Chemistry:Sarmentosin
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| IUPAC name
(E)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C11H17NO7 | |
| Molar mass | 275.257 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Sarmentosin is a glycoside and that is found in several plant species, notably Ribes nigrum (blackcurrants) and Sedum sarmentosum.[1][2]
Chemical structure
Sarmentosin has a molecular formula of C11H17NO7 and a molecular weight of 275.25 g/mol. Its IUPAC name is (E)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile.[3]
Sources
Sarmentosin can be extracted from plants in the Rhodiola genus and blackcurrants. Recent studies have specifically identified sarmentosin as a key bioactive compound in blackcurrants that contributes to its monoamine oxidase inhibitory effects.[1]
Ecology
At least two Parnassius butterflies, Parnassius apollo and Parnassius smintheus, sequester sarmentosin and other hydroxynitrile glucosides in their bodies from the Sedum plants they eat.[4]
References
- ↑ 1.0 1.1 Lomiwes, Dominic; Günther, Catrin S.; Bloor, Stephen J.; Trower, Tania M.; Ngametua, Nayer; Kanon, Alexander P.; Jensen, Dwayne A.; Lo, Kim et al. (31 July 2024). "Identification of Sarmentosin as a Key Bioactive from Blackcurrants ( Ribes nigrum ) for Inhibiting Platelet Monoamine Oxidase in Humans". Journal of Agricultural and Food Chemistry 72 (30): 16777–16789. doi:10.1021/acs.jafc.4c03802. PMID 39028868. Bibcode: 2024JAFC...7216777L.
- ↑ Jiang, Zhitao; Yang, Xiang; Han, Yi; Li, Jie; Hu, Chen; Liu, Chundi; Xiao, Wei (September 2022). "Sarmentosin promotes USP17 and regulates Nrf2-mediated mitophagy and cellular oxidative stress to alleviate APAP-induced acute liver failure". Phytomedicine 104. doi:10.1016/j.phymed.2022.154337. PMID 35849971.
- ↑ "Sarmentosin" (in en). NIH, National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/Sarmentosin.
- ↑ Bjarnholt, Nanna; Nakonieczny, Mirosław; Kędziorski, Andrzej; Debinski, Diane M.; Matter, Stephen F.; Olsen, Carl Erik; Zagrobelny, Mika (May 2012). "Occurrence of Sarmentosin and Other Hydroxynitrile Glucosides in Parnassius (Papilionidae) Butterflies and Their Food Plants". Journal of Chemical Ecology 38 (5): 525–537. doi:10.1007/s10886-012-0114-x. PMID 22527055. Bibcode: 2012JCEco..38..525B.
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