Glabridin
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MedKoo CAT#: 540177

CAS#: 59870-68-7

Description: Glabridin is a GABA-A receptor positive modulator found in Glycyrrhiza. It promotes fatty acid oxidation, suppreses adipogenesis, improves learning and memory, and inhibits Rho signaling by decreasing FAK and Src activation.

Chemical Structure

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Glabridin
CAS# 59870-68-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540177
Name: Glabridin
CAS#: 59870-68-7
Chemical Formula: C20H20O4
Exact Mass: 324.14
Molecular Weight: 324.376
Elemental Analysis: C, 74.06; H, 6.22; O, 19.73

Price and Availability

Size Price Availability Quantity
10mg USD 190
25mg USD 350
50mg USD 650
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Synonym: Glabridin ; Q-100692; Q100692; Q 100692; KB-289522; KB289522; KB 289522; LS-176045; LS176045; LS 176045

IUPAC/Chemical Name: (R)-4-(8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl)benzene-1,3-diol

InChi Key: LBQIJVLKGVZRIW-ZDUSSCGKSA-N

InChi Code: InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1

SMILES Code: OC1=CC=C([C@H]2CC3=CC=C4C(C=CC(C)(C)O4)=C3OC2)C(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: Soluble in DMSO

Shelf Life: >2 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: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Glabridin is a natural isoflavan from Glycyrrhiza glabra, binds to and activates PPARγ, with an EC50 of 6115 nM.
In vitro activity: The results showed that treatment of 1200μg/ml Sodium iodate (NaIO3) significantly reduced the cell viability compared with the control group, while treatment with 2, 4, and 8μM Glab (glabridin) significantly attenuated NaIO3-induced cell death compared with the NaIO3 group (Figure 1B). Reference: Front Pharmacol. 2020 Oct 15;11:566699. https://pubmed.ncbi.nlm.nih.gov/33178017/
In vivo activity: Western blot analysis revealed that GLA (glabridin) suppressed DOX-induced cleaved-caspase 3 and cleaved-caspase 9 activation. While DOX suppressed expression of anti-apoptotic proteins HAX-1 and Bcl-2, GLA dramatically upregulated the proteins expression of HAX-1 and Bcl-2 (Figure 1G). These results suggest that GLA is effective in protecting against DOX-induced cardiotoxicity in mice. Reference: Biol Pharm Bull. 2020 May 1;43(5):884-897. https://pubmed.ncbi.nlm.nih.gov/32147624/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 92.49
DMF:PBS (pH 7.2) (1:6) 0.1 0.43
DMSO 36.3 112.01
Ethanol 20.0 61.66

Preparing Stock Solutions

The following data is based on the product molecular weight 324.38 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: 1. Aung KH, Liu H, Ke Z, Jiang S, Huang J. Glabridin Attenuates the Retinal Degeneration Induced by Sodium Iodate In Vitro and In Vivo. Front Pharmacol. 2020 Oct 15;11:566699. doi: 10.3389/fphar.2020.566699. PMID: 33178017; PMCID: PMC7593553. 2. Heo JS, Lee SG, Kim HO. The Flavonoid Glabridin Induces OCT4 to Enhance Osteogenetic Potential in Mesenchymal Stem Cells. Stem Cells Int. 2017;2017:6921703. doi: 10.1155/2017/6921703. Epub 2017 Nov 14. PMID: 29348759; PMCID: PMC5733956. 3. Parlar A, Arslan SO, Çam SA. Glabridin Alleviates Inflammation and Nociception in Rodents by Activating BKCa Channels and Reducing NO Levels. Biol Pharm Bull. 2020 May 1;43(5):884-897. doi: 10.1248/bpb.b20-00038. Epub 2020 Mar 6. PMID: 32147624. 4. Huang K, Liu Y, Tang H, Qiu M, Li C, Duan C, Wang C, Yang J, Zhou X. Glabridin Prevents Doxorubicin-Induced Cardiotoxicity Through Gut Microbiota Modulation and Colonic Macrophage Polarization in Mice. Front Pharmacol. 2019 Feb 15;10:107. doi: 10.3389/fphar.2019.00107. PMID: 30833897; PMCID: PMC6387923.
In vitro protocol: 1. Aung KH, Liu H, Ke Z, Jiang S, Huang J. Glabridin Attenuates the Retinal Degeneration Induced by Sodium Iodate In Vitro and In Vivo. Front Pharmacol. 2020 Oct 15;11:566699. doi: 10.3389/fphar.2020.566699. PMID: 33178017; PMCID: PMC7593553. 2. Heo JS, Lee SG, Kim HO. The Flavonoid Glabridin Induces OCT4 to Enhance Osteogenetic Potential in Mesenchymal Stem Cells. Stem Cells Int. 2017;2017:6921703. doi: 10.1155/2017/6921703. Epub 2017 Nov 14. PMID: 29348759; PMCID: PMC5733956.
In vivo protocol: 1. Parlar A, Arslan SO, Çam SA. Glabridin Alleviates Inflammation and Nociception in Rodents by Activating BKCa Channels and Reducing NO Levels. Biol Pharm Bull. 2020 May 1;43(5):884-897. doi: 10.1248/bpb.b20-00038. Epub 2020 Mar 6. PMID: 32147624. 2. Huang K, Liu Y, Tang H, Qiu M, Li C, Duan C, Wang C, Yang J, Zhou X. Glabridin Prevents Doxorubicin-Induced Cardiotoxicity Through Gut Microbiota Modulation and Colonic Macrophage Polarization in Mice. Front Pharmacol. 2019 Feb 15;10:107. doi: 10.3389/fphar.2019.00107. PMID: 30833897; PMCID: PMC6387923.

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1: Simmler C, Pauli GF, Chen SN. Phytochemistry and biological properties of glabridin. Fitoterapia. 2013 Oct;90:160-84. doi: 10.1016/j.fitote.2013.07.003. Epub 2013 Jul 10. Review. PubMed PMID: 23850540; PubMed Central PMCID: PMC3795865.

2: Kang MR, Park KH, Oh SJ, Yun J, Lee CW, Lee MY, Han SB, Kang JS. Cardiovascular protective effect of glabridin: Implications in LDL oxidation and inflammation. Int Immunopharmacol. 2015 Dec;29(2):914-8. doi: 10.1016/j.intimp.2015.10.020. Epub 2015 Oct 29. Review. PubMed PMID: 26526087.

3: Singh V, Pal A, Darokar MP. A polyphenolic flavonoid glabridin: Oxidative stress response in multidrug-resistant Staphylococcus aureus. Free Radic Biol Med. 2015 Oct;87:48-57. doi: 10.1016/j.freeradbiomed.2015.06.016. Epub 2015 Jun 25. PubMed PMID: 26117328.

4: Su Wei Poh M, Voon Chen Yong P, Viseswaran N, Chia YY. Estrogenicity of glabridin in Ishikawa cells. PLoS One. 2015 Mar 27;10(3):e0121382. doi: 10.1371/journal.pone.0121382. eCollection 2015. Erratum in: PLoS One. 2015;10(7):e0133340. PubMed PMID: 25816349; PubMed Central PMCID: PMC4376725.

5: Sawada K, Yamashita Y, Zhang T, Nakagawa K, Ashida H. Glabridin induces glucose uptake via the AMP-activated protein kinase pathway in muscle cells. Mol Cell Endocrinol. 2014 Aug 5;393(1-2):99-108. doi: 10.1016/j.mce.2014.06.009. Epub 2014 Jun 19. PubMed PMID: 24953974.

6: Cheema HS, Prakash O, Pal A, Khan F, Bawankule DU, Darokar MP. Glabridin induces oxidative stress mediated apoptosis like cell death of malaria parasite Plasmodium falciparum. Parasitol Int. 2014 Apr;63(2):349-58. doi: 10.1016/j.parint.2013.12.005. Epub 2013 Dec 18. PubMed PMID: 24361284.

7: Huang HL, Hsieh MJ, Chien MH, Chen HY, Yang SF, Hsiao PC. Glabridin mediate caspases activation and induces apoptosis through JNK1/2 and p38 MAPK pathway in human promyelocytic leukemia cells. PLoS One. 2014 Jun 5;9(6):e98943. doi: 10.1371/journal.pone.0098943. eCollection 2014. PubMed PMID: 24901249; PubMed Central PMCID: PMC4047044.

8: Yehuda I, Madar Z, Leikin-Frenkel A, Tamir S. Glabridin, an isoflavan from licorice root, downregulates iNOS expression and activity under high-glucose stress and inflammation. Mol Nutr Food Res. 2015 Jun;59(6):1041-52. doi: 10.1002/mnfr.201400876. Epub 2015 May 3. PubMed PMID: 25737160.

9: Hsieh MJ, Lin CW, Yang SF, Chen MK, Chiou HL. Glabridin inhibits migration and invasion by transcriptional inhibition of matrix metalloproteinase 9 through modulation of NF-κB and AP-1 activity in human liver cancer cells. Br J Pharmacol. 2014 Jun;171(12):3037-50. doi: 10.1111/bph.12626. PubMed PMID: 24641665; PubMed Central PMCID: PMC4055204.

10: Hsieh MJ, Chen MK, Chen CJ, Hsieh MC, Lo YS, Chuang YC, Chiou HL, Yang SF. Glabridin induces apoptosis and autophagy through JNK1/2 pathway in human hepatoma cells. Phytomedicine. 2016 Apr 15;23(4):359-66. doi: 10.1016/j.phymed.2016.01.005. Epub 2016 Feb 13. PubMed PMID: 27002406.

11: Chen J, Yu X, Huang Y. Inhibitory mechanisms of glabridin on tyrosinase. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Nov 5;168:111-7. doi: 10.1016/j.saa.2016.06.008. Epub 2016 Jun 5. PubMed PMID: 27288962.

12: Wang WP, Hul J, Sui H, Zhao YS, Feng J, Liu C. Glabridin nanosuspension for enhanced skin penetration: formulation optimization, in vitro and in vivo evaluation. Pharmazie. 2016 May;71(5):252-7. PubMed PMID: 27348968.

13: Wu F, Jin Z, Jin J. Hypoglycemic effects of glabridin, a polyphenolic flavonoid from licorice, in an animal model of diabetes mellitus. Mol Med Rep. 2013 Apr;7(4):1278-82. doi: 10.3892/mmr.2013.1330. Epub 2013 Feb 19. PubMed PMID: 23426874.

14: Wang Z, Luo S, Wan Z, Chen C, Zhang X, Li B, Huang G, Chen L, He Z, Huang Z. Glabridin arrests cell cycle and inhibits proliferation of hepatocellular carcinoma by suppressing braf/MEK signaling pathway. Tumour Biol. 2016 May;37(5):5837-46. doi: 10.1007/s13277-015-4177-5. Epub 2015 Nov 19. PubMed PMID: 26586395.

15: Jin Z, Kim S, Cho S, Kim IH, Han D, Jin YH. Potentiating effect of glabridin on GABAA receptor-mediated responses in dorsal raphe neurons. Planta Med. 2013 Oct;79(15):1408-12. doi: 10.1055/s-0033-1350698. Epub 2013 Aug 23. PubMed PMID: 23975867.

16: Chanda D, Prieto-Lloret J, Singh A, Iqbal H, Yadav P, Snetkov V, Aaronson PI. Glabridin-induced vasorelaxation: Evidence for a role of BK(Ca) channels and cyclic GMP. Life Sci. 2016 Nov 15;165:26-34. doi: 10.1016/j.lfs.2016.09.018. Epub 2016 Sep 26. PubMed PMID: 27686831; PubMed Central PMCID: PMC5101995.

17: Kim HS, Suh KS, Ko A, Sul D, Choi D, Lee SK, Jung WW. The flavonoid glabridin attenuates 2-deoxy-D-ribose-induced oxidative damage and cellular dysfunction in MC3T3-E1 osteoblastic cells. Int J Mol Med. 2013 Jan;31(1):243-51. doi: 10.3892/ijmm.2012.1172. Epub 2012 Nov 2. PubMed PMID: 23128413.

18: Jen SH, Wei MP, Yin AC. The Combinatory Effects of Glabridin and Tamoxifen on Ishikawa and MCF-7 Cell Lines. Nat Prod Commun. 2015 Sep;10(9):1573-6. PubMed PMID: 26594762.

19: Choi EM, Suh KS, Kim YJ, Hong SM, Park SY, Chon S. Glabridin Alleviates the Toxic Effects of Methylglyoxal on Osteoblastic MC3T3-E1 Cells by Increasing Expression of the Glyoxalase System and Nrf2/HO-1 Signaling and Protecting Mitochondrial Function. J Agric Food Chem. 2016 Jan 13;64(1):226-35. doi: 10.1021/acs.jafc.5b05157. Epub 2016 Jan 5. PubMed PMID: 26670935.

20: Yehuda I, Madar Z, Leikin-Frenkel A, Szuchman-Sapir A, Magzal F, Markman G, Tamir S. Glabridin, an isoflavan from licorice root, upregulates paraoxonase 2 expression under hyperglycemia and protects it from oxidation. Mol Nutr Food Res. 2016 Feb;60(2):287-99. doi: 10.1002/mnfr.201500441. Epub 2015 Oct 29. PubMed PMID: 26455358.