10338-51-9 Usage
Uses
Used in Pharmaceutical Industry:
Salidroside is used as a therapeutic agent for various health conditions due to its diverse pharmacological properties. It is particularly effective in the treatment of Alzheimer's disease, as it exhibits protective effects against neuronal death.
Used in Cardiovascular Health:
Salidroside is used as a cardioprotective agent, helping to counteract oxidative stress in cardiac-related conditions. Its antioxidant properties contribute to the maintenance of heart health.
Used in Antioxidant Formulations:
Salidroside is used as an effective antioxidant in various formulations, such as dietary supplements and skincare products. Its ability to neutralize free radicals helps protect the body from oxidative damage and supports overall health.
Used in Anti-cancer Treatments:
Salidroside is used as an anti-cancer agent, showing potential in inhibiting the growth and progression of cancer cells. Its synergistic effects with other compounds make it a promising candidate for cancer therapy.
Used in Memory Enhancement:
Salidroside is used as a memory-enhancing agent, improving cognitive function and supporting brain health.
Used in Anti-radiation Applications:
Salidroside is used as an anti-radiation agent, providing protection against the harmful effects of radiation exposure.
In combination with other compounds like rosavins, salidroside may exhibit enhanced effects, although more research is needed to fully understand its mechanisms of action and potential applications.
neuropharmacological activity
A number of studies have revealed that salidroside exhibits neuroprotective activities, including anti-Alzheimer’s disease, anti-Parkinson’s disease, anti-Huntington’s disease, anti-stroke, anti-depressive effects, and anti-traumatic brain injury; it is also useful for improving cognitive function, treating addiction, and preventing epilepsy. The mechanisms underlying the potential protective effects of salidroside involvement are the regulation of oxidative stress response, inflammation, apoptosis, hypothalamus-pituitary-adrenal axis, neurotransmission, neural regeneration, and the cholinergic system. Being free of side effects makes salidroside potentially attractive as a candidate drug for the treatment of neurological disorders.
in vitro
Salidroside (100 μM) inhibits prolyl endopeptidase (PEP) activity (10.6±1.9%). Prolyl endopeptidase is an enzyme that plays a role in the metabolism of proline-containing neuropeptidase which is recognized to be involved in learning and memory. Salidroside, one of the major phenylpropanoid glycosides found in R.?rosea L, is consumed almost daily as a nutritional supplement in many countries and has been identified possessing potential anti-fatigue and anoxia,anti-aging, and anti-Alzheimer's disease activities. Salidroside can improve muscle nutrition via increasing mTOR, p-mTOR, and MyHC expression. SH-SY5Y cells are exposed to 0-600?μM MPP+ for 12-48?h and the results show that MPP+ results in a significant decrease of cell viability in a concentration and time-dependent manner. Cells are pretreated with 25-100?μM Salidroside (Sal) for 24?h and then exposed to 500?μM MPP+ for an additional 24?h. Salidroside concentration-dependently prevents MPP+-induced decrease of cell viability. Annexin V/PI staining is a common method for the detection of apoptotic cell. Salidroside significantly decreases the number of Annexin V/PI-stained cells treated by MPP+ which is in a concentration-dependent manner. Apoptotic cell could also be morphologically evaluated by Hoechst staining. In Hoechst staining, apoptotic cells are characterized by reduced nuclear size, chromatin condensation, intense fluorescence, and nuclear fragmentation. Salidroside notably inhibits MPP+-induced increase of chromatin condensation, intense fluorescence, and nuclear fragmentation in SH-SY5Y cells.
In Vivo
Salidroside is a natural antioxidant extracted from medicinal food plant Rhodiola rosea. Salidroside (100 mg/kg/day) shows strong glucose lowering effect on db/db mice which is similar to effect of Metformin (200 mg/kg/day). For this reason, the dose of 100 mg/kg/day salidroside is used.
pharmacological properties
Salidroside (Rhodioloside), a phenylpropanoid glycoside isolated from Rhodiola rosea, has been reported to have a broad spectrum of pharmacological properties. Salidroside is a prolyl endopeptidase inhibitor. Salidroside alleviates cachexia symptoms in mouse models of cancer cachexia via activating mTOR signalling. Salidroside protects dopaminergic neurons by enhancing PINK1/Parkin-mediated mitophagy.
Biological activity
Salidroside is a glycoside that has been found in R. rosea and has diverse biological activities, including antioxidant, anti-apoptotic, neuroprotective, and anti-inflammatory properties.1,2,3,4,5 It scavenges 2,2-diphenyl-1-picrylhydrazyl and ABTS radicals with EC50 values of 81.54 and 30.94 μg/ml, respectively, in cell-free assays.2 Salidroside (50 and 100 μM) inhibits apoptosis and production of reactive oxygen species (ROS) induced by amyloid-β (25-35) (Aβ (23-35)) in SH-SY5Y neuroblastoma cells.3 It decreases infarct volume by 17.9% in a rat model of focal cerebral ischemia-reperfusion injury induced by transient middle cerebral artery occlusion (MCAO) when administered at a dose of 12 mg/kg.4 Salidroside (20, 50, and 100 mg/kg, p.o.) increases survival and reduces plasma alanine aminotransferase (ALT), aspartate aminotransferase (AST), TNF-α, and malondialdehyde (MDA) levels in a mouse model of liver injury induced by acetaminophen.
Plant extracts
Salidroside 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 treatment of neurasthenia and neurosis, and for improving attention and memory, high altitude polycythemia and hypertension. As a nervous stimulant, it is used to improve intellectual capacity, vegetative nervous system, vascular dystonia and myasthenia; it is also used for the treatment of diseases with increased free radical, such as cancer, radiation damage, emphysema, and senile cataracts; also used as a tonic for impotence. Salidroside preparation is also used in sports medicine and aerospace medicine, in health protection for people who work under various special environmental conditions.
Rhodiola has the functions of adaptogen and dual-direction regulation. After microwave radiation, monoamine neurotransmitters and cyclic adenosine monophosphate in spleen and thymus, lymphocyte transformation rate, and serum hemolysin in the brain of mice show prohibitive changes, and Rhodiola can make the changes back to normal. After injection of Salidroside, the functions of thyroid and adrenal in rabbits enhanced, and the secretion function in eggs of mouse was excited. It can improve concentration and memory and increase the level of β-indoxyl in plasma and prevent changes of stress hormones.
Rhodiola crenulata (Crassulaceae)
Rhodiola has nearly 100 species in the world, and they mainly distribute in the Himalayas, north-west Asia and North America. There are more than 80 species in China, mostly distributing in the southwest, northwest, north and northeast regions, and the main producing areas are Jilin, Hebei, Qinghai, Xinjiang, Sichuan, Yunnan, Guizhou, Tibet etc.
Rhodiola is a new developed important plant source of anti-fatigue, anti-aging and anti-anoxia medicines. Rhodiola extract is a product that extracted from dried rhizome of Rhodiola rosea L. as raw materials. Commercial extract generally contains 4% Salidroside.
Figure 1 is a figure of plant Rhodiola.
Modern medical research shows that the precious Rhodiola crenulata in genus Rhodiola containes rhodosin, salidroside, tyrosol salidroside, rhodiola lactone and 35 microelements, 18 amino acids , vitamin A, vitamin D, vitamin E and SOD.
The content of salidroside in different species of Rhodiola has large difference, and Wang Xiaoqin determined the content of salidroside in six Rhodiola species that native to Qinghai by HPLC method (see Table 6-5).
Pharmacological effects
1. Anti-fatigue effects: taking in Rhodiola kirilowii orally can prolong climbing time, swimming time and load swimming time in mice, and shorten the time required for recovery from fatigue, and improve levels of enzymes, RNA and protein, thus helping muscle to recover after fatigue as soon as possible.
2. The impact on the central nervous media: Rhodiola can normalize the content of 5-hydroxytryptamine under swimming conditions, meaning that the media content of central nervous is corrected to normal levels. Injection of salidroside (30-300mg/kg) can reduce the level of 5-hydroxytryptamine.
3. Anti-hypoxia effects: taking in Rhodiola kirilowii extract orally can make test animals show antagonism to all kinds of hypoxic mode, and the effect is stronger than that of ginseng and Acanthopanax.
4, Anti-aging effects: Rhodiola extract can increase the activity of red blood cells and liver SOD in rat and has the potential to increase the activity of myocardium SOD. Parasarcophaga similis can significantly prolong lifespan after taking in Rhodiola extract, and the rate of life extension is better than ginseng. Rhodiosin is known to promote 2BS cell proliferation and reduce mortality, and it can inhibit lipid peroxidation in rat and enhance the activity of superoxide dismutase.
5. Anti-tumor: Rhodosin has certain inhibition on S180 cells, and this effect was enhanced with increasing concentration in the non-toxic dose range. Continuously taking in Rhodiola extract orally can reduce the cancer-leading damage degree of rubomycin on intestinal wall in mice, and enhance the body's anti-cancer ability.
6. Detoxification: Salidroside can antagonize the intoxication of strychnine and improve the survival rate of mice with strychninism poisoning to 50%; it also has an antagonistic effect on Corynebacterium toxins and can protect against tetanus and other bacterial toxins, increasing the survival time or survival rate of the mice that take in potent poison, cyanide, or sodium nitrite.
Quantitative analysis of component of the natural medicine Rhodiola
[the test] Rhodiola kirilowii and dried roots, rhizomes or dry body of another species under genus Rhodiola, R. Sachalinensis .
(1) Chromatographic conditions: Column: μ-Bondapak ODS column (3.9mm × 30cm, 10μm); mobile phase: methanol-water (2: 8); flow rate: 1.0ml/min; column temperature: room temperature; detecting wavelength: 276nm .
(2) Preparation of the reference solution: accurately weighed appropriate amount of reference substance of Salidroside, and added methanol to produce the reference solution containing 0.04mg Salidroside per ml.
(3) Preparation of the sample solution: weighted precisely 1g the crude drug powder and placed it to Soxhlet extractor, and added 30ml methanol to extract for 2h; the extract was filtered and the filtrate was placed in a 50ml flask, and added methanol to the mark line and took it as the sample solution.
(4) Determination: took 10μl sample solution and 10μl reference solution to do sample injection and analyze.
(5) Chromatograms
Figure 3 is a high performance liquid chromatogram of Rhodiola (Ⅰ Rhodiola;.. Ⅱ 1. Rhodiola Rhodiola glycosides).
(6) Measurement results
Methods of Extraction and Isolation of Salidroside
Crush roots and rhizomes of Rhodiola into coarse powder and do reflux extraction with 70% ethanol, and fractionate the extracts and recover ethanol by depressurization, and add equal amount of water to the concentrate and stir, standing and flitting for 3 times. The filtrate is concentrated under reduced pressure, followed by the application of petroleum ether, chloroform, ethyl acetate, n-butanol, ethyl acetate and n-butanol to recover the solvent, respectively, and crude tyrosol and crude salidroside can be gained.
Check Digit Verification of cas no
The CAS Registry Mumber 10338-51-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,3,3 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 10338-51:
(7*1)+(6*0)+(5*3)+(4*3)+(3*8)+(2*5)+(1*1)=69
69 % 10 = 9
So 10338-51-9 is a valid CAS Registry Number.
InChI: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
10338-51-9Relevant articles and documents
Influence of the ionic liquid cosolvent on glucosylation reactions catalyzed by b-glycosidase for production of salidroside
Bi, Yanhong,Zhu, Chun,Wang, Zhaoyu,Jia, Jianbo
, p. 5095 - 5098 (2013)
The enzymatic synthesis of salidroside catalyzed by b-glycosidase from Malus pumila seed meal has been successfully carried out in ionic liquids-containing systems for the first time. The optimum conditions were screened out and the best yield of 24.9 % w
A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
Bassanini, Ivan,Krejzová, Jana,Panzeri, Walter,Monti, Daniela,K?en, Vladimir,Riva, Sergio
, p. 2040 - 2045 (2017)
A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.
Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
, p. 838 - 847 (2021)
Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium
Tong, Ai Min,Lu, Wen Ya,Xu, Jian He,Lin, Guo Qiang
, p. 2095 - 2097 (2004)
A facile method for enzymatic glycosylation of 4-substituted benzyl alcohols and tyrosol with glucose in a monophasic aqueous-dioxane medium was reported, using a crude meal of apple seed as a new catalyst. The corresponding β-D-glucosides were synthesized in moderate yields (13.1-23.1%), among which the salidroside was obtained in 15.8% yield.
Aryl β-d-glucosides from Carica papaya fruit
Schwab, Wilfried,Schreier, Peter
, p. 1813 - 1816 (1988)
Benzyl β-d-glucoside, 2-phenylethyl β-d-glucoside, 4-hydroxyphenyl-2-ethyl β-d-glucoside and four isomeric malonated benzyl β-d.
Ionic Liquid Effects on the Activity of β-Glycosidase for the Synthesis of Salidroside in Co-solvent Systems
Bi, Yanhong,Wang, Zhaoyu,Mao, Yanyong,Zheng, Shangyong,Zhang, Haijiang,Shi, Hao
, p. 1161 - 1165 (2012)
The preparation of salidroside was successfully carried out in fourteen ionic liquids (ILs)-containing systems using β-glycosidase from black plum seeds for the first time. The optimum conditions were determined for C6MIm·BF4, pH, phosphate buffer content, and molar ratio of tyrosol to D-glucose to be 1% (v/v), 5.9, 20% (v/v), and 8:1, under which the initial reaction rate and yield were 3.3 mmol/(L·h) and 24.5%, respectively. Moreover, the effects of 1-alkylimidazolium-based ILs possessing different alkyl chain lengths from C2 to C10 and a variety of anions including BF4-, PF6-, Cl-, Br-, and I- on enzyme activity in co-solvent systems were investigated. The results indicate that the optimal chain length of the alkyl substituent on the imidazolium ring of the cation was C6.
PHENOLIC GLUCOSIDES FROM PRUNUS GRAYANA
Shimomura, Hiroko,Sashida, Yutaka,Adachi, Tokuo
, p. 249 - 252 (1987)
A new bitter phenylpropanoid glucoside, 2-(4-hydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside and a new bitter tannin-related compound, 3,4,5-trimethoxybenzoyl-β-D-glucopyranoside, have been isolated together with known compounds, 2-(3,4-dihydroxyphyenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside,2-(3,4-dihydroxyphenyl)-ethyl-β-D-glucopyranoside and 6-O-caffeoyl-D-glucopyranose, from the bark of Prunus grayana.The structures of these compounds have been established on the basis of spectroscopic studies and chemical evidence. Key Word Index--Prunus grayana; Rosaceae; phenylpropanoid glucosides; tannin-related compound; caffeic acid esters; 3,4,5-trimethoxybenzoic acid ester.
Chemical synthesis method of salidroside
-
Paragraph 0019; 0024-0025; 0026; 0031-0032; 0033; 0036-0037, (2019/03/28)
The invention discloses a synthesis method of salidroside, wherein a phenolic hydroxyl group of a tyrosol is protected by a benzoyl group to carry out an acylation reaction, and beta-D-pent-acetyl glucose is used as a raw material and a glycosylation reaction is performed under the catalyst of zinc chloride and deprotection is performed in a methanol system of sodium methoxide. The synthesis method optimizes the synthesis route of salidroside, shortens the reaction steps, and improves the yield and the reaction conditions are mild, the operation is simple and easy, and the production cost is greatly reduced.
Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds
Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.
, p. 246 - 260 (2019/02/03)
β-Glucosidase from bitter almonds was immobilized on epoxy group-functionalized beads for catalyzing salidroside synthesis in a two-step process with n-butyl-β-D-glucoside (BG) as the glucosyl donor. The formation of salidroside ((0.59 ± 0.02) M) at a yield of 39.04%±1.25% was accomplished in 8 h by the transglucosylation of immobilized β-glucosidase at pH?8.0 and 50 °C when the ratio of BG to tyrosol was 1:2 (mol/mol). A study on the influence of different glycosyl acceptors demonstrated that the yield of the glucosylation reaction of phenylmethanol and cyclohexanol was higher than that of either phenol or cyclohexanol. This may account for the selectivity of the immobilized enzyme towards the alcoholic hydroxyl group of tyrosol in the salidroside synthesis reaction. A study on the synthesis of BG via the reverse hydrolysis of immobilized β-glucosidase showed that a yield of 78.04%±2.2% BG can be obtained with a product concentration of (0.23 ± 0.015) M.
Method for synthesizing salidroside by using [Rmim][OSO2OR]-Lewis acid ionic liquid system
-
, (2018/04/26)
The invention belongs to the technical field of catalytic synthesis and particularly relates to a method for synthesizing salidroside by using a [Rmim][OSO2OR]-Lewis acid ionic liquid system. According to the method, the salidroside compound is synthesized by using ionic liquid [Rmim][OSO2OR]. The synthesis of the ionic liquid provided by the invention needs only a one-step reaction, and atoms ofraw materials in a synthetic reaction of the ionic liquid are utilized by 100%, and thus, the reaction is an atomic-economical-efficiency reaction with simple and convenient operation. The method provided by the invention is environmentally friendly and is mild in reaction conditions and simple in aftertreatment, the problems such as environmental pollution caused by tedious synthesis of the ionicliquid used during the existing O-Glycosylation of a glycosyl trichloroacetimidate donor by using an ionic liquid system, thermal energy consumption, atom waste and a non-atomic-economical-efficiencyreaction are solved, and meanwhile, the problems such as environmental pollution and tedious aftertreatment caused by the existing salidroside drug chemical-synthesis in organic solvents are solved.
