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 Chrysophanic acid

Description of Chrysophanic acid: 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. (source: Phytother Res. 2011 Jun;25(6):833-7. )

Current developer: 

1: Seo EJ, Ngoc TM, Lee SM, Kim YS, Jung YS. Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet 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 Effects of Emodin and Chrysophanol Isolated from Marine Fungus Aspergillus sp. on Ethanol-Induced Toxicity in HepG2/CYP2E1 Cells. Evid Based Complement Alternat 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 of aurantio-obtusin and chrysophanol in cassiae semen by HPLC]. Zhongguo Zhong 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-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation 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 production of ROS and alteration of ATP levels in J5 human liver cancer cells. Mol Nutr Food Res. 2010 Jul;54(7):967-76. PubMed PMID: 20169580; PubMed Central PMCID: PMC3031088.

6: Genovese S, Tammaro F, Menghini L, Carlucci G, Epifano F, Locatelli M. Comparison of three different extraction methods and HPLC determination 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. Multiple convergence in polyketide biosynthesis: a third folding mode to the anthraquinone 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 the photo-physicochemical properties of chrysophanol from rheum. Int J Mol Sci. 2009 Jul 13;10(7):3186-93. PubMed PMID: 19742131; PubMed Central PMCID: PMC2738918.

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

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

11: Fiedler HP, Dieter A, Gulder TA, Kajahn I, Hamm A, Brown R, Jones AL, Goodfellow M, Müller WE, Bringmann G. Genoketides A1 and A2, new octaketides and biosynthetic intermediates of chrysophanol produced by Streptomyces sp. AK 671. J Antibiot (Tokyo). 2008 Jul;61(7):464-73. PubMed PMID: 18776659.

12: Teng ZH, Zhou SY, Ran YH, Liu XY, Yang RT, Yang X, Yuan CJ, Mei QB. Cellular absorption of anthraquinones emodin and chrysophanol in human intestinal Caco-2 cells. Biosci Biotechnol Biochem. 2007 Jul;71(7):1636-43. Epub 2007 Jul 7. PubMed PMID: 17617731.

13: Yang X, Yang L, Wang S, Yu D, Ni H. Synergistic interaction of physcion and chrysophanol on plant powdery mildew. Pest Manag Sci. 2007 May;63(5):511-5. PubMed PMID: 17397111.

14: Tang WF, Yu Q, Wan MH, Qin F, Wang YG, Chen GY, Liang MZ, Huang X. Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography. Biomed Chromatogr. 2007 Jul;21(7):701-7. PubMed PMID: 17370297.

15: Yang HM, Chen B, Zeng JG, Miao JR. [Simultaneous determination of resveratrol, emodin, chrysophanol, physcion, in root of Polygonam cuspidatum and its extract by HPLC]. Zhongguo Zhong Yao Za Zhi. 2006 Feb;31(3):202-5. Chinese. PubMed PMID: 16572998.

16: Mao P, Xu J, Wu YM. [Study on releasing rate of chrysophanol from Ruyi Jinhuang plaster]. Zhongguo Zhong Yao Za Zhi. 2004 Aug;29(8):746-7, 816. Chinese. PubMed PMID: 15506283.

17: Ito H, Nishida Y, Yamazaki M, Nakahara K, Michalska-Hartwich M, Furmanowa M, Leistner E, Yoshida T. Chrysophanol glycosides from callus cultures of monocotyledonous Kniphofia spp. (Asphodelaceae). Chem Pharm Bull (Tokyo). 2004 Oct;52(10):1262-4. PubMed PMID: 15467251.

18: Koyama J, Morita I, Kawanishi K, Tagahara K, Kobayashi N. Capillary electrophoresis for simultaneous determination of emodin, chrysophanol, and their 8-beta-D-glucosides. Chem Pharm Bull (Tokyo). 2003 Apr;51(4):418-20. PubMed PMID: 12672996.

19: Mengs U, Schuler D, Marshall RR. No induction of chromosomal aberrations in Chinese hamster ovary cells by chrysophanol. Mutat Res. 2001 May 31;492(1-2):69-72. PubMed PMID: 11377245.

20: Kim DH, Park EK, Bae EA, Han MJ. Metabolism of rhaponticin and chrysophanol 8-o-beta-D-glucopyranoside from the rhizome of rheum undulatum by human intestinal bacteria and their anti-allergic actions. Biol Pharm Bull. 2000 Jul;23(7):830-3. PubMed PMID: 10919361.

21: Wu L, Yang X, Chen X, Liu X. [Optimization of quenching system for determination of emodin and chrysophanol by chemiluminescence method]. Hua Xi Yi Ke Da Xue Xue Bao. 1997 Sep;28(3):341-3. Chinese. PubMed PMID: 10684049.

22: Mueller SO, Schmitt M, Dekant W, Stopper H, Schlatter J, Schreier P, Lutz WK. Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. Food Chem Toxicol. 1999 May;37(5):481-91. PubMed PMID: 10456676.

23: Mueller SO, Stopper H, Dekant W. Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Bioactivation to genotoxic metabolites. Drug Metab Dispos. 1998 Jun;26(6):540-6. PubMed PMID: 9616189.

24: Cao A, Sha M, Meng S, Jiang L, Zhang Z. [Determination of chrysophanol in semen Cassiae by HPLC]. Zhongguo Zhong Yao Za Zhi. 1997 Feb;22(2):107-8, 128, inside back cover. Chinese. PubMed PMID: 10743205.

25: Darzynkiewicz Z, Carter SP, Kapuscinski J, Watanabe KA. Effect of derivatives of chrysophanol, a new type of potential antitumor agents of anthraquinone family, on growth and cell cycle of L1210 leukemic cells. Cancer Lett. 1989 Aug;46(3):181-7. PubMed PMID: 2766258.

26: Koyama M, Takahashi K, Chou TC, Darzynkiewicz Z, Kapuscinski J, Kelly TR, Watanabe KA. Intercalating agents with covalent bond forming capability. A novel type of potential anticancer agents. 2. Derivatives of chrysophanol and emodin. J Med Chem. 1989 Jul;32(7):1594-9. PubMed PMID: 2738893.

27: Koyama M, Kelly TR, Watanabe KA. Novel type of potential anticancer agents derived from chrysophanol and emodin. Some structure-activity relationship studies. J Med Chem. 1988 Feb;31(2):283-4. PubMed PMID: 3339601.

28: Liberman DF, Schaefer FL, Fink RC, Ramgopal M, Ghosh AC, Mulcahy R. Mutagenicity of islandicin and chrysophanol in the Salmonella/microsome system. Appl Environ Microbiol. 1980 Sep;40(3):476-9. PubMed PMID: 6999990; PubMed Central PMCID: PMC291608.

29: Harris TM, Webb AD, Harris CM, Wittek PJ, Murray TP. Letter: Biogenetic-type syntheses of emodin and chrysophanol. J Am Chem Soc. 1976 Sep 15;98(19):6065-7. PubMed PMID: 965641.

30: Vogt E, Mühlemann H. [Anthraquinones and anthraquinonglycosides. 20. Partial synthetic study on chrysophanol- and chrysazin-anthraquinones and -glycosides]. Pharm Acta Helv. 1971 Oct-Nov;46(10):657-70. German. PubMed PMID: 5142418.

31: Vogt E, Mühlemann H. [Anthraquinones and anthraquinone glycosides. 20. Partial synthetic experiments with chrysophanol-and chrysacin-anthraquinones and glycosides]. Pharm Acta Helv. 1971 Jul;46(7):431-40. German. PubMed PMID: 4934854.