Glycyrrhizin | CAS#1405-86-3 | HMGB1 inhibitor

MedKoo Cat#: 461353 | Name: Glycyrrhizin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Glycyrrhizin is an inhibitor of HMGB1. It is a triterpene glycoside isolated from licorice root, is known to have anti-inflammatory activities

Chemical Structure

Glycyrrhizin

CAS#1405-86-3

Theoretical Analysis

MedKoo Cat#: 461353

Name: Glycyrrhizin

CAS#: 1405-86-3

Chemical Formula: C42H62O16

Exact Mass: 822.4038

Molecular Weight: 822.94

Elemental Analysis: C, 61.30; H, 7.59; O, 31.11

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 Weeks
25g	USD 650.00	2 Weeks

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Synonym

Glycyrrhizin; Glycyrrhizic acid; Glycyron; Glycyrrhizinic acid; Glizigen; Glycyrrhetinic acid glycoside

IUPAC/Chemical Name

(2S,3S,4S,5R,6R)-6-(((2S,3R,4S,5S,6S)-6-carboxy-2-(((3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

InChi Key

LPLVUJXQOOQHMX-QWBHMCJMSA-N

InChi Code

InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1

SMILES Code

C[C@]12[C@@](C(C=C3[C@]2(CC[C@]4(C)[C@@]3([H])C[C@](C(O)=O)(C)CC4)C)=O)([H])[C@@]5([C@@](C(C)([C@@H](O[C@]6([H])[C@@H]([C@H]([C@H](O)[C@@H](C(O)=O)O6)O)O[C@]7([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)CC5)C)([H])CC1)C

Appearance

Solid powder

Purity

>85% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Glycyrrhizic acid is a triterpenoid saponinl, acting as a direct HMGB1 antagonist, with anti-tumor, anti-diabetic activities.

In vitro activity:

As depicted in Fig. 1A the viability of CaSki cervical cancer cells was reduced significantly in a dose- and time-related manner after treatment with increasing concentrations of Gly (glycyrrhizin) (20, 40, 80, 160 and 320 μM) for 24 and 48 h. Reference: Saudi J Biol Sci. 2022 May;29(5):3264-3275. https://pubmed.ncbi.nlm.nih.gov/35844403/

In vivo activity:

To further test the role of GL (glycyrrhizin) in HIBD (hypoxic-ischemic brain damage), the relevant inflammatory factors TNF-α, IL-6, and IL-1β were detected by qRT–PCR. The results indicated that the levels of TNF-α, IL-6, and IL-1β were significantly increased at 72 h following HIBD in the injured cortex, which was obviously suppressed by GL treatment (Figures 4(a)–4(c)). Furthermore, the immunofluorescence of the IL-1β expression in injured cortical neurons further suggested that there was a significant decrease in the expression of IL-1β in the HI + GL group compared with the HI group (Figure 4(d)). Reference: Oxid Med Cell Longev. 2022 Apr 7;2022:8438528. https://pubmed.ncbi.nlm.nih.gov/35432719/

	Solvent	mg/mL	mM
Solubility
	DMSO	300.0	364.55
	Ethanol	100.0	121.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 822.94 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.

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. Ahmad A, Tiwari RK, Mishra P, Alkhathami AG, Almeleebia TM, Alshahrani MY, Ahmad I, Asiri RA, Alabdullah NM, Hussien M, Saeed M, Ansari IA. Antiproliferative and apoptotic potential of Glycyrrhizin against HPV16+ Caski cervical cancer cells: A plausible association with downreguation of HPV E6 and E7 oncogenes and Notch signaling pathway. Saudi J Biol Sci. 2022 May;29(5):3264-3275. doi: 10.1016/j.sjbs.2022.01.054. Epub 2022 Jan 31. PMID: 35844403; PMCID: PMC9280173. 2. Wang P, Hao P, Chen X, Li L, Zhou Y, Zhang X, Zhu L, Ying M, Han R, Wang L, Li X. Targeting HMGB1-NFκb Axis and miR-21 by Glycyrrhizin: Role in Amelioration of Corneal Injury in a Mouse Model of Alkali Burn. Front Pharmacol. 2022 May 2;13:841267. doi: 10.3389/fphar.2022.841267. PMID: 35586052; PMCID: PMC9108160. 3. Zhu K, Zhu X, Liu S, Yu J, Wu S, Hei M. Glycyrrhizin Attenuates Hypoxic-Ischemic Brain Damage by Inhibiting Ferroptosis and Neuroinflammation in Neonatal Rats via the HMGB1/GPX4 Pathway. Oxid Med Cell Longev. 2022 Apr 7;2022:8438528. doi: 10.1155/2022/8438528. PMID: 35432719; PMCID: PMC9010207. 4. Hu Z, Xiao M, Cai H, Li W, Fang W, Long X. Glycyrrhizin regulates rat TMJOA progression by inhibiting the HMGB1-RAGE/TLR4-NF-κB/AKT pathway. J Cell Mol Med. 2022 Feb;26(3):925-936. doi: 10.1111/jcmm.17149. Epub 2021 Dec 24. PMID: 34953035; PMCID: PMC8817133.

In vitro protocol:

In vivo protocol:

1. Zhu K, Zhu X, Liu S, Yu J, Wu S, Hei M. Glycyrrhizin Attenuates Hypoxic-Ischemic Brain Damage by Inhibiting Ferroptosis and Neuroinflammation in Neonatal Rats via the HMGB1/GPX4 Pathway. Oxid Med Cell Longev. 2022 Apr 7;2022:8438528. doi: 10.1155/2022/8438528. PMID: 35432719; PMCID: PMC9010207. 2. Hu Z, Xiao M, Cai H, Li W, Fang W, Long X. Glycyrrhizin regulates rat TMJOA progression by inhibiting the HMGB1-RAGE/TLR4-NF-κB/AKT pathway. J Cell Mol Med. 2022 Feb;26(3):925-936. doi: 10.1111/jcmm.17149. Epub 2021 Dec 24. PMID: 34953035; PMCID: PMC8817133.

1: Kim YM, Kim HJ, Chang KC. Glycyrrhizin reduces HMGB1 secretion in lipopolysaccharide-activated RAW 264.7 cells and endotoxemic mice by p38/Nrf2-dependent induction of HO-1. Int Immunopharmacol. 2015 May;26(1):112-8. doi: 10.1016/j.intimp.2015.03.014. Epub 2015 Mar 24. PubMed PMID: 25812767. 2: Fu Y, Zhou E, Wei Z, Liang D, Wang W, Wang T, Guo M, Zhang N, Yang Z. Glycyrrhizin inhibits the inflammatory response in mouse mammary epithelial cells and a mouse mastitis model. FEBS J. 2014 Jun;281(11):2543-57. doi: 10.1111/febs.12801. Epub 2014 May 12. PubMed PMID: 24698106. 3: Feng X, Ding L, Qiu F. Potential drug interactions associated with glycyrrhizin and glycyrrhetinic acid. Drug Metab Rev. 2015 May;47(2):229-38. doi: 10.3109/03602532.2015.1029634. Epub 2015 Mar 31. Review. PubMed PMID: 25825801. 4: Yoshida S, Lee JO, Nakamura K, Suzuki S, Hendon DN, Kobayashi M, Suzuki F. Effect of glycyrrhizin on pseudomonal skin infections in human-mouse chimeras. PLoS One. 2014 Jan 30;9(1):e83747. doi: 10.1371/journal.pone.0083747. eCollection 2014. PubMed PMID: 24497916; PubMed Central PMCID: PMC3907411. 5: Siddiqui NA, Alam P, Parvez MK, Basudan OA, Al-Dosari MS, Al-Rehaily AJ, Al-Ajmi MF, Shakeel F. Quantification of glycyrrhizin in anti-stress herbal formulations by validate HPTLC method: a rational paradigm towards quality control of herbals. Pak J Pharm Sci. 2015 Jan;28(1 Suppl):353-7. PubMed PMID: 25631512. 6: Chang CZ, Wu SC, Kwan AL. Glycyrrhizin Attenuates Proinflammatory Cytokines through a Peroxisome Proliferator-Activated Receptor-γ-Dependent Mechanism and Experimental Vasospasm in a Rat Model. J Vasc Res. 2015;52(1):12-21. doi: 10.1159/000381099. Epub 2015 Apr 16. PubMed PMID: 25896311. 7: Xu R, Xiao Q, Cao Y, Yang J. Comparison of the exposure of glycyrrhizin and its metabolites and the pseudoaldosteronism after intravenous administration of alpha- and beta-glycyrrhizin in rat. Drug Res (Stuttg). 2013 Dec;63(12):620-4. doi: 10.1055/s-0033-1349837. Epub 2013 Jul 17. PubMed PMID: 23864391. 8: Basar N, Talukdar AD, Nahar L, Stafford A, Kushiev H, Kan A, Sarker SD. A simple semi-preparative reversed-phase HPLC/PDA method for separation and quantification of glycyrrhizin in nine samples of Glycyrrhiza glabra root collected from different geographical origins. Phytochem Anal. 2014 Sep-Oct;25(5):399-404. doi: 10.1002/pca.2507. Epub 2014 Mar 3. PubMed PMID: 24585378. 9: Yamamoto R, Takasuga S, Kominami K, Sutoh C, Kinoshita M, Kanamura K, Takayama K. Iontophoretic transdermal delivery of glycyrrhizin: effects of pH, drug concentration, co-ions, current intensity, and chemical enhancers. Chem Pharm Bull (Tokyo). 2013;61(12):1275-81. PubMed PMID: 24292789. 10: Xiong H, Xu Y, Tan G, Han Y, Tang Z, Xu W, Zeng F, Guo Q. Glycyrrhizin ameliorates imiquimod-induced psoriasis-like skin lesions in BALB/c mice and inhibits TNF-α-induced ICAM-1 expression via NF-κB/MAPK in HaCaT cells. Cell Physiol Biochem. 2015;35(4):1335-46. doi: 10.1159/000373955. Epub 2015 Feb 12. PubMed PMID: 25720416. 11: Tsai JJ, Kuo HC, Lee KF, Tsai TH. Glycyrrhizin represses total parenteral nutrition-associated acute liver injury in rats by suppressing endoplasmic reticulum stress. Int J Mol Sci. 2013 Jun 14;14(6):12563-80. doi: 10.3390/ijms140612563. PubMed PMID: 23771023; PubMed Central PMCID: PMC3709800. 12: Hayashi H, Fujii I, Iinuma M, Shibano M, Ozaki K, Watanabe H. Characterization of a glycyrrhizin-deficient strain of Glycyrrhiza uralensis. Biol Pharm Bull. 2013;36(9):1448-53. PubMed PMID: 23995656. 13: Barakat W, Safwet N, El-Maraghy NN, Zakaria MN. Candesartan and glycyrrhizin ameliorate ischemic brain damage through downregulation of the TLR signaling cascade. Eur J Pharmacol. 2014 Feb 5;724:43-50. doi: 10.1016/j.ejphar.2013.12.032. Epub 2013 Dec 27. PubMed PMID: 24378346. 14: Ren CA, Li YX, Cui JY, Sheng ZX, Ran XH, Wang BH, Zhang MH. Efficacy of glycyrrhizin combined with cyclosporine in the treatment of non-severe aplastic anemia. Chin Med J (Engl). 2013;126(11):2083-6. PubMed PMID: 23769562. 15: de Paula FT, Frauches PQ, Pedebos C, Berger M, Gnoatto SC, Gossmann G, Verli H, Guimarães JA, Graebin CS. Improving the thrombin inhibitory activity of glycyrrhizin, a triterpenic saponin, through a molecular simplification of the carbohydrate moiety. Chem Biol Drug Des. 2013 Dec;82(6):756-60. doi: 10.1111/cbdd.12204. Epub 2013 Oct 25. PubMed PMID: 23964664. 16: Gu XJ, Xu J, Ma BY, Chen G, Gu PY, Wei D, Hu WX. Effect of glycyrrhizin on traumatic brain injury in rats and its mechanism. Chin J Traumatol. 2014;17(1):1-7. PubMed PMID: 24506915. 17: Liu Z, Zhong JY, Gao EN, Yang H. [Effects of combination of glycyrrhizin acid, ligustrazine and puerarin on LPS-induced cytokines expression in macrophage]. Zhongguo Zhong Yao Za Zhi. 2015 Oct;40(20):4068-74. Chinese. PubMed PMID: 27062829. 18: Kurosaki T, Kawanabe S, Kodama Y, Fumoto S, Nishida K, Nakagawa H, Higuchi N, Nakamura T, Kitahara T, Sasaki H. Hepatic gene delivery system electrostatically assembled with glycyrrhizin. Mol Pharm. 2014 May 5;11(5):1369-77. doi: 10.1021/mp400398f. Epub 2014 Apr 21. PubMed PMID: 24673596. 19: Zhao YK, Li L, Liu X, Cheng SP, Guo QQ, Fan DP, Zheng K, He XJ, Lv AP. [Explore pharmacological mechanism of glycyrrhizin based on systems pharmacology]. Zhongguo Zhong Yao Za Zhi. 2016 May;41(10):1916-1920. doi: 10.4268/cjcmm20161026. Chinese. PubMed PMID: 28895343. 20: Sil R, Ray D, Chakraborti AS. Glycyrrhizin ameliorates insulin resistance, hyperglycemia, dyslipidemia and oxidative stress in fructose-induced metabolic syndrome-X in rat model. Indian J Exp Biol. 2013 Feb;51(2):129-38. PubMed PMID: 23923606.