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Mass Spectrometry Based Investigation of Chlorogenic Acid Reactivity and Profile in Model Systems and Coffee Processing

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Mass Spectrometry Based Investigation of Chlorogenic Acid Reactivity and Profile in Model Systems and Coffee Processing Mass Spectrometry Based Investigation of Chlorogenic Acid Reactivity and Profile in Model Systems and Coffee Processing by Sagar Deshpande A Thesis submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Approved Dissertation Committee Prof. Dr. Nikolai Kuhnert (Chair) Prof. Dr. Gerd-Volker Röschenthaler (Reviewer) Prof. Dr. Michael N. Clifford (External Reviewer) Date of Defense: 24th January 2014 School of Engineering and Science Abstract Beneficial health and biological effects of coffee as well as its sensory properties are largely associated with chlorogenic acids (CGAs) since; coffee is the richest dietary source of CGAs and their derivatives. From green coffee beans to the beverage, chemical components of the green coffee undergo enormous transformations, which have been studied in great details in the past. Roasted coffee melanoidines are extensively contributed by the products formed by the most relevant secondary metabolite- chlorogenic acids. For every 1% of the dry matter of the total CGA content in the green coffee beans, 8-10% of the original CGAs are transformed or decomposed into respective derivatives of cinnamic acid and quinic acid. The non-volatile fraction of the roasted coffee remains relatively unravelled in the aspects of its chemistry and structural information. Coffee roasting, along with the other processes brings about considerable changes in the chlorogenic acid profile of green coffee through number of chemical processes. In roasting, chlorogenic acids evidently undergo various processes such as, acyl group migration, transesterification, thermal trans-cis isomerization, dehydration and epimerization. To understand the chemistry behind roasted coffee melanoidines, it is of utmost importance to study the changes occurring in CGAs and their derivatives through food processing. The isomeric transformations of the chlorogenic acids resulting due to the migration of hydroxycinnamoyl group from any of the four hydroxyl groups of quinic acid to another have been thoroughly investigated in this work by LC-MSn. In this thesis, the acyl migration phenomenon under the treatment of tetramethylammonium hydroxide (TMAH) hydrolysis, model roasting experiments and by brewing at pH 5 (water reflux, 5 h) of the seven commercially available mono- and di-caffeoylqunic acids was studied in detail. Intermolecular acyl migration (transesterification) was also studied by tetramethylammonium hydroxide (TMAH) hydrolysis and model roasting experiments in between 5-CQA and p- coumaric acid as well as in 5-CQA and ferulic acid. In this thesis, four diastereoisomers of quinic acid have been synthesized selectively, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid and scyllo-quinic acid by applying appropriate hydroxyl group protection and deprotection strategies in order to study their behavior in LC-MSn along with commercially available (-)-quinic acid. We report for the first time that these diastereoisomers are distinguishable on the basis of their fragmentation behavior as well as their chromatographic elution order. In this study, we also observed that i muco-quinic acid, scyllo-quinic acid and epi-quinic acid are present in hydrolyzed Guatemala roasted coffee sample as possible products of roasting. The synthetic work accomplished in present work will provide for the generation of the reference standards to identify remaining epimers of CGAs in roasted coffee. Considering the fact that relatively large amount of the degradation products of CGAs such as, quinic acid, caffeic acid along with the most prominent member of the CGAs profile in roasted coffee, 5-caffeoylquinic acid itself are present in the roasted coffee along with free small, non-volatile organic acids, we examined in details the further esterification phenomenon among themselves. To investigate transesterification in roasted coffee in details we designed a thorough analytical plan involving four experiments. A selection of small organic acids were heated in the presence of 5-CQA to check if simulated roasting conditions facilitate the formation of the transesterification, caffeic acid and quinic acid with the mixture of all the organic acids separately to check, which of the organic acid show greater affinity towards the formation of the condensed esters. With the experimental results in hand, we then identified transesterification products in different roasted coffee samples by LC-MSn, LC- TOF-MS and FT-ICR-MS. Data generated by different analytical techniques such as, NMR-, CD-, IR spectroscopy and LC-MS was used to differentiate the Arabica and Robusta green coffee extracts by principal component analysis (PCA) to determine, which spectroscopic technique allows the best discrimination of coffee varieties. A total of 38 green bean extracts were characterized using NMR-, CD-, and IR spectroscopy along with LC-MS and the data was further analyzed by PCA using different PCA processing parameters by unsupervised non-targeted approach. Distinction between different groups of samples, in particular, Arabica versus Robusta green coffee beans successfully achieved using IR- spectroscopy and LC-MS. Surprisingly, both CD- and NMR spectroscopy fail to achieve in this case, an adequate level of distinction. This is the first study that directly compares the value of various spectroscopic techniques if multivariant statistical techniques are employed to them. ii Acknowledgements I, hereby acknowledge that most of the times, this specific segment of the thesis write-up is supposed to be formal. But, I want to take up the liberty of using the language in which, I am comfortable in to thank people who actually thought they would make a possible ‘scientist’ out of something like ‘me’ risking a doubt which may arise in my examiners mind of being too non-scientific in my thesis. I am taking this risk because, to my personal belief, I think the apology and the gratefulness should come by heart when you are down two beers. Firstly, I would like to thank Mr. Yadav who awaken the interest in me to peruse chemistry as a career as opposed to being a play-writer or a Himalayan monk in my adolescent age. Big thanks with a little judgment goes to the committee, which accepted my application for masters in Nanomolecular science in Jacobs University after having a degree in organic chemistry with moderate grades. I must thank Mr. Sunil Joshi for giving me an opportunity to work in a reputed research institute such as, National Chemical Laboratory (NCL), Pune, which made my application to Jacobs look considerable. I would like to thank Prof. Dr. Nugent who pumped a great deal of professionalism into me starting from how I should reply to the formal emails. Prof. Nugent pulled me out of some tough times and taught me to be serious about the opportunities I have in present and may have in my future. I am grateful to Ms. Shalaka Shah, Mr. Ketan Kulkarni and my lecturer first and a very close friend later, Mr. Suparna Tambe for making my masters days in India and in Germany so easy and joyful. My lab-mates, Rakesh, Tina, Aga, Hande, Marius, Maria, Rohan, Boris, Mohammed, Abhinandan (names not in order of importance!) and their partners have been the family away from my home. All of whom, suffered me, my inappropriate jokes and occasional emotional outbursts with so much of tolerance, that I am unable express my gratitude towards them even if they might not understand the necessity in doing so. I cannot even begin to thank Prof. Dr. Nikolai Kuhnert for trusting me to perform this work as a PhD candidate. My intelligence level matches to a Chimp in front of him; still it’s his skills that he managed to pull a significant contribution out of me to the coffee chemistry. I want to mention that if I manage to incorporate 10% of his knowledge and 1% of his modesty and humbleness in myself when I am of his age, I would consider myself to be very successful in my life. I want to thank Prof. Dr. Clifford for accepting to be an external examiner for my dissertation although; it is of considerable inconvenience for him to travel from U.K. and Prof. Dr. Gerd-Volker Röschenthaler for taking time to revise my thesis. I am thankful to Ms. iii Anja Mueller for her technical support for five years. I appreciate my collaborating professor, Prof. Dr. Materny and his group, in particular Dr. Rasha El-Abasssy for very fruitful collaborative work. I would like to thank Dr. Bassem Bassil from the group of Prof. U. Kortz for the measurement and solution of the single crystal X-ray structures. I have been in Germany for more than five years now and most of the times my wife Neha and me, had to live apart from each other. She has been and will be a definition of unconditional love for me. She stretched me to the extremes of the feeling of happiness and (rarely) suicidal throughout the entire time before and after marriage. She trusted me with the fatherhood of our child, Raghav. Although, she would doubt it, there is no one close to my heart than her. We are a proud evidence for a working long distance happy relationship. There are actually very few words in which I could be expressing my gratefulness towards my father, mother, sister and uncle completely. I am very aware of the fact that it is due to their financial and emotional sacrifices I am what I am today. I am thankful to Jacobs community for teaching me how to accept and respect diverse nationalities and religions. It is the healthy international environment of Jacobs University, which gave me conversational confidence and a feeling of not being special or unique than other communities all over the world. I am thankful to my Indian friends in India and in Jacobs as well, for support and long lasting memories throughout the entire stay in Germany. My former flat mate turned very good friend Naveen, thanks to you too.
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