Sophoricoside
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MedKoo CAT#: 464987

CAS#: 152-95-4

Description: Sophoricoside is a polyketide synthase-derived isoflavone glycoside that has been found in S. japonica and has diverse biological activities. It inhibits lipid accumulation induced by oleic acid in HepG2 cells and stimulates glucose uptake in C2C12 mouse skeletal muscle myoblasts when used at a concentration of 10 µM. Sophoricoside (2 mg/kg) reduces scratching behavior induced by compound 48/80 or histamine in mice, as well as reduces serum levels of IgE in a mouse model of atopic dermatitis. It increases serum levels of osteocalcin and alkaline phosphatase (ALP) and restores mechanical bone hardness in an ovariectomized rat model of osteoporosis. Sophoricoside (80 and 160 mg/kg) decreases hepatic cholesterol and triglyceride levels, serum LDL and apolipoprotein B levels, and hepatic injury in a mouse model of fructose-induced liver injury.

Chemical Structure

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Sophoricoside
CAS# 152-95-4
Instruction

Theoretical Analysis

MedKoo Cat#: 464987
Name: Sophoricoside
CAS#: 152-95-4
Chemical Formula: C21H20O10
Exact Mass: 432.11
Molecular Weight: 432.381
Elemental Analysis: C, 58.34; H, 4.66; O, 37.00

Price and Availability

Size Price Availability Quantity
50mg USD 240 2 Weeks
100mg USD 400 2 Weeks
250mg USD 720 2 Weeks
500mg USD 1120 2 Weeks
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Synonym: Sophoricoside; Genistein 4′-O-glucoside;

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

InChi Key: ISQRJFLLIDGZEP-CMWLGVBASA-N

InChi Code: InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-3-1-9(2-4-11)12-8-29-14-6-10(23)5-13(24)16(14)17(12)25/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1

SMILES Code: OC1=CC(O)=C2C(OC=C(C2=O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)=C1

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 57.82
DMSO 25.0 57.82
DMSO:PBS (pH 7.2) (1:2) 0.3 0.69

Preparing Stock Solutions

The following data is based on the product molecular weight 432.38 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: Bampali E, Germer S, Bauer R, Kulić Ž. HPLC-UV/HRMS methods for the unambiguous detection of adulterations of Ginkgo biloba leaves with Sophora japonica fruits on an extract level. Pharm Biol. 2021 Dec;59(1):438-443. doi: 10.1080/13880209.2021.1910717. PMID: 33886418; PMCID: PMC8079001.

2: Fan S, Zhang H, Wang Y, Zhao Y, Luo L, Wang H, Chen G, Xing L, Zheng P, Huang C. LXRα/β Antagonism Protects against Lipid Accumulation in the Liver but Increases Plasma Cholesterol in Rhesus Macaques. Chem Res Toxicol. 2021 Mar 15;34(3):833-838. doi: 10.1021/acs.chemrestox.0c00445. Epub 2021 Mar 1. PMID: 33647205.

3: Kim BH, Lee S. Sophoricoside from Styphnolobium japonicum improves experimental atopic dermatitis in mice. Phytomedicine. 2021 Feb;82:153463. doi: 10.1016/j.phymed.2021.153463. Epub 2021 Jan 14. PMID: 33545490.

4: Kim BH, Lee S. Sophoricoside from Sophora japonica ameliorates allergic asthma by preventing mast cell activation and CD4+ T cell differentiation in ovalbumin-induced mice. Biomed Pharmacother. 2021 Jan;133:111029. doi: 10.1016/j.biopha.2020.111029. Epub 2020 Nov 27. PMID: 33254020.

5: Wu YX, Zeng S, Wan BB, Wang YY, Sun HX, Liu G, Gao ZQ, Chen D, Chen YQ, Lu MD, Pang QF. Sophoricoside attenuates lipopolysaccharide-induced acute lung injury by activating the AMPK/Nrf2 signaling axis. Int Immunopharmacol. 2021 Jan;90:107187. doi: 10.1016/j.intimp.2020.107187. Epub 2020 Nov 25. PMID: 33249045.

6: Gao M, Hu F, Hu M, Hu Y, Shi H, Zhao GJ, Jian C, Ji YX, Zhang XJ, She ZG, Li H, Zhu L. Sophoricoside ameliorates cardiac hypertrophy by activating AMPK/mTORC1-mediated autophagy. Biosci Rep. 2020 Nov 27;40(11):BSR20200661. doi: 10.1042/BSR20200661. PMID: 32964914; PMCID: PMC7677750.

7: Zhang Y, Li F, Jiang X, Jiang X, Wang Y, Zhang H, Zhang L, Fan S, Xin L, Yang B, Ji G, Huang C. Sophoricoside is a selective LXRβ antagonist with potent therapeutic effects on hepatic steatosis of mice. Phytother Res. 2020 Dec;34(12):3168-3179. doi: 10.1002/ptr.6747. Epub 2020 Jun 27. PMID: 32592532.

8: Elberry A, Mufti S, Al-Maghrabi J, Ghareib S, Mosli H, El-Halawany A, Abdel- Sattar E. The protective effect of Sophora japonica on prostatic hypertrophy and inflammation in rat. Inflammopharmacology. 2020 Dec;28(6):1525-1536. doi: 10.1007/s10787-020-00723-5. Epub 2020 Jun 5. PMID: 32504221.

9: Han R, Ni J, Zhou J, Dong J, Xu G, Ni Y. Engineering of Cyclodextrin Glycosyltransferase Reveals pH-Regulated Mechanism of Enhanced Long-Chain Glycosylated Sophoricoside Specificity. Appl Environ Microbiol. 2020 Mar 18;86(7):e00004-20. doi: 10.1128/AEM.00004-20. PMID: 32005733; PMCID: PMC7082579.

10: Wang Y, Liu L, Ma Y, Guo L, Sun Y, Liu Q, Liu J. Chemical Discrimination of Astragalus mongholicus and Astragalus membranaceus Based on Metabolomics Using UHPLC-ESI-Q-TOF-MS/MS Approach. Molecules. 2019 Nov 9;24(22):4064. doi: 10.3390/molecules24224064. PMID: 31717584; PMCID: PMC6891664.

11: Mei J, Chen X, Liu J, Yi Y, Zhang Y, Ying G. A Biotransformation Process for Production of Genistein from Sophoricoside by a Strain of Rhizopus oryza. Sci Rep. 2019 Apr 25;9(1):6564. doi: 10.1038/s41598-019-42996-z. PMID: 31024087; PMCID: PMC6484079.

12: Xing C, Zhang GS, Gong NB, Hua Du G, Lu Y. New crystal forms and amorphous phase of sophoricoside: X-ray structures and characterization. R Soc Open Sci. 2019 Jan 23;6(1):181905. doi: 10.1098/rsos.181905. PMID: 30800407; PMCID: PMC6366211.

13: Li W, Lu Y. Hepatoprotective Effects of Sophoricoside against Fructose- Induced Liver Injury via Regulating Lipid Metabolism, Oxidation, and Inflammation in Mice. J Food Sci. 2018 Feb;83(2):552-558. doi: 10.1111/1750-3841.14047. Epub 2018 Jan 19. PMID: 29350757.

14: Zhang X, Yin J, Liang C, Sun Y, Zhang L. A simple and sensitive UHPLC-Q-TOF- MS/MS method for sophoricoside metabolism study in vitro and in vivo. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 1;1061-1062:193-208. doi: 10.1016/j.jchromb.2017.07.003. Epub 2017 Jul 18. PMID: 28750233.

15: Wang S, Zhang J, Liu J, Qian G, Fu C. Quality evaluation of Huaijiao pill by chromatographic fingerprint and simultaneous determination of its major bioactive components. J Pharm Anal. 2016 Aug;6(4):249-255. doi: 10.1016/j.jpha.2016.03.001. Epub 2016 Mar 15. PMID: 29403990; PMCID: PMC5762603.

16: Zhi XR, Zhang ZY, Jia PP, Zhang XX, Yuan L, Sheng N, Zhang LT. Qualitative and quantitative determination of 15 main active constituents in Fructus Sophorae pill by liquid chromatography tandem mass spectrometry. Pharmacogn Mag. 2015 Jan-Mar;11(41):196-207. doi: 10.4103/0973-1296.149739. PMID: 25709233; PMCID: PMC4329624.

17: Feng C, Jin S, Xia XX, Guan Y, Luo M, Zu YG, Fu YJ. Effective bioconversion of sophoricoside to genistein from Fructus sophorae using immobilized Aspergillus niger and Yeast. World J Microbiol Biotechnol. 2015 Jan;31(1):187-97. doi: 10.1007/s11274-014-1777-y. Epub 2014 Nov 13. PMID: 25392205.

18: Abdallah HM, Al-Abd AM, Asaad GF, Abdel-Naim AB, El-halawany AM. Isolation of antiosteoporotic compounds from seeds of Sophora japonica. PLoS One. 2014 Jun 3;9(6):e98559. doi: 10.1371/journal.pone.0098559. PMID: 24892557; PMCID: PMC4043785.

19: Zhou J, Qu C, Sun Q, Wu L, Liu Y, Yang Z, Zhang J. Sophoricoside fails the embryo implantation by compromising the uterine endometrial receptivity at implantation "window" of pregnant mice. Chem Biol Interact. 2014 Aug 5;219:57-63. doi: 10.1016/j.cbi.2014.05.009. Epub 2014 May 28. PMID: 24877640.

20: Ruby, Santosh Kumar RJ, Vishwakarma RK, Singh S, Khan BM. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera. Mol Biol Rep. 2014 Jul;41(7):4675-88. doi: 10.1007/s11033-014-3338-8. Epub 2014 Mar 25. PMID: 24664316.