Stevioside

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Stevioside
Stevioside.svg
Names
IUPAC name
β-D-Glucopyranosyl 13-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy]-5β,8α,9β,10α,13α-kaur-16-en-18-oate
Systematic IUPAC name
(4R,4aS,6aR,9S,11aR,11bS)-9-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.055.414 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 260-975-5
KEGG
PubChem CID
UNII
  • InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1
  • C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)(C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
Properties
C38H60O18
Molar mass 804.8722
Appearancewhite powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stevioside is a glycoside derived from the stevia plant, which can be used as a sweetener. [1] Evidence of benefit is lacking for long-term effects on weight loss and heart disease risks. [2]

Origin

Stevioside is the main sweetener (along with rebaudioside A) found in the leaves of Stevia rebaudiana , a plant originating in South America. Dried leaves, as well as aqueous extracts, have been used for decades as a sweetener in many countries, notably in Latin America and Asia (Japan, China). [3] Stevioside was discovered in 1931 by French chemists who gave it its name. [3] The sweetening power of stevioside was estimated to be about 300 times stronger than cane sugar. [3]

Safety

Since 2008, the U.S. Food and Drug Administration has not objected to the use of stevia extracts and some purified steviosides, mainly stevioside and rebaudioside, as GRAS for use as an ingredient in manufactured foods. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

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.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

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.

<span class="mw-page-title-main">Neohesperidin dihydrochalcone</span> Chemical compound

Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. Acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

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.

<span class="mw-page-title-main">Diet soda</span> Type of sugar-free or artificially sweetened soda

Diet or light beverages are generally sugar-free, artificially sweetened beverages with few or no calories. They are marketed for diabetics and other people who want to reduce their sugar and/or caloric intake.

Saponins are bitter-tasting usually toxic plant-derived secondary metabolites, being organic chemicals, that have a foamy quality when agitated in water and a high molecular weight. They are present in a wide range of plant species throughout the bark, leaves, stems, roots and flowers but found particularly in soapwort, a flowering plant, the soapbark tree, common corn-cockle, baby's breath and soybeans. They are used in soaps, medicines, fire extinguishers, as dietary supplements, for synthesis of steroids, and in carbonated beverages. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<i>Stevia rebaudiana</i> Species of flowering plant

Stevia rebaudiana is a plant species in the genus Stevia of the family Asteraceae. It is commonly known as candyleaf, sweetleaf or sugarleaf.

<span class="mw-page-title-main">Sweetness</span> Basic taste

Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, and sugar alcohols. Some are sweet at very low concentrations, allowing their use as non-caloric sugar substitutes. Such non-sugar sweeteners include saccharin, aspartame, sucralose and stevia. Other compounds, such as miraculin, may alter perception of sweetness itself.

<i>Gymnema sylvestre</i> Species of flowering plant

Gymnema sylvestre is a perennial woody vine native to Asia, Africa and Australia. It has been used in Ayurvedic medicine. Common names include gymnema, Australian cowplant, and Periploca of the woods, and the Hindi term gurmar, which means "sugar destroyer".

<span class="mw-page-title-main">Steviol glycoside</span> Sweet chemicals derived from the Stevia plant

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 of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species S. phlebophylla and in the plant Rubus chingii (Rosaceae).

<span class="mw-page-title-main">Steviol</span> Chemical compound

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. Its chemical structure was not fully elucidated until 1960.

Rebiana is the trade name for high-purity rebaudioside A, a steviol glycoside that is 200 times as sweet as sugar. It is derived from stevia leaves by steeping them in water and purifying the resultant extract to obtain the rebaudioside A. The Coca-Cola Company filed patents on rebiana, and in 2007 it licensed the rights to the patents for food products to Cargill; Coca-Cola retained the exclusive rights to use the patents for beverage products. Truvia and PureVia are each made from rebiana and were each recognized as GRAS food ingredients by the US FDA in 2008.

The enzyme ent-kaurene synthase catalyzes the chemical reaction

PureVia is a stevia-based low calorie sugar substitute developed jointly by PepsiCo and Whole Earth Sweetener Company which is a wholly owned subsidiary of artificial sweetener manufacturing company Merisant.

<span class="mw-page-title-main">Rebaudioside A</span> Chemical compound

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.

<span class="mw-page-title-main">PureCircle</span>

PureCircle is a producer and innovator in the area of stevia sweeteners for the food and beverage industry. PureCircle has offices around the world, with the headquarters in Chicago, Illinois. It was listed on the London Stock Exchange until it was acquired by Ingredion in July 2020.

<i>Stevia</i> (genus) Family of shrubs

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.

References

  1. Ceunen S, Geuns JM (June 2013). "Steviol glycosides: chemical diversity, metabolism, and function". Journal of Natural Products. 76 (6): 1201–28. doi:10.1021/np400203b. PMID   23713723.
  2. Azad MB, Abou-Setta AM, Chauhan BF, Rabbani R, Lys J, Copstein L, et al. (July 2017). "Nonnutritive sweeteners and cardiometabolic health: a systematic review and meta-analysis of randomized controlled trials and prospective cohort studies". CMAJ. 189 (28): E929–E939. doi:10.1503/cmaj.161390. PMC   5515645 . PMID   28716847.
  3. 1 2 3 Scientific Committee on Food (17 June 1999). "Opinion On Stevioside as a Sweetener" (PDF). The European Commission. Archived from the original (PDF) on 9 July 2006.
  4. Perrier JD, Mihalov JJ, Carlson SJ (2018). "FDA regulatory approach to steviol glycosides". Food and Chemical Toxicology. 122: 132–142. doi: 10.1016/j.fct.2018.09.062 . ISSN   0278-6915. PMID   30268795.