Effects of solvent polarity and acidity on the extraction efficiency of isoflavones from soybeans (Glycine max)

Soy isoflavones have been correlated with beneficial health effects. The predominant chemical forms of isoflavones present may affect their biological activities. Choosing the solvent system that can accurately quantify the amounts of individual isoflavones present in these products is paramount. Our objectives were to compare frequently used solvent systems and to evaluate the effects of polarity and acidity on the recovery of isoflavones from soybeans. Isoflavones were extracted from pulverized Manokin soybeans using six solvent systems, which are the combinations of three polarity levels (83% acetonitrile, 80% methanol, and 58% acetonitrile) and two acidity levels (nonacidified and acidified). The pulverized soybean was stirred for 2 h in each solvent system before filtration and concentration using rotary evaporation. The extract was resuspended in 16% acetonitrile and analyzed by high-performance liquid chromatography. Recoveries of pure standards were evaluated with all solvent systems. Solvents with a higher polarity extracted a significantly higher amount of total isoflavones. For individual isoflavones, 58% acetonitrile (highest polarity) extracted either the highest amounts or no less than other solvents, while 83% acetonitrile (lowest polarity) extracted either the lowest amounts or no more than other solvents except for the aglycone form. Acidification significantly reduced the recovery of the malonylglucoside form and the total isoflavones. The recovery study revealed that acidification favored the chemical transformations of isoflavones during the extraction. Among the six solvent systems examined, 58% acetonitrile aqueous solution without acid was the best for extraction of isoflavones from soybeans.