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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 Edit this at Wikidata
PubChem CID
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).
☒N  verify ( what is checkY☒N ?)

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

  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.


Stub icon

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

Retrieved from " https://en.wikipedia.org/?title=Salidroside&oldid=1170905770"
From Wikipedia, the free encyclopedia
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 Edit this at Wikidata
PubChem CID
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).
☒N  verify ( what is checkY☒N ?)

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

  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.


Stub icon

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

Retrieved from " https://en.wikipedia.org/?title=Salidroside&oldid=1170905770"

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