Eupatorin | CAS# 855-96-9 | Flavonoid

MedKoo Cat#: 574691 | Name: Eupatorin

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Description:

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

Eupatorin is a flavonoid that inhibits the growth of HeLa, MK-1, and B16/F10 tumor cells. Eupatorin is active against T. cruzi epimastigotes and trypomastigotes without inducing cytotoxicity in Vero cells. It induces vasorelaxation in isolated rat thoracic aortic rings precontracted with phenylephrine (pD2 = 6.66). Eupatorin reduces nuclear translocation of NF-κB and STAT1α in J774 murine macrophages and reduces paw edema in a mouse model of carrageenan-induced paw inflammation..

Chemical Structure

Eupatorin

CAS#855-96-9

Theoretical Analysis

MedKoo Cat#: 574691

Name: Eupatorin

CAS#: 855-96-9

Chemical Formula: C18H16O7

Exact Mass: 344.0896

Molecular Weight: 344.32

Elemental Analysis: C, 62.79; H, 4.68; O, 32.53

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 600.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Synonym

Eupatorin; Eupatorine; NSC 106402; NSC106402; NSC-106402;

IUPAC/Chemical Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one

InChi Key

KLAOKWJLUQKWIF-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

SMILES Code

O=C1C2=C(O)C(OC)=C(OC)C=C2OC(C3=CC(O)=C(OC)C=C3)=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

>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

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Eupatorin arrests cells at the G2-M phase of the cell cycle and induces apoptotic cell death involving activation of multiple caspases, mitochondrial release of cytochrome c and poly(ADP-ribose) polymerase cleavage.

In vitro activity:

As shown in Fig. 3B, eupatorin (5 μg/mL) significantly (p < 0.05) decreased cell motility and migration of cancer cells where the complete closure of the scratched area was inhibited by 50.14% at 24 h. In addition, Transwell Boyden chamber assay showed that eupatorin prevented MDA-MB-231 cells from migrating aggressively through the filter (Fig. 3C,D). Only 38 ± 3% of MDA-MB-231 cells migrated through the membrane compared to the untreated group (Fig. 3E). In addition, Fig. 3F,G show that eupatorin significantly (p < 0.05) decreased the level of cell invasion through the Matrigel-coated membrane. Only 37 ± 3% of MDA-MB-231 cells had invaded the Matrigel-coated membrane in the Boyden chamber assay (Fig. 3H) at 24 h. Taken together, these results suggest that eupatorin has strong inhibitory effects on the migration and invasion of MDA-MB-231 cells. Reference: Sci Rep. 2019; 9: 1514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6365513/

In vivo activity:

The 4T1-induced mice treated with the high dosage of eupatorin at 20 mg/kg BW had the smallest tumor compared with the mice in the untreated group and low-dosage group. In addition, the group of mice fed with 5 mg/kg BW eupatorin did not show any significant reduction in the tumor weight (TW; 1.102 ± 0.033 g), while tumor mice treated with 20 g/kg BW had significantly lower (P < .05) TW (0.839 ± 0.104 g) as compared with the untreated, which demonstrated the TW of 1.110 ± 0.067 g (Figure 3A). This suggested that eupatorin at the dosage of 20 mg/kg BW is sufficient to reduce the tumor size in mice. Reference: Integr Cancer Ther. 2020; 19: 1534735420935625. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7448146/

	Solvent	mg/mL	mM
Solubility
	DMSO	130.0	377.56
	DMSO:PBS (pH 7.2) (1:9)	0.1	0.29
	DMF	10.0	29.04

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 344.32 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. Razak NA, Abu N, Ho WY, Zamberi NR, Tan SW, Alitheen NB, Long K, Yeap SK. Cytotoxicity of eupatorin in MCF-7 and MDA-MB-231 human breast cancer cells via cell cycle arrest, anti-angiogenesis and induction of apoptosis. Sci Rep. 2019 Feb 6;9(1):1514. doi: 10.1038/s41598-018-37796-w. PMID: 30728391; PMCID: PMC6365513. 2. Estévez S, Marrero MT, Quintana J, Estévez F. Eupatorin-induced cell death in human leukemia cells is dependent on caspases and activates the mitogen-activated protein kinase pathway. PLoS One. 2014 Nov 12;9(11):e112536. doi: 10.1371/journal.pone.0112536. PMID: 25390937; PMCID: PMC4229185. 3. Abd Razak N, Yeap SK, Alitheen NB, Ho WY, Yong CY, Tan SW, Tan WS, Long K. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integr Cancer Ther. 2020 Jan-Dec;19:1534735420935625. doi: 10.1177/1534735420935625. PMID: 32830560; PMCID: PMC7448146.

In vitro protocol:

In vivo protocol:

1. Abd Razak N, Yeap SK, Alitheen NB, Ho WY, Yong CY, Tan SW, Tan WS, Long K. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integr Cancer Ther. 2020 Jan-Dec;19:1534735420935625. doi: 10.1177/1534735420935625. PMID: 32830560; PMCID: PMC7448146.

1: Razak NA, Abu N, Ho WY, Zamberi NR, Tan SW, Alitheen NB, Long K, Yeap SK. Cytotoxicity of eupatorin in MCF-7 and MDA-MB-231 human breast cancer cells via cell cycle arrest, anti-angiogenesis and induction of apoptosis. Sci Rep. 2019 Feb 6;9(1):1514. doi: 10.1038/s41598-018-37796-w. PMID: 30728391; PMCID: PMC6365513. 2: González-Cortazar M, Salinas-Sánchez DO, Herrera-Ruiz M, Román-Ramos DC, Zamilpa A, Jiménez-Ferrer E, Ble-González EA, Álvarez-Fitz P, Castrejón-Salgado R, Pérez-García MD. Eupatorin and Salviandulin-A, with Antimicrobial and Anti- Inflammatory Effects from Salvia lavanduloides Kunth Leaves. Plants (Basel). 2022 Jun 30;11(13):1739. doi: 10.3390/plants11131739. PMID: 35807691; PMCID: PMC9269164. 3: Abd Razak N, Yeap SK, Alitheen NB, Ho WY, Yong CY, Tan SW, Tan WS, Long K. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integr Cancer Ther. 2020 Jan-Dec;19:1534735420935625. doi: 10.1177/1534735420935625. PMID: 32830560; PMCID: PMC7448146. 4: Ali Z, Radhakrishnan S, Avula B, Chittiboyina AG, Li J, Wu C, Khan IA. Eupatorin 3'-O-glucopyranoside, a trimethoxyflavonoid glucoside from the aerial parts of Salvia mellifera. Nat Prod Res. 2023 Jan;37(2):269-276. doi: 10.1080/14786419.2021.1969565. Epub 2021 Aug 26. PMID: 34435528. 5: Laavola M, Nieminen R, Yam MF, Sadikun A, Asmawi MZ, Basir R, Welling J, Vapaatalo H, Korhonen R, Moilanen E. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 2012 May;78(8):779-86. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. PMID: 22516932. 6: Li L, Chen Y, Feng X, Yin J, Li S, Sun Y, Zhang L. Identification of Metabolites of Eupatorin in Vivo and in Vitro Based on UHPLC-Q-TOF-MS/MS. Molecules. 2019 Jul 23;24(14):2658. doi: 10.3390/molecules24142658. PMID: 31340434; PMCID: PMC6680898. 7: Estévez S, Marrero MT, Quintana J, Estévez F. Eupatorin-induced cell death in human leukemia cells is dependent on caspases and activates the mitogen- activated protein kinase pathway. PLoS One. 2014 Nov 12;9(11):e112536. doi: 10.1371/journal.pone.0112536. PMID: 25390937; PMCID: PMC4229185. 8: Yam MF, Tan CS, Ahmad M, Shibao R. Mechanism of vasorelaxation induced by eupatorin in the rats aortic ring. Eur J Pharmacol. 2016 Oct 15;789:27-36. doi: 10.1016/j.ejphar.2016.06.047. Epub 2016 Jun 28. PMID: 27370961. 9: Salmela AL, Pouwels J, Kukkonen-Macchi A, Waris S, Toivonen P, Jaakkola K, Mäki-Jouppila J, Kallio L, Kallio MJ. The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis. Exp Cell Res. 2012 Mar 10;318(5):578-92. doi: 10.1016/j.yexcr.2011.12.014. Epub 2011 Dec 29. PMID: 22227008. 10: Rizou AEI, Nasi GI, Paikopoulos Y, Bezantakou DS, Vraila KD, Spatharas PM, Dimaki VD, Papandreou NC, Lamari FN, Chondrogianni N, Iconomidou VA. A Multilevel Study of Eupatorin and Scutellarein as Anti-Amyloid Agents in Alzheimer's Disease. Biomedicines. 2023 May 4;11(5):1357. doi: 10.3390/biomedicines11051357. PMID: 37239029; PMCID: PMC10216506. 11: Adams JH, Lewis JR. Eupatorin, a constituent of Merrillia caloxylon. Planta Med. 1977 Aug;32(1):86-7. doi: 10.1055/s-0028-1097564. PMID: 905420. 12: Namazi Sarvestani N, Sepehri H, Delphi L, Moridi Farimani M. Eupatorin and Salvigenin Potentiate Doxorubicin-Induced Apoptosis and Cell Cycle Arrest in HT-29 and SW948 Human Colon Cancer Cells. Asian Pac J Cancer Prev. 2018 Jan 27;19(1):131-139. doi: 10.22034/APJCP.2018.19.1.131. PMID: 29373904; PMCID: PMC5844607. 13: Sahid EDN, Claudino JC, Oda FB, Carvalho FA, Santos AGD, Graminha MAS, Clementino LDC. Baccharis trimera (Less.) DC leaf derivatives and eupatorin activities against Leishmania amazonensis. Nat Prod Res. 2022 Mar;36(6):1599-1603. doi: 10.1080/14786419.2021.1887175. Epub 2021 Feb 13. PMID: 33586545. 14: Dolečková I, Rárová L, Grúz J, Vondrusová M, Strnad M, Kryštof V. Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia. 2012 Sep;83(6):1000-7. doi: 10.1016/j.fitote.2012.06.002. Epub 2012 Jun 12. PMID: 22698713. 15: Tousi MS, Sepehri H, Khoee S, Farimani MM, Delphi L, Mansourizadeh F. Evaluation of apoptotic effects of mPEG-b-PLGA coated iron oxide nanoparticles as a eupatorin carrier on DU-145 and LNCaP human prostate cancer cell lines. J Pharm Anal. 2021 Feb;11(1):108-121. doi: 10.1016/j.jpha.2020.04.002. Epub 2020 Apr 18. PMID: 33717617; PMCID: PMC7930876. 16: Xu H, Yao N, Xu H, Wang T, Li G, Li Z. Characterization of the interaction between eupatorin and bovine serum albumin by spectroscopic and molecular modeling methods. Int J Mol Sci. 2013 Jul 9;14(7):14185-203. doi: 10.3390/ijms140714185. PMID: 23839090; PMCID: PMC3742238. 17: Feng R, Li L, Zhang X, Zhang Y, Chen Y, Feng X, Zhang L, Zhang G. Assessment of a developed HPLC-MS/MS approach for determining plasma eupatorin in rats and its application in pharmacokinetics analysis. RSC Adv. 2020 Aug 28;10(53):32020-32026. doi: 10.1039/d0ra03350b. PMID: 35518153; PMCID: PMC9056642. 18: Hong F, Zhao M, Xue LL, Ma X, Liu L, Cai XY, Zhang RJ, Li N, Wang L, Ni HF, Wu WS, Ye HY, Chen LJ. The ethanolic extract of Artemisia anomala exerts anti- inflammatory effects via inhibition of NLRP3 inflammasome. Phytomedicine. 2022 Jul 20;102:154163. doi: 10.1016/j.phymed.2022.154163. Epub 2022 May 10. PMID: 35597027. 19: Androutsopoulos VP, Li N, Arroo RR. The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells. J Nat Prod. 2009 Aug;72(8):1390-4. doi: 10.1021/np900051s. PMID: 19601638. 20: Androutsopoulos V, Arroo RR, Hall JF, Surichan S, Potter GA. Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism. Breast Cancer Res. 2008;10(3):R39. doi: 10.1186/bcr2090. Epub 2008 May 2. PMID: 18454852; PMCID: PMC2481486.