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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.224.258
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).
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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.

References
  1. Mao Y, Li Y, Yao N (November 2007). "Simultaneous determination of salidroside and tyrosol in extracts of Rhodiola L. by microwave assisted extraction and high-performance liquid chromatography". Journal of Pharmaceutical and Biomedical Analysis. 45 (3): 510–5. doi:10.1016/j.jpba.2007.05.031. PMID 17628386.
  2. Perfumi M, Mattioli L (January 2007). "Adaptogenic and central nervous system effects of single doses of 3% rosavin and 1% salidroside Rhodiola rosea L. extract in mice". Phytotherapy Research. 21 (1): 37–43. doi:10.1002/ptr.2013. PMID 17072830. S2CID 46232827.
  3. Mattioli L, Funari C, Perfumi M (March 2009). "Effects of Rhodiola rosea L. extract on behavioural and physiological alterations induced by chronic mild stress in female rats". Journal of Psychopharmacology. 23 (2): 130–42. doi:10.1177/0269881108089872. PMID 18515456. S2CID 206489765.
  4. Panossian A, Nikoyan N, Ohanyan N, Hovhannisyan A, Abrahamyan H, Gabrielyan E, Wikman G (January 2008). "Comparative study of Rhodiola preparations on behavioral despair of rats". Phytomedicine. 15 (1–2): 84–91. doi:10.1016/j.phymed.2007.10.003. PMID 18054474.
  5. Wang, Meihong; Luo, Lan; Yao, Lili; Wang, Caiping; Jiang, Ketao; Liu, Xiaoyu; Xu, Muchen; Shen, Ningmei; Guo, Shaodong; Sun, Cheng; Yang, Yumin (May 2016). "Salidroside improves glucose homeostasis in obese mice by repressing inflammation in white adipose tissues and improving leptin sensitivity in hypothalamus". Scientific Reports. 6 (1): 25399. Bibcode:2016NatSR...625399W. doi:10.1038/srep25399. ISSN 2045-2322. PMC 4857131. PMID 27145908.
  6. Yao, Fei; Jiang, Xinyi; Qiu, Ling; Peng, Zixuan; Zheng, Wei; Ding, Lexi; Xia, Xiaobo (2022). "Long-Term Oral Administration of Salidroside Alleviates Diabetic Retinopathy in db/db Mice". Frontiers in Endocrinology. 13: 861452. doi:10.3389/fendo.2022.861452. ISSN 1664-2392. PMC 8966089. PMID 35370972.
  7. Zhong, Zhi-feng; Han, Jing; Zhang, Ji-Zhou; Xiao, Qing; Chen, Jing-yan; Zhang, Kai; Hu, Juan; Chen, Li-dian (2019-12-13). "Neuroprotective Effects of Salidroside on Cerebral Ischemia/Reperfusion-Induced Behavioral Impairment Involves the Dopaminergic System". Frontiers in Pharmacology. 10: 1433. doi:10.3389/fphar.2019.01433. ISSN 1663-9812. PMC 6923222. PMID 31920641.
  8. Song, Dan; Zhao, Min; Feng, Liuxiang; Wang, Pingyi; Li, Yimei; Li, Wenhua (October 2021). "Salidroside attenuates acute lung injury via inhibition of inflammatory cytokine production". Biomedicine & Pharmacotherapy. 142: 111949. doi:10.1016/j.biopha.2021.111949. ISSN 1950-6007. PMID 34325302.
  9. Ju, Linjie; Wen, Xiaohua; Wang, Chunjun; Wei, Yingjie; Peng, Yunru; Ding, Yongfang; Feng, Liang; Shu, Luan (2017-10-18). "Salidroside, A Natural Antioxidant, Improves β-Cell Survival and Function via Activating AMPK Pathway". Frontiers in Pharmacology. 8. doi:10.3389/fphar.2017.00749. ISSN 1663-9812. PMC 5651268. PMID 29093682.
  10. Torrens-Spence, Michael P.; Pluskal, Tomáš; Li, Fu-Shuang; Carballo, Valentina; Weng, Jing-Ke (2018-01-08). "Complete Pathway Elucidation and Heterologous Reconstitution of Rhodiola Salidroside Biosynthesis". Molecular Plant. 11 (1): 205–217. doi:10.1016/j.molp.2017.12.007. ISSN 1752-9867. PMID 29277428.


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