Preparative chromatographic purification and surfactant properties of individual soyasaponins from soy hypocotyls

Food Chemistry

Volumn 101, Issue 1, 2007, Pages 324-333

  Decroos, Karel ^a   Vincken, Jean Paul ^b   van Koningsveld, Gerrit A ^b   Gruppen, Harry ^b   Verstraete, Willy ^a  

^a GHENT UNIVERSITY   (Belgium)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

CMC; Reversed phase preparative chromatography; Soyasaponin; Surface tension

Indexed keywords

ACETIC ACID DERIVATIVE; CHOLIC ACID; POLYSORBATE 80; SAPONIN DERIVATIVE; SOYASAPONIN AB; SOYASAPONIN ALPHAG; SOYASAPONIN BA; SOYASAPONIN BB; SOYASAPONIN BETAG; SUGAR; SURFACTANT; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CONJUGATION; DRUG PURIFICATION; MICELLE; NONHUMAN; PLANT GROWTH; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOYBEAN; SURFACE TENSION;

EID: 33746885850     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2006.01.041     Document Type: Article

References (47)

1. Bae E.A., Han M.J., Choo M.K., Park S.Y., and Kim D.H. Metabolism of 20(S)- and 20(R)-ginsenoside R-g3 by human intestinal bacteria and its relation to in vitro biological activities. Biological & Pharmaceutical Bulletin 25 1 (2002) 58-63
2. Berhow M.A., Cantrell C.L., Duval S.M., Dobbins T.A., Maynes J., and Vaughn S.F. Analysis and quantitative determination of group B saponins in processed soybean products. Phytochemical Analysis 13 6 (2002) 343-348
3. Berhow M.A., Wagner E.D., Vaughn S.F., and Plewa M.J. Characterization and antimutagenic activity of soybean saponins. Mutation Research-Fundamental and Molecular Mechanisms of Mutagenesis 448 1 (2000) 11-22
4. Coello A., Meijide F., Nunez E.R., and Tato J.V. Aggregation behavior of bile salts in aqueous solution. Journal of Pharmaceutical Sciences 85 1 (1995) 9-15
5. Decroos K., Vincken J.-P., Heng L., Bakker R., Gruppen H., and Verstraete W. Simultaneous quantification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one-conjugated soyasaponins using reversed-phase high-performance liquid chromatography with evaporative light scattering detection. Journal of Chromatography A 1072 2 (2005) 185-193
6. Ellington A.A., Berhow M., and Singletary K.W. Induction of macroautophagy in human colon cancer cells by soybean B-group triterpenoid saponins. Carcinogenesis 26 1 (2005) 159-167
7. Fenwick D.E., and Oakenfull D. Saponin content of food plants and some prepared foods. Journal of Science of Food and Agriculture 34 (1983) 186-191
8. Francis G., Kerem Z., Makkar H.P.S., and Becker K. The biological action of saponins in animal systems: a review. British Journal of Nutrition 88 6 (2002) 587-605
9. 1). Nippon Nigei Kagaku Kaishi 64 (1990) 901-906
10. Gu L.W., Tao G.J., Gu W.Y., and Prior R.L. Determination of soyasaponins in soy with LC-MS following structural unification by partial alkaline degradation. Journal of Agricultural and Food Chemistry 50 24 (2002) 6951-6959
11. Gurfinkel D.M., and Rao A.V. Soyasaponins: The relationship between chemical structure and colon anticarcinogenic activity. Nutrition and Cancer - An International Journal 47 1 (2003) 24-33
12. Haque M.E., Das A.R., and Moulik S.P. Mixed micelles of sodium deoxycholate and polyoxyethylene sorbitan monooleate (Tween 80). Journal of Colloid and Interface Science 217 1 (1999) 1-7
13. Heng, L., Vincken, J.-P., Hoppe, K., van Koningsveld, G.A., Decroos, K., Gruppen, H., et al. Stability of pea DDMP saponin and the mechanism of its decomposition. Food Chemistry [in press], doi:10.1016/j.foodchem.2005.07.045.
14. Hu J., Lee S.O., Hendrich S., and Murphy P.A. Quantification of the group B soyasaponins by high-performance liquid chromatography. Journal of Agricultural and Food Chemistry 50 9 (2002) 2587-2594
15. Huibers P.D.T., Lobanov V.S., Katritzky A.R., Shah D.O., and Karelson M. Prediction of critical micelle concentration using a quantitative structure-property relationship approach. Journal of Colloid and Interface Science 187 (1997) 113-120
16. Kinjo J., Imagire M., Udayama M., Arao T., and Nohara T. Studies on the hepatoprotective drugs part 3 - studies on the constituents of the leguminous plants part 56 - structure-hepatoprotective relationships study of soyasaponins I-IV having soyasapogenol B as aglycone. Planta Medica 64 3 (1998) 233-236
17. Kitagawa I., Taniyama T., Nagahama Y., Okubo K., Yamauchi F., and Yoshikawa M. Saponin and sapogenol .42. Structures of acetyl-soyasaponin-A1, acetyl-soyasaponin-A2, and acetyl-soyasaponin-A3, astringent partially acetylated bisdesmosides of soyasapogenol-a, from American soybean, the seeds of glycine-max merrill. Chemical & Pharmaceutical Bulletin 36 8 (1988) 2819-2828
18. Kitagawa I., Wang H.K., Taniyama T., and Yoshikawa M. Saponin and sapogenol .41. Reinvestigation of the structures of soyasapogenol-a, soyasapogenol-B, and soyasapogenol-E, oleanene-sapogenols from soybean - structures of soyasap1onin-I, soyasaponin-Ii, and soyasaponin-Iii. Chemical & Pharmaceutical Bulletin 36 1 (1988) 153-161
19. Kudou S., Tonomura M., Tsukamoto C., Uchida T., Sakabe T., Tamura N., and Okubo K. Isolation and structural elucidation of Ddmp-conjugated soyasaponins as genuine saponins from soybean seeds. Bioscience Biotechnology and Biochemistry 57 4 (1993) 546-550
20. Kudou S., Tonomura M., Tsukamoto C., Uchida T., Yoshikoshi M., and Okubo K. Structural elucidation and physiological properties of genuine soybean saponins. In: Hang M.T. (Ed). Food phytochemicals for cancert prevention I vol. 546 (1994), American Chemical Society, Washington, DC 340-348
21. Lasztity R., Hidevegi M., and Bata A. Saponins in food. Food Reviews International 14 4 (1998) 371-390
22. Lee S.O., Simons A.L., Murphy P.A., and Hendrich S. Soyasaponins lowered plasma cholesterol and increased fecal bile acids in female golden Syrian hamsters. Experimental Biology and Medicine 230 7 (2005) 472-478
23. Marciani D.J., Reynolds R.C., Pathak A.K., Finley-Woodman K., and May R.D. Fractionation structural studies and immunological characterization of the semi-synthetic Quillaja saponins derivative GPI-0100. Vaccine 21 25-26 (2003) 3961-3971
24. Milgate J., and Roberts D.C.K. The nutritional and biological significance of saponins. Nutrition Research 15 8 (1995) 1223-1249
25. Mitra S., and Dungan S.R. Micellar properties of quillaja saponin. 1. Effects of temperature salt and pH on solution properties. Journal of Agricultural and Food Chemistry 45 5 (1997) 1587-1595
26. Mitra S., and Dungan S.R. Micellar properties of quillaja saponin. 2. Effect of solubilized cholesterol on solution properties. Colloids and Surfaces B - Biointerfaces 17 2 (2000) 117-133
27. Mitra S., and Dungan S.R. Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants. Journal of Agricultural and Food Chemistry 49 1 (2001) 384-394
28. Oakenfull D. Saponins in food - a review. Food Chemistry 7 (1981) 19-40
29. Oakenfull D. Aggregation of saponins and bile acids in aqueous solution. Australian Journal of Chemistry 39 (1986) 1671-1683
30. Oda K., Matsuda H., Murakami T., Katayama S., Ohgitani T., and Yoshikawa M. Adjuvant and haemolytic activities of 47 saponins derived from medicinal and food plants. Biological Chemistry 381 1 (2000) 67-74
31. Oda K., Matsuda H., Murakami T., Katayama S., Ohgitani T., and Yoshikawa M. Relationship between adjuvant activity and amphipathic structure of soyasaponins. Vaccine 21 17-18 (2003) 2145-2151
32. Philbrick D.J., Bureau D.P., Collins F.W., and Holub B.J. Evidence that soyasaponin B-b retards disease progression in a murine model of polycystic kidney disease. Kidney International 63 4 (2003) 1230-1239
33. Pillion D.J., Amsden J.A., Kensil C.R., and Recchia J. Structure-function relationship among Quillaja saponins serving as excipients for nasal and ocular delivery of insulin. Journal of Pharmaceutical Sciences 85 5 (1996) 518-523
34. Rao A.V., and Sung M.K. Saponins as anticarcinogens. Journal of Nutrition 125 (1995) 717S-724S
35. Roda A., Hofmann A.F., and Mysels K.J. The Influence of bile-salt structure on self-association in aqueous-solutions. Journal of Biological Chemistry 258 10 (1983) 6362-6370
36. Rowlands J.C., Berhow M.A., and Badger T.M. Estrogenic and antiproliferative properties of soy sapogenols in human breast cancer cells in vitro. Food and Chemical Toxicology 40 12 (2002) 1767-1774
37. Sasaki K., Minowa N., Kuzuhara H., Nishiyama S., and Omoto S. Derivatization of soyasapogenol A and their hepatoprotective activities. Bioorganic & Medicinal Chemistry Letters 8 6 (1998) 607-612
38. Shiraiwa M., Harada K., and Okubo K. Composition and content of saponins in soybean seed according to variety, cultivation year and maturity. Agricultural and Biological Chemistry 55 2 (1991) 323-331
39. Shiraiwa M., Yamauchi F., Harada K., and Okubo K. Inheritance of group-a saponin in soybean seed. Agricultural and Biological Chemistry 54 6 (1990) 1347-1352
40. Small D.M. The physical chemistry of cholanic acids. In: Nair P.P., and Kritchevsky D. (Eds). The bile acids Vol. 1 (1971), Plenum Press, New York 249
41. Sparg S.G., Light M.E., and van Staden J. Biological activities and distribution of plant saponins. Journal of Ethnopharmacology 94 2-3 (2004) 219-243
42. Wang Z.W., Gu M.Y., and Li G.Z. Surface properties of gleditsia saponin and synergisms of its binary system. Journal of Dispersion Science and Technology 26 3 (2005) 341-347
43. Yeom I.T., Ghosh M.M., Cox C.D., and Robinson K.G. Micellar solubilization of polynuclear aromatic hydrocarbons in coal tar-contaminated soils (vol 29, pg 3015, 1995). Environmental Science & Technology 30 6 (1996) 2104
44. Yoshiki Y., Kudou S., and Okubo K. Relationship between chemical structures and biological activities of triterpenoid saponins from soybean. Bioscience Biotechnology and Biochemistry 62 12 (1998) 2291-2299
45. Yoshiki Y., Takagi S., Watanabe M., and Okubo K. Fractionation of soybean functional glycosides from soy-waste based on the chemical reaction of soyasaponin [beta] g. Food Chemistry 93 4 (2005) 591-597
46. Zhang Z.Z., Koike K., Jia Z.H., Nikaido T., Guo D., and Zheng J.H. Triterpenoidal saponins from Gleditsia sinensis. Phytochemistry 52 4 (1999) 715-722
47. Zheng Z., and Obbard J.P. Evaluation of an elevated non-ionic surfactant critical micelle concentration in a soil/aqueous system. Water Research 36 10 (2002) 2667-2672