Reaction of Ferulic Acid with Nitrite:  Formation of 7-Hydroxy-6-methoxy-1,2(4<i>H</i>)-benzoxazin-4-one

Rousseau, Brigitte; Rosazza, John P. N.

doi:10.1021/jf980130f

Cited by 30 publications

(35 citation statements)

References 11 publications

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“…mechanism [14] (Scheme 1(a)). As well, studies conducted on the reaction between p-coumaric, ferulic, and caffeic acid, and acid nitrite (HNO 2 ), reported the formation of nitrous and nitro derivatives through the intermediacy of NO [15] [16] [17] [18]. All these results support the E.T.…”

supporting

confidence: 57%

Nitric Oxide: The Key Molecule for Polyphenols Antimicrobial Action

Grossi¹,

Casadei²

2020

JBM

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The role of hydroxycinnamic acids as antioxidants, in vivo, has been widely discussed, but, recently, a great debate has focused on their antimicrobial action. In general, for the hydroxycinnamic acids' action, the presence of NO, which is known to be an antimicrobial agent, seems compulsory; its production goes through the intermediacy of the nitrosonium ion, and a very low pH, for instance, as in the stomach, is requested. However, the action of the hydroxycinnamic acids seems to take place even in different biological compartments, i.e., characterized by different pHs and conditions, and then, for NO production, an alternative mechanism could be involved. In this light, evidence for the NO formation, via an E.T. mechanism, even in mildly acidic conditions (pH = 6.4), was obtained by reacting an aqueous buffer solution of acidic nitrite (HNO 2 ) with the hydroxycinnamic acids ferulic, caffeic, p-coumaric and sinapic. Experiments conducted by EPR spectroscopy, let to detect the NO formation, and the efficiency of the process depending on the available amount of free polyphenol, and the intrinsic nature of the hydroxycinnamic acids. Thus, the production of NO through a non-enzymatic mechanism, in light acidic conditions, would account for the antimicrobial action of hydroxycinnamic acids, even in unconventional biological compartments, and for NO as the key-molecule.

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supporting

confidence: 57%

Nitric Oxide: The Key Molecule for Polyphenols Antimicrobial Action

Grossi¹,

Casadei²

2020

JBM

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“…The five inhibitors used in OSD work either via a redox pathway by reducing the nitrosating agent to non-nitrosating nitric oxide, 17,18 or via nitration reactions. 12,19 A different mechanistic pathway, viz. diazotization of primary amines, can also be exploited to inhibit nitrosamine formation.…”

Section: Communicationmentioning

confidence: 99%

Inhibition of N-Nitrosamine Formation in Drug Products: A Model Study

Nanda

Tignor

Clancy

et al. 2021

Journal of Pharmaceutical Sciences

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“…+ with SOM (Nommik and Nilsson, 1963;Azhar et al, 1989;Rousseau and Rosazza, 1998;Thorn and Mikita, 2000).…”

Section: N Immobilization In the Soilmentioning

confidence: 99%

Chemical Composition of High Organic Carbon Soil Amendments Affects Fertilizer-Derived N2O Emission and Nitrogen Immobilization in an Oxic Sandy Loam

Wei

Amelung

Brüggemann

et al. 2020

Front. Environ. Sci.

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Nitrous oxide (N 2 O) emission is a negative side effect of modern agriculture and a serious issue for global climate change. The combined application of nitrogen (N) fertilizer and high organic carbon soil amendments (HCA) has been regarded as an alternative to promote fertilizer-related N immobilization and enhance nitrogen use efficiency. The effect of HCA on N 2 O emission and N immobilization highly depends on its chemical composition, as it controls carbon (C) supply to soil microbes and reactivity of ligninderived phenols to fertilizer-derived N species. Here we present a 127-d laboratory incubation study to explore the N 2 O emission and N immobilization after combined application of N fertilizer and HCA (wheat straw, spruce sawdust, and commercial alkali lignin) differing in their chemical composition. The 15 N labeling technique was used to trace the transformation of fertilizer-N in ammonium (NH 4 +), nitrate (NO 3 −), soil organic nitrogen (SON), and N 2 O. The amendment of wheat straw and spruce sawdust greatly promoted N immobilization and N 2 O emission, while lignin amendment enhanced the immobilization of fertilizer N. The chemical composition of HCA explained 26% of the total variance of fertilizer-derived N 2 O emission and N retention via soil microbial biomass, composition of lignin-derived phenols, and nitrification. The holocellulose/lignin ratio of HCA could be used as an indicator for predicting HCA decomposition, microbial N immobilization and N 2 O emission. In addition, the composition of lignin-derived phenols was affected by HCA amendment and significantly related to N 2 O emission and N retention. The varying chemical composition of HCA could thus be a promising tool for controlling N 2 O emission and N immobilization in environment-friendly and climate-smart agriculture.

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Reaction of Ferulic Acid with Nitrite: Formation of 7-Hydroxy-6-methoxy-1,2(4H)-benzoxazin-4-one

Cited by 30 publications

References 11 publications

Nitric Oxide: The Key Molecule for Polyphenols Antimicrobial Action

Nitric Oxide: The Key Molecule for Polyphenols Antimicrobial Action

Inhibition of N-Nitrosamine Formation in Drug Products: A Model Study

Chemical Composition of High Organic Carbon Soil Amendments Affects Fertilizer-Derived N2O Emission and Nitrogen Immobilization in an Oxic Sandy Loam

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