CHAPTER 9: Preliminary phytochemical analysis of aqueous-ethanol extract of G. lucidum, protein bound polysaccharides and total triterpenes

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1 CHAPTER 9: Preliminary phytochemical analysis of aqueous-ethanol extract of G. lucidum, protein bound polysaccharides and total triterpenes

2 TABLE OF CONTENTS 9.1. INTRODUCTION 9.2. MATERIALS AND METHODS Preparation of the extract Phytochemical evaluation of the aqueous ethanol extract Preliminary phytochemical screening Test for carbohydrates/ Glycosides: (Molisch s test) Test for Saponins: Test for Alkaloids: Dragendroff's test: Wagners' test: Mayer's test: Test for Steroids/Terpenoids (Liberman- Burchard test): Test for Flavnoids (Shinoda s test) Test for Phenolics Test for Coumarins Estimation of total carbohydrate in the extract by Anthrone method Estimation of total carbohydrate in the extract by phenol-sulphuric acid method Estimation of protein in the extract by Lowry s Method Isolation of total triterpenes from by G. lucidum column chromatography Confirmation of tritepenes by the thin layer chromatography (TLC) Preparation of Spray Reagent (Anisaldehyde-H 2 SO 4 reagent) HPTLC Analysis of the extract and total triterpes Isolation of protein bound polysaccharides Confirmation of polysaccharide-protein complex nature

3 HPLC analysis of the protein bound polysaccharide Determination of monosaccharide constituents by paper and thin layer Detection of amino acids by thin layer chromatography 9.3. RESULTS 9.4. DISCUSSION

4 9.1.INTRODUCTION Higher fungi have been used by mankind for millennia. Firstly they are used as part of regular diet for their nutritional value, completing population food intake. They contain minerals, vitamins and nutritive compounds such as proteins and protein bound polysaccharides and have low fat content (Mattila et al., 2000). The fungi of the genus Ganoderma are popular medicinal mushrooms, and they have been used widely in China, Japan and Korea over the past two millennia (Sliva, 2004). Ganoderma lucidum is one of the important medicinal mushrooms which had the maximum number of research publications on the cultivation, chemical analysis, pharmacology, and medicinal effects (Stamets and Yao, 2002). The major chemical constituents of G. lucidum, such as protein bound polysaccharides, triterpenes, sterols, lectins and some proteins, have beneficial properties for the prevention and treatment of a variety of ailments including very important diseases such as, hypertension, diabetes, hepatitis, cancers and AIDS (Paterson, 2006). Since the biological activities were directly related to the bioactive constituents, investigations were carried out to examine the major constituents of the aqueous-ethanol extract of G. lucidum and the major chemical constituents of G. lucidum such as protein bound polysaccharides and total triterpenes have been analyzed by phytochemical methods. These findings are presented in this chapter. 9.2.MATERIALS AND METHODS Preparation of the extract Aqueous-ethanol (70%) extract of G. lucidum was prepared as described in section Phytochemical evaluation of the aqueous ethanol extract Preliminary phytochemical screening The aqueous ethanol extract of G. lucidum was analysed for the presence of secondary metabolites by standard methods (Harborne, 1973; Wagner et al., 1984; Daniel, 1991) as follows, 164

5 Test for carbohydrates/ Glycosides: (Molisch s test) 5 mg of extract was mixed with 0.5 ml of distilled water and add 2 drops of 10 % α- naphthol in ethanol was added to it. To this mixture 1 ml of concentrated H 2 SO 4 was added slowly through the sides of the test tube so that it forms a ring at the middle of the two solutions. The formation of a reddish violet ring indicates the presence of carbohydrate/ glycosides Test for Saponins: A little of the extract was shaken thoroughly with distilled water and the formation of froth in the test tube, which persists for a few min, shows the presence of saponins Test for Alkaloids: Dragendroff's test: The Dragendroff's reagent was prepared by mixing solution A (containing 0.6 g of bismuth subnitrate in 2 ml of concentrated HCl and 10 ml of distilled water), solution B (containing 6 g of KI in 10 ml of water) together with 7 ml of concentrated HCl and 15 ml distilled water and the whole solution was diluted with distilled water to 100 ml to form Dragendroff's reagent. Many alkaloids give a brown precipitate with Dragendroff's reagent Wagners' test: 1.72 g of Iodine and 2 g of KI were dissolved in 5 ml of distilled water and the solution was made up to 100 ml with distilled water to form Wagner's reagent. Many alkaloids give a brown flocculent precipitate with Wagner's reagent Mayer's test: The Mayer's reagent was prepared by mixing solution A (1.36 g of HgCl 2 in 60 ml of distilled water) and solution B (5 g of KI in 10 ml of distilled water) and then the mixture was made up to 100 ml with distilled water. Since this reagent reacts only with salts of alkaloids, the alkaloidal solution should be made distinctly acidic with HCl or H 2 SO 4 before adding the reagent. The reagent was added drop wise. A white precipitate indicates the presence of alkaloids. 165

6 Test for Steroids/Terpenoids (Liberman- Burchard test): The extract was dissolved in CHCl 3, to this adds 1 ml of acetic anhydride and mixed well. 1 ml of concentrated H 2 SO 4 was added through the sides of the tube. A green colour indicates the presence of steroids and pink colour indicates the presence of terpenoids Test for Flavnoids (Shinoda s test) Extract was dissolved in methanol and magnesium turnings or ribbons were added followed by concentrated HCl drop by drop. Pink colour indicates the presence of Flavonoids Test for Phenolics 10% alcoholic solution of ferric chloride was prepared. The extract was mixed with this solution and the formation of a brownish pink colour formation with alcoholic ferric chloride is a diagnostic test for phenols Test for Coumarins Extract was dissolved in methanol and alcoholic NaOH is added. A yellow colour appears which later disappears on adding drops of concentrated HCl indicate the presence of coumarins Estimation of total carbohydrate in the extract by Anthrone method Principle:- Carbohydrates are first hydrolysed into simple sugars using dilute hydrochloric acid. In hot acidic medium, glucose is dehydrated to hydroxymethyl furfural. This compound forms a green coloured product with anthrone (absorption maximum at 630 nm). Procedure: 100 mg of the sample is hydrolysed by 5 ml of 2.5 N HCl in a boiling water bath for 3 hrs. It was neutralized with solid sodium carbonate until the effervescence ceases, made up to 100 ml and centrifuged. Collected 0.5 and 1 ml of the supernatant and was used for the analysis. The standards are prepared by selecting 0.2, 0.4, 0.6, 0.8 and 1 ml of working glucose standard. Volume in each tube (including the sample tube) is made up to 1 ml with distilled water. Four ml of anthrone reagent (Anthrone 166

7 reagent: Dissolve 200 mg anthrone in 100 ml of ice-cold 95% H2SO4. Prepare fresh before use) added to all the tubes and heated for eight min in boiling water bath. Read the green to dark colour at 630 nm graph. The amount of carbohydrate in the sample was calculated from the calibration Estimation of total carbohydrate in the extract by phenol-sulphuric acid method Quantitative examination of carbohydrate was carried out according to Dubois et al (1956) method using glucose as standard Principle In hot acidic medium glucose is dehydrated to hydroxymethyl furfural. This forms a coloured complex with phenol and has absorption maxium at 490 nm. Procedure: 0.1 and 0.2 ml of the test solution having unknown concentration was made up to 1 ml with distilled water and added 1 ml of 5% phenolic solution. Then 5 ml of 97% H 2 SO 4 was added through the side of the tubes without disturbing the tubes and mixed well. After 10 min, the contents in the test tubes were kept in boiling water bath for 10 min and the O.D was noted at 490 nm. The concentration of carbohydrate in the test solution was calculated from the standard graph Estimation of protein in the extract by Lowry s Method Principle:- The blue colour developed by the reduction of the phosphomolybdic phosphotungstic components in the Folin-Ciocalteau reagent by the aminoacids tyrosine and tryptophan present in the protein plus the colours developed by the biuret reaction of the protein with the alkaline cupric tartarate were measured at 660 nm (Lowry et al., 1951). Procedure:-0.1ml of the sample was taken in to the test tube and was made up to a volume of 1 ml with distilled water. Then 5 ml of alkaline copper sulphate solution was added to each tube. Mixed well and allowed to stand for 10 min. Then added 0.5 ml of Folin-Ciocalteau reagent (1:1 diluted with water) and incubated at room temperature in the dark for 30 min. The blue color developed was read at 660 nm. A 167

8 standard graph was plotted with BSA and calculated the amount of protein in the sample Isolation of total triterpenes from by G. lucidum column chromatography The total triterpenes from the G. lucidum was isolated and purified from the ethanol extract of the fruiting bodies of G. lucidum as described in the section Confirmation of tritepenes by the thin layer chromatography (TLC) Principle: Partition chromatography is the distribution of the solute between two liquid phases, which is based primarily on the solubility differences. The position of each component of a mixture is determined by calculating the distance travelled by the component relative to the distance travelled by the solvent, relative mobility (Rf value). The Rf value for a substance is constant for a certain set of experimental conditions Preparation of Spray Reagent (Anisaldehyde-H 2 SO 4 reagent) The Anisaldehyde-H 2 SO 4 reagent is prepared by mixing 0.5 ml of p-anisaldehyde, 10 ml of glacial acetic acid, 85 ml of ethanol and 5 ml of 97% sulfuric acid. Spraying with this reagent shows pink colour for terpenes and related compounds on a TLC (Wagner et al., 1984). TLC of the extract and total triterpens fraction were performed on a pre-coated silica gel plate purchased from Merk India Ltd using solvent system n- hexane: chloroform (1:1). The developed plates were evaluated under UV (254 nm) and sprayed with anisaldehyde- H 2 SO 4 reagent, heated for the development of the spots HPTLC Analysis of the extract and total triterpes Ten mg of the extract was dissolved in 10 ml aqueous methanol and 10 mg of total triteprens was dissolved in CHCl 3 and used for analysis. The samples (5 μl) were applied as bands using microsyringe on precoated silica gel 60 F254 plates (E. Merck). The plates after sample application were developed in twin trough chambers. CHCl 3 methanol-water (30: 4: 1) was used as solvent system for the extract and 100% CHCl 3 was used as the solvent system for the total triterpenes. The plates were air dried after development and scanned under UV (254 nm) or sprayed with vanillin 168

9 sulphuric acid reagent and then scanned. Camag TLC scanner was used for scanning. HPTLC profile was obtained with Desaga Video Documentation Unit Isolation of protein bound polysaccharides The protein bound polysaccharides from the fruiting bodies of G. lucidum was isolated and purified as described in the section Confirmation of polysaccharide-protein complex nature The polysaccharide isolated from G. lucidum was analyzed for the quantification of carbohydrate content with Anthrone reagent (Yemen and Wills, 1954) and then by Phenol sulphuric acid reagent (Dubois et al, 1956) for confirmation by the methods described in the sections and The protein content present in the polysaccharide isolated from G. lucidum was estimated by the method of Lowry s method as described in the section HPLC analysis of the protein bound polysaccharide The HPLC pattern of isolated protein bound polysaccharide was done using Waters HPLC system equipped with Waters 600 series pump and Waters spherisorb amino column with mobile phase as acetonitrile/water-80/20 and a refractive index detector (Waters 2141 RI detector) at a flow rate of 1.0 ml/min. D-glucose, D-fructose, D- galactose, D-mannose, D-xylose were used as standards Determination of monosaccharide constituents by paper and thin layer chromatography Principle: The principle is same as discussed in Procedure: In order to quantify the monosaccharide profile, 1 mg of crude polysaccharide was hydrolysed by 2M trifluro acetic acid (TFA). The residue obtained after hydrolysis was dissolved in 10 % isopropanol and analysed by paper chromatography using Whatman No 1filter paper and also by thin layer chromatography using precoated silica gel plates. The chromatograms were developed with a solvent system made up of n-butanol; acetic acid; water (2:1:1). After developing, the chromatograms were dried in air and sprayed with the aniline diphenylamine phosphoric acid reagent (2 ml aniline, 2 g diphenylamine and 10 ml of 85% phosphoric acid in 100 ml of acetone). 169

10 The chromatograms were then heated at 85 C for 10 min and developed spots were compared with that of standards. D-glucose, D-fructose, D-galactose, D-mannose, D- xylose were used as standards Detection of amino acids by thin layer chromatography Principle: The principle is same as discussed in Procedure: In order to quantify the amino acid profile, 1 mg of crude polysaccharide was hydrolysed with 2M trifluro acetic acid (TFA). The residue obtained after hydrolysis was dissolved in 10 % isopropanol and analysed by thin layer chromatography using precoated silica gel plates. The chromatograms were developed with a solvent system made up of n-butanol; acetic acid; water (12:3:5). After development, the chromatograms were dried in air and sprayed with the 0.25 % ninhydrin reagent in acetone. The chromatograms were then heated at 85 C for 10 min and developed spots were compared with that of standards. Aspartic acid, glutamic acid, glycine, alanine, histidine, serine, threonine and valine were used as standards. 9.3.RESULTS Phytochemical screening of the aqueous ethanol extract of G. lucidum showed the presence of protein bound polysaccharides, triterpenes and protein in the extract (Table 9.1). The Leibermann-Burchard test showed the presence of triterpenes in the extract as characteristic pink colour in test tube and in TLC. Phenolics, coumarins, flavanoids, alkaloids and saponins are found to be absent in the extract. TLC analysis of the aqueous-ethanol extract of G. lucidum showed many spots under UV and when sprayed with anisaldehyde-sulphuric acid reagent, there were many typical pink coloured spots of terpenes. HPTLC analysis also showed blue coloured band under UV and with vanillin sulphuric acid reagent in the aqueous-ethanol extract. However the HPTLC analysis revealed that the extract contains a large number of minor components (Fig 9.1.A, Fig.9.1.B and Fig.9.1.C.). Fig 10.3, 10.4 and 10.5 shows the HPTLC developed plate at 254 nm, developed plate at 366 nm and derivatised plate at 580 nm respectively of the extract with solvent system Chloroform-methanol-water (30: 4: 1). The peak display of the derivatised plate scanned at 580 nm showed the presence of 19 peaks. 170

11 The extract on reaction with anthrone reagent formed a green coloured mixture which indicated the presence of protein bound polysaccharides. Further, the quantification using anthrone reagent showed the extract contains 9% total carbohydrate content. The phenol-sulphuric acid method also formed a green coloured reaction mixture which confirmed the presence of polysaccharide and the amount of carbohydrate in the extract by the phenol-sulphuric acid method was 8%. The amount of protein present in the extract was estimated to 40% by the Lowry s method. The isolated polysaccharide from G. lucidum was also analyzed for the quantification of the amounts of carbohydrates and proteins. The anthrone method showed that there was 60% carbohydrate in the isolated polysaccharide and it was 52% by the phenol-sulphuric acid method. Similarly, the amount of protein present in the isolated polysaccharide was 18% as estimated by the Lowry s method. Thus, the polysaccharide isolated was found to be a protein-bound polysaccharide or polysaccharide-protein complex. The paper and TLC analysis of the isolated protein-bound polysaccharide by using D-glucose, D-fructose, D-galactose, D-mannose and D-xylose as standards showed that the monosaccharide present is only D-glucose (Fig.9.2 and Fig.9.3), the Rf vales of each standard and the sample were calculated and represented in table 9.2 and the HPLC analysis of the isolated protein-bound polysaccharide also confirmed that the only monosaccharide present in the isolated protein-bound polysaccharide G. lucidum is D-glucose (Fig.9.4.A and Fig.9.4.B). Similarly, the analysis of amino acid composition in the isolated proteinbound polysaccharide from G. lucidum by the TLC method using aspartic acid, glutamic acid, glycine, alanine, histidine, serine, threonine and valine as standards showed that the major amino acids present in the isolated protein-bound polysaccharide were aspartic acid, glutamic acid, alanine and threonine (Fig.9.5) (Table 9.3) The HPTLC analysis of the total triterpenes fraction showed that there are a large number of peaks, the peak display of the derivatised plate scanned at 580 nm showed the presence of 14 peaks (Fig.9.6.A, Fig.9.6.B, Fig.9.6.C and Fig.9.6.D) with 100% chloroform as solvent system. 171

12 Table 9.1 Phytochemical screening of the aqueous ethanol extract of G. lucidum Class of compound Aqueous ethanol extract of G. lucidum Polysaccharide + Terpenoids + Steroids - Alkaloids - Saponins - Coumarins - Tannins - Flavanoids - + indicates presence of compound - indicates absence of compound

13

14

15

16

17 Table 9.2 Analysis of monosaccharide composition in the protein bound polysaccharides isolated from G. lucidum Name Rf value in paper chromatography Rf value in thin layer chromatography Protein bound polysaccharides from G. lucidum D-Glucose D-Fractose D-Mannose D-Rhamnose D-Galactose D-Xylose

18

19 Table 9.3 Analysis of amino acid composition in the protein bound polysaccharide isolated from G. lucidum Name Rf value in thin layer chromatography Protein bound polysaccharides from G. lucidum 0.15 Histidine 0.11 Alanine 0.17 Valine 0.34 Glycine 0.15 Glutamic acid 0.15 Aspartic acid 0.15 Serine 0.13 Threnine 0.15

20

21 9.4. DISCUSSION The G. lucidum has been reported to contain nearly 400 chemical constituents (Wasser, 2005). The results of the present investigation indicate that the G. lucidum from south India contains many chemical constituents. The HPTLC analysis confirms this conclusion. However, the major constituents appear to be triterpenes and polysaccharide-protein complex. A recent study showed that G. lucidum contains numerous bioactive natural components (e.g., protein bound polysaccharides, ganoderic acids, ergosterols, proteins, unsaturated fatty acids, vitamins and minerals) (Niu et al., 2002). The major biological properties of G. lucidum are confined to the abilities of these constituents. Over 300 reports have been published concerning the chemical constituents of G. lucidum and related species. The fruiting body, mycelia, and spores of G. lucidum contain approximately 400 different bioactive compounds, which mainly include triterpenoids, polysaccharides, nucleotides, sterols, steroids, fatty acids, proteins, peptides, and trace elements (McKenna et al., 2002; Smith et al., 2002). More than 200 polysaccharides have been isolated from the fruiting bodies, spores, mycelia and cultivation broth of Lingzhi (Wasser, 2002; Peng et al., 2005). G. lucidum extracts have preventive and curative effects on diseases such as: heart disease, hypertension, hepatitis, diabetes, neurasthenia, tumor and cancer and there are a number of recent reviews stating that the presence of triterpenes and protein bound polysaccharides is the reason behind the amazing biological properties of this medicinal mushroom (Silva, 2004; Paterson, 2006; Poucheret et al., 2006; Zhou et al., 2007). Thus, the different biological properties observed in the current studies also assumed to be due to the high amount of triterpenes and polysaccaharides present in the aqueous ethanol extract of G. lucidum. The major components from the G. lucidum occurring in south India such as protein bound polysaccharides and triterpenes were isolated in our study. The major bioactive protein bound polysaccharides isolated from Ganoderma species are glucans, β-1-3 and β-1-6 D-glucan (Mizuno, 1995). A neutral polysaccharide was recently isolated from G. lucidum occurring in south India which possesses significant radio protective activities (Pillai et al., 2008). The component sugars present in that protein bound neutral polysaccharides were found to have a beta configuration and the 172

22 component sugars are in the pyranoid form (Pillai et al., 2008). MALDI TOF analysis suggested that the molecular weight of protein bound neutral polysaccharides was between 10 and 20 lakhs Dalton (Pillai et al., 2008). From the gel filtration chromatography, the molecular weight of the protein bound polysaccharides was found to be 1.5x10 6 Daltons (Pillai et al., 2008). The current study indicated that the polysaccharide isolated is a mixture of polysaccharide and protein in the ratio 60:18. Thus, it can be called as protein-bound polysaccharide or polysaccharide-protein complex. Further, the monosaccharide present in that polysaccharide is found to be glucose and the amino acids in that polysaccharide-protein complex are found to be aspartic acid, glutamic acid, alanine and threonine. However, further studies are needed to elucidate the exact structure of this polysaccharide-protein complex. The triterpenes fraction isolated was observed to contain a number of triterpenes and the HPTLC analysis of that triterpenes fraction showed a total of 14 peaks corresponding to 14 different constituents present in that fraction. Further detailed tests are needed to find out which are the triterpenes present in this fraction. Thus, the current study showed the major components of the G. lucidum from south India are polysaccharide protein complex and triterpenes. 173

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