carbohydrate

In scientific literature, the term "carbohydrate" has many synonyms, like "sugar" (in the broad sense), "saccharide", "ose", "glucide",{{cite book | vauthors = Fearon WF | year = 1949 | title = Introduction to Biochemistry | edition = 2nd | location = London | publisher = Heinemann | url = https://books.google.com/books?id=YkOaBQAAQBAJ | isbn = 978-1483225395 | access-date = November 30, 2017 | archive-date = July 27, 2020 | archive-url = https://web.archive.org/web/20200727175530/https://books.google.com/books?id=YkOaBQAAQBAJ | url-status = live }} "hydrate of carbon" or "polyhydroxy compounds with aldehyde or ketone". Some of these terms, especially "carbohydrate" and "sugar", are also used with other meanings.

In food science and in many informal contexts, the term "carbohydrate" often means any food that is particularly rich in the complex carbohydrate starch (such as cereals, bread and pasta) or simple carbohydrates, such as sugar (found in candy, jams, and desserts). This informality is sometimes confusing since it confounds chemical structure and digestibility in humans.

The term "carbohydrate" (or "carbohydrate by difference") refers also to dietary fiber, which is a carbohydrate, but, unlike sugars and starches, fibers are not hydrolyzed by human digestive enzymes. Fiber generally contributes little food energy in humans, but is often included in the calculation of total food energy. The fermentation of soluble fibers by gut microflora can yield short-chain fatty acids, and soluble fiber is estimated to provide about 2 kcal/g.

{{Expand section|date=January 2022}}

The history of the discovery regarding carbohydrates dates back around 10,000 years ago in Papua New Guinea during the cultivation of sugarcane during the Neolithic agricultural revolution.{{Cite journal |last=Denham |first=Tim |date=October 2011 |title=Early Agriculture and Plant Domestication in New Guinea and Island Southeast Asia |url=https://www.journals.uchicago.edu/doi/10.1086/658682 |journal=Current Anthropology |volume=52 |issue=54 |pages=S161–S512 |doi=10.1086/658682 |issn=0011-3204 |via=The University of Chicago Press Journals}} The term "carbohydrate" was first proposed by German chemist Carl Schmidt (chemist) in 1844. In 1856, glycogen, a form of carbohydrate storage in animal livers, was discovered by French physiologist Claude Bernard.{{Cite journal |last=Young |first=F. G. |date=1957-06-22 |title=Claude Bernard and the Discovery of Glycogen |journal=British Medical Journal |volume=1 |issue=5033 |pages=1431–1437 |doi=10.1136/bmj.1.5033.1431 |issn=0007-1447 |pmc=1973429 |pmid=13436813}}

Formerly the name "carbohydrate" was used in chemistry for any compound with the formula C_m (H₂O)_n. Following this definition, some chemists considered formaldehyde (CH₂O) to be the simplest carbohydrate,{{cite book | vauthors = Coulter JM, Barnes CR, Cowles HC | year = 1930 | url = https://books.google.com/books?id=WyZnVpCiTHIC&q=simplest+carbohydrate&pg=PA375 | title = A Textbook of Botany for Colleges and Universities | publisher = BiblioBazaar | isbn = 978-1113909954 | access-date = April 24, 2022 | archive-date = April 17, 2022 | archive-url = https://web.archive.org/web/20220417005854/https://books.google.com/books?id=WyZnVpCiTHIC&q=simplest+carbohydrate&pg=PA375 | url-status = live }} while others claimed that title for glycolaldehyde.{{cite book | vauthors = Burtis CA, Ashwood ER, Tietz NW | year = 2000 | url = https://books.google.com/books?id=l5hqAAAAMAAJ&q=simplest+carbohydrate | title = Tietz fundamentals of clinical chemistry | publisher = W.B. Saunders | isbn = 9780721686349 | access-date = January 8, 2016 | archive-date = June 24, 2016 | archive-url = https://web.archive.org/web/20160624073749/https://books.google.com/books?id=l5hqAAAAMAAJ&q=simplest+carbohydrate | url-status = live }} Today, the term is generally understood in the biochemistry sense, which excludes compounds with only one or two carbons and includes many biological carbohydrates which deviate from this formula. For example, while the above representative formulas would seem to capture the commonly known carbohydrates, ubiquitous and abundant carbohydrates often deviate from this. For example, carbohydrates often display chemical groups such as: N-acetyl (e.g., chitin), sulfate (e.g., glycosaminoglycans), carboxylic acid and deoxy modifications (e.g., fucose and sialic acid).

Natural saccharides are generally built of simple carbohydrates called monosaccharides with general formula (CH₂O)_n where n is three or more. A typical monosaccharide has the structure H–(CHOH)_x(C=O)–(CHOH)_y–H, that is, an aldehyde or ketone with many hydroxyl groups added, usually one on each carbon atom that is not part of the aldehyde or ketone functional group. Examples of monosaccharides are glucose, fructose, and glyceraldehydes. However, some biological substances commonly called "monosaccharides" do not conform to this formula (e.g., uronic acids and deoxy-sugars such as fucose) and there are many chemicals that do conform to this formula but are not considered to be monosaccharides (e.g., formaldehyde CH₂O and inositol (CH₂O)₆).{{cite book | vauthors = Matthews CE, Van Holde KE, Ahern KG | year = 1999 | title = Biochemistry | edition = 3rd | publisher = Benjamin Cummings | isbn = 978-0-8053-3066-3 }}{{page needed|date=January 2018}}

The open-chain form of a monosaccharide often coexists with a closed ring form where the aldehyde/ketone carbonyl group carbon (C=O) and hydroxyl group (–OH) react forming a hemiacetal with a new C–O–C bridge.

Monosaccharides can be linked together into what are called polysaccharides (or oligosaccharides) in a large variety of ways. Many carbohydrates contain one or more modified monosaccharide units that have had one or more groups replaced or removed. For example, deoxyribose, a component of DNA, is a modified version of ribose; chitin is composed of repeating units of N-acetyl glucosamine, a nitrogen-containing form of glucose.

Carbohydrates are polyhydroxy aldehydes, ketones, alcohols, acids, their simple derivatives and their polymers having linkages of the acetal type. They may be classified according to their degree of polymerization, and may be divided initially into three principal groups, namely sugars, oligosaccharides and polysaccharides.{{cite book | title = Carbohydrates in human nutrition | series = FAO Food and Nutrition Paper – 66 | chapter = Chapter 1 – The role of carbohydrates in nutrition | chapter-url = http://www.fao.org/docrep/w8079e/w8079e07.htm | publisher = Food and Agriculture Organization of the United Nations | access-date = December 21, 2015 | archive-date = December 22, 2015 | archive-url = https://web.archive.org/web/20151222095451/http://www.fao.org/docrep/w8079e/w8079e07.htm | url-status = live }}

{{Main|Monosaccharide}}

Image:D-glucose color coded.png is an aldohexose with the formula (C·H₂O)₆. The red atoms highlight the aldehyde group and the blue atoms highlight the asymmetric center furthest from the aldehyde; because this -OH is on the right of the Fischer projection, this is a D sugar.]]

Monosaccharides are the simplest carbohydrates in that they cannot be hydrolyzed to smaller carbohydrates. They are aldehydes or ketones with two or more hydroxyl groups. The general chemical formula of an unmodified monosaccharide is (C•H₂O)_n, literally a "carbon hydrate". Monosaccharides are important fuel molecules as well as building blocks for nucleic acids. The smallest monosaccharides, for which n=3, are dihydroxyacetone and D- and L-glyceraldehydes.

Monosaccharides are classified according to three different characteristics: the placement of its carbonyl group, the number of carbon atoms it contains, and its chiral handedness. If the carbonyl group is an aldehyde, the monosaccharide is an aldose; if the carbonyl group is a ketone, the monosaccharide is a ketose. Monosaccharides with three carbon atoms are called trioses, those with four are called tetroses, five are called pentoses, six are hexoses, and so on.{{cite book | vauthors = Campbell NA, Williamson B, Heyden RJ | title = Biology: Exploring Life | publisher = Pearson Prentice Hall | year = 2006 | location = Boston, Massachusetts | url = http://www.phschool.com/el_marketing.html | isbn = 978-0-13-250882-7 | access-date = December 2, 2008 | archive-date = November 2, 2014 | archive-url = https://web.archive.org/web/20141102041816/http://www.phschool.com/el_marketing.html | url-status = live }} These two systems of classification are often combined. For example, glucose is an aldohexose (a six-carbon aldehyde), ribose is an aldopentose (a five-carbon aldehyde), and fructose is a ketohexose (a six-carbon ketone).

Each carbon atom bearing a hydroxyl group (-OH), with the exception of the first and last carbons, are asymmetric, making them stereo centers with two possible configurations each (R or S). Because of this asymmetry, a number of isomers may exist for any given monosaccharide formula. Using Le Bel-van't Hoff rule, the aldohexose D-glucose, for example, has the formula (C·H₂O)₆, of which four of its six carbons atoms are stereogenic, making D-glucose one of 2⁴=16 possible stereoisomers. In the case of glyceraldehydes, an aldotriose, there is one pair of possible stereoisomers, which are enantiomers and epimers. 1, 3-dihydroxyacetone, the ketose corresponding to the aldose glyceraldehydes, is a symmetric molecule with no stereo centers. The assignment of D or L is made according to the orientation of the asymmetric carbon furthest from the carbonyl group: in a standard Fischer projection if the hydroxyl group is on the right the molecule is a D sugar, otherwise it is an L sugar. The "D-" and "L-" prefixes should not be confused with "d-" or "l-", which indicate the direction that the sugar rotates plane polarized light. This usage of "d-" and "l-" is no longer followed in carbohydrate chemistry.{{cite book | vauthors = Pigman W, Horton D | title=The Carbohydrates: Chemistry and Biochemistry Vol 1A| veditors = Pigman W, Horton D |edition=2nd|year=1972|publisher=Academic Press|location=San Diego|pages=1–67|chapter=Chapter 1: Stereochemistry of the Monosaccharides|isbn=978-0323138338}}

Image:Glucose Fisher to Haworth.gif can exist in both a straight-chain and ring form.]]

The aldehyde or ketone group of a straight-chain monosaccharide will react reversibly with a hydroxyl group on a different carbon atom to form a hemiacetal or hemiketal, forming a heterocyclic ring with an oxygen bridge between two carbon atoms. Rings with five and six atoms are called furanose and pyranose forms, respectively, and exist in equilibrium with the straight-chain form.{{cite book | vauthors = Pigman W, Anet EF |title=The Carbohydrates: Chemistry and Biochemistry Vol 1A| veditors = Pigman W, Horton D |edition=2nd|year=1972|publisher=Academic Press|location=San Diego|pages=165–194|chapter=Chapter 4: Mutarotations and Actions of Acids and Bases|isbn=978-0323138338}}

During the conversion from straight-chain form to the cyclic form, the carbon atom containing the carbonyl oxygen, called the anomeric carbon, becomes a stereogenic center with two possible configurations: The oxygen atom may take a position either above or below the plane of the ring. The resulting possible pair of stereoisomers is called anomers. In the α anomer, the -OH substituent on the anomeric carbon rests on the opposite side (trans) of the ring from the CH₂OH side branch. The alternative form, in which the CH₂OH substituent and the anomeric hydroxyl are on the same side (cis) of the plane of the ring, is called the β anomer.{{cn|date=April 2025}}

Monosaccharides are the major fuel source for metabolism, and glucose is an energy-rich molecule utilized to generate ATP in almost all living organisms. Glucose is a high-energy substrate produced in plants through photosynthesis by combining energy-poor water and carbon dioxide in an endothermic reaction fueled by solar energy. When monosaccharides are not immediately needed, they are often converted to more space-efficient (i.e., less water-soluble) forms, often polysaccharides. In animals, glucose circulating the blood is a major metabolic substrate and is oxidized in the mitochondria to produce ATP for performing useful cellular work. In humans and other animals, serum glucose levels must be regulated carefully to maintain glucose within acceptable limits and prevent the deleterious effects of hypo- or hyperglycemia. Hormones such as insulin and glucagon serve to keep glucose levels in balance: insulin stimulates glucose uptake into the muscle and fat cells when glucose levels are high, whereas glucagon helps to raise glucose levels if they dip too low by stimulating hepatic glucose synthesis. In many animals, including humans, this storage form is glycogen, especially in liver and muscle cells. In plants, starch is used for the same purpose. The most abundant carbohydrate, cellulose, is a structural component of the cell wall of plants and many forms of algae. Ribose is a component of RNA. Deoxyribose is a component of DNA. Lyxose is a component of lyxoflavin found in the human heart.{{cite encyclopedia |title=lyxoflavin |url=http://www.merriam-webster.com/medical/lyxoflavin |dictionary=Merriam-Webster |access-date=February 26, 2014 |archive-date=October 31, 2014 |archive-url=https://web.archive.org/web/20141031135041/http://www.merriam-webster.com/medical/lyxoflavin |url-status=live }} Ribulose and xylulose occur in the pentose phosphate pathway. Galactose, a component of milk sugar lactose, is found in galactolipids in plant cell membranes and in glycoproteins in many tissues. Mannose occurs in human metabolism, especially in the glycosylation of certain proteins. Fructose, or fruit sugar, is found in many plants and humans, it is metabolized in the liver, absorbed directly into the intestines during digestion, and found in semen. Trehalose, a major sugar of insects, is rapidly hydrolyzed into two glucose molecules to support continuous flight.

Image:sucrose 3Dprojection.png, also known as table sugar, is a common disaccharide. It is composed of two monosaccharides: D-glucose (left) and D-fructose (right).]]

{{Main|Disaccharide}}

Two joined monosaccharides are called a disaccharide, the simplest kind of polysaccharide. Examples include sucrose and lactose. They are composed of two monosaccharide units bound together by a covalent bond known as a glycosidic linkage formed via a dehydration reaction, resulting in the loss of a hydrogen atom from one monosaccharide and a hydroxyl group from the other. The formula of unmodified disaccharides is C₁₂H₂₂O₁₁. Although there are numerous kinds of disaccharides, a handful of disaccharides are particularly notable.

Sucrose, pictured to the right, is the most abundant disaccharide, and the main form in which carbohydrates are transported in plants. It is composed of one D-glucose molecule and one D-fructose molecule. The systematic name for sucrose, O-α-D-glucopyranosyl-(1→2)-D-fructofuranoside, indicates four things:

• Its monosaccharides: glucose and fructose
• Their ring types: glucose is a pyranose and fructose is a furanose
• How they are linked together: the oxygen on carbon number 1 (C1) of α-D-glucose is linked to the C2 of D-fructose.
• The -oside suffix indicates that the anomeric carbon of both monosaccharides participates in the glycosidic bond.

Lactose, a disaccharide composed of one D-galactose molecule and one D-glucose molecule, occurs naturally in mammalian milk. The systematic name for lactose is O-β-D-galactopyranosyl-(1→4)-D-glucopyranose. Other notable disaccharides include maltose (two D-glucoses linked α-1,4) and cellobiose (two D-glucoses linked β-1,4). Disaccharides can be classified into two types: reducing and non-reducing disaccharides. If the functional group is present in bonding with another sugar unit, it is called a reducing disaccharide or biose.

{{main|Oligosaccharide}}

Oligosaccharides are saccharide polymers composed of three to ten units of monosaccharides, connected via glycosidic linkages, similar to disaccharides. They are usually linked to lipids or amino acids glycosic linkage with oxygen or nitrogen to form glycolipids and glycoproteins, though some, like the raffinose series and the fructooligosaccharides, do not. They have roles in cell recognition and cell adhesion.

File:FOS.svg]]

{{main|Polysaccharides}}

File:GrainProducts.jpg products: rich sources of carbohydrates]]

Carbohydrate consumed in food yields 3.87 kilocalories of energy per gram for simple sugars,{{cite web|url=http://ndb.nal.usda.gov/ndb/foods/show/6202|title=Show Foods|work=usda.gov|access-date=June 4, 2014|archive-date=October 3, 2017|archive-url=https://web.archive.org/web/20171003224558/https://ndb.nal.usda.gov/ndb/foods/show/6202|url-status=dead}} and 3.57 to 4.12 kilocalories per gram for complex carbohydrate in most other foods.{{cite web|url=http://www.fao.org/docrep/006/y5022e/y5022e04.htm|title=Calculation of the Energy Content of Foods – Energy Conversion Factors|work=fao.org|access-date=August 2, 2013|archive-date=May 24, 2010|archive-url=https://web.archive.org/web/20100524003622/http://www.fao.org/DOCREP/006/Y5022E/y5022e04.htm|url-status=live}} Relatively high levels of carbohydrate are associated with processed foods or refined foods made from plants, including sweets, cookies and candy, table sugar, honey, soft drinks, breads and crackers, jams and fruit products, pastas and breakfast cereals. Refined carbohydrates from processed foods such as white bread or rice, soft drinks, and desserts are readily digestible, and many are known to have a high glycemic index, which reflects a rapid assimilation of glucose. By contrast, the digestion of whole, unprocessed, fiber-rich foods such as beans, peas, and whole grains produces a slower and steadier release of glucose and energy into the body.{{cite web |url=https://www.diabetes.org.uk/upload/How%20we%20help/catalogue/carb-reference-list-0511.pdf |title=Carbohydrate reference list |website=www.diabetes.org.uk |access-date=October 30, 2016 |archive-date=March 14, 2016 |archive-url=https://web.archive.org/web/20160314193016/https://www.diabetes.org.uk/upload/how%20we%20help/catalogue/carb-reference-list-0511.pdf |url-status=dead }} Animal-based foods generally have the lowest carbohydrate levels, although milk does contain a high proportion of lactose.

Organisms typically cannot metabolize all types of carbohydrate to yield energy. Glucose is a nearly universal and accessible source of energy. Many organisms also have the ability to metabolize other monosaccharides and disaccharides but glucose is often metabolized first. In Escherichia coli, for example, the lac operon will express enzymes for the digestion of lactose when it is present, but if both lactose and glucose are present, the lac operon is repressed, resulting in the glucose being used first (see: Diauxie). Polysaccharides are also common sources of energy. Many organisms can easily break down starches into glucose; most organisms, however, cannot metabolize cellulose or other polysaccharides such as chitin and arabinoxylans. These carbohydrate types can be metabolized by some bacteria and protists. Ruminants and termites, for example, use microorganisms to process cellulose, fermenting it to caloric short-chain fatty acids. Even though humans lack the enzymes to digest fiber, dietary fiber represents an important dietary element for humans. Fibers promote healthy digestion, help regulate postprandial glucose and insulin levels, reduce cholesterol levels, and promote satiety.{{cite journal | vauthors = Pichon L, Huneau JF, Fromentin G, Tomé D | title = A high-protein, high-fat, carbohydrate-free diet reduces energy intake, hepatic lipogenesis, and adiposity in rats | journal = The Journal of Nutrition | volume = 136 | issue = 5 | pages = 1256–1260 | date = May 2006 | pmid = 16614413 | doi = 10.1093/jn/136.5.1256 | doi-access = free }}

The Institute of Medicine recommends that American and Canadian adults get between 45 and 65% of dietary energy from whole-grain carbohydrates.Food and Nutrition Board (2002/2005). [https://archive.today/20070210182833/http://newton.nap.edu/books/0309085373/html Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein and Amino Acids]. Washington, D.C.: The National Academies Press. Page [http://newton.nap.edu/books/0309085373/html/769.html 769] {{Webarchive|url=https://web.archive.org/web/20060912060636/http://newton.nap.edu/books/0309085373/html/769.html |date=September 12, 2006 }}. {{ISBN|0-309-08537-3}}. The Food and Agriculture Organization and World Health Organization jointly recommend that national dietary guidelines set a goal of 55–75% of total energy from carbohydrates, but only 10% directly from sugars (their term for simple carbohydrates).Joint WHO/FAO expert consultation (2003). [https://web.archive.org/web/20110423051140/http://www.who.int/hpr/NPH/docs/who_fao_expert_report.pdf] (PDF). Geneva: World Health Organization. pp. 55–56. {{ISBN|92-4-120916-X}}. A 2017 Cochrane Systematic Review concluded that there was insufficient evidence to support the claim that whole grain diets can affect cardiovascular disease.{{cite journal | vauthors = Kelly SA, Hartley L, Loveman E, Colquitt JL, Jones HM, Al-Khudairy L, Clar C, Germanò R, Lunn HR, Frost G, Rees K | display-authors = 6 | title = Whole grain cereals for the primary or secondary prevention of cardiovascular disease | journal = The Cochrane Database of Systematic Reviews | volume = 8 | issue = 8 | pages = CD005051 | date = August 2017 | pmid = 28836672 | pmc = 6484378 | doi = 10.1002/14651858.CD005051.pub3 | url = https://spiral.imperial.ac.uk:8443/bitstream/10044/1/54579/2/Kelly_et_al-2017-.pdf | access-date = September 27, 2018 | url-status = dead | archive-url = https://web.archive.org/web/20180928044051/https://spiral.imperial.ac.uk:8443/bitstream/10044/1/54579/2/Kelly_et_al-2017-.pdf | archive-date = September 28, 2018 }}

===Classification===

The term complex carbohydrate was first used in the U.S. Senate Select Committee on Nutrition and Human Needs publication Dietary Goals for the United States (1977) where it was intended to distinguish sugars from other carbohydrates (which were perceived to be nutritionally superior).Joint WHO/FAO expert consultation (1998), Carbohydrates in human nutrition, [http://www.fao.org/docrep/W8079E/w8079e07.htm chapter 1] {{Webarchive|url=https://web.archive.org/web/20070115102707/http://www.fao.org/docrep/w8079e/w8079e07.htm |date=January 15, 2007 }}. {{ISBN|92-5-104114-8}}. However, the report put "fruit, vegetables and whole-grains" in the complex carbohydrate column, despite the fact that these may contain sugars as well as polysaccharides. The standard usage, however, is to classify carbohydrates chemically: simple if they are sugars (monosaccharides and disaccharides) and complex if they are polysaccharides (or oligosaccharides).{{cite web|title=Carbohydrates|url=http://www.hsph.harvard.edu/nutritionsource/carbohydrates/|work=The Nutrition Source|publisher=Harvard School of Public Health|access-date=April 3, 2013|date=September 18, 2012|archive-date=May 7, 2013|archive-url=https://web.archive.org/web/20130507074502/http://www.hsph.harvard.edu/nutritionsource/carbohydrates/|url-status=live}} Carbohydrates are sometimes divided into "available carbohydrates", which are absorbed in the small intestine and "unavailable carbohydrates", which pass to the large intestine, where they are subject to fermentation by the gastrointestinal microbiota.

The glycemic index (GI) and glycemic load concepts characterize the potential for carbohydrates in food to raise blood glucose compared to a reference food (generally pure glucose).{{cite web |title=Glycemic Index and Glycemic Load |url=https://lpi.oregonstate.edu/mic/food-beverages/glycemic-index-glycemic-load |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University |access-date=19 January 2025 |date=2025}} Expressed numerically as GI, carbohydrate-containing foods can be grouped as high-GI (score more than 70), moderate-GI (56-69), or low-GI (less than 55) relative to pure glucose (GI=100). Consumption of carbohydrate-rich, high-GI foods causes an abrupt increase in blood glucose concentration that declines rapidly following the meal, whereas low-GI foods with lower carbohydrate content produces a lower blood glucose concentration that returns gradually after the meal.

Glycemic load is a measure relating the quality of carbohydrates in a food (low- vs. high-carbohydrate content – the GI) by the amount of carbohydrates in a single serving of that food.

{{Main|Low-carbohydrate diet}}

Low-carbohydrate diets may miss the health advantages – such as increased intake of dietary fiber and phytochemicals – afforded by high-quality plant foods such as legumes and pulses, whole grains, fruits, and vegetables.{{cite journal | vauthors = Seidelmann SB, Claggett B, Cheng S, Henglin M, Shah A, Steffen LM, Folsom AR, Rimm EB, Willett WC, Solomon SD | display-authors = 6 | title = Dietary carbohydrate intake and mortality: a prospective cohort study and meta-analysis | journal = The Lancet. Public Health | volume = 3 | issue = 9 | pages = e419–e428 | date = September 2018 | pmid = 30122560 | pmc = 6339822 | doi = 10.1016/s2468-2667(18)30135-x | type = Meta-analysis }}{{cite journal | vauthors = Reynolds A, Mann J, Cummings J, Winter N, Mete E, Te Morenga L | title = Carbohydrate quality and human health: a series of systematic reviews and meta-analyses | journal = Lancet | volume = 393 | issue = 10170 | pages = 434–445 | date = February 2019 | pmid = 30638909 | doi = 10.1016/S0140-6736(18)31809-9 | url = http://discovery.dundee.ac.uk/ws/files/30375889/Final_Lancet_for_John.pdf | access-date = April 24, 2022 | url-status = live | s2cid = 58632705 | doi-access = free | archive-url = https://web.archive.org/web/20210811080032/https://discovery.dundee.ac.uk/ws/files/30375889/Final_Lancet_for_John.pdf | archive-date = August 11, 2021 | type = Review }} A "meta-analysis, of moderate quality," included as adverse effects of the diet halitosis, headache and constipation.{{cite journal | vauthors = Churuangsuk C, Kherouf M, Combet E, Lean M | title = Low-carbohydrate diets for overweight and obesity: a systematic review of the systematic reviews | journal = Obesity Reviews | volume = 19 | issue = 12 | pages = 1700–1718 | date = December 2018 | pmid = 30194696 | doi = 10.1111/obr.12744 | url = http://eprints.gla.ac.uk/168899/1/168899.pdf | access-date = April 24, 2022 | url-status = live | type = Systematic review | s2cid = 52174104 | archive-url = https://web.archive.org/web/20190923071822/http://eprints.gla.ac.uk/168899/1/168899.pdf | archive-date = September 23, 2019 }}{{Better source needed|reason=Quoting source: "Only one meta-analysis, of moderate quality, reported adverse effects of LCDs [...]"|date=August 2022}}

Carbohydrate-restricted diets can be as effective as low-fat diets in helping achieve weight loss over the short term when overall calorie intake is reduced.{{cite journal | vauthors = Schwartz MW, Seeley RJ, Zeltser LM, Drewnowski A, Ravussin E, Redman LM, Leibel RL | title = Obesity Pathogenesis: An Endocrine Society Scientific Statement | journal = Endocrine Reviews | volume = 38 | issue = 4 | pages = 267–296 | date = August 2017 | pmid = 28898979 | pmc = 5546881 | doi = 10.1210/er.2017-00111 }} An Endocrine Society scientific statement said that "when calorie intake is held constant [...] body-fat accumulation does not appear to be affected by even very pronounced changes in the amount of fat vs carbohydrate in the diet." In the long term, low-carbohydrate diets do not appear to confer a "metabolic advantage," and effective weight loss or maintenance depends on the level of calorie restriction, not the ratio of macronutrients in a diet.{{cite book |chapter=Behavioral approaches to the treatment of obesity |vauthors=Butryn ML, Clark VL, Coletta MC |title=Textbook of Obesity | veditors = Akabas SR, Lederman SA, Moore BJ |publisher=John Wiley & Sons|location=New York|year=2012 |quote=Taken together, these findings indicate that calorie intake, not macronutrient composition, determines long-term weight loss maintenance.|isbn=978-0-470-65588-7|page=259}} The reasoning of diet advocates that carbohydrates cause undue fat accumulation by increasing blood insulin levels, but a more balanced diet that restricts refined carbohydrates can also reduce serum glucose and insulin levels and may also suppress lipogenesis and promote fat oxidation.{{cite journal | vauthors = Lopes da Silva MV, de Cassia Goncalves Alfenas R | title = Effect of the glycemic index on lipid oxidation and body composition | journal = Nutrición Hospitalaria | volume = 26 | issue = 1| pages = 48–55 | date = 2011 | doi = 10.3305/nh.2011.26.1.5008 | pmid = 21519729 }} However, as far as energy expenditure itself is concerned, the claim that low-carbohydrate diets have a "metabolic advantage" is not supported by clinical evidence.{{cite journal | vauthors = Hall KD | title = A review of the carbohydrate-insulin model of obesity | journal = European Journal of Clinical Nutrition | volume = 71 | issue = 3 | pages = 323–326 | date = March 2017 | pmid = 28074888 | doi = 10.1038/ejcn.2016.260 | type = Review | s2cid = 54484172 }} Further, it is not clear how low-carbohydrate dieting affects cardiovascular health, although two reviews showed that carbohydrate restriction may improve lipid markers of cardiovascular disease risk.{{cite journal | vauthors = Mansoor N, Vinknes KJ, Veierød MB, Retterstøl K | title = Effects of low-carbohydrate diets v. low-fat diets on body weight and cardiovascular risk factors: a meta-analysis of randomised controlled trials | journal = The British Journal of Nutrition | volume = 115 | issue = 3 | pages = 466–479 | date = February 2016 | pmid = 26768850 | doi = 10.1017/S0007114515004699 | s2cid = 21670516 | doi-access = free }}{{cite journal | vauthors = Gjuladin-Hellon T, Davies IG, Penson P, Amiri Baghbadorani R | title = Effects of carbohydrate-restricted diets on low-density lipoprotein cholesterol levels in overweight and obese adults: a systematic review and meta-analysis | journal = Nutrition Reviews | volume = 77 | issue = 3 | pages = 161–180 | date = March 2019 | pmid = 30544168 | doi = 10.1093/nutrit/nuy049 | url = http://researchonline.ljmu.ac.uk/id/eprint/8898/1/nutr-rev%20corrected%20version%2007072018.pdf | access-date = April 24, 2022 | url-status = live | type = Systematic review | s2cid = 56488132 | doi-access = free | archive-url = https://web.archive.org/web/20200506070047/http://researchonline.ljmu.ac.uk/id/eprint/8898/1/nutr-rev%20corrected%20version%2007072018.pdf | archive-date = May 6, 2020 }}

Carbohydrate-restricted diets are no more effective than a conventional healthy diet in preventing the onset of type 2 diabetes, but for people with type 2 diabetes, they are a viable option for losing weight or helping with glycemic control.{{cite journal | vauthors = Brouns F | title = Overweight and diabetes prevention: is a low-carbohydrate-high-fat diet recommendable? | journal = European Journal of Nutrition | volume = 57 | issue = 4 | pages = 1301–1312 | date = June 2018 | pmid = 29541907 | pmc = 5959976 | doi = 10.1007/s00394-018-1636-y | type = Review }}{{cite journal | vauthors = Meng Y, Bai H, Wang S, Li Z, Wang Q, Chen L | title = Efficacy of low carbohydrate diet for type 2 diabetes mellitus management: A systematic review and meta-analysis of randomized controlled trials | journal = Diabetes Research and Clinical Practice | volume = 131 | pages = 124–131 | date = September 2017 | pmid = 28750216 | doi = 10.1016/j.diabres.2017.07.006 }} There is limited evidence to support routine use of low-carbohydrate dieting in managing type 1 diabetes.{{cite journal | vauthors = Seckold R, Fisher E, de Bock M, King BR, Smart CE | title = The ups and downs of low-carbohydrate diets in the management of Type 1 diabetes: a review of clinical outcomes | journal = Diabetic Medicine | volume = 36 | issue = 3 | pages = 326–334 | date = March 2019 | pmid = 30362180 | doi = 10.1111/dme.13845 | type = Review | s2cid = 53102654 }} The American Diabetes Association recommends that people with diabetes should adopt a generally healthy diet, rather than a diet focused on carbohydrate or other macronutrients.{{cite journal | vauthors = ((American Diabetes Association Professional Practice Committee)) | title = 5. Lifestyle Management: Standards of Medical Care in Diabetes-2019 | journal = Diabetes Care | volume = 42 | issue = Suppl 1 | pages = S46–S60 | date = January 2019 | pmid = 30559231 | doi = 10.2337/dc19-S005 | url = http://care.diabetesjournals.org/content/42/Supplement_1/S46 | access-date = April 24, 2022 | url-status = live | doi-access = free | archive-url = https://web.archive.org/web/20181218145626/http://care.diabetesjournals.org/content/42/Supplement_1/S46 | archive-date = December 18, 2018 }}

An extreme form of low-carbohydrate diet – the ketogenic diet – is established as a medical diet for treating epilepsy. Through celebrity endorsement during the early 21st century, it became a fad diet as a means of weight loss, but with risks of undesirable side effects, such as low energy levels and increased hunger, insomnia, nausea, and gastrointestinal discomfort.{{scientific citation needed|date=May 2023}}{{cite web |publisher=British Dietetic Association |title=Top 5 worst celeb diets to avoid in 2018 |date=7 December 2017 |url=https://www.bda.uk.com/resource/top-5-worst-celeb-diets-to-avoid-in-2018.html |quote=The British Dietetic Association (BDA) today revealed its much-anticipated annual list of celebrity diets to avoid in 2018. The line-up this year includes Raw Vegan, Alkaline, Pioppi and Ketogenic diets as well as Katie Price's Nutritional Supplements. |access-date=1 December 2020 |archive-date=July 31, 2020 |archive-url=https://web.archive.org/web/20200731182316/https://www.bda.uk.com/resource/top-5-worst-celeb-diets-to-avoid-in-2018.html |url-status=live }} The British Dietetic Association named it one of the "top 5 worst celeb diets to avoid in 2018".

File:Glucose 2.jpg

Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).{{Cite news|url=https://www.hsph.harvard.edu/nutritionsource/carbohydrates/carbohydrates-and-blood-sugar/|title=Carbohydrates and Blood Sugar|date=2013-08-05|newspaper=The Nutrition Source|language=en-US|access-date=2017-01-30|via=Harvard T.H. Chan School of Public Health|url-status=live|archive-url=https://web.archive.org/web/20170130010758/https://www.hsph.harvard.edu/nutritionsource/carbohydrates/carbohydrates-and-blood-sugar/|archive-date=2017-01-30}} Unbound glucose is one of the main ingredients of honey. Glucose is extremely abundant and has been isolated from a variety of natural sources across the world, including male cones of the coniferous tree Wollemia nobilis in Rome,{{cite journal | vauthors = Venditti A, Frezza C, Vincenti F, Brodella A, Sciubba F, Montesano C, Franceschin M, Sergi M, Foddai S, Di Cocco ME, Curini R, Delfini M, Bianco A, Serafini M | display-authors = 6 | title = A syn-ent-labdadiene derivative with a rare spiro-β-lactone function from the male cones of Wollemia nobilis | journal = Phytochemistry | volume = 158 | pages = 91–95 | date = February 2019 | pmid = 30481664 | doi = 10.1016/j.phytochem.2018.11.012 | bibcode = 2019PChem.158...91V | s2cid = 53757166 }} the roots of Ilex asprella plants in China,{{cite journal | vauthors = Lei Y, Shi SP, Song YL, Bi D, Tu PF | title = Triterpene saponins from the roots of Ilex asprella | journal = Chemistry & Biodiversity | volume = 11 | issue = 5 | pages = 767–775 | date = May 2014 | pmid = 24827686 | doi = 10.1002/cbdv.201300155 | s2cid = 40353516 }} and straws from rice in California.{{cite book | vauthors = Balan V, Bals B, Chundawat SP, Marshall D, Dale BE | chapter = Lignocellulosic Biomass Pretreatment Using AFEX | title = Biofuels | series = Methods in Molecular Biology | volume = 581 | pages = 61–77 | date = 2009 | pmid = 19768616 | doi = 10.1007/978-1-60761-214-8_5 | publisher = Humana Press | isbn = 978-1-60761-213-1 | bibcode = 2009biof.book...61B | place = Totowa, NJ }}

{{note|2|A}} The carbohydrate value is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".

{{Main|Carbohydrate metabolism}}

Carbohydrate metabolism is the series of biochemical processes responsible for the formation, breakdown and interconversion of carbohydrates in living organisms.

The most important carbohydrate is glucose, a simple sugar (monosaccharide) that is metabolized by nearly all known organisms. Glucose and other carbohydrates are part of a wide variety of metabolic pathways across species: plants synthesize carbohydrates from carbon dioxide and water by photosynthesis storing the absorbed energy internally, often in the form of starch or lipids. Plant components are consumed by animals and fungi, and used as fuel for cellular respiration. Oxidation of one gram of carbohydrate yields approximately 16 kJ (4 kcal) of energy, while the oxidation of one gram of lipids yields about 38 kJ (9 kcal). The human body stores between 300 and 500 g of carbohydrates depending on body weight, with the skeletal muscle contributing to a large portion of the storage.{{Cite web|url=https://onesearch.cuny.edu/primo-explore/fulldisplay?docid=TN_sciversesciencedirect_elsevierS0263-9319(13)00087-2&context=PC&vid=hc&search_scope=everything&tab=default_tab&lang=en_US|title=Surgery Oxford| vauthors = Maughan R |date=June 2013|website=www.onesearch.cuny.edu}}{{Dead link|date=June 2021 |bot=InternetArchiveBot |fix-attempted=yes }} Energy obtained from metabolism (e.g., oxidation of glucose) is usually stored temporarily within cells in the form of ATP.{{cite web | title = Energetics of Cellular Respiration (Glucose Metabolism) | vauthors = Mehta S | work = Biochemistry Notes, Notes | date = 9 October 2013 | url = http://pharmaxchange.info/press/2013/10/energetics-of-cellular-respiration-glucose-metabolism/ | access-date = October 15, 2015 | archive-date = January 25, 2018 | archive-url = https://web.archive.org/web/20180125234509/http://pharmaxchange.info/press/2013/10/energetics-of-cellular-respiration-glucose-metabolism/ | url-status = live }} Organisms capable of anaerobic and aerobic respiration metabolize glucose and oxygen (aerobic) to release energy, with carbon dioxide and water as byproducts.

Catabolism is the metabolic reaction which cells undergo to break down larger molecules, extracting energy. There are two major metabolic pathways of monosaccharide catabolism: glycolysis and the citric acid cycle.

In glycolysis, oligo- and polysaccharides are cleaved first to smaller monosaccharides by enzymes called glycoside hydrolases. The monosaccharide units can then enter into monosaccharide catabolism. A 2 ATP investment is required in the early steps of glycolysis to phosphorylate Glucose to Glucose 6-Phosphate (G6P) and Fructose 6-Phosphate (F6P) to Fructose 1,6-biphosphate (FBP), thereby pushing the reaction forward irreversibly. In some cases, as with humans, not all carbohydrate types are usable as the digestive and metabolic enzymes necessary are not present.

Carbohydrate chemistry is a large and economically important branch of organic chemistry. Some of the main organic reactions that involve carbohydrates are:

• Amadori rearrangement
• Carbohydrate acetalisation
• Carbohydrate digestion
• Cyanohydrin reaction
• Koenigs–Knorr reaction
• Lobry de Bruyn–Van Ekenstein transformation
• Nef reaction
• Wohl degradation
• Tipson-Cohen reaction
• Ferrier rearrangement
• Ferrier II reaction

{{Main|Carbohydrate synthesis}}

Carbohydrate synthesis is a sub-field of organic chemistry concerned specifically with the generation of natural and unnatural carbohydrate structures. This can include the synthesis of monosaccharide residues or structures containing more than one monosaccharide, known as oligosaccharides. Selective formation of glycosidic linkages and selective reactions of hydroxyl groups are very important, and the usage of protecting groups is extensive.

Common reactions for glycosidic bond formation are as follows:

• Chemical glycosylation
• Fischer glycosidation
• Koenigs-Knorr reaction
• Crich beta-mannosylation

While some common protection methods are as below:

• Carbohydrate acetalisation
• Trimethylsilyl
• Benzyl ether
• p-Methoxybenzyl ether

• Bioplastic
• Carbohydrate NMR
• Gluconeogenesis – A process where glucose can be synthesized by non-carbohydrate sources.
• Glycobiology
• Glycogen
• Glycoinformatics
• Glycolipid
• Glycome
• Glycomics
• Glycosyl
• Macromolecule
• Saccharic acid

{{Reflist}}

• {{cite web |url=https://www.ars.usda.gov/ARSUserFiles/80400525/Data/SR/SR28/sr28_doc.pdf |archive-url=https://web.archive.org/web/20161031150436/https://www.ars.usda.gov/ARSUserFiles/80400525/Data/SR/SR28/sr28_doc.pdf |archive-date=2016-10-31 |url-status=live |title=Compolition of foods raw, processed, prepared |publisher=United States Department of Agriculture|date=September 2015 |access-date=October 30, 2016}}

{{Commons category|Carbohydrates}}

{{wikiquote}}

• [https://web.archive.org/web/20130629185521/http://www2.ufp.pt/~pedros/bq/carb_en.htm Carbohydrates, including interactive models and animations] (Requires [https://web.archive.org/web/20060320002451/http://www.mdl.com/products/framework/chime/ MDL Chime])
• [https://web.archive.org/web/20050124032405/http://www.chem.qmw.ac.uk/iupac/2carb/ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature (JCBN): Carbohydrate Nomenclature]
• [http://arquivo.pt/wayback/20160516074319/http://www.cem.msu.edu/~reusch/VirtualText/carbhyd.htm Carbohydrates detailed]
• [http://biochemweb.fenteany.com/carbohydrates.shtml Carbohydrates and Glycosylation – The Virtual Library of Biochemistry, Molecular Biology and Cell Biology]
• [http://www.functionalglycomics.org/ Functional Glycomics Gateway], a collaboration between the Consortium for Functional Glycomics and Nature Publishing Group

{{metabolism}}

{{Food chemistry}}

{{Carbohydrates}}

{{Authority control}}

Category:Nutrition