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]

Related Research Articles

<span class="mw-page-title-main">Monoamine oxidase inhibitor</span> Type of medication

Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders.

<span class="mw-page-title-main">Monoamine oxidase</span> Family of enzymes

Monoamine oxidases (MAO) are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The first such enzyme was discovered in 1928 by Mary Bernheim in the liver and was named tyramine oxidase. The MAOs belong to the protein family of flavin-containing amine oxidoreductases.

<span class="mw-page-title-main">Saxifragales</span> Order of Eudicot flowering plants in the Superrosid clade

Saxifragales is an order of angiosperms, or flowering plants, containing 15 botanical families and around 100 genera, with nearly 2,500 species. Of the 15 families, many are small, with eight of them being monotypic. The largest family is the Crassulaceae (stonecrops), a diverse group of mostly succulent plants, with about 35 genera. Saxifragales are found worldwide, primarily in temperate to subtropical zones, rarely being encountered growing wild in the tropics; however, many species are now cultivated throughout the world as knowledge of plant husbandry has improved. They can be found in a wide variety of environments, from deserts to fully aquatic habitats, with species adapted to alpine, forested or fully-aquatic habitats. Many are epiphytic or lithophytic, growing on exposed cliff faces, on trees or on rocks, and not requiring a highly organic or nutrient-dense substrate to thrive.

<span class="mw-page-title-main">Blackcurrant</span> Species of flowering plant in the gooseberry family Grossulariaceae

The blackcurrant, also known as black currant or cassis, is a deciduous shrub in the family Grossulariaceae grown for its edible berries. It is native to temperate parts of central and northern Europe and northern Asia, where it prefers damp fertile soils. It is widely cultivated both commercially and domestically.

<i>Ribes</i> Genus of flowering plants in the order Saxifragales

Ribes is a genus of about 200 known species of flowering plants, most of them native to the temperate regions of the Northern Hemisphere. The species may be known as various kinds of currants, such as redcurrants, blackcurrants, and whitecurrants, or as gooseberries, and some are cultivated for their edible fruit or as ornamental plants. Ribes is the only genus in the family Grossulariaceae.

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<span class="mw-page-title-main">Swallowtail butterfly</span> Butterflies of family Papilionidae

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<span class="mw-page-title-main">Tyramine</span> Chemical compound

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<span class="mw-page-title-main">Monoamine oxidase A</span> Endogenous enzyme

Monoamine oxidase A, also known as MAO-A, is an enzyme that in humans is encoded by the MAOA gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative deamination of amines, such as dopamine, norepinephrine, and serotonin. A mutation of this gene results in Brunner syndrome. This gene has also been associated with a variety of other psychiatric disorders, including antisocial behavior. Alternatively spliced transcript variants encoding multiple isoforms have been observed.

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<span class="mw-page-title-main">Monoamine oxidase B</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">Antirrhinin</span> Chemical compound

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<span class="mw-page-title-main">Myrtillin</span> Chemical compound

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<span class="mw-page-title-main">Scopoletin</span> Chemical compound

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<i>Parnassius smintheus</i> Species of butterfly

Parnassius smintheus, the Rocky Mountain parnassian or Rocky Mountain apollo, is a high-altitude butterfly found in the Rocky Mountains throughout the United States and Canada. It is a member of the snow Apollo genus (Parnassius) of the swallowtail family (Papilionidae). The butterfly ranges in color from white to pale yellow-brown, with red and black markings that indicate to predators it is unpalatable.

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.