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Authenticity Control of Natural Products by Stable Isotope Ratio Analysis

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Biotechnology of Natural Products

Abstract

This chapter provides an overview about new and well established strategies regarding the authenticity control of natural products by stable isotope ratio analysis (SIRA). To date, isotope ratio mass spectrometry (IRMS) and site-specific natural abundance isotope fractionation-nuclear magnetic resonance spectroscopy (SNIF-NMR) are methods that are employed for this purpose and are discussed together with practical applications of SIRA on miscellaneous natural products that can be produced chemosynthetically and biotechnologically like phenylpropanoids (vanillin), terpenes (linalool, citral, carotenoids), polyphenols (resveratrol) and alkaloids (caffeine).

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Abbreviations

BSIA:

Bulk stable isotope analysis

CAM:

Crassulacean acid metabolism

CSIA:

Compound-specific isotope ratio analysis

EA:

Elemental analyzer

GC:

Gas chromatography

HT-RPLC:

High-temperature reversed-phase liquid chromatography

IRMS:

Isotope ratio mass spectrometry

LC:

Liquid chromatography

PSIA:

Position specific isotope analysis

SIRA:

Stable isotope ratio analysis

SNIF-NMR:

Site-specific natural abundance isotope fractionation-nuclear magnetic resonance spectroscopy

TMU:

Tetramethyl urea

References

  1. Arbeitsgruppe Aromastoffe. Lebensmittelchemische Gesellschaft der Gesellschaft Deutscher Chemiker. Grundlagenpapier ‘Herkunft und Authentizität von Vanillearomen’ [Internet]. 2016 [cited 2016 Oct 4]. Available from: https://www.gdch.de/fileadmin/downloads/Netzwerk_und_Strukturen/Fachgruppen/Lebensmittelchemiker/Arbeitsgruppen/aromastoffe/vanille_aroma.pdf

  2. Bayle K, Grand M, Chaintreau A, Robins RJ, Fieber W, Sommer H, et al. Internal referencing for 13C position-specific isotope analysis measured by NMR spectrometry. Anal Chem. 2015;87(15):7550–4.

    Article  CAS  Google Scholar 

  3. Bensaid FF, Wietzerbin K, Martin GJ. Authentication of natural vanilla flavorings: isotopic characterization using degradation of vanillin into guaiacol. J Agric Food Chem. 2002;50(22):6271–5.

    Article  Google Scholar 

  4. Bononi M, Quaglia G, Tateo F. Easy extraction method to evaluate δ13C vanillin by liquid chromatography–isotopic ratio mass spectrometry in chocolate bars and chocolate snack foods. J Agric Food Chem. 2015;63(19):4777–81.

    Article  CAS  Google Scholar 

  5. Brenna JT. Natural intramolecular isotope measurements in physiology: elements of the case for an effort toward high-precision position-specific isotope analysis. Rapid Commun Mass Spectrom. 2001;15(15):1252–62.

    Article  CAS  Google Scholar 

  6. Corso TN, Brenna JT. High-precision position-specific isotope analysis. Proc Natl Acad Sci. 1997;94(4):1049–53.

    Article  CAS  Google Scholar 

  7. Danho D, Naulet N, Martin GJ. Deuterium, carbon and nitrogen isotopic analysis of natural and synthetic caffeines. Authentication of coffees and coffee extracts. Analusis. 1992;20(3):179–84.

    CAS  Google Scholar 

  8. Dias RF, Freeman KH, Franks SG. Gas chromatography–pyrolysis–isotope ratio mass spectrometry: a new method for investigating intramolecular isotopic variation in low molecular weight organic acids. Org Geochem. 2002;33(2):161–8.

    Article  CAS  Google Scholar 

  9. Diomande DG, Martineau E, Gilbert A, Nun P, Murata A, Yamada K, et al. Position-specific isotope analysis of Xanthines: a 13C nuclear magnetic resonance method to determine the 13C intramolecular composition at natural abundance. Anal Chem. 2015;87(13):6600–6.

    Article  CAS  Google Scholar 

  10. European Union. Regulation (EC) No 1334/2008 of the European Parliament and of the Council of 16 December 2008 on flavourings and certain food ingredients with flavouring properties for use in and on foods and amending Council Regulation (EEC) No 1601/91, Regulations (EC) No 2232/96 and (EC) No 110/2008 and Directive 2000/13/EC. Off J Eur Union. 2008;51:34–50.

    Google Scholar 

  11. Fronza G, Fuganti C, Serra S, Cisero M, Koziet J. Stable isotope labeling pattern of resveratrol and related natural stilbenes. J Agric Food Chem. 2002;50(10):2748–54.

    Article  CAS  Google Scholar 

  12. Gallage NJ, Møller BL. Vanillin–bioconversion and bioengineering of the most popular plant flavor and its de novo biosynthesis in the vanilla orchid. Mol Plant. 2015;8(1):40–57.

    Article  CAS  Google Scholar 

  13. Gassenmeier K, Binggeli E, Kirsch T, Otiv S. Modulation of the 13C/12C ratio of vanillin from vanilla beans during curing. Flavour Fragr J. 2013;28(1):25–9.

    Article  CAS  Google Scholar 

  14. Godin JP, Breuillé D, Obled C, Papet I, Schierbeek H, Hopfgartner G, Fay LB. Liquid and gas chromatography coupled to isotope ratio mass spectrometry for the determination of 13C-valine isotopic ratios in complex biological samples. J Mass Spectrom. 2008;43(10):1334–43.

    Article  CAS  Google Scholar 

  15. Greule M, Tumino LD, Kronewald T, Hener U, Schleucher J, Mosandl A, et al. Improved rapid authentication of vanillin using δ13C and δ2H values. Eur Food Res Technol. 2010;231(6):933–41.

    Article  CAS  Google Scholar 

  16. Hanneguelle S, Thibault JN, Naulet N, Martin GJ. Authentication of essential oils containing linalool and linalyl acetate by isotopic methods. J Agric Food Chem. 1992;40(1):81–7.

    Article  CAS  Google Scholar 

  17. Hansen A-MS, Fromberg A, Frandsen HL. Authenticity and traceability of vanilla flavors by analysis of stable isotopes of carbon and hydrogen. J Agric Food Chem. 2014;62(42):10326–31.

    Article  CAS  Google Scholar 

  18. Hener U, Brand WA, Hilkert AW, Juchelka D, Mosandl A, Podebrad F. Simultaneous on-line analysis of 18O/16O and 13C/12C ratios of organic compounds using GC-pyrolysis-IRMS. Z Für Leb Forsch A. 1998;206(3):230–2.

    Article  CAS  Google Scholar 

  19. Hübschmann H-J. Handbook of GC-MS: fundamentals and applications. Weinheim: Wiley; 2015.

    Book  Google Scholar 

  20. Jochmann MA, Schmidt TC. Compound-specific stable isotope analysis. Cambridge: Royal Society of Chemistry; 2012.

    Google Scholar 

  21. Kaunzinger A, Juchelka D, Mosandl A. Progress in the authenticity assessment of vanilla. 1. Initiation of authenticity profiles. J Agric Food Chem. 1997;45(5):1752–7.

    Article  CAS  Google Scholar 

  22. Kempe K, Kohnen M. Deterioration of natural vanilla flavours in dairy products during processing. Adv Food Sci. 1999;21(1–2):48–53.

    CAS  Google Scholar 

  23. Kroll H, Friedrich J, Menzel M, Schreier P. Carbon and hydrogen stable isotope ratios of carotenoids and β-carotene-based dietary supplements. J Agric Food Chem. 2008;56(11):4198–204.

    Article  CAS  Google Scholar 

  24. Martin G, Remaud G, Martin GJ. Isotopic methods for control of natural flavours authenticity. Flavour Fragr J. 1993;8(2):97–107.

    Article  CAS  Google Scholar 

  25. Martin GJ, Heck G, Djamaris-Zainal R, Martin ML. Isotopic criteria in the characterization of aromatic molecules. 1. Hydrogen affiliation in natural benzenoid/phenylpropanoid molecules. J Agric Food Chem. 2006;54(26):10112–9.

    Article  CAS  Google Scholar 

  26. Martin GJ, Lavoine-Hanneguelle S, Mabon F, Martin ML. The fellowship of natural abundance 2H-isotopomers of monoterpenes. Phytochemistry. 2004;65(20):2815–31.

    Article  CAS  Google Scholar 

  27. Nhu-Trang T-T, Casabianca H, Grenier-Loustalot M-F. Authenticity control of essential oils containing citronellal and citral by chiral and stable-isotope gas-chromatographic analysis. Anal Bioanal Chem. 2006;386(7–8):2141–52.

    Article  CAS  Google Scholar 

  28. Remaud GS, Akoka S. A review of flavors authentication by position-specific isotope analysis by nuclear magnetic resonance spectrometry: the example of vanillin. Flavour Fragr J. 2017;32(2):77–84.

    Article  Google Scholar 

  29. Remaud GS, Martin Y-L, Martin GG, Martin GJ. Detection of sophisticated adulterations of natural vanilla flavors and extracts: application of the SNIF-NMR method to vanillin and p-hydroxybenzaldehyde. J Agric Food Chem. 1997;45(3):859–66.

    Article  CAS  Google Scholar 

  30. Rozin P. The meaning of ‘natural’ process more important than content. Psychol Sci. 2005;16(8):652–8.

    Article  Google Scholar 

  31. Rozin P, Spranca M, Krieger Z, Neuhaus R, Surillo D, Swerdlin A, et al. Preference for natural: instrumental and ideational/moral motivations, and the contrast between foods and medicines. Appetite. 2004;43(2):147–54.

    Article  Google Scholar 

  32. Schäfer U, Kiefl J, Geißler T, Geißler K, Kassing M, Ley J, et al. Recent advances in the authenticity control of bioflavours. Biofavour 2015 – book Abstr. Frankfurt/Main: Dechema e.V; 2015. p. 53.

    Google Scholar 

  33. Scharrer A. Vanille : Neues zur Authentizität [Internet]. [Franfurt am Main]: Universität Frankfurt am Main; 2002 [cited 2016 Oct 4]. Available from: http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/5451/

  34. Schmidt H-L. Fundamentals and systematics of the non-statistical distributions of isotopes in natural compounds. Naturwissenschaften. 2003;90(12):537–52.

    Article  CAS  Google Scholar 

  35. Schmidt H-L, Mosandl A, Schreier P, Roßmann A, Werner RA. Stable isotope ratio analysis in quality control of flavourings. In: Ziegler H, editor. Flavourings: production, composition, applications, regulations. Weinheim:Wiley-VCH; 2007.

    Google Scholar 

  36. Schmidt H-L, Werner RA, Eisenreich W. Systematics of 2H patterns in natural compounds and its importance for the elucidation of biosynthetic pathways. Phytochem Rev. 2003;2(1–2):61–85.

    Article  CAS  Google Scholar 

  37. Schmidt H-L, Werner RA, Roßmann A. 18O pattern and biosynthesis of natural plant products. Phytochemistry. 2001;58(1):9–32.

    Article  CAS  Google Scholar 

  38. Surburg H, Panten J. Common fragrance and flavor materials: preparation, properties and uses. Weinheim: Wiley; 2016.

    Book  Google Scholar 

  39. Tenailleau EJ, Lancelin P, Robins RJ, Akoka S. Authentication of the origin of vanillin using quantitative natural abundance 13C NMR. J Agric Food Chem. 2004;52(26):7782–7.

    Article  CAS  Google Scholar 

  40. Weckerle B, Richling E, Heinrich S, Schreier P. Origin assessment of green coffee (Coffea arabica) by multi-element stable isotope analysis of caffeine. Anal Bioanal Chem. 2002;374(5):886–90.

    Article  CAS  Google Scholar 

  41. Zhang L, Kujawinski DM, Federherr E, Schmidt TC, Jochmann MA. Caffeine in your drink: natural or synthetic? Anal Chem. 2012;84(6):2805–10.

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Bioanalytics, Institute of Nutritional and Food Sciences (IEL), University of Bonn, Endenicher Allee 11-13, 53115, Bonn, Germany

    Matthias Wüst

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  1. Matthias Wüst
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Correspondence to Matthias Wüst .

Editor information

Editors and Affiliations

  1. Biotechnology of Natural Products, Technische Universität München, Freising, Germany

    Wilfried Schwab

  2. Institute of Biological Chemistry and M.J. Murdock Metabolomics Laboratory, Washington State University, Pullman, Washington, USA

    Bernd Markus Lange

  3. Bioanalytics, Institute of Nutritional and Food Sciences (IEL), University of Bonn, Bonn, Germany

    Matthias Wüst

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Wüst, M. (2018). Authenticity Control of Natural Products by Stable Isotope Ratio Analysis. In: Schwab, W., Lange, B., Wüst, M. (eds) Biotechnology of Natural Products. Springer, Cham. https://doi.org/10.1007/978-3-319-67903-7_10

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