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(Iso)Flavonoids As Antimicrobial Agents Production, Activity and Mode of Action

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(Iso)Flavonoids As Antimicrobial Agents Production, Activity and Mode of Action Prenylated (iso)flavonoids as an�microbial agents Invitation Prenylated (iso)flavonoids as You are cordially invited to attend the public defence an�microbial agents of my PhD thesis entitled Produc�on, ac�vity and mode of ac�on Prenylated (iso)flavonoids as antimicrobial agents Production, activity & mode of action on Friday 28 May 2021 at 11:00 a.m. in the Aular of Wageningen University, Generaal Foulkesweg 1A, Wageningen Sylvia Kalli-Angel [email protected] Sylvia Kalli-Angel Paranymphs Alexandra Kiskini [email protected] Katharina Duran [email protected] 2021 Sylvia Kalli-Angel Propositions 1. Mono-prenylated isoflavonoids can serve as promising antimicrobials against Gram-positive bacteria and yeasts. (this thesis) 2. The concepts of priming and elicitation cannot be distinguished on the basis of defence metabolite production. (this thesis) 3. The exponentially growing developments in genetic engineering will revolutionize the way we approach the Human Enhancement Question ("what do we want to become?"). based on Yuval Noah Harari, Sapiens: A Brief History of Humankind 4. The olympic motto - Citius, Altius, Fortius (faster, higher, stronger) - is getting increasingly applicable to science. 5. Emotional intelligence should be raised through compulsory activities already in early stages of education. 6. Music disturbs inertia and comforts chaos. Propositions belonging to the thesis, entitled: Prenylated (iso)flavonoids as antimicrobial agents Production, activity and mode of action Sylvia Kalli-Angel Wageningen, 28 May 2021 Prenylated (iso)flavonoids as antimicrobial agents Production, activity and mode of action Sylvia Kalli-Angel Thesis committee Promotor Prof. Dr J.-P. Vincken Professor of Food Chemistry Wageningen University & Research Co-promotor Dr C. Araya-Cloutier Assistant professor, Laboratory of Food Chemistry Wageningen University & Research Other members Prof. Dr T. Abee, Wageningen University & Research Dr V. Fotopoulos, Cyprus University of Technology, Limassol, Cyprus Prof. Dr N. Martin, University of Leiden Prof. Dr H.-G. Janssen, Wageningen University & Research This research was conducted under the auspices of the Graduate School VLAG (Advanced studies in Food Technology, Agrobiotechnology, Nutrition and Health Sciences). Prenylated (iso)flavonoids as antimicrobial agents Production, activity and mode of action Sylvia Kalli-Angel Thesis submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of the Rector Magnificus, Prof. Dr A.P.J. Mol, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Friday 28 May 2021 at 11 a.m. in the Aula. Sylvia Kalli-Angel Prenylated (iso)flavonoids as antimicrobial agents Production, activity and mode of action 214 pages. PhD thesis, Wageningen University, Wageningen, The Netherlands (2021) With references, with summary in English ISBN 978-94-6395-679-6 DOI https://doi.org/10.18174/538785 To my father Στον μπαμπά μου που τον αναζήτησα πολλές φορές αυτά τα τέσσερα χρόνια Abstract Prenylated flavonoids and isoflavonoids (i.e. (iso)flavonoids) are typically produced in the legume (Fabaceae) family as part of plant’s defence mechanism. Prenylation, i.e. the substitution with a C5-isoprenoid moiety, is acknowledged for conferring the antimicrobial properties of prenylated (iso)flavonoids. The first aim of this thesis was to enhance the amounts and diversity of prenylated (iso)flavonoids in planta using the well-studied legume, soybean. Second, the antimicrobial properties of prenylated (iso)flavonoids against the Gram-positive pathogen, methicillin-resistant Staphylococcus aureus (MRSA) and the food spoilage yeast, Zygosaccharomyces parabailii were explored. Lastly, insights into the mode of action of antimicrobial prenylated (iso)flavonoids were sought through in silico and in vitro means. Sensitization of soybean seedlings with reactive oxygen species (ROS), generated through H2O2 and FeSO4, prior to microbial elicitation enhanced the production of prenylated isoflavonoids (glyceollins), compared to the traditional fungal elicitation without priming. Application of the most stable ROS, H2O2, together with AgNO3, prior to microbial elicitation enhanced the production of prenylated isoflavones and a coumestan with promising antibacterial activity, in addition to glyceollins. A systematic study on 106 prenylated (iso)flavonoids tested against MRSA showed that 75% of the di- prenylated (iso)flavonoids and 40% of the mono-prenylated ones were active with minimum inhibitory concentrations (MIC) ≤ 25 μg/mL. Formal and partial charge, hydrophobic volume and uneven distribution of hydrophobic moieties were correlated to antimicrobial activity. The different molecular properties suggested potentially distinct interactions of the different prenylated (iso)flavonoid subclasses with the microbial membrane. Two mono-prenylated isoflavonoids from different subclasses were found to be very active towards the food spoiler and weak organic acid-resistant Z. parabailii (MIC ≤ 12.5 μg/mL, pH 4.0). Killing of Z. parabailii was evidenced within 15 min of exposure to these compounds, accompanied with different deformations of the yeast membrane. Prenylated (iso)flavonoids can be powerful antimicrobials to be used as therapeutics or food preservatives, when their toxicity profile against human cells has been verified. The quantitative models developed provide useful information on the design of new antimicrobial prenylated (iso)flavonoids. Table of contents Chapter 1 General Introduction 1 Chapter 2 Enhanced biosynthesis of the natural 31 antimicrobial glyceollins in soybean seedlings by priming and elicitation Chapter 3 Induction of promising antibacterial prenylated 53 isoflavonoids from different subclasses by sequential elicitation of soybean Chapter 4 Prenylated (iso)flavonoids as agents against 85 methicillin-resistant Staphylococcus aureus - Insights into the molecular properties underlying antibacterial activity Chapter 5 Prenylated (iso)flavonoids as antifungal agents 139 against the food spoiler Zygosaccharomyces parabailii Chapter 6 General Discussion 175 Summary 203 Acknowledgements 207 About the author 211 CHAPTER 1. General Introduction The quest for promising, naturally-derived antimicrobial agents with fundamentally different modes of action from the traditional antimicrobials, is imperative. Molecules with more than one phenolic ring, the so-called polyphenols, are specialized metabolites constitutively present in plants. These polyphenols can be decorated with a C5-isoprenoid (prenyl) moiety as a result of the plant’s strategy to defend itself from invaders. This property may render prenylated phenolic compounds interesting antimicrobial properties. Although effort has been put into exploring the mode of action of these molecules, only small steps have been made. Prenylated phenolics are a diverse group of molecules that can possess different backbones which are decorated with the prenyl group, as well as other functional groups, at different locations and various configurations. However, this large molecular diversity cannot be easily covered in clear-cut structure activity relationships (SARs), which would be the first step in understanding the mode of action of these molecules. In addition, all the different features decorating prenylated phenolics can make a difference in their antimicrobial properties. Hence, investigation and better understanding of overall molecular properties contributing to antimicrobial activity is necessary. Despite the large chemical diversity of prenylated phenolics, their abundance, even in stressed plants, is low which limits their use. Novel, non-laborious ways for efficient production of chemically diverse prenylated phenolics are still under investigation. The need for natural agents that possess antimicrobial activities towards key microorganisms and ways of enhancing their production will be elaborated in this chapter. Chapter 1 1.1. Increased demand for novel, natural and promising antimicrobial agents 1.1.1. Food preservation Microbial food spoilage is related to food borne illnesses, food waste, substantial economic losses and to a negative impact on brand names, posing a major health and economic challenge. The most common spoilage and pathogenic bacteria in foods are Listeria monocytogenes, Escherichia coli O157, Salmonella typhimurium, Staphylococcus aureus, Bacillus cereus, Campylobacter jejuni, Clostridium perfringens [1]. Yeasts become more relevant than bacteria during food preservation. Yeast species such as Zygosaccharomyces bailii, Zygosaccharomyces rouxii, Debaryomyces hansenii, Kluyveromyces lactis and Saccharomyces cerevisiae are often encountered in high sugar and/or acid products such as salad dressings, fruit juices, wine, mayonnaise, chocolate and soft drinks [2]. To prevent the growth of these problematic microorganisms, various preservation techniques are employed in the food industry, together with regular quality, safety and hygienic controls [3-5]. Thermal processing, packaging, irradiation, water activity decrease, and the use of chemical preservatives are some of the means utilized to ensure food safety and stability. Heat treatment and synthetic preservatives are thought to be the most effective means to control the growth of notorious microorganisms [6,7]. Weak organic acids, such as sorbic and benzoic acid are extensively used in large-scale food and soft drink preservation, as they are highly effective
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