Saponarin

• CAT Number: M015574
• CAS Number: 20310-89-8
• Molecular Formula: C27H30O15
• Molecular Weight: 594.522
• Purity: ≥95%
• Synonyms: ISOVITEXIN-7-O-BETA-D-GLUCOPYRANOSIDE;ISOVITEXIN-7-O-GLUCOSIDE;SAPONARETIN-7-O-GLUCOSIDE;SAPONARIN;SAPONARIN WITH HPLC;SAPONARIN hplc;4/’,5-Dihydroxy-6-(β-D-glucopyranosyl)-7-(β-D-glucopyranosyloxy)flavone;6-(β-D-Glucopyranosyl)-7-[(β-D-glucopyranos
• Target: Disease Research Fields
• Storage: -20°C
• IUPAC Name: 5-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
• 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
• SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O

Saponarin is a flavone glucoside. It is found in Saponaria officinalis and in Strongylodon macrobotrys where it imparts the characteristic jade color to the flower. This coloration has been shown to be an example of copigmentation, a result of the presence of malvin (an anthocyanin) and saponarin in the ratio 1:9. Under the alkaline conditions (pH 7.9) found in the sap of the epidermal cells, this combination produced a blue-green pigmentation; the pH of the colorless inner floral tissue was found to be lower, at pH 5.6. Experiments showed that saponarin produced a strong yellow colouring in slightly alkaline conditions, resulting in the greenish tone of the flower. It is also found in passion flowers (Passiflora sp.).

Reference

1: Simeonova R, Vitcheva V, Krasteva I, Zdraveva P, Konstantinov S, Ionkova I.
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. doi: 10.1016/j.phymed.2016.02.024. Epub
2016 Mar 8. PubMed PMID: 27064007.

2: Seo WD, Lee JH, Jia Y, Wu C, Lee SJ. 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
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PMID: 26471090.

3: Seo KH, Park MJ, Ra JE, Han SI, Nam MH, Kim JH, Lee JH, Seo WD. Saponarin from
barley sprouts inhibits NF-κB and MAPK on LPS-induced RAW 264.7 cells. Food
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4: Simeonova R, Kondeva-Burdina M, Vitcheva V, Krasteva I, Manov V, Mitcheva M.
Protective effects of the apigenin-O/C-diglucoside saponarin from Gypsophila
trichotoma on carbone tetrachloride-induced hepatotoxicity in vitro/in vivo in
rats. Phytomedicine. 2014 Jan 15;21(2):148-54. doi: 10.1016/j.phymed.2013.07.014.
Epub 2013 Sep 4. PubMed PMID: 24011529.

5: Simeonova R, Vitcheva V, Kondeva-Burdina M, Krasteva I, Manov V, Mitcheva M.
Hepatoprotective and antioxidant effects of saponarin, isolated from Gypsophila
trichotoma Wend. on paracetamol-induced liver damage in rats. Biomed Res Int.
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6: Misawa K, Takahashi Y, Sato S. First synthesis of saponarin, 6-C- and
7-O-di-β-D-glucosylapigenin. Chem Pharm Bull (Tokyo). 2013;61(7):776-80. PubMed
PMID: 23812402.

7: Vitcheva V, Simeonova R, Krasteva I, Yotova M, Nikolov S, Mitcheva M.
Hepatoprotective effects of saponarin, isolated from Gypsophila trichotoma Wend.
on cocaine-induced oxidative stress in rats. Redox Rep. 2011;16(2):56-61. doi:
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