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Flavonoids-Macromolecules Interactions in Human Diseases with Focus on Alzheimer, Atherosclerosis and Cancer

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Flavonoids-Macromolecules Interactions in Human Diseases with Focus on Alzheimer, Atherosclerosis and Cancer antioxidants Review Flavonoids-Macromolecules Interactions in Human Diseases with Focus on Alzheimer, Atherosclerosis and Cancer Dana Atrahimovich 1,2, Dorit Avni 3 and Soliman Khatib 1,2,* 1 Lab of Natural Compounds and Analytical Chemistry, MIGAL–Galilee Research Institute, Kiryat Shmona 11016, Israel; [email protected] 2 Department of biotechnology, Tel-Hai College, Upper Galilee 12210, Israel 3 Lab of Sphingolipids, Bioactive Metabolites and Immune Modulation, MIGAL—Galilee Research Institute, Kiryat Shmona 11016, Israel; [email protected] * Correspondence: [email protected]; Tel.: +972-4-6953512; Fax: +972-4-6944980 Abstract: Flavonoids, a class of polyphenols, consumed daily in our diet, are associated with a reduced risk for oxidative stress (OS)-related chronic diseases, such as cardiovascular disease, neurodegenerative diseases, cancer, and inflammation. The involvement of flavonoids with OS- related chronic diseases have been traditionally attributed to their antioxidant activity. However, evidence from recent studies indicate that flavonoids’ beneficial impact may be assigned to their interaction with cellular macromolecules, rather than exerting a direct antioxidant effect. This review provides an overview of the recent evolving research on interactions between the flavonoids and lipoproteins, proteins, chromatin, DNA, and cell-signaling molecules that are involved in the OS-related chronic diseases; it focuses on the mechanisms by which flavonoids attenuate the development of the aforementioned chronic diseases via direct and indirect effects on gene expression and cellular functions. The current review summarizes data from the literature and from our recent research and then compares specific flavonoids’ interactions with their targets, focusing on flavonoid Citation: Atrahimovich, D.; Avni, D.; Khatib, S. Flavonoids-Macromolecules structure–activity relationships. In addition, the various methods of evaluating flavonoid–protein Interactions in Human Diseases with and flavonoid–DNA interactions are presented. Our aim is to shed light on flavonoids action in Focus on Alzheimer, Atherosclerosis the body, beyond their well-established, direct antioxidant activity, and to provide insights into the and Cancer. Antioxidants 2021, 10, mechanisms by which these small molecules, consumed daily, influence cellular functions. 423. https://doi.org/10.3390/ antiox10030423 Keywords: flavonoid; antioxidant; oxidative stress; inflammation; Alzheimer; atherosclerosis; cancer Academic Editor: Janusz Gebicki Received: 28 January 2021 1. Introduction Accepted: 2 March 2021 Flavonoids are a class of polyphenols in plants that are widely consumed in our Published: 10 March 2021 diet. They have a general C6–C3–C6 structural backbone, in which the two C6 units (Ring A and Ring B) are of a phenolic nature. Flavonoids can be divided into different Publisher’s Note: MDPI stays neutral subgroups, such as: flavones, flavonols, flavanones, flavanonols, flavan-3-ols, and with regard to jurisdictional claims in anthocyanins (Figure1). Whereas, in most flavonoids, ring B is attached at the C2 published maps and institutional affil- iations. position of ring C, in some, such as isoflavones and isoflavans, ring B is connected at the C3 position [1]. Dietary flavonoids are natural products that are widely distributed in the plant king- dom. Many foods and beverages, such as fruits, vegetables, legumes, whole grains, choco- late, spices, tea, and wine, are rich sources of flavonoids [1]. Over decades, researchers Copyright: © 2021 by the authors. and food manufacturers have become increasingly interested in flavonoids, due to their Licensee MDPI, Basel, Switzerland. antioxidant properties, their great abundance in our diet, and their suggested role in the This article is an open access article prevention of various diseases that are associated with OS, such as cancer, cardiovascular, distributed under the terms and conditions of the Creative Commons and neurodegenerative diseases [2–5]. Recent literature provides growing evidence of Attribution (CC BY) license (https:// flavonoids’ effects being mediated by mechanisms other than the classical antioxidant creativecommons.org/licenses/by/ activity driven by their chemical property of donating an electron or chelating transition 4.0/). Antioxidants 2021, 10, 423. https://doi.org/10.3390/antiox10030423 https://www.mdpi.com/journal/antioxidants Antioxidants 2021, 10, x FOR PEER REVIEW 2 of 16 and neurodegenerative diseases [2–5]. Recent literature provides growing evidence of fla- Antioxidants 2021, 10, 423 vonoids' effects being mediated by mechanisms other than the classical2 of 15 antioxidant activ- ity driven by their chemical property of donating an electron or chelating transition metals [6,7]. Exploring their fundamental modes of action could provide new insights into the metals [6,7]. Exploring their fundamental modes of action could provide new insights into themechanisms mechanisms byby which which flavonoids flavonoids influence influence biological biological functions. functions. FigureFigure 1. Structures1. Structures of the of main the flavonoid main flavonoid subclasses. subclasses. 2. Biological Activities of Flavonoids 2.1.2. Biological Flavonoids as AntioxidantsActivities of Flavonoids With respect to their antioxidant activity, flavonoids are believed to prevent diseases2.1. Flavonoids that are relatedas Antioxidants to OS via the direct scavenging of reactive oxygen species (ROS) throughWith respect the donation to their of antioxidant a hydrogen atom, activity, activation flavonoids of antioxidant are believed enzymes, to prevent diseases metal (such as iron and copper)-chelating activity, and alleviation of oxidative stress thatthat is are caused related by nitric to OS oxide via (NO) the [ 1direct,8–11]. scavengi Antioxidantng activity, of reactive though, oxygen cannot species be the (ROS) through solethe explanation donation forof a the hydrogenin vivo cellular atom, effects activation of flavonoids’, of antioxidant since antioxidant enzymes, activity metal (such as iron isand expressed copper)-chelating at flavonoid concentrations activity, and that alleviation are above 10 ofµ M,oxidative but their stress concentration that is caused by nitric µ inoxide the circulation (NO) [1,8–11]. does not Antioxidant exceed 2 M[ activity,12]. Dietary though, flavonoids cannot are poorlybe the absorbed sole explanation for the from the intestine, highly metabolized, or rapidly eliminated. During the course of absorption,in vivo cellular flavonoids effects are of conjugated flavonoids’, in the since small antioxidant intestine and activity later in is the expressed liver. at flavonoid Thisconcentrations process mainly that includes are above methylation, 10M, sulfation, but their and concentration glucuronidation. in Thisthe circulation is a does not metabolicexceed 2 detoxificationM [12]. Dietary process thatflavonoids is common are to poorly many xenobiotics absorbed that from restricts the theirintestine, highly me- potentialtabolized, toxic or effects rapidly and facilitateseliminated. their During biliary and the urinary course elimination of absorption, by increasing flavonoids are conju- their hydrophilicity [13]. gatedRecent in the studies small have intestine suggested and that thelater biological in the effectsliver. ofThis flavonoids process may mainly be medi- includes methyla- atedtion, by sulfation, different mechanisms and glucuronidation. that have not yet This been is fullya metabolic explored. detoxification The present review process that is com- focusesmon to on many flavonoids’ xenobiotics mode of action that throughrestricts their their interaction potential with toxic macromolecules, effects and such facilitates their bil- asiary lipoproteins, and urinary cell and elimination serum proteins, by increasing and DNA and their RNA hydrophilicity (Figure2). [13]. Recent studies have suggested that the biological effects of flavonoids may be medi- ated by different mechanisms that have not yet been fully explored. The present review focuses on flavonoids’ mode of action through their interaction with macromolecules, such as lipoproteins, cell and serum proteins, and DNA and RNA (Figure 2). Antioxidants 2021, 10, x FORAntioxidants PEER REVIEW2021, 10, 423 3 of 16 3 of 15 Figure 2. FigureFlavonoids’ 2. Flavonoids’ mode mode of action of action through through th theireir interaction with with macromolecules. macromolecules. 2.2. Flavonoid Interactions with Macromolecules 2.2. Flavonoid Interactio2.2.1. Flavonoid–Proteinns with Macromolecules Interactions 2.2.1. Flavonoid–ProteinMolecular Interactions interactions of proteins and nucleic acids with low-molecular-weight com- Molecular interactionspounds are of an proteins area of fundamental and nucleic interest acids with [14]. low-molecular-weight At low concentrations, molecules, com- such pounds are an areaas ions,of fundamental metabolites, andinterest osmolytes, [14]. At may low affect concentrations, proteins, such molecules, as enzymes, such receptors, an- as ions, metabolites,tibodies, and osmolytes, and transcription may affect factors proteins, [15]. The such effect as may enzymes, be at the receptors, structural, an- functional, or conformational levels [7]. Dietary flavonoids are a good example of small molecules tibodies, and transcription factors [15]. The effect may be at the structural, functional, or that mediate cellular effects, which are central to intracellular signaling cascades [16]. conformational levelsThe effects
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