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KMID : 1134820210500090950
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Journal of the Korean Society of Food Science and Nutrition
2021 Volume.50 No. 9 p.950 ~ p.961
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Isoflavone Characterization in Soybean Seed and Fermented Products Based on High-Resolution Mass Spectrometry
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Kwon Ryeong-Ha
Kim Heon-Woong
Lee Su-Ji
Lee So-Jeong
Na Hye-Min
Kim Ju-Hyung
Wee Chi-Do
Yoo Seon-Mi
Lee Sang-Hoon
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Abstract
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This study conducted an accurate analysis of isoflavone derivatives, including succinylglucosides, which are identified from fermented soybean products using high-resolution mass spectrometry (UPLC-DAD-QTOF/MS). A total of thirty-six isoflavone components were isolated and identified from soybean seeds (raw and steamed) and commercial fermented products (cheonggukjang, cheonggukjang powder, and natto). Among them, ten novel compounds were tentatively identified for the first time (5 daidzein- and 5 genistein derivatives). In particular, eight succinylglucosides newly generated by Bacillus subtilis during fermentation were structures in which succinic acid was combined with the glucose of the corresponding daidzein (new 3 types), genistein (new 2 types), and glycitein, and among them, 6″-O-succinyldaidzin and 6″-O-succinylgenistin were confirmed as the predominant components. The total isoflavone content (mg/100 g, dry weight) of soybean seeds (raw and steamed), cheonggukjang, and natto ranged from 294.95 to 411.93 mg/100 g. The raw soybean seed was composed of malonylglucosides (75.9%)> monoglucosides> aglycone> acetylglucosides (0.1%), whereas the steamed soybean seed presented as monoglycosides (72.5%)> acetylglucosides (13.5%)> malonylglucosides> aglycones. In addition, cheonggukjang, cheonggukjang powder, and natto mainly contained monoglucosides (46.0%, 56.5%, and 70.0%, respectively) and succinylglucosides (20.3%, 22.5%, and 13.6%, respectively). It is considered that the isoflavone profiles including the additional succinylglucosides can be of fundamental use in applied science related to fermented soybean foods.
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KEYWORD
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soybean, fermentation, isoflavone, succinylglucoside, UPLC-DAD-QTOF/MS
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