Development and Validation of an HPLC–DAD Method for Analysis of the Six Major Isoflavones in Extracts from Soybean Processing

Gasparetto, João Cleverson; Smolarek, F. S. F.; Francisco, Thais Martins Guimarães de; Miranda, L. C.; Pontarolo, Roberto; Siqueira, Paula F.

doi:10.1007/s11746-012-2030-1

Cited by 11 publications

(5 citation statements)

References 38 publications

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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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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 the development of the HPLC method, it was observed that the use of acetonitrile as an organic modifier resulted in a better resolution of cyclolinopeptides compared to methanol. Furthermore, the use of methanol resulted in undesirable baseline drifts in the gradient profile [24]. Previous HPLC separation by Brühl et al [15] using methanol/water was only able to separate five CLPs.…”

Section: Efficiency Of Clps Extractionmentioning

confidence: 99%

Flaxseed Cyclolinopeptides: Analysis and Storage Stability

Aladedunye

Sosińska

Przybylski

2012

J Americ Oil Chem Soc

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Fourteen cyclolinopeptides (CLPs) from flaxseed oil and meal were separated, identified and quantified by HPLC coupled to an Orbitrap MS. The oxidative stability of the cyclolinopeptides was assessed during storage of flaxseed oil and meal. A significant decrease in the amounts of the methionine containing CLPs, namely CLP‐B, CLP‐J and CLP‐M, and a concurrent increase in the amounts of methionine sulfoxide containing CLPs, such as CLP‐C, CLP‐E and CLP‐G were observed. The cyclolinopeptides with two methionine units, CLP‐L and CLP‐M, exhibited the greatest decrease, followed by CLP‐J, the major flaxseed oil bitter taste precursor, and CLP‐B, a biologically active cyclolinopeptide. At the end of the storage period, the amount of the bitter CLP‐E increased fourfold in the oil while the immunosuppressive cyclolinopeptides A remained unchanged. No significant changes in the amount of each of the CLPs were observed in the stored flaxseed meals. A fast and reliable procedure has been developed for quantitative analysis of cyclolinopeptides. Due to the high predisposition of methionine containing cyclolinopeptides to oxidation and the easiness of CLPs’ quantification with the proposed method, it is possible to reliably assess the extent of flaxseed meal and oil oxidation.

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“…+ , 539[M + Na] + , 517[M + H] + , 255[M + H-Suc-Glu] + + , 271[M + H] + [19,24,26,27,29,33] + , 455[M + Na] + , 433[M + H] + , 271[M + H-Glu] + + , 455[M + Na] + , 433[M + H] + , 271[M + H-Glu] +[19,24,26,27,29,33] …”

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confidence: 99%

Changes in Isoflavone Profile from Soybean Seeds during Cheonggukjang Fermentation Based on High-Resolution UPLC-DAD-QToF/MS: New Succinylated and Phosphorylated Conjugates

et al. 2022

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In this study, thirty-eight isoflavone derivatives were comprehensively identified and quantified from the raw, steamed and fermented seeds of four selected soybean cultivars based on UPLC-DAD-QToF/MS results with reference to the previously reported LC-MS library and flavonoid database, and summarized by acylated group including glucosides (Glu), malonyl-glucosides (Mal-Glu), acetyl-glucosides (Ac-Glu), succinyl-glucosides (Suc-Glu) and phosphorylated conjugates (Phos) in addition to aglycones. Among them, Suc-Glu and Phos derivatives were newly generated due to fermentation by B. subtilis AFY-2 (cheonggukjang). In particular, Phos were characterized for the first time in fermented soy products using Bacillus species. From a proposed roadmap on isoflavone-based biotransformation, predominant Mal-Glu (77.5–84.2%, raw) decreased rapidly by decarboxylation and deesterification into Ac-Glu and Glu (3.5–8.1% and 50.0–72.2%) during steaming, respectively. As fermentation continued, the increased Glu were mainly succinylated and phosphorylated as well as gradually hydrolyzed into their corresponding aglycones. Thus, Suc-Glu and Phos (17.3–22.4% and 1.5–5.4%, 36 h) determined depending on cultivar type and incubation time, and can be considered as important biomarkers generated during cheonggukjang fermentation. Additionally, the changes of isoflavone profile can be used as a fundamental report in applied microbial science as well as bioavailability research from fermented soy foods.

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Development and Validation of an HPLC–DAD Method for Analysis of the Six Major Isoflavones in Extracts from Soybean Processing

Cited by 11 publications

References 38 publications

Analysis of Isoflavones in Foods

Analysis of Isoflavones in Foods

Flaxseed Cyclolinopeptides: Analysis and Storage Stability

Changes in Isoflavone Profile from Soybean Seeds during Cheonggukjang Fermentation Based on High-Resolution UPLC-DAD-QToF/MS: New Succinylated and Phosphorylated Conjugates

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