16-O-methylcafestol is present in ground roast Arabica coffees: Implications for authenticity testing

Gunning, Yvonne; Defernez, Marianne; Watson, Andrew D.; Beadman, Niles; Colquhoun, Ian J.; Gall, Gwénaëlle Le; Philo, Mark; Garwood, Hollie; Williamson, D.S.; Davis, Aaron P.; Kemsley, E. Kate

doi:10.1016/j.foodchem.2017.12.034

Cited by 62 publications

(58 citation statements)

References 27 publications

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“…The discrimination between 16-OMC and 16-OMK cannot be achieved using NMR methods, 14 and then, both the quantification of In order to perform preliminary 16-OMK quantification, we investigated a green Arabusta coffee sample. Due to the pedigree of this interspecific coffee hybrid, a reasonably high content of 16-OMD may be expected, also in view of reported data.…”

Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

“…Due to the pedigree of this interspecific coffee hybrid, a reasonably high content of 16-OMD may be expected, also in view of reported data. 14,22,23 In this case, the amount determined in a few Arabica samples analyzed so far. 24,25 Moreover, 1641 ± 164 mg/kg is the reported average 16-OMC content found in a wide range of green Robusta commercial samples, 7 and this value is within the wider range from 600 to 1800 mg/kg reported by Belitz et al, 26 which include the Arabusta 16-OMD content reported in the literature.…”

Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

“…24,25 Moreover, 1641 ± 164 mg/kg is the reported average 16-OMC content found in a wide range of green Robusta commercial samples, 7 and this value is within the wider range from 600 to 1800 mg/kg reported by Belitz et al, 26 which include the Arabusta 16-OMD content reported in the literature. 14,22,23 In the case of Arabica, the total 16-OMD content determined by NMR in several samples of roasted Arabica cultivars was found to be <20 mg/kg, 14 and very recently for this coffee species, a guidance value of 16-OMC content <50 mg/kg was used for authentication purposes. 27 As far as the relative proportion of the two 16-OMD is concerned, the obtained data indicate that 16-OMC accounts for approximately 90% of the total 16-OMD present in the analyzed green Arabusta coffee.…”

Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

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16‐O‐Methylated diterpenes in green Coffea arabica: ultra‐high‐performance liquid chromatography‐tandem mass spectrometry method optimization and validation

Guercia

Colomban

Navarini³

2020

J Mass Spectrom

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Coffee diterpenes are the main constituents of the coffee oil unsaponifiable fraction. The three most important diterpenes are cafestol, kahweol, and 16-O-methylcafestol (16-OMC), and they are produced, except for cafestol, only by plants of the Coffea genus. Recently, in addition to these three major diterpenes, another 16-Omethylated diterpene (16-O-methylkahweol: 16-OMK) has been identified and quantified, for the first time, in Robusta coffee. For many years, 16-OMC has been considered present exclusively in Robusta, and so it has been reputed an excellent authenticity marker for the presence of Robusta in coffee products. For its quantification, nuclear magnetic resonance (NMR) has proved very useful when compared with other methods. Quite recently, the detection of very low levels of the two 16-O-methylated diterpenes (16-OMD) 16-OMC and 16-OMK in roasted Arabica was reported. This finding makes the use of NMR methods in 16-OMD quantification in Arabica coffee particularly challenging in view of both the trace amounts of 16-OMD and the impossibility to discriminate between 16-OMC and 16-OMK. The ultra-high performance liquid chromatography mass spectrometry (UHPLC-MS) method, already used to detect 16-OMC and 16-OMK in Arabica roasted coffee, is then more suitable for quantitative analyses. Up to now however, no quantification of coffee 16-OMD via ultra-high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) has been carried out; this largely stimulated the present study. For the first time, a simple procedure for the quantitative detection of 16-OMD in Arabica coffee has been developed, and as far as 16-OMC is concerned, fully validated in terms of specificity, linearity, concentration range, limit of detection (LOD), limit of quantification (LOQ), and repeatability following the criteria specified in the EU Commission Decision 2002/675/EC. This method proved to be very specific and sensitive. In order to avoid the chemical complexity generated by the roasting process, the method was optimized and validated on several green Arabica samples from different geographical origins.

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Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

Section: -Omk Detection and Preliminary Quantificationmentioning

confidence: 99%

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16‐O‐Methylated diterpenes in green Coffea arabica: ultra‐high‐performance liquid chromatography‐tandem mass spectrometry method optimization and validation

Guercia

Colomban

Navarini³

2020

J Mass Spectrom

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“…This large variability unfortunately prevents the use of 16‐OMC to quantify C. canephora in unknown roasted coffee blends. With the same aim, in contrast with previous studies, Gunning et al highlighted the concomitant presence of 16‐OMC and 16‐OMK (16‐O‐methyl kahweol) in both arabica and robusta, due to a peak at 3.16 ppm in the 1 H NMR spectra, thanks to an improved sample preparation procedure. In the present study, the lipophilic fraction was obtained by extracting 10 g of ground sample with 30 ml of chloroform and stirring at 600 rpm for 5 min.…”

Section: Application Of Nmr‐based Metabolomics In Food Science and Aumentioning

confidence: 99%

The potentiality of NMR‐based metabolomics in food science and food authentication assessment

Consonni

Cagliani

2018

Magnetic Reson in Chemistry

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In the last years, there was an increasing interest on nuclear magnetic resonance (NMR) spectroscopy, whose applications experienced an exponential growth in several research fields, particularly in food science. NMR was initially developed as the elective technique for structure elucidation of single molecules and nowadays is playing a dominant role in complex mixtures investigations. In the era of the “omics” techniques, NMR was rapidly enrolled as one of the most powerful methods to approach metabolomics studies. Its use in analytical routines, characterized by rapid and reproducible measurements, would provide the identification of a wide range of chemical compounds simultaneously, disclosing sophisticated frauds or addressing the geographical origin, as well as revealing potential markers for other authentication purposes. The great economic value of high‐quality or guaranteed foods demands highly detailed characterization to protect both consumers and producers from frauds. The present scenario suggests metabolomics as the privileged approach of modern analytical studies for the next decades. The large potentiality of high‐resolution NMR techniques is here presented through specific applications and using different approaches focused on the authentication process of some foods, like tomato paste, saffron, honey, roasted coffee, and balsamic and traditional balsamic vinegar of Modena, with a particular focus on geographical origin characterization, ageing determination, and fraud detection.

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“…The unsaponifiable matter from Robusta presents cafestol and 16-O-methylcafestol as the two main components but the latter is stable during the roasting process. 16-O-methylcafestol has been considered a good chemical marker for detecting Robusta in coffee blends [2] for a long time until than it was detected also in Arabica roasted coffee [3]. However, the presence in Arabica of 16-O-methylcafestol in trace amounts makes this compound still a very useful chemical marker for authentication purposes.…”

Section: Introductionmentioning

confidence: 99%

Interaction of the Coffee Diterpenes Cafestol and 16-O-Methyl-Cafestol Palmitates with Serum Albumins

Berti

Navarini²,

Guercia³

et al. 2020

IJMS

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The main coffee diterpenes cafestol, kahweol, and 16-O-methylcafestol, present in the bean lipid fraction, are mostly esterified with fatty acids. They are believed to induce dyslipidaemia and hypercholesterolemia when taken with certain types of coffee brews. The study of their binding to serum albumins could help explain their interactions with biologically active xenobiotics. We investigated the interactions occurring between cafestol and 16-O-methylcafestol palmitates with Bovine Serum Albumin (BSA), Human Serum Albumin (HSA), and Fatty Free Human Serum Albumin (ffHSA) by means of circular dichroism and fluorimetry. Circular Dichroism (CD) revealed a slight change (up to 3%) in the secondary structure of fatty-free human albumin in the presence of the diterpene esters, suggesting that the aliphatic chain of the palmitate partly occupies one of the fatty acid sites of the protein. A warfarin displacement experiment was performed to identify the binding site, which is probably close but not coincident with Sudlow site I, as the affinity for warfarin is enhanced. Fluorescence quenching titrations revealed a complex behaviour, with Stern–Volmer constants in the order of 103–104 Lmol−1. A model of the HSA-warfarin-cafestol palmitate complex was obtained by docking, and the most favourable solution was found with the terpene palmitate chain inside the FA4 fatty acid site and the cafestol moiety fronting warfarin at the interface with site I.

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16-O-methylcafestol is present in ground roast Arabica coffees: Implications for authenticity testing

Cited by 62 publications

References 27 publications

16‐O‐Methylated diterpenes in green Coffea arabica: ultra‐high‐performance liquid chromatography‐tandem mass spectrometry method optimization and validation

16‐O‐Methylated diterpenes in green Coffea arabica: ultra‐high‐performance liquid chromatography‐tandem mass spectrometry method optimization and validation

The potentiality of NMR‐based metabolomics in food science and food authentication assessment

Interaction of the Coffee Diterpenes Cafestol and 16-O-Methyl-Cafestol Palmitates with Serum Albumins

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