Antioxidant activity and calcium binding of isomeric hydroxybenzoates

Zhao, Zichen; Vavrušová, Martina; Skibsted, Leif H.

doi:10.1016/j.jfda.2017.07.001

Cited by 10 publications

(3 citation statements)

References 22 publications

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“…One possibility is the chelating ability of 3ʹ,4ʹ‐dihydroxylated flavonoids. Although polyphenols are considered to have a weak Mg‐chelating ability and no Ca‐chelating ability (Hider et al., 2001), Ca binding to plant phenols such as hydroxybenzoates has been reported, which may be extended to plant polyphenols including the catechins (Zhao et al., 2018).…”

Section: Discussionmentioning

confidence: 99%

Flavonoid 3ʹ‐hydroxylase reduces Ca and Mg content in soybean seeds, resulting in decreased hardness of cooked beans

et al. 2022

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Flavonoid 3ʹ-hydroxylase (F3ʹH) catalyzes hydroxylation at the 3ʹ position of the B ring of flavonoids. F3ʹH is associated with the seed coat and pubescence color, antioxidant properties, and chilling stress tolerance of soybean [Glycine max (L.) Merr.]. In this study, we found that soybean F3ʹH increases the calcium (Ca) and magnesium (Mg) contents in pods and reduces the levels of these elements in seeds. Inductively coupled plasma mass spectrometry (ICP-MS) analysis using a near-isogenic line (NIL) derived from Japanese cultivars 'Natto-shoryu' and 'Hyoukei-kuro 3' for F3ʹH (Glyma.06g202300), also known as the T gene, indicated that the contents of Ca and Mg were higher in the pods but lower in the seed coats and cotyledons from soybean with active F3ʹH than from soybean with inactive F3ʹH. No such clear tendency was observed for other inorganic ions measured in this study. These data suggested that the transport of Ca and Mg from the pod to the seed was inhibited by flavonoid produced through F3ʹH activity. The hardness of cooked beans from soybean with active F3ʹH was lower than that from soybean with inactive F3ʹH, which was likely related to the increase in heat-labile pectin caused by fewer cross-linked divalent ions. These results were supported by ICP-MS analysis and the hardness of cooked beans of other NILs for the T gene. Our findings demonstrate a novel and unexpected effect of flavonoids on the processing quality of soybean.

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Section: Discussionmentioning

confidence: 99%

Flavonoid 3ʹ‐hydroxylase reduces Ca and Mg content in soybean seeds, resulting in decreased hardness of cooked beans

et al. 2022

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“…In salicylates, the possible interactions with non-redox active metals such as calcium or magnesium have been reported and both are components of the culture media used (RPMI) in the biological assays. Studies by Zhao et al conclude that calcium affects the antioxidant activity of simple phenols extracted from plants, such as hydroxybenzoates [49,50]. The chelation of the calcium ion could explain the decrease in the antioxidant activity of PVA-[Ch][Sal], which has the lowest antioxidant activity compared to the rest of the gels.…”

Section: Pva-[ch][sal] and Pva-[ch]mentioning

confidence: 99%

Polyphenol Iongel Patches with Antimicrobial, Antioxidant and Anti-Inflammatory Properties

et al. 2023

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There is an actual need for developing materials for wound healing applications with anti-inflammatory, antioxidant, or antibacterial properties in order to improve the healing performance. In this work, we report the preparation and characterization of soft and bioactive iongel materials for patches, based on polymeric poly(vinyl alcohol) (PVA) and four ionic liquids containing the cholinium cation and different phenolic acid anions, namely cholinium salicylate ([Ch][Sal]), cholinium gallate ([Ch][Ga]), cholinium vanillate ([Ch][Van]), and cholinium caffeate ([Ch][Caff]). Within the iongels, the phenolic motif in the ionic liquids plays a dual role, acting as a PVA crosslinker and a bioactive compound. The obtained iongels are flexible, elastic, ionic conducting, and thermoreversible materials. Moreover, the iongels demonstrated high biocompatibility, non-hemolytic activity, and non-agglutination in mice blood, which are key-sought material specifications in wound healing applications. All the iongels have shown antibacterial properties, being PVA-[Ch][Sal], the one with higher inhibition halo for Escherichia Coli. The iongels also revealed high values of antioxidant activity due to the presence of the polyphenol, with the PVA-[Ch][Van] iongel having the highest activity. Finally, the iongels show a decrease in NO production in LPS-stimulated macrophages, with the PVA-[Ch][Sal] iongel displaying the best anti-inflammatory activity (>63% at 200 µg/mL).

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“…Most of the identified phytochemicals in N. sativa seed oil have previously been reported to show antidiabetic, anti-inflammatory, antioxidant, anticancer, antimicrobial, anti-arthritic, anticonvulsant, antiulcer, antihypertensive, anti-nociceptive, hepatoprotective, cytotoxic, antimycomicrobial, antiparasitic, and analgesic activities(Marques et al 2019;Caboni et al 2012;Begum et al 2016;Lang and Buchbauer 2012;Balamurugan et al 2013;Muniyan and Gurunathan 2016;Saeed et al 2012;Zhao et al 2018;Adeoye-Isijola et al 2018;Wu et al 2017; Chavan et al 2009;Yimer et al 2019;Hadi et al 2016; Engels and Brinkmann 2017). These compounds showed varying degrees of binding on the SARS-CoV-2 protein targets(Table 2), as revealed by the change in Gibb's free energy values (ΔG).…”

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confidence: 99%

In silico identification of compounds from Nigella sativa seed oil as potential inhibitors of SARS-CoV-2 targets

Duru

Adegboyega

2021

Bull Natl Res Cent

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Background The growing number of cases, severity and fatality of the COVID-19 pandemic, coupled with the fact that no cure has been found has made infected individuals especially in Africa, to resort to the consumption of different natural products to alleviate their condition. One of such plant materials that have been consumed to remedy the severity of this viral infection is the oil of Nigella sativa seed commonly called black seed oil. In this study, we extracted and characterized the oil from this seed using gas chromatography coupled to a mass selective detector to identify the component phytochemicals. Site-directed multiligand docking of the identified compounds was performed on SARS-CoV-2 molecular targets- Replicase polyprotein 1a, RNA binding protein of NSP9, ADP ribose phosphatase of NSP3, 3-chymotrypsin-like protease 3CLpro, and RNA-dependent RNA polymerase RDRP, and ACE2–angiotensin-converting enzyme from the Homo sapiens. Results The binding affinity of caryophyllene oxide was the highest on 3CLpro (− 6.0 kcal/mol), NSP3 (− 6.3 kcal/mol), NSP9 (− 6.3 kcal/mol), and RDRP (− 6.9 kcal/mol) targets, while α-bergamotene gave the best binding affinity on RPIA (5.7 kcal/mol) target. The binding affinity of β-bisabolene on the ACE2 target (− 8.0 kcal/mol) was almost the same as Remdesivir (− 8.1 kcal/mol). The ADMET properties of these three phytochemicals showed that they are good drug leads for these SARS-CoV-2 receptors. Conclusion The findings from this study strongly indicate that the reported recovery from COVID-19 infection claimed by patients who consumed black seed oil could be linked to the presence of caryophyllene oxide, α-bergamotene, and β-bisabolene in this natural product.

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Antioxidant activity and calcium binding of isomeric hydroxybenzoates

Cited by 10 publications

References 22 publications

Flavonoid 3ʹ‐hydroxylase reduces Ca and Mg content in soybean seeds, resulting in decreased hardness of cooked beans

Flavonoid 3ʹ‐hydroxylase reduces Ca and Mg content in soybean seeds, resulting in decreased hardness of cooked beans

Polyphenol Iongel Patches with Antimicrobial, Antioxidant and Anti-Inflammatory Properties

In silico identification of compounds from Nigella sativa seed oil as potential inhibitors of SARS-CoV-2 targets

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