The isolation of soyasaponins by fractional precipitation, solid phase extraction, and low pressure liquid chromatography

References

• Ahmad VU, Atta-ur-Rahman. Handbook of Natural Products Data Vol 2 Pentacyclic triterpenoids. Elsevier, Amsterdam, Holland 1994; 138, 268
   Google Scholar
• Berhow MA, Cantrell CL, Dural SM, Dobbins TA, Maynes J, Vaughn SF. Analysis and quantitative determination of group B saponins in processed soybean products. Phytochem Anal 2002; 13: 343–348
   PubMed Web of Science ®Google Scholar
• Boehlert JP. Regulatory aspects: ICH and Pharmacopoeial Perspectives. Progress in Pharmaceutical and Biomedical analysis 4: Identification and determination of impurities in drugs, G Sandor. Elsevier, Amsterdam, Holland 2000; 48–66
   Google Scholar
• Burrows JC, Price KR, Fenwick GR. Soyasaponin IV, an additional monodesmosidic saponin isolated from soybean. Phytochemistry 1987; 26: 1214–1215
   Google Scholar
• Calvert GD, Blight L, Illman RJ, Topping DR, Potter JD. A trial of the effects of soyabean flour & soyabean saponins on plasma lipids, faecal bile acids & neutral sterols in hypercholesterolemic men. Br J Nutr 1981; 45: 277–281
   PubMedGoogle Scholar
• Cui B, Inoue J, Takeshita T, Kinjo J, Nohara T. Triterpene glycosides from the seeds of astragulus sinicus L. Chem Pharm Bull 1992; 40: 3330–3333
   PubMedGoogle Scholar
• Fuzzati N, Pace R, Papeo G, Peterlongo F. Identification of soyasaponins by liquid chromatography-mass thermospray. J Chrom A 1997; 777: 233–238
   Google Scholar
• Gu L, Tao G, Gu W, Prior RL. Determination of soyasaponins in soy with LC-MS following structural unification by partial alkaline degradation. J Agric Food Chem 2002; 50: 6951–6959
   PubMed Web of Science ®Google Scholar
• Gurfinkel DM, Rao AV. Determination of saponins in legumes by direct densitometry. J Agric Food Chem 2002; 50: 426–430
   Google Scholar
• Hahn-Deinstrop E. Applied Thin-Layer Chromatography: Best Practice and Avoidance of Mistakes. Wiley-Vch, WeinheimGermany 2000; 218–224
   Google Scholar
• Hosny M, Rosazza JPN. Novel isoflavone, cinnamic acid, and triterpenoid glycosides in soybean molasses. J Nat Prod 1999; 62: 853–858
   PubMed Web of Science ®Google Scholar
• Hosny M, Rosazza JPN. New isoflavone and triterpene glycosides from soybeans. J Nat Prod 2002; 65: 805–813
   PubMed Web of Science ®Google Scholar
• Hostettman K, Marston A. Saponins. Cambridge University Press, Cambridge, England 1995
   Google Scholar
• Hu J, Lee S-O, Hendrich S, Murphy PA. Quantification of the group B soyasaponins by high-performance liquid chromatography. J Agric Food Chem 2002; 50: 2587–2594
   PubMed Web of Science ®Google Scholar
• Ikeda T, Udayama M, Okawa M, Arao T, Kinjo J, Nohara T. Partial hydrolysis of soyasaponin I and the hepatoprotective effects of the hydrolytic products. Study of the structure-hepatoprotective relationship of soyasapogenol B analogs. Chem Pharm Bull 1998; 46: 359–361
   Google Scholar
• Ireland PA, Driedzic SZ. Effect of hydrolysis on sapogenin release in soya. J Agric Food Chem 1986; 34: 1037–1041
   Google Scholar
• Kinjo J, Hatakeyama M, Udayama M, Tsutanaga Y, Yamashita M, Toshihiro N, Yashiki Y, Okubo K. HPLC profile analysis of oleanene-glucuronides in several edible beans. Biosci Biotechnol Biochem 1998b; 62: 429–433
   PubMed Web of Science ®Google Scholar
• Kinjo J, Imagire M, Udayama M, Arao T, Nohara T. Structure-hepatoprotective relationships study of soyasaponins I–IV having soyasapogenol B as aglycone. Planta Med 1998a; 64: 233–236
   PubMed Web of Science ®Google Scholar
• Kitagawa I, Saito M, Taniyama T, Yashikawa M. Saponin and Sapogenol XXXVIII: Structure of soyasaponin A2, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 1985a; 33: 598–608
   Web of Science ®Google Scholar
• Kitagawa I, Saito M, Taniyama T, Yoshikawa M. Saponin and sapogenol XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 1985b; 33: 1069–1076
   Web of Science ®Google Scholar
• Kitagawa I, Taniyama T, Nagahama Y, Okuba K, Yamauchi F, Yoshikawa M. Saponin and sapogenol XLII. Structures of acetyl-soyasaponins A1, A2, and A3, astringent partially acetylated bisdesmosides of soyasapogenol A, from American soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 1988; 36: 2819–2828
   Web of Science ®Google Scholar
• Kitagawa I, Yoshikawa M, Hayashi T, Taniyama T. Quantitative determination of soyasaponins in soybeans of various origins and soybean products by means of high performance liquid chromatography. Yakugaku Zasshi 1984b; 104: 275–279
   PubMed Web of Science ®Google Scholar
• Kitagawa I, Yoshikawa M, Hayashi T, Taniyama T. Characterization in soybeans of various origins and quantitative analysis of soyasaponins by gas liquid chromatography. Yakagaku Zasshi 1984a; 104: 162–168
   PubMedGoogle Scholar
• Kitagawa I, Yoshikawa M, Yosioka I. Saponin and sapogenol XIII: Structures of three soybean saponins: soyasaponin I, soyasaponin II, and soyasaponin III. Chem Pharm Bull. 1976; 24: 121–129
   Web of Science ®Google Scholar
• Nash AM, Eldridge AC, Wolf WJ. Fractionation and characterization of alcohol extractables associated with soybean protein. Nonprotein components. J Agric Food Chem 1967; 15: 102–108
   Google Scholar
• Oleszek W. Solid phase extraction-fractionation of alfalfa saponins. J Sci Food Agric 1988; 44: 43–49
   Web of Science ®Google Scholar
• Philbrick DJ, Bureau DP, Collins FW, Holub BJ. Evidence that soyasaponin Bb retards disease progression in a murine model of polycystic disease. Kidney Int 2003; 63: 1230–1239
   Google Scholar
• Potter JD, Illman RJ, Calvert GD, Oakenfull DG, Topping DL. Soyasaponins, plasma lipids, lipoproteins & fecal bile acids: A double blind cross-over study. Nutr Rep Int 1980; 22: 521–528
   Google Scholar
• Price KR, Curl CL, Fenwick GR. The saponin content and sapogenol composition of the seed of 13 varieties of legume. J Sci Food Agric 1986; 37: 1185–1191
   Web of Science ®Google Scholar
• Rao AV, Gurfinkel DM. The bioactivity of soyasaponins. Soy and health 2002, K Descheemaeker, I Debruyne. Garant Publishers, Antwerp-ApeldoornBelgium 2003; 137–147
   Google Scholar
• Rao AV, Gurfinkel DM. Dietary saponins and human health. Saponins in Food, Foodstuffs and Medicinal Plants: Proceeding of the Phytochemical Society of Europe, W Oleszek, A Marston. Kluwer Academic Publishers, DordrechtNetherlands 2000; 255–270
   Google Scholar
• Reinli K, Block G. Phytoestrogen content of foods-a compendium of literature calues. Nutr Cancer 1996; 26: 123–48
   PubMed Web of Science ®Google Scholar
• Row LR, Rukmini C. Chemistry of saponins. Part I. Saponin of sapindus mukorossi Gaertn. Indian J Chem 1966; 4: 36–38
   Google Scholar
• Shiraiwa M, Kudo S, Shimoyamada M, Harada K, Okubo K. Composition and structure of ‘Group A saponin’ in soybean seed. Agric Biol Chem 1991a; 55: 315–322
   Web of Science ®Google Scholar
• Shiraiwa M, Harada K, Okubo K. Composition and structure of ‘group B saponin’ in soybean seed. Agric Bio Chem 1991b; 55: 911–7
   PubMed Web of Science ®Google Scholar
• Taniyama T, Nagahana Y, Yoshikawa M, Kitagawa I. Saponin and sapogenol XLIII. Acetyl-soyasaponin A4, A5, A6, new astringent bisdesmosides of soyasapogenol A, from Japanese soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 1988; 36: 2829–2839
   Google Scholar
• Tava A, Mella M, Bialy Z, Jurzysta M. Stability of saponins in alcoholic solutions: ester formation as artifacts. J Agric Food Chem 2003; 51: 1797–1800
   PubMed Web of Science ®Google Scholar
• Wolf WJ, Thomas BW. Ion-exchange chromatography of soybean saponins. J Chrom 1971; 56: 281–293
   Google Scholar
• Wolf WJ, Thomas BW. Thin layer and anion exchange chromatography of soybean saponins. J AO C S 1970; 47: 86–90
   Web of Science ®Google Scholar
• Wu CY, Hsu CC, Chen ST, Tsai YC. Soyasaponin I, a potent and specific sialyltransferase inhibitor. Biochem Biophys Res Comm 2001; 284: 466–469
   Google Scholar
• Yoshikoshi M, Yoshiki Y, Okubo K, Seto J, Sasaki Y. Prevention of hydrogen peroxide damage by soybean saponins to mouse fibroblasts. Planta Med 1996; 62: 252–255
   PubMedGoogle Scholar