Mechanism of reaction of nitrogen dioxide radical with hydroxycinnamic acid derivatives: A pulse radiolysis study

Zhang, Zhouen; Yao, Side; Wang, Lin; Wang, Wenfeng; Yizun, Jin; Lin, Nianyun

doi:10.1080/10715769800300021

Cited by 43 publications

(19 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Monohydroxy phenolics (monophenolics such as p ‐CA) and polyhydroxy phenolics (polyphenolics such as caffeic acid or chlorogenic acid) display different scavenging mechanisms against RNS [17,32,35]. Monophenolics, which are less efficient antioxidants than polyphenolics [49], can remove ONOO − (or NO 2 • ) without nitrite production reaction [35].…”

Section: Resultsmentioning

confidence: 99%

“…Monophenolics, which are less efficient antioxidants than polyphenolics [49], can remove ONOO − (or NO 2 • ) without nitrite production reaction [35]. In contrast, nitrite can be produced as the result of reductive destruction of ONOO − (or NO 2 • ) by antioxidant polyphenolics [32]. Although its toxicity is lower than ONOO − , nitrite is still a potential cytotoxin for both plants and animals.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Enzymatic nitration of phytophenolics: evidence for peroxynitrite‐independent nitration of plant secondary metabolites

et al. 2003

View full text Add to dashboard Cite

Peroxynitrite (ONOO 3 ), a reactive nitrogen species, is capable of nitrating tyrosine residue of proteins. Here we show in vitro evidence that plant phenolic compounds can also be nitrated by an ONOO 3 -independent mechanism. In the presence of NaNO 2 , H 2 O 2 , and horseradish peroxidase (HRP), monophenolic p-coumaric acid (p-CA, 4-hydroxycinnamic acid) was nitrated to form 4-hydroxy-3-nitrocinnamic acid. The reaction was completely inhibited by KCN, an inhibitor for HRP. The antioxidant ascorbate suppressed p-CA nitration and its suppression time depended strongly on ascorbate concentration. We conclude that nitrogen dioxide radical (NO c 2 ), but not ONOO 3 , produced by a guaiacol peroxidase is the intermediate for phytophenolic nitration. ß

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Enzymatic nitration of phytophenolics: evidence for peroxynitrite‐independent nitration of plant secondary metabolites

et al. 2003

View full text Add to dashboard Cite

show abstract

“…The complexity of the mixture formed is further illustrated by the observation that the NO 2 radical reacts fast with caffeic acid (k =8.6×10 8 M − 1 .s − 1 ) yielding the o-semiquinone radical [53]. However, this reaction is not likely to contribute in a great extent to the phenol radical formation in our experiments in view of the competition of NO 2 radical with nitrite at microM level for caffeic acid and, also, because HNO 2 used in reaction 2, spontaneously yielding NO 2 radical, will be displaced by reaction 6 with caffeic acid.…”

Section: Discussionmentioning

confidence: 99%

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Gago

Lundberg

Barbosa

et al. 2007

Free Radical Biology and Medicine

155

111

View full text Add to dashboard Cite

Nitrite may be a source for nitric oxide ( U NO), particularly in highly acidic environments, such as the stomach. Diet products contribute also with reductants that dramatically increase the production of U NO from nitrite. Red wine has been attributed health promoting properties largely on basis of the reductive antioxidant properties of its polyphenolic fraction. We show in vitro that wine, wine anthocyanin fraction and wine catechol (caffeic acid) dose-and pH-dependently promote the formation of U NO when mixed with nitrite, as measured electrochemically. The production of U NO promoted by wine from nitrite was substantiated in vivo in healthy volunteers by measuring U NO in the air expelled from the stomach, following consumption of wine, as measured by chemiluminescence. Mechanistically, the reaction involves the univalent reduction of nitrite, as suggested by the formation of U NO and by the appearance of EPR spectra assigned to wine phenolic radicals. Ascorbic and caffeic acids cooperate in the reduction of nitrite to U NO. Moreover, reduction of nitrite is critically dependent on the phenolic structure and nitro-derivatives of phenols are also formed, as suggested by caffeic acid UV spectral modifications. The reduction of nitrite may reveal previously unrecognized physiologic effects of red wine in connection with U NO bioactivity.

show abstract

“…In fact, the MS/MS characterization of the obtained product of the reaction of phenol toward NO 2 ● gave a molecular ion of 139.1, corresponding to a mono‐nitrophenol derivative. The formation of such product can be attributed to a hydrogen atom transfer from the phenol group to the NO 2 ● (Reaction , followed by a rearrangement and reaction with another NO 2 ● molecule. This initial step can involve NO 2 ● or HONO but cannot be due to a NO–phenol adduct (molecular mass 123).…”

Section: Resultsmentioning

confidence: 99%

Kinetics of the Anaerobic Reaction of para‐Substituted Phenols with Nitrogen Dioxide

Reyes

Lissi

López-Alarcón

et al. 2016

Int J of Chemical Kinetics

View full text Add to dashboard Cite

para‐Substituted phenols in aqueous solution under anaerobic conditions readily react with nitrogen dioxide (NO2●) over a wide range of experimental conditions. The rate and rate law of the process were dependent on phenol concentration and solution pH. The kinetic order in phenol changed from one (low concentration) to zero (high concentration), a result attributable to total NO2● capture. Initial consumption rate (r0) of phenols versus pH plots showed parabolic behavior with a minimum rate at pH ca. 5. On the other hand, the maximum rate took place at high pH (pH>10) and involved the protonated phenols. The reaction rate of para‐substituted phenols with NO2● correlated with the bond dissociation energy and with Hammett's parameter. Based on such results and also supported by analysis of products carried out by HPLC‐MS/MS, our data conclusively show that, in spite of the fast acid–base interchanges of phenols and the interconversion of the different nitrogen oxides, the mechanisms of phenols nitration mediated by NO2● or HONO are clearly different.

show abstract

Mechanism of reaction of nitrogen dioxide radical with hydroxycinnamic acid derivatives: A pulse radiolysis study

Cited by 43 publications

References 13 publications

Enzymatic nitration of phytophenolics: evidence for peroxynitrite‐independent nitration of plant secondary metabolites

Enzymatic nitration of phytophenolics: evidence for peroxynitrite‐independent nitration of plant secondary metabolites

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Kinetics of the Anaerobic Reaction of para‐Substituted Phenols with Nitrogen Dioxide

Contact Info

Product

Resources

About