Liquiritoside | CAS#551-15-5 | flavonoid complex

MedKoo Cat#: 598863 | Name: Liquiritoside

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Description:

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

Liquiritoside is a flavonoid complex isoalted from Glycyrrhizae radix.

Chemical Structure

Liquiritoside

CAS#551-15-5

Theoretical Analysis

MedKoo Cat#: 598863

Name: Liquiritoside

CAS#: 551-15-5

Chemical Formula: C21H22O9

Exact Mass: 418.1264

Molecular Weight: 418.40

Elemental Analysis: C, 60.28; H, 5.30; O, 34.41

Price and Availability

Size	Price	Availability
10mg	USD 320.00
25mg	USD 585.00	2 Weeks
50g	USD 950.00	2 Weeks

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Synonym

Liquiritoside; Likviritin; Liquiritin;

IUPAC/Chemical Name

(S)-7-hydroxy-2-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-4-one

InChi Key

DEMKZLAVQYISIA-ZRWXNEIDSA-N

InChi Code

InChI=1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1

SMILES Code

O=C1C[C@@H](C2=CC=C(O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C=C2)OC4=CC(O)=CC=C14

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Liquiritin is a potent and competitive AKR1C1 inhibitor with IC50s of 0.62 μM, 0.61 μM, and 3.72μM for AKR1C1, AKR1C2 and AKR1C3, respectively.

In vitro activity:

Kinetic analyses in the S-(+)-1,2,3,4-tetrahydro-1-naphthol (s-tetralol) catalyzed by AKR1C1 in the presence of the inhibitors suggest that liquiritin is a competitive inhibitor by targeting the residues Ala-27, Val-29, Ala-25, and Asn-56 of AKR1C1. In HEC-1-B cells, treatment with liquiritin results in 85.00% of reduction in progesterone metabolism, which is mediated by AKR1C1 enzymatic activity. Reference: Front Physiol. 2019 Jul 3;10:833. https://pubmed.ncbi.nlm.nih.gov/31333491/

In vivo activity:

This study aimed to investigate the protective efficacy of liquiritin on chronic constriction injury (CCI)-induced neuropathic pain in mice. Results showed that liquiritin dose-dependently reduced hyperalgesia and allodynia and increased the sciatic functional index and motor nerve conduction velocities. Moreover, liquiritin restored the injured axon and myelin sheath, inhibited the activation of astrocyte and microglia, down-regulated the pro-inflammatory cytokines including tumor necrosis factor alpha (TNF-α), interleukin (IL-6, and IL-1β), and simultaneously up-regulated the anti-inflammatory cytokine IL-10. Reference: Biomed Pharmacother. 2017 Nov;95:186-198. https://pubmed.ncbi.nlm.nih.gov/28843150/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	71.70
	DMF:PBS (pH 7.2) (1:20)	0.0	0.10
	DMSO	90.0	215.11

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 418.40 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. Zeng C, Zhu D, You J, Dong X, Yang B, Zhu H, He Q. Liquiritin, as a Natural Inhibitor of AKR1C1, Could Interfere With the Progesterone Metabolism. Front Physiol. 2019 Jul 3;10:833. doi: 10.3389/fphys.2019.00833. PMID: 31333491; PMCID: PMC6616128. 2. Nakatani Y, Kobe A, Kuriya M, Hiroki Y, Yahagi T, Sakakibara I, Matsuzaki K, Amano T. Neuroprotective effect of liquiritin as an antioxidant via an increase in glucose-6-phosphate dehydrogenase expression on B65 neuroblastoma cells. Eur J Pharmacol. 2017 Nov 15;815:381-390. doi: 10.1016/j.ejphar.2017.09.040. Epub 2017 Sep 29. PMID: 28970010. 3. Zhang MT, Wang B, Jia YN, Liu N, Ma PS, Gong SS, Niu Y, Sun T, Li YX, Yu JQ. Neuroprotective effect of liquiritin against neuropathic pain induced by chronic constriction injury of the sciatic nerve in mice. Biomed Pharmacother. 2017 Nov;95:186-198. doi: 10.1016/j.biopha.2017.07.167. Epub 2017 Sep 12. PMID: 28843150. 4. He SH, Liu HG, Zhou YF, Yue QF. Liquiritin (LT) exhibits suppressive effects against the growth of human cervical cancer cells through activating Caspase-3 in vitro and xenograft mice in vivo. Biomed Pharmacother. 2017 Aug;92:215-228. doi: 10.1016/j.biopha.2017.05.026. Epub 2017 May 22. PMID: 28544935.

In vitro protocol:

In vivo protocol:

1. Zhang MT, Wang B, Jia YN, Liu N, Ma PS, Gong SS, Niu Y, Sun T, Li YX, Yu JQ. Neuroprotective effect of liquiritin against neuropathic pain induced by chronic constriction injury of the sciatic nerve in mice. Biomed Pharmacother. 2017 Nov;95:186-198. doi: 10.1016/j.biopha.2017.07.167. Epub 2017 Sep 12. PMID: 28843150. 2. He SH, Liu HG, Zhou YF, Yue QF. Liquiritin (LT) exhibits suppressive effects against the growth of human cervical cancer cells through activating Caspase-3 in vitro and xenograft mice in vivo. Biomed Pharmacother. 2017 Aug;92:215-228. doi: 10.1016/j.biopha.2017.05.026. Epub 2017 May 22. PMID: 28544935.

1: Yu JY, Ha JY, Kim KM, Jung YS, Jung JC, Oh S. Anti-Inflammatory activities of licorice extract and its active compounds, glycyrrhizic acid, liquiritin and liquiritigenin, in BV2 cells and mice liver. Molecules. 2015 Jul 20;20(7):13041-54. doi: 10.3390/molecules200713041. PubMed PMID: 26205049. 2: Xiang Y, Liu CS, Liu Y, Song XN, Gu X. [Effects of abscisic acid on chemical components content and color of Glycyrrhiza uralensis]. Zhongguo Zhong Yao Za Zhi. 2015 May;40(9):1688-92. Chinese. PubMed PMID: 26323130. 3: Kong W, Zhao Y, Xing X, Ma X, Sun X, Yang M, Xiao X. Antibacterial evaluation of flavonoid compounds against E. coli by microcalorimetry and chemometrics. Appl Microbiol Biotechnol. 2015 Jul;99(14):6049-58. doi: 10.1007/s00253-015-6711-1. Epub 2015 Jun 9. PubMed PMID: 26051672. 4: Nan XM, Gu J, Tan R, Ren Y, Wang S. [Simultaneous Determination of Index Components in Wuwei Shaji Oral Liquid by HPLC]. Zhong Yao Cai. 2015 Mar;38(3):615-7. Chinese. PubMed PMID: 26495666. 5: Hou J, Yan LB, Zhao GL, Du T, Shao SJ. [Relationship Between Seedling Grade of Glycyrrhiza uralensis and Plant Biomass Accumulation, Yield and Quality of Product]. Zhong Yao Cai. 2015 Feb;38(2):221-6. Chinese. PubMed PMID: 26415393. 6: Gao Y, Gao L, Gao XX, Zhou YZ, Qin XM, Tian JS. [An exploration in the action targets for antidepressant bioactive components of Xiaoyaosan based on network pharmacology]. Yao Xue Xue Bao. 2015 Dec;50(12):1589-95. Chinese. PubMed PMID: 27169281. 7: Zhang Y, Zhang L, Zhang Y, Xu JJ, Sun LL, Li SZ. The protective role of liquiritin in high fructose-induced myocardial fibrosis via inhibiting NF-κB and MAPK signaling pathway. Biomed Pharmacother. 2016 Dec;84:1337-1349. doi: 10.1016/j.biopha.2016.10.036. Epub 2016 Nov 1. PubMed PMID: 27810791. 8: Jia SL, Wu XL, Li XX, Dai XL, Gao ZL, Lu Z, Zheng QS, Sun YX. Neuroprotective effects of liquiritin on cognitive deficits induced by soluble amyloid-β(1-42) oligomers injected into the hippocampus. J Asian Nat Prod Res. 2016 Dec;18(12):1186-1199. Epub 2016 Sep 2. PubMed PMID: 27589374. 9: Qiao J, Hu J, Li YP, Ren GX, Xiang Y, Zang YM, Liu Y, Liu CS. [Effect of exogenous brassinolide on morphological characters and contents of seven chemical constituents of Glycyrrhiza uralensis]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(2):197-204. doi: 10.4268/cjcmm20160208. Chinese. PubMed PMID: 28861963. 10: Fujii S, Morinaga O, Uto T, Nomura S, Shoyama Y. Development of Double Eastern Blotting for Major Licorice Components, Glycyrrhizin and Liquiritin for Chemical Quality Control of Licorice Using anti-Glycyrrhizin and anti-Liquiritin Monoclonal Antibodies. J Agric Food Chem. 2016 Feb 10;64(5):1087-93. doi: 10.1021/acs.jafc.5b04732. Epub 2016 Jan 27. PubMed PMID: 26765784. 11: Zhan XY, Lin ZZ, Sun Y, Yuan RJ, Yang ZL, Duan TX. [Feature Selection and Interpretation in Infrared Quantitative Models of Liquiritin and Glycyrrhizin in Radix Glycyrrhizae]. Guang Pu Xue Yu Guang Pu Fen Xi. 2015 Sep;35(9):2530-5. Chinese. PubMed PMID: 26669161. 12: Luo Y, Zhao GW, Liang XL, Zhang J, Zhang XF, Zheng Q, Yang M, Liao ZG. [Changes of specific chromatograms and contents of five components in Yinqiao powder decoctions during decocting process]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(1):60-64. doi: 10.4268/cjcmm20160112. Chinese. PubMed PMID: 28845641. 13: Seo CS, Shin HK. HPLC-PDA Method for Simultaneous Determination of Nine Marker Components in Banhasasim-Tang. J Chromatogr Sci. 2016 Mar;54(3):299-304. doi: 10.1093/chromsci/bmv141. Epub 2015 Sep 8. PubMed PMID: 26354947. 14: Gong H, Zhang BK, Yan M, Fang PF, Li HD, Hu CP, Yang Y, Cao P, Jiang P, Fan XR. A protective mechanism of licorice (Glycyrrhiza uralensis): isoliquiritigenin stimulates detoxification system via Nrf2 activation. J Ethnopharmacol. 2015 Mar 13;162:134-9. doi: 10.1016/j.jep.2014.12.043. Epub 2014 Dec 31. PubMed PMID: 25557030. 15: Guo ZZ, Wu YL, Wang RF, Wang WQ, Liu Y, Zhang XQ, Gao SR, Zhang Y, Wei SL. Distribution patterns of the contents of five active components in taproot and stolon of Glycyrrhiza uralensis. Biol Pharm Bull. 2014;37(7):1253-8. Epub 2014 May 3. PubMed PMID: 24805208. 16: Huang X, Wang Y, Ren K. Protective Effects of Liquiritin on the Brain of Rats with Alzheimer's Disease. West Indian Med J. 2015 Dec;64(5):468-472. doi: 10.7727/wimj.2016.058. Epub 2016 Apr 29. PubMed PMID: 27399208; PubMed Central PMCID: PMC4961333. 17: Fujii S, Morinaga O, Uto T, Nomura S, Shoyama Y. Development of a monoclonal antibody-based immunochemical assay for liquiritin and its application to the quality control of licorice products. J Agric Food Chem. 2014 Apr 16;62(15):3377-83. doi: 10.1021/jf404731z. Epub 2014 Apr 3. PubMed PMID: 24621071. 18: Farahani MS, Bahramsoltani R, Farzaei MH, Abdollahi M, Rahimi R. Plant-derived natural medicines for the management of depression: an overview of mechanisms of action. Rev Neurosci. 2015;26(3):305-21. doi: 10.1515/revneuro-2014-0058. Review. PubMed PMID: 25719303. 19: Zhang Y, Qian D, Pan Y, Zhu Z, Huang J, Xi J, Guo J, Zhou X, Zhong G, Duan J. Comparisons of the pharmacokinetic profile of four bioactive components after oral administration of gan-sui-ban-xia decoction plus-minus gansui and gancao drug combination in normal rats. Molecules. 2015 May 20;20(5):9295-308. doi: 10.3390/molecules20059295. PubMed PMID: 26007184. 20: Zhang W, Di LQ, Li JS, Shan JJ, Kang A, Qian S, Chen LT. The effects of Glycyrrhizae uralenis and its major bioactive components on pharmacokinetics of daphnetin in Cortex daphnes in rats. J Ethnopharmacol. 2014 Jul 3;154(3):584-92. doi: 10.1016/j.jep.2014.03.047. Epub 2014 Apr 3. PubMed PMID: 24704595.