Site-specific 13C content by quantitative isotopic 13C Nuclear Magnetic Resonance spectrometry: A pilot inter-laboratory study

Chaintreau, Alain; Fieber, Wolfgang; Sommer, Horst; Gilbert, Alexis; Yamada, Keita; Yoshida, Naohiro; Pagelot, A.; Moskau, Detlef; Moreno, Aitor; Schleucher, Jürgen; Reniero, Fabiano; Holland, Margaret V.; Guillou, Claude; Silvestre, Virginie; Akoka, Serge; Remaud, Gérald S.

doi:10.1016/j.aca.2013.06.004

Cited by 40 publications

(41 citation statements)

References 20 publications

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“…The sensibility and precision of the technique were then demonstrated by obtaining the intramolecular 13 C isotopic composition . The robustness of the method was shown during a preliminary ring test for which vanillin samples were used on a routine basis, with the analysis time reduced to less than 8 hours for five spectra . During this work, a qualification test performed on eight spectrometers demonstrated an average of 0.9–1.2‰ for intra‐variability, with the highest value of 2.1‰ obtained for inter‐variability.…”

Section: Introductionmentioning

confidence: 85%

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Guyader

Thomas

Jamin

et al. 2019

Flavour & Fragrance J

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Synthetic vanillin is the flavouring most used in agro‐food industries, but more and more frequently consumers are now turning to natural origin. Vanilla planifolia (Andrews) is the most commercialized species of pods in the world and is mainly produced in Madagascar. However, periodically the production of V. planifolia suffers from poor climatic conditions, with the resulting degradation of both the quality and the quantity of the pods. Consequently, the price of vanilla pods rose to record in 2017 and the risk of fraud has increased in response. Analytical methods based on isotopic compositions have already proven their ability to ensure the authenticity of natural vanillin. In 2006, 2H SNIF‐NMR (site‐specific natural isotopic fractionation by nuclear magnetic resonance) was approved as official method by the Association of Official Analytical Chemists (AOAC 2006.05). However, this method is time consuming and the extraction of 1 g is cumbersome for the finished products. The information brought by combined 2H and 13C SNIF‐NMR profiles was compared using chemometric tools to determine the best routine tool to improve both the global analysis time and the potential of detection. As a result of this work the ability of the SNIF‐NMR method to verify the authenticity of vanillin has been improved, in particular by providing the first means to discern the geographical origin of vanilla pods. Furthermore, 13C NMR using pulse sequences such as INEPT (insensitive nuclei enhanced by polarization transfer) offers the possibility to improve the sensitivity of the analysis, with a reduced quantity of product (less than 50 mg) and a shorter analysis time, which will facilitate the study of the finished matrices as well as clearly discriminating the origins of the vanilla flavourings.

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Section: Introductionmentioning

confidence: 85%

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Guyader

Thomas

Jamin

et al. 2019

Flavour & Fragrance J

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“…Spectral Data Processing-The positional isotopic distribution in ethanol was obtained from the iq- 13 C NMR spectrum essentially as described previously (9,22). To obtain S i , the area under the 13 C signal for the C-atom in position i (in this case the methyl and methylene positions), curve fitting based on a total line shape analyses (deconvolution) is carried out with a Lorentzian mathematical model using Perch TM NMR Software.…”

mentioning

confidence: 99%

Nonstatistical 13C Distribution during Carbon Transfer from Glucose to Ethanol during Fermentation Is Determined by the Catabolic Pathway Exploited

Bayle

Akoka

Remaud

et al. 2015

Journal of Biological Chemistry

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Background: Different fermentation pathways should lead to distinctive isotope patterns in the products. Results: Three pathways for glucose catabolism show discrete isotope patterns in ethanol. Conclusion: Catabolism by different enzyme sequences leads to differential isotope redistribution patterns. Significance: Learning how isotope fractionation occurs in nature is crucial for interpreting fractionation during biochemical and physical processes for traceability.

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“…Focusing first on the δ 13 C i pattern of the aromatic ring of tramadol, it is apparent that the C4′ T , C5′ T , and C6′ T have values closely related to those obtained from vanillin and ferulic acid (16,45,46), derived from L-Phe, despite the different compounds having been obtained from different plants and from different geographical areas. However, at the C1′ T , and C2′ T positions, the match is less evident, whereas the C3′ T is distinguished by being very impoverished relative to the equivalent position of the other 3-hydroxylated compounds.…”

Section: Resultsmentioning

confidence: 99%

“…Each measurement consisted of the average of five independently recorded NMR spectra. In addition, a quantitative 13 C NMR reference spectrum was recorded on a Bruker 400 Avance III spectrometer fitted with a BBFO+ probe carefully tuned to the recording frequency of 100.62 MHz, which was used to calibrate the 500-MHz spectrometer (46,55).…”

Section: H Nmrmentioning

confidence: 99%

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

Romek

Nun

Remaud

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Tramadol, previously only known as a synthetic analgesic, has now been found in the bark and wood of roots of the African medicinal tree Nauclea latifolia. At present, no direct evidence is available as to the biosynthetic pathway of its unusual skeleton. To provide guidance as to possible biosynthetic precursors, we have adopted a novel approach of retro-biosynthesis based on the position-specific distribution of isotopes in the extracted compound. Relatively recent developments in isotope ratio monitoring by 13 C NMR spectrometry make possible the measurement of the nonstatistical position-specific natural abundance distribution of 13 C (δ 13 C i ) within the molecule with better than 1‰ precision. Very substantial variation in the 13 C positional distribution is found: between δ 13 C i = −11 and −53‰. Distribution is not random and it is argued that the pattern observed can substantially be interpreted in relation to known causes of isotope fractionation in natural products. Thus, a plausible biosynthetic scheme based on sound biosynthetic principals of precursorsubstrate relationships can be proposed. In addition, data obtained from the 18 O/ 16 O ratios in the oxygen atoms of the compound add support to the deductions made from the carbon isotope analysis. This paper shows how the use of 13 C NMR at natural abundance can help with proposing a biosynthetic route to compounds newly found in nature or those difficult to tackle by conventional means.NMR spectrometry | position-specific isotope analysis | retro-biosynthesis | tramadol | Nauclea latifolia

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Site-specific 13C content by quantitative isotopic 13C Nuclear Magnetic Resonance spectrometry: A pilot inter-laboratory study

Cited by 40 publications

References 20 publications

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Nonstatistical 13C Distribution during Carbon Transfer from Glucose to Ethanol during Fermentation Is Determined by the Catabolic Pathway Exploited

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

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Site-specific 13C content by quantitative isotopic 13C Nuclear Magnetic Resonance spectrometry: A pilot inter-laboratory study

Cited by 40 publications

References 20 publications

Combination of 13C and 2H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Combination of 13C and 2H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Nonstatistical 13C Distribution during Carbon Transfer from Glucose to Ethanol during Fermentation Is Determined by the Catabolic Pathway Exploited

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

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Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors