Skip to main content
PMC home page
Food Science and Biotechnology logoLink to Food Science and Biotechnology
. 2016 Feb 29;25(1):247–252. doi: 10.1007/s10068-016-0036-4

Molecular structure and anti-proliferative effect of galangin in HCT-116 cells: In vitro study

Ghassan Mohammad Sulaiman 1,✉
PMCID: PMC6049387  PMID: 30263264

Abstract

Galangin is a naturally occurring plant flavonoid with potential anticancer activity. In present work, the Becke three-parameter hybrid exchange functional method and the Lee-Yang-Parr correction functional methods were used to investigate the structural properties of galangin. The structure-activity relationship analysis has been performed to determine its antioxidant pharmacophore by using density functional theory method and quantum chemical calculations. The free radical scavenging activities of galangin were analyzed with the use of 2, 2-diphenyl-1-picrylhydrazyl and compared with Vitamin C as a control. Galangin decreased the cell proliferation rate in HCT-116 cells and showed concentration- and time-dependent response. Galangin significantly increase the inhibitory effect on HCT-116 clonogenicity and promotes cell cycle arrest at the G2/M or G1 phase, as confirmed by flow cytometry analysis.

Keywords: galangin, molecular structure, clonogenicity, cell cycle, HCT-116

References

  • 1.Formica J, Regelson W. Review of the biology of quercetin and related bioflavonoids. Food Chem. Toxicol. 1995;33:1061–1080. doi: 10.1016/0278-6915(95)00077-1. [DOI] [PubMed] [Google Scholar]
  • 2.Khan NA. Antioxidant and cancer. Scienc. 2002;2:38–43. [Google Scholar]
  • 3.Patel DK, Patel K, Gadewar M, Tahilyani V. Pharmacological and bioanalytical aspects of galangin-A concise report. Asian Pac. J. Trop. Biomed. 2012;2:S449–S455. doi: 10.1016/S2221-1691(12)60205-6. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 4.Knekt P, Jarvinen R, Seppanen R, Hellovaara M, Teppo L, Pukkala E, Aromaa A. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. Am. J. Epidemiol. 1997;146:223–230. doi: 10.1093/oxfordjournals.aje.a009257. [DOI] [PubMed] [Google Scholar]
  • 5.Birt DF, Hendrich S, Wang W. Dietary agents in cancer prevention: Flavonoids and isoflavonoids. Pharmacol. Therapeut. 2001;90:157–177. doi: 10.1016/S0163-7258(01)00137-1. [DOI] [PubMed] [Google Scholar]
  • 6.Neuhouser ML. Dietary flavonoids and cancer risk: Evidence from human population studies. Nutr. Cance. 2004;50:1–7. doi: 10.1207/s15327914nc5001_1. [DOI] [PubMed] [Google Scholar]
  • 7.Li BH, Tian WX. Presence of fatty acid synthase inhibitors in the rhizome of Alpinia officinarum hance. J. Enzym. Inhib. Med. Ch. 2003;18:349–356. doi: 10.1080/1475636031000118419. [DOI] [PubMed] [Google Scholar]
  • 8.Volpi N. Separation of flavonoids and phenolic acids from propolis by capillary zone electrophoresis. Electrophoresi. 2004;25:1872–1878. doi: 10.1002/elps.200405949. [DOI] [PubMed] [Google Scholar]
  • 9.Sulaiman GM, Al Sammarrae KW, Ad’hiah AH, Zucchetti M, Frapolli R, Bello E, Erba E, D'Incalci M, Bagnati R. Chemical characterization of Iraqi propolis samples and assessing their antioxidant potentials. Food Chem. Toxicol. 2011;49:2415–2421. doi: 10.1016/j.fct.2011.06.060. [DOI] [PubMed] [Google Scholar]
  • 10.Heo MY, Sohn SJ, Au WW. Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate. Mutat. Res. 2001;488:135–150. doi: 10.1016/S1383-5742(01)00054-0. [DOI] [PubMed] [Google Scholar]
  • 11.Cushnie TP, Lamb AJ. Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus. Phytomedicin. 2006;13:187–191. doi: 10.1016/j.phymed.2004.07.003. [DOI] [PubMed] [Google Scholar]
  • 12.Gwak J, Oh J, Cho M, Bae SK, Song IS, Liu KH, Jeong Y, Kim DE, Chung YH, Oh S. Galangin suppresses the proliferation of β-catenin response transcriptionpositive cancer cells by promoting adenomatous polyposis coli/Axin/glycogen synthase kinase-3β-independent β-catenin degradation. Mol. Pharmacol. 2011;79:1014–1022. doi: 10.1124/mol.110.069591. [DOI] [PubMed] [Google Scholar]
  • 13.Murray TJ, Yang X, Sherr DH. Growth of a human mammary tumor cell line is blocked by galangin, a naturally occurring bioflavonoid, and is accompanied by down-regulation of cyclins D3, E, and A. Breast Cancer Res. 2006;8:R17. doi: 10.1186/bcr1391. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 14.Tolomeo M, Grimaudo S, Di Cristina A, Pipitone RM, Dusonchet L, Meli M, Crosta L, Gebbia N, Invidiata FP, Titone L, Simoni D. Galangin increases the cytotoxic activity of imatinib mesylate in imatinib-sensitive and imatinibresistant Bcr-Abl expressing leukemia cells. Cancer Lett. 2008;265:289–297. doi: 10.1016/j.canlet.2008.02.025. [DOI] [PubMed] [Google Scholar]
  • 15.Li F, Awale S, Tezuka Y, Esumi H, Kadota S. Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells. J. Nat. Prod. 2010;73:623–627. doi: 10.1021/np900772m. [DOI] [PubMed] [Google Scholar]
  • 16.Kumar N, Mueen AKK, Dang R, Husain A. Antioxidant and antimicrobial activity of propolis from Tamil Nadu zone. J. Med. Plants Res. 2008;2:361–364. [Google Scholar]
  • 17.Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.02, Gaussian Inc. 2009. [Google Scholar]
  • 18.Naama JH, Alwan GH, Obayes HR, Al-Amiery AA, Al-Temimi AA, Kadhum AAH, Mohamad AB. Curcuminoids as antioxidants and theoretical study of stability of curcumin isomers in gaseous state. Res. Chem. Intermediat. 2013;39:4047–4059. doi: 10.1007/s11164-012-0921-2. [DOI] [Google Scholar]
  • 19.Obayes HR, Alwan GH, Al-Amiery AA, Kadhum AH. Mohamad^AB Thermodynamic and theoretical study of the preparation of new buckyballs from corannulene, coronene, and circulene. J. Nanomater. 2013;2013:1–8. doi: 10.1155/2013/451920. [DOI] [Google Scholar]
  • 20.Darzynkiewicz Z, Huang X. Analysis of cellular DNA content by flow cytometry. In: Coico R, editor. Current Protocols in Immunology. 2004. [DOI] [PubMed] [Google Scholar]
  • 21.Caltagirone S, Rossi C, Poggi A, Ranelletti FO, Natali PG, Brunetti M, Aiello FB, Piantelli M. Flavonoids apigenin and quercetin inhibit melanoma growth and metastatic potential. Int. J. Cance. 2000;87:595–600. doi: 10.1002/1097-0215(20000815)87:4<595::AID-IJC21>3.0.CO;2-5. [DOI] [PubMed] [Google Scholar]
  • 22.Kobayashi T, Nakata T, Kuzumaki T. Effect of flavonoids on cell cycle progression in prostate cancer cells. Cancer Lett. 2002;176:17–23. doi: 10.1016/S0304-3835(01)00738-8. [DOI] [PubMed] [Google Scholar]
  • 23.Kelke M, Jacob C, Dicato M, Diederich M. Potential of the dietary antioxidants resveratrol and curcumin in prevention and treatment of hematologic malignancies. Molecule. 2010;15:7035–7074. doi: 10.3390/molecules15107035. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 24.Woo HD, Kim J. Dietary flavonoid intake and risk of stomach and colorectal cancer. World J. Gastroentero. 2013;19:1011–1019. doi: 10.3748/wjg.v19.i7.1011. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 25.Tang SZ, Kerry JP, Sheehan D, Buckley DJ. Antioxidative mechanisms of tea catechins in chicken meat systems. Food Chem. 2002;76:45–51. doi: 10.1016/S0308-8146(01)00248-5. [DOI] [Google Scholar]
  • 26.Gulcin I. Antioxidant properties of resveratrol: A structure activity insight. Innov. Food Sci. Emerg. 2010;11:210–218. doi: 10.1016/j.ifset.2009.07.002. [DOI] [Google Scholar]
  • 27.Sulaiman GM, Al-Amiery AA, Bagnati R. Theoretical, antioxidant and cytotoxic activities of caffeic acid phenethyl ester and chrysin. Int. J. Food Sci. Nutr. 2014;65:101–105. doi: 10.3109/09637486.2013.832174. [DOI] [PubMed] [Google Scholar]
  • 28.Sroka Z, Cisowski W. Hydrogen peroxide scavenging, antioxidant and antiradical activity of some phenolic acids. Food Chem. Toxicol. 2003;41:753–758. doi: 10.1016/S0278-6915(02)00329-0. [DOI] [PubMed] [Google Scholar]
  • 29.Gregoris E, Stevanato R. Correlations between polyphenolic composition and antioxidant activity of Venetian propolis. Food Chem. Toxico. 2010;48:76–82. doi: 10.1016/j.fct.2009.09.018. [DOI] [PubMed] [Google Scholar]
  • 30.Kumazawa S, Hamasaka T, Nakayama T. Antioxidant activity of propolis of various geographic origins. Food Chem. 2004;84:329–339. doi: 10.1016/S0308-8146(03)00216-4. [DOI] [Google Scholar]
  • 31.Shimoi K, Masuda S, Furugori M, Esaki S, Kinae N. Radioprotective effect of antioxidative flavonoids in gamma-ray irradiated mice. Carcinogenesi. 1994;15:2669–2672. doi: 10.1093/carcin/15.11.2669. [DOI] [PubMed] [Google Scholar]
  • 32.Lien EJ, Ren S, Bui HH, Wang R. Quantitative structure-activity relationship analysis of phenolic antioxidants. Free Radical Bio. Med. 1999;26:285–294. doi: 10.1016/S0891-5849(98)00190-7. [DOI] [PubMed] [Google Scholar]
  • 33.Tsai YD, Chen HJ, Hsu HF, Lu K, Liang CL, Liliang PC, Wang KW, Wang HK, Wang CP, Houng JY. Luteolin inhibits proliferation of human glioblastoma cells via induction of cell cycle arrest and apoptosis. J. Taiwan Inst. Chem. E. 2013;44:837–845. doi: 10.1016/j.jtice.2013.03.005. [DOI] [Google Scholar]
  • 34.Yun-xia XU, Xin-huai Z. Chinese Pharmaceut. J. 2013. In vitro effects of galangin on cell proliferation, cycle progression and apoptosis of a human gastric cancer SGC-7901 cells. [Google Scholar]
  • 35.Moon YJ, Wang X, Morris ME. Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism. Toxicol. In Vitro. 2006;20:187–210. doi: 10.1016/j.tiv.2005.06.048. [DOI] [PubMed] [Google Scholar]
  • 36.Quadri SA, Qadri AN, Hahn ME, Mann KK, Sherr DH. The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis. Mol. Pharmacol. 2000;58:515–525. [Google Scholar]

Articles from Food Science and Biotechnology are provided here courtesy of Springer

RESOURCES