Tussilagone

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

MedKoo CAT#: 563473

CAS#: 104012-37-5

Description: Tussilagone is an inhibitor on ß-catenin dependent Wnt pathway. It acts by suppressing ß-catenin/T-cell factor transcriptional activity and down-regulating ß-catenin level.

Chemical Structure

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Tussilagone
CAS# 104012-37-5
Instruction

Theoretical Analysis

MedKoo Cat#: 563473
Name: Tussilagone
CAS#: 104012-37-5
Chemical Formula: C23H34O5
Exact Mass: 390.24
Molecular Weight: 390.520
Elemental Analysis: C, 70.74; H, 8.78; O, 20.48

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Tussilagone; L-652469; L 652469; L652469; TSL;

IUPAC/Chemical Name: (1R,3aR,5R,7S,7aS)-1-(1-acetoxyethyl)-7-isopropyl-4-methylene-2-oxooctahydro-1H-inden-5-yl (E)-3-methylpent-2-enoate

InChi Key: CFUPNMDNSQIWBB-ACCKDKKQSA-N

InChi Code: InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+/t15?,17-,18-,20+,22+,23-/m0/s1

SMILES Code: CC/C(C)=C/C(O[C@H]1C([C@]2([H])CC([C@@H](C(OC(C)=O)C)[C@@]2([H])[C@H](C(C)C)C1)=O)=C)=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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 390.52 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:
In vitro protocol:
In vivo protocol:

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1: Kim YK, Yeo MG, Oh BK, Kim HY, Yang HJ, Cho SS, Gil M, Lee KJ. Tussilagone Inhibits the Inflammatory Response and Improves Survival in CLP-Induced Septic Mice. Int J Mol Sci. 2017 Dec 18;18(12). pii: E2744. doi: 10.3390/ijms18122744. PubMed PMID: 29258263; PubMed Central PMCID: PMC5751343.

2: Cheng X, Liao M, Diao X, Sun Y, Zhang L. Screening and identification of metabolites of two kinds of main active ingredients and hepatotoxic pyrrolizidine alkaloids in rat after lavage Farfarae Flos extract by UHPLC-Q-TOF-MS mass spectrometry. Biomed Chromatogr. 2018 Feb;32(2). doi: 10.1002/bmc.4047. Epub 2017 Aug 18. PubMed PMID: 28702943.

3: Song K, Lee KJ, Kim YS. Development of an efficient fractionation method for the preparative separation of sesquiterpenoids from Tussilago farfara by counter-current chromatography. J Chromatogr A. 2017 Mar 17;1489:107-114. doi: 10.1016/j.chroma.2017.02.005. Epub 2017 Feb 3. PubMed PMID: 28215402.

4: Cao K, Xu Y, Zhao TM, Zhang Q. Preparation of Sesquiterpenoids from Tussilago farfara L. by High-speed Counter-current Chromatography. Pharmacogn Mag. 2016 Oct-Dec;12(48):282-287. PubMed PMID: 27867270; PubMed Central PMCID: PMC5096274.

5: Lee J, Kang U, Seo EK, Kim YS. Heme oxygenase-1-mediated anti-inflammatory effects of tussilagonone on macrophages and 12-O-tetradecanoylphorbol-13-acetate-induced skin inflammation in mice. Int Immunopharmacol. 2016 May;34:155-164. doi: 10.1016/j.intimp.2016.02.026. Epub 2016 Mar 5. PubMed PMID: 26950613.

6: Zhang XS, Ren W, Bian BL, Zhao HY, Wang S. Comparative metabolism of tussilagone in rat and human liver microsomes using ultra-high-performance liquid chromatography coupled with high-resolution LTQ-Orbitrap mass spectrometry. Rapid Commun Mass Spectrom. 2015 Sep 30;29(18):1641-50. doi: 10.1002/rcm.7262. PubMed PMID: 26467116.

7: Li D, Liang L, Zhang J, Kang T. Application of microscopy technique and high-performance liquid chromatography for quality assessment of the flower bud of Tussilago farfara L. (Kuandonghua). Pharmacogn Mag. 2015 Jul-Sep;11(43):594-600. doi: 10.4103/0973-1296.160473. PubMed PMID: 26246737; PubMed Central PMCID: PMC4522848.

8: Zhang ZZ, Zhi HJ, Qin XM, Li ZY. [Chemical comparison of different Farfarae Flos by NMR-based metabolomic approaches]. Yao Xue Xue Bao. 2015 May;50(5):599-604. Chinese. PubMed PMID: 26234144.

9: Seo UM, Zhao BT, Kim WI, Seo EK, Lee JH, Min BS, Shin BS, Son JK, Woo MH. Quality evaluation and pattern recognition analyses of bioactive marker compounds from Farfarae Flos using HPLC/PDA. Chem Pharm Bull (Tokyo). 2015;63(7):546-53. doi: 10.1248/cpb.c15-00204. Epub 2015 May 14. PubMed PMID: 25971744.

10: Park Y, Ryu HS, Lee HK, Kim JS, Yun J, Kang JS, Hwang BY, Hong JT, Kim Y, Han SB. Tussilagone inhibits dendritic cell functions via induction of heme oxygenase-1. Int Immunopharmacol. 2014 Oct;22(2):400-8. doi: 10.1016/j.intimp.2014.07.023. Epub 2014 Aug 1. PubMed PMID: 25091622.

11: Qin ZB, Zhang J, Wu XD, He J, Ding LF, Peng LY, Li XY, Li Y, Deng L, Guo YD, Zhao QS. Sesquiterpenoids from Tussilago farfara and their inhibitory effects on nitric oxide production. Planta Med. 2014 Jun;80(8-9):703-9. doi: 10.1055/s-0034-1368567. Epub 2014 Jun 25. PubMed PMID: 24963619.

12: Mi X, Li ZY, Qin XM, Zhang LZ. [Monitoring of chemical components with different color traits of Tussilago farfara using NMR-based metabolomics]. Yao Xue Xue Bao. 2013 Nov;48(11):1692-7. Chinese. PubMed PMID: 24475707.

13: Li H, Lee HJ, Ahn YH, Kwon HJ, Jang CY, Kim WY, Ryu JH. Tussilagone suppresses colon cancer cell proliferation by promoting the degradation of β-catenin. Biochem Biophys Res Commun. 2014 Jan 3;443(1):132-7. doi: 10.1016/j.bbrc.2013.11.062. Epub 2013 Nov 22. PubMed PMID: 24269588.

14: Zhi HJ, Qin XM, Sun HF, Zhang LZ, Guo XQ, Li ZY. Metabolic fingerprinting of Tussilago farfara L. using ¹H-NMR spectroscopy and multivariate data analysis. Phytochem Anal. 2012 Sep-Oct;23(5):492-501. doi: 10.1002/pca.2346. Epub 2012 Feb 28. PubMed PMID: 22371211.

15: Hwangbo C, Lee HS, Park J, Choe J, Lee JH. The anti-inflammatory effect of tussilagone, from Tussilago farfara, is mediated by the induction of heme oxygenase-1 in murine macrophages. Int Immunopharmacol. 2009 Dec;9(13-14):1578-84. doi: 10.1016/j.intimp.2009.09.016. Epub 2009 Oct 1. PubMed PMID: 19800419.

16: Liu YF, Yang XW. [HPLC fingerprint of chemical constituents of Flos Farfarae]. Yao Xue Xue Bao. 2009 May;44(5):510-4. Chinese. PubMed PMID: 19618728.

17: Park HR, Yoo MY, Seo JH, Kim IS, Kim NY, Kang JY, Cui L, Lee CS, Lee CH, Lee HS. Sesquiterpenoids isolated from the flower buds of Tussilago farfara L. inhibit diacylglycerol acyltransferase. J Agric Food Chem. 2008 Nov 26;56(22):10493-7. doi: 10.1021/jf801978r. PubMed PMID: 18937486.

18: Liu YF, Yang XW, Lu W, Xin XL. Determination and pharmacokinetic study of tussilagone in rat plasma by RP-HPLC method. Biomed Chromatogr. 2008 Nov;22(11):1194-200. doi: 10.1002/bmc.1042. PubMed PMID: 18651585.

19: Lim HJ, Lee HS, Ryu JH. Suppression of inducible nitric oxide synthase and cyclooxygenase-2 expression by tussilagone from Farfarae flos in BV-2 microglial cells. Arch Pharm Res. 2008 May;31(5):645-52. doi: 10.1007/s12272-001-1207-4. Epub 2008 May 15. PubMed PMID: 18481023.

20: Mi JF, Xu RS, Yang YP, Yang PM. [Studies on circular dichroism of diterpenoids from Mallotus anomalus and sesquiterpenoid tussilagone]. Yao Xue Xue Bao. 1993;28(2):105-9. Chinese. PubMed PMID: 8328277.