Salidroside

White to off-white solidSalidroside is a compound that extracted from dry roots, rhizomes or the whole dry body of Rhodiola wallichiana (Crassulaceae), with the function of preventing cancer, enhancing immunologic function, anti-aging, anti-fatigue, anti-anoxia, anti-radiation, dual-direction regulation of central nervous system, and repairing and protecting the body and so on. It is commonly used as a treatment for chronic diseases and frail susceptible patients. Clinically, it is used for the

Salidroside is a glycoside.

3) 1 g of sodium methoxide (50percent content) in methanol was added to the filtrate, and the mixture was stirred at room temperature for 2 hours. Acidic cation exchange resin (732) was to adjust the pH to 7, filtered and the filtrate was removed. The filtrate was added with activated carbon (2percent) and decolorized at 70 ° C for 1 hour, filtererd, the filtrate was concentrated under reduced pressure and dissolved in 15 ml of water. The mixture was extracted 4 times with ethyl acetate (10 ml / time), the organic phase was separated. The water phase was combined, the aqueous phase was concentrated to half volume at 60 ° C under reduced pressure, extracted 4 times with n-butanol (10ml / time), the aqueous phase was separated, and the organic phases were combined. The organic phase was rotated under reduced pressure to spin-out n-butanol to give a concentrate. 4) The concentrate was recrystallized from acetone: n-butanol = 3:1 to obtain 2.30 g of salidroside, the yield is 89.8percent, purity 98percent.General procedure: Glycoside 21a–c, 22, 23 and 25–30 was dissolved in dry MeOH (9 mL), cooled to 4 °C and 0.5 M MeONa (1 mL) was added dropwise. The mixture was stirred at 4 °C until TLC (EtOAc/MeOH 6:1) showed that the reaction is complete. The pH of the mixture was brought pH 5 using Amberlite IR 120 (H+ form). The resin was filtered off, the filtrate concentrated and the residue was subjected to column chromatography (EtOAc/MeOH 1:06:1).2-(4-acetoxyphenyl)ethyl(2, 3, 4, 6-O-tetraacetyl)-β-D-glucopyranoside 30 g was added 500 mL round bottom flask 95percent ethanol 717 strong acidic cationic resin 20g, 70 reflux overnight, TLC tracking to complete reaction, cooling to room temperature, the cationic resin recovery, ethanol and water were distilled off under reduced pressure, 100 ml of ethyl acetate was added, and the mixture was refluxed for 1 hour and then slowly cooled to room temperature, precipitation of white solid, filter, 40-60 dryness 10-12 hours to give salidroside, purity 98.2percent, yield 86.5percent.1.1 g (2.8 mmol) of 1-O-(4-benzyloxy)-phenylethyl yl -β-D- glucopyranoside and 5percent Pd / C 0.1 g of catalyst, and then repeatedly evacuated air charge of hydrogengas 3-5 times, and 20 mL of anhydrous methanol, protected from light, stirred at room temperature under a hydrogen atmosphere overnight.Filtration, concentration to dryness under reduced pressure, and recrystallized from ethanol to give 1-(4-hydroxy)-phenethyl-β-D-s-glucopyranoside as a white powder, which is aweight of 0.78 g. The yield was 93percent.Reaction mixture (100 mL) comprising of 2.0725 g (1.5 mmol) tyrosol, 15.4 g cellobiose and Novozyme 188 (735 U of β-glucosidase) in distilled water was incubated at 37 °C. The reaction was stopped after 3 h by boiling in water bath for 5 min, centrifuged for 10 min at 4500 rpm and filtered through 0.22 m filter (25 mm diameter). The filtrate was applied on column of Sephadex LH-20 (75 cm long, 3.2 mm i.d.) equilibrated and eluted with distilled water. Tyrosol was regenerated by gradient of ethanol. The process of purification was monitored by TLC. Fractions containing salidroside were collected and concentrated in vacuo. To remove coloured substances originating from the enzyme, the material was further subjected to flash chromatography with gradient of methanol in chloroform. Fractions containing pure salidroside were concentrated and crystallised from mixture of methanol and chloroform (1:5, v/v).General procedure: The different seed meals were prepared as described by Yuet al. [10]. The reaction was performed in a 10 ml Erlenmeyershaking flask capped with a septum containing 1.6 ml dioxane, 0.4 ml phosphate buffer (pH 6.8, 100 mmol/L), 0.5 mmolD-glucose, 5 mmol tyrosol, and different fruit seed meal at 50°C and 200 r/min. Aliquots were withdrawn at specified timeintervals from the reaction mixture, and then diluted 50 timeswith the corresponding mobile phase prior to HPLC analysis.One unit of -glycosidase activity (U) was defined as theamount of enzyme required to produce 1 μmol salidroside inthe first hour under the above conditions. The specific activitiesof the black plum seed meal, apple seed meal, peach seed meal, bitter almond seed meal, and prune seed meal were 27.6, 23.4, 25.9, 13.5, and 19.7 U/g.

Salidroside (Rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It is thought to be one of the compounds responsible for the antidepressant and anxiolytic actions of this plant, along with rosavin. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardised for rosavin content rather than salidroside.

Molecular Weight:300.30
XLogP3:-0.6
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:300.12090297
Monoisotopic Mass:300.12090297
Topological Polar Surface Area:120
Heavy Atom Count:21
Complexity:306
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes