International Journal of Oral Biology

The Korean Academy of Oral Biology (대한구강생물학회)
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Identification of Anthocyanin from The Extract of Soybean Seedcoat

  • Park, Sun-Mi (Department of Pharmacology and Dental Therapeutics, School of Dentistry, Chosun University) ;
  • Kim, Ji-Na (Department of Pharmacology and Dental Therapeutics, School of Dentistry, Chosun University) ;
  • Dung, Tran-Huu (Department of Analysis, Faculty of Pharmacy, Hue Medicine and Pharmacy University) ;
  • Do, Le Thanh (Department of Pharmacology and Dental Therapeutics, School of Dentistry, Chosun University) ;
  • Thu, Do Thi Anh (Department of Pharmacology and Dental Therapeutics, School of Dentistry, Chosun University) ;
  • Sung, Mi-Kyung (Department of Food & Nutrition, College of Human Ecology, Sookmyung University) ;
  • Kim, Jong-Sang (Department of Animal Science and Biotechnology, College of Agriculture, Kyungpook National University) ;
  • Yoo, Hoon (Department of Pharmacology and Dental Therapeutics, School of Dentistry, Chosun University)
  • Received : 2011.03.09
  • Accepted : 2011.06.10
  • Published : 2011.06.30
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Abstract

Anthocyanins are naturally occuring phytochemicals and the main components of the coloring of plants, flowers and fruits. They are known to elicit antioxidative, anti-inflammatory and cancer preventive activity. In this study, we investigated anthocyanins in black / yellow soybean seedcoats using different methods of detection - thin layer chromatography (TLC), capillary zone electrophoresis (CZE) and HPLC analysis. The anthocyanins in soybean seedcoats were extracted by five independent methods of extraction and the aglycons (anthocyanidins) of the corresponding anthocyanins were prepared by acid mediated hydrolysis. The anthocyanin / anthocyanidin in black soybean seedcoat showed characteristic TLC mobility, CZE electrophoretic retention and HPLC migration time while little of anthocyanins were detected from yellow soybean seedcoat. The extracted anthocyanins showed pH dependent retention time in CZE and spectral change in UV-Vis spectrum. HPLC analysis of the hydrolyzed extract of black soybean seedcoat identified the presence of four anthocyanidins. The major anthocyanin in black soybean seedcoat was cyanin (cyanidin-3-O-glucoside), with the relative order of anthocyanidin in cyanidin > delphinidin > petunidin > pelargonidin.

Keywords

References

  1. Bin Hafeez B, Asim M, Siddiqui IA, Adhami VM, Murtaza I, Mukhtar H. Delphinidin, a dietary anthocyanidin in pigmented fruits and vegetables: a new weapon to blunt prostate cancer growth. Cell Cycle. 2008;7:3320-6. https://doi.org/10.4161/cc.7.21.6969
  2. Choung MG, Baek IY, Kang ST, Han WY, Shin DC, Moon HP, Kang KH. Isolation and determination of anthocyanins in seed coats of black soybean (Glycine max (L.) Merr.). J Agric Food Chem. 2001;49:5848-51. https://doi.org/10.1021/jf010550w
  3. Cvorovic J, Tramer F, Granzotto M, Candussio L, Decorti G, Passamonti S. Oxidative stress-based cytotoxicity of delphinidin and cyanidin in colon cancer cells. Arch Biochem Biophys. 2010;501:151-7. https://doi.org/10.1016/j.abb.2010.05.019
  4. Fernandes I, Faria A, Azevedo J, Soares S, Calhau C, De Freitas V, Mateus N. Influence of anthocyanins, derivative pigments and other catechol and pyrogallol-type phenolics on breast cancer cell proliferation. J Agric Food Chem. 2010;58:3785-92. https://doi.org/10.1021/jf903714z
  5. Hui C, Bin Y, Xiaoping Y, Long Y, Chunye C, Mantian M, Wenhua L. Anticancer activities of an anthocyanin-rich extract from black rice against breast cancer cells in vitro and in vivo. Nutr Cancer. 2010;62:1128-36. https://doi.org/10.1080/01635581.2010.494821
  6. Hyun JW, Chung HS. Cyanidin and Malvidin from Oryza sativa cv. Heugjinjubyeo mediate cytotoxicity against human monocytic leukemia cells by arrest of G(2)/M phase and induction of apoptosis. J Agric Food Chem. 2004;52:2213-7. https://doi.org/10.1021/jf030370h
  7. Koide T, Hashimoto Y, Kamei H, Kojima T, Hasegawa M, Terabe K. Antitumor effect of anthocyanin fractions extracted from red soybeans and red beans in vitro and in vivo. Cancer Biother Radiopharm. 1997;12:277-80.
  8. Lee JH, Kang NS, Shin SO, Shin SH, Lim SG, Suh DY, Baek IY, Park KY, Ha TJ. Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis. Food Chemistry. 2009;112:226-231. https://doi.org/10.1016/j.foodchem.2008.05.056
  9. Lee MH, Kim MM, Kim JK, Kim DK, Kim HR, Kim HJ, Kim CS. Ethanol Extracts of Angelica decursiva Induces Apoptosis in Human Oral Cancer Cells. International Journal of Oral Biology. 2010;35:215-20.
  10. Lee YH, Jung JE, Lee JC, Moon HJ, Lee NH, Jhee EJ, Yi HK. The enhancement of apoptosis by combined with proteasome inhibitor and DNA synthetic inhibitor in oral cancer. International Journal of Oral Biology. 2008;33:25-31.
  11. Lin YC, Chou CC. Effect of heat treatment on total phenolic and anthocyanin contents as well as antioxidant activity of the extract from Aspergillus awamori-fermented black soybeans, a healthy food ingredient. Int J Food Sci Nutr. 2009;60:627-36. https://doi.org/10.3109/09637480801992492
  12. Matsunaga N, Tsuruma K, Shimazawa M, Yokota S, Hara H. Inhibitory actions of bilberry anthocyanidins on angiogenesis. Phytother Res. 2010;24 Suppl 1:S42-7. https://doi.org/10.1002/ptr.2895
  13. Meiers S, Kemeny M, Weyand U, Gastpar R, von Angerer E, Marko D. The anthocyanidins cyanidin and delphinidin are potent inhibitors of the epidermal growth-factor receptor. J Agric Food Chem. 2001;49:958-62. https://doi.org/10.1021/jf0009100
  14. Saenz-Lopez R, Fernandez-Zurbano P, Tena MT. Development and validation of a capillary zone electrophoresis method for the quantitative determination of anthocyanins in wine. J Chromatogr A. 2003;990:247-58. https://doi.org/10.1016/S0021-9673(02)02006-X
  15. Shin DY, Lee WS, Lu JN, Kang MH, Ryu CH, Kim GY, Kang HS, Shin SC, Choi YH. Induction of apoptosis in human colon cancer HCT-116 cells by anthocyanins through suppression of Akt and activation of p38-MAPK. Int J Oncol. 2009;35:1499-504.
  16. Slavin M, Kenworthy W, Yu LL. Antioxidant properties, phytochemical composition, and antiproliferative activity of Maryland-grown soybeans with colored seed coats. J Agric Food Chem. 2009;57:11174-85. https://doi.org/10.1021/jf902609n
  17. Stoner GD, Wang LS, Seguin C, Rocha C, Stoner K, Chiu S, Kinghorn AD. Multiple berry types prevent N-nitrosomethylbenzylamine- induced esophageal cancer in rats. Pharm Res. 2010;27:1138-45. https://doi.org/10.1007/s11095-010-0102-1
  18. Thomasset S, Teller N, Cai H, Marko D, Berry DP, Steward WP, Gescher AJ. Do anthocyanins and anthocyanidins, cancer chemopreventive pigments in the diet, merit development as potential drugs? Cancer Chemother Pharmacol. 2009;64:201- 11. https://doi.org/10.1007/s00280-009-0976-y
  19. Yun JM, Afaq F, Khan N, Mukhtar H. Delphinidin, an anthocyanidin in pigmented fruits and vegetables, induces apoptosis and cell cycle arrest in human colon cancer HCT116 cells. Mol Carcinog. 2009;48:260-70. https://doi.org/10.1002/mc.20477