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Saponarin (Standard)

CAT: 0804-HY-N5083RSize: 1 EachDry Ice: NoHazardous: No
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Description
Saponarin (Standard) is the analytical standard of Saponarin. This product is intended for research and analytical applications. Saponarin is an orally active flavonoid compound. Saponarin can be isolated from Gypsophila trichotoma. Saponarin inhibits ERK/p38, NF-κB and MAPK phosphorylation and activates AMPK. Saponarin reduces IL-1β and COX-2. Saponarin has antioxidant, anti-inflammatory, hepatoprotective, hypoglycemic and hypotensive effects. Saponarin improves sleep disorders[1][2][3][4][5][6][7].
CAS Number
20310-89-8
UNSPSC
12352005
Target
AMPK; COX; Interleukin Related; NF-κB; p38 MAPK; PERK; Reference Standards
Type
Reference Standards
Related Pathways
Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; MAPK/ERK Pathway; NF-κB; Others; PI3K/Akt/mTOR
Field of Research
Metabolic Disease; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/saponarin-standard.html
Smiles
O=C1C=C(C2=CC=C(O)C=C2)OC3=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C([C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)C(O)=C13
Molecular Formula
C27H30O15
Molecular Weight
594.52
References & Citations
[1]Simeonova R, et al. Antidiabetic and antioxidant effects of saponarin from Gypsophila trichotoma on streptozotocin-induced diabetic normotensive and hypertensive rats. Phytomedicine. 2016 May 15;23 (5) :483-90.|[2]Seo KH, et al. Saponarin from barley sprouts inhibits NF-κB and MAPK on LPS-induced RAW 264.7 cells. Food Funct. 2014 Nov;5 (11) :3005-13.|[3]Seo WD, et al. Saponarin activates AMPK in a calcium-dependent manner and suppresses gluconeogenesis and increases glucose uptake via phosphorylation of CRTC2 and HDAC5. Bioorg Med Chem Lett. 2015 Nov 15;25 (22) :5237-42.|[4]Kamiyama M, et al. Flavonoids with potent antioxidant activity found in young green barley leaves. J Agric Food Chem. 2012 Jun 27;60 (25) :6260-7.|[5]Min SY, et al. Anti-Inflammatory and Anti-Allergic Effects of Saponarin and Its Impact on Signaling Pathways of RAW 264.7, RBL-2H3, and HaCaT Cells. Int J Mol Sci. 2021 Aug 5;22 (16) :8431.|[6]Vitcheva V, et al. Hepatoprotective effects of saponarin, isolated from Gypsophila trichotoma Wend. on cocaine-induced oxidative stress in rats. Redox Rep. 2011;16 (2) :56-61.|[7]Kim YR, et al. Effect of Hibiscus syriacus Linnaeus extract and its active constituent, saponarin, in animal models of stress-induced sleep disturbances and pentobarbital-induced sleep. Biomed Pharmacother. 2022 Feb;146:112301.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards
Isoform
COX-2; IL-1

Chemical Information

Saponarin

7-O-(beta-D-glucosyl)isovitexin is a C-glycosyl compound, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It has a role as a metabolite. It is functionally related to an isovitexin.

CAS Number20310-89-8
PubChem CID441381
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Molecular FormulaC27H30O15
Molecular Weight594.5
XLogP-1.6
Topological Polar Surface Area256
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count15
Rotatable Bond Count6
Heavy Atom Count42
Formal Charge0
Complexity971
SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
InChI
InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(40-15)18-14(41-27-25(38)23(36)20(33)16(8-29)42-27)6-13-17(21(18)34)11(31)5-12(39-13)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
InChIKey
HGUVPEBGCAVWID-KETMJRJWSA-N
Chemical Structure
2D Structure
2D structure of Saponarin
CAS: 20310-89-8
CID: 441381
Formula: C27H30O15
MW: 594.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight594.5
XLogP3-1.6
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count15
Rotatable Bond Count6
Exact Mass594.15847025
Monoisotopic Mass594.15847025
Topological Polar Surface Area256 Ų
Heavy Atom Count42
Formal Charge0
Complexity971
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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