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MedKoo Cat#: 463887 | Name: Luteolin 7-O-Glucuronide
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Description:

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

Luteolin 7-O-glucuronide is a flavonoid that has been found in S. chloroleuca and A. pilosa, and has diverse biological activities, including antioxidant, enzyme inhibitory, and anti-inflammatory properties. It scavenges DPPH radicals in a cell-free assay. Luteolin 7-O-Glucuronide inhibits porcine α-amylase and yeast α-glucosidase in vitro. It also inhibits rat aldose reductase in vitro and sorbitol accumulation in isolated rat lens by 91.8% when used at a concentration of 5 μg/ml. Luteolin 7-O-glucuronide inhibits LPS-induced cytokine release from RAW 264.7 macrophages in a dose-dependent manner.

Chemical Structure

Luteolin 7-O-Glucuronide
Luteolin 7-O-Glucuronide
CAS#29741-10-4

Theoretical Analysis

MedKoo Cat#: 463887

Name: Luteolin 7-O-Glucuronide

CAS#: 29741-10-4

Chemical Formula: C21H18O12

Exact Mass: 462.0798

Molecular Weight: 462.36

Elemental Analysis: C, 54.55; H, 3.92; O, 41.52

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 610.00 2 Weeks
25mg USD 950.00 2 Weeks
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Synonym
Luteolin 7-O-Glucuronide; Luteolin 7 O Glucuronide; Luteolin 7-O Glucuronide; Luteolin 7 O-Glucuronide; Luteolin-7-O-β-D-glucuronide; Luteolin 7 O β D-glucuronide;
IUPAC/Chemical Name
(2S,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
InChi Key
VSUOKLTVXQRUSG-ZFORQUDYSA-N
InChi Code
InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
SMILES Code
O=C1C2=C(C=C(C=C2OC(C3=CC(O)=C(O)C=C3)=C1)O[C@@H]4O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]4O)O
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:
Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.
In vitro activity:
Apigenin and luteolin are inactive on MMP-1, -3, and -8, which can be interpreted as a better selectivity for both -9 and -13 peptidases. The more active compounds are apigenin-7-O-rutinoside on MMP-1 and luteolin-7-O-rutinoside on MMP-3. Reference: Planta Med. 2017 Jul;83(11):901-911. https://pubmed.ncbi.nlm.nih.gov/28288492/
In vivo activity:
The present study aims to explore the antidepressant the effect of L7Gn (Luteolin 7-O-glucuronide) on stress-induced behaviors and the underlying mechanism in a mouse sleep deprivation (SD) model. L7Gn treatment improved depression-like and stress coping behaviors induced by SD stress, as confirmed by the tail suspension test and forced swimming test. Reference: Nutrients. 2022 Aug 12;14(16):3314. https://pubmed.ncbi.nlm.nih.gov/36014820/
Solvent mg/mL mM
Solubility
DMSO 108.5 234.66
Ethanol 10.0 21.63
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 462.36 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. Cho YC, Park J, Cho S. Anti-Inflammatory and Anti-Oxidative Effects of luteolin-7-O-glucuronide in LPS-Stimulated Murine Macrophages through TAK1 Inhibition and Nrf2 Activation. Int J Mol Sci. 2020 Mar 16;21(6):2007. doi: 10.3390/ijms21062007. PMID: 32187984; PMCID: PMC7139836. 2. Crascì L, Basile L, Panico A, Puglia C, Bonina FP, Basile PM, Rizza L, Guccione S. Correlating In Vitro Target-Oriented Screening and Docking: Inhibition of Matrix Metalloproteinases Activities by Flavonoids. Planta Med. 2017 Jul;83(11):901-911. doi: 10.1055/s-0043-104775. Epub 2017 Mar 13. PMID: 28288492. 3. Ryu D, Jee HJ, Kim SY, Hwang SH, Pil GB, Jung YS. Luteolin-7-O-Glucuronide Improves Depression-like and Stress Coping Behaviors in Sleep Deprivation Stress Model by Activation of the BDNF Signaling. Nutrients. 2022 Aug 12;14(16):3314. doi: 10.3390/nu14163314. PMID: 36014820; PMCID: PMC9412559.
In vitro protocol:
1. Cho YC, Park J, Cho S. Anti-Inflammatory and Anti-Oxidative Effects of luteolin-7-O-glucuronide in LPS-Stimulated Murine Macrophages through TAK1 Inhibition and Nrf2 Activation. Int J Mol Sci. 2020 Mar 16;21(6):2007. doi: 10.3390/ijms21062007. PMID: 32187984; PMCID: PMC7139836. 2. Crascì L, Basile L, Panico A, Puglia C, Bonina FP, Basile PM, Rizza L, Guccione S. Correlating In Vitro Target-Oriented Screening and Docking: Inhibition of Matrix Metalloproteinases Activities by Flavonoids. Planta Med. 2017 Jul;83(11):901-911. doi: 10.1055/s-0043-104775. Epub 2017 Mar 13. PMID: 28288492.
In vivo protocol:
1. Ryu D, Jee HJ, Kim SY, Hwang SH, Pil GB, Jung YS. Luteolin-7-O-Glucuronide Improves Depression-like and Stress Coping Behaviors in Sleep Deprivation Stress Model by Activation of the BDNF Signaling. Nutrients. 2022 Aug 12;14(16):3314. doi: 10.3390/nu14163314. PMID: 36014820; PMCID: PMC9412559.
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PMID: 32904463; PMCID: PMC7456477. 4: Fan LL, Zhang SS, Yao MX, Jiang Y, Su M, Wang XL, Hong Y, Han YQ. [Changes in chemical compositions of Chrysanthemi Flos after frying and protective effects on CCl_4-induced acute liver injury in mice]. Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(13):3144-3154. Chinese. doi: 10.19540/j.cnki.cjcmm.20200424.303. PMID: 32726023. 5: Wang X, Li Y, Chen M, Li C, Huang W, Gu K, Yu H, Yuan Y, Wang Y, Yang B, Li Y. Stepwise rapid tracking strategy to identify active molecules from Ixeris sonchifolia Hance based on "'affinity mass spectrometry-atomic force microscopy imaging'" technology. Talanta. 2020 Sep 1;217:121031. doi: 10.1016/j.talanta.2020.121031. Epub 2020 Apr 15. PMID: 32498901. 6: Trajčíková E, Kurin E, Slobodníková L, Straka M, Lichváriková A, Dokupilová S, Čičová I, Nagy M, Mučaji P, Bittner Fialová S. Antimicrobial and Antioxidant Properties of Four Lycopus Taxa and an Interaction Study of Their Major Compounds. Molecules. 2020 Mar 20;25(6):1422. doi: 10.3390/molecules25061422. PMID: 32245012; PMCID: PMC7144923. 7: Cho YC, Park J, Cho S. Anti-Inflammatory and Anti-Oxidative Effects of luteolin-7-O-glucuronide in LPS-Stimulated Murine Macrophages through TAK1 Inhibition and Nrf2 Activation. Int J Mol Sci. 2020 Mar 16;21(6):2007. doi: 10.3390/ijms21062007. PMID: 32187984; PMCID: PMC7139836. 8: Zhi H, Yuan Y, Zhang C, Jiang Y, Zhang H, Wang C, Ruan J. Importance of OATP1B1 and 1B3 in the Liver Uptake of Luteolin and Its Consequent Glucuronidation Metabolites. J Agric Food Chem. 2020 Feb 19;68(7):2063-2070. doi: 10.1021/acs.jafc.9b06954. Epub 2020 Feb 11. PMID: 32009392. 9: Shrestha SS, Sut S, Barbon Di Marco S, Zengin G, Gandin V, De Franco M, Pant DR, Mahomoodally MF, Dall'Acqua S, Rajbhandary S. Phytochemical Fingerprinting and In Vitro Bioassays of the Ethnomedicinal Fern Tectaria coadunata (J. Smith) C. Christensen from Central Nepal. Molecules. 2019 Dec 5;24(24):4457. doi: 10.3390/molecules24244457. PMID: 31817382; PMCID: PMC6943667. 10: Gibitz-Eisath N, Eichberger M, Gruber R, Seger C, Sturm S, Stuppner H. Towards eco-friendly secondary plant metabolite quantitation: Ultra high performance supercritical fluid chromatography applied to common vervain (Verbena officinalis L.). J Sep Sci. 2020 Feb;43(4):829-838. doi: 10.1002/jssc.201900854. Epub 2019 Dec 17. PMID: 31769179; PMCID: PMC7160600. 11: Zhu J, Yang Y, Duan S, Sun D. The Antialgal Mechanism of Luteolin-7-O-Glucuronide on Phaeocystis globosa by Metabolomics Analysis. Int J Environ Res Public Health. 2019 Sep 3;16(17):3222. doi: 10.3390/ijerph16173222. PMID: 31484378; PMCID: PMC6747131. 12: Zhu J, Xiao H, Chen Q, Zhao M, Sun D, Duan S. Growth Inhibition of Phaeocystis Globosa Induced by Luteolin-7-O-glucuronide from Seagrass Enhalus acoroides. Int J Environ Res Public Health. 2019 Jul 23;16(14):2615. doi: 10.3390/ijerph16142615. PMID: 31340457; PMCID: PMC6678453. 13: Zhang N, He Z, He S, Jing P. Insights into the importance of dietary chrysanthemum flower (Chrysanthemum morifolium cv. Hangju)-wolfberry (Lycium barbarum fruit) combination in antioxidant and anti-inflammatory properties. Food Res Int. 2019 Feb;116:810-818. doi: 10.1016/j.foodres.2018.09.015. Epub 2018 Sep 10. PMID: 30717012. 14: Tardugno R, Pozzebon M, Beggio M, Del Turco P, Pojana G. Polyphenolic profile of Cichorium intybus L. endemic varieties from the Veneto region of Italy. Food Chem. 2018 Nov 15;266:175-182. doi: 10.1016/j.foodchem.2018.05.085. Epub 2018 May 26. PMID: 30381174. 15: Gomes AF, Almeida MP, Leite MF, Schwaiger S, Stuppner H, Halabalaki M, Amaral JG, David JM. Seasonal variation in the chemical composition of two chemotypes of Lippia alba. Food Chem. 2019 Feb 1;273:186-193. doi: 10.1016/j.foodchem.2017.11.089. Epub 2017 Nov 23. PMID: 30292367. 16: Gonçalves GA, Corrêa RCG, Barros L, Dias MI, Calhelha RC, Correa VG, Bracht A, Peralta RM, Ferreira ICFR. Effects of in vitro gastrointestinal digestion and colonic fermentation on a rosemary (Rosmarinus officinalis L) extract rich in rosmarinic acid. Food Chem. 2019 Jan 15;271:393-400. doi: 10.1016/j.foodchem.2018.07.132. Epub 2018 Jul 19. PMID: 30236693. 17: Shi F, Pan H, Lu Y, Ding L. An HPLC-MS/MS method for the simultaneous determination of luteolin and its major metabolites in rat plasma and its application to a pharmacokinetic study. J Sep Sci. 2018 Oct;41(20):3830-3839. doi: 10.1002/jssc.201800585. Epub 2018 Aug 26. PMID: 30101558. 18: Lin Y, Lv Y, Fu J, Jia Q, Han S. A high expression Mas-related G protein coupled receptor X2 cell membrane chromatography coupled with liquid chromatography and mass spectrometry method for screening potential anaphylactoid components in kudiezi injection. 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