Chemical composition and physical properties of cement, fly ash and CRTS.
\\n\\n
Released this past November, the list is based on data collected from the Web of Science and highlights some of the world’s most influential scientific minds by naming the researchers whose publications over the previous decade have included a high number of Highly Cited Papers placing them among the top 1% most-cited.
\\n\\nWe wish to congratulate all of the researchers named and especially our authors on this amazing accomplishment! We are happy and proud to share in their success!
\\n"}]',published:!0,mainMedia:null},components:[{type:"htmlEditorComponent",content:'IntechOpen is proud to announce that 179 of our authors have made the Clarivate™ Highly Cited Researchers List for 2020, ranking them among the top 1% most-cited.
\n\nThroughout the years, the list has named a total of 252 IntechOpen authors as Highly Cited. Of those researchers, 69 have been featured on the list multiple times.
\n\n\n\nReleased this past November, the list is based on data collected from the Web of Science and highlights some of the world’s most influential scientific minds by naming the researchers whose publications over the previous decade have included a high number of Highly Cited Papers placing them among the top 1% most-cited.
\n\nWe wish to congratulate all of the researchers named and especially our authors on this amazing accomplishment! We are happy and proud to share in their success!
\n'}],latestNews:[{slug:"stanford-university-identifies-top-2-scientists-over-1-000-are-intechopen-authors-and-editors-20210122",title:"Stanford University Identifies Top 2% Scientists, Over 1,000 are IntechOpen Authors and Editors"},{slug:"intechopen-authors-included-in-the-highly-cited-researchers-list-for-2020-20210121",title:"IntechOpen Authors Included in the Highly Cited Researchers List for 2020"},{slug:"intechopen-maintains-position-as-the-world-s-largest-oa-book-publisher-20201218",title:"IntechOpen Maintains Position as the World’s Largest OA Book Publisher"},{slug:"all-intechopen-books-available-on-perlego-20201215",title:"All IntechOpen Books Available on Perlego"},{slug:"oiv-awards-recognizes-intechopen-s-editors-20201127",title:"OIV Awards Recognizes IntechOpen's Editors"},{slug:"intechopen-joins-crossref-s-initiative-for-open-abstracts-i4oa-to-boost-the-discovery-of-research-20201005",title:"IntechOpen joins Crossref's Initiative for Open Abstracts (I4OA) to Boost the Discovery of Research"},{slug:"intechopen-hits-milestone-5-000-open-access-books-published-20200908",title:"IntechOpen hits milestone: 5,000 Open Access books published!"},{slug:"intechopen-books-hosted-on-the-mathworks-book-program-20200819",title:"IntechOpen Books Hosted on the MathWorks Book Program"}]},book:{item:{type:"book",id:"7038",leadTitle:null,fullTitle:"Vitamin D Deficiency",title:"Vitamin D Deficiency",subtitle:null,reviewType:"peer-reviewed",abstract:'Vitamin D is the topic for many discussions in the scientific community. Nowadays, a different interpretation of this secosteroid hormone is needed. Today the term "vitamin" may be considered outdated. This compound may be correctly be called a vitamin only when it is administered to humans or animals that suffer from its deficiency. This book attempts to clarify the role of Vitamin D deficiency in many pathological processes in the whole organism. Chapters in this book cover such issues as the earliest clinical and preclinical investigations of the consequences of Vitamin D deficiency for cognitive, cardiovascular, metabolic, immune, and renal disorders.',isbn:"978-1-83880-776-4",printIsbn:"978-1-83880-775-7",pdfIsbn:"978-1-83880-777-1",doi:"10.5772/intechopen.73799",price:119,priceEur:129,priceUsd:155,slug:"vitamin-d-deficiency",numberOfPages:282,isOpenForSubmission:!1,isInWos:1,hash:"ba24f0913341357b0779ff9529c4bbfc",bookSignature:"Julia Fedotova",publishedDate:"February 26th 2020",coverURL:"https://cdn.intechopen.com/books/images_new/7038.jpg",numberOfDownloads:5077,numberOfWosCitations:1,numberOfCrossrefCitations:3,numberOfDimensionsCitations:3,hasAltmetrics:1,numberOfTotalCitations:7,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"May 16th 2019",dateEndSecondStepPublish:"August 26th 2019",dateEndThirdStepPublish:"October 25th 2019",dateEndFourthStepPublish:"November 18th 2019",dateEndFifthStepPublish:"January 17th 2020",currentStepOfPublishingProcess:5,indexedIn:"1,2,3,4,5,6",editedByType:"Edited by",kuFlag:!1,editors:[{id:"269070",title:"Prof.",name:"Julia",middleName:null,surname:"Fedotova",slug:"julia-fedotova",fullName:"Julia Fedotova",profilePictureURL:"https://mts.intechopen.com/storage/users/269070/images/system/269070.jfif",biography:"Julia O. Fedotova, MD, PhD habil., Doc. Biol. Sci, was born in\nSt. Petersburg (Russia), in 1973. She graduated with her Diploma of Pharmacist, Pharmaceutical Faculty, St. Petersburg State\nChemical-Pharmaceutical Academy in 1996. She received her\nPhD in specialties – experimental and clinical pharmacology and\nphysiology of human and animals in 1999. She attended Medical\nSchool, Department of Pharmacology, University of Catania in\n2002, and the Institute of Physiology, Medical School, University of Pecs. She graduated from the special doctoral course in neuropharmacology at the Department\nof Neuropharmacology in the Institute for Experimental Medicine of the Russian\nAcademy of Medical Sciences and she received her doctor of Biological Sciences\n(Ph.D. habil.) in 2008. She is currently a professor at the ITMO University and the\nleading researcher at the I.P. Pavlov Institute of Physiology. She has more 200 publications (mostly in Russian), 2 patents, and 4 journal articles in collaboration, as\nwell as 6 chapters in journals.\nShe is a head of the project “The studying of Vitamin D3 role in development of\naffective-related disorders in women with climacteric period, the search of ways for\npharmacorrection”, from the highly prestige Russian Scientific Foundation.",institutionString:"ITMO University",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"1",totalChapterViews:"0",totalEditedBooks:"1",institution:{name:"ITMO University",institutionURL:null,country:{name:"Russia"}}}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,coeditorOne:null,coeditorTwo:null,coeditorThree:null,coeditorFour:null,coeditorFive:null,topics:[{id:"379",title:"Vitaminology",slug:"alimentology-vitaminology"}],chapters:[{id:"68649",title:"Vitamin D and Its Deficiency in Saudi Arabia",doi:"10.5772/intechopen.88745",slug:"vitamin-d-and-its-deficiency-in-saudi-arabia",totalDownloads:531,totalCrossrefCites:0,totalDimensionsCites:0,signatures:"Fawzi F. 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The use of ultrasound in regional anesthesia has shown the reduction of complications, which makes it mandatory to knowledge and acquire skills in all ultrasound-guided techniques.
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",isbn:"978-1-83969-570-4",printIsbn:"978-1-83969-569-8",pdfIsbn:"978-1-83969-571-1",doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!0,hash:"264f7f37033b4867cace7912287fccaa",bookSignature:"Prof. Víctor M. Whizar-Lugo and Dr. José Ramón Saucillo-Osuna",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/10708.jpg",keywords:"Regional Anesthesia, Ultrasound-Guided Regional Anesthesia, Local Anesthetics, Preventive Analgesia, Peripheral Blocks, Pediatric Regional Anesthesia, Intravenous Regional Anesthesia, Techniques, Complications, Adjuvants in Regional Anesthesia, Opioids, Alfa2 Agonists",numberOfDownloads:null,numberOfWosCitations:0,numberOfCrossrefCitations:null,numberOfDimensionsCitations:null,numberOfTotalCitations:null,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"February 23rd 2021",dateEndSecondStepPublish:"March 23rd 2021",dateEndThirdStepPublish:"May 22nd 2021",dateEndFourthStepPublish:"August 10th 2021",dateEndFifthStepPublish:"October 9th 2021",remainingDaysToSecondStep:"18 days",secondStepPassed:!1,currentStepOfPublishingProcess:2,editedByType:null,kuFlag:!1,biosketch:"Dr. Whizar-Lugo has published more than 100 publications on Anesthesia, Pain, Critical Care, and Internal Medicine. He works as an anesthesiologist at Lotus Med Group and belongs to the Institutos Nacionales de Salud as an associated researcher.",coeditorOneBiosketch:null,coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"169249",title:"Prof.",name:"Víctor M.",middleName:null,surname:"Whizar-Lugo",slug:"victor-m.-whizar-lugo",fullName:"Víctor M. Whizar-Lugo",profilePictureURL:"https://mts.intechopen.com/storage/users/169249/images/system/169249.jpg",biography:"Víctor M. Whizar-Lugo graduated from Universidad Nacional Autónoma de México and completed residencies in Internal Medicine at Hospital General de México and Anaesthesiology and Critical Care Medicine at Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán in México City. He also completed a fellowship at the Anesthesia Department, Pain Clinic at University of California, Los Angeles, USA. Currently, Dr. Whizar-Lugo works as anesthesiologist at Lotus Med Group, and belongs to the Institutos Nacionales de Salud as associated researcher. He has published many works on anesthesia, pain, internal medicine, and critical care, edited four books, and given countless conferences in congresses and meetings around the world. He has been a member of various editorial committees for anesthesiology journals, is past chief editor of the journal Anestesia en México, and is currently editor-in-chief of the Journal of Anesthesia and Critical Care. Dr. Whizar-Lugo is the founding director and current president of Anestesiología y Medicina del Dolor (www.anestesiologia-dolor.org), a free online medical education program.",institutionString:"Institutos Nacionales de Salud",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"5",totalChapterViews:"0",totalEditedBooks:"3",institution:null}],coeditorOne:{id:"345887",title:"Dr.",name:"José Ramón",middleName:null,surname:"Saucillo-Osuna",slug:"jose-ramon-saucillo-osuna",fullName:"José Ramón Saucillo-Osuna",profilePictureURL:"https://s3.us-east-1.amazonaws.com/intech-files/0033Y000033rFXmQAM/Profile_Picture_1611740683590",biography:"Graduated from the Facultad de Medicina de la Universidad Autónoma de Guadalajara, he specialized in anesthesiology at the Centro Médico Nacional de Occidente in Guadalajara, México. He is one of the most important pioneers in Mexico in ultrasound-guided regional anesthesia. Dr. Saucillo-Osuna has lectured at multiple national and international congresses and is an adjunct professor at the Federación Mexicana de Colegios de Anestesiología, AC, former president of the Asociación Mexicana de Anestesia Regional, and active member of the Asociación Latinoamericana de Anestesia Regional.",institutionString:"Centro Médico Nacional de Occidente",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"0",totalChapterViews:"0",totalEditedBooks:"0",institution:null},coeditorTwo:null,coeditorThree:null,coeditorFour:null,coeditorFive:null,topics:[{id:"16",title:"Medicine",slug:"medicine"}],chapters:null,productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"},personalPublishingAssistant:{id:"347258",firstName:"Marica",lastName:"Novakovic",middleName:null,title:"Dr.",imageUrl:"//cdnintech.com/web/frontend/www/assets/author.svg",email:"marica@intechopen.com",biography:null}},relatedBooks:[{type:"book",id:"6550",title:"Cohort Studies in Health Sciences",subtitle:null,isOpenForSubmission:!1,hash:"01df5aba4fff1a84b37a2fdafa809660",slug:"cohort-studies-in-health-sciences",bookSignature:"R. 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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"}}]},chapter:{item:{type:"chapter",id:"59327",title:"Research on Strength, Alkali-Silica Reaction and Abrasion Resistance of Concrete with Cathode Ray Tube Glass Sand",doi:"10.5772/intechopen.73873",slug:"research-on-strength-alkali-silica-reaction-and-abrasion-resistance-of-concrete-with-cathode-ray-tub",body:'For centuries, glass has been one of the main man-made materials that characterize societies. It is part of everyday life in both developed and developing countries. So much consumer glass is regularly produced in the World. However, its disposal creates serious problems because only small percentages of glass are reused or recycled. As a result, most glass products become solid waste and consume ever-scarce landfill capacity [1, 2].
To facilitate problems related to disposal, many countries are currently legislating sustainable waste management and conservation of resources, which includes recycling. In particular, glass has inherent value that can be utilized in numerous applications [3, 4]. Demand for recycled glass has gradually increased in some European countries and North America. Currently, 34% of container glass in Great Britain is recycled, but this rate is far below that in other countries such as Germany, Switzerland, the Netherlands, and Finland where the recycling rates are as high as 80%. In the USA, the rates are considerably less, and millions of tons of waste glass remain as landfill [5, 6].
Adding value to a waste product generates both economic and environmental benefits that are particularly effective if certain inherent properties of a specific waste material are utilized. Concrete is an important construction material that can eliminate certain components of the waste stream with promising results [7]. The most successful and widespread modification is the use of fly ash, slags, and silica fume to partially replace ordinary Portland cement. In addition, other waste stream components such as glass, foundry sands, and rubber are successfully used as concrete ingredients. Studies of glass as an aggregate for concrete have been primarily limited to soda lime glass, which is used for household containers and bottles. On the other hand, studies on the use of LCD glass have also been conducted [8]. The chemical makeup of different glass widely varies even with the glass color, which affects the properties of concrete. In addition, various types of recycled glass can be used in concrete [4].
The recycling of old TV sets and computer monitors with cathode ray tubes (CRTs) poses additional problems. CRTs consist of four structures with different components and properties (screen or panel, cone or funnel, neck and frit junction). Most CRT components contain heavy metals (e.g., Pb, Ba, and Sr) that pose serious environmental health concerns. Thus, CRTs have a notably low recycling rate, which necessitates their disposal in specially engineered landfills [9, 10]. Moreover, depositing glass materials in engineered landfills is expensive [7]. Waste CRTs require a special procedure before they are sent to landfills because of their high lead content. In Hong Kong, a simple method with four steps is used to remove lead on the surface of CRTs: (i) removing the leaded funnel glass from the CRT; (ii) crushing the CRT into small particles of sizes below 5 mm; (iii) cleaning the lead from the glass surface by immersion in a 5% nitric acid solution for 3 h; and (iv) removing the remaining acid by rinsing in tap water [11]. The front panel, which is a component of the CRT, is made of barium strontium glass and is free of lead [12]. CRT can be used instead of raw aggregate if it is known it has good performance on properties and durability in concrete. Using of to CRT replace fine aggregate is possible owing to its close association with natural aggregate as chemical and composition [13].
According to Topçu and Canbaz and Ismail and Al-Hashmi, waste glass concrete exhibits slightly smaller slump values than plain concrete [14, 15]. In a study on workability by Kou and Xing, glass powder minimally decreases the workability according to flow table results [16]. It is expected that glass positively affects the mechanical properties of concrete because of its excellent mechanical properties if it is used as an aggregate or in finely ground powder as a partial cement replacement [2]. Ismail and Al-Hashmi showed that the replacement of sand with glass at up to 20% in concrete can increase compressive and flexural strength [15]. Nevertheless, a glass aggregate content of more than 20% leads to notable decrease in the compressive and flexural strength, ultrasonic pulse velocity and dynamic elasticity modulus [1, 14]. One of the problems encountered when using glass as an aggregate in concrete is glass cracking and progression of these cracks [2, 5, 14]. A smooth glass surface facilitates the movement of the cracks, and this effect decreases the strength [11]. The flexural strength of a mortar specimen with glass aggregate can be 10% less than that of a specimen without glass aggregate. Expansion from 1 to 4 mm in the size of the glass aggregate increases flexural strength from 2.6 to 3.2 MPa. Mortars with 3 and 4 mm glass aggregates have stronger resistance to cracks and exhibit high energy [17]. Investigations are still lacking in the area of abrasion resistance of concrete containing glass aggregates. In studies by Ling and Poon, Turgut, and Turgut and Yahlizade, the replacement of sand with glass aggregates in the mortar increased the abrasion resistance [18, 19, 20]. Use of glass aggregate at up to 20% in concrete resulted in better performance in comparison to plain concrete from the standpoint of material properties [20, 21].
It is also well known that silica in glass can chemically react with alkali in the cement matrix, which is known as ASR. The resulting ASR gel swells in the presence of moisture and causes potentially serious cracking damage [2, 5, 22]. Topçu et al. reported that the ASR caused expansion and internal stresses in the concrete in direct proportion to the amount of glass in the concrete. It was necessary to add 2% Li2CO3 and 20% fly ash to the mix to constrain the expansion below the acceptable limit [22]. As reported by Özkan, clear glass performed better than brown glass in terms of strength and durability. That study also considered mortar with up to 50% blast furnace slag, which replaced Portland cement, and it was found that 25% slag led to the least amount of ASR expansion. Large amounts of fly ash and slag reduced the early strength but significantly increased the alkali resistance of concrete [1]. Polley et al. and Kou and Poon reported that the use of fly ash significantly decreased the influence of the ASR [21, 23]. Lane and Ozyildirim concluded that the strength and durability increased when small amounts of silica fume were used with large amounts of fly ash or slag. ASR tests according to ASTM C1293 indicated that as little as 15% of fly ash was sufficient to prevent detrimental expansion. In addition, a slag ratio of at least 35% was found to be advisable. This performance was also achieved with 25% slag and 2.5% silica fume due to the beneficial combination of silica fume and blast furnace slag [24]. Cota et al. showed that waste glass of 7.5 or 15% did not deteriorate mechanical properties or ASR durability when Portland cement replaced 15% of metakaolin [25]. Ismail and Al-Hashmi noted that it is not always necessary to use pozzolana to prevent ASR. In that study, high-quality pozzolanic waste glass sand (67.72% SiO2 and 6.9% CaO) that was modified with 10, 15, and 20% sand was used. The concrete strength and ASR durability increased with increasing waste glass content [15]. According to Schwarz et al., fine glass dust can improve the durability of concrete [26]. The results of Shayan and Xu indicate that if the glass particle sizes are thinner than 0.30 mm, they will not cause deleterious expansion. Particle sizes above 0.60 mm cause significant deleterious expansion [2]. In their other study by Shayan and Xu, powder glass did not cause ASR because it had pozzolanic properties [27]. According to Meyer, it is possible to reduce ASR expansion depending on the cement and climatic conditions and the structure and thickness of the glass [28]. In addition, because ASR swelling occurs only in the presence of moisture, measures to prevent the ingress of moisture are expected to be effective in preventing ASR damage.
The present study investigated the effects of substituting various amounts of CRT glass for fine aggregates in concrete on the following physical, mechanical, and durability properties: unit weight, workability, water absorption, compressive and flexural strength, ultrasonic pulse velocity, static and dynamic elastic moduli, abrasion, and ASR expansion. The crushed sand replacement by cathode ray tube glass sand (CRTS) constituted 5, 10, 15, and 20% by weight of the total aggregate.
The cement in this study was CEM I/42.5 R according to TS EN 197-1 [29]. Fly ash (FA) was used to increase the resistance against ASR and supply utilization by recycling this waste material. CRTS obtained by recycling computer screens was provided from Exitcom Corp. in Turkey. The chemical and physical properties of the cement, FA, and CRTS used in this study are provided in Table 1. A superplasticizer was also added to ensure concrete workability.
Chemical properties | Physical and mechanical properties | ||||||
---|---|---|---|---|---|---|---|
Constituent (%) | Cement | Fly ash | CRTS | Properties | Cement | Fly ash | CRTS |
SiO2 | 20.5 | 50.2 | 50.9 | Specific gravity (g/cm3) | 3.12 | 2.04 | 2.70 |
Al2O3 | 4.65 | 12.7 | 2.62 | Blaine (m2/kg) | 360 | 212 | — |
Fe2O3 | 3.40 | 9.00 | 0.12 | Mass stability (mm) | 2.00 | — | — |
CaO | 62.7 | 12.53 | 1.54 | Setting period start (min) | 153 | — | — |
Free CaO | 1.09 | — | — | Setting period stop (min) | 188 | — | — |
MgO | 1.02 | 4.33 | 0.64 | 90 μ sieve (%) | 0.20 | — | — |
SO3 | 2.21 | 0.39 | — | 45 μ sieve (%) | 12.8 | — | — |
Na2O | 0.18 | 2.75 | 3.60 | 2 day-strength (MPa) | 30.2 | — | — |
K2O | 0.41 | 2.50 | 4.30 | 7-day strength (MPa) | 51.1 | — | — |
PbO | — | — | 0.29 | 28-day strength (MPa) | 62.2 | — | — |
BaO | — | — | 9.10 | ||||
Sb2O3 | — | — | 0.31 | ||||
ZrO2 | — | — | 0.91 | ||||
SrO | — | — | 5.97 | ||||
TiO | — | — | 0.39 | ||||
CeO2 | — | — | 0.25 | ||||
Cl− | 0.01 | — | — | ||||
Insoluble residue | 0.60 | — | — | ||||
Ignition loss | 2.15 | 0.54 | — |
Chemical composition and physical properties of cement, fly ash and CRTS.
Four different types and sizes of aggregate were used: river sand (0–3 mm), crushed sand (0–4 mm), coarse aggregate 1 (5–12 mm), and coarse aggregate 2 (12–20 mm). The coarse aggregates consisted of crushed stone and their maximum size was 20 mm. Figure 1 shows river sand, crushed sand, and CRTS. The gradation curves for CRTS and the other fine aggregates are shown in Figure 2.
Photographs of CRTS, crushed sand, and river sand used in the study.
Particle size distributions of fine aggregates.
Five different mix designs were investigated, as shown in Table 2. These mix designs contained CRTS in the amounts of 0, 5, 10, 15, and 20% by weight of total aggregate crushed sand replacements. After the workability of fresh concrete was determined for each mix, five cubes of size 150×150×150 mm, five beams of size 100×100×400 mm, five cylinders of 150 mm in diameter and 300 mm in length, five cubes of size 71×71×71 mm, and five prisms of size 25×25×285 mm were cast to determine the compressive strength, flexural strength and pulse velocity, elastic modulus, abrasion, and ASR, respectively.
Components | CRTS content (%) | ||||
---|---|---|---|---|---|
0 | 5 | 10 | 15 | 20 | |
Cement (kg/m3) | 300 | 300 | 300 | 300 | 300 |
Fly Ash (kg/m3) | 60 | 60 | 60 | 60 | 60 |
Water (kg/m3) | 155 | 155 | 155 | 155 | 155 |
Natural sand (kg/m3) | 517 | 517 | 517 | 517 | 517 |
Crushed sand (kg/m3) | 360 | 270 | 180 | 90 | 0 |
CRTS (kg/m3) | 0 | 94 | 188 | 282 | 376 |
Coarse aggregate 1 (kg/m3) | 470 | 470 | 470 | 470 | 470 |
Coarse aggregate 2 (kg/m3) | 512 | 512 | 512 | 512 | 512 |
Admixture (%) | 1.30 | 1.30 | 1.30 | 1.30 | 1.30 |
Water/(FA + C) | 0.43 | 0.43 | 0.43 | 0.43 | 0.43 |
Slump (mm) | 170 | 160 | 158 | 150 | 143 |
Unit weight (kg/m3) | 2379 | 2383 | 2387 | 2391 | 2395 |
Concrete mix designs.
Workability. The slump of fresh concrete was measured using the standard slump test apparatus according to ASTM C143 [30].
Densities and water absorption. Dry, saturated densities and water absorption of hardened concrete were measured according to ASTM C642 [31].
Compressive strength. The compressive strength of the hardened concrete was determined according to ASTM 39 [32] at the ages of 3, 7, 28, and 90 days for the cube specimens of 150×150×150 mm in size. These cubes were removed from the molds after 1 day and cured in water at 21°C before testing.
Flexural strength. The flexural strength of the hardened concrete was determined at the ages of 3, 7, 28, and 90 days for the beams of 100×100×400 mm in size. These beams were removed from the molds after 1 day and cured in water at 21°C before testing. The flexural strength was determined using three-point bending tests according to ASTM C78 [33] with an effective span of 300 mm.
Ultrasonic pulse velocity. The ultrasonic pulse velocity of the hardened concrete was determined by selecting a measurement distance of 400 mm at the ages of 3, 7, 28, and 90 days on the 100×100×400 mm beams. The measurements were performed according to ASTM C597 [34] before the flexural strength tests.
Static and dynamic elastic moduli. The static elastic modulus was determined on 150×300 mm cylinders at the age of 28 days in compression according to ASTM C469 [35]. The dynamic elastic modulus was determined using the 28-day data that were obtained from the ultrasonic pulse velocity of the beams according to ASTM C597, formula obtained from ASTM C597 was used to calculate the dynamic elastic modulus. The formula of dynamic elastic modulus was showed in Eq. (1).
Alkali-silica reaction. ASR was determined on the mortar bars of 25×25×285 mm according to ASTM C1260 [36].
Abrasion. The amount of horizontal surface abrasion was determined on the cubes of 71×71×71 mm using the Bohme testing method according to BS EN 13892–3 [37] after 28 days.
The workability was negatively affected with increasing CRTS content, as shown in Table 2. The slump value slightly decreased when the CRTS content increased by 5%. However, the slump decreased by only 2.75 cm when the CRTS content increased to 20%. According to Ling and Poon, fine particle size glass increases water absorption [38]. Similar to these results, Topcu and Canbaz reported that increasing glass content reduced the workability but the reduction was insignificant [15]. Concrete with glass requires more water to achieve the same workability [5, 21]. Ismail and Al-Hashmi, Kou and Xing, and Shayan and Xu, also reported that glass added to concrete decreases the workability [2, 15, 16].
Table 3 indicates that up to 15% CRTS content in concrete increases the density of hardened concrete in comparison to plain concrete. However, glass content above 15% decreases the density [23]. Changing the glass content from 15 to 20% produces the largest increase in water absorption, which suggests that glass content above 15% leads to higher porosity than specimens without CRTS. The study by Shayan and Xu also indicates that the density decreases with glass addition above 15% as aggregate or glass powder [2]. The dry and saturated density of the concrete exhibits identical trends. Table 4 shows that the water absorption decreases from 6.46 to 6.05 when the CRTS composition reaches 10%. Water absorption increased when CRTS content is higher than 10% in the concrete. This increase is remarkable when the fraction is 20%.
CRTS content (%) | 0 | 5 | 10 | 15 | 20 |
Slump (cm) | 17 | 16 | 15.75 | 15 | 14.25 |
Effect of CRTS content on the workability.
CRTS content (%) | Dry density (kg/m3) | Saturated density (kg/m3) | Water absorption (%) |
---|---|---|---|
0 | 2213 | 2354 | 6.46 |
5 | 2219 | 2363 | 6.26 |
10 | 2289 | 2427 | 6.05 |
15 | 2274 | 2413 | 6.09 |
20 | 2198 | 2354 | 6.97 |
Densities and water absorption of the specimens.
The use of 15 and 20% CRTS decreased the compressive strength in concrete over the first 28 days in Figure 3. The study by Maschio et al. (2013) presents a similar relationship [39]. After 28 days, the rate of increase of strength was faster than that of P and specimens with 5 and 10% glass aggregate and approached these values for 15 and 20% CRTS in concrete [8]. This result demonstrates that the glass contents of 15 and 20% have a pozzolanic effect that becomes more obvious after 28 days [15]. The glass replacements of 5 and 10% do not significantly change either the early or the end strength values in comparison with P [6]. The specimen with 5% CRTS exhibited a notably constant value throughout the period of 90 days, which approached approximately 40 MPa after 90 days. An increase of compressive strength was observed for 10, 15, and 20% CRTS from 28 to 90 days, which can be attributed to the pozzolanic effect of CRTS [40]. Intervals of minimum and maximum compressive strengths for all specimens were 13–24, 22–30, 32–39, and 37–41 MPa for 3, 7, 28, and 90 days, respectively. After 90 days, the difference between the minimum and maximum values of the specimens was relatively small [8]. It is remarkable that the interval decreased from 9 to 4 in 90 days. However, the increase in glass content generally decreases the compressive strength [2]. Ling and Poon explained that the compressive strength might be negatively affected by the bonding between the glass particles and the cement paste [11].
Improvement in compressive strength of the specimens over 90 days.
SEM micrograph in Figure 4 displays the interface between concrete and CRTS exposed to compression. This micrograph was obtained by enlarging the field under SEM 500 times. This SEM micrograph was similar to those reported by Ling and Poon: a smooth surface of CRTS can lead to a weaker interface that results in loss of bonding between CRTS and cement paste, and cracks originating from loading can spread faster [11, 41]. Therefore, the strength of the concrete with glass aggregate decreases [2, 5, 14, 17, 41].
SEM micrographs showing the bond between CRTS and cement paste in concrete after compression loading.
The flexural strength-time graph is shown in Figure 5. The specimen with 5% CRTS replacement is notably similar to the P sample throughout 90 days in terms of the compressive strength. The flexural strengths for the 5% CRTS and P samples on the 28th and 90th days were almost the same. The specimens with 10, 15, and 20% CRTS have similar trends each other. The maximum difference in values of flexural strength on 90th day decreases to 0.7 MPa, whereas it is 1 MPa after 28 days. The flexural strengths of P and 5% CRTS concrete are approximately 5 MPa at 90 day, whereas the others approach approximately 4.5 MPa. The increase in glass content in the mix generally decreases the flexural strength [2, 8, 14].
Improvement in flexural strength of the specimens over 90 days.
The pulse velocity graph in Figure 6 reveals that the specimen with 20% CRTS replacement exhibits relatively low values for the first 28 days in comparison with the others. The specimens with 5 and 10% CRTS replacement exhibit a relatively higher pulse velocity than P for the first 28 days. Their values are almost identical to that of P at the end of 90 days. All specimens have notably similar pulse velocity values at the end of 90 days, and there are also differences between 28 and 90 days, as shown in the graphs of compressive and flexural strengths in Figures 3 and 5. The ultrasound pulse velocity is approximately proportional to the compressive and flexural strengths [2].
Improvement in ultrasonic pulse velocity of the specimens over 90 days.
Static and dynamic elasticity modulus values are very similar in Figure 7. The dynamic elasticity modulus found using the ultrasonic pulse velocity is generally larger than the static elasticity modulus. The specimen with 5% CRTS replacement in concrete has the highest value, and that with 10% glass replacement has a better value than the specimen without CRTS. The specimens with 15 and 20% replacement have notably similar values, which are slightly lower than that of the specimen without CRTS [2, 23]. The elasticity moduli of all specimens are related to the compressive strength, flexural strength, and ultrasonic pulse velocity at 28 days [42].
Static and dynamic elasticity moduli of the specimens at 28 days.
The 21-day expansion of the mortar bars is shown in Figures 8 and 9. In Figures 8 and 9, the expansion can be observed to increase with increasing CRTS content and time. The bars with fly ash in Figure 8 expand slightly less than the bars without fly ash (CRTS-F) in Figure 9 because of the pozzolanic effect of fly ash [43]. After 21 days, all specimens with CRTS have similar values except for the specimens without CRTS. The highest expansion for the specimens with 20% CRTS is less than 0.03% in Figures 8 and 9, which is below the upper limit of 0.1% according to ASTM C1260. The study of Zhao et al. (2013b) also showed the expansion value of FA series mortar samples with glass sand are found to be below 0.1% [44]. The importance of using fine glass was reported by Ismail and Al-Hashmi, who used aggregate with a fineness modulus of 2.36, which decreased the ASR. In this study, the fineness modulus of the CRTS is 2.95, which indicates that the aggregate is sufficiently fine for ASR resistance.
Improvement in ASR of the specimens over 21 days.
Improvement in ASR of the specimens without fly ash over 21 days.
Figure 10 shows the results of abrasion volume loss (%) found using the Bohme abrasion test machine. It clearly appears that the abrasion volume loss (%) decreases with increasing [18, 19, 20, 45]. The research by Turgut and Yahlizade supports these results. They found that the use of glass replacement with fine aggregate up to 20% by weight decreased the abrasion volume loss (%). In this research, the decrease slows down between 5 and 15%; however, Turgut and Yahlizade did not investigate these proportions. The difference of abrasion volume loss of specimen with glass content of 20% compared to the specimen without CRTS is approximately 2.5% in this research; whereas it was 2% in the research by Turgut and Yahlizade. Their study was based on concrete paving blocks and window glass.
Change in abrasion loss (%) of the specimens after 28 days as a function of CRT comparing with the research by Turgut and Yahlizade.
Based on the results of the experimental studies carried out in the research, the results obtained are presented below:
CRTS slightly affects the slump values; an increase in the glass content in concrete reduces the slump value.
CRTS content up to 10% increases the density and decreases water absorption. However, a CRTS content of 20% increases water absorption in the concrete. This shows that the CRTS up to 10% in concrete increases the filling by entering the gaps and introduces voids above 10%.
Increasing the CRTS content decreases the compressive and flexural strengths, except when the content is 5%. Although CRTS content of 15 and 20% reduces the strength, the strength of these specimen increases more than that of the other specimens after 28 days, which indicates a pozzolanic effect. This effect is less observed in specimens with 10% CRTS.
CRTS content of 15 and 20% leads to the lowest pulse velocity values in comparison with the other concrete. The specimens with CRTS content of 5 and 10% exhibit higher pulse velocity compared to the specimens without CRTS until 28 days have passed. All values are close to each other at 90 days.
Static and dynamic elasticity moduli exhibit similar trends to each other and also to the compressive strength at 28 days. The concrete specimens with CRTS content of 5 and 10% have larger moduli than P. The elasticity moduli decrease when the CRTS content reaches 15%. Specimens with 20% CRTS exhibit similar moduli to those with 15% CRTS.
An increase in CRTS content decreases the ASR resistance but not to a problematic level because the level is below the 0.1% ASTM C1260. The specimens with fly ash have lower values than those without fly ash. The use of fly ash in concrete with CRTS has a positive effect against ASR, as expected.
The abrasion volume loss (%) decreases with increasing CRTS content up to 20%. The decrease is approximately 2.5%.
In conclusion, the concrete with CRTS aggregate exhibits a performance similar to that of the concrete without CRTS. This result shows that the use of CRTS can contribute to the properties of concrete. The mixture of CRTS in concrete can be adjusted according to the application and desired specific properties. The performance of abrasion resistance of concrete with 20% CRTS is especially notable. Research is needed on concrete with more than 20% CRTS. Furthermore, the use of CRT funnels in concrete is also an important matter because of their lead content. Lead is harmful to the environment. In this respect, recycling of CRT funnels is important, and there is a need for research on this subject.
The study is notable in terms of the potential use of recycled CRTS because of the quantity of waste CRTS used. Concrete properties can be improved with CRTS, resulting in the reduction of piles of waste CRTs when they are used in concrete.
The author wishes to acknowledge the support of Prof. Dr. Christian Meyer (who has patented the “use of waste glass in concrete”) from the Civil Engineering and Engineering Mechanics Department at Columbia University, who contributed important ideas to this study during a research on internal curing of concrete with the author in Carleton Laboratory at Columbia University.
Over the centuries, humans have depended on nature for their essential needs of food supplies, shelters, apparel, transport means, fertilizers, flavors and fragrances, and the last not but least, medicines. Sophisticated traditional medicine systems have been generated by the plants over thousands of years. Moreover, plants maintain the significant sources of modern remedies for humanity. Additionally, according to WHO, 80% of the world’s population—primarily those of developing countries rely on plant-derived medicines for their healthcare [1]. People continue to consider nature as a source of potential chemotherapeutic agents. Over 50% of clinical drugs all over the world are the product of natural plants and their derivatives. While more than 25% of the total are extracted from higher plants [2].
\nHistory of pharmacy was for centuries identical with the history of pharmacognosy, or study of materia medica, which were obtained from natural sources—mostly plants but minerals, animals, and fungi. Chirality is one of the universal phenomena in nature. For instance, chiral biomolecules such as amino acids, sugars, proteins and nucleic acids have created living organisms. In natural surroundings, these biomolecules are present in one of the two possible enantiomeric forms, e.g., amino acids in the L-form and sugars in the D-form. Living organisms show variation in biological responses to one of a couple of enantiomers in medicines due to the chirality [3].
\nA range of chemicals that accurate enzymatic metamorphosis defines stereochemical configurations. Consequently, there is a certain chirality in most organic compounds in nature. It is important to emphasize that some phytochemicals exist in only one enantiomeric form, while others the optical rotation of the metabolite can be different [4].
\nAlkaloids are cyclic organic compounds that contain nitrogen in a negative oxidation state. They are generally distributed in flora and are an essential role in plant protection, sprouting and stimulating plant growth. Alkaloids-containing plants are often used as traditional medicines and these compounds usually have marked pharmacological activity [5]. Over 21,000 alkaloids have been identified, which thus constitute the largest group among the nitrogen-containing secondary metabolites [6]. Alkaloids are significantly pharmaceutical, e.g. morphine as pain relief medicines, codeine as an antitussive in cough medicines, colchicine in the treatment of gout and familial Mediterranean fever (FMF), Quinine as an anti-malarial and a muscle relaxant, Quinidine, as an
The first isolations of alkaloids in the nineteenth-century new investigation into medicine of several alkaloid-containing drugs and were accidental with the advent of the separation process for the extraction of drugs. In 1803, the French apothecary Derosne probably isolated narcotine. Several years later, the Hanoverian apothecary Sertürner further investigated opium (1806) and isolated morphine (1816) [7].
\nBased on their structures, alkaloids are divided into several subgroups: non-heterocyclic alkaloids and heterocyclic alkaloids, which are again divided into 7 major groups according to their basic ring structure [8]. Families reported to be rich in alkaloids are: Liliaceae, Amaryllidaceae, Apocynaceae, Berberidaceae, Leguminosae, Papaveraceae, Ranunculaceae, Rubiaceae and Solanaceae [9]. Most of alkaloids are chiral compounds and are clinically administered as the racemic mixture, although its enantiomers have been shown to exert different pharmacological activity.
\nPhenylethylamine alkaloids in medicinal herbs (i.e. Citrus species and Ephedra sinica) are used ubiquitously for their effects on the metabolic process of humans by stimulating lipolysis and thus supporting to reduce the fat mass in obese people. Particularly, Ephedra Herba (Ma Huang) contain several alkaloids such as (1R, 2S)-(−)-ephedrine, (1S, 2S)-(+)-pseudoephedrine, (1R, 2S)-(−)-norephedrine, (1S, 2S)-(+)-norpseudoephedrine, (1R,2S)-(−)-N-methylephedrine, and (1S, 2S)-(+)-N-methylpseudoephedrine [10]. Each of these six compounds also has an enantiomer that does not occur naturally in the plant [11, 12]. Separation and quantification of optical isomers of ephedrine-type alkaloids are important since ephedrine-type alkaloids in natural have been found to be strengthened with inexpensive (racemic) synthetic similarity, and these enantiomers could exhibit important differences in pharmacological activities. To diminish essential public health risk, adulteration of Ephedra products could be discovered by the presence of both enantiomers, such as naturally occurring (−)-ephedrine and synthetic (+)-ephedrine in the samples [13].
\nIn the case of C. urantium alkaloids, synephrine has also effect on human metabolism that could help to reduce fat mass in obese people, since it stimulates lipolysis, raises the metabolic rate and promotes the oxidation of fat through increased thermogenesis [14]. Synephrine is a chiral compound and is clinically administered as the racemic mixture, although its enantiomers have been illustrated to apply different pharmacological activity on α- and β-adrenoreceptors. Particularly, (R)-(−)-synephrine is from 1 to 2 orders of magnitude more active than its (S)-(+)-counterpart (Figure 1) [15].
\nMolecular structure of synephrine and ephedrine alkaloids (*chiral center).
Solanaceae contain mainly tropane alkaloids such as atropine, anisodamine and scopolamine; these plants are extensively used both in traditional medicine and as sources for the extraction of the pharmacologically important (parasympatolytic and anti-cholinergic) alkaloids [10]. Atropine is existed in racemic mixture of (S)-hyoscyamine and (R)-hyoscyamine. (S)-hyoscyamine is original in plants and (R)-hyoscyamine forms under alkaline conditions. (S)-hyoscyamine functions competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary and sweat glands, as well as gastrointestinal tract, while the (R)-hyoscyamine is mostly inactive. Atropine, which is more often applied than (S)-hyoscyamine, exhibits approximately half of the pharmacological activity of (S)-hyoscyamine. In reverse, Scopolamine is mostly applied as pure enantiomer, e.g. (S)-scopolamine bromide [16].
\nAnisodamine, a tropane alkaloid isolated from Solanaceae family (Scopolia tangutica Maxim.). In China for decades, Anisodamine is an effective cholinoceptor antagonist and has been used as a spasmolytic drug to effect on smooth muscle by feature of its weaker side effect on the central nervous system than atropine. This kind of alkaloids have biological characteristic including cholinoceptor agonists and antagonists, like most chiral drugs, depend strongly on their stereochemistry. The effectiveness differences among four isomers of anisodamine racemic on muscarinic receptors have been perceived (Figure 2) [17].
\nMolecular structure of (S)-hyoscyamine, (S)-scopolamine, and anisodamine.
Aconitum plants (Ranuncolaceae) are generally distributed across Asia and North America. In the Chinese Pharmacopeia, two species of them, A. carmichaeli Dexb. and A. kusnezoffiiare were listed. Aconitine and the congener mesaconitine and hypaconitine (Figure 3) are the important diester-diterpene alkaloids of aconitum plants. Although they have toxic effects on human health, they can also be used at low doses because their pharmacological effects such as anti-inflammatory and anti-pain are effectively [10].
\nMolecular structure of aconitine, mesaconitine and hypaconitine.
In the legume alkaloids, the largest single group is quinolizidine alkaloids. In distribution to species in the more primitive tribes of the Papilionoideae, they appear to be restricted. Because of their toxicity in humans and animals as components of poisonous plants, these compounds become important. In contrast, some of them are potentially useful in pharmacological activities [18]. Radix sophorae flavescentis (Sophora flavescens) is frequently used in Traditional Chinese medicine for treating acute hepatitis and jaundice; it was found that quinolizidine alkaloids were the main constituents of this herbal drug such as matrine, sophoridine, sophocarpine, lehmannine, sophoranol, oxy-matrine, oxysophocarpine which have some chiral center [10, 19]. In natural, they exist as an isomer, sophocarpine (Figure 4) is an example. The naturally (−)-sophocarpine isolated from the root of the Chinese medicinal herb Sophora flavescens Ait. (Fam. Leguminosae) [20].
\nMolecular structures of four quinolizidine alkaloids.
Bis-benzylisoquinoline alkaloids have fascinated by the significant pharmacological impacts; especially, protoberberines are a structural class of organic cations (quaternary ammonium alkaloids) mostly distributed in Ranuncolaceae (e.g., Rhizoma coptidis), Berberidaceae (e.g. Cortex berberdis), Papaveraceae (e.g. Herba chelidoni) and Rutaceae (e.g. Cortex phellodendri) [10]. The most considered chiral isoquinoline alkaloids are tetrahydroprotoberberine backbone structure such as tetrahydropalmatine (THP), tetrahydroberberine (THB), and corydaline [21]. (DL)-THP and (DL)-THB are highly abundant in C. yanhusuo and a variety of Corydalis plants. (L)-THP can also be isolated from Stephania plants [22]. Tetrahydropalmatine is one of the active ingredients isolated from Rhizoma Corydalis (yanhusuo), a traditional Chinese medicine that has been used for the treatment of chest pain, epigastric pain, dysmenorrhea, traumatic swelling, and pain for thousands of years [23]. The analgesic activity of (−)-THP is much higher than that of (+)-THP. Clinically, THP is used as the racemic mixture (Figure 5) [22].
\nMolecular structures of the enantiomers of tetrahydropalmatine (THP), and tetrahydro-berberine (THB).
Amaryllidaceae alkaloids are an important class of iso-quinoline derivatives; among them galanthamine, that is found in Galanthus and Narcissus species, has been approved for the pharmacological treatment of Alzheimer’s disease [24]. There are several chiral centers in this molecule, but only one S-enantiomer responsible for Alzheimer’s disease, other stereoisomers considered as impurity (Figure 6) [25].
\nMolecular structures of galanthamine.
Morphinane alkaloids (opium alkaloids) such as morphine, codeine, thebaine, papaverine and narcotine belong to isoquinoline derivatives and show a broad range of pharmacological activities; their major application is in analgesia, sedation and cough depression [26]. Although opiate alkaloids have an important place in medicine, the illegal trafficking and abuse of heroin (the diacetyl derivative of morphine) has become a widespread problem [27]. Opium, the exudates from Papaver somniferum, contains more than 30 alkaloids and is the raw material for extraction; also, the dried heads of P. somniferum, so-called poppy straw, is used as a source of morphine and thebaine. Figure 7 show the molecular structure of opium alkaloids, most of them have multi chiral center.
\nMolecular structures of: (1) morphine; (2) codeine; (3) oripavine; (4) thebaine; (5) pseudomorphine.
Although these alkaloids have at present no great medicinal significance, they are important in that they constitute the poisonous hepatotoxic constituents of plants of the genus Senecio (Compositae), well-known for their toxicity to livestock [28]. Pyrrolizidine alkaloids are found in a variety of plant species growing wide world such as Gynura segetum that belongs to the Compositae family and Senecio and Tussilago genera [10]. The majority of naturally occurring pyrrolizidine alkaloids (PA) are hepatotoxic causing liver damage and in some cases liver cancer. Toxic PAs are often responsible for serious health problems through direct consumption of PA-containing herbal teas, herbal medicines, and herbal dietary supplements [29].
\nThe most important pyrrolizidine alkaloids senecionine, seneciphylline, retrorsine and senkirkine, contain the 4-azabicyclo [3.3.0] octane system with senecionine and seneciphylline differing only for the presence in the latter of the C13-C23 double bond (Figure 8) [30].
\nMolecular structures of four toxic PAs. (1) senkirkine; (2) senecionine; (3) retrorsine; (4) seneciphylline.
Indole alkaloids constitute a wide class of natural products most of them pharmacologically important and characterized by very different activities [31]. In the recent years, attention has been focused on the biological activity of yohimbine which is a monoterpenoid indole alkaloid (Figure 9). It displayed the treatment of erectile functional disturbance and anxiogenic [32]. Hydroindole alkaloids such as mesembrine and congeners (mesembrenone, Δ7 mesembrenone, mesembranol and its stereoisomer epimesembranol) have been isolated from Sceletium species used for the psychoactive effects [33].
\nMolecular structure of yohimbine and mesembrine.
The vinca alkaloids were isolated from the Madagascar periwinkle, Catharantus roseus G. Don., which included a class of about 130 terpenoid indole alkaloids [32]. In early 1965, people obviously know their clinical quality. And this group of compounds has been taken advantage of as an anticancer servant for more than 40 years and is a symbol of the compound that gives the trend to drug development [34, 35]. Among these base (+)-vincamine exhibits a valuable therapeutic activity in cerebral insufficiencies. Due to the presence of three stereogenic centers eight stereoisomers (four enantiomeric pairs) are in fact possible (Figure 10) [36].
\nMolecular structure of major vinca alkaloids isolated from Catharanthus roseus: (+)-Catharanthine (A) and (−)-Vindoline (B).
Steroidal alkaloids including verticine and verticinone are distinguished by cholestane carbon skeleton (isosteroid alkaloids) with a hexacyclic benzo [7, 8] fluoreno [2,1-b] quinolizine nucleus (Figure 11). These compounds have been isolated from plants from Liliaceae family typically Bulbus fritillariae used as a traditional medicine in Japanese, Turkish, Pakistani, and south-east Asian folk medicines [10]. Pharmacological studies demonstrate that verticine and verticinone in Bulbus Fritillariaeare the primary active ingredients responsible for the antitussive activity [37].
\nMolecular structures of verticine and verticinone.
Stemona, belonging to Stemonaceae family, is known in the folk medicine of Southeast Asia, China, and Japan since its Phyto-preparations (primary the roots) are used to treat diseases about bronchitis, pertussis and tuberculosis. Interestingly many alkaloids, structurally defined as pyrido[1,2-α]azepines, have been recognized in this plant species and are considered the important pharmacological activity. All the Stemona alkaloids are polycyclic and contain multiple stereocenters [38]. Up to now, there are about 139 Stemona alkaloids which the scientist isolated (Figure 12).
\nMolecular structure of stemonamine and parvistemoline.
Analytical methods usually contain several steps, such as sampling, sample preparation, isolation, and quantification. Remarkably sample preparation just recently is concentration as an important analytical step. According to Wen et al. [39, 40], the main objective of sample preparation are removal of interferences, and preconcentration of the analytes that is considered a bottleneck of analytical processes. In this chapter, we will provide the current state of the art in sample preparation for analyzing alkaloids in herbal matrices, focusing on extraction, clean-up steps and purification.
\nUltrasound Assisted Extraction (UAE) technique is based on the using of acoustic waves in the kilohertz range spreading in liquid medium. These waves created by the ultrasound produces regions of compression and rarefaction in the molecules. Then, the cavitation bubbles are formed and collapse giving rise to smaller bubbles that could act as new cavitation nuclei or simply get dissolved. When the bubbles collapse at the surface of the herbal material, a shockwave having very high temperature and pressure is induced, resulting in plant cell disruption which enhances both the mass transfer of alkaloids into solution and the solvent penetration [41]. In addition, the swelling of plant materials can be enhanced by ultrasound, leading to improving of solvent penetration which increases the extraction yield [42]. The UAE procedure is optimized with regard to extraction solvent, temperature and liquid to solid ratio for the plant sample [41]. UAE has some advantageous properties including high extraction efficiency, good reproducibility, low solvent consumption, low cost and environmental friendliness. However, the major disadvantage of UAE is generating heat, leading to the degradation of thermo labile products and racemization of chiral compounds [43]. To avoid such types of drawback, extraction is carried on under an ice bath to reduce the temperature [44]. Table 1 lists examples of protocols that were developed using MAE from various plants.
\nPlant | \nCompounds | \nSolvent | \nSolvent: biomass (mL: g) | \nTemp (°C) | \nTime duration (min) | \nRef. | \n
---|---|---|---|---|---|---|
Macleaya cordata | \nProtopine Allocryptopine Sanguinarine Chelerythrine Dihydrochelerythrine Dihydrosanguinarine | \n1-hexyl-3-methylimidazolium tetrafluoroborate ([C6MIM][BF4]) aqueous solution | \n500: 1 | \n80 | \n15 | \n[45] | \n
Catha edulis | \nNorephedrine Cathine Cathinone | \n0.1 N HCl | \n600: 1 | \n— | \n45 | \n[46] | \n
Ipomoea genera | \nErgot alkaloid (ergine, ergometrine, lysergic acid α-hydroxyethylamide) Penniclavine Chanoclavine Lysergol | \n70% methanol | \n100: 1 | \n60 | \n30 | \n[47] | \n
Carica papaya | \nCarpaine Pseudocarpaine Dehydrocarpaine I Dehydrocarpaine II | \n100% methanol | \n100: 7.5 | \n— | \n20 | \n[48] | \n
Extraction conditions from various plants using UAE.
The MAE technique uses the electromagnetic radiations with a frequency range of 0.3–300 GHz, that stimulates ion migration and dipole rotation leading to the heating of dielectric materials and the penetration of extraction solvent into the matrix [49]. The released thermal energy is increased gradually with higher dielectric constant, so the effectiveness of MAE is depended on the dielectric properties of both extraction solvent and sample matrix [50]. Therefore, only specific solvents which have high dipole moment as water, methanol and ethanol can be used for extraction solvent in MAE and the moisture of plant sample is an important factor in the extraction efficiency [51]. Basically, higher water content matrices will be expected to give higher extraction yields. Water contained in plant matrices absorbs microwave radiation creating pockets of localized heating in the sample. This heat promotes the plant cell walls rupture which enhances the release of alkaloids into the solvent and the increase of extraction yield [50]. In addition to having a high dielectric constant, the extraction solvents must have a high dissipation factor to reduce the potential of localized sample overheating resulting degradation of alkaloids in plants [43]. Therefore, organic solvent-water mixtures, polar organic solvents and water are usually used as extraction solvent. Moreover, other parameters relating to extraction performance as sample size, sonication power, solid to liquid ratio, extraction time and microwave power should be modified for MAE procedure optimization [34]. The main advantages of MAE are the low solvent consumption, the ability to extract many samples simultaneously and the short extraction time [43, 52]. The major drawbacks of MAE are nonhomogeneous heating distribution and overheating of extract which may cause racemization or thermal degradation of chiral alkaloids [44]. Table 2 lists examples of protocols that were developed using MAE from various plants.
\nPlant | \nCompounds | \nSolvent | \nSolvent: biomass (mL: g) | \nTem (°C) | \nTime duration | \nMicrowave power (W) | \nRef. | \n
---|---|---|---|---|---|---|---|
Peganum harmala | \nVasicine, Harmalin Harmine | \n80% ethanol | \n30: 1 | \n80 | \n8 min | \n600 | \n[53] | \n
Stephania sinica | \nSinoacutine Palmatine Isocorydine L-tetrahydropalmatine | \n65% ethanol | \n24: 1 | \n60 | \n90 s | \n150 | \n[54] | \n
Lotus plumule | \nLiensinine Dauricine Isoliensinine Neferine Nuciferine | \n65% methanol | \n— | \n— | \n4 min | \n200 | \n[55] | \n
Corydalis decumbens | \nProtopine Palmatine Allocryptopine Jatrorrhizine Tetrahydropalmatine Corypalmine Bicuculline | \n90% methanol | \n20: 1 | \n40 | \n5 min | \n— | \n[56] | \n
Menispermum dauricum | \nBianfugedine, Menisporphine, 6-O-demethylmenisporphine Bianfugecine Dauriporphine Dauriporphinoline | \n70% ethanol | \n20: 1 | \n60 | \n11 min | \n— | \n[57] | \n
Extraction conditions from various plants using MAE.
The SFE process utilizes pressurized fluids (mainly CO2) as extraction solvents. In this technique, a fluid is heated and compressed to reach above critical point of it’s creating the fluid having physicochemical properties of both liquid and gas states called supercritical fluid [58]. Specifically, supercritical fluid has a density similar to liquid (0.3–0.8 g/cm3), a viscosity similar to gas (10−4 – 10−3 g/s.cm) and a diffusion coefficient that is intermediate between liquid and gas [59]. Therefore, supercritical fluid has higher transport capacity which facilitate to fluid diffusion through plant materials in comparison to traditional extraction solvents [43]. In addition, the density is related to polarity property of fluid which directly impact in solubility of compounds in extraction solvent. This parameter can be modified by controlling temperature and/or pressure so the flexibility and selectivity of the technique is enhanced, enabling selective extraction of different compounds from the plant matrix [60]. Carbon dioxide is commonly used in SFE because it has ideal properties including low critical temperature (31.3°C) and can be easily remove from extracts [51]. However, carbon dioxide is less effective in extraction of polar compounds from matrix because of its low polarity property. Aiming to extract more polar alkaloids, the modifiers such as methanol, ethanol or water are added to extend the range of the solvating strength [43, 47]. For optimization of SFE procedure, these parameters such as pressure, temperature, modifier, flow of carbon dioxide and modifier [51]. Besides, the extraction time also effects on extraction yield, since an inadequate extraction time can result in incomplete extraction, while too long extraction time can cause the degradation of compounds. The major drawback of SFE are the complexity of system configuration and the requirement for a personal training program to operate the instrument [61].
\nPSE process uses the pressurize solvents to enhance transport capacity of solvents and mass transfer rates which leads to improve extraction performance. In this technique, extraction solvents are heated at/or above the solvent’s boiling points to decrease viscosity while keeping its in liquid state thanks to an elevated pressure [62]. Therefore, the extraction process is enhanced kinetic which leads to decreasing both the extraction time and solvent consumption. Similar to SFE, these parameters such as solvents nature, temperature and pressure should be modified to optimize PSE procedure [51]. Logically, higher temperature would be expected to give higher alkaloid extraction yields. However, excessive temperature may cause degradation and racemization of chiral alkaloids. The main advantages of PSE are utilizing an extensive range of solvents (except strong acids/bases), low solvent consumption, short extraction time, automated instruments and performing an oxygen- and light – free extraction condition. Besides, the major drawbacks of PSE are similar to SFE such as using expensive laboratory equipment and requirement for a professional training to operate instrument [43].
\nDue to the alkaloids usually exist in plants at low concentration and the complication of plant matrices, samples should be purified and enriched which facilitate to identify and/or quantify process right after extraction step. Liquid–liquid extraction (LLE) and solid phase extraction (SLE) are popular clean-up methods utilized for sample preparation of alkaloids. Moreover, other techniques based on LLE and SPE methods, such as Liquid Membrane Extraction (LME) and Solid-Phase Micro Extraction (SPME) have also been developed.
\nLiquid–Liquid Extraction (LLE) is the most simple and traditional clean-up method. LLE method is based on the relative solubility of compounds between two immiscible solvents. The alkaloids have polarity varying between pH, so the solubility of alkaloids in specific solvent are also affected by pH [34]. In the acid solutions (pH is lower than pKa of alkaloids), the analytes are protonated which leads to better water solubility so this aqueous phase can be washed with less polar organic solvents such as ethyl acetate, n-hexane and diethyl ether to eliminate hydrophobic interferences. After that, this aqueous layer is alkalinized which leads to the alkaloids becoming non-polarity and can be extracted by organic solvents to eliminate hydrophilic interferences [63]. For enrichment, the organic solvents layer can be collected, vaporized and reconstituted into new solvents which is suitable for analytical instrument. The main disadvantages of this method are requirement for repetitive extraction causing time consuming and solvent wasting [51].
\nTo overcome the drawback of LLE method, solid phase extraction (SPE) has been developed and applied in sample preparation since the 1970s. In this method, extract is loaded onto a sorbent phase which will retain alkaloids. Then, interferences in extract are washed away and the analytes is eluted by suitable solvents [64]. In fact, cartridge is the most popular SPE type due to its convenience. The SPE procedure have five step including conditioning, loading, washing and elution step. Several factors can affect to the extraction efficiency such as concentration of analytes in solvent, loading solvent nature, sorbent types, particle size, volume used for loading – washing – eluting, flow rate and elution solvent. Each factor has specified role which depends on the affinity of analytes and solid phase. Because the chemical structures of alkaloids always have secondary or tertiary amine groups, the strong cation exchange (SCX) sorbents are an ideal choice for sample preparation. When using these sorbents, washing solvent will be water and organic solvent to eliminate both hydrophilic and hydrophobic from plant matrices. After that, alkaloids will be deprotonated for elution by alkalized solvent which has pH at 2 units above pKa of analytes and evaporated to enrich sample [64].
\nIf the analytes are unstable in strong alkaline solutions, the weak cation exchange (WCX) will be use instead. The WCX sorbent has carboxylic acid as functional group which has pKa value about 4.8, so these sorbents should be conditioned by solutions having pH above 6.8 for sorbent ionization. In addition, the loading and washing solvent pH should be adjusted at the value above 6.8 and below 2 value of analytes’s pKa to maintain the ionized state of both sorbent and analytes. Finally, the alkaloids will be eluted by the acidic solutions [63]. Besides, the C18 and C8 sorbents are also applied to extract aromatic alkaloids and eliminate hydrophilic interferences from matrices. In some case, those sorbents could be used for eliminating hydrophobic interferences by loading unretained alkaloids through cartridges [64].
\nHigh performance liquid chromatography (HPLC) is currently the most widely used chromatographic enantio-separation technique [65]. HPLC has become one of the most common modern chemical analysis techniques because of its versatility, efficiency, stability, reproducibility and sensitivity. With these advantages, HPLC continues to be one of the best choices for chiral analysis and separation. Basically, chiral separation by HPLC techniques included direct and indirect methods. The indirect method is based on diastereomer formation by the derivatization reaction of analytes and a chiral reagent, then the separation of diastereomeric derivatives is performed by using a column having an achiral stationary phase. In addition, the direct method uses a chiral stationary phase for chiral separation or forms diastereomer by using a chiral mobile phase additive (CMPA).
\nHPLC using CSPs has demonstrated to be extremely useful, accurate, versatile, and it has been a widely used technique in diverse fields and applications, emphasizing (Table 3). The CSP mode is generally the most straightforward and convenient means for chromatographic enantiomer separation; it is the method of choice for both analytical and preparative applications [66, 67, 68, 69]. A hundred CSPs have been developed and commercialized thirty years ago [70]. Besides, the larger number of CSPs are made in laboratory for specialized separation. CSPs are divided into nine major types by Snyder basing on the interaction mechanism between stationary phase and analytes [71].
Macromolecular selectors of semisynthetic origin (polysaccharides)
Macromolecular selectors of synthetic origin (poly(meth)acrylamides), (poly-tartramides)
Macromolecular selectors of natural origin (proteins)
Macrocyclic oligomeric or intermediate-sized selectors (cyclodextrins, macro-cyclic antibiotics, chiral crown ethers)
Synthetic, neutral entities of low molecular weight (Pirkle-type phases, brush-type CSPs)
Synthetic, ionic entities of low molecular weight that provide for ion exchange
Chelating selectors for chiral ligand-exchange chromatography.
Type | \nCSP | \nTypical column trade name | \nApplication | \n
---|---|---|---|
I | \nPolysaccharide | \nAD, OD, OJ, AS, IA, IB, IC | \nAlkaloids, tropines, amines, beta blockers, aryl methyl esters, aryl methoxy esters | \n
II | \nSynthetic-Polymer CSPs | \nKromasil CHI-DMB and CHI-TBB | \nAcidic, neutral, and basic compounds | \n
III | \nProtein Phases | \nChiral HSA, Chiral AGP, Ultron ES-OVM, Chiral CBH | \nBenzodiazepine, Warfarin and oxazepam, beta blockers | \n
IV | \nCyclodextrin | \nCyclobond I, II, III | \nBeta blockers | \n
V | \nMacrocyclic Antibiotic | \nChirobiotic V, T, R, TAG; vancomycin | \nPolar compounds such as underivatized amino acids | \n
VI | \nChiral Crown-Ether | \nChiroSil RCA(+); SCA(−); ChiralHyun-CR-1 | \nAmino acids, amino acid esters, amino alcohols | \n
VII | \nDonor-Acceptor Phases | \nWhelk-O 1, ULMO, Sumichiral 2500, Sumichiral OA 4900 | \nAmides, epoxides, esters, ureas, carbamates, ethers, aziridines, phosphonates, aldehydes,ketones, carboxylic acids, alcohols | \n
VIII | \nChiral Ion-Exchangers | \nChiralpak QN-AX; Chiralpak QD-AX | \nChiral carboxylic, sulfonic, phosphonic, and phosphoric acids | \n
IX | \nChiral Ligand-Exchange | \nChiralpak MA+, Nucleosil Chiral-1 | \nAmino acids | \n
Application of nine major types of CSP and their commercial CSP [72].
Polysaccharide-derived CSPs are widely used in enantio-separation of a large number of chiral compounds [71]. The development of polysaccharide-derived CSPs has continued for about three decades. It can be roughly divided into two stages (i) the coated CSPs stage, and (ii) the immobilized CSPs stage.
\nPolysaccharide selectors have been used for enantioselective liquid chromatography technique for a long time. In 1973, a polymeric selector (without supporting matrix) was introduced by Hesse and Hagel named as microcrystalline cellulose triacetate (MCTA) used for enantioselective liquid chromatography. MCTA are widely applied in enantio-recognition and preparative separations due to its ideal loading capacities. However, this material has major disadvantages including poor pressure stability, slow separations, and low chromatographic efficiency. To overcome the mechanical stability problem of MCTA, a solution was found by Okamoto and co-workers in 1984, in which the surface of macro-porous silica beads (100 or 400 nm pore size) was coated by the cellulose derivatives at about 20 wt%. Thanks to this coating, the mechanical stability of this material was remarkably improved resulting in better efficiencies qualified for HPLC enantiomer separations. Such coated polysaccharide-based CSPs were the highest level of polymeric selector developments for several decades [71].
\nNowadays, about 200 kinds of polysaccharide derivatives were introduced by using different polysaccharides which includes cellulose, amylose, chitin, chitosan, galactosamine, curdlan, dextran, xylan, and inulin [72] (Figure 13). These materials have been coated on a surface of macro-porous silica gel to create CSPs and followed by the evaluation of chiral recognitions on HPLC.
\nStructures of the various kinds of polysaccharides: (1) cellulose; (2) amylose; (3) chitin; (4) chitosan; (5) Galatosamine; (6) Curdlan; (7) dextran; (8) Xylan; (9) inulin.
Each of coated polysaccharide-based CSPs exhibit the different enantioselectivity and elution order of the various enantiomers due to the structural differences of CSPs including sugar units, linkage position, and linkage type. In particular, the derivatives of cellulose and amylose usually perform higher recognition abilities than the others, though this property also depends on the structure of a specific racemate. The most useful and successful derivatives of cellulose and amylose are triesters and tricarbamate. It has been claimed by Aboul-Enein and Ali that for the resolution of about 500 test racemates, about 80% of them have been successfully resolved on only two kinds of polysaccharide derivative-based CSPs (cellulose and amylose tris (3,5-diphenylcarbamate) CSPs) [72]. More specifically, three famous commercially available CSPs, CHIRALCEL OD, OJ, and CHIRALPAK AD, have fully or partially resolved 70% racemates among over 100 racemates tested [71].
\nA current strategy introduced by Snyder for chiral separation method development includes trial-and-error experiments of various polysaccharide-type CSPs under multiple respective mobile-phase conditions using fully automated column- and solvent-switching. Nowadays, more and more studies have focused on developing a more efficient screening procedure to enhance the chance for success and shorten the experiment time: the most favorable CSP in the normal phase mode is
\n\n\n
The separation efficiency of column should be tested before conducting screening experiment if serial instead of parallel screening is utilized. The application of coated polysaccharide-derived CSPs has been reviewed in Table 4 including the names of CSPs and their most frequent applications.
\nThe coated CSPs are formed by coating the polysaccharide derivatives onto surface of silica gel. Due to the weak linkages and interactions between the polysaccharide derivatives (chiral selector) and silicagel (substrate), a number of organic solvents including chloroform, dichloromethane, tetrahydrofuran and ethyl acetate which can dissolve or swell the chiral selector are not allowed using as mobile phase components. Besides, the mixtures of alkanes (n-pentane, n-hexane or n-heptane) and alcohols (2-propanol (IPA), ethanol or methanol (n-pentane, n-hexane or n-heptane)) and alcohols (2-propanol (IPA), ethanol or methanol) are favorable mobile phase solvents used in normal phase mode. The addition of “prohibited solvents” may lead to better separation and greater solubility of racemic analytes than the standard solvent combinations so the performance of separation method is improved. Besides, the better solubility of racemic analytes also facilitates preparative separations. In addition, the spectroscopic techniques used for chiral recognition should ideally be in the “prohibited solvents”. As a result, chemical immobilization of polysaccharide derivatives becomes an interesting research topic to overcome the drawbacks of the coated CSPs (see in Figure 14). In 2005, Daicel and Chiral Technologies introduced a set of three immobilized polysaccharide CSPs as [71]:
Chiralpak®IA (immobilized version of Chiralpak AD)
Chiralpak®IB (immobilized Chiralcel OD) [61]
Chiralpak®IC based on the cellulose tris (3,5-dichlorophenylcarbamate) selector that is not available in coated form.
Effect of column type (immobilized vs. coated polysaccharide-based CSP) and mobile phase on enantioselectivity. Enantiomer separations of N-benzyloxycarbonyl-phenylalanine (a–c) with Chiralpak IB (immobilized) and Chiralcel OD (coated). Flowrate: 1 mL/min; temperature: 25°C; UV detection at 230 nm. Note that the mobile phases used in (a) is forbidden mobile phases for the coated version Chiralcel OD [71].
Finally, it should be noted that polysaccharide CSPs have now also been established as the first-choice of chiral phases for enantiomer separation.
\nAnalytical applications, including CSPs, separation conditions and analyte, are summarized in Table 5. A review focused mainly on the latest examples of chiral alkaloids separations on CSPs for efficient analyses was prepared.
\n\nTrade name | \nChemical name | \nApplications | \n
---|---|---|
Cellulose CSPs | \n||
Chiralcel OB | \nCellulose trisbenzoate | \nSmall aliphatic and aromatic compounds | \n
Chiralcel OJ | \nCellulose tris(4-methyl benzoate) | \nAryl methyl esters, aryl methoxy esters | \n
Chiralcel OC | \nCellulose trisphenylcarbamate | \nCyclopentanones | \n
Chiralcel OD | \nCellulose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, amines, \n | \n
Chiralcel OD-H\nb\n\n | \nCellulose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, amines, \n | \n
Chiralcel OD-R\nc\n\n | \nCellulose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, amines, \n | \n
Chiralcel OD-RH\nd\n\n | \nCellulose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, amines, \n | \n
Chiralcel OF | \nCellulose tris(4-chlorophenylcarbamate) | \n\n\n | \n
Chiralcel OG | \nCellulose tris(4-methylphenylcarbamate) | \n\n\n | \n
Chiralcel OA | \nCellulose triacetate on silica gel | \nSmall aliphatie compounds | \n
Amylose CSPs | \n||
Chiralpak AD | \nAmylose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, tropines, amines, \n | \n
Chiralpak AD-R\na\n\n | \nAmylose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, tropines, amines, \n | \n
Chiralpak AD-RH\nb\n\n | \nAmylose tris(3,5-dimethylphenylcarbamate) | \nAlkaloids, tropines, amines, \n | \n
Chiralpak AD-H | \nAmylose tris-(3,5-dimethylphenylcarbamate) | \nAlkaloids | \n
Chiralpak AR | \nAmylose tris(R)-1-phenylethylcarbamate | \nAlkaloids, tropines, amines | \n
Chiralpak AS | \nAmylose tris(S)-1-methylphenylcarbamate | \nAlkaloids, tropines, amines | \n
Columns supplied by Daicel Chemical Industries, Tokyo, Japan, Dimension are column size 25 cm X 0,46 cm, particle size 10\n
Column size 25 cm X 0,46 cm, particle size 5\n
Column size 15 cm X 0,46 cm, particle size 10\n
Column size 15 cm X 46 cm, particle size 5\n
Columns | \nAnalyte | \nPlant | \nSeparation conditions | \nRef. | \n
---|---|---|---|---|
CHIRALPAK AS-H column | \n(12S,22S)-Dihydroxyisoechinulin A (2) and (12R/S)- Neoechinulin A | \nCannabis sativ L | \nHexane/isopropanol/diethylamine (4:1:0.05) | \n[73] | \n
CHIRALPAK AD-H column | \nMucroniferanine A | \nCorydalis mucronifera | \nn-hexane−2-propanol (70:30) | \n[74] | \n
(±)-homocrepidine A | \nDendrobium crepidatum | \nn-hexane/2-propanol (95:5) | \n[75] | \n|
(+)-(3R,6R)- and (−)-(3S,6S)-3α,6β-tropanediol | \nErythroxylaceae species | \nn-hexane and 2-propanol (9:1) with 0.1% of diethylamine | \n[76] | \n|
Chirobiotic V, Chiralpak-AY3 column | \n(−) and (+) hyoscyamine | \nSolanaceaes seeds | \nEthanol, 0.1% DEA | \n[77] | \n
Chirex 3019 chiral column | \nS-(−)-canadine and R-(+)-canadine | \n\nHydrastis Canadensis L. | \nHexan:DCE:EtOH:TFA (75:40:7:0.1) | \n[78] | \n
CHIRALPAK AGP column | \n(R)-nicotine; (S)-nicotine; anabasine, and anatabine | \nTobacco | \nNH4OH- methanol (90:10) | \n[79] | \n
A Phenomenex Lux Cellulose-2 chiral column | \n(+)- and (−)-5-hydroxyl-8-oxyberberine | \nCoptis chinensis | \nCH3CN:H2O (40:60) | \n[80] | \n
Chiralpak IA column | \nintermedine and lycopsamine | \nSymphytum uplandicum | \nACN/methanol (80:20) and methanol/methyl-t-butyl ether (90:10) | \n[81] | \n
Phenomenex-Chirex-3126 column | \ndihydrocarneamide A and iso-notoamide B | \nPaecilomyces variotii | \nMeCN–H2O (5:95). | \n[82] | \n
Summary of CSPs, mobile phase compositions, and applications.
Novel column materials also improved enantiomer separation of tropane alkaloids. Separation of (R, S)-hyoscyamine was achieved using chiral stationary phase with immobilizing α-1-acid glycoprotein (Chiral AGP®) [83], alternatively, enantiomer separation of atropine could be achieved by a chirobiotic V column packed with vancomycin as chiral selector [84]. Anisodamine, the 6β-hydroxyl derivative of (S)-hyoscyamine was separated from its synthetic enantiomer and diastereomers by a Chiralpak AD-H column as chiral stationary phase, which uses an amylose derivative as chiral selector [85]. Satropane, 3α-paramethylbenzenesulfonyloxy-6β-acetoxy-tropane, could be resolved in 3S, 6S-isomer named lesatropane and 3R, 6R-isomer named desatropane. Lesatropane as a novel muscarinic agonist is being under preclinical development in China as a single enantiomer drug for the treatment of primary glaucoma. The separation of lesatropane from desatropane was conducted by both Chiralpak AD-H and Chiralpak AS-RH column [86].
\nChiral separation of isoquinoline alkaloid has also achieved by using chiral stationary phase. For example, the determination of tetrahydropalmatine (THP) was performed by using a Chiralcel OJ column with quantification by UV at 230 nm. This developed method was used for determining the pharmacokinetics of THP enantiomers in rats and dogs after oral administration [87]. Another report of isoquinoline alkaloid group is sanguinarine derivatives. Chiral determination of Benzophenanthridine alkaloids from methanol extracts of Hylomecon species was conducted by Chiralcel OD (4.6 x 250 mm) column with mixture of isopropanol-hexane-diethylamine (20/80/0.1, v/v/v) as a mobile phase [88]. The stereochemistry of L-isocorypalmine and the D/L ratio of tetrahydropalmatine, stylopine, and corydaline were established unambiguously by using a chiral Chiralcel OD (4.6 x 250 mm) column; 50% ethanol as mobile phase; wavelength 230 nm [89]. Cularinoids are a group of isoquinoline alkaloids consisting of about 60 members. The HPLC enantiomeric separation of the racemic cularinoid alkaloids N-p-methoxy-1,α-dihydroaristoyagonine and 4′,5’demethoxy-1,α-dihydroaristoyagonine was accomplished using five chiral stationary phases (CSPs), the good enantioselectivity and resolution factor obtained with a polysaccharide-derived CSP (Chiralpak AD) [90].
\nIndole derivatives are widely used in chiral synthesis, chemical asymmetric catalysis, biological and medicinal chemistry. Recently, the enantiomeric separation of several chiral plant growth regulators and related compounds, such as 3-(3-indolyl)-butyric acid, abscisic acid and structurally related molecules including a variety of substituted tryptophan compounds was reported. Chiral stationary phases such as coated and immobilized were suitable for the separation of indole derivatives; however, the coated CSP possesses a higher resolving power than the immobilized one [91]. Tangutorine, a biogenetically interesting indole alkaloid, was found in the leaves of Nitraria tangutorum in 1999. It was separated from its synthetic enantiomer by chiral stationary phases two polysaccharide-derived CSP (Chiralcel OD and Chiralpak AD) and a network polymer incorporating a bifunctional C2-symmetric chiral selector (Kromasil CHI-DMB) [92]. The HPLC enantiomeric separation of racemic indole alkaloids tacamonine, 17α-hydroxytacamonine, deethyleburnamonine, and vindeburnol was accomplished using Chiralpak AD and Chiralcel OD as chiral stationary phases [93].
\nThe enantiomers of homocamptothecin (hCPT) derivatives which constitute a promising series of potent anticancer agents targeting DNA topoisomerase I were separated by using the combination of two silica-based normal phase column including Chiralcel OD-H (celluloses tris-3,5-dimethylphenylcarbamateand) Chiralcel OJ (celluloses tris-methylbenzoate) or Chiralpak AD (amyloses tris-3,5-dimethylphenylcarbamate) and Chiralpak AS (amyloses tris-(S)-1-phenylethylcar-bamate) [94]. A method for the simultaneous determination of eight Cinchona alkaloids (quinine, quinidine, cinchonine, cinchonidine, and their corresponding dihydro analogs) using a novel strong cation-exchange-type chiral stationary phase (cSCX) column in HPLC has been developed and exemplarily applied to impurity profiling of a commercial alkaloid sample [95].
\nMost of alkaloids are chiral compounds and are clinically administered as the racemic mixture, although its enantiomers have been shown to exert different pharmacological activity. The complication of sample matrices and low concentration of chiral alkaloids are major challenges for analytical processes. To improve the performance of analytical procedure, we provide the current state of the art in sample preparation focusing on extraction and purification to remove interferences and enrich analyte concentrations. HPLC using CSPs has demonstrated to be extremely useful, accurate, versatile, its mode is generally the most straightforward and convenient means for chromatographic enantiomer separation. The development of CSPs for HPLC is a continuous and challenger issue covering various types of CSPs.
\nThe authors would like to express their hearty gratitude to Can Tho University of Medicine and Pharmacy. We also thank all of our colleagues for their excellent assistance.
\nThe authors declare no conflict of interest.
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\n\nOver the years we have learned what is important. What makes a difference to the researchers that work with us, what they value. Something that is very high not only on their lists, but our own, is the quality of the published content.
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