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MedKoo Cat#: 462466 | Name: Cirsiliol
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Description:

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

Cirsiliol is a flavonoid that has been found in S. indicum and has diverse biological activities.1 It inhibits 5-lipoxygenase (5-LO) and 12-LO.

Chemical Structure

Cirsiliol
Cirsiliol
CAS#34334-69-5

Theoretical Analysis

MedKoo Cat#: 462466

Name: Cirsiliol

CAS#: 34334-69-5

Chemical Formula: C17H14O7

Exact Mass: 330.0740

Molecular Weight: 330.29

Elemental Analysis: C, 61.82; H, 4.27; O, 33.91

Price and Availability

Size Price Availability Quantity
1mg USD 250.00 2 Weeks
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Synonym
Cirsiliol
IUPAC/Chemical Name
2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one
InChi Key
IMEYGBIXGJLUIS-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
SMILES Code
O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(OC)=C(OC)C(O)=C13
Appearance
Solid powder
Purity
>90% (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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.
In vitro activity:
Cirsiliol showed no cytotoxicity and inhibited pSTAT3-induced luciferase activity. At the molecular level, cirsiliol suppressed the expression of IL-6-induced inflammatory marker genes such as CRP, IL-1β, ICAM-1 and SOCS3, IL-6-induced activation of Jak2, gp130, STAT3 and ERK and nuclear translocation of STAT3, as measured by PCR, immunofluorescence staining and western blot analysis. These results indicate that cirsiliol attenuates IL-6-induced cellular signaling by regulating Jak2 phosphorylation. Reference: Bioorg Med Chem Lett. 2019 Jul 1;29(13):1586-1592. https://pubmed.ncbi.nlm.nih.gov/31060888/
In vivo activity:
In order to assess the anti-tumor activity of cirsiliol in vivo, LEG73 and LEG104 cases with high level of TYK2 were selected from the ESCC PDX specimen repository to develop the PDX mouse model (Fig. 7a & b). After administration of cirsiliol via oral gavage, the tumor volumes of high cirsiliol concentration treatment group in LEG73 case were suppressed when compared with the vehicle group (Fig. 7c). Reference: J Exp Clin Cancer Res. 2021; 40: 105. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7972218/

Preparing Stock Solutions

The following data is based on the product molecular weight 330.29 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. Lim HJ, Jang HJ, Bak SG, Lee S, Lee SW, Lee KM, Lee SJ, Rho MC. In vitro inhibitory effects of cirsiliol on IL-6-induced STAT3 activation through anti-inflammatory activity. Bioorg Med Chem Lett. 2019 Jul 1;29(13):1586-1592. doi: 10.1016/j.bmcl.2019.04.053. Epub 2019 May 2. PMID: 31060888. 2. Prasad P, Vasas A, Hohmann J, Bishayee A, Sinha D. Cirsiliol Suppressed Epithelial to Mesenchymal Transition in B16F10 Malignant Melanoma Cells through Alteration of the PI3K/Akt/NF-κB Signaling Pathway. Int J Mol Sci. 2019 Jan 31;20(3):608. doi: 10.3390/ijms20030608. PMID: 30708951; PMCID: PMC6386903. 3. Jia X, Huang C, Hu Y, Wu Q, Liu F, Nie W, Chen H, Li X, Dong Z, Liu K. Cirsiliol targets tyrosine kinase 2 to inhibit esophageal squamous cell carcinoma growth in vitro and in vivo. J Exp Clin Cancer Res. 2021 Mar 17;40(1):105. doi: 10.1186/s13046-021-01903-z. PMID: 33731185; PMCID: PMC7972218.
In vitro protocol:
1. Lim HJ, Jang HJ, Bak SG, Lee S, Lee SW, Lee KM, Lee SJ, Rho MC. In vitro inhibitory effects of cirsiliol on IL-6-induced STAT3 activation through anti-inflammatory activity. Bioorg Med Chem Lett. 2019 Jul 1;29(13):1586-1592. doi: 10.1016/j.bmcl.2019.04.053. Epub 2019 May 2. PMID: 31060888. 2. Prasad P, Vasas A, Hohmann J, Bishayee A, Sinha D. Cirsiliol Suppressed Epithelial to Mesenchymal Transition in B16F10 Malignant Melanoma Cells through Alteration of the PI3K/Akt/NF-κB Signaling Pathway. Int J Mol Sci. 2019 Jan 31;20(3):608. doi: 10.3390/ijms20030608. PMID: 30708951; PMCID: PMC6386903.
In vivo protocol:
1. Jia X, Huang C, Hu Y, Wu Q, Liu F, Nie W, Chen H, Li X, Dong Z, Liu K. Cirsiliol targets tyrosine kinase 2 to inhibit esophageal squamous cell carcinoma growth in vitro and in vivo. J Exp Clin Cancer Res. 2021 Mar 17;40(1):105. doi: 10.1186/s13046-021-01903-z. PMID: 33731185; PMCID: PMC7972218.
1: Jiang T, Peng L, Wang Q, Huang B, Peng D, Men L, Jiang Y, Zhu M, Wang M, Lin L, Lv J, Li S. Cirsiliol regulates mitophagy in colon cancer cells via STAT3 signaling. Cancer Cell Int. 2022 Oct 7;22(1):304. doi: 10.1186/s12935-022-02732-6. PMID: 36207761; PMCID: PMC9541001. 2: Hu H, Du W, Zhang W, Fang J. Cirsiliol mitigates Aβ fibrillation and underlying membrane-leakage associated neurotoxicity: A possible implication in the treatment of neurodegenerative disease. Int J Biol Macromol. 2022 Jul 31;213:915-922. doi: 10.1016/j.ijbiomac.2022.06.023. Epub 2022 Jun 8. PMID: 35688279. 3: Jia X, Huang C, Hu Y, Wu Q, Liu F, Nie W, Chen H, Li X, Dong Z, Liu K. Cirsiliol targets tyrosine kinase 2 to inhibit esophageal squamous cell carcinoma growth in vitro and in vivo. J Exp Clin Cancer Res. 2021 Mar 17;40(1):105. doi: 10.1186/s13046-021-01903-z. PMID: 33731185; PMCID: PMC7972218. 4: Prasad P, Vasas A, Hohmann J, Bishayee A, Sinha D. Cirsiliol Suppressed Epithelial to Mesenchymal Transition in B16F10 Malignant Melanoma Cells through Alteration of the PI3K/Akt/NF-κB Signaling Pathway. Int J Mol Sci. 2019 Jan 31;20(3):608. doi: 10.3390/ijms20030608. PMID: 30708951; PMCID: PMC6386903. 5: Carlini L, Tancreda G, Iobbi V, Caicci F, Bruno S, Esposito A, Calzia D, Benini S, Bisio A, Manni L, Schito A, Traverso CE, Ravera S, Panfoli I. The Flavone Cirsiliol from Salvia x jamensis Binds the F1 Moiety of ATP Synthase, Modulating Free Radical Production. Cells. 2022 Oct 9;11(19):3169. doi: 10.3390/cells11193169. PMID: 36231131; PMCID: PMC9562182. 6: Lim HJ, Jang HJ, Bak SG, Lee S, Lee SW, Lee KM, Lee SJ, Rho MC. In vitro inhibitory effects of cirsiliol on IL-6-induced STAT3 activation through anti- inflammatory activity. Bioorg Med Chem Lett. 2019 Jul 1;29(13):1586-1592. doi: 10.1016/j.bmcl.2019.04.053. Epub 2019 May 2. PMID: 31060888. 7: Mustafa EH, Abu Zarga M, Abdalla S. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated ileum. Gen Pharmacol. 1992 May;23(3):555-60. doi: 10.1016/0306-3623(92)90127-6. PMID: 1511863. 8: Kang J, Kim E, Kim W, Seong KM, Youn H, Kim JW, Kim J, Youn B. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non- small cell lung cancer cell lines. J Biol Chem. 2013 Sep 20;288(38):27343-27357. doi: 10.1074/jbc.M113.490482. Epub 2013 Jul 31. PMID: 23902763; PMCID: PMC3779729. 9: Marder M, Viola H, Wasowski C, Wolfman C, Waterman PG, Medina JH, Paladini AC. Cirsiliol and caffeic acid ethyl ester, isolated from Salvia guaranitica, are competitive ligands for the central benzodiazepine receptors. Phytomedicine. 1996 May;3(1):29-31. doi: 10.1016/S0944-7113(96)80006-7. PMID: 23194857. 10: de Oliveira AP, Borges IV, Pereira ECV, Feitosa TA, Dos Santos RF, de Oliveira-Junior RG, Rolim LA, Cordeiro Viana LGF, Ribeiro LAA, Santos ADDC, Rolim-Neto PJ, Almeida JRGDS. Influence of light intensity, fertilizing and season on the cirsiliol content, a chemical marker of Leonotis nepetifolia (Lamiaceae). PeerJ. 2019 Jan 15;7:e6187. doi: 10.7717/peerj.6187. PMID: 30671296; PMCID: PMC6338097. 11: Viola H, Wasowski C, Marder M, Wolfman C, Paladini AC, Medina JH. Sedative and hypnotic properties of Salvia guaranitica St. Hil. and of its active principle, Cirsiliol. Phytomedicine. 1997 Mar;4(1):47-52. doi: 10.1016/S0944-7113(97)80027-X. PMID: 23195245. 12: 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. 13: Oliveira AP, Silva ALN, Viana LGFC, Silva MG, Lavor ÉM, Oliveira-Júnior RG, Alencar-Filho EB, Lima RS, Mendes RL, Rolim LA, Anjos DSC, Ferraz LRM, Rolim- Neto PJ, Silva MFS, Pessoa CDÓ, Almeida JRGS. β-Cyclodextrin complex improves the bioavailability and antitumor potential of cirsiliol, a flavone isolated from Leonotis nepetifolia (Lamiaceae). Heliyon. 2019 Nov 1;5(10):e01692. doi: 10.1016/j.heliyon.2019.e01692. PMID: 31720439; PMCID: PMC6838880. 14: Yanagimichi M, Nishino K, Sakamoto A, Kurodai R, Kojima K, Eto N, Isoda H, Ksouri R, Irie K, Kambe T, Masuda S, Akita T, Maejima K, Nagao M. Analyses of putative anti-cancer potential of three STAT3 signaling inhibitory compounds derived from Salvia officinalis. Biochem Biophys Rep. 2020 Dec 24;25:100882. doi: 10.1016/j.bbrep.2020.100882. PMID: 33392396; PMCID: PMC7772785. 15: Marder M, Paladini AC. GABA(A)-receptor ligands of flavonoid structure. Curr Top Med Chem. 2002 Aug;2(8):853-67. doi: 10.2174/1568026023393462. PMID: 12171576. 16: Metoui R, Bouajila J, Znati M, Cazaux S, Neffati M, Akrout A. Bioactive flavones isolated from Tunisian Artemisia campestris L. Leaves. Cell Mol Biol (Noisy-le-grand). 2017 Nov 30;63(11):86-91. doi: 10.14715/cmb/2017.63.11.15. PMID: 29208178. 17: Li J, Fronczek FR, Ferreira D, Burandt CL Jr, Setola V, Roth BL, Zjawiony JK. Bis-spirolabdane diterpenoids from Leonotis nepetaefolia. J Nat Prod. 2012 Apr 27;75(4):728-34. doi: 10.1021/np3000156. Epub 2012 Apr 4. PMID: 22475308; PMCID: PMC3338874. 18: Forgo P, Zupkó I, Molnár J, Vasas A, Dombi G, Hohmann J. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul;83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. Epub 2012 Apr 17. PMID: 22537643. 19: Kohno SW, Ohata K, Maki Y, Horie T, Yoshimoto T, Yamamoto S. Potent and selective 5-lipoxygenase inhibitors: cirsiliol and AA-861. Adv Prostaglandin Thromboxane Leukot Res. 1985;15:217-9. PMID: 2936097. 20: Dai LP, Zhao M, Li C, Zhao JJ, Zhang LX, Chen SQ, Gao HM, Wang ZM. [Studies on chemical constituents of Isodon excisoides]. Zhongguo Zhong Yao Za Zhi. 2016 Sep;41(18):3361-3365. Chinese. doi: 10.4268/cjcmm20161809. PMID: 28925118.