Isoflavones: Chemistry, Analysis, Functions and Effects on Health and Cancer

Ko, Kwang Pil

doi:10.7314/apjcp.2014.15.17.7001

Cited by 122 publications

(105 citation statements)

References 80 publications

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“…2a), which was slightly higher than the previous reports (Li et al, 2012;2013;Fujita et al, 2015;Kaur and Chadha, 2015;Zhao et al, 2015). In addition, the enzyme showed more than 97% relative activity at 75 °C, and showed no significant difference from the activity at 65 °C (P>0.05), while other fungal counterparts were generally inactivated at 70 °C (Li et al, 2013;Fujita et al, 2015;Kaur and Chadha, 2015;Zhao et al, 2015).…”

Section: Optimal Ph and Temperature And Stabilitycontrasting

confidence: 54%

“…They have attracted considerable attention for their pharmacological effects, such as preventing certain cancers (breast, prostate, and colon) (Ravindranath et al, 2004;Ullah et al, 2016), decreasing the risk of cardiovascular diseases (Imai, 2015), improving bone health (Alekel et al, 2015), and preventing menopausal symptoms (Ko, 2013). Moreover, studies revealed that isoflavone aglycones, such as daidzein and genistein, are superior to isoflavone glycosides in various bioactivities.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of β-glucosidase from Aspergillus terreus and its application in the hydrolysis of soybean isoflavones

Yan

Xia

Zhang

et al. 2016

J. Zhejiang Univ. Sci. B

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An extracellular β-glucosidase produced by Aspergillus terreus was identified, purified, characterized and was tested for the hydrolysis of soybean isoflavone. Matrix-assisted laser desorption/ionization with tandem time-offlight/time-of-flight mass spectrometry (MALDI-TOF/TOF MS) revealed the protein to be a member of the glycosyl hydrolase family 3 with an apparent molecular mass of about 120 kDa. The purified β-glucosidase showed optimal activity at pH 5.0 and 65 °C and was very stable at 50 °C. Moreover, the enzyme exhibited good stability over pH 3.0-8.0 and possessed high tolerance towards pepsin and trypsin. The kinetic parameters K m (apparent MichaelisMenten constant) and V max (maximal reaction velocity) for p-nitrophenyl-β-D-glucopyranoside (pNPG) were 1.73 mmol/L and 42.37 U/mg, respectively. The K m and V max for cellobiose were 4.11 mmol/L and 5.7 U/mg, respectively. The enzyme efficiently converted isoflavone glycosides to aglycones, with a hydrolysis rate of 95.8% for daidzin, 86.7% for genistin, and 72.1% for glycitin. Meanwhile, the productivities were 1.14 mmol/(L·h) for daidzein, 0.72 mmol/(L·h) for genistein, and 0.19 mmol/(L·h) for glycitein. This is the first report on the application of A. terreus β-glucosidase for converting isoflavone glycosides to their aglycones in soybean products.

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Section: Optimal Ph and Temperature And Stabilitycontrasting

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Characterization of β-glucosidase from Aspergillus terreus and its application in the hydrolysis of soybean isoflavones

Yan

Xia

Zhang

et al. 2016

J. Zhejiang Univ. Sci. B

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“…This study listed 510 isoflavone related structures, supplemented by ca. 130 glycoside derivatives Some 30 years later, book chapters devoted to natural isoflavones refer to circa 1600 structures with this type of flavonoid skeleton, comprising not just simple isoflavones but also isoflavanones, isoflavenes, rotenoids, pterocarpans, coumestans, chalcones and deoxybenzoins, as well as their O - and C - glycosidic derivatives [17, 20, 22]. All these structures are presently available not only through disclosures in original scientific literature but also in dictionaries and databases [23].…”

Section: Structure and Biosynthesis Of Isoflavonesmentioning

confidence: 99%

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

Szeja

Grynkiewicz

Rusin

2016

COC

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Glycosylation of small biologically active molecules, either of natural or synthetic origin, has a profound impact on their solubility, stability, and bioactivity, making glycoconjugates attractive compounds as therapeutic agents or nutraceuticals. A large proportion of secondary metabolites, including flavonoids, occur in plants as glycosides, which adds to the molecular diversity that is much valued in medicinal chemistry studies. The subsequent growing market demand for glycosidic natural products has fueled the development of various chemical and biotechnological methods of glycosides preparation. The review gives an extensive overview of the processes of the synthesis of isoflavones and discusses recently developed major routes towards isoflavone-sugar formation processes. Special attention is given to the derivatives of genistein, the main isoflavone recognized as a useful lead in several therapeutic categories, with particular focus on anticancer drug design. The utility of chemical glycosylations as well as glycoconjugates preparation is discussed in some theoretical as well as practical aspects. Since novel approaches to chemical glycosylations and glycoconjugations are abundant and many of them proved suitable for derivatization of polyphenols a new body of evidence has emerged, indicating that sugar moiety can play a much more significant role, when attached to a pharmacophore, then being a mere “solubilizer”. In many cases, it has been demonstrated that semisynthetic glycoconjugates are much more potent cytostatic and cytotoxic agents than reference isoflavones. Moreover, the newly designed glycosides or glycoside mimics can act through different mechanisms than the parent active molecule.

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“…Protein tyrosine kinase inhibitors in soy-isoflavones play a role in improving cardiovascular function and inhibition of growth and proliferation of gastric cancer cells (Piontek et al, 1993;Yu et al, 2012). The role of soy-isoflavones in activating endothelial nitric oxide synthase, elevating prostacyclin levels, inhibiting cell proliferation, relaxing vessels, and reducing plaque has also been studied (Cano et al, 2010;Ko, 2014). In addition, isoflavones aid in the promotion of nodulation by rhizobia, microorganism cluster changes around roots, and biotic stress resistance (Zeng et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Isoflavone profile diversity in Korean wild soybeans ( Glycine soja Sieb. & Zucc.)

Tsukamoto¹,

Nawaz²,

Kurosaka³

et al. 2018

Turk J Agric For

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Isoflavones prevent the incidence of cancer, reduce cardiovascular problems, and decrease menopausal symptoms. In soybean (Glycine soja Sieb. & Zucc.) seeds, the content is greatly affected by growing conditions. The variations in soy-isoflavone content were investigated by growing 346 Korean wild soybean accessions from natural habitats under the same agroclimatic conditions. Highperformance liquid chromatography was used to measure the profiles of six soy-isoflavones, i.e. glycosides (daidzin, glycitin, genistin) and malonyl glycosides (malonyl-daidzin, malonyl-glycitin, and malonyl-genistin). The soy-isoflavone content of the wild soybeans ranged from 0.5 to 5.51 mg/g with an average of 2.78 mg/g. The highest mean total soy-isoflavone was genistin (1.393 mg/g), followed by daidzin (0.939 mg/g) and glycitin (0.250 mg/g). Korean wild soybean seeds examined in this study were rich in malonyl-genistin. An increasing trend for total soy-isoflavone content was observed from the north to the southeast in the geographical distribution sites, which signifies the effect of genotype and collection site. The information generated in this report will greatly aid soybean breeding stratagems aimed at improving soy-isoflavone concentration in soybean seeds.

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Isoflavones: Chemistry, Analysis, Functions and Effects on Health and Cancer

Cited by 122 publications

References 80 publications

Characterization of β-glucosidase from Aspergillus terreus and its application in the hydrolysis of soybean isoflavones

Characterization of β-glucosidase from Aspergillus terreus and its application in the hydrolysis of soybean isoflavones

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

Isoflavone profile diversity in Korean wild soybeans ( Glycine soja Sieb. & Zucc.)

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