Biosynthesis and metabolism of nicotine and related alkaloids

Bush, Lowell P.; Fannin, Franklin F.; Chelvarajan, R. Lakshman; Burton, H. R.

doi:10.1007/978-94-011-2110-1_1

Cited by 19 publications

(16 citation statements)

References 79 publications

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“…Nicotinate concentrations were also dramatically increased from its precursors glyceraldehyde‐3‐phosphate and aspartate (Figs 7a, S6). This compound is a precursor of secondary metabolism linked to the synthesis of several alkaloids with diverse properties related to stress protection and defence against pathogens (Bush et al , 1993; Matsuura & Fett‐Neto, 2015). Primary antioxidant metabolism was also prompted, as indicated by the increased levels of DHA (Figs 7b, S6) and previously observed under a water stress treatment in the resurrection species H. rhodopensis (Benina et al , 2013).…”

Section: Discussionmentioning

confidence: 99%

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

et al. 2020

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Summary Resurrection plants recover physiological functions after complete desiccation. Almost all of them are native to tropical warm environments. However, the Gesneriaceae include four genera, remnant of the past palaeotropical flora, which inhabit temperate mountains. One of these species is additionally freezing‐tolerant: Ramonda myconi. We hypothesise that this species has been able to persist in a colder climate thanks to some resurrection‐linked traits. To disentangle the physiological mechanisms underpinning multistress tolerance to desiccation and freezing, we conducted an exhaustive seasonal assessment of photosynthesis (gas exchange, limitations to partitioning, photochemistry and galactolipids) and primary metabolism (through metabolomics) in two natural populations at different elevations. R. myconi displayed low rates of photosynthesis, largely due to mesophyll limitation. However, plants were photosynthetically active throughout the year, excluding a reversible desiccation period. Common responses to desiccation and low temperature involved chloroplast protection: enhanced thermal energy dissipation, higher carotenoid to Chl ratio and de‐epoxidation of the xanthophyll cycle. As specific responses, antioxidants and secondary metabolic routes rose upon desiccation, while putrescine, proline and a variety of sugars rose in winter. The data suggest conserved mechanisms to cope with photo‐oxidation during desiccation and cold events, while additional metabolic mechanisms may have evolved as specific adaptations to cold during recent glaciations.

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Section: Discussionmentioning

confidence: 99%

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

et al. 2020

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“…The content of the secondary alkaloid nornicotine is normally <3.5% (1,2). As early as the middle part of the 20th century, Goodspeed (3) and Gerstel (4) reported that nornicotine was the major alkaloid in Nicotiana sylVestris and Nicotiana tomentosformis, progenitor species of tobacco.…”

Section: Introductionmentioning

confidence: 99%

Stimulation of Nicotine Demethylation by NaHCO₃ Treatment Using Greenhouse-Grown Burley Tobacco

Shi¹,

Kalengamaliro²,

Krauss³

et al. 2003

J. Agric. Food Chem.

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Experiments were conducted in tobacco (Nicotiana tabacum L.) to investigate the effect of sodium bicarbonate (NaHCO(3)) on the conversion of nicotine to nornicotine, a secondary alkaloid that can form the tobacco-specific nitrosamine N-nitrosonornicotine (NNN). The results showed that, under optimum conditions, NaHCO(3) stimulated nicotine conversion in converter plants to the maximum level predetermined by the genetic background. The conversion level in NaHCO(3)-treated leaves was 2-3 times higher than that in control leaves. For young seedlings the optimum concentration of sodium bicarbonate was 0.8% aqueous solution, and for adult plants the optimum concentration was 1%. Lower concentrations resulted in partial stimulation, whereas higher concentration damaged leaf tissue and resulted in a lower conversion level. Studies with different temperatures (from 22 to 43 degrees C) showed that 37 degrees C was optimal. This temperature allowed the least amount of time, 2-3 days for mature leaves and 4-6 days for green leaves, for the major converters to reach >95% of nicotine conversion. An examination of leaves from different growth stages and stalk positions showed that the amount of time needed for conversion was longer for young leaves and shorter for mature leaves. Treatment of leaves with NaHCO(3) affords a rapid and convenient means of identifying and removing nornicotine converter plants during growth in the greenhouse or field.

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“…Microwave-accelerated solvent-free synthesis of N-1-methyl-6-(pyridin-3-yl)piperidine-2-thione (1) and N-1-methyl-5-(pyridin-3-yl)pyrrolidine-2-thione (2) A mixture of N-1-methyl-6-(pyridin-3-yl)piperidine-2-one (4) (83 mg; 0.44 mM) and Lawesson's reagent (141 mg; 0.35 mM) was taken in a glass tube and mixed thoroughly. The glass tube was placed in an aluminia bath inside the microwave oven (800 W) and irradiated for 3.5 min.…”

Section: 22mentioning

confidence: 99%

“…The tobacco alkaloids nicotine, nornicotine and anabasine show a wide spectrum of biological activity and are used as precursors for drug design and pesticide preparation [1][2][3]. They exert negative effect on the cardio-vascular system and alimentary system, cause sleep disturbance and addiction [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

Wojciechowska-Nowak

Boczoń

Warżajtis

et al. 2011

Journal of Molecular Structure

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Biosynthesis and metabolism of nicotine and related alkaloids

Cited by 19 publications

References 79 publications

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

Stimulation of Nicotine Demethylation by NaHCO₃ Treatment Using Greenhouse-Grown Burley Tobacco

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

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Biosynthesis and metabolism of nicotine and related alkaloids

Cited by 19 publications

References 79 publications

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

Born to revive: molecular and physiological mechanisms of double tolerance in a paleotropical and resurrection plant

Stimulation of Nicotine Demethylation by NaHCO3 Treatment Using Greenhouse-Grown Burley Tobacco

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

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Stimulation of Nicotine Demethylation by NaHCO₃ Treatment Using Greenhouse-Grown Burley Tobacco