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MedKoo Cat#: 412944 | Name: Cirsimarin
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Description:

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

Cirsimarin is a potent antilipogenic flavonoid isolated from Microtea debilis. Cirsimarin exerts potent antilipogenic effect and decreases adipose tissue deposition in mice. The lipolytic activity of Cirsimarin resulting from both its antagonist activity on adenosin A1 receptor and its inhibitory effect on phosphodiesterase.

Chemical Structure

Cirsimarin
Cirsimarin
CAS#13020-19-4

Theoretical Analysis

MedKoo Cat#: 412944

Name: Cirsimarin

CAS#: 13020-19-4

Chemical Formula: C23H24O11

Exact Mass: 476.1319

Molecular Weight: 476.43

Elemental Analysis: C, 57.98; H, 5.08; O, 36.94

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
Cirsimarin; Cirsitakaoside; Cirsimaretin
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-
InChi Key
RETJLKUBHXTIGH-FZFRBNDOSA-N
InChi Code
InChI=1S/C23H24O11/c1-30-15-8-14-17(19(27)22(15)31-2)12(25)7-13(33-14)10-3-5-11(6-4-10)32-23-21(29)20(28)18(26)16(9-24)34-23/h3-8,16,18,20-21,23-24,26-29H,9H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1
SMILES Code
O=C1C=C(C2=CC=C(O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C=C2)OC4=CC(OC)=C(OC)C(O)=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 476.43 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
1: Zarrouki B, Pillon NJ, Kalbacher E, Soula HA, Nia N'Jomen G, Grand L, Chambert S, Geloen A, Soulage CO. Cirsimarin, a potent antilipogenic flavonoid, decreases fat deposition in mice intra-abdominal adipose tissue. Int J Obes (Lond). 2010 Nov;34(11):1566-75. doi: 10.1038/ijo.2010.85. Epub 2010 May 11. PMID: 20458325. 2: Serpeloni JM, Oliveira LCB, Fujiike A, Tuttis K, Ribeiro DL, Camara MBP, Rocha CQD, Cólus IMS. Flavone cirsimarin impairs cell proliferation, migration, and invasion in MCF-7 cells grown in 2D and 3D models. Toxicol In Vitro. 2022 Sep;83:105416. doi: 10.1016/j.tiv.2022.105416. Epub 2022 Jun 13. PMID: 35710092. 3: Han HS, Shin JS, Lee SB, Park JC, Lee KT. Cirsimarin, a flavone glucoside from the aerial part of Cirsium japonicum var. ussuriense (Regel) Kitam. ex Ohwi, suppresses the JAK/STAT and IRF-3 signaling pathway in LPS-stimulated RAW 264.7 macrophages. Chem Biol Interact. 2018 Sep 25;293:38-47. doi: 10.1016/j.cbi.2018.07.024. Epub 2018 Jul 25. PMID: 30053449. 4: Hasrat JA, De Bruyne T, De Backer JP, Vauquelin G, Vlietinck AJ. Cirsimarin and cirsimaritin, flavonoids of Microtea debilis (Phytolaccaceae) with adenosine antagonistic properties in rats: leads for new therapeutics in acute renal failure. J Pharm Pharmacol. 1997 Nov;49(11):1150-6. doi: 10.1111/j.2042-7158.1997.tb06059.x. PMID: 9401955. 5: Zhang E, Wang Y, Xie F, Zhuang X, Wang X, Yu X. Development and Validation of a UPLC-MS/MS Method for the Quantitative Determination and Pharmacokinetic Analysis of Cirsimarin in Rat Plasma. Biomed Res Int. 2021 Jun 8;2021:9953664. doi: 10.1155/2021/9953664. PMID: 34212043; PMCID: PMC8205585. 6: Girotti C, Ginet M, Demarne FC, Lagarde M, Géloën A. Lipolytic activity of cirsimarin extracted from Microtea debilis. Planta Med. 2005 Dec;71(12):1170-2. doi: 10.1055/s-2005-873146. PMID: 16395657. 7: Hasrat JA, Pieters L, Claeys M, Vlietinck A, De Backer JP, Vauquelin G. Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis. J Nat Prod. 1997 Jun;60(6):638-41. doi: 10.1021/np970025k. PMID: 9214739. 8: Cho C, Kang LJ, Jang D, Jeon J, Lee H, Choi S, Han SJ, Oh E, Nam J, Kim CS, Park E, Jeong SY, Park CH, Shin YS, Eyun SI, Yang S. Cirsium japonicum var. maackii and apigenin block Hif-2α-induced osteoarthritic cartilage destruction. J Cell Mol Med. 2019 Aug;23(8):5369-5379. doi: 10.1111/jcmm.14418. Epub 2019 May 31. PMID: 31148341; PMCID: PMC6652892. 9: Jeong DM, Jung HA, Choi JS. Comparative antioxidant activity and HPLC profiles of some selected Korean thistles. Arch Pharm Res. 2008 Jan;31(1):28-33. doi: 10.1007/s12272-008-1116-7. PMID: 18277604. 10: Sreeja PS, Arunachalam K, Martins DTO, Lima JCDS, Balogun SO, Pavan E, Saikumar S, Dhivya S, Kasipandi M, Parimelazhagan T. Sphenodesme involucrata var. paniculata (C.B. Clarke) Munir.: Chemical characterization, anti- nociceptive and anti-inflammatory activities of methanol extract of leaves. J Ethnopharmacol. 2018 Oct 28;225:71-80. doi: 10.1016/j.jep.2018.06.035. Epub 2018 Jun 28. PMID: 29960023. 11: Bai N, He K, Roller M, Lai CS, Shao X, Pan MH, Bily A, Ho CT. Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects. Fitoterapia. 2011 Mar;82(2):168-72. doi: 10.1016/j.fitote.2010.08.014. Epub 2010 Sep 8. PMID: 20804824. 12: Yim SH, Kim HJ, Lee IS. A polyacetylene and flavonoids from Cirsium rhinoceros. Arch Pharm Res. 2003 Feb;26(2):128-31. doi: 10.1007/BF02976657. PMID: 12643588. 13: Yi ML, Sheng XF, Xu KP, Tan GS, Zou H. [Flavonoids from Selaginella uncinata]. Zhongguo Zhong Yao Za Zhi. 2015 Aug;40(15):3005-8. Chinese. PMID: 26677701. 14: Bel Mabrouk S, Reis M, Sousa ML, Ribeiro T, Almeida JR, Pereira S, Antunes J, Rosa F, Vasconcelos V, Achour L, Kacem A, Urbatzka R. The Marine Seagrass Halophila stipulacea as a Source of Bioactive Metabolites against Obesity and Biofouling. Mar Drugs. 2020 Jan 29;18(2):88. doi: 10.3390/md18020088. PMID: 32013082; PMCID: PMC7074557. 15: Zhu H, Pu D, Di Q, Zhao X, Ji F, Li H, Zhao Z, Gao J, Xiao W, Chen W. Cirsitakaoside isolated from Premna szemaoensis reduces LPS-induced inflammatory responses in vitro and in vivo. Int Immunopharmacol. 2018 Jun;59:384-390. doi: 10.1016/j.intimp.2018.04.030. Epub 2018 Apr 24. PMID: 29689498. 16: Laitinen JT. Selective detection of adenosine A1 receptor-dependent G-protein activity in basal and stimulated conditions of rat brain [35S]guanosine 5'-(gamma-thio)triphosphate autoradiography. Neuroscience. 1999;90(4):1265-79. doi: 10.1016/s0306-4522(98)00571-5. PMID: 10338296. 17: Savinainen JR, Saario SM, Niemi R, Järvinen T, Laitinen JT. An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors. Br J Pharmacol. 2003 Dec;140(8):1451-9. doi: 10.1038/sj.bjp.0705577. Epub 2003 Nov 17. PMID: 14623770; PMCID: PMC1574161. 18: Di Q, Zhu H, Pu D, Zhao X, Li X, Ma X, Xiao W, Chen W. The natural compound Cirsitakaoside enhances antiviral innate responses against vesicular stomatitis virus in vitro and in vivo. Int Immunopharmacol. 2020 Sep;86:106783. doi: 10.1016/j.intimp.2020.106783. Epub 2020 Jul 8. PMID: 32652505. 19: Pereira-Martins SR, Takahashi CS, Tavares DC, Torres LM. In vitro and in vivo study of the clastogenicity of the flavone cirsitakaoside extracted from Scoparia dulcis L. (Scrophulariaceae). Teratog Carcinog Mutagen. 1998;18(6):293-302. doi: 10.1002/(sici)1520-6866(1998)18:6<293::aid- tcm3>3.0.co;2-6. PMID: 10052564.