Saponarin
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MedKoo CAT#: 461785

CAS#: 20310-89-8

Description: Saponarin is a flavone glucoside isolated from Gypsophila trichotoma Wend. that has antioxidant and hepatoprotective activities.

Chemical Structure

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Saponarin
CAS# 20310-89-8
Instruction

Theoretical Analysis

MedKoo Cat#: 461785
Name: Saponarin
CAS#: 20310-89-8
Chemical Formula: C27H30O15
Exact Mass: 594.16
Molecular Weight: 594.520
Elemental Analysis: C, 54.55; H, 5.09; O, 40.37

Price and Availability

Size Price Availability Quantity
5mg USD 380 2 Weeks
10mg USD 720 2 Weeks
25mg USD 1350 2 Weeks
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Synonym: Saponarin;

IUPAC/Chemical Name: 5-hydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: HGUVPEBGCAVWID-KETMJRJWSA-N

InChi Code: 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

SMILES Code: O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=C([C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)C(O[C@H]5[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 594.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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 15;25(22):5237-42. doi: 10.1016/j.bmcl.2015.09.057. Epub 2015 Sep 26. PubMed PMID: 26471090.

2: 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.

3: 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.

4: 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 Funct. 2014 Nov;5(11):3005-13. doi: 10.1039/c4fo00612g. PubMed PMID: 25238253.

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. 2013;2013:757126. doi: 10.1155/2013/757126. Epub 2013 Jun 26. PubMed PMID: 23878818; PubMed Central PMCID: PMC3708395.

6: 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.

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: 10.1179/174329211X12989133691530. PubMed PMID: 21722413.

8: Kamiyama M, Shibamoto T. Flavonoids with potent antioxidant activity found in young green barley leaves. J Agric Food Chem. 2012 Jun 27;60(25):6260-7. doi: 10.1021/jf301700j. Epub 2012 Jun 18. Review. PubMed PMID: 22681491.

9: Sengupta S, Mukherjee A, Goswami R, Basu S. Hypoglycemic activity of the antioxidant saponarin, characterized as alpha-glucosidase inhibitor present in Tinospora cordifolia. J Enzyme Inhib Med Chem. 2009 Jun;24(3):684-90. doi: 10.1080/14756360802333075. PubMed PMID: 18951283.

10: SEIKEL MK, GEISSMAN TA. The flavonoid constituents of barley (Horedum vulgare). I. Saponarin. Arch Biochem Biophys. 1957 Sep;71(1):17-30. PubMed PMID: 13459424.

11: Chen T, Li HM, Zou DL, Du YZ, Shen YH, Li Y. Preparation of two flavonoid glycosides with unique structures from barley seedlings by membrane separation technology and preparative high-performance liquid chromatography. J Sep Sci. 2014 Dec;37(24):3760-6. doi: 10.1002/jssc.201400798. Epub 2014 Nov 4. PubMed PMID: 25283274.

12: Marinova K, Kleinschmidt K, Weissenböck G, Klein M. Flavonoid biosynthesis in barley primary leaves requires the presence of the vacuole and controls the activity of vacuolar flavonoid transport. Plant Physiol. 2007 May;144(1):432-44. Epub 2007 Mar 16. PubMed PMID: 17369433; PubMed Central PMCID: PMC1913782.

13: Zuo YM, Liu DH, Zhang ZL, Cai MT. [Study on chemical components of Tripterospermum chinense]. Zhong Yao Cai. 2014 Nov;37(11):2002-4. Chinese. PubMed PMID: 26027120.

14: Shibamoto T. A novel gas chromatographic method for determination of malondialdehyde from oxidized DNA. Methods Mol Biol. 2015;1208:49-62. doi: 10.1007/978-1-4939-1441-8_4. PubMed PMID: 25323498.

15: Lee YH, Kim JH, Kim SH, Oh JY, Seo WD, Kim KM, Jung JC, Jung YS. Barley Sprouts Extract Attenuates Alcoholic Fatty Liver Injury in Mice by Reducing Inflammatory Response. Nutrients. 2016 Jul 21;8(7). pii: E440. doi: 10.3390/nu8070440. PubMed PMID: 27455313; PubMed Central PMCID: PMC4963916.

16: Park MJ, Ra JE, Seo KH, Jang KC, Han SI, Lee JH, Kang YH, Nam MH, Seo WD. Identification and evaluation of flavone-glucosides isolated from barley sprouts and their inhibitory activity against bacterial neuraminidase. Nat Prod Commun. 2014 Oct;9(10):1469-72. PubMed PMID: 25522538.

17: Chomicki G, Bidel LP, Ming F, Coiro M, Zhang X, Wang Y, Baissac Y, Jay-Allemand C, Renner SS. The velamen protects photosynthetic orchid roots against UV-B damage, and a large dated phylogeny implies multiple gains and losses of this function during the Cenozoic. New Phytol. 2015 Feb;205(3):1330-41. doi: 10.1111/nph.13106. Epub 2014 Oct 23. PubMed PMID: 25345817.

18: Frangne N, Eggmann T, Koblischke C, Weissenböck G, Martinoia E, Klein M. Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms. Plant Physiol. 2002 Feb;128(2):726-33. PubMed PMID: 11842175; PubMed Central PMCID: PMC148933.

19: Obmann A, Purevsuren S, Zehl M, Kletter C, Reznicek G, Narantuya S, Glasl S. HPLC determination of flavonoid glycosides in Mongolian Dianthus versicolor Fisch. (Caryophyllaceae) compared with quantification by UV spectrophotometry. Phytochem Anal. 2012 May-Jun;23(3):254-9. doi: 10.1002/pca.1351. Epub 2011 Sep 7. PubMed PMID: 21898629.

20: Ishihara A, Ogura Y, Tebayashi S, Iwamura H. Jasmonate-induced changes in flavonoid metabolism in barley (Hordeum vulgare) leaves. Biosci Biotechnol Biochem. 2002 Oct;66(10):2176-82. PubMed PMID: 12450129.