Abstract

The isoflavone changes occurring in mature soybeans during food processing have been well studied, but less information is available on the changes in immature soybeans during thermal processing. This study aimed to determine the effect of thermal processing by dry- or wet-heating on the changes in the isoflavone profiles of immature and mature soybeans. In the malonylglycoside forms of isoflavone, their deglycosylation was more severe after wet-heating than after dry-heating regardless of the soybean maturity. The malonyl forms of isoflavones in the immature seeds were drastically degraded after a short wet-heating process. In the acetylglycoside forms of isoflavone, dry-heating produced relatively low amounts of the acetyl types in the immature soybeans compared with those in the mature soybeans. These results were explained by the content of acetyldaidzin being relatively less changed after dry-heating immature soybeans but increasing four to five times in the mature soybeans. More of the other types of acetylglycoside were produced by dry-heating soybeans regardless of their maturity. Acetylgenistin in wet-heating was a key molecule because its content was unchanged in the immature soybeans during processing but increased in the mature soybeans. This determined the total acetylglycoside content after wet-heating. In contrast, most of the acetyl forms of isoflavone were produced after 90 to 120 min of dry-heating regardless of the seed maturity. It can be suggested that the pattern of isoflavone conversion was significantly affected by the innate water content of the seeds, with a lower water content in the mature soybeans leading to the greater production of acetyl isoflavones regardless of the processing method even if only applied for a relatively short time. The results suggested that the isoflavone conversion in the immature soybeans mainly follows the wet-heating process and can be promoted in the application of stronger processing.

Highlights

  • Soybeans (Glycine max L.) are one of the most widely consumed legumes in the world.As well as their main role in providing protein, carbohydrates, and oil, soybeans are a rich source of phytochemicals, isoflavones [1,2]

  • Significant differences between experimental treatments were evaluated using Tukey’s student range test, with a significance level defined at p < 0.05. This is the first study to compare the patterns of isoflavone changes between soybeans at two maturity levels after thermal processing

  • The patterns of the isoflavone changes in the soybeans depended significantly on the soybean maturity and the processing method, which affected the decarboxylation of malonylglycoside or the deesterification of acetylglycoside isoflavones

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Summary

Introduction

Soybeans (Glycine max L.) are one of the most widely consumed legumes in the world As well as their main role in providing protein, carbohydrates, and oil, soybeans are a rich source of phytochemicals, isoflavones [1,2]. The 12 major isoflavones in soybeans can be classified into four main forms: aglycones (daidzein, glycitein, and genistein); β-glycosides (daidzin, glycitin, and genistin); acetylglycosides (acetyldaidzin, acetylglycitin, and acetylgenistin); and malonylglycosides (malonyldaidzin, malonylglycosides, and malonylgenistin) [4,5]. Of these isoflavone groups, malonylglycosides are the predominant form in raw soybeans, followed by β-glycosides and acetylglycosides, with aglycones rarely observed [6]. Soybeans with a high content of non-conjugated glycosides and aglycones had high-quality antioxidant activity [15]

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