Steviol

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Steviol
Steviol structure.svg
Steviol-3D ball-and-stick.png
Names
IUPAC name
13-Hydroxy-5β,8α,9β,10α,13α-kaur-16-en-18-oic acid
Systematic IUPAC name
(4R,4aS,6aR,9S,11aR,11bS)-9-Hydroxy-4,11b-dimethyl-8-methylidenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
Other names
Hydroxydehydrostevic acid
13-Hydroxykaurenoic acid
ent-13-Hydroxykaur-16-en-19-oic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1 Yes check.svgY
    Key: QFVOYBUQQBFCRH-VQSWZGCSSA-N Yes check.svgY
  • InChI=1/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1
    Key: QFVOYBUQQBFCRH-VQSWZGCSBR
  • O=C(O)[C@]4([C@H]3CC[C@@]21C[C@](O)(\C(=C)C1)CC[C@H]2[C@]3(C)CCC4)C
Properties
C20H30O3
Molar mass 318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931. [1] Its chemical structure was not fully elucidated until 1960. [2]

Contents

Steviol occurs in the plant as steviol glycosides, sweet compounds that have found widespread use as sugar substitutes. [3] The aglycon is prepared by enzymatic hydrolysis, since upon acid treatment steviol will undergo Wagner-Meerwein rearrangement to the very stable isosteviol.

Biosynthesis

In Stevia rebaudiana, the biosynthesis of steviol is confined to green tissues. The precursors of steviol are synthesized via the non-mevalonate pathway located in plant cell plastids, which produces isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). IPP and DMAPP are converted to geranylgeranyl diphosphate (GGDP), which is the precursor of many diterpenoids, by GGDP synthase. GPDP is made into a cyclic compound, copalyl diphosphate (CDP), by CDP synthase, after which kaurene is produced by another cyclization catalyzed by kaurene synthase.

The kaurene is then transferred to the endoplasmic reticulum, where it is oxidized to kaurenoic acid by kaurene oxidase in a reaction that uses up oxygen and NADPH. Then steviol is produced by hydroxylation. The steviol is subsequently glycosylated in the cytoplasm. [4]

Biosynthesis of steviol Bio synthesis of steviol glycoside 01.png
Biosynthesis of steviol

Related Research Articles

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Stevia is a sweet sugar substitute extracted from the leaves of the plant species Stevia rebaudiana native to Paraguay and Brazil.

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<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.

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

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

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(<i>E</i>)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate Chemical compound

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<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">Isopentenyl-diphosphate delta isomerase</span> Class of enzymes

Isopentenyl pyrophosphate isomerase, also known as Isopentenyl-diphosphate delta isomerase, is an isomerase that catalyzes the conversion of the relatively un-reactive isopentenyl pyrophosphate (IPP) to the more-reactive electrophile dimethylallyl pyrophosphate (DMAPP). This isomerization is a key step in the biosynthesis of isoprenoids through the mevalonate pathway and the MEP pathway.

<span class="mw-page-title-main">Bornyl diphosphate synthase</span>

In enzymology, bornyl diphosphate synthase (BPPS) (EC 5.5.1.8) is an enzyme that catalyzes the chemical reaction

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

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References

  1. Bridel, M.; Lavieille, R. (1931). "The sweet principle in Kaa-he-e (Stevia rebaudiana. Bertoni). II. Hydrolysis of stevioside by enzymes. III. Steviol by enzymic hydrolysis and isosteviol by acid hydrolysis". Bulletin de la Société de Chimie Biologique. 13: 781–796.
  2. Dolder, Fred; Lichti, Heinz; Mosettig, Erich; Quitt, Peter (1960). "The structure and stereochemistry of steviol and isosteviol". Journal of the American Chemical Society. 82: 246–247. doi:10.1021/ja01486a054.
  3. Brandle J. E., Starratt A. N., Gijzen M. (1998). "Stevia rebaudiana: Its agricultural, biological, and chemical properties". Canadian Journal of Plant Science. 78 (4): 527–536. doi: 10.4141/P97-114 .{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. 1 2 Brandle JE, Telmer PG (Jul 2007). "Steviol glycoside biosynthesis". Phytochemistry. 68 (14): 1855–63. Bibcode:2007PChem..68.1855B. doi:10.1016/j.phytochem.2007.02.010. PMID   17397883.