Sacrificial H2 production over Pt/TiO2 using alcohols (1) and carboxylic acids (2).
\r\n\t
",isbn:"978-1-83962-547-3",printIsbn:"978-1-83962-546-6",pdfIsbn:"978-1-83962-548-0",doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!0,hash:"e5ba02fedd7c87f0ab66414f3b07de0c",bookSignature:" John P. Tiefenbacher",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/10765.jpg",keywords:"Managing Urbanization, Managing Development, Managing Resource Use, Drought Management, Flood Management, Water Quality Monitoring, Air Quality Monitoring, Ecological Monitoring, Modeling Extreme Natural Events, Ecological Restoration, Restoring Environmental Flows, Environmental Management Perspectives",numberOfDownloads:null,numberOfWosCitations:0,numberOfCrossrefCitations:null,numberOfDimensionsCitations:null,numberOfTotalCitations:null,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"January 12th 2021",dateEndSecondStepPublish:"February 9th 2021",dateEndThirdStepPublish:"April 10th 2021",dateEndFourthStepPublish:"June 29th 2021",dateEndFifthStepPublish:"August 28th 2021",remainingDaysToSecondStep:"20 days",secondStepPassed:!1,currentStepOfPublishingProcess:2,editedByType:null,kuFlag:!1,biosketch:"A geospatial scholar working at the interface of natural and human systems, collaborating internationally on innovative studies about hazards and environmental challenges. Dr. Tiefenbacher has published more than 200 papers on a diverse array of topics that examine perception and behaviors with regards to the application of pesticides, releases of toxic chemicals, environments of the U.S.-Mexico borderlands, wildlife hazards, and the geography of wine.",coeditorOneBiosketch:null,coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"73876",title:"Dr.",name:"John P.",middleName:null,surname:"Tiefenbacher",slug:"john-p.-tiefenbacher",fullName:"John P. Tiefenbacher",profilePictureURL:"https://mts.intechopen.com/storage/users/73876/images/system/73876.jfif",biography:"Dr. John P. Tiefenbacher (Ph.D., Rutgers, 1992) is a professor of Geography at Texas State University. His research has focused on various aspects of hazards and environmental management. Dr. Tiefenbacher has published on a diverse array of topics that examine perception and behaviors with regards to the application of pesticides, releases of toxic chemicals, environments of the U.S.-Mexico borderlands, wildlife hazards, and the geography of wine. More recently his work pertains to spatial adaptation to climate change, spatial responses in wine growing regions to climate change, the geographies of viticulture and wine, artificial intelligence and machine learning to predict patterns of natural processes and hazards, historical ethnic enclaves in American cities and regions, and environmental adaptations of 19th century European immigrants to North America's landscapes.",institutionString:"Texas State University",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"1",totalChapterViews:"0",totalEditedBooks:"6",institution:{name:"Texas State University",institutionURL:null,country:{name:"United States of America"}}}],coeditorOne:null,coeditorTwo:null,coeditorThree:null,coeditorFour:null,coeditorFive:null,topics:[{id:"12",title:"Environmental Sciences",slug:"environmental-sciences"}],chapters:null,productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"},personalPublishingAssistant:{id:"194667",firstName:"Marijana",lastName:"Francetic",middleName:null,title:"Ms.",imageUrl:"https://mts.intechopen.com/storage/users/194667/images/4752_n.jpg",email:"marijana@intechopen.com",biography:"As an Author Service Manager my responsibilities include monitoring and facilitating all publishing activities for authors and editors. From chapter submission and review, to approval and revision, copyediting and design, until final publication, I work closely with authors and editors to ensure a simple and easy publishing process. I maintain constant and effective communication with authors, editors and reviewers, which allows for a level of personal support that enables contributors to fully commit and concentrate on the chapters they are writing, editing, or reviewing. I assist authors in the preparation of their full chapter submissions and track important deadlines and ensure they are met. I help to coordinate internal processes such as linguistic review, and monitor the technical aspects of the process. As an ASM I am also involved in the acquisition of editors. 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Venkateswarlu",coverURL:"https://cdn.intechopen.com/books/images_new/371.jpg",editedByType:"Edited by",editors:[{id:"58592",title:"Dr.",name:"Arun",surname:"Shanker",slug:"arun-shanker",fullName:"Arun Shanker"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"878",title:"Phytochemicals",subtitle:"A Global Perspective of Their Role in Nutrition and Health",isOpenForSubmission:!1,hash:"ec77671f63975ef2d16192897deb6835",slug:"phytochemicals-a-global-perspective-of-their-role-in-nutrition-and-health",bookSignature:"Venketeshwer Rao",coverURL:"https://cdn.intechopen.com/books/images_new/878.jpg",editedByType:"Edited by",editors:[{id:"82663",title:"Dr.",name:"Venketeshwer",surname:"Rao",slug:"venketeshwer-rao",fullName:"Venketeshwer Rao"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"4816",title:"Face Recognition",subtitle:null,isOpenForSubmission:!1,hash:"146063b5359146b7718ea86bad47c8eb",slug:"face_recognition",bookSignature:"Kresimir Delac and Mislav Grgic",coverURL:"https://cdn.intechopen.com/books/images_new/4816.jpg",editedByType:"Edited by",editors:[{id:"528",title:"Dr.",name:"Kresimir",surname:"Delac",slug:"kresimir-delac",fullName:"Kresimir Delac"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"3621",title:"Silver Nanoparticles",subtitle:null,isOpenForSubmission:!1,hash:null,slug:"silver-nanoparticles",bookSignature:"David Pozo Perez",coverURL:"https://cdn.intechopen.com/books/images_new/3621.jpg",editedByType:"Edited by",editors:[{id:"6667",title:"Dr.",name:"David",surname:"Pozo",slug:"david-pozo",fullName:"David Pozo"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}}]},chapter:{item:{type:"chapter",id:"66682",title:"Glycerol as a Superior Electron Source in Sacrificial H2 Production over TiO2 Photocatalyst",doi:"10.5772/intechopen.85810",slug:"glycerol-as-a-superior-electron-source-in-sacrificial-h-sub-2-sub-production-over-tio-sub-2-sub-phot",body:'\nThe major issue in the current world is an urgent need to stop the increase of CO2 levels. A large amount of consumption of fossil resources causes serious environmental problems such as global warming and air pollution. Therefore, biofuels such as bioethanol, bio-hydrogen, and biodiesel (BDF) have gained much attention as renewable and sustainable energy alternative to petroleum-based fuels [1]. However, the problems to be solved for practical uses still remain in each biofuel. In bioethanol, the ethanol concentrations are still too low to isolate pure ethanol by distillation at a low energy cost [2, 3]. Bio-hydrogen is isolated spontaneously from reaction mixtures without operations to separate. However, it is needed to construct newly a supply system to vehicles.
\nBDF is produced by transesterification of vegetable oil or animal fats with methanol along with the co-production of glycerol [Eq. (1)] [4]. Although methyl alkanoate (BDF) is easily isolated by phase separation, a mixture of glycerol and unreacted methanol remains in aqueous solution as waste. New utilization of these wastes is required. Reforming of glycerol has been extensively investigated through pyrolysis [5, 6], steam gasification [7, 8], and biological reforming [9, 10]. We have focused on photocatalytic reforming over titanium dioxide (TiO2) [11]:
\nTiO2 has a semiconductor structure with 3.2 eV of bandgap, which corresponds to 385 nm of light wavelength [12]. Therefore, the TiO2 can be excited by 366 nm emitted from a high-pressure mercury lamp. Irradiation of the TiO2 induces charge separation into electrons and holes (Figure 1). Electron excited to the conduction band serves to reduce water to H2. Evolution of H2 is usually accelerated by deposition of noble metals (Pt, Pd, and Au) onto the TiO2. The positive charge (hole) oxidizes hydroxide absorbed on the surface of TiO2 to generate hydroxyl radicals, which is eventually transformed to O2 [13]. However, spontaneous conversion of hydroxyl radical into O2 is inefficient. Moreover, water splitting into O2 and H2 is a large uphill reaction, resulting in rapid reverse reaction.
\nPhotocatalytic water splitting over TiO2.
On the other hand, the hydroxyl radicals can be effectively consumed by the use of electron-donating sacrificial agents (hole scavengers), thus accelerating the H2 production (Figure 1) [14]. This method is named “sacrificial H2 production.” The sacrificial H2 production is an uphill process, but the energy change is small. Therefore, the sacrificial H2 production proceeds more smoothly compared with water splitting without sacrificial agents, thus providing a convenient method to generate H2 [15]. When one equivalent of hydroxyl radical is consumed, one equivalent of electron is generated to produce 0.5H2.
\nDuring our investigations on sacrificial H2 production over a Pt-loaded TiO2 (Pt/TiO2) [15], it was found that sacrificial agents with all of the carbon attached oxygen atoms such as saccharides, polyalcohols (e.g., arabitol, glycerol, 1,2-ethandiol), and methanol continued to serve as an electron source until their sacrificial ability was exhausted. Glycerol (1a) and methanol (1b) are by-products from BDF synthesis. The 1a has the potential to produce hydrogen in theoretical yield of seven equivalents, whose combustion energy (ΔH = 1995 kJ mol−1) is larger than ΔH of 1a (1654.3 kJ mol−1) [Eq. (2)]. Also, 1b can produce three equivalents of hydrogen, whose ΔH (855 kJ mol−1) is larger than ΔH of 1b (725.7 kJ mol−1) [Eq. (3)] [16]. Thus, photo-energy can promote uphill process:
\nGenerally, biomass reforming is started by the production of water-soluble materials from biomass through biological treatment as well as chemical reaction [17, 18]. The resulting water-soluble materials (saccharides, amino acids) are converted to biofuels such as ethanol, methane, and hydrogen through various catalytic reactions in aqueous solution. Our biomass reforming is performed in aqueous solution through sacrificial H2 production over Pt/TiO2 using water-soluble materials derived from lignocelluloses [19, 20, 21] and chlorella [22] (Figure 2).
\nOutline of conversion of glycerol to hydrogen.
In this chapter, we will show H2 production through sacrificial H2 production over Pt/TiO2 using 1a and 1b from standpoints of construction of renewable energy system and clean synthesis of BDF.
\nNMR spectra were taken on a Bruker AV 400M spectrometer for CDCl3 solution. LC-MS analysis were performed on a Waters Alliance 2695 under conditions (ESI ionization, capillary voltage 3.5 kV, source temperature 120°C and desolvation temperature 350°C) using column (Waters, SunFire C18, 2.1 mmΦ × 150 mm) and 1% formic acid in MeOH-H2O (6:4) as an eluent solution. GLC analysis of solution was performed on a Shimadzu 14A gas liquid chromatograph with FID detector at a temperature raised from 50 to 250°C using a capillary column (J & W CP-Sil 5CB, 0.32 mmΦ × 50 m).
\nReaction vessel was a cylindrical flask with 30 cm of height and 7.5 cm of diameter, which had three necks on the top. A high-pressure mercury lamp (100 W, UVL-100HA, Riko, Japan), which emitted mainly a light at 313 and 366 nm, was inserted into the large central neck of the reaction vessel. The reaction vessel was connected to a measuring cylinder with a gas-impermeable rubber tube to collect the evolved gas. The reaction vessel was set in a water bath to keep it at 20°C. The stirring of the solution was performed by magnetic stirrer.
\nAlmost all research has used TiO2 in anatase form such as P25 (Degussa Co. Ltd., Germany) and ST01 (Ishihara Sangyo Co. Ltd., Japan) for photocatalytic H2 production. A Pt-loaded TiO2 catalyst (Pt/TiO2) was prepared by photo-deposition method according to the previous literature [23]. An aqueous solution (400 mL) containing TiO2 (4.0 g, ST01), K2PtCl6 (40–400 mg), and 2-propanol (3.06 mL) was introduced reaction vessel, which was large scale of cylindrical flask with 35 cm of height and 9.0 cm of diameter. After the oxygen was purged by N2 gas bubbling for 20 min, the solution was irradiated by stirring. After irradiation for 24 h, the water was entirely removed from the reaction mixture by an evaporator. The resulting black precipitate was washed with water on a filter and then dried under reduced pressure to produce Pt/TiO2 [14]. The Pt content on TiO2 was optimized to be 2.0 wt% by the comparison of the H2 amounts evolved from photocatalytic reaction using 1a (115 mg, 1.25 mmol) over various Pt contents of the Pt-doped TiO2 (100 mg, 1.25 mmol) [15]. The structure of Pt/TiO2 was analyzed by a Shimadzu XRD 7000 diffractometer.
\nPt/TiO2 (100 mg) and the given amounts of aqueous solution of sacrificial agent were introduced to reaction vessel. The volume of the reaction solution was adjusted to 150 mL with water. Oxygen was purged from reaction vessel by N2 gas for 20 min. TiO2 was suspended in aqueous solution by vigorous stirring during the irradiation. Total volume of the evolved gas was measured by a measuring cylinder. Irradiation was performed until the gas evolution ceased. The evolved gas (0.5 mL) was taken through rubber tube using syringe and was subjected to the quantitative analysis of H2, N2, CH4, and CO2. Gas analysis was performed on a Shimadzu GC-8A equipped with TCD detector at temperature raised from 40 to 180°C using a stainless column (3 mmΦ, 6 m) packed with a SHINCARBON ST (Shimadzu).
\nIn order to determine the quantum yield (Φ) for H2 evolution, the H2 amount per hour was measured for various concentrations of 1 (8–40 mM). The H2 amount per hour was converted to Φ using an actinometer which was H2 amount per hour evolved from the sacrificial H2 production using ethanol (0.434 M) at pH 10.0 over Pt/TiO2 (Pt content 1.0 wt%), whose Φ was reported to be 0.057 [24]. Limiting quantum yields (Φ∞) at an infinite concentration of 1 was determined from the intercept of the double reciprocal plots of Φ vs. the concentration of 1 [25].
\nSacrificial H2 production was applied to 1a and 1b. The Pt/TiO2 (100 mg, 1.25 mmol, 2.0 wt% of Pt) was suspended in an aqueous solution (150 ml) of 1a and 1b, whose concentration was varied in a range of 0.25–1.25 mmol. After O2 was purged from the reaction vessel using N2 gas, UV irradiation was continued under vigorous stirring for 10–17 h until gas evolution had ceased [15]. The evolved gas volumes were plotted against the amounts of sacrificial agent used. In the absence of sacrificial agents, the evolved H2 from water was small (<2 mL). Figure 3A is a typical example of the plots of volume of H2 and CO2 against the amounts of 1a used. Gas volume increased as an increase of the amounts of 1a used. However, the molar ratio of the evolved H2 to 1a (H2/1a) was dependent on the amount of 1a used. Therefore, the H2/1a values were plotted against the molar ratios of 1a to catalyst (1a/catalyst). This plot gave a good linear relationship, as shown in Figure 3B.
\n(A) The gas volume evolved from the sacrificial H2 production using glycerol (1a) over Pt/TiO2. (B) Plots of H2/1a and CO2/1a against 1a/catalyst: H2 (●) and CO2 (▲).
The intercept of the plot equaled the limiting amount of H2 (H2max) obtained from 1 mol of 1a when the amount of the catalyst was extrapolated to infinite. The H2max became 7.2. The limiting amount of CO2 (CO2max) obtained from 1 mol of 1a at an infinite amount of the catalyst was also determined to be 3.1 from the plots of CO2/1a against 1a/catalyst (Figure 3B). The H2max and CO2max are summarized in Table 1. If the sacrificial agent (CnHmOp) is entirely decomposed into CO2 and H2O by hydroxyl radicals, theoretically (2n + 0.5m − p) equivalents (P) of H2 will be evolved in the TiO2 photocatalytic reaction [Eq. (4)]. The P values are listed in Table 1. Therefore, the chemical yield of H2 production was defined to be 100 H2max/P. In the case of 1a, the yield of H2 production was found to be 103%. Also, the CO2max value was close to the theoretical value. Similarly, the H2max and CO2max values of 1b were determined to be 3.0 and 1.0, respectively. This shows that 1a and 1b are superior sacrificial agents, which are completely decomposed into CO2 and water by sacrificial H2 production:
\nSacrificial agents | \nFormula | \nPa | \nProducts/mol mol−1 | \nYield/% b | \nΦ∞c | \n||
---|---|---|---|---|---|---|---|
H2max | \nCO2max | \nCH4max | \n|||||
Alcohols | \n|||||||
Glycerol (1a) | \nC3H8O3 | \n7 | \n7.2 | \n3.1 | \n\n | 103 | \n0.078 | \n
Methanol (1b) | \nCH4O | \n3 | \n3.0 | \n1.0 | \n\n | 100 | \n0.057 | \n
1-Hydroxy-2-propanone (1c) | \nC3H6O2 | \n7 | \n4.9 | \n2.5 | \n0.30 | \n87 | \n0.045 | \n
1,2-Propanediol (1d) | \nC3H8O2 | \n8 | \n4.8 | \n1.0 | \nTrace | \n60 | \n\n |
1,3-Propanediol (1e) | \nC3H8O2 | \n8 | \n4.2 | \n0.5 | \n\n | 53 | \n\n |
1-Propanol (1f) | \nC3H8O | \n9 | \n4.1 | \n1.0 | \n\n | 46 | \n0.069 | \n
2-Propanol (1g) | \nC3H8O | \n9 | \n1.3 | \n0.0 | \n\n | 14 | \n\n |
Carboxylic acids | \n|||||||
Glycolic acid (2a) | \nC2H4O3 | \n3 | \n2.8 | \n1.8 | \n\n | 93 | \n\n |
Oxalic acid (2b) | \nC2H2O4 | \n1 | \n1.0 | \n2.0 | \n\n | 100 | \n\n |
Formic acid (2c) | \nCH2O2 | \n1 | \n1.0 | \n1.0 | \n\n | 100 | \n\n |
Acetic acid (2d) | \nC2H4O2 | \n4 | \n2.9 | \n1.7 | \n0.27 | \n100 | \n\n |
Pyruvic acid (2e) | \nC3H4O3 | \n5 | \n3.9 | \n2.7 | \n0.30 | \n102 | \n\n |
Lactic acid (2f) | \nC3H6O3 | \n6 | \n4.1 | \n2.3 | \n0.30 | \n88 | \n\n |
Malonic acid (2g) | \nC3H4O4 | \n4 | \n2.6 | \n2.7 | \n0.31 | \n96 | \n\n |
Propanoic acid (2h) | \nC3H6O2 | \n7 | \n2.3 | \n1.0 | \n\n | 33 | \n\n |
Sacrificial H2 production over Pt/TiO2 using alcohols (1) and carboxylic acids (2).
Theoretical amount of hydrogen was calculated using Eq. (4).
Total chemical yield of H2 and CH4 = 100 (H2max + 4CH4max)/P.
Limiting quantum yield (Φ∞) for H2 evolution with infinite amounts of 1.
Generally, hydroxyl radical can abstract hydrogen atom more efficiently from the hydroxylated carbon rather than the non-hydroxylated carbon. Therefore, degradation of alcoholic sacrificial agents proceeds through hydrogen-atom abstraction by hydroxyl radical from the hydroxylated alkyl group [Eq. (5)] [15]. Hydroxyl radical reacts with the secondary alcohols to produce ketones, which does not undergo further degradation. The primary alcohols reacted with hydroxyl radical to produce aldehyde, which undergoes further oxidation to carboxylic acid [Eq. (6)]. Furthermore, H abstraction from carboxylic acid by hydroxyl radical induces decarboxylation from carboxylic acids through the formation of carboxyl radical (RCO2·) [Eq. (7)]. When hydroxyl group was substituted on α-position of carboxylic acid [X = OH in Eq. (7)], the decarboxylation took place more smoothly. Many researchers proposed that the decomposition of carboxylic acids is initiated by hole transfer to the carboxylic group rather than H abstraction by hydroxyl radicals [26, 27, 28, 29]. Thus, the degradation of alcohols proceeds through the formation of carboxylic acids:
\nIn 2009, Kondarides et al. reported sacrificial H2 production from 1a over Pt/TiO2 (0.1–0.5 wt% Pt) [30]. They proposed that the decomposition of 1a proceeded through the formation of methanol and acetic acid which were eventually decomposed into CO2 and H2 in a ratio of 3:7 [31]. Also, in irradiation of Pt/TiO2 in the absence and in the presence of glycerol, they detected H2O2 which was produced by dimerization of hydroxyl radicals [32]. Also, Ratnawati et al. detected a small amount of 1,2-ethanediol and acetic acid in reaction mixture [33]. They elucidated that Pt catalyzed not only reduction of water to H2 but also dehydration of 1a. Bowker et al. examined the photocatalytic reforming of 1a over M/TiO2 (M = 0.5 wt% Pd, 2.0 wt% Au) [34]. However, chemical yield of H2 was still unclear.
\nWe thought that degradation of 1a was initiated by the oxidation of terminal alcohol by hydroxyl radical. It was thought that glycolic acid (2a) and oxalic acid (2b) were the intermediates intervening in degradation process of 1a. Therefore, we performed sacrificial H2 production over Pt/TiO2 using 2a and 2b. The H2max and CO2max values of 2a and 2b were shown in Table 1. The 2a and 2b were completely decomposed to CO2 and water, since the CO2max values of 2a and 2b were determined to be 1.8 and 2.0, respectively. Although the degradation of 2a could proceed through 2b and/or formic acid (2c), we could not determine which degradation pathway occurred. In the case of 1b, it was thought that 2c was undoubtedly the intermediates intervening in degradation process of 1b. The 2c was completely decomposed to CO2 and water, since the CO2max value of 2c was 1.0. However, 2a, 2b, and 2c were not detected in the reaction mixture of sacrificial H2 production using 1a and 1b due to easy decomposition of these carboxylic acids by hydroxyl radical. Also, Lu et al. have reported the degradation of 2b and 2c, which can adsorb on Pt/TiO2 to give one equivalent H2 under irradiation [35, 36].
\nAccording to Eqs. (5)–(7), a possible degradation mechanism of 1a and 1b by hydroxyl radical is shown in Figure 4. In the case of 1a, 14 equivalents of hydroxyl radicals were consumed by 1a along with the formation of 3CO2. At the same time, seven equivalents of H2 were evolved. Actually, 7.2 of H2max and 3.1 of CO2max values of 1a were provided from sacrificial H2 production using 1a. In the case of 1b, six equivalents of hydroxyl radicals were consumed along with the formation of one equivalent of CO2 and 3H2, providing actually 3.0 of H2max and 1.0 of CO2max.
\nDegradation pathways of glycerol (1a) and methanol (1b) by hydroxyl radical in the sacrificial H2 production over Pt/TiO2.
In order to elucidate the relationship between molecular structure of sacrificial agents and degradation yield, sacrificial H2 production was performed using propane-based alcohols such as 1-hydroxy-2-propanone (1c); 1,2-propanediol (1d); 1,3-propanediol (1e); 1-popanol (1f); and 2-propanol (1g) (Figure 5) as well as the related carboxylic acids (2d–2h) [15].
\nPropane-based alcohols (1c–1g) as sacrificial agents for the photocatalytic H2 production.
Sacrificial H2 evolution using 1c produced CH4 along with the formation of H2 and CO2. Limiting amount of CH4 (CH4max) obtained from 1 mol of 1c was 0.30 along with 4.9 of H2max and 2.5 of CO2max values. In the case of sacrificial H2 production along with the formation of CH4, the chemical yield was defined by the following equation: Yield = 100 (H2max + 4CH4max)/P. The yield for the sacrificial H2 production using 1c was calculated to be 87%. Moreover, acetic acid (2d) was detected by LC-MS of the reaction solution at low conversion. A peak appeared at 2.24 min of retention time which showed mass peaks at m/z 60 (M+) and 43 (CH3CO+). Therefore, 2d was subjected to sacrificial H2 production. Mozia et al. reported that 2d was decomposed into H2, CO2, and CH4 over TiO2 without Pt [37], although Zheng et al. reported that a trace amount of CH4 was detected from 2d over Pt/TiO2 (Pt = 1.0 wt%) [38]. We determined the chemical yields [39]. The CH4max of 2d was determined to be 0.27 along with 2.9 of H2max and 1.7 of CO2max values. The total yield was calculated to be 100% (=100 (2.9 + 4 × 0.27)/4) in the sacrificial H2 production using 2d. Considering the experimental error, stoichiometric equation for conversion of 2d into H2, CH4, and CO2 was shown in Eq. (8):
\nIt was thought that pyruvic acid (2e) was an intermediate of degradation process from 1c to 2c. The H2max, CO2max, and CH4max values of 2e were found to be 3.9, 2.7, and 0.3, respectively [39]. Degradation scheme of 2e can be expressed by Eq. (9). The yield for the sacrificial H2 production using 2e was 100%. Since the degradation yield of 1c was found to be 87%, the degradation of 1c to H2, CO2, and CH4 proceeded effectively through the formation 2e followed by 2d:
\nThe next sacrificial H2 production was examined using 1d. Oxidation of 1d with hydroxyl radical was initiated by oxidation of primary alcohol part to afford lactic acid (2f). Sacrificial H2 production using 2f produced H2, CH4, and CO2. The H2max, CO2max, and CH4max values of 2f were 4.1, 2.3, and 0.30, respectively. On the other hand, the H2max and CO2max values of 1d were determined to be 4.8 and 1.0, respectively. Trace amount of CH4 was formed. Thus, complete decomposition of 1dinto H2 and CO2 did not take place. Therefore, it is speculated that degradation of 1d proceeds via 2f which was decomposed to acetaldehyde. It is suggested that oxidation of acetaldehyde by hydroxyl radical was slow.
\nIn sacrificial H2 production using 1e, H2max and CO2max values of 1e were 4.2 and 0.50, respectively. Moreover, malonic acid (2g, m/z 104 (M+)) was detected in LC-MS of the photolysate. The sacrificial H2 production using 2g showed that the H2max, CO2max, and CH4max values were determined to be 2.6, 2.7, and 0.31, respectively. Degradation scheme of 2g can be expressed by Eq. (10). Although the degradation yield of 2g was relatively high yield (96%), 1e was not completely decomposed, resulting in 0.5 of the CO2max and no CH4 emission. This suggests that the degradation process of 2g is slow:
\nMoreover, sacrificial H2 production was applied to 1f. The H2max and CO2max values of 1f were determined to be 4.1 and 1.0, respectively. CH4 was not formed. It is suggested that the degradation of 1f proceeded via the formation of propanoic acid (2h). The H2max and CO2max values of 2h were determined to be 2.3 and 1.0, respectively. The decarboxylation of 2h and the subsequent oxidation gave acetaldehyde, which was subjected to the further degradation, but it was slow process [39]. In the case of sacrificial H2 production using 1g, acetone was detected by GLC analysis of the reaction mixture. The H2max value was determined to be 1.3 and CO2 was not evolved. Further degradation of acetone did not proceed.
\nBased on these results, the degradation pathways of 1c, 1d, 1e, 1f, and 1g by hydroxyl radical are summarized in Figure 6. Though considerable amounts of CO2were evolved from 1c to 1f, the CO2max (0.5–2.5) did not reach the theoretical values. In the case of 1g, CO2 was not formed at all. Thus, in the case of these polyols which have one or two non-hydroxy-substituted carbons, the H2max and CO2max values did not reach the theoretical values. Therefore, we conclude that sacrificial agents with all of the carbon attached to oxygen atoms such as 1a and 1b continued to serve as an electron source until their sacrificial abilities were exhausted.
\nDegradation pathway of sacrificial agents by hydroxyl radical in the sacrificial H2 production over Pt/TiO2 using propane-based alcohols: 1-hydroxyl-2-propanone (1c); 1,2-propanediol (1d); 1,3-propanediol (1e); 1-propanol (1f); and 2-propanol (1g).
Vegetable oil was mainly composed of the oleic acid (C17H33CO2H) triglyceride whose average molecular weight was thought to be 884 g/mol. At first, since carboxylic acid was included in used oil as impurity, the amounts of NaOH (a g/kg-lipid) which was required to achieve pH of 8–9 were determined. Lipid (ca. 1 mL, 0.884 g) was solved in 2-propanol (10 mL) and neutralized by an aqueous NaOH solution. In this case, a was determined to be 0 g since fresh vegetable oil was used.
\nVegetable oil (150 mL, 136.5 g, 0.154 mol) was set in a reaction vessel. Since usual optimal amount for transesterification of neutral lipid is known to be 3.55 g/kg [11], the amount of NaOH necessary to the transesterification was determined to be 0.485 g (=0 + 0.485 g) by the sum of a g/kg and 3.55 g/kg. Usually, 20% of weight of 1b to vegetable oil is used for BDF synthesis. 1b (30 mL, 23.8 g, 0.743 mol) was mixed with NaOH (0.485 g, 0.012 mol). About half of the mixture of 1b and NaOH was poured in a reaction vessel and then kept at 61°C for 1 h under stirring. Moreover, the remaining mixture of 1b and NaOH was added into the reaction vessel, and the reaction mixture was kept at 61°C for another 1 h.
\nFollow-up operation is shown in Figure 7. After cooling, the reaction mixture was separated into a lower layer and an upper layer. The lower layer (solution A) contained 1a and 1b. The upper layer was washed with water (300 mL) and separated to the BDF upper layer. Aqueous solution (solution B) was obtained from the lower layer. In order to check the contamination of lipid to BDF layer, the purity of BDF was determined by the peak-area ratio of methyl and methoxy groups in NMR spectra. The BDF layer contained C17H33CO2Me (114.5 g, 0.387 mol) and unreacted vegetable oil (2.2 g). The yield of C17H33CO2Me (BDF) was 83.7% based on the theoretical amounts of 137 g (0.463 mol).
\nMass balance for BDF preparation and the sacrificial H2 production using residual 1a and 1b.
GLC analysis showed that solution A contained 1a (10.4 g, 0.113 mol) and 1b (6.85 g, 0.214 mol) where molar ratio (b) of 1a to 1b was 1.89. The yield of 1a was 73.3% based on the theoretical amounts of 14.2 g (0.154 mol). NMR analysis of solution A showed that RCO2Na (2.2 g) was contained in solution A. Solution B contained 1b (4.38 g, 0.137 mol) and a small amount of C17H33CO2Na. Thus, 1b was found in both solutions A and B.
\nThe photocatalytic reforming of 1a and 1b was examined using solution A. Irradiation was performed by a high-pressure mercury lamp under vigorous stirring with a magnetic stirrer. Figure 8 shows the plots of the H2/1a against the molar ratio of 1a to the catalyst (1a/catalyst), which was adjusted to 0.2, 0.4, 0.6, 0.8, and 1.0. From the intercept of the plots, H2max obtained from 1 mol of 1a at an infinite amount of the catalyst was determined to be 12.52. The yields of H2 production of solution A were determined as follows. According to Eq. (11), the H2 amount (P) was theoretically calculated to be 12.67 using P = 7 + 3b and b = 1.89. Since actual H2max was determined to be 12.52, the yield was calculated to be 98.8% (=100H2max/P). The results are summarized in Table 2:
\nDetermination of H2max values by the plots of H2/1 against 1/catalyst using solution A (◯, b = 1.89) and solution B (◇) obtained from the BDF synthesis.
\n | Residues of BDF synthesisa | \nPhotocatalytic reformingb | \n|||
---|---|---|---|---|---|
\n | 1a/mol | \n1b/mol | \nP c | \nH2max d | \nH2/mol (yield/%)e | \n
Solution Af | \n0.113 | \n0.214 | \n12.67 | \n12.52 | \n1.41 (98.8) | \n
Solution B | \n\n | 0.137 | \n3.00 | \n1.08 | \n0.15 (36.0) | \n
Total | \n0.113 | \n0.351 | \n\n | \n | 1.56 | \n
[ΔH/kJ]g | \n[187] | \n[255] | \n\n | \n | [445] (100.7)h | \n
Photocatalytic reforming of residues of BDF synthesis.
Transesterification was performed by the reaction of lipid (136.5 g, 0.154 mol) with 1b (23.8 g, 0.743 mol) in the presence of NaOH (0.485 g, 0.012 mol) at 61°C for 2 h. BDF (114.5 g) was isolated.
Photocatalytic reforming was performed by irradiation of Pt/TiO2 in aqueous solution of 1a and 1b obtained from solutions A and B.
The values were the theoretical amounts (P) obtained from Eqs. (11) and (12).
The limiting amount of H2 (H2max) was obtained from Figure 8.
The values in parenthesis were the yield of H2 = 100H2max/P.
The molar ratio (b) of 1b to 1a was 1.89.
The combustion energy (ΔH) of 1a, 1b, and H2 were 1654.3, 725.7, and 285.0 kJ mol−1, respectively [16].
The energy recovery yield was calculated to be 100.7% by Eq. (14).
Next, photocatalytic reforming was performed with solution B containing 1b. Solution B was neutralized with dilute H2SO4 in order to reduce the effect of excess NaOH on TiO2. After that, an aqueous solution (150 mL) containing 1b (0.25–1.25 mmol) was irradiated in the presence of Pt/TiO2 (100 mg) in a similar manner as solution A. The plots of H2/1b against the molar ratio of 1b to catalyst (1b/catalyst) are overlaid on Figure 8. The H2max values were determined to be 1.08. The H2 yields were calculated to be 36.0% based on the theoretical P (3.00) [Eq. (12)]. In solution B, C17H33CO2Na was converted to C17H33CO2H by neutralization. It is well known that the carboxylic acid can strongly be adsorbed on TiO2. Therefore, it is suggested that the adsorption of C17H33CO2H on TiO2 lowered the photocatalytic activity of TiO2. The presence of C17H33CO2H retarded the H2 production of solution B remarkably.
\nTotal amount of H2 from solutions A and B was calculated to be 1.56 mol by Eq. (13) using 0.113 mol of 1a in solution A and 0.137 mol of 1b in solution B: 0.113 × 12.52 + 0.137 × 1.08 (Table 2). H2 (1.56 mol) whose combustion energy (ΔH) was 445 kJ was evolved from solutions A and B. The ΔH of H2 was compared with ΔHof 1a and 1b. As shown in Table 2, 0.113 mol of 1a and 0.351 mol of 1b were isolated from BDF synthesis which had 442 kJ of ΔH. The energy recovery yield was calculated to be 100.7% by using Eq. (14):
\nSacrificial H2 production can produce H2 in aqueous solutions. Gaseous H2 can be spontaneously isolated from reaction mixture without being separated. Therefore, sacrificial H2 production will provide a promising approach in the utilization of 1a and 1b derived from BDF synthesis.
\nRecent trends are shifting to the development of solar light-responsive photocatalysts. For example, nanotube-type Pt-N/TiO2 (1 wt% Pt) was applied to sacrificial H2 production with 1a where quantum yield for H2 evolution reached 0.37–0.36 [27]. CuO/TiO2 (1.3 wt% of CuO) was used for sacrificial H2 production using 1a [40]. Heteroatom (B, N)-doped Pt/TiO2 catalyst produced H2 in 88.7–90.9% yields from 1a under xenon lamp irradiation [41]. The B, N-doped Pt/TiO2 had absorption in visible light region (400–500 nm). Photo-reforming of 1a over CuOx/TiO2 (Cu = 0.01–2.8 wt%) gave H2 under visible light irradiation [42]. H2 production was performed over a CuO-TiO2 composite using 1a and 1b under sunlight irradiation [43]. Sacrificial H2 production over Ag2/TiO2 from 1a was performed by irradiation with a xenon lamp [44].
\nBDF market has significantly increased to adhere to energy and climate policies [45]. If H2 is produced by a photocatalytic process using solar energy and biomass-derived sacrificial agents, it will be the most promising process to construct clean BDF synthesis.
\nThe authors declare that they have no competing interests.
During the past thirty to forty years, and along with the global rise in life expectancy, neurodegenerative diseases of the brain that affect the elderly in particular have become a burden on society more and more. The European Union (EU) Joint Programme-Neurodegenerative Disease Research (JPND) states that by the year 2030, a quarter (25%) of the European population will be over age 65, a significant increase over the current 16% [1]. Thus, the scientists place a special focus on age-related neurodegenerative diseases (ADD) research. These ADD such as Alzheimer’s Disease (AD) and Parkinson’s Disease (PD) have become more common and have drawn a lot of attention due to their irreversibility and lack of effective treatment [2]. Neurodegenerative diseases (DD) are known by gradual damage in neural cells and neuronal loss, which conduct to impaired motor or cognitive function. Largely, treatment is accomplished by reducing symptoms more than researching disease physiology and heading to the mechanisms that limit disease progression [3]. The mediating pathogeneses in neurodegenerative diseases are still not fully illustrated; however, great evidence demonstrates that reactive oxygen species (ROS) could be a key event as an elevated level of oxidative stress (OS) has been observed in the brain of DD patients [4]. In recent decades, a broad range of studies has shown that the development of age-dependent neurodegeneration is due to a decrease in the antioxidant efficacy and an increase in oxidative damage. Cumulative ROS can cause damage to biomolecules such as lipids, proteins and DNA, in addition to mitochondrial dysfunction [5]. The increasing prevalence of DD and their profound hindrance to the quality of patient’s life make it necessitous to come up with effective and novel treatment approaches, such as enhancing glutathione level in neurons. Glutathione (GSH) is a major antioxidant whose levels are found to decrease in aging as well as in DD. Scientists are currently heading to fully understand the role of GSH depletion in these diseases in addition to exploit that to develop GSH-based treatment. Glutathione is an essential cellular component, as it is primarily responsible for protecting and defending cells against any risk caused by exposure to ROS, and this role is evident, especially in the brain. Thus, GSH homeostasis disturbance and GSH-dependent enzymes inactivation lead to the breakdown of the main protective barrier against ROS and as a result, the cell becomes more vulnerable to the damage caused by OS [6].
In this chapter, we highlighted the OS in terms of its stimulating effect on the initiation and development of common ADD. We also demonstrated the great importance of glutathione in preserving nerve cells from the damage that OS may cause and the intracellular changes resulting from its depletion that may exacerbate the disease.
Although the human brain makes up only 2% of the body’s weight, its oxygen requirements are estimated at 20% of the body’s oxygen consumption. The brain is classified among the most generating organs for the reactive oxygen species (ROS), where 4% of the oxygen consumed by the mitochondria is converted into super oxide superoxide ion (O2•–), which possesses exceptionally high reactivity, particularly as a powerful oxidizing agent and an initiator of radical reactions. There are three radical reactions mainly initiated by superoxide “Figure 1” (i) under the influence of superoxide dismutase (SOD), the superoxide is converted into hydrogen peroxide (H2O2), which is subsequently converted to water and molecular oxygen by GSH peroxidase (GPx) or catalase. (ii) H2O2 can also react with iron, found in high concentration in brain, via the Fenton reaction to form hydroxyl radicals (OH.), which trigger lipid peroxidation. (iii) Superoxide also interacts with nitric oxide, which is formed in large quantities in the brain by an enzyme neuronal NO synthase (nNOS). This reaction is a million times faster than Fenton and produces the toxic oxidant peroxynitrite (ONOO−), which can spread 10,000 times farther than hydroxyl radicals. Harmful effects of ONOO− are varied including oxidation of macromolecules (DNA, proteins, lipids), nitration of amino acids and inactivating mitochondrial enzymes leading to mitochondrial dysfunction. It is now possible to detect specific markers that are byproducts of the oxidized endogenous macromolecules. For instance, 4-hydroxyl 2, 3-nenonal (HNE) is a marker of unsaturated lipid oxidation, which it has many cellular toxic effects such as irreversible formation of protein adduct and inhibition of GPx activity, and thus contributes in elevated levels of H2O2 [7].
Generation of ROS and Implication of glutathione in ROS/RNS elimination. As a result of mitochondrial respiration, the superoxide (O2-) is generated from O2. This latter can be converted into hydrogen peroxide (H2O2) by superoxide dismutase (SOD). A number of other ROS such as hydroxyl radicals (·OH) and hydroxyl anions (OH-) can be produced from H2O2. Hydroxyl radical and nitric oxide or peroxynitrite may interact directly with GSH forming GSSG. GSH serves as an electron donor for the reduction of H2O2 or other peroxides, catalyzed by GPx, and as result, it is converted to GSSG.
A large body of evidence demonstrates a particular susceptibility of neurons to ROS because of their distinctive characters: High energy demands, high oxygen consumption, high levels of iron, polyunsaturated fatty acids and, in particular, low anti-oxidative protection [8]. The defense enzymatic system in neuronal cells is weak where the SOD, catalase, and GPx activities are low compared to other organs. In addition, glutathione, an essential anti-oxidant component, is present in the brain at low concentrations. These findings suggest the involvement of ROS in neurodegenerative diseases [4, 8, 9].
The OS was one of the important axes of research conducted to understand the pathogenesis of neurodegeneration. A number of research confirmed a strong involvement of oxidative stress in the pathophysiology of neurodegenerative diseases through a variety of mechanisms including induction of oxidation of macromolecules such as nucleic acids, proteins, lipids, mitochondrial dysfunction, glial cell activation, amyloid β deposition, apoptosis, and proteasome dysfunction [3, 5, 10, 11]. A systemic review showed that these mechanisms of neurodegeneration are involved in many harmful cellular pathways. It has been observed that the interference in these pathways in complex ways has the greatest impact on disease development [12], apoptosis, cytokine production and inflammatory responses, and proteasome dysfunction. Currently, there is an increasing focus on the effects of OS on the pathogenesis of neurodegenerative diseases (DD) and the effectiveness of antioxidants as a promising treatment for DD.
Glutathione (GSH) is a thiol-containing tripeptide of major significance in normal brain function. GSH is formed from glutamate, cysteine, and glycine. The γ-carboxyl group of glutamate links the N-terminal glutamate and cysteine residues, unusual peptide bond. This specific peptide bond protects GSH against cleavage by intracellular peptidases preventing its hydrolysis and making GSH moderately stable in the cell. In addition, the presence of the C-terminal glycine residue in GSH structure prevents its cleavage by intracellular γ-glutamyl cyclotransferase. The cysteine residue is an effective functional component of GSH as it provides thiol group, a principle responsible for the GSH activity. Moreover, cysteine residues form the intermolecular dipeptide bond in the oxidized form of GSH. Glutathione disulfide (GSSG), the major oxidized form, involves two residues of GSH that have been oxidized and connected by an intermolecular disulfide bond.
GSH is present in brain at elevated concentration (2–3 mM) compared to blood (15 μM) and cerebrospinal fluid (CSF) (5 μM) [13, 14]. Some evidence has been demonstrated that GSH is very poorly transported intact across the blood-brain barrier (BBB). However, it is probable that the blood is not the major source of cerebral GSH. This indicates that there is an avid brain system assures its synthesis in situ [15].
Generally, for maintaining GSH homeostasis in brain, there are at least two possible mechanisms: (i) glutathione constituents (cysteine moieties) may be recovered and recycled during the turnover of GSH in the brain, and (ii) precursors for brain glutathione synthesis (cysteine, cysteine-containing molecules) might be transported across the blood-brain barrier [13]. Cysteine is the rate-limiting substrate for neuronal GSH synthesis [15, 16]. In contrast, the availability of glutamine or glycine does not limit neuronal glutathione synthesis [13]. Therefore, cysteine alone is the crucial amino acid for neuronal GSH synthesis [17]. The neuronal uptake of cysteine is mediated by sodium-dependent systems, mainly the excitatory amino acid transporters (EAATs) [18]. EAATs have a significant function in removing extracellular glutamate in the CNS [19]. EAAT can transport not only excitatory amino acids, for example, glutamate and aspartate, but also cysteine, in particular, EAAT3, also known as EAAC1 that can transport cysteine at a rate comparable to that of glutamate [19].
Cystine, an oxidized form of two cysteines with a disulfide [20] linkage, is other source of free cysteine and employed as a substrate for GSH synthesis in some types of brain cells. Cystine moieties are transported into brain as (i) γ-glutamylcystine or as (ii) cystinylbisglycine which are possible origins of GSH in brain [21]. Cystine is especially important in maintaining glutathione levels in astrocytes [22], while it has no significance in the synthesis of neuronal GSH due to the inability of neurons to uptake it. Therefore, Content of cysteine or cysteine precursors determines the glutathione level in neurons since neurons are not able to use the cystine but rather rely on the availability of cysteine for their glutathione synthesis [20]. In addition to cysteine, neurons can utilize the cysteine donors such as CysGly, γGluCys, and N-acetylcystein (NAC) as precursors for glutathione. The presence of methionine does not increase neuronal glutathione levels [23]. Methionine is the main precursor of cysteine in liver, which supplies 50% of the cysteine needed for GSH synthesis. However, its role in producing cysteine in the brain is negligible and thus the neuronal GSH synthesis is not related to supply of methionine [16]. Among the exogenous precursors of glutathione, the dipeptide CysGly may be the most important. CysGly is efficiently utilized by neurons in micromolar concentrations [24].
Astrocytes store and synthesize high levels of GSH compared to neurons [13, 25, 26]. This is explained by the inability of neurons to directly uptake GSH. As well as, neurons utilize cysteine, not cystine, for GSH synthesis, whereas astrocytes utilize both [27, 28]. According to the above, neurons rely mainly on astrocytes to supply the necessary cysteine to neuronal GSH synthesis. GSH, released by astrocytes, undergoes a cleavage process by γ-glutamyl transpeptidase (γGT) [29] producing a γ-glutamyl moiety and a dipeptide CysGly which is an essential precursor of neuronal glutathione. The dipeptide CysGly could be uptake into neurons via a peptide transporter as has been described for astrocytes [30]. The dipeptide CysGly is hydrolyzed, upon entry into the neuron, by a neuronal ectopeptidase, providing cysteine and glycine [20] which subsequently are taken up as precursors for glutathione synthesis. Glutathione is synthesized by two successive enzymatic steps dependant on ATP [13, 20]. the first step include γ-glutamylcysteine synthetase (GCL) which mediates the first reaction between glutamate and cysteine to form a dipeptide, γ-glutamylcysteine (γGluCys) which in turn combines with glycine to produce GSH. When a sufficient amount of glutathione is synthesized, a feedback occurs where GCL is inhibited [31]. Conversely, GSH depletion causes in the short term an increase in GCL activity and consequently an increase in GSH synthesis.
The adult mammalian brain has a great demand for energy, and it almost relies entirely on metabolism of glucose. Most of the glucose is completely oxidized to carbon dioxide to meet energy requirements. This very high ability to oxidize glucose indicates that the brain may produce ROS at a remarkable rate. This increase in ROS production combines with low levels of defense mechanisms such as catalase and a high lipid content in brain. All of these indicate that the brain may be particularly vulnerable to OS.
GSH plays a leading role in reducing high levels of ROS and minimizing oxidative damage in brain (Figure 1). This importance has been established by several studies demonstrating that OS was aggravated by the GSH depletion, while increased intracellular GSH improved this damage [32]. GSH is a great component that provides protection against OS in brain by a direct interact with superoxide [33], NO [34], hydroxyl radical [35], and ONOO− [36]. The GSH capacity to scavenge superoxide is higher than NAC or cysteine [37]. Moreover, GSH is a principle hydroxyl radical scavenger because of unavailability of enzymatic defense against these radicals. On the other hand, GSH participates in enzyme-catalyzed redox cycling. The most important enzyme in glutathione redox reaction is glutathione peroxidase (GPx) due to its leading role in the reduction of toxic H2O2 (or lipid peroxide, ROOH) to H2O (or ROH). GSH serves as an electron donor for the reduction of H2O2 or other peroxides, catalyzed by GPx, and as result, it is converted to GSSG [21]. The glutathione redox cycle, is completed by glutathione reductase (GR). This GSH redox cycle takes place in the cytosol and mitochondria, whereas GSH is compartmentalized in mitochondria [38], the major intracellular source of ROS [39], after its synthesis in cytosol. Catalase also reduces H2O2 to H2O but it is unable to detoxify lipid peroxides and is not exist in mitochondria of most tissues. For these reasons, GPx is especially significant in protecting of mitochondria against H2O2,that are constantly generated during cell respiration [40, 41]. Mitochondria contain 5–15% of total cellular GSH [42]. The maintenance of this mitochondrial GSH pool occurs through the action of a high-affinity GSH uptake system [43] which is a main determinant of neuronal susceptibility to OS [44]. Depletion of this pool in brain mitochondria makes them more vulnerable to toxic effects of H2O2 leading to irreversible damages [45] and death. If mitochondria are not protected against OS insult, the organelles become irreversibly damaged through a process culminating with induction of a mitochondrial permeability transition (mPT) which is associated with the collapse of mitochondrial membrane (ΔΨ) and colloid osmotic swelling of the matrix [46]. As well, GSH detoxifies many agents that can induce the mPT in brain mitochondria including 4-hydroxyhexenal (a lipid peroxide) [39]. These findings indicate that GSH has a high significance in maintaining mitochondrial integrity in brain and other organs. Moreover, GSH is a substrate for glutathione S-transferase (GST) that catalyze GSH-dependent reduction of lipid peroxides. In addition to the above, there is a potential synergistic relationship between reduced glutathione and vitamin E, another line of defense. This vitamin is well recognized as antioxidant incorporating into cellular membranes to inhibit lipid peroxidation [47]. Lipids are protected against ROS by α-tocopherol (vitamin E), which quenches ROS and by that, converts to α-tocopheroxyl radical. This latter can re-reduced non-enzymatically to α-tocopherol by GSH [48]. This reaction and those that are catalyzed by GPx and GST possess peroxidase activity and form a protective barrier of the brain against damaging effects of H2O2 on polyunsaturated fatty acids in biomembranes (lipid peroxidation) [49].
Many of studies have been demonstrated the specific toxicity of Hydrogen peroxide to brain [42, 43, 50]. This peroxide induces apoptosis in neuronal cells which are particularly sensitive to its toxic effects [51]. Nevertheless, neurons can detoxify H2O2, but apparently this capacity is more greater in astrocytes for which they play a putative role in the modulation of the neurotoxic effects of H2O2 [45, 46, 52]. The neuronal defense system against H2O2 is mainly based on glutathione redox cycle. This role of GSH is clearly illustrated by a rapid oxidation of GSH when H2O2 is applicated to neurons [53]. Intracellular GSH depletion enforces mitochondrial damage and causes cell death. Apoptosis has been hypothesized to be mediated through the induction of free radicals via oxidative pathways. Thus, a direct cause/effect relationship between GSH depletion and apoptosis was evidenced in neuronal cell [54]. In addition, GSH depletion is an early hallmark in the progression of cell death [55].
It has been previously emphasized that the breakdown of the balance between ROS and antioxidant defense systems is the main manipulator triggering the initiation or progression of a number of common neurodegenerative diseases such as Parkinson’s (PD) and Alzheimer’s (AD) diseases. Each of these diseases depends on a number of factors including mainly OS. However, the causative link between OS and neurodegeneration is not in the scope of this part as it focuses on the dysregulation of the GSH-based antioxidant network in the context of common neurodegenerative diseases: Parkinson’s disease, Alzheimer’s disease [6].
The primary pathologic hallmarks of PD are loss of dopaminergic neurons located in an area of the brain called the substantia nigra pars compacta, and the presence of Lewy bodies, intracellular aggregates of misfolded α-synuclein, in dopaminergic neurons and likely contribute to the death of these neurons. Neurons in the substantia nigra pars compacta produce dopamine, a neurotransmitter (chemical messenger) that transmits signals from the substantia nigra to other parts of the brain. These other parts of the brain are collectively called the “basal ganglia”. Communication among neurons of the substantia nigra pars compacta and the basal ganglia produce smooth, purposeful movement. When the neurons in the substantia nigra are damaged in large numbers, the loss of dopamine prevents normal function in basal ganglia and causes the motor symptoms of PD: tremor, rigidity, impaired balance, and loss of spontaneous movement [56].
Dopaminergic SN cells are usually pigmented with black neuromelanin, produced from of the autoxidation [57] or enzyme-mediated oxidation [58] of the cytoplasmic dopamine (DA) to DA-o-quinone, which then Polymerizes. Usually, this process is accompanied with production of H2O2 rendering dopaminergic SN cells are particularly sensitive to OS probably. It has been reported that dopaminergic SN neurons having high basal levels of DA oxidation, heavily pigmented, is particularly vulnerable to degeneration in PD [59].
A massive loss of nigral GSH is the most notable distinctive changes that occur in the earliest stage [60] in the parkinsonian SN. This GSH loss is uncorrelated to altered activities of biosynthetic enzyme and not accompanied by an increase in GSSG levels [61]. It has been indicated that the drastic drop in GSH is attributed to raise in activity of γ-GT, causing an increased removal of both GSH and GSSG from cells [61]. It is interesting that GSH depletion is characteristic to the parkinsonian SA and is not observed in other neurodegenerative disorders of the basal ganglia [62].
GSH depletion cause indirectly formation of endotoxins in the cytoplasm of pigmented SN cells that contribute to the degeneration of these neurons in PD “Figure 2.” As previously mentioned the activity of γ-GT is up-regulated significantly in the parkinsonian SN [61]. This enzyme is involved in translocation of free cysteine into dopaminergic SN neurons and expulsion of GSH out of these cells. Thus, the profound loss of nigral GSH, main storage form of cysteine, makes the free cysteine, which is increasingly transported into the cell, more likely to bind to oxidizing dopamine and formation DHBTs (dihydrobenzothiazines) by a series of consecutive reactions [63]. These compounds are lethal and evoke profound neurobehavioral responses, especially DHBT-1 which cause irreversible inhibition of mitochondrial complex I [64].
Consequences of GSH depletion in SN dopaminergic neuronal cells in PD. Drastic loss of GSH is associated with protein aggregation which form Lewy bodies, mitochondrial dysfunction resulted from inhibition of complex I activity and oxidative damage including protein oxidation and the deleterious effects of the lipid peroxidation by-product 4HNE.
The presence of Lewy bodies, aggregated misfolded α-synuclein, in SN is also characteristic hallmarks to PD which mainly participate in neurodegeneration [65]. The plurality of intracellular proteins is degraded by the ubiquitin (Ub)–proteasome pathway (UPP). In this pathway, the protein Ub, belongs to a family of heat shock proteins (HSPs), is covalently bound by thiol groups to misfolded or damaged proteins and contributes in their breakdown by transferring them to the protease 26S complex. There are three enzymes contributing to UPP: E1 (Ub-activating enzyme) and E2s (Ub-carrier) prepare Ub for conjugation, but the main enzyme in the process is the E3 (Ub-protein ligase) which transfers the activated ubiquitin to the protein substrate to be degraded [66]. Any defect in the components of UPP or a lack of their activity result in accumulation of α-synuclein protein and subsequent aggregation leading in turn to the formation of Lewy bodies. The depletion in GSH in dopaminergic SN neurons leads to decreased E1 activity and subsequent UPP disturbance [67]. This finding indicates that GSH protects the active sites of these enzymes from being oxidized during oxidative stress, and thus keeps them performing in the Ub-proteasome pathway.
Additionally, the early GSH loss in parkinsonian SN accompanied by increased OS leads to raise in oxidized proteins. In the early stage of PD, HSP proteins are expressed at high levels to prevent the deleterious effects resulting from accumulation and aggregation of damaged proteins in dopaminergic neurons. As the disease progresses, these defenses become unable to control the build-up of protein aggregates [68].
OS also target the mitochondria and interfere with all of their functions. Mitochondrial disorders occupy a crucial place in the mechanisms that mediate neurodegeneration associating with the pathology of PD [69]. Since glutathione is the main component in detoxification of hydroperoxides in mitochondria, its depletion in the brain is believed to promote mitochondrial insult most likely via increased ROS. The mitochondria are known by their vulnerability to OS that might interfere with all of their functions. By serving as the main component in detoxification of hydroperoxides in mitochondria, GSH may reduce the oxidative insults that affect mitochondria. GSH depletion in the brain therefore is believed to promote mitochondrial insult most likely via increased ROS [70].
In synaptic mitochondria, the major role in control over oxidative phosphorylation is attributed to complex I that at 25% inhibition, energy metabolism is disturbed and ATP synthesis is drastically affected. To manifest similar effects [71], complex III and IV inhibition up to 80% is necessitated. The reduced complex I activity in the SN is known as a considerable biochemical characteristic in Parkinsonian brain [72]. Evidence suggest that Early depletions in nigral GSH levels may be directly lead to mitochondrial complex I activity inhibition and subsequent mitochondrial dysfunction which ultimately induces dopaminergic cell death related to PD. The complex I is the most severely influenced mitochondrial enzymes during OS [73]. It is believed that OS, due to decreased GSH availability in the brain, is the major responsible of mitochondrial complex I activity inhibition. This susceptibility of complex I to OS might be explicated by the oxidation of thiol (SH) groups of protein and the existence of accessible oxidation sensitive iron-sulfur centers in this complex [74].
It is recognized that GSH controls the activity of thiol-dependent proteins by keeping the SH groups of protein in a reduced state and preventing them from oxidation [75]. GSH conjugates with oxidized thiol groups to form protein-SS-G and subsequently can be re-reduced to protein and GSH by GR, thioredoxin or protein disulfide isomerase. In addition, GSH, present in dopaminergic cells, can bind to quinones resulted from dopamine oxidation preventing their reaction with SH groups in protein [76].
Lastly, during oxidative insult, aldehydes are formed as a byproduct; the most common of these types is 4HNE. This latter is able to incorporating into the membranes causing changes in their fluidity [77]. In addition, 4HNE can form adducts with important proteins like Na/K ATPas making them inactive. GSH may help reduce the levels of 4HNE by conjugating it via GST. In the PD brains, the loss in GSH in the SN results in high levels of 4HNE adducts [78].
AD, the most common age-related neurodegenerative disease, is known by progressive dementia affecting older populations. This disease is pathologically characterized by depositions of amyloid β (Aβ) plaques and neurofibrillary tangles (NFTs) [14]. The presence of amyloid plaques, which are mainly composed of Aβ peptide, in the extracellular space of AD brain is a main hallmark of disease. The excess of Aβ levels, especially Aβ 42, the most neurotoxic peptide, causes the emergence of familial forms of Alzheimer’s disease. This increase in Aβ 42 leads to the formation of soluble oligomers, causing permanent changes in synaptic function. In parallel, Aβ 42 is aggregated forming mostly β-sheet rich fibrils that enhance local inflammatory responses (microgliosis and astrocytosis). Synaptic spine loss and neurotic dystrophy are also observed. Over time, these events result in a biochemical changes including oxidative stress, altered ionic (e.g.; calcium) homeostasis [79]. Amyloid plaques are the determining factor in triggering a signaling pathway leading to AD progression. Recent evidence suggests that Aβ plaques induce neuronal apoptosis in the brain and in primary neuronal cultures, and this Aβ-induced neuronal death may be responsible in part for the cognitive decline found in AD patients. In addition, aggregated Amyloid-β activates the p38 mitogen activated protein kinase (MAPK) in cell leading to hyperphosphorylation of protein Tau and formation of neurofibrillary tangles (NFTs) inside neurons, making the microtubules unstable and causing the loss of neuron functionality [80].
Evidence demonstrates that Soluble Aβ oligomers are able to block the EAAC1-mediated cysteine uptake leading to a GSH loss in cultured human neuronal cells [81]. This is supported by autopsy brain of AD patients, which exhibit aberrant EAAC1 accumulation in pyramidal neurons of the hippocampus [82] and decreased GSH/GSSG ratios with the progress of disease [83].
Based on the above, it is possible to emphasize the notion of EAAC1 dysfunction in Alzheimer’s disease.
Oxidative stress is considered a major pathogenic factor in AD. Since GSH depletion is of immense implication in oxidative stress, it is expected to have a role in the emergence and development of the disease. A recent clinical study using NMR spectroscopy showed that GSH level is depleted in AD patients as compared to healthy subjects [84]. This finding may have a profound clinical significance. In addition, the analysis of the blood samples of AD patients showed a decrease of GSH concentration in red blood cells compared to age- and gender-matched controls [85]. This is also observed in mild cognitive impairment (MCI) which is a preclinical stage of AD. MCI patients showed a decrease in GSH/GSSG ratios and GST activity in the hippocampus compared to healthy age-matched controls [86]. According to these results, it is suggested that disturbances in GSH metabolism precede the onset of AD. Genetic polymorphisms in the GPx-1 and GST genes were identified as positive risk factors for AD [87]. This can be the reason of decreases in GPx and GST activities in AD [88].
As was previously mentioned, ROS formation is induced by Aβ aggregating and cause a number of oxidative damages and metabolic insults including generation of HNE in hippocampal neurons, which could in turn mediate the toxicities of such insults [89]. Several studies have been shown an increase in lipid peroxidation in the brain of AD patients compared with age-matched controls [90]. As a result of lipid peroxidation, HNE, secondary bioactive aldehyde, is produced at a high levels in several brain regions of late-stage AD subjects [89]. The significant role of HNE in the progression of AD is supported by many findings. Accordingly, an increased level protein-bound HNE in brain of MCI patients was observed [91]. Many proteins were found to be significantly HNE-modified in AD such as ATP synthase, glutamine synthase, DRP-2, and MnSOD. These proteins have a great implication in the regulation of structural functions of brain cell in addition to a number of cellular functions including cellular signaling, energy metabolism and detoxification. Evidence showed that GSH could prevent oxidative damage induced by Aβ and HNE in cultured neuronal cells. This finding suggests that GSH depletion exacerbates oxidative insults stimulated by Aβ and HNE and therefore accelerates the development of the disease.
GSH is an interesting subject studied intensively in the brain for the past several decades. The purpose of such research is not only to understanding the potential role of intracellular GSH in preventing DD progression but also to provide the mechanistic insights contributing to the cellular dysfunctions associated with these diseases. GSH depletion is a common feature of DD triggered by a wide variety of cause including disturbance in GSH homeostasis and modification of the GSH related enzymes. Multiple cellular problems attributed to dysregulation of GSH and GSH-dependent enzymes contributes to impairment in the function of mitochondria, elevation in oxidative damage, disruption of intracellular signal transduction pathways, protein aggregation, and eventually cell death.
It is important to note that further research is necessary to determine more accurately the involvement of disruption of the network of glutathione-dependent reactions in the neurodegenerative events and find new ways to prevent or limit these events. As well to suggest more effective approaches therapy for DD patients.
The author would like to thank team of faculty of pharmacy Al-Baath University, and IntechOpen team.
European union joint programme-neurodegenerative disease research glutathione disulfide glutathione peroxidase glutathione S-transferase glutathione synthetase glutathione reductase Parkinson’s disease Alzheimer’s Disease neurodegenerative diseases reactive nitrogen species reactive oxygen species reduced glutathione oxidative stress 4-hydroxyl 2, 3-nenonal excitatory amino acid transporter C1 excitatory amino acid transporter γ-glutamylcysteine synthetase neurofibrillary tangles
Supporting women in scientific research and encouraging more women to pursue careers in STEM fields has been an issue on the global agenda for many years. But there is still much to be done. And IntechOpen wants to help.
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