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Polyphenolic Compounds As Electron Shuttles for Sustainable Energy Utilization Chung‑Chuan Hsueh1, Chia‑Chyi Wu2 and Bor‑Yann Chen1*

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Polyphenolic Compounds As Electron Shuttles for Sustainable Energy Utilization Chung‑Chuan Hsueh1, Chia‑Chyi Wu2 and Bor‑Yann Chen1* Hsueh et al. Biotechnol Biofuels (2019) 12:271 https://doi.org/10.1186/s13068-019-1602-9 Biotechnology for Biofuels REVIEW Open Access Polyphenolic compounds as electron shuttles for sustainable energy utilization Chung‑Chuan Hsueh1, Chia‑Chyi Wu2 and Bor‑Yann Chen1* Abstract For renewable and sustainable bioenergy utilization with cost‑efectiveness, electron‑shuttles (ESs) (or redox media‑ tors (RMs)) act as electrochemical “catalysts” to enhance rates of redox reactions, catalytically accelerating electron transport efciency for abiotic and biotic electrochemical reactions. ESs are popularly used in cellular respiratory systems, metabolisms in organisms, and widely applied to support global lives. Apparently, they are applicable to increase power‑generating capabilities for energy utilization and/or fuel storage (i.e., dye‑sensitized solar cell, bat‑ teries, and microbial fuel cells (MFCs)). This frst‑attempt review specifcally deciphers the chemical structure associa‑ tion with characteristics of ESs, and discloses redox‑mediating potentials of polyphenolics‑abundant ESs via MFC modules. Moreover, to efectively convert electron‑shuttling capabilities from non‑sustainable antioxidant activities, environmental conditions to induce electrochemical mediation apparently play critical roles of great signifcance for bioenergy stimulation. For example, pH levels would signifcantly afect electrochemical potentials to be exhibited (e.g., alkaline pHs are electrochemically favorable for expression of such electron‑shuttling characteristics). Regarding chemical structure efect, chemicals with ortho‑ and para‑dihydroxyl substituents‑bearing aromatics own convertible characteristics of non‑renewable antioxidants and electrochemically catalytic ESs; however, ES capabilities of meta‑ dihydroxyl substituents can be evidently repressed due to lack of resonance efect in the structure for intermediate radical(s) during redox reaction. Moreover, this review provides conclusive remarks to elucidate the promising feasibil‑ ity to identify whether such characteristics are non‑renewable antioxidants or reversible ESs from natural polyphenols via cyclic voltammetry and MFC evaluation. Evidently, considering sustainable development, such electrochemically convertible polyphenolic species in plant extracts can be reversibly expressed for bioenergy‑stimulating capabilities in MFCs under electrochemically favorable conditions. Keywords: Electron shuttles, Polyphenolics, Microbial fuel cells, Antioxidants Background One example of this technology is the exploitation of In this review, we aim to clarify some of the mysteries the bioelectrochemical potential of electroactive micro- of the electron shuttles (ESs) used in sustainable bioen- organisms. Bioelectrochemical devices, such as micro- ergy applications (e.g., electro-fermentation and elec- bial fuel cells (MFCs), can use synergistic/cooperative trochemical biorefning). In particular, increasing consortia of microbes as biocatalysts, and the electric energy, and resource scarcity and ecological destruc- current produced by the oxidation of organic com- tion have encouraged for bioremediation techniques pounds can be used for simultaneous bioelectricity and the use of renewable material and energy sources. generation and wastewater treatment [1–5]. In fact, Tus, the creation of innovative, practical “green” sus- MFCs are a promising platform to explore the electro- tainable bioenergy applications is inevitably required. chemical potential of bioresources for bioenergy and biorefnery uses. In an MFC, an anodic bioflm of bac- teria is used to oxidize organic matter, which acts as *Correspondence: [email protected]; [email protected] 1 Department of Chemical and Materials Engineering, National I‑Lan nutrient source (i.e., the primary substrate), thus University, I‑Lan 26047, Taiwan degrading pollutants or detoxifying inorganic contami- Full list of author information is available at the end of the article nants co-metabolically. Te protons generated in this © The Author(s) 2019. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creat iveco mmons .org/licen ses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/ publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. Hsueh et al. Biotechnol Biofuels (2019) 12:271 Page 2 of 26 process migrate through a proton exchange membrane a 1.0 toward the cathode in a double-chamber MFC, and the Vitamin B2 10 electrons overcome the interfacial mass transfer resist- 0.5 Vitamin B2 50 ance on the anodic bioflm and pass through an exter- Vitamin B2 100 nal circuit to the cathode (e.g., air cathode), 0.0 simultaneously generating bioelectricity. Terefore, A bioelectricity generation occurs at the (bio)cathode µ -0.5 I/ along with water formation (i.e., + − ½O2 + 2H + 2e → H2O). Tere are several mecha- -1.0 nisms for bioflm formation, direct electron transfer, mediator electron transport, and direct interspecies -1.5 electron transfer that afect the operating efciencies of -2.0 MFCs [6]. To decrease the internal electron transfer -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.00.2 0.40.6 resistance between electron acceptors and donors sig- E/V nifcantly, exogenous bioelectrochemical catalysts are b 6 commonly used; this allows the power-generating per- Vitamin C 10 5 Vitamin C 50 formance of MFCs to be increased. Moreover, electron Vitamin C 100 transfer between microbes and from microbes to elec- 4 tron-accepting compounds can be facilitated using ESs. 3 Tis is a promising way to decline the activation energy A µ and increase efcient electron between the intracellular I/ 2 compartment and extracellular medium during micro- bial energy metabolism [7, 8]. Tat is, ESs are “electro- 1 chemical catalysts” that increase the reaction rate under appropriate environmental conditions. Because 0 electrochemical catalysts (e.g., ESs) are not consumed -1 during the catalytic reaction, they function reversibly, -0.6 -0.4 -0.2 0.00.2 0.40.6 0.81.0 1.2 stably, and persistently. In particular, oxygen is a strong E/V electron acceptor; anaerobic conditions are necessary Fig. 1 a Cyclic voltammetry of Vitamin B2 for 100 scan cycles, to guarantee the efective redox-mediating behavior of clearly indicating the persistence of two stable redox potential peaks of electron shuttle [10]. b Cyclic voltammogram of vitamin C ESs during electrochemical reactions. In the presence (1000 mg/L) in PBS solution at scan rate 10 mV/s, indicating only one of ESs and the absence of strong electron acceptors redox potential peak of antioxidant [10] (e.g., O2), electrochemically driven reactions and reduc- tive biodegradation occur faster because such electro- chemical catalyst provides an alternative reaction process [9]. Te observed redox potential peaks of vita- pathway with lower activation energy than that of the min B2 (ribofavin), a well-known ES, can be main- non-catalyzed mechanism. Tat is, ESs can speed up tained over 100 CV cycles (Fig. 1a) [10]. In contrast, redox reactions by providing “a set of elementary steps” 100 CV cycles of the well-characterized antioxidant with more (bio)electrochemically favorable kinetics vitamin C only yielded an oxidation peak, as shown in than those that exist in their absence. Tus, supple- Fig. 1b [10]. Furthermore, if the ratio of the peak cur- menting an ES to a MFC or bioreactor system that is rents of a test chemical approaches unity (i.e., ipc/ipa ≈ 1 not in steady state or equilibrium will speed up both or the reduction and oxidation potentials are symmet- the forward and reverse rates, allowing an equilibrium ric, where ipc and ipa are the cathodic and anodic peak mixture to be achieved much faster than anticipated. currents for a reversible reaction, respectively), the Tus, ESs play a crucial role in increasing the electron chemical could be an ES with semi-reversible redox transfer efciency between electron donors and accep- characteristics and electrochemical use (e.g., biorefn- tors for sustainable bioenergy extraction. Te electro- ery and bioenergy uses) [11–13]. chemical characteristics of ESs can be determined from ESs can be either inorganic or organic compounds, cyclic voltammetry (CV) profles, and the diference such as iodide/triiodide [14] and Fe3+ [15], quinones (ΔE) between the cathodic (reduction) potential (E ) pc [7], and vitamin B2 [16, 17]. Considering the need for and anodic (oxidation) potential (Epa) is given by the environmental friendliness for sustainable develop- Butler–Volmer equation and Cottrell equations: ment, organic compounds, both natural and syn- nFAC0√D 56.5 mV i Epa Epc = √πt and − = n , for an “n” electron thetic, with low biotoxicities (e.g., polyphenols or Hsueh et al. Biotechnol Biofuels (2019) 12:271 Page 3 of 26 polyhydroxyphenols) are favorable and promising for Table 1 Some compounds used as electron shuttles (ESs) use as ESs compared to other inorganic species. In the in microbial fuel cells (MFCs) or biological anaerobic decolorization (BD) following sections, we clarify several aspects of ESs not previously reported and suggest an optimal strategy Redox mediatorsa (ESs) Applied conditionb References for maximizing bioenergy extraction
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