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Antioxidant Activity of Lignin -Mannich Bases Synthesised by Amination Reactions

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Antioxidant Activity of Lignin -Mannich Bases Synthesised by Amination Reactions J. Chem Soc. Nigeria, Vol. 44, No. 7, pp 1276 -1282 [2019] Antioxidant activity of Lignin -Mannich bases Synthesised by Amination reactions G. K. Oloyede,1*, B.O. Ogunsile 2, M.S.Ali 3, and W.A. Ngouonpe 4 1Organic Chemistry Unit, Department of Chemistry, University of Ibadan, Nigeria. 2 Industrial Chemistry Unit, Department of Chemistry, University of Ibadan, Nigeria. 3HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi. 4Department of Chemistry, Higher Teacher Training College, University of Yaounde 1, P.O.Box 47, Yaounde, Cameroon *Correspondents Author’s E-mail: [email protected] Tel: +234 803 562 2238 Received 17 June 2019; accepted 27 September 2019, published online 29 November 2019 ABSTRACT Lignin is a polymer derived from the phenylpropanoid compounds, coniferyl alcohol and related alcohols. It is the second abundant (next to cellulose) and important organic substance in the plant world. Researches on lignin has been in the area of adsorption properties, but this present study is aimed at synthesizing Mannich bases by amination reaction and investigating the antioxidant activities. Lignin was extracted from Nypa fruticans Wurmb. by soda pulping method. The lignin was subjected to Mannich reaction. The Lignin Mannich Bases (LMB) prepared were screened for antioxidant activity using 2,2- diphenylpicryl hydrazyl radical (DPPH) method. Results obtained showed that the Mannich bases prepared had the following monolignol units: methylamine (LMB1), dimethylamine (LMB2), diethylamine (LMB3), aniline (LMB4), 2,6—dimethylaniline (LMB5), 3,4-dimethylaniline (LMB6), 2,5-dimethylaniline (LMB7), 3,4-dichloroaniline (LMB8), 2,6-dichloroaniline (LMB9), and 2- (3,4-dimethoxyphenyl) ethylamine (LMB10), respectively as evidenced in the Proton NMR data. Antioxidant activity showed that all the Lignin Mannich Bases had better activity than lignin and of comparable activity with standard Butylated hydroxyl anisole (BHA) with 75.64% inhibition at 1.0 mg/mL However, LMB4 (74.31%), LMB6 (72.98%), LMB7 (71.46%) and LMB3 (71.03%) which showed significant activity at this concentration. This present study has therefore been able to synthesize new Mannich bases from Lignin, a renewable natural resources and establish the potential of lignin and its amination products as antioxidants. Keywords: Nypa fruticans, lignin; amines; antioxidant; butylated hydroxyl anisole INTRODUCTION Lignin is an amorphous, polyphenolic material supportive agent (mechanical strength), having aldehyde, keto, hydroxyl, methoxy and antioxidant (protection), sealant and reinforcing phenolic groups. It is formed from an enzyme- agents (bonding cellulose and hemicellulose mediated dehydrogenation polymerization of together) and as a cross linker (cross link three phenylpropanoid monomers, conniferyl, carbohydrates). Many researches on lignin has synapyl and p-coumaryl alcohols. Lignin is the been in the area of adsorption especially on second most abundant component next to metallic ions because lignin is inexpensive, cellulose in biomass. It serves as a binding agent renewable, available, have aromatic and cross for cellulose and semi cellulose. It is produced linked structure and contain various worldwide from paper and pulp but only functionalized groups that can adsorp metallic approximately 2% of the total lignin is used as ions. Lignin is also used as a replacement for of dispersant or binding agents and the remainder is phenol in phenol – formaldehyde adhesives or burned as low value fuels. Lignin is used as resins. The amination of industrial soft wood J. Chem Soc. Nigeria, Vol. 44, No. 7, pp 1276 -1282 [2019] kraft lignin was conducted using Mannich exploited as a raw material for chemical reaction to modify the lignin structure for value production, but chemical modification of lignin added application [1-3]. Phenolation, reduction, in the last decade has driven numerous efforts demethylation and hydrolysis are also important and researches with significant studies [3, 9]. modifications. The modified lignin is highly The growing interest about green and hydrophilic and has high molecular mass sustainable chemistry has also contributed to rendering it useful for many potential attention on biomass. The aim of this present applications as slow release fertilizer, reagent for study therefore was to use Mannich reaction in enzyme immobilization and polycationic the structural modification of soft wood lignin materials.Amination of lignin was achieved by obtained from Nypa friticans, characterize the Mannich reaction. Mannich reaction is important Mannich bases using proton nuclear magnetic in the synthesis of beta – amino ketones or esters resonance and investigate the antioxidant that are useful in the preparation of many activity of the Lignin Mannich Bases (LMB) important biologically important nitrogen- formed . Nypa frutican Wurmb. (Arecaceae) is containing compounds. Previous researches on a softwood, evergreen plant with erect leaves use of Mannich reaction on lignin produce planted along swampy coastlines, often with cationic asphalt emulsifiers, cationic surfactants mangroves. It has edible seeds and sap. The and anion exchange resins [2, 4]. Mannich sugary sap is obtained from the inflorescence to reaction is an amino alkylation of an acidic make alcoholic beverage, syrup and vinegar. It is proton placed next to a carbonyl functional used traditionally in the treatment of herpes, group by formaldehyde and a primary or ulcer, toothache and headache. The leaves are secondary amine or ammonia. The final product used in thatching and basket making [10-11]. is a β-amino-carbonyl compound also known as Mannich base [5-6]. Structural activity MATERIALS AND METHOD relationship has shown that many Mannich bases Chemicals and Reagents are biologically active especially as anti- cancer, The following BDH chemicals and reagents: anticonvulsant, anti-HIV, anti - Parkinson, Formaldehyde, chloroform, ethyl acetate, n- antitumor, antioxidant, antimicrobial, hexane, methanol, hydrochloric acid, ammonia immunological response modifier, analgesic, solution, conc. tetraoxosulphate (VI) acid, amongst others [7-8]. Notably, only 2% of ammonia solution, methylamine, Lignin produced as waste from pulp and paper dimethylamine, diethylamine, industry has been commercialized for the triethylamine, N,N-dimethyallylamine, aniline, formation of dispersants, adhesives and 2,6-dimethylaniline, 3,4-dimethylaniline, 2,5- surfactants or as antioxidant in plastics and dimethylaniline, 3,4-dichloroaniline, 2,6- rubbers [9]. It is therefore expedient to carry dichloroaniline, 2-(3,4- more research on this renewable resource. dimethoxyphenyl)ethylamine, were used. Also Lignin composition and contents are influenced 2, 2 - diphenyl-1-picrylhydrazyl (DPPH), by species and environment. Lignin precursors ascorbic acid and butylatedhydroxylanisole are generated from D-glucose through reaction (BHA) were obtained from Sigma Chemical Co of enzyme. Gymnosperms contains coniferyl (St Louis, MO). alcohol (guaiacyl unit), angiosperms contains coniferyl alcohol and sinapyl alcohol (guaiacyl General experimental procedures unit and syringyl unit) while grasses contain p- Analytical balance (KERN ALS 220-4 KERN & coumaryl alcohol (p-hydroxyphenyl unit). SOHN, Germany) was used for all weighing. Harwood lignin consists principally of guaiacyl Typical reflux set up (condenser and a Heidolph from coniferyl alcohol, and syringyl from MR3004 Heater with magnetic stirrer) was used. sinapyl alcohol and rarely p-hydroxyphenyl All reactions were monitored with Thin layer from coumaryl alcohol. On the other hand, chromatograpy (TLC) at room temperature. softwood lignin mostly comprises of guaiacyl Analysis of synthesized compounds (0.2 mg of from coniferyl alcohol, with low level of p- sample in 5 mL methanol) was carried out using hydroxyphenyl. Lignin is rarely used or J. Chem Soc. Nigeria, Vol. 44, No. 7, pp 1276 -1282 [2019] Precoated TLC Aluminium sheets Silica gel 60 General Procedure for preparation of Lignin F254 (20 cm × 20 cm, 0.2 mm thick; Merck, –Mannich Bases Germany). Proton Nuclear Magnetic Resonance (NMR) 1H was recorded on AVANCE AV-400 The preparation of the Lignin - Mannich bases spectrometer operating at 400 MHz for 1H, LMB1-LMB10, had as starting materials lignin respectively. The chemical shift values (δ) are (L) and the following amines; methylamine reported in ppm [6]. (LMB1) dimethylamine (LMB2), diethylamine (LMB3), aniline (LMB4), 2,6-dimethylaniline Preparation of Lignin - Mannich Bases (LMB5), 3,4-dimethylaniline(LMB6), 2,5- dimethylaniline (LMB7), 3,4-dichloroaniline Extraction of Lignin from Nypa fruticans (LMB8), 2,6-dichloroaniline (LMB9), 2-(3,4- dimethoxyphenyl)ethylamine (LMB10), Nypa fruticans, commonly known as nipa respectively. The preparation was based on palm or mangrove palm, is a softwood procedure used for the synthesis of Mannich species of palm native to the coastlines. Nypa bases previously described in literature but with fruticans were collected and chopped into little modification [3, 6, 13]. 0.0257 g (0.2 pieces, blended and extracted with dioxane. The mmol) Lignin and 2% HCl (0.4 mL) in EtOH extract was blead and extracted with NaOH (16 mL) (ethanolysis) was heated under reflux (caustic soda). The black liquor obtained was for 4hrs at 1200C, cooled and 36% precipitated with acid. The precipitate was formaldehyde (2.2 mmol, 3 mL) was added, removed and washed with water. Bleading 0 stirred under
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