Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients (or precursors) of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species S. phlebophylla (but in no other species of Stevia ) and in the plant Rubus chingii (Rosaceae). [1]
Steviol glycosides from Stevia rebaudiana have been reported to be between 30 and 320 times sweeter than sucrose, [2] although there is some disagreement in the technical literature about these numbers. [1] [3] They are heat-stable, pH-stable, and do not ferment. [2]
Steviol glycosides do not induce a glycemic response when ingested, because humans cannot metabolize stevia. [4] [5] The acceptable daily intake (ADI) for steviol glycosides, expressed as steviol equivalents, has been established to be 4 mg/kg body weight/day, and is based on no observed effects of a 100 fold higher dose in a rat study. [6]
These compounds are glycosides of steviol. Specifically, their molecules can be viewed as a steviol molecule, with its carboxyl hydrogen atom replaced by a glucose molecule to form an ester, and a hydroxyl hydrogen with combinations of glucose and rhamnose to form an acetal.
The steviol glycosides found in S. rebaudiana leaves, and their dry weight percentage, include:
The last three are present only in minute quantities, and rebaudioside B has been claimed to be a byproduct of the isolation technique. [2] A commercial steviol glycoside mixture extracted from the plant was found to have about 80% stevioside, 8% rebaudioside A, and 0.6% rebaudioside C. [3]
The Chinese plant Rubus chingii produces rubusoside, a steviol glycoside not found in Stevia. [1] According to the EU Stevia Regulation of 13 July 2021, however, rubusoside is one of the eleven major glycoside components of Stevia, extracted from the leaves of the Stevia rebaudiana. [7]
Stevioside and rebaudioside A were first isolated in 1931 by French chemists, Bridel and Lavielle. [8] Both compounds have only glucose subgroups: stevioside has two linked glucose molecules at the hydroxyl site, whereas rebaudioside A has three, with the middle glucose of the triplet connected to the central steviol structure.
Early sensory tests led to claims that rebaudioside A was 150 to 320 times sweeter than sucrose, stevioside was 110 to 270 times sweeter, rebaudioside C 40 to 60 times sweeter, and dulcoside A 30 times sweeter. [2] However, a more recent evaluation found rebaudoside A to be about 240 times sweeter, and stevioside about 140 times. [1] Rebaudioside A also had the least bitterness and aftertaste. [2] The relative sweetness seems to vary with concentration: a mix of steviol glycosides in the natural proportions was found to be 150 times sweeter than sucrose when matching a 3% sucrose solution, but only 100 times sweeter when matching a 10% sucrose solution. [3]
In Stevia rebaudiana , the biosynthesis of the glucosides occurs only in green tissues. Steviol is first produced in the plastids and in the endoplasmic reticulum is glucosylated and glycosylated in the cytoplasm, catalyzed by UDP-glucosyltransferases. Rebaudioside A, in particular, is formed from stevioside.
Though there are several molecules that fall into the category of steviol glycoside, synthesis follows a similar route. [9] Synthesis of steviol glycoside begins with isoprene units created via the DXP or MEP pathway. [10] [11] Two molecules derived from primary metabolism, Pyruvate and Glyceraldehyde 3-Phosphate, are the initial molecules for this pathway.
Upon forming IPP and DMAPP, the diterpene GGPP is formed by via head-to-tail addition by an Sn1 mechanism. Elongation begins when IPP and DMAPP form Geranyl Pyrophosphate (GPP). GPP elongates through the same Sn1 mechanism to create Farnesyl Pyrophosphate (FPP), and FPP elongates to form GGPP.
With the formation of GGPP cyclization occurs by enzymes copalyl diphosphate synthase (CDPS) and Kuarene Synthase (KS) to form -(-)Kuarene. [12] Several oxidation steps then occur to form steviol.
Steviol glycoside biosynthesis then follows several modifications from steviol that regioselectively select for sugar molecules to be placed. [13] Once these molecules are fully glycosylated, the glycosides are then stored in vacuoles. [1]
Stevia is a sweet sugar substitute that is about 50 to 300 times sweeter than sugar. It is extracted from the leaves of Stevia rebaudiana, a plant native to areas of Paraguay and Brazil in the southern Amazon rainforest. The active compounds in stevia are steviol glycosides. Stevia is heat-stable, pH-stable, and not fermentable. Humans cannot metabolize the glycosides in stevia, and therefore it has zero calories. Its taste has a slower onset and longer duration than that of sugar, and at high concentrations some of its extracts may have an aftertaste described as licorice-like or bitter. Stevia is used in sugar- and calorie-reduced food and beverage products as an alternative for variants with sugar.
Fructose, or fruit sugar, is a ketonic simple sugar 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 by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.
A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
Stevioside is a glycoside derived from the stevia plant, which can be used as a sweetener. Evidence of benefit is lacking for long-term effects on weight loss and heart disease risks.
The mevalonate pathway, also known as the isoprenoid pathway or HMG-CoA reductase pathway is an essential metabolic pathway present in eukaryotes, archaea, and some bacteria. The pathway produces two five-carbon building blocks called isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are used to make isoprenoids, a diverse class of over 30,000 biomolecules such as cholesterol, vitamin K, coenzyme Q10, and all steroid hormones.
Trehalose is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.
Stevia rebaudiana is a plant species in the genus Stevia of the family Asteraceae. It is commonly known as candyleaf, sweetleaf or sugarleaf.
Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.
The non-mevalonate pathway—also appearing as the mevalonate-independent pathway and the 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate (MEP/DOXP) pathway—is an alternative metabolic pathway for the biosynthesis of the isoprenoid precursors isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). The currently preferred name for this pathway is the MEP pathway, since MEP is the first committed metabolite on the route to IPP.
Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.
Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata. Andrographolide is an extremely bitter substance.
Ribose 5-phosphate (R5P) is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose 5-phosphate. Depending on the body's state, ribulose 5-phosphate can reversibly isomerize to ribose 5-phosphate. Ribulose 5-phosphate can alternatively undergo a series of isomerizations as well as transaldolations and transketolations that result in the production of other pentose phosphates as well as fructose 6-phosphate and glyceraldehyde 3-phosphate.
UTP—glucose-1-phosphate uridylyltransferase also known as glucose-1-phosphate uridylyltransferase is an enzyme involved in carbohydrate metabolism. It synthesizes UDP-glucose from glucose-1-phosphate and UTP; i.e.,
The enzyme ent-kaurene synthase catalyzes the chemical reaction
Rosavin are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L.,. R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.
Rebaudioside A is a steviol glycoside from the leaves of Stevia rebaudiana that is 240 times sweeter than sugar. Rebaudioside A is the sweetest and most stable steviol glycoside, and is less bitter than stevioside. Stevia leaves contain 9.1% stevioside and 3.8% rebaudioside A.
Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.
Stevia is a genus of about 240 species of herbs and shrubs in the family Asteraceae, native to subtropical and tropical regions from western North America to South America. The species Stevia rebaudiana in this genus is widely grown for its extraction of sweet compounds from its leaves and sold as a sugar substitute known as stevia and other trade names.