Salidroside

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.

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
CAS Number	10338-51-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL465208 N
ChemSpider	140088 N
ECHA InfoCard	100.224.258
PubChem CID	159278
UNII	M983H6N1S9 N
CompTox Dashboard (EPA)	DTXSID4049034
InChI 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
SMILES C1=CC(=CC=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Properties
Chemical formula	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 YN ?) Infobox references

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.