Chrysophanic acid

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

Description:Chrysophanic acid (Chrysophanol ) is a a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µm) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. These findings offer the first evidence of anticancer activity for chrysophanic acid via EGFR/mTOR mediated signaling transduction pathway.

Price and Availability

Chrysophanol, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 401220Name: Chrysophanic acidCAS#: 481-74-3Chemical Formula: C15H10O4Exact Mass: 254.05791Molecular Weight: 254.2375Elemental Analysis:C, 70.86; H, 3.96; O, 25.17

Synonym:Chrysophanol; Chrysophanic acid

IUPAC/Chemical Name:1,8-dihydroxy-3-methylanthracene-9,10-dione

InChi Key:1,8-dihydroxy-3-methylanthracene-9,10-dione

InChi Code:InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

SMILES Code:O=C1C2=C(C=CC=C2O)C(C3=CC(C)=CC(O)=C13)=O

Technical Data

Additional Information

References

1: Seo EJ, Ngoc TM, Lee SM, Kim YS, Jung YS.Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, HasAntiplatelet and Anticoagulant Activities. J Pharmacol Sci. 2012 Feb 3.[Epub ahead of print] PubMed PMID: 22302018.

2: Qian ZJ, Zhang C, Li YX, Je JY, Kim SK, Jung WK. Protective Effectsof Emodin and Chrysophanol Isolated from Marine Fungus Aspergillus sp.on Ethanol-Induced Toxicity in HepG2/CYP2E1 Cells. Evid Based ComplementAlternat Med. 2011;2011:452621. Epub 2011 Sep 6. PubMed PMID: 21912566;PubMed Central PMCID: PMC3168298.

3: Huang X, Zhong G, Zhang X, Zhang Y. [Determination ofaurantio-obtusin and chrysophanol in cassiae semen by HPLC]. ZhongguoZhong Yao Za Zhi. 2010 Aug;35(16):2065-7. Chinese. PubMed PMID:21046729.

4: Kim SJ, Kim MC, Lee BJ, Park DH, Hong SH, Um JY. Anti-Inflammatoryactivity of chrysophanol through the suppression of NF-kappaB/caspase-1activation in vitro and in vivo. Molecules. 2010 Sep 16;15(9):6436-51.PubMed PMID: 20877234.

5: Lu CC, Yang JS, Huang AC, Hsia TC, Chou ST, Kuo CL, Lu HF, Lee TH,Wood WG, Chung JG. Chrysophanol induces necrosis through the productionof ROS and alteration of ATP levels in J5 human liver cancer cells. MolNutr Food Res. 2010 Jul;54(7):967-76. PubMed PMID: 20169580; PubMedCentral PMCID: PMC3031088.

6: Genovese S, Tammaro F, Menghini L, Carlucci G, Epifano F, LocatelliM. Comparison of three different extraction methods and HPLCdetermination of the anthraquinones aloe-emodine, emodine, rheine,chrysophanol and physcione in the bark of Rhamnus alpinus L. (Rhamnaceae).Phytochem Anal. 2010 May;21(3):261-7. PubMed PMID: 20024894.

7: Bringmann G, Gulder TA, Hamm A, Goodfellow M, Fiedler HP. Multipleconvergence in polyketide biosynthesis: a third folding mode to theanthraquinone chrysophanol. Chem Commun (Camb). 2009 Nov 28;(44):6810-2.Epub 2009 Oct 5. PubMed PMID: 19885487.

8: Zhao X, Zheng Z, Feng S, Shi Z, Chen D. A TD-DFT study on thephoto-physicochemical properties of chrysophanol from rheum. Int J MolSci. 2009 Jul 13;10(7):3186-93. PubMed PMID: 19742131; PubMed CentralPMCID: PMC2738918.

9: Jiao Y, Zuo Y. Ultrasonic extraction and HPLC determination ofanthraquinones, aloe-emodine, emodine, rheine, chrysophanol andphyscione, in roots of Polygoni multiflori. Phytochem Anal. 2009Jul;20(4):272-8. PubMed PMID: 19402184.

10: Lee MS, Sohn CB. Anti-diabetic properties of chrysophanol and itsglucoside from rhubarb rhizome. Biol Pharm Bull. 2008 Nov;31(11):2154-7.PubMed PMID: 18981591.