Metabolites of Ginger Component [6]-Shogaol Remain Bioactive in Cancer Cells and Have Low Toxicity in Normal Cells: Chemical Synthesis and Biological Evaluation

PLoS ONE

Volumn 8, Issue 1, 2013, Pages

  Zhu, Yingdong ^a   Warin, Renaud F ^a   Soroka, Dominique N ^a   Chen, Huadong ^a   Sang, Shengmin ^a  

^a NORTH CAROLINA A AND T STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3',4' DIHYDROXYPHENYL)DECAN 3 ONE; 1 (4' HYDROXY 3' METHOXYPHENYL) 4 DECEN 3 OL; 1 (4' HYDROXY 3' METHOXYPHENYL)DECAN 3 OL; 1 (4' HYDROXY 3' METHOXYPHENYL)DECAN 3 ONE; 5 CYSTEINYL 1 (4' HYDROXY 3' METHOXYPHENYL) 4 DECEN 3 OL; 5 CYSTEINYL[6]SHOGAOL; 5 GLUTATHIOL[6]SHOGAOL; 5 METHOXY 1 (4' HYDROXY 3' METHOXYPHENYL)DECAN 3 ONE; 5 METHYLTHIO 1 (4' HYDROXY 3' METHOXYPHENYL)DECAN 3 OL; 5 METHYLTHIO 1 (4' HYDROXY 3' METHOXYPHENYL)DECAN 3 ONE; 5 N ACETYLCYSTEINYL 1 (4' HYDROXY 3' METHOXYPHENYL) 4 DECEN 3 OL; 5 N ACETYLCYSTEINYL[6]SHOGAOL; DRUG METABOLITE; SHOGAOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER INHIBITION; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETOXIFICATION; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; GINGER; HUMAN; HUMAN CELL; IC 50; LUNG ALVEOLUS CELL; NICK END LABELING;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CATECHOLS; CELL LINE; GINGER; HCT116 CELLS; HUMANS;

EID: 84873858348     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0054677     Document Type: Article

References (20)

1. Sarkar FH, Li Y, (2009) Harnessing the fruits of nature for the development of multi-targeted cancer therapeutics. Cancer Treat Rev 35: 597-607.
2. Crowell JA, (2005) The chemopreventive agent development research program in the Division of Cancer Prevention of the US National Cancer Institute: an overview. Eur J Cancer 41: 1889-1910.
3. Surh YJ, (2003) Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer 3: 768-780.
4. Stan SD, Kar S, Stoner GD, Singh SV, (2008) Bioactive food components and cancer risk reduction. J Cell Biochem 104: 339-356.
5. Kubra IR, Rao LJ, (2012) An impression on current developments in the technology, chemistry, and biological activities of ginger (Zingiber officinale Roscoe). Crit Rev Food Sci Nutr 52: 651-688.
6. Haniadka R, Rajeev AG, Palatty PL, Arora R, Baliga MS, (2012) Zingiber officinale (Ginger) as an Anti-Emetic in Cancer Chemotherapy: A Review. J Altern Complement Med 18: 440-444.
7. Baliga MS, Haniadka R, Pereira MM, D'Souza JJ, Pallaty PL, et al. (2012) Update on the chemopreventive effects of ginger and its phytochemicals. Crit Rev Food Sci Nutr 51: 499-523.
8. Sang S, Hong J, Wu H, Liu J, Yang CS, et al. (2009) Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J Agric Food Chem 57: 10645-10650.
9. Kim JS, Lee SI, Park HW, Yang JH, Shin TY, et al. (2008) Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe. Arch Pharm Res 31: 415-418.
10. Wu H, Hsieh MC, Lo CY, Liu CB, Sang S, et al. (2010) 6-Shogaol is more effective than 6-gingerol and curcumin in inhibiting 12-O-tetradecanoylphorbol 13-acetate-induced tumor promotion in mice. Mol Nutr Food Res 54: 1296-1306.
11. Hu R, Zhou P, Peng YB, Xu X, Ma J, et al. (2012) 6-Shogaol induces apoptosis in human hepatocellular carcinoma cells and exhibits anti-tumor activity in vivo through endoplasmic reticulum stress. PLoS One 7: e39664.
12. Chen H, Lv L, Soroka D, Warin RF, Parks TA, et al. (2012) Metabolism of [6]-shogaol in mice and in cancer cells. Drug Metab Dispos 40: 742-753.
13. Constantino MG, Matias LGO, da Silva GVJ, Barbieri E, (1998) Stereoselective sodium borohydride reductions of cyclopentanones: influence of ceric chloride on the stereochemistry of reaction. Química Nava 21: 719-721.
14. Sowden JC, Oftedahl ML, Kirkland A, (1962) The addition of sodium methoxide to carbohydrate α-nitroolefins. Synthesis of 2-O-methyl-D-mannose and 2-O-methyl-D-ribose. J Org Chem 27: 1791-1793.
15. Toyota M, Asano T, Ihara M, (2005) Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement. Org Lett 7: 3929-3932.
16. Wiseman M, (2008) The second World Cancer Research Fund/American Institute for Cancer Research expert report. Food, nutrition, physical activity, and the prevention of cancer: a global perspective. Proc Nutr Soc 67: 253-256.
17. Karakaya S, (2004) Bioavailability of phenolic compounds. Crit Rev Food Sci Nutr 44: 453-464.
18. Key TJ Fruit and vegetables and cancer risk. Br J Cancer 104: 6-11.
19. Wild CP, Andersson C, O'Brien NM, Wilson L, Woods JA, (2001) A critical evaluation of the application of biomarkers in epidemiological studies on diet and health. Br J Nutr 86Suppl 1: S37-53.
20. Mosmann T, (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65: 55-63.