Salidroside

Chemical compound From Wikipedia, the free encyclopedia

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea.[1] It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant.[2][3] Salidroside may be more active than rosavin,[4] even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

Quick facts Names, Identifiers ...
Salidroside
Names
IUPAC name
2-(4-Hydroxyphenyl)ethyl β-D-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
Other names
Salidroside
Rhodioloside
Tyrosol glucoside
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.224.258 Edit this at Wikidata
UNII
  • InChI=1S/C14H20O7/c15-7-10-11(17)12(18)13(19)14(21-10)20-6-5-8-1-3-9(16)4-2-8/h1-4,10-19H,5-7H2/t10-,11-,12+,13-,14-/m1/s1 ☒N
    Key: ILRCGYURZSFMEG-RKQHYHRCSA-N ☒N
  • InChI=1/C14H20O7/c15-7-10-11(17)12(18)13(19)14(21-10)20-6-5-8-1-3-9(16)4-2-8/h1-4,10-19H,5-7H2/t10-,11-,12+,13-,14-/m1/s1
    Key: ILRCGYURZSFMEG-RKQHYHRCBF
  • C1=CC(=CC=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Properties
C14H20O7
Molar mass 300.307 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Close

Bioactivities

Salidroside was shown to improve glucose homeostasis and alleviate diabetic retinopathy in obese mice.[5][6] The antioxidant, anti-inflammatory and neuroprotective effects of salidroside have also been reported.[7][8][9]

Biosynthesis

The salidroside biosynthetic pathway in Rhodiola rosea was described in 2018.[10] Rhodiola contains a pyridoxal phosphate-dependent 4-hydroxyphenylacetaldehyde (4-HPAA) synthase that converts tyrosine to 4-HPAA, which is further reduced to tyrosol by 4-HPAA reductase. Rhodiola contains a regio-selective tyrosol:UDP-glucose 8-O-glucosyltransferase that glycosylates tyrosol to produce salidroside.

References

Related Articles

Wikiwand AI