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, Agnès; Stintzing, Florian C.; Merfort, Irmgard

doi:10.1016/j.jpba.2009.02.024

Cited by 14 publications

(14 citation statements)

References 18 publications

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“…We could recently demonstrate that chrysohermidin (4), as a dimeric piperidine-2,6-dione, spontaneously reacts in the presence of nucleophiles like methanol via benzilic acid rearrangement, under contraction of both six-membered rings into five-membered rings and esterification to yield isochrysohermidin (13, for structure, see Figure 3) [31]. Hence, a similar reaction of 4 in the presence of water was supposed, which should lead to isochrysohermidinic acid (14) as a further intermediate (Figure 7). The acid 14 might henceforth react to 8 by step-wise decarboxylation under the influence of microbial enzymes (Figure 7).…”

Section: Fermentation Of M Perennis With the Lactobacteria Isolates mentioning

confidence: 95%

“…After filtration, the obtained aqueous extract was kept for another 12 h in a refrigerator. For the isolation of isochrysohermidinic acid (14) the extract (385 mL) was applied onto an Amberlite ® IRA 402 anion exchanger column (l = 25 cm, d = 3 cm), which was conditioned with 0.1 N HCl (1 L) and water (4 L). After extract application, the column was washed with water (2 L, fraction discarded) and the target material eluted with 0.1 N HCl (600 mL).…”

Section: Enrichment Of Isochrysohermidinic Acid (14) From An Aqueous mentioning

confidence: 99%

“…For this purpose, 13 [31] was treated in a THF/MeOH solution with 0.25 N NaOH. After pH adjustment to 7.0 with AcOH, the intermediate isochrysohermidinic acid (14) thus formed, was decarboxylated upon addition of aqueous bromine (Br2) solution according to a method of Pink and Stewart [46]. After AcOEt extraction and chromatographic purification, plicatanin B (8) was obtained as a pure compound with a 40.8% yield.…”

Section: Fermentation Of M Perennis With the Lactobacteria Isolates mentioning

confidence: 99%

“…Fermentation of herbal extracts may further be used to enhance the functional features of medicinal plants or diminish toxic side effects [10][11][12][13]. We have recently studied the LAB fermentation chemistry of several medicinal plants [14][15][16][17][18]. However, numerous microbial conversion pathways of plant constituents still remain unknown, a reason to put further efforts into this research area.…”

Section: Introductionmentioning

confidence: 99%

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Conversion of Plant Secondary Metabolites upon Fermentation of Mercurialis perennis L. Extracts with two Lactobacteria Strains

et al. 2019

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Microbial fermentation of plant extracts with Lactobacteria is an option to obtain microbiologically stable preparations, which may be applied in complementary medicine. We investigated the metabolic conversion of constituents from Mercurialis perennis L. extracts, which were prepared for such applications. For this purpose, aqueous extracts were inoculated with two Lactobacteria strains, namely Pediococcus sp. (PP1) and Lactobacillus sp. (LP1). Both were isolated from a fermented M. perennis extract and identified by 16S rRNA sequencing. After 1 day of fermentation, an almost complete conversion of the genuine piperidine-2,6-dione alkaloids hermidine quinone (3) and chrysohermidin (4)—both of them being oxidation products of hermidin (1) —was observed by GC-MS analysis, while novel metabolites such as methylhermidin (6) and methylhermidin quinone (7) were formed. Surprisingly, a novel compound plicatanin B (bis-(3-methoxy-1N-methylmaleimide); 8) was detected after 6 days, obviously being formed by ring contraction of 4. An intermediate of a postulated reaction mechanism, isochrysohermidinic acid (14), could be detected by LC-MS. Furthermore, an increase in contents of the metabolite mequinol (4-methoxyphenol; 9) upon fermentation points to a precursor glycoside of 9, which could be subsequently detected by GC-MS after silylation and identified as methylarbutin (15). 15 is described here for M. perennis for the first time.

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Section: Fermentation Of M Perennis With the Lactobacteria Isolates mentioning

confidence: 95%

Section: Enrichment Of Isochrysohermidinic Acid (14) From An Aqueous mentioning

confidence: 99%

Section: Fermentation Of M Perennis With the Lactobacteria Isolates mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Conversion of Plant Secondary Metabolites upon Fermentation of Mercurialis perennis L. Extracts with two Lactobacteria Strains

et al. 2019

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“…Liquidliquid extraction (LLE) [7,9] and solid phase extraction (SPE) [10] are two of the most useful sample preparation methods prior to gas chromatography [11,12], liquid chromatography [4,13,14], or spectroflouorimetric [15] analysis. However, in addition to timeconsuming, tedious, and low sensitivity, LLE often requires large amounts of toxic organic solvents and can be relatively expensive.…”

Section: Introductionmentioning

confidence: 99%

Determination of nicotine, anabasine, and cotinine in urine and saliva samples using single-drop microextraction

Kardani

Daneshfar

Sahrai

2010

Journal of Chromatography B

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Metabolic Fate of Depsides and Alkaloid Constituents in Aqueous Extracts from Mercurialis perennis L. during Fermentation

Lorenz¹,

Conrad²,

Stintzing³

2013

Chemistry & Biodiversity

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Dog's mercury (Mercurialis perennis L.) is an old medicinal plant, nowadays used in complementary medicine. Aqueous fermented extracts of the plant are being mainly applied in remedies to treat external inflammations, but a thorough phytochemical characterization is still lacking. Therefore, the conversion of characteristic compound classes from M. perennis extracts during fermentation and storage was investigated. The microbial transformation of the two main depsides phaselic acid (=(2R)-O-[(E)-caffeoyl]malic acid; 1) and mercurialis acid (=(2R)-[(E)-caffeoyloxy]glutaric acid; 2) was monitored by HPLC-DAD. The degradation followed a second-order kinetic, and the calculated half-life periods of both constituents were 67 and 30 months, respectively. Several depside metabolites were detected by GC/MS in AcOEt extracts as (t) BuMe2 Si (TBDMS) derivatives after derivatization, mainly dihydrocinnamic acids. Moreover, numerous α-hydroxy acids were found, allegedly as degradation products from amino acids or peptides. The microbial alteration of the main alkaloid hermidin was also examined. After three days of fermentation, three novel N-metabolites were formed and thoroughly assigned in CH2 Cl2 extracts as a mixture of 3-ethylhermidin, 3-ethylhermidin quinone, and (E/Z)-3-ethylidenehermidin by GC/MS and NMR methods, as well as by means of total synthesis. A mechanism for the formation of these N-metabolites starting from dimeric hermidin oxidation products is proposed. The obtained results reveal the complex pathways plant constituents may undergo during the fermentation of the extracts.

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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

Cited by 14 publications

References 18 publications

Conversion of Plant Secondary Metabolites upon Fermentation of Mercurialis perennis L. Extracts with two Lactobacteria Strains

Conversion of Plant Secondary Metabolites upon Fermentation of Mercurialis perennis L. Extracts with two Lactobacteria Strains

Determination of nicotine, anabasine, and cotinine in urine and saliva samples using single-drop microextraction

Metabolic Fate of Depsides and Alkaloid Constituents in Aqueous Extracts from Mercurialis perennis L. during Fermentation

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