in pH. As an alkali, it also has the function of neutralizing excess
stomach acid Gastric acid, gastric juice, or stomach acid is a digestive fluid formed within the stomach lining. With a pH between 1 and 3, gastric acid plays a key role in digestion of proteins by activating digestive enzymes, which together break down the ...
before it enters the
duodenum The duodenum is the first section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear, and the terms anterior intestine or proximal intestine ...
, the first section of the
small intestine The small intestine or small bowel is an organ in the gastrointestinal tract where most of the absorption of nutrients from food takes place. It lies between the stomach and large intestine, and receives bile and pancreatic juice through the ...
. Bile
salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...
also act as
bactericide A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their ...
s, destroying many of the microbes that may be present in the food.


Clinical significance

In the absence of bile, fats become indigestible and are instead excreted in feces, a condition called
steatorrhea Steatorrhea (or steatorrhoea) is the presence of excess fat in feces. Stools may be bulky and difficult to flush, have a pale and oily appearance, and can be especially foul-smelling. An oily anal leakage or some level of fecal incontinence may o ...
. Feces lack their characteristic brown color and instead are white or gray, and greasy. Steatorrhea can lead to deficiencies in essential fatty acids and
fat-soluble vitamins A vitamin is an organic molecule (or a set of molecules closely related chemically, i.e. vitamers) that is an essential micronutrient that an organism needs in small quantities for the proper functioning of its metabolism. Essential nutrien ...
. In addition, past the
small intestine The small intestine or small bowel is an organ in the gastrointestinal tract where most of the absorption of nutrients from food takes place. It lies between the stomach and large intestine, and receives bile and pancreatic juice through the ...
(which is normally responsible for absorbing fat from food) the gastrointestinal tract and
gut flora Gut microbiota, gut microbiome, or gut flora, are the microorganisms, including bacteria, archaea, fungi, and viruses that live in the digestive tracts of animals. The gastrointestinal metagenome is the aggregate of all the genomes of the gut m ...
are not adapted to processing fats, leading to problems in the large intestine. The cholesterol contained in bile will occasionally accrete into lumps in the gallbladder, forming
gallstones A gallstone is a stone formed within the gallbladder from precipitated bile components. The term cholelithiasis may refer to the presence of gallstones or to any disease caused by gallstones, and choledocholithiasis refers to the presence of migr ...
. Cholesterol gallstones are generally treated through surgical removal of the gallbladder. However, they can sometimes be dissolved by increasing the concentration of certain naturally occurring bile acids, such as
chenodeoxycholic acid Chenodeoxycholic acid (CDCA; also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the mai ...
and ursodeoxycholic acid. On an empty stomach – after repeated vomiting, for example – a person's vomit may be green or dark yellow, and very bitter. The bitter and greenish component may be bile or normal digestive juices originating in the stomach. Bile may be forced into the stomach secondary to a weakened valve (
pylorus The pylorus ( or ), or pyloric part, connects the stomach to the duodenum. The pylorus is considered as having two parts, the ''pyloric antrum'' (opening to the body of the stomach) and the ''pyloric canal'' (opening to the duodenum). The ''pylori ...
), the presence of certain drugs including
alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...
, or powerful muscular contractions and duodenal spasms. This is known as
biliary reflux Biliary reflux, bile reflux (gastritis), duodenogastroesophageal reflux (DGER) or duodenogastric reflux is a condition that occurs when bile and/or other contents like bicarbonate, and pancreatic enzymes flow upward (refluxes) from the duodenum in ...
.


Obstruction

Biliary obstruction refers to a condition when
bile duct A bile duct is any of a number of long tube-like structures that carry bile, and is present in most vertebrates. Bile is required for the digestion of food and is secreted by the liver into passages that carry bile toward the hepatic duct. ...
s which deliver bile from the gallbladder or liver to the
duodenum The duodenum is the first section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear, and the terms anterior intestine or proximal intestine ...
become obstructed. The blockage of bile might cause a buildup of
bilirubin Bilirubin (BR) (Latin for "red bile") is a red-orange compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from t ...
in the
bloodstream The blood circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the entire body of a human or other vertebrate. It includes the cardiovascular system, or vascular system, t ...
which can result in
jaundice Jaundice, also known as icterus, is a yellowish or greenish pigmentation of the skin and sclera due to high bilirubin levels. Jaundice in adults is typically a sign indicating the presence of underlying diseases involving abnormal heme meta ...
. There are several potential causes for biliary obstruction including gallstones, cancer, trauma,
choledochal cysts Choledochal cysts (a.k.a. bile duct cyst) are congenital conditions involving cystic dilatation of bile ducts. They are uncommon in western countries but not as rare in East Asian nations like Japan and China. Signs and symptoms Most patients ha ...
, or other benign causes of bile duct narrowing. The most common cause of bile duct obstruction is when gallstone(s) are dislodged from the gallbladder into the cystic duct or common bile duct resulting in a blockage. A blockage of the gallbladder or
cystic duct The cystic duct is the short duct that joins the gallbladder to the common hepatic duct. It usually lies next to the cystic artery. It is of variable length. It contains 'spiral valves of Heister', which do not provide much resistance to the ...
may cause
cholecystitis Cholecystitis is inflammation of the gallbladder. Symptoms include right upper abdominal pain, pain in the right shoulder, nausea, vomiting, and occasionally fever. Often gallbladder attacks (biliary colic) precede acute cholecystitis. The pain l ...
. If the blockage is beyond the confluence of the pancreatic duct, this may cause gallstone pancreatitis. In some instances of biliary obstruction, the bile may become infected by bacteria resulting in
ascending cholangitis Ascending cholangitis, also known as acute cholangitis or simply cholangitis, is inflammation of the bile duct, usually caused by bacteria ascending from its junction with the duodenum (first part of the small intestine). It tends to occur if t ...
.


Society and culture

In medical theories prevalent in the West from Classical Antiquity to the Middle Ages, the body's health depended on the equilibrium of four "humors", or vital fluids, two of which related to bile: blood,
phlegm Phlegm (; , ''phlégma'', "inflammation", " humour caused by heat") is mucus produced by the respiratory system, excluding that produced by the nasal passages. It often refers to respiratory mucus expelled by coughing, otherwise known as sput ...
, "yellow bile" (choler), and "black bile". These "humors" are believed to have their roots in the appearance of a blood sedimentation test made in open air, which exhibits a dark clot at the bottom ("black bile"), a layer of unclotted erythrocytes ("blood"), a layer of white blood cells ("phlegm") and a layer of clear yellow serum ("yellow bile"). Excesses of black bile and yellow bile were thought to produce depression and aggression, respectively, and the Greek names for them gave rise to the English words
cholera Cholera is an infection of the small intestine by some strains of the bacterium ''Vibrio cholerae''. Symptoms may range from none, to mild, to severe. The classic symptom is large amounts of watery diarrhea that lasts a few days. Vomiting and ...
(from Greek χολή ''kholē'', "bile") and melancholia. In the former of those senses, the same theories explain the derivation of the English word bilious from ''bile'', the meaning of gall in English as "exasperation" or "impudence", and the Latin word ''cholera'', derived from the Greek ''kholé'', which was passed along into some Romance languages as words connoting anger, such as '' colère'' (French) and ''cólera'' (Spanish).


Soap

Soap can be mixed with bile from mammals, such as
ox gall Ox gall is gall, usually obtained from cows, that is an ingredient in bile soap and mixed with alcohol and used as the wetting agent in paper marbling, engraving, lithography, and watercolor painting. It is a greenish-brown liquid mixture cont ...
. This mixture, called bile soap or gall soap, can be applied to textiles a few hours before washing as a traditional and effective method for removing various kinds of tough stains.


Food

"Pinapaitan" is a dish in
Philippine cuisine Filipino cuisine ( fil, lutong Pilipino/pagkaing Pilipino) is composed of the cuisines of more than a hundred distinct ethnolinguistic groups found throughout the Philippine archipelago. A majority of mainstream Filipino dishes that compose F ...
that uses bile as flavoring. Other areas where bile is commonly used as a cooking ingredient include Laos and northern parts of Thailand.


Bears

In regions where bile products are a popular ingredient in
traditional medicine Traditional medicine (also known as indigenous medicine or folk medicine) comprises medical aspects of traditional knowledge that developed over generations within the folk beliefs of various societies, including indigenous peoples, before the ...
, the use of bears in bile-farming has been widespread. This practice has been condemned by activists, and some pharmaceutical companies have developed synthetic (non-ursine) alternatives.


Principal acids

Image:Cholic acid.svg,
Cholic acid Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Chol ...
Image:Chenodeoxycholic acid.svg,
Chenodeoxycholic acid Chenodeoxycholic acid (CDCA; also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the mai ...
Image:Glycocholsäure.svg,
Glycocholic acid Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine Glycine (symbol Gly or G; ) is an amino ...
Image:Taurocholic acid.svg,
Taurocholic acid Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate ...
Image:Deoxycholic acid.svg, Deoxycholic acid Image:Lithocholic_acid_acsv.svg,
Lithocholic acid Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydrox ...


See also

*
Bile acid sequestrant The bile acid sequestrants are a group of resins used to bind certain components of bile in the gastrointestinal tract. They disrupt the enterohepatic circulation of bile acids by combining with bile constituents and preventing their reabsorption fr ...
*
Enterohepatic circulation Enterohepatic circulation refers to the circulation of biliary acids, bilirubin, drugs or other substances from the liver to the bile, followed by entry into the small intestine, absorption by the enterocyte and transport back to the liver. Ent ...
*
Intestinal juice In histology, an intestinal gland (also crypt of Lieberkühn and intestinal crypt) is a gland found in between villi in the intestinal epithelium lining of the small intestine and large intestine (or colon). The glands and intestinal villi are co ...


References

Seleem HM, Nada AS, Naguib MA, Abdelmaksoud OR, El-Gazzarah AR. Serum immunoglobulin G4 in patients with nonmalignant common bile duct stricture. Menoufia Med J erial online2021 ited 2022 Jan 2134:1275-83. Available from: http://www.mmj.eg.net/text.asp?2021/34/4/1275/333263


Bibliography

* * * {{Authority control Body fluids Digestive system Biomolecules Hepatology