Glyceollins and dehydroglyceollins isolated from soybean act as SERMs and ER subtype-selective phytoestrogens

Schans, M.G.M. van de; Vincken, Jean‐Paul; Waard, Pieter de; Hamers, A.R.M.; Bovee, Toine F.H.; Gruppen, Harry

doi:10.1016/j.jsbmb.2015.11.020

Cited by 31 publications

(22 citation statements)

References 31 publications

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“…Since glyceollin I is costly to purify from other glyceollins [ 23 ], we determined which tissue had the greatest purity of glyceollin I relative to the other glyceollins. The roots produced 85.9% glyceollin I ( Supplementary Figure S1 ), but produced the lowest total amount with our elicitation parameters ( Figure 2 A).…”

Section: Resultsmentioning

confidence: 99%

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

2017

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Phytoalexins are metabolites biosynthesized in plants in response to pathogen, environmental, and chemical stresses that often have potent bioactivities, rendering them promising for use as therapeutics or scaffolds for pharmaceutical development. Glyceollin I is an isoflavonoid phytoalexin from soybean that exhibits potent anticancer activities and is not economical to synthesize. Here, we tested a range of source tissues from soybean, in addition to chemical and biotic elicitors, to understand how to enhance the bioproduction of glyceollin I. Combining the inorganic chemical silver nitrate (AgNO3) with the wall glucan elicitor (WGE) from the soybean pathogen Phytophthora sojae had an additive effect on the elicitation of soybean seeds, resulting in a yield of up to 745.1 µg gt−1 glyceollin I. The additive elicitation suggested that the biotic and chemical elicitors acted largely by separate mechanisms. WGE caused a major accumulation of phytoalexin gene transcripts, whereas AgNO3 inhibited and enhanced the degradation of glyceollin I and 6″-O-malonyldaidzin, respectively.

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Section: Resultsmentioning

confidence: 99%

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

2017

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“…Prenylated isoflavonoids (glabrene, 3′-hydroxy-4′- O -methyl-glabridin, 4′- O -methyl-glabridin, hispaglabridin A, hispaglabridin B, glyceofuran, glyceollidin II, glyceollin I, glyceollin II, glyceollin III, glyceollin IV, glyceollin V, dehydroglyceollidin II, dehydroglyceollin I, dehydroglyceollin II, dehydroglyceollin, III, dehydroglyceollin IV) and one prenylated flavone (glabrol) were previously purified and chemically characterized 45 , 46 . 6-Prenylnaringenin, propidium iodine (PI), Phe-Arg β-naphthylamide dihydrochloride (PaβN), ampicillin and ciprofloxacin were purchased from Sigma Aldrich (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

Araya‐Cloutier

Vincken

Schans

et al. 2018

Sci Rep

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Prenylated flavonoids and isoflavonoids are phytochemicals with remarkable antibacterial activity. In this study, 30 prenylated (iso)flavonoids were tested against Listeria monocytogenes and Escherichia coli (the latter in combination with an efflux pump inhibitor). Minimum inhibitory concentrations of the most active compounds ranged between 6.3–15.0 µg/mL. Quantitative structure-activity relationships (QSAR) analysis was performed and linear regression models were proposed with R2 between 0.77–0.80, average R2m between 0.70–0.75, Q2LOO between 0.66–0.69, and relatively low amount of descriptors. Shape descriptors (related to flexibility and globularity), together with hydrophilic/hydrophobic volume and surface area descriptors, were identified as important molecular characteristics related to activity. A 3D pharmacophore model explaining the effect of the prenyl position on the activity of compounds was developed for each bacterium. These models predicted active compounds with an accuracy of 71–88%. With regard to the mode of action, good antibacterial prenylated (iso)flavonoids with low relative hydrophobic surface area caused remarkable membrane permeabilization, whereas those with higher relative hydrophobic surface area did not. Based on the QSAR and membrane permeabilization studies, the mode of action of antibacterial prenylated (iso)flavonoids was putatively rationalized.

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“…At the molecular level, glyceollins have been shown to interact with ERs and act as weak estrogenic/anti-estrogenic compounds in a cell-dependent manner. It was suggested that glyceollins can behave like selective ER modulators (SERMs) that have partial agonist and antagonist properties depending on the ER isoform or cellular context [117]. In our previous study [25], glyceollins acted essentially as antiestrogenic compounds via the direct inhibition of ER activities in the context of breast cells.…”

Section: Discussionmentioning

confidence: 99%

An Update on the Effects of Glyceollins on Human Health: Possible Anticancer Effects and Underlying Mechanisms

Pham

Lecomte

Efstathiou³

et al. 2019

Nutrients

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Biologically active plant-based compounds, commonly referred to as phytochemicals, can influence the expression and function of various receptors and transcription factors or signaling pathways that play vital roles in cellular functions and are then involved in human health and diseases. Thus, phytochemicals may have a great potential to prevent and treat chronic diseases. Glyceollins, a group of phytoalexins that are isolated from soybeans, have attracted attention because they exert numerous effects on human functions and diseases, notably anticancer effects. In this review, we have presented an update on the effects of glyceollins in relation to their potential beneficial roles in human health. Despite a growing number of studies suggesting that this new family of phytochemicals can be involved in critical cellular pathways, such as estrogen receptor, protein kinase, and lipid kinase signaling pathways, future investigations will be needed to better understand their molecular mechanisms and their specific significance in biomedical applications.

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Glyceollins and dehydroglyceollins isolated from soybean act as SERMs and ER subtype-selective phytoestrogens

Cited by 31 publications

References 31 publications

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

An Update on the Effects of Glyceollins on Human Health: Possible Anticancer Effects and Underlying Mechanisms

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