Thermal behavior of malonylglucoside isoflavones in soybean flour analyzed by RPHPLC/DAD and eletrospray ionization mass spectrometry

Aguiar, Cláudio Lima de; Haddad, Renato; Eberlin, Marcos N.; Carrão-Panizzi, M. C.; Tsai, Siu Mui; Park, Yong K.

doi:10.1016/j.lwt.2012.02.017

Cited by 30 publications

(23 citation statements)

References 16 publications

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“…In fact, industrial oil extraction includes thermal treatment that appears to play an important role in the isoflavone profile of defatted soy flour. Several studies have demonstrated that heat treatment of soybean flour promotes almost total conversion of malonylglycoside to β ‐glycosides without formation of acetylglycoside isoflavones, and this process is highly dependent on temperature . Thus, soy flour after industrial oil extraction should contain high levels of β ‐glycosides.…”

Section: Resultsmentioning

confidence: 99%

“…Several studies have demonstrated that heat treatment of soybean flour promotes almost total conversion of malonylglycoside to -glycosides without formation of acetylglycoside isoflavones, and this process is highly dependent on temperature. 36 Thus, soy flour after industrial oil extraction should contain high levels of -glycosides. However, our results showed that aglycones are the major isoflavone group followed by -glycosides.…”

Section: Determination Of Total Phenolic Content and Compound Identifmentioning

confidence: 99%

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Antioxidant and antimicrobial activity of natural phenolic extract from defatted soybean flour by‐product for stone fruit postharvest application

et al. 2015

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Section: Resultsmentioning

confidence: 99%

Section: Determination Of Total Phenolic Content and Compound Identifmentioning

confidence: 99%

Antioxidant and antimicrobial activity of natural phenolic extract from defatted soybean flour by‐product for stone fruit postharvest application

et al. 2015

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“…The most frequently used solvent mixture for the extraction of the 12 major forms of isoflavones from soybeans and their derivatives is 80% aqueous methanol (Cavaliere and others ; Fiechter and others ; Hong and others ; Aguiar and others ; Gasparetto and others ; Fahmi and others ; Fonseca and others ; López‐Gutiérrez and others ; Verardo and others ). In very few cases pure methanol is used to carry out the extraction (Otieno and others ).…”

Section: Sample Preparationmentioning

confidence: 99%

Analysis of Isoflavones in Foods

Bustamante-Rangel

Delgado-Zamarreño

Pérez‐Martín

et al. 2018

Comp Rev Food Sci Food Safe

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In recent years the nutritional and bioactive properties of foods are being intensively investigated with a view to control, in addition to food quality, their possible influence on human health. Because of this, there is a growing demand for rapid, selective, sensitive, and validated methods for analysis and quantification. Bioactive plant compounds include those with weak estrogenic activity (phytoestrogens), among which are the isoflavones. Some of the beneficial activities that have been attributed to isoflavones are anticarcinogenic activity, the prevention of cardiovascular disease, the improvement of bone health, and antioxidant activity. The objective of this work is to provide an updated review of the methods used in sample preparation and subsequent analysis for the determination of isoflavones in food samples, including both soybean and soy products, as well as other foods with low isoflavone contents. The review focuses on the most common sample preparation techniques used during the last 10 years, including both conventional solvent extraction and other more recent extraction techniques. Separation and detection methods, including current trends in liquid chromatography analysis, such as the use of monolithic columns or ultra-high-pressure liquid chromatography, are also discussed.

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“…All soaking conditions promoted the reduction of malonyldaidzin, malonylgenistin, and malonylglycitin in soy protein concentrate when compared to control treatment (Table ). Malonylglucoside forms of isoflavones are sensitive and unstable with respect to thermal treatment being susceptible to both decarboxylation and de‐esterification reactions, forming the respective acetylglucosides and β‐glucosides, and after enzyme treatment they may be converted into aglycones (Aguiar et al, ; Park, Aguiar, Alencar, Mascarenhas, & Scamparini, ). The thermal instability of malonylglucosides was also observed during soybean soaking at different temperatures (41, 45, 55, 65, and 69°C) (Lima & Ida, ) and during soymilk processing at 40, 50, and 60°C (Baú & Ida, ).…”

Section: Resultsmentioning

confidence: 99%

Isoflavone profile and protein molecular weight distribution of soy protein concentrates after soaking treatments

Wally

Hoffmann

Bauer

et al. 2019

J Food Process Preserv

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The effects of soybean soaking at 40, 50, and 60°C, during 4, 8, 12, and 16 hr time periods, on the isoflavone profile and molecular weight distribution of proteins in their soy protein concentrate were evaluated. Results indicated that soaking treatments increased aglycone content (daidzein, genistein, and glycitein) and decreased β‐glucosylated and malonyl glucosylated isoflavone contents. Soy protein concentrate obtained after soaking at 50°C for 16 hr yielded the greatest total aglycone content (5,993.6 µmol 100 g−1), which was 75% greater than the total aglycone content found in soy protein concentrate obtained from non‐treated soybeans (3,636.9 µmol 100 g−1). Glycitein was the main isoflavone aglycone present in soy protein concentrates. Acidic and basic subunits of 11S globulins are released at low and intermediate soaking periods (4, 8, and 12 hr), while longer soaking time (16 hr) causes a protein rearrangement of partially cleaved proteins into more hydrophobic core. Practical applications Soy‐based food products can be considered functional foods because of their isoflavone content, mainly the aglycone content (daidzein, genistein, and glycitein). The utilization of soaking treatment in soybeans may increase the isoflavone aglycone content in soy protein concentrate. Our results indicated that soaked soybeans had more isoflavone aglycone content than untreated ones. The highest isoflavone aglycone content was obtained from soaked soybeans at 50°C for 16 hr and glycitein was the predominant isoflavone aglycone found in soy protein concentrates. The obtained soy protein concentrate can be used in a wide range of products, such as bread, cakes, cereals, beverages, and meat products, and contributes to increasing the nutritional and functional value of the product, mainly due to the quantity and quality of proteins and isoflavones.

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Thermal behavior of malonylglucoside isoflavones in soybean flour analyzed by RPHPLC/DAD and eletrospray ionization mass spectrometry

Cited by 30 publications

References 16 publications

Antioxidant and antimicrobial activity of natural phenolic extract from defatted soybean flour by‐product for stone fruit postharvest application

Antioxidant and antimicrobial activity of natural phenolic extract from defatted soybean flour by‐product for stone fruit postharvest application

Analysis of Isoflavones in Foods

Isoflavone profile and protein molecular weight distribution of soy protein concentrates after soaking treatments

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