Chemistry:Salidroside
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| IUPAC name
2-(4-Hydroxyphenyl)ethyl β-D-glucopyranoside
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| 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)
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
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.
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
- ↑ "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. November 2007. doi:10.1016/j.jpba.2007.05.031. PMID 17628386.
- ↑ "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. January 2007. doi:10.1002/ptr.2013. PMID 17072830.
- ↑ "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. March 2009. doi:10.1177/0269881108089872. PMID 18515456.
- ↑ "Comparative study of Rhodiola preparations on behavioral despair of rats". Phytomedicine 15 (1–2): 84–91. January 2008. doi:10.1016/j.phymed.2007.10.003. PMID 18054474.
- ↑ Wang, Meihong; Luo, Lan; Yao, Lili; Wang, Caiping; Jiang, Ketao; Liu, Xiaoyu; Xu, Muchen; Shen, Ningmei et al. (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. doi:10.1038/srep25399. ISSN 2045-2322. PMID 27145908. Bibcode: 2016NatSR...625399W.
- ↑ 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. PMID 35370972.
- ↑ 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. PMID 31920641.
- ↑ 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.
- ↑ 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. PMID 29093682.
- ↑ 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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