WordNet

a simple sugar found in honey and in many ripe fruits (同)fruit_sugar, levulose, laevulose
cause to bear fruit
the ripened reproductive body of a seed plant
the consequence of some effort or action; "he lived long enough to see the fruit of his policies"
bear fruit; "the trees fruited early this year"
sweeten with sugar; "sugar your tea" (同)saccharify
a white crystalline carbohydrate used as a sweetener and preservative (同)refined sugar
with sweetening added (同)sweetened, sweet, sweet-flavored
capable of bearing fruit

PrepTutorEJDIC

〈U〉果糖
〈U〉〈C〉『果物』,(植物の)実,果実 / 《複数形で》『農作物』(果物・穀物・野菜など) / 〈U〉〈C〉《しばしば複数形で》『成果』,結果 / 実を結ぶ
〈U〉砂糖 / 〈C〉(1個・さじ1杯の)砂糖 / 〈U〉庶糖 / 《話》(恋人に対して呼び掛けて)ねえ / …‘に'砂糖を混ぜる(かける);…‘に'砂糖を加えて甘くする

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/05 01:48:22」(JST)

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Fructose, or fruit sugar, is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into the bloodstream during digestion. Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847.^[4]^[5] The name "fructose" was coined in 1857 by the English chemist William Miller.^[6] Pure, dry fructose is a very sweet, white, odorless, crystalline solid and is the most water-soluble of all the sugars.^[7] Fructose is found in honey, tree and vine fruits, flowers, berries, and most root vegetables.

Commercially, fructose is frequently derived from sugar cane, sugar beets, and corn. Crystalline fructose is the monosaccharide, dried, ground, and of high purity. High fructose corn syrup (HFCS) is a mixture of glucose and fructose as monosaccharides. Sucrose is a compound with one molecule of glucose covalently linked to one molecule of fructose. All forms of fructose, including fruits and juices, are commonly added to foods and drinks for palatability and taste enhancement, and for browning of some foods, such as baked goods.

About 240,000 tonnes of crystalline fructose are produced annually.^[8]

There is research indicating that excessive fructose consumption is a cause of insulin resistance, obesity,^[9] elevated LDL cholesterol and triglycerides, leading to metabolic syndrome,^[10]^[11]^[12] type 2 diabetes and cardiovascular disease.^[13] However, the European Food Safety Authority stated that fructose is preferred over sucrose and glucose in sugar-sweetened foods and beverages because of its lower effect on postprandial blood sugar levels.^[14] Further, the UK's Scientific Advisory Committee on Nutrition in 2015 disputed the claims of fructose causing metabolic disorders, stating that "there is insufficient evidence to demonstrate that fructose intake ... leads to adverse health outcomes independent of any effects related to its presence as a component of total and free sugars."^[15]

1 Chemical properties
- 1.1 Reactions
  - 1.1.1 Fructose and fermentation
  - 1.1.2 Fructose and Maillard reaction
  - 1.1.3 Dehydration
2 Physical and functional properties
- 2.1 Sweetness of fructose
- 2.2 Fructose solubility and crystallization
- 2.3 Fructose hygroscopicity and humectancy
- 2.4 Freezing point
- 2.5 Fructose and starch functionality in food systems
3 Food sources
- 3.1 Carbohydrate content of commercial sweeteners (percent on dry basis)
4 Fructose digestion and absorption in humans
- 4.1 Capacity and rate of absorption
- 4.2 Malabsorption
5 Fructose metabolism
- 5.1 Fructolysis
- 5.2 Metabolism of fructose to DHAP and glyceraldehyde
- 5.3 Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate
- 5.4 Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate
- 5.5 Fructose synthesis
6 Potential health effects
- 6.1 Digestion
- 6.2 Weight gain
- 6.3 Cardiometabolic diseases
- 6.4 Compared with sucrose
- 6.5 Liver function
- 6.6 Gout
- 6.7 Glycemic index
- 6.8 Appetite control
7 See also
8 References
9 External links

Chemical properties

Figure 1: Relationship between the acyclic and the cyclic (hemiketal) isomers of fructose

D- and L-isomers of fructose (open-chain form)

Fructose is a 6-carbon polyhydroxyketone. Crystalline fructose adopts a cyclic six-membered structure owing to the stability of its hemiketal and internal hydrogen-bonding. This form is formally called D-fructopyranose. In solution, fructose exists as an equilibrium mixture of 70% fructopyranose and about 22% fructofuranose, as well as small amounts of three other forms, including the acyclic structure.^[16]

Reactions

Fructose and fermentation

Fructose may be anaerobically fermented by yeast or bacteria.^[17] Yeast enzymes convert sugar (glucose, or fructose) to ethanol and carbon dioxide. The carbon dioxide released during fermentation will remain dissolved in water, where it will reach equilibrium with carbonic acid, unless the fermentation chamber is left open to the air. The dissolved carbon dioxide and carbonic acid produce the carbonation in bottled fermented beverages.^[18]

Fructose and Maillard reaction

Fructose undergoes the Maillard reaction, non-enzymatic browning, with amino acids. Because fructose exists to a greater extent in the open-chain form than does glucose, the initial stages of the Maillard reaction occur more rapidly than with glucose. Therefore, fructose has potential to contribute to changes in food palatability, as well as other nutritional effects, such as excessive browning, volume and tenderness reduction during cake preparation, and formation of mutagenic compounds.^[19]

Dehydration

Fructose readily dehydrates to give hydroxymethylfurfural ("HMF"). This process, in the future, may become part of a low-cost, carbon-neutral system to produce replacements for petrol and diesel from plants.^[20]

Physical and functional properties

Sweetness of fructose

The primary reason that fructose is used commercially in foods and beverages, besides its low cost, is its high relative sweetness. It is the sweetest of all naturally occurring carbohydrates. In general, fructose is regarded as being 1.73 times as sweet as sucrose.^[21]^[22] However, it is the 6-membered ring form of fructose that is sweeter; the 5-membered ring form tastes about the same as usual table sugar. Warming fructose leads to formation of the 5-membered ring form.^[23]

Figure 2: Relative sweetness of sugars and sweeteners

The sweetness of fructose is perceived earlier than that of sucrose or glucose, and the taste sensation reaches a peak (higher than that of sucrose) and diminishes more quickly than that of sucrose. Fructose can also enhance other flavors in the system.^[21]

Fructose exhibits a sweetness synergy effect when used in combination with other sweeteners. The relative sweetness of fructose blended with sucrose, aspartame, or saccharin is perceived to be greater than the sweetness calculated from individual components.^[24]

Fructose solubility and crystallization

Fructose has higher solubility than other sugars as well as other sugar alcohols. Fructose is, therefore, difficult to crystallize from an aqueous solution.^[21] Sugar mixes containing fructose, such as candies, are softer than those containing other sugars because of the greater solubility of fructose.^[25]

Fructose hygroscopicity and humectancy

Fructose is quicker to absorb moisture and slower to release it to the environment than sucrose, glucose, or other nutritive sweeteners.^[24] Fructose is an excellent humectant and retains moisture for a long period of time even at low relative humidity (RH). Therefore, fructose can contribute a more palatable texture, and longer shelf life to the food products in which it is used.^[21]

Freezing point

Fructose has a greater effect on freezing point depression than disaccharides or oligosaccharides, which may protect the integrity of cell walls of fruit by reducing ice crystal formation. However, this characteristic may be undesirable in soft-serve or hard-frozen dairy desserts.^[21]

Fructose and starch functionality in food systems

Fructose increases starch viscosity more rapidly and achieves a higher final viscosity than sucrose because fructose lowers the temperature required during gelatinizing of starch, causing a greater final viscosity.^[26]

Although some artificial sweeteners are not suitable for home-baking, many traditional recipes use fructose.^[27]

Food sources

Crystalline fructose

Natural sources of fructose include fruits, vegetables (including sugar cane), and honey.^[28] Fructose is often further concentrated from these sources. The highest dietary sources of fructose, besides pure crystalline fructose, are foods containing table sugar (sucrose), high-fructose corn syrup, agave nectar, honey, molasses, maple syrup, fruit and fruit juices, as these have the highest percentages of fructose (including fructose in sucrose) per serving compared to other common foods and ingredients. Fructose exists in foods either as a free monosaccharide or bound to glucose as sucrose, a disaccharide. Fructose, glucose, and sucrose may all be present in a food; however, different foods will have varying levels of each of these three sugars.

The sugar contents of common fruits and vegetables are presented in Table 1. In general, in foods that contain free fructose, the ratio of fructose to glucose is approximately 1:1; that is, foods with fructose usually contain about an equal amount of free glucose. A value that is above 1 indicates a higher proportion of fructose to glucose, and below 1 a lower proportion. Some fruits have larger proportions of fructose to glucose compared to others. For example, apples and pears contain more than twice as much free fructose as glucose, while for apricots the proportion is less than half as much fructose as glucose.

Apple and pear juices are of particular interest to pediatricians because the high concentrations of free fructose in these juices can cause diarrhea in children. The cells (enterocytes) that line children's small intestines have less affinity for fructose absorption than for glucose and sucrose.^[29] Unabsorbed fructose creates higher osmolarity in the small intestine, which draws water into the gastrointestinal tract, resulting in osmotic diarrhea. This phenomenon is discussed in greater detail in the Health Effects section.

Table 1 also shows the amount of sucrose found in common fruits and vegetables. Sugarcane and sugar beet have a high concentration of sucrose, and are used for commercial preparation of pure sucrose. Extracted cane or beet juice is clarified, removing impurities; and concentrated by removing excess water. The end-product is 99.9%-pure sucrose. Sucrose-containing sugars include common table white granulated sugar and powdered sugar, as well as brown sugar.^[30]

Table 1. Sugar content of selected common plant foods (g/100g)^[31]
Food Item	Total Carbohydrate^A including "dietary fiber"	Total Sugars	Free Fructose	Free Glucose	Sucrose	Fructose/ Glucose Ratio	Sucrose as a % of Total Sugars
Fruits
Apple	13.8	10.4	5.9	2.4	2.1	2.0	19.9
Apricot	11.1	9.2	0.9	2.4	5.9	0.7	63.5
Banana	22.8	12.2	4.9	5.0	2.4	1.0	20.0
Fig, dried	63.9	47.9	22.9	24.8	0.9	0.93	0.15
Grapes	18.1	15.5	8.1	7.2	0.2	1.1	1
Navel orange	12.5	8.5	2.25	2.0	4.3	1.1	50.4
Peach	9.5	8.4	1.5	2.0	4.8	0.9	56.7
Pear	15.5	9.8	6.2	2.8	0.8	2.1	8.0
Pineapple	13.1	9.9	2.1	1.7	6.0	1.1	60.8
Plum	11.4	9.9	3.1	5.1	1.6	0.66	16.2
Vegetables
Beet, Red	9.6	6.8	0.1	0.1	6.5	1.0	96.2
Carrot	9.6	4.7	0.6	0.6	3.6	1.0	77
Red Pepper, Sweet	6.0	4.2	2.3	1.9	0.0	1.2	0.0
Onion, Sweet	7.6	5.0	2.0	2.3	0.7	0.9	14.3
Sweet Potato	20.1	4.2	0.7	1.0	2.5	0.9	60.3
Yam	27.9	0.5	tr	tr	tr	na	tr
Sugar Cane		13 – 18	0.2 – 1.0	0.2 – 1.0	11 – 16	1.0	high
Sugar Beet		17 – 18	0.1 – 0.5	0.1 – 0.5	16 – 17	1.0	high
Grains
Corn, Sweet	19.0	6.2	1.9	3.4	0.9	0.61	15.0

^A The carbohydrate figure is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".

All data with a unit of g (gram) are based on 100 g of a food item. The fructose/glucose ratio is calculated by dividing the sum of free fructose plus half sucrose by the sum of free glucose plus half sucrose.

Fructose is also found in the synthetically manufactured sweetener, high-fructose corn syrup (HFCS). Hydrolyzed corn starch is used as the raw material for production of HFCS. Through the enzymatic treatment, glucose molecules are converted into fructose.^[30] There are three types of HFCS, each with a different proportion of fructose: HFCS-42, HFCS-55, and HFCS-90. The number for each HFCS corresponds to the percentage of synthesized fructose present in the syrup. HFCS-90 has the highest concentration of fructose, and typically, is used to manufacture HFCS-55; HFCS-55 is used as sweetener in soft drinks, whereas HFCS-42 is used in many processed foods and baked goods.

Carbohydrate content of commercial sweeteners (percent on dry basis)

Sugar	Fructose	Glucose	Sucrose (Fructose+Glucose)	Other sugars
Granulated sugar	0	0	100	0
Caramel	1	1	97	1
HFCS-42	42	53	0	5
HFCS-55	55	41	0	4
HFCS-90	90	5	0	5
Honey	50	44	1	5
Maple syrup	1	4	95	0
Molasses	23	21	53	3
Tapioca Syrup	55	45	0	0
Corn syrup	0	35	0	0

Data obtained from Kretchmer, N. & Hollenbeck, CB (1991). Sugars and Sweeteners, Boca Raton, FL: CRC Press, Inc.^[30] for HFCS, and USDA for fruits and vegetables and the other refined sugars.^[31]

Cane and beet sugars have been used as the major sweetener in food manufacturing for centuries. However, with the development of HFCS, a significant shift occurred in the type of sweetener consumption in certain countries, particularly the United States.^[32] As seen in Figure 3, this change happened in the 1970s. Contrary to the popular belief, however, with the increase of HFCS consumption, the total fructose intake relative to the total glucose intake has not dramatically changed. Granulated sugar is 99.9%-pure sucrose, which means that it has equal ratio of fructose to glucose. The most commonly used forms of HFCS, HFCS-42, and HFCS-55 have a roughly equal ratio of fructose to glucose, with minor differences. HFCS has simply replaced sucrose as a sweetener. Therefore, despite the changes in the sweetener consumption, the ratio of glucose to fructose intake has remained relatively constant.^[33]

Figure 3: Adjusted consumption of refined sugar per capita in the US

Fructose digestion and absorption in humans

Figure 4: Hydrolysis of sucrose to glucose and fructose by sucrase

Figure 5: Intestinal sugar transport proteins

Fructose exists in foods either as a monosaccharide (free fructose) or as a unit of a disaccharide (sucrose). Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. As sucrose comes into contact with the membrane of the small intestine, the enzyme sucrase catalyzes the cleavage of sucrose to yield one glucose unit and one fructose unit, which are then each absorbed. After absorption, it enters the hepatic portal vein and is directed toward the liver.

The mechanism of fructose absorption in the small intestine is not completely understood. Some evidence suggests active transport, because fructose uptake has been shown to occur against a concentration gradient.^[34] However, the majority of research supports the claim that fructose absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 transport proteins. Since the concentration of fructose is higher in the lumen, fructose is able to flow down a concentration gradient into the enterocytes, assisted by transport proteins. Fructose may be transported out of the enterocyte across the basolateral membrane by either GLUT2 or GLUT5, although the GLUT2 transporter has a greater capacity for transporting fructose, and, therefore, the majority of fructose is transported out of the enterocyte through GLUT2.

Capacity and rate of absorption

The absorption capacity for fructose in monosaccharide form ranges from less than 5 g to 50 g (per individual serving) and adapts with changes in dietary fructose intake.^[35] Studies show the greatest absorption rate occurs when glucose and fructose are administered in equal quantities.^[35] When fructose is ingested as part of the disaccharide sucrose, absorption capacity is much higher because fructose exists in a 1:1 ratio with glucose. It appears that the GLUT5 transfer rate may be saturated at low levels, and absorption is increased through joint absorption with glucose.^[36] One proposed mechanism for this phenomenon is a glucose-dependent cotransport of fructose. In addition, fructose transfer activity increases with dietary fructose intake. The presence of fructose in the lumen causes increased mRNA transcription of GLUT5, leading to increased transport proteins. High-fructose diets (>2.4 g/kg body wt) increase transport proteins within three days of intake.^[37]

Malabsorption

Several studies have measured the intestinal absorption of fructose using the hydrogen breath test.^[38]^[39]^[40]^[41] These studies indicate that fructose is not completely absorbed in the small intestine. When fructose is not absorbed in the small intestine, it is transported into the large intestine, where it is fermented by the colonic flora. Hydrogen is produced during the fermentation process and dissolves into the blood of the portal vein. This hydrogen is transported to the lungs, where it is exchanged across the lungs and is measurable by the hydrogen breath test. The colonic flora also produces carbon dioxide, short-chain fatty acids, organic acids, and trace gases in the presence of unabsorbed fructose.^[42] The presence of gases and organic acids in the large intestine causes gastrointestinal symptoms such as bloating, diarrhea, flatulence, and gastrointestial pain^[38] Exercise immediately after consumption can exacerbate these symptoms by decreasing transit time in the small intestine, resulting in a greater amount of fructose emptied into the large intestine.^[43]

Fructose metabolism

All three dietary monosaccharides are transported into the liver by the GLUT2 transporter.^[44] Fructose and galactose are phosphorylated in the liver by fructokinase (K_m= 0.5 mM) and galactokinase (K_m = 0.8 mM). By contrast, glucose tends to pass through the liver (K_m of hepatic glucokinase = 10 mM) and can be metabolised anywhere in the body. Uptake of fructose by the liver is not regulated by insulin. However, insulin is capable of increasing the abundance and functional activity of GLUT5 in skeletal muscle cells.^[45]

Fructolysis

The initial catabolism of fructose is sometimes referred to as fructolysis, in analogy with glycolysis, the catabolism of glucose. In fructolysis, the enzyme fructokinase initially produces fructose 1-phosphate, which is split by aldolase B to produce the trioses dihydroxyacetone phosphate (DHAP) and glyceraldehyde [2]. Unlike glycolysis, in fructolysis the triose glyceraldehyde lacks a phosphate group. A third enzyme, triokinase, is therefore required to phosphorylate glyceraldehyde, producing glyceraldehyde 3-phosphate. The resulting trioses are identical to those obtained in glycolysis and can enter the gluconeogenic pathway for glucose or glycogen synthesis, or be further catabolized through the lower glycolytic pathway to pyruvate.

Metabolism of fructose to DHAP and glyceraldehyde

The first step in the metabolism of fructose is the phosphorylation of fructose to fructose 1-phosphate by fructokinase, thus trapping fructose for metabolism in the liver. Fructose 1-phosphate then undergoes hydrolysis by aldolase B to form DHAP and glyceraldehydes; DHAP can either be isomerized to glyceraldehyde 3-phosphate by triosephosphate isomerase or undergo reduction to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The glyceraldehyde produced may also be converted to glyceraldehyde 3-phosphate by glyceraldehyde kinase or further converted to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The metabolism of fructose at this point yields intermediates in the gluconeogenic pathway leading to glycogen synthesis as well as fatty acid and triglyceride synthesis.

Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate

The resultant glyceraldehyde formed by aldolase B then undergoes phosphorylation to glyceraldehyde 3-phosphate. Increased concentrations of DHAP and glyceraldehyde 3-phosphate in the liver drive the gluconeogenic pathway toward glucose and subsequent glycogen synthesis.^[46] It appears that fructose is a better substrate for glycogen synthesis than glucose and that glycogen replenishment takes precedence over triglyceride formation.^{[citation needed]} Once liver glycogen is replenished, the intermediates of fructose metabolism are primarily directed toward triglyceride synthesis.^{[citation needed]}

Figure 6: Metabolic conversion of fructose to glycogen in the liver

Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate

Carbons from dietary fructose are found in both the free fatty acid and glycerol moieties of plasma triglycerides. High fructose consumption can lead to excess pyruvate production, causing a buildup of Krebs cycle intermediates.^[47] Accumulated citrate can be transported from the mitochondria into the cytosol of hepatocytes, converted to acetyl CoA by citrate lyase and directed toward fatty acid synthesis.^[47]^[48] In addition, DHAP can be converted to glycerol 3-phosphate, providing the glycerol backbone for the triglyceride molecule.^[48] Triglycerides are incorporated into very-low-density lipoproteins (VLDL), which are released from the liver destined toward peripheral tissues for storage in both fat and muscle cells.

Figure 7: Metabolic conversion of fructose to triglyceride in the liver

Fructose synthesis

Humans are capable of synthesizing fructose from glucose via the polyol pathway. This pathway is used by the seminal vesicles to secrete fructose into semen where it is a major source of energy for sperm.^{[citation needed]}

Potential health effects

Digestion

Fructose absorption occurs in the small intestine via the GLUT-5^[49] (fructose only) transporter, and the GLUT2 transporter, for which it competes with glucose and galactose. Over-consumption of fructose, inhibition of GLUT2 by other phytochemicals, such as flavonoids,^[50] or other issues, may result in delivery of unabsorbed fructose into the large intestine, which will cause more water to be drawn into the large intestine through the process of osmosis causing diarrhea.^[51] In addition, the excessive fructose becomes a source of nutrients for the gut flora resulting in a higher production of short chain fatty acids, hydrogen, carbon dioxide and other gases due to fermentation.^[52] This increase of gas causes gastrointestinal side effects that mimic irritable bowel syndrome.^[52]

Weight gain

In a meta-analysis of clinical trials with controlled feeding — where test subjects were fed a fixed amount of energy rather than being allowed to choose the amount they ate — fructose was not an independent factor for weight gain; however, fructose consumption was associated with weight gain when the fructose provided excess calories.^[53]

Cardiometabolic diseases

Excess fructose consumption has been hypothesized to be a cause of insulin resistance, obesity,^[9]^[54] elevated LDL cholesterol and triglycerides, leading to metabolic syndrome.^[10]^[54] In preliminary research, fructose consumption was correlated with obesity.^[11]^[55] Fructose encourages visceral adipose tissue deposition in humans.^[12]^[56]

Studies indicate that there may be an increased risk of cardiovascular disease from a high intake of fructose.^[57] Studies have associated high fructose consumption with increased incidence of hypertension, both acutely ^[58] and in the long term in subjects without a history of hypertension.^[59] The mechanistic link for this is thought to be the increased production of uric acid,^[60] a known predictor for hypertension.^[61] The elevation in uric acid is due to unregulated phosphorylation leading to depletion of ATP and subsequent ADP degradation to uric acid.^[62]

Another study in humans concluded that fructose and sucrose are metabolized similarly,^[63] whereas a different analysis "produced significantly higher fasting plasma triglyceride values than did the glucose diet in men" and "...if plasma triacylglycerols are a risk factor for cardiovascular disease, then diets high in fructose may be undesirable".^[64] A study in 2015 later confirmed this by showing that consuming beverages with high levels of high fructose corn syrup caused heightened levels of LDL cholesterol, non-HDL cholesterol, apolipoprotein B, all of which are lipid/lipoproteins risk factors for cardiovascular disease.^[65]

In contrast to the above claims of fructose contributing to cardiometabolic diseases, an expert panel of the European Food Safety Authority concluded that fructose be preferred in food and beverage manufacturing to replace sucrose and glucose due to the lower effect of fructose on blood glucose levels following a meal.^[14]

Compared with sucrose

Fructose is often recommended for diabetics because it does not trigger the production of insulin by pancreatic β cells, probably because β cells have low levels of GLUT5,^[66]^[67]^[68] although the net effect for both diabetics^[69] and non-diabetics is debated. Fructose has a low glycemic index of 19 ± 2, compared with 100 for glucose and 68 ± 5 for sucrose.^[70] Fructose is also 73% sweeter than sucrose at room temperature, so diabetics can use less of it. Studies show that fructose consumed before a meal may even lessen the glycemic response of the meal.^[71] Fructose-sweetened food and beverage products cause less of a rise in blood glucose levels than do those manufactured with sucrose or glucose.^[14]

Liver function

Excessive fructose consumption may contribute to the development of non-alcoholic fatty liver disease.^[72]^[73]

Gout

A 2008 study found a risk of incident gout associated with high consumption of fructose or fructose-rich foods.^[74]

Glycemic index

Fructose has the lowest glycemic index (GI = 19) of all the natural sugars. In comparison, ordinary table sugar (sucrose, which is half fructose) has a GI of 65 and honey (usually about 50% fructose content) has a GI of 55.

Appetite control

Compared with consumption of high glucose beverages, drinking high-fructose beverages with meals results in lower circulating insulin and leptin levels, and higher ghrelin levels after the meal.^[75] Since leptin and insulin decrease appetite and ghrelin increases appetite, some researchers suspect that eating large amounts of fructose increases the likelihood of weight gain.^[76]

References

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^ Levulose comes from the Latin word laevus, levo, "left side", levulose is the old word for the most occurring isomer of fructose. D-fructose rotate plane-polarised light to the left, hence the name.[1].
^ Michael Chambers. "ChemIDplus – 57-48-7 – BJHIKXHVCXFQLS-UYFOZJQFSA-N – Fructose [USP:JAN] – Similar structures search, synonyms, formulas, resource links, and other chemical information.". Chem.sis.nlm.nih.gov. Retrieved 10 December 2014.
^ Dubrunfaut (1847) "Sur une propriété analytique des fermentations alcoolique et lactique, et sur leur application à l'étude des sucres" (On an analytic property of alcoholic and lactic fermentations, and on their application to the study of sugars), Annales de Chimie et de Physique, 21 : 169–178. On page 174, Dubrunfaut relates the discovery and properties of fructose.
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UpToDate Contents

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1. 2型糖尿病の危険因子risk factors for type 2 diabetes mellitus [show details]
…Consumption of red meat, processed meat, and sugar sweetened beverages is associated with an increased risk of diabetes, whereas consumption of a diet high in fruits, vegetables, nuts, whole grains, and olive …
2. 幼児、未就学児、就学児に推奨される食事dietary recommendations for toddlers preschool and school age children [show details]
…include fresh fruit, cheese, whole-grain crackers or bread products, milk, raw vegetables, 100 percent fruit juices, sandwiches, peanut butter, and yogurt . Added sugars – Added sugars include sugars and syrups …
3. 小児や青年の肥満の定義、疫学、病因definition epidemiology and etiology of obesity in children and adolescents [show details]
…nutrient-dense diet, emphasizing vegetables, fruits, and whole grains; with quality protein sources and low-fat or nonfat milk and dairy; limited intake of sugar-sweetened beverages; modest fat content; and …
4. 乳児期における固形食の導入およびビタミン並びにミネラルの補給introducing solid foods and vitamin and mineral supplementation during infancy [show details]
… The use of fruit juice in the management of dehydration is discussed separately. Sugar-sweetened beverages – Consumption of sugar-sweetened beverages (eg, soda, tea, coffee, fruit-flavored drinks) …
5. 青年の食習慣adolescent eating habits [show details]
… particular, sugar-sweetened beverages often have a negative impact on diet quality and also contribute to weight gain . In a national survey in the United States, sugar-sweetened beverages or fruit juice comprised …

English Journal

Fructose malabsorption.

Ebert K1,2,3, Witt H4,5,6.
Molecular and cellular pediatrics.Mol Cell Pediatr.2016 Dec;3(1):10. doi: 10.1186/s40348-016-0035-9. Epub 2016 Feb 16.
Incomplete intestinal absorption of fructose might lead to abdominal complaints such as pain, flatulence and diarrhoea. Whether defect fructose transporters such as GLUT5 or GLUT2 are involved in the pathogenesis of fructose malabsorption is a matter of debate. The hydrogen production by colonic bac
PMID 26883354

Determination of sugars, organic acids, aroma components, and carotenoids in grapefruit pulps.

Zheng H1, Zhang Q1, Quan J2, Zheng Q1, Xi W3.
Food chemistry.Food Chem.2016 Aug 15;205:112-21. doi: 10.1016/j.foodchem.2016.03.007. Epub 2016 Mar 3.
The composition and content of sugars, organic acids, volatiles and carotenoids, in the pulps of six grapefruit cultivars, were examined by HPLC and GC-MS. The results showed that sucrose was the dominant sugar in grapefruit, making up 40.08-59.68% of the total sugars, and the ratio of fructose to g
PMID 27006221

Chemical composition and antioxidant capacity of different anatomical parts of pear (Pyrus communis L.).

Kolniak-Ostek J1.
Food chemistry.Food Chem.2016 Jul 15;203:491-7. doi: 10.1016/j.foodchem.2016.02.103. Epub 2016 Feb 16.
Sugar, organic acid, triterpenoid and phenolic composition as well as antioxidant capacity of different anatomical parts of pear were studied. Fruits and leaves of 'Radana' pear (Pyrus communis L.) were used. The results showed great quantitative differences in the composition of the pear pulp, peel
PMID 26948642

Japanese Journal

天然型アブシジン酸の土壌散布がウンシュウミカンの果実肥大と品質に及ぼす影響

河合義隆,岡本真依,白石亮,藤澤弘幸
東京農業大学農学集報 59(2), 114-120, 2014-09-19
植物ホルモンの天然型アブシジン酸(S-ABA)を土壌散布処理し,ウンシュウミカンの果実の肥大と品質に及ぼす影響を2009年と2010年に調べた。両年ともS-ABA土壌散布(0,0.1,1,10ppm)を果実肥大期の7月と9月に2回行ったところ,果実の肥大が促進され,S-ABA区で果重,果実の横径,縦径が大きくなった。一方,果皮色は,S-ABA処理区で着色が両年とも抑制された。糖含量はS-ABA処理 …
NAID 110009838666

Identification of QTLs for fruit quality traits in Japanese apples : QTLs for early ripening are tightly related to preharvest fruit drop

Kunihisa Miyuki,Moriya Shigeki,Abe Kazuyuki [他]
Breeding science 64(3), 240-251, 2014-09
NAID 40020194260

Effects of the Rare Sugars D-psicose and D-tagatose on the Sugar Content and Incidence of Blossom End Rot in Tomato Grown Hydroponically with Salinity Treatment

YAMADA Yoshihiro,KAKIBUCHI Kazumasa,KOZUKI Ayako [他]
Environment control in biology 52(3), 155-160, 2014-09
NAID 40020189424

「フルクトース」

D-Fructose
D-Fructofuranose	D-Fructose (open-chain form)
	; Haworth projection of β-D-Fructofuranose
	; Ball-and-stick model of D-fructose
Names
	IUPAC name (3R,4S)-1,3,4,5,6-Pentahydroxy-2-hexanone
	Other names Fruit sugar, levulose, D-fructofuranose, D-fructose, D-arabino-hexulose
Identifiers
CAS Number	57-48-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28645
ChEMBL	ChEMBL604608
ChemSpider	388775
ECHA InfoCard	100.000.303
EC Number	200-333-3
KEGG	C02336
PubChem	5984
UNII	6YSS42VSEV
	InChI InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1 Key: RFSUNEUAIZKAJO-ARQDHWQXSA-N ;
	SMILES O[C@H]1[C@H](O)[C@H](O[C@]1(O)CO)CO ;
Properties
Chemical formula	C6H12O6
Molar mass	180.16 g·mol−1
Density	1.694 g/cm3
Melting point	103 °C (217 °F; 376 K)
Magnetic susceptibility (χ)	-102.60·10−6 cm3/mol
Pharmacology
ATC code	V06DC02 (WHO)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	15000 mg/kg (intravenous, rabbit)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: fructose, Fru
同: 果糖, fruit sugar、レブロース levulose
商: 果糖注、フルクトン。(果糖、グリセリン)グリセレブ、グリセオール、グリセノン、グリセリンF、ヒシセオール、グリポーゼ、グリマッケン。(アミノ酸輸液製剤)アミノトリパ1号輸液、トリパレン1号、トリフリード輸液、フルクトラクト
関: 単糖、糖

グルコース + フルクトース → スクロース

薬効

5%, 20%フルクトースとして

20％フルクトン注

1. エネルギー補給：果糖はブドウ糖に比べてグリコーゲン生成能が大で、容易に乳酸に分解されるため、速やかにエネルギー源となり、糖尿病状態時や肝障害時でも利用される。
2. インスリン非依存性：果糖は主として肝に存在するfructokinase(ketohexokinase)により代謝され、インスリンの影響を受けず、糖尿病状態時にも使用できる。
3. 蛋白節約作用：果糖は体内窒素平衡に関与し、ブドウ糖に比べて強い蛋白節約作用があり、糖尿病状態時でもその作用を示す。
4. 解毒作用：果糖はアルコール及び種々有毒物質の解毒を促進する

グリセリン、フルクトースの混合輸液として

グリポーゼ

脳圧降下作用のあるグリセリン（グリセロール）に，溶血防止作用のある果糖（フルクトース）が配合されており、脳圧降下作用及び眼圧降下作用がある。

アミノ酸輸液との配合輸液として

アミノトリパ

1. 糖質とアミノ酸の配合比率：本剤を構成する糖質・電解質液とアミノ酸液との配合比率を検討するため、一定の非蛋白熱量下にアミノ酸配合量を変えた液を用いて、絶食ラットに7日間の高カロリー輸液を施行した。その結果、蛋白栄養指標（窒素出納や血漿アルブミン濃度等）を良好に維持するための非蛋白熱量/窒素（NPC/N）は約150前後であることが確認された。
2. 栄養学的効果：本剤の栄養学的効果を市販製剤の混合液と比較するため、開腹術施行ラットに7日間の高カロリー輸液を施行した。その結果、本剤は窒素出納や肝グリコーゲン量等において、良好な栄養効果が認められた。

「fructose」

　　[★] フルクトース、果糖、fruit sugar、levulose 　　

「fruit」

　　[★]

n.

果実
成果、結果

関: berry、seed setting、set a seed

「sugar」

　　[★]

糖、糖質

関: carbohydrate、glucide、glyco

「sugars」

　　[★] 糖、糖質、carbohydrates

[1] "Fructose – Definition and More from the Free Merriam-Webster Dictionary". Mw4.m-w.com. Retrieved 10 December 2014.

[2] Levulose comes from the Latin word laevus, levo, "left side", levulose is the old word for the most occurring isomer of fructose. D-fructose rotate plane-polarised light to the left, hence the name.[1].

[3] Michael Chambers. "ChemIDplus – 57-48-7 – BJHIKXHVCXFQLS-UYFOZJQFSA-N – Fructose [USP:JAN] – Similar structures search, synonyms, formulas, resource links, and other chemical information.". Chem.sis.nlm.nih.gov. Retrieved 10 December 2014.

[4] Dubrunfaut (1847) "Sur une propriété analytique des fermentations alcoolique et lactique, et sur leur application à l'étude des sucres" (On an analytic property of alcoholic and lactic fermentations, and on their application to the study of sugars), Annales de Chimie et de Physique, 21 : 169–178. On page 174, Dubrunfaut relates the discovery and properties of fructose.

[5] Fruton, J.S. Molecules of Life 1972, Wiley-Interscience

[6] William Allen Miller, Elements of Chemistry: Theoretical and Practical, Part III. Organic Chemistry (London, England: John W. Parker and son, 1857), pages 52 and 57.

[Hyvonen.26Koivistoinen1982-7] Hyvonen, L. & Koivistoinen, P (1982). "Fructose in Food Systems". In Birch, G.G. & Parker, K.J. Nutritive Sweeteners. London & New Jersey: Applied Science Publishers. pp. 133–144. ISBN 0-85334-997-5.

[8] Wolfgang Wach "Fructose" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim.doi:10.1002/14356007.a12_047.pub2

[pmid12399260-9] Elliott SS, Keim NL, Stern JS, Teff K, Havel PJ (2002). "Fructose, weight gain, and the insulin resistance syndrome". Am. J. Clin. Nutr. 76 (5): 911–22. PMID 12399260.

[PMC552336-10] Basciano H, Federico L, Adeli K (2005). "Fructose, insulin resistance, and metabolic dyslipidemia". Nutrition & Metabolism. 2 (5): 5. doi:10.1186/1743-7075-2-5. PMC 552336. PMID 15723702.

[pmid16166564-11] Isganaitis E; Lustig RH (2005). "Fast food, central nervous system insulin resistance, and obesity". Arterioscler. Thromb. Vasc. Biol. 25 (12): 2451–62. doi:10.1161/01.ATV.0000186208.06964.91. PMID 16166564.

[MalikHu2015-12] Malik, Vasanti S.; Hu, Frank B. (2015). "Fructose and Cardiometabolic Health". Journal of the American College of Cardiology. 66 (14): 1615–1624. doi:10.1016/j.jacc.2015.08.025. ISSN 0735-1097. PMID 26429086.

[13] Rippe, James M.; Angelopoulos, Theodore J. (2015-07-01). "Fructose-containing sugars and cardiovascular disease". Advances in Nutrition (Bethesda, Md.). 6 (4): 430–439. doi:10.3945/an.114.008177. ISSN 2156-5376. PMC 4496738. PMID 26178027.

[efsa11-14] EFSA Panel on Dietetic Products, Nutrition and Allergies (2011). "Scientific Opinion on the substantiation of health claims related to fructose and reduction of post-prandial glycaemic responses (ID 558) pursuant to Article 13(1) of Regulation (EC) No 1924/2006" (PDF). EFSA Journal. 9 (6): 2223. doi:10.2903/j.efsa.2011.2223.

[15] "Carbohydrates and Health" (PDF). UK Scientific Advisory Committee on Nutrition, Public Health England, TSO, Williams Lea, Norwich, UK. 2015. Retrieved 1 April 2016.

[16] "Institute of Organic Chemistry".

[17] McWilliams, Margaret. Foods: Experimental Perspectives, 4th Edition. ISBN 0-13-021282-2.

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v t e Metabolism: carbohydrate metabolism fructose and galactose enzymes

Fructose / Fructolysis	Hepatic fructokinase Aldolase B Triokinase

Sorbitol	Sorbitol dehydrogenase Aldose reductase

Galactose / Galactolysis	Galactokinase Galactose-1-phosphate uridylyltransferase/UDP-glucose 4-epimerase Aldose reductase

Lactose	Lactose synthase Lactase

Mannose	Mannose phosphate isomerase

リンク元	「フルクトース」「fructose」
関連記事	「fruit」「sugar」「sugars」

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fruit sugar