Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Hofmann, Julian; Fayez, Shaimaa; Scheiner, Matthias; Hoffmann, Matthias; Oerter, Sabrina; Appelt‐Menzel, Antje; Maher, Pamela; Maurice, Tangui; Bringmann, Gerhard; Decker, Michael

doi:10.1002/chem.202001264

Cited by 28 publications

(24 citation statements)

References 45 publications

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“…Furthermore, the flavanone sterubin might provide an alternative to fisetin in conditions with an excess of iron since iron did not have an impact on the beneficial effects of sterubin in the various assays. Indeed, we recently showed that sterubin is effective at preserving memory in an acute model of AD [ 68 ].…”

Section: Discussionmentioning

confidence: 99%

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Maher

2020

Antioxidants

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Alterations occur in the homeostasis of the transition metals iron (Fe2+) and copper (Cu2+) during aging and these are further amplified in neurodegenerative diseases, including Alzheimer’s disease (AD). These observations suggest that the most effective drug candidates for AD might be those that can reduce these alterations. The flavonoid fisetin has both neuroprotective and anti-inflammatory activity both in vitro and in vivo and can bind both iron and copper suggesting that its chelating activity might play a role in its beneficial effects. To test this idea, the effects of iron and copper on both the neuroprotective and anti-inflammatory activities of fisetin were examined. It is shown that while fisetin can reduce the potentiation of cell death by iron and copper in response to treatments that lower glutathione levels, it is much less effective when the metals are combined with other inducers of oxidative stress. In addition, iron but not copper reduces the anti-inflammatory effects of fisetin in a dose-dependent manner. These effects correlate with the ability of iron but not copper to block the induction of the antioxidant transcription factor, Nrf2, by fisetin. In contrast, although the flavanone sterubin also binds iron, the metal has no effect on sterubin’s ability to induce Nrf2 or protect cells from toxic or pro-inflammatory insults. Together, these results suggest that while iron and copper binding could contribute to the beneficial effects of neuroprotective compounds in the context of neurodegenerative diseases, the consequences of this binding need to be fully examined for each compound.

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Section: Discussionmentioning

confidence: 99%

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Maher

2020

Antioxidants

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“…Yerba santa is a plant that has been brewed into a tea and used as a bitter flavoring additive to foods historically by Native Americans [ 126 ]. Previous studies have demonstrated that sterubin extracted from Yerba santa exhibited strong neuroprotective properties and held notable potential as a neuroprotectant [ 127 , 128 ]. Recently, scientists found that sterubin is an effective iron chelator, which could inhibit ferroptosis in a dose-dependent way through increasing GSH, decreasing ROS levels and activating Nrf2/ATF4 signaling pathway in glutamate-treated HT22 cells [ 129 ].…”

Section: Natural Bioactive Compounds As Ferroptosis Regulatorsmentioning

confidence: 99%

The Regulatory Effects and the Signaling Pathways of Natural Bioactive Compounds on Ferroptosis

Zhang

Geng

et al. 2021

Foods

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Natural bioactive compounds abundantly presented in foods and medicinal plants have recently received a remarkable attention because of their various biological activities and minimal toxicity. In recent years, many natural compounds appear to offer significant effects in the regulation of ferroptosis. Ferroptosis is the forefront of international scientific research which has been exponential growth since the term was coined. This type of regulated cell death is driven by iron-dependent phospholipid peroxidation. Recent studies have shown that numerous organ injuries and pathophysiological processes of many diseases are driven by ferroptosis, such as cancer, arteriosclerosis, neurodegenerative disease, diabetes, ischemia-reperfusion injury and acute renal failure. It is reported that the initiation and inhibition of ferroptosis plays a pivotal role in lipid peroxidation, organ damage, neurodegeneration and cancer growth and progression. Recently, many natural phytochemicals extracted from edible plants have been demonstrated to be novel ferroptosis regulators and have the potential to treat ferroptosis-related diseases. This review provides an updated overview on the role of natural bioactive compounds and the potential signaling pathways in the regulation of ferroptosis.

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“…This column was the only one which was able to separate all new chiral azoles in another comparative study with several polysaccharide-based columns with various CSs [ 69 ]. The same column demonstrated good enantioselectivity in the analysis of seven process-related impurities of celecoxib as well as for enantiomers of sterubin, a potential neuroprotector extracted from Eriodictyon californicum plant [ 70 , 71 ]. An interesting comparative study was performed on a Chiralcel OJ-3 (particle size 3 µm) column using both SFC and NP-LC.…”

Section: Polysaccharide-based Stationary Phasesmentioning

confidence: 99%

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Grybinik

Bosáková

2021

Monatsh Chem

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Graphic abstract This review provides a brief survey of chiral separation of pharmaceutically active substances published over the last 3 years (2018–2020). Chiral separation of drugs is an important area of research. The control of enantiomeric purity and determination of individual enantiomeric drug molecules is a necessity especially for clinical, analytical, and regulatory purposes. Among chromatographic resolution methods, high-performance liquid chromatography based on chiral stationary phases remains the most popular and effective method used for chiral separation of various drugs. In this review, attention is paid to several classes of chiral stationary phases that have been the most frequently used for drug enantioseparation during this period.

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Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Cited by 28 publications

References 45 publications

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

The Regulatory Effects and the Signaling Pathways of Natural Bioactive Compounds on Ferroptosis

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

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