NMR Analysis of Pulegone in Food Products
Source abstract
Abstract
Pulegone is a monoterpene ketone found in a variety of mint species. It has been classified as possibly carcinogenic to humans (Group 2B) by the International Agency for Research on Cancer (IARC). In previous studies, pulegone in food was analyzed exclusively via GC-MS, while 1H NMR methods were limited to essential oils. The aim of this study was to develop an NMR method for the detection and quantification of pulegone in essential oils and foods. A mixture of methanol-d4/chloroform-d1 in a 1:1 ratio (v/v) was identified as the most effective solvent for separating pulegone signals. The essential oils were subjected to analysis at this solvent-mixture ratio. The extraction of pulegone was required for food analysis, and the steam distillation method proved to be more effective than the ultrasonic-assisted extraction method. The highest pulegone concentrations were identified in pennyroyal oil and muña oil, whereas lower levels were observed in other matrices, including corn mint oil and select food items. A toxicological assessment showed that the amount consumed did not exert any adverse effects on human health.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Phytochemistry and Biological Activities · Essential Oils and Antimicrobial Activity · Natural product bioactivities and synthesis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Chemisches und Veterinäruntersuchungsamt (CVUA) Karlsruhe, Weissenburger Strasse 3, 76187 Karlsruhe, Germany
Department of Food Chemistry and Phytochemistry, Institute of Applied Biosciences, Karlsruhe Institute of Technology (KIT), Adenauerring 20a, 76131 Karlsruhe, Germany
References (37)
Show source-provided references
1. Chemical composition of the essential oil and isolation of two main constituents of Mentha pulegium L.10.1007/s42535-023-00572-x ↗
2. Comparative Analysis of Chemical Compositions of Mentha L. Plant Extracts by Gas Chromatography–Mass Spectrometry after Hydrodistillation and Subcritical Extraction10.1134/S1061934823090095 ↗
3. Environmental variation on aroma components of pulegone/piperitone rich spearmint (Mentha spicata L.)10.1016/j.indcrop.2010.07.009 ↗
4. Chemotaxonomy of Commercial Buchu Species (Agathosma betulina and A. crenulata)10.1080/10412905.1996.9700607 ↗
5. New insights into the chemical biodiversity of Minthostachys mollis in Argentina10.1016/j.bse.2014.09.004 ↗
6. The Biological Activity and Essential Oil Composition of 17 Agathosma (Rutaceae) Species10.1080/10412905.2006.12067112 ↗
7. Quantitative determination of pulegone in pennyroyal oil by FT-IR spectroscopy10.1021/jf9026052 ↗
8. Chemical composition, antioxidant activity and acetylcholinesterase inhibitory of wild Mentha species from northeastern Algeria10.1016/j.sajb.2018.03.002 ↗
9. Chemical composition, antimicrobial, and cytotoxic properties of five Lamiaceae essential oils10.1016/j.indcrop.2014.07.011 ↗
10. Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products10.1080/02652030500041581 ↗
11. Assessment of phytochemical and agro-morphological variability among different wild accessions of Mentha longifolia L. cultivated in field condition10.1016/j.indcrop.2019.111698 ↗
12. Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae)10.1080/14786410903108944 ↗
13. Composition and chemical variability of Mentha suaveolens ssp. suaveolens and M. suaveolens ssp. insularis from Corsica10.1002/cbdv.200900365 ↗
14. Variation of essential oil of Mentha haplocalyx Briq. and Mentha spicata L. from China10.1016/j.indcrop.2012.06.010 ↗
15. Statista (2024, February 17). Absatz von Kräuter- und Früchtetee in Deutschland nach Art in den Jahren 2016 bis 2018 (in Tonnen). Available online: https://de.statista.com/statistik/daten/studie/38232/umfrage/fruechtetee-und-kraeutertee-konsum-in-deutschland/.
16. Peter, K.V. (2012). Mint. Handbook of Herbs and Spices, Woodhead Publishing.10.1533/9780857095671 ↗
17. A straightforward method to determine flavouring substances in food by GC-MS10.1016/j.foodchem.2014.11.011 ↗
18. NTP (2011). Toxicological and Carcinogensis Studies of Pulegone (CAS No. 89-82-7) in F344/N Rats and B6C3F1 Mice (Gavage Studies). Natl. Toxicol. Program Tech. Rep. Ser., 563, 1–201.
19. European Commission (2008). 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. EU, L354, 34–50.
20. Speijers, G.J.A. (2024, July 02). IPCS 2001 WHO Food Additives Series 46: Pulegone and Related Substances. Available online: http://www.inchem.org/documents/jecfa/jecmono/v46je10.htm.
21. European Medicines Agency (2024, March 29). Committee on Herbal Medicinal Products, Public Statement on the Use of Herbal Medicinal Products Containing Pulegone and Menthofuran, Available online: https://www.ema.europa.eu/en/documents/scientific-guideline/public-statement-use-herbal-medicinal-products-containing-pulegone-and-menthofuran-revision-1_en.pdf.
22. Comparison of GC/MS and NMR for quantification of methyleugenol in food10.1007/s00217-012-1879-4 ↗
23. O’Neil, M.J. (2013). The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals, Merck Sharp & Dohme Corp., RSC Publishing. [15th ed.].
24. (2024, March 29). Safety Data Sheet: (+)-Pulegon. Available online: https://www.carlroth.com/medias/SDB-5168-MT-EN.pdf.
25. (2024, March 27). Sicherheitsdatenblatt–Cyclohexan. Available online: https://www.sigmaaldrich.com/DE/de/sds/sial/28920.
26. (2024, March 27). Sicherheitsdatenblatt–Chloroform-d. Available online: https://www.sigmaaldrich.com/DE/de/sds/aldrich/151823.
27. Green Chemistry: Principles and Practice10.1039/B918763B ↗
28. (2017). Spices, Condiments and Herbs—Determination of Volatile Oil Content (Hydrodistillation Method) (Standard No. ISO 6571:2008/Amd 1:2017).
29. Current status, technology, regulation and future perspectives of essential oils usage in the food and drink industry10.1002/jsfa.12695 ↗
30. Chemical composition and antimicrobial activity of bergamot-mint (Mentha citrata Ehrh.) essential oils isolated from the herbage and aqueous distillate using different methods10.1016/j.indcrop.2016.07.005 ↗
31. Mentha spicata Essential Oil: Chemical Composition, Antioxidant and Antibacterial Activities against Planktonic and Biofilm Cultures of Vibrio spp. Strains10.3390/molecules200814402 ↗
32. BBC (2024, April 02). Rack of Lamb with Sauce Paloise. Available online: https://www.bbc.co.uk/food/recipes/rack_of_lamb_with_sauce_31777.
33. BBC (2024, April 02). Beef Shin Stew with Spiced Sweet Potato Dumplings and Couscous. Available online: https://www.bbc.co.uk/food/recipes/beef_shin_couscous_with_51409.
34. Voigt, V., Franke, H., and Lachenmeier, D.W. (2024). Risk Assessment of Pulegone in Foods Based on Benchmark Dose–Response Modeling. Foods, 13.10.3390/foods13182906 ↗
35. Measuring protein concentrations by NMR spectroscopy10.1021/ja055336t ↗
36. Claridge, T.D. (2016). High-Resolution NMR Techniques in Organic Chemistry, Elsevier Science. [3rd ed.].
37. Kromidas, S. (2011). Handbuch Validierung in der Analytik, Wiley-VCH-Verlag. [2nd ed.].