Sarmentosin

Last updated
Sarmentosin
Sarmentosin.svg
Names
IUPAC name
(E)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C11H17NO7/c12-3-6(4-13)1-2-18-11-10(17)9(16)8(15)7(5-14)19-11/h1,7-11,13-17H,2,4-5H2/b6-1+/t7-,8-,9+,10-,11-/m1/s1
    Key: FWAYDNJCBHNWQD-JBWLPIRVSA-N
  • C(/C=C(/CO)\C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
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).

Sarmentosin is a glycoside and that is found in several plant species, notably Ribes nigrum (blackcurrants) and Sedum sarmentosum . [1] [2]

Contents

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. 1 2 Lomiwes, Dominic; Günther, Catrin S.; Bloor, Stephen J.; Trower, Tania M.; Ngametua, Nayer; Kanon, Alexander P.; Jensen, Dwayne A.; Lo, Kim; Sawyer, Greg; Walker, Edward G.; Hedderley, Duncan; Cooney, Janine M. (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. Bibcode:2024JAFC...7216777L. doi: 10.1021/acs.jafc.4c03802 . PMC   11299169 . PMID   39028868.
  2. ↑ 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: 154337. doi:10.1016/j.phymed.2022.154337. PMID   35849971.
  3. ↑ "Sarmentosin". PubChem. NIH, National Library of Medicine. Retrieved 20 December 2024.
  4. ↑ 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. Bibcode:2012JCEco..38..525B. doi:10.1007/s10886-012-0114-x. PMID   22527055.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.