Autoxidation of nicotine

Wada, Einosuke; Kisaki, Takuro; Saito, Kenji

doi:10.1016/0003-9861(59)90385-6

Cited by 35 publications

(32 citation statements)

References 11 publications

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“…Other reported nicotine metabolites like nicotinic acid, cotinine, nicotine oxides, nitrosamines, N-formylnornicotine and derivatives [18,21,[23][24][25] could not be detected in the fermented aqueous extract samples. These results were all verified with another batch of fermented aqueous extract (batch 2007).…”

Section: Metabolism Of Nicotine In Fermented Aqueous Extractscontrasting

confidence: 58%

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Validation of a GC–FID method for rapid quantification of nicotine in fermented extracts prepared from Nicotiana tabacum fresh leaves and studies of nicotine metabolites

Millet

Stintzing

Merfort

2009

Journal of Pharmaceutical and Biomedical Analysis

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Section: Metabolism Of Nicotine In Fermented Aqueous Extractscontrasting

confidence: 58%

“…Traces of myosmine, known as metabolite of nicotine and nornicotine generated enzymatically or under exclusion of oxygen [18,21], were detected in the extract in the period from 24 h until 2 months. During the same time period, the amount decreased perpetually.…”

Section: Metabolism Of Nicotine In Fermented Aqueous Extractsmentioning

confidence: 99%

Validation of a GC–FID method for rapid quantification of nicotine in fermented extracts prepared from Nicotiana tabacum fresh leaves and studies of nicotine metabolites

Millet

Stintzing

Merfort

2009

Journal of Pharmaceutical and Biomedical Analysis

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“…Possible reactions with ROS are shown (25). Their probability is corroborated by various chemical studies on nicotine (Hucker et al, 1959;Taylor and Boyer, 1959;Wada et al, 1959;Craig et al, 1964;Mohrle and Berlitz, 2008;Mohrle and Berlitz, 2009).…”

Section: Hormesis and Plant Secondary Metabolitessupporting

confidence: 48%

Hormesis and a Chemical Raison D'ětre for Secondary Plant Metabolites

Hadaček¹,

Bachmann²,

Engelmeier³

et al. 2010

Dose-Response

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ᮀ In plants, accumulation in specific compartments and huge structural diversity of secondary metabolites is one trait that is not understood yet. By exploring the diverse abiotic and biotic interactions of plants above-and belowground, we provide examples that are characterized by nonlinear effects of the secondary metabolites. We propose that redox chemistry, specifically the reduction of reactive oxygen species (ROS) and, in their absence, reduction of molecular oxygen by the identical secondary metabolite, is an important component of the hormetic effects caused by these compounds. This is illustrated for selected phenols, terpenoids, and alkaloids. The redox reactions are modulated by the variable availability of transition metals that serve as donors of electrons in a Fenton reaction mode. Low levels of ROS stimulate growth, cell differentiation, and stress resistance; high levels induce programmed cell death. We propose that provision of molecules that can participate in this redox chemistry is the raison d'être for secondary metabolites. In this context, the presence or absence of functional groups in the molecule is more essential than the whole structure. Accordingly, there exist no constraints that limit structural diversity. Redox chemistry is ubiquitous, from the atmosphere to the soil.

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“…Nicotinic acid, myosmine, cotinine, nicotyrine, nicotine-N-oxide, methanone-(1-methyl-3-pyrrolidinyl)-3-pyridinyl and β-nicotyrine have been identified as oxidation products (18,19). Reaction with O 2 is inhibited in acidified solutions, therefore only the free base is susceptible to oxidation (20).…”

Section: Submitted To Environmental Science and Technologymentioning

confidence: 99%