Rosavin

Last updated
Rosavin
Rosavin.svg
Names
IUPAC name
(2E)-3-Phenylprop-2-en-1-yl α-L-arabinopyranosyl-(1→6)-α-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{[(2E)-3-Phenylprop-2-en-1-yl]oxy}-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20+/m0/s1
  • C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC/C=C/C3=CC=CC=C3)O)O)O)O)O)O
Properties
C
20
H
28
O
10
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rosavin (also known as rosin, rosavin, and rosarin) are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L., (R. rosea). 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. [1] Rosavin production is specific to R. rosea and R. sachalinenis, [2] and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. [3] 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. [4]

Contents

Biosynthesis

Cinnamyl alcohol glycosides are products of phenylpropanoid metabolism, derived from phenylalanine, which is produced from the shikimic-chorismic acid pathway. [4] Shikimic acid is made from the precursor compounds erythrose-4-phosphate, and phosphoenolpyruvate. Shikimic acid is then converted to chorismic acid through various enzymes derived from the shikimic-chorismic acid pathway. Chorismate mutase then converts chorismic acid to prephenate via a Claisen rearrangement (1,3-sigmatropic rearrangement). Phenolpyruvate is generated by the decarboxylation of prephenate, and the loss of a water molecule. Phenylalanine ammonia lyase (PAL) then converts phenolpyruvate to phenylalanine by using L-glutamate as an amine donor, which is used in rosavin biosynthesis. In the first step of rosavin synthesis, PAL converts phenylalanine to cinnamic acid. [4] From cinnamic acid, cinnamyl-CoA ester is formed through hydroxycinnamate: CoA ligase (4CL). [4] This CoA ester is reduced to cinnamaldehyde by cinnamyl-CoA reductase (CCR). [4] The cinnamaldehyde is further reduced by cinnamyl alcohol dehydrogenase (CAD) to cinnamyl alcohol. [4] The enzymes that take part in the formation of the glycosides of cinnamyl alcohol are not yet known. [4] By one glucose transfer, rosin is formed, which is the simplest glycoside of R. rosea. [4] Rosavin is formed by the addition of an arabinose residue to rosin, while rosarin is generated by the addition of an arabinofuranose residue to rosin. [4] Depending on the sugar type, and the site it is attached to, various other glycosides may be formed. [4]

Biosynthetic Pathway to Produce Rosavins (Rosin, Rosavin, Rosarin) Rosavin Biosynthesis Final.tif
Biosynthetic Pathway to Produce Rosavins (Rosin, Rosavin, Rosarin)
Biosynthesis of L-Phenylalanine Phenylalanine biosynthesis Final 3.tif
Biosynthesis of L-Phenylalanine

Applications

Rosavins are considered to be the major active components of R. rosea, and clinical trials of R. rosea extract have reported positive efficacy on fatigue, depression, mountain sickness, and cardiovascular disease. [1] Extracts used in most clinical trials are standardized to a minimum of 3% cinnamyl alcohol glycosides and 0.8–1.0% salidroside, as the naturally occurring ratio of these compounds in the plant rhizomes is approximately 3:1. [4] Rosavins have also been reported to display immunomodulatory effects, radiation protection, anti-cancer activities, protective effects on bleomycin-induced pulmonary fibrosis, and induced antidepressant-like effects in mouse models. [1] The low content of rosavins in plants has limited further investigation of their activities, and there is great interest in producing rosavins using biotechnology. [1]

Related Research Articles

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

Cinnamaldehyde is an organic compound with the formula() C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

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

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

<i>Rhodiola rosea</i> Species of flowering plant in the stonecrop family Crassulaceae

Rhodiola rosea is a perennial flowering plant in the family Crassulaceae. It grows naturally in wild Arctic regions of Europe, Asia, and North America, and can be propagated as a groundcover.

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

Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle seeds, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others. Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio. The mixture exhibits a number of pharmacological effects, particularly in the fatty liver, non-alcoholic fatty liver, non-alcoholic steatohepatitis, and there is great clinical evidence for the use of silibinin as a supportive element in alcoholic and Child–Pugh grade 'A' liver cirrhosis. However, despite its several beneficial effects on the liver, silibinin and all the other compounds found in silymarin, especially silychristin seem to act as potent disruptors of the thyroid system by blocking the MCT8 transporter. The long term intake of silymarin can lead to some form of thyroid disease and if taken during pregnancy, silymarin can cause the development of the Allan–Herndon–Dudley syndrome. Although this information is not being taken into consideration by all regulatory bodies, several studies now consider silymarin and especially silychristin to be important inhibitors of the MCT8 transporter and a potential disruptor of the thyroid hormone functions.

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi, from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later.

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

Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.

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

Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.

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

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">3-Dehydroquinic acid</span> Chemical compound

3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7.

<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

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

The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

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

Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the hydrolysis of storax.

In enzymology, glutamate-prephenate aminotransferase is an enzyme that catalyzes the chemical reaction

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

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

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

Herbacetin is a flavonol, a type of flavonoid.

<span class="mw-page-title-main">Shikimate pathway</span> Biosynthetic Pathway

The shikimate pathway is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids. This pathway is not found in animal cells.

The biosynthesis of phenylpropanoids involves a number of enzymes.

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

(R)-prunasin is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.

<span class="mw-page-title-main">Rosin (chemical)</span> Chemical compound

Rosin is a glycoside ester of Cinnamyl alcohol and a constituent of Rhodiola rosea.

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

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

References

  1. 1 2 3 4 Bi H, Qu G, Wang S, Zhuang Y, Sun Z, Liu T, Ma Y (January 2022). "Biosynthesis of a rosavin natural product in Escherichia coli by glycosyltransferase rational design and artificial pathway construction". Metabolic Engineering. 69: 15–25. doi: 10.1016/j.ymben.2021.10.010 . PMID   34715353. S2CID   240229184.
  2. Dimpfel W, Schombert L, Panossian AG (2018-05-24). "Assessing the Quality and Potential Efficacy of Commercial Extracts of Rhodiola rosea L. by Analyzing the Salidroside and Rosavin Content and the Electrophysiological Activity in Hippocampal Long-Term Potentiation, a Synaptic Model of Memory". Frontiers in Pharmacology. 9: 425. doi: 10.3389/fphar.2018.00425 . PMC   5976749 . PMID   29881348.
  3. Grech-Baran M, Sykłowska-Baranek K, Krajewska-Patan A, Wyrwał A, Pietrosiuk A (March 2014). "Biotransformation of cinnamyl alcohol to rosavins by non-transformed wild type and hairy root cultures of Rhodiola kirilowii". Biotechnology Letters. 36 (3): 649–656. doi:10.1007/s10529-013-1401-5. PMC   3964300 . PMID   24190481.
  4. 1 2 3 4 5 6 7 8 9 10 11 György Z (2006). Glycoside production by in vitro Rhodiola rosea cultures. Oulu: University of Oulu. ISBN   951-42-8079-2. OCLC   141381688.