CHAPTER 3 RESULTS AND DISCUSSION. pharmocological effect of the leaf extract of the plant.

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1 CHAPTER 3 RESULTS AND DISCUSSION Sesbania grandiflora is a plant belongs to the family Fabaceae, and its various parts like roots, bark leaves, flower and fruit are known to posses of different pharmocological properties. The objectives of the present work were to bring out the pharmocological effect of the leaf extract of the plant. The shade dried S. grandiflora leaves were extracted in a soxhlet apparatus using different solvents like petroleum ether, methanol, ethanol, chloroform and acetone. The yield obtained from different solvents varied between 13 % to 25 %. The maximum yield was obtained with methanol where as the minimum was with acetone (Table 1). Initial screening of the phytochemical study showed the presence of alkaloids, terpenoids, saponins, flavonoids, phenols, glycosides, tannins, anthraquinones and steroids in the extract (Table 3). Presence of nutrients like proteins, lipids and carbohydrates were also observed (Fig. 1a). From leaf extracts the content of minerals were analyzed using AAS which revealed the presence of calcium, phosphorus, potassium, copper and ferrous ions. Their respective concentrations were 0.15, 0.052, 0.1, 0.35 and 0.04 mg/ g dw (Fig. 2). Pigments like chl a, chl b and carotenoids were also analysed and found to be 2.8, 2.5 and 1.2 mg/g wet wt (Fig.3). 60

2 The proximate analysis of dried leaves showed 3.8 mg/g dw of protein, 5.2 mg/g dw of carbohydrate and 1.0mg/g dw of lipids. Free amino acid were found at a concentration of 3.4 mg/g dw (Fig. 1a). In the present investigation important phytochemicals like alkaloids, phenols, flavonoids and ascorbic acids were quantitatively estimated using standard procedures. Among different extracts tried methanol extract showed higher concentrations of the important phytochemicals (i.e) total alkaloids at the level of 1.9 mg/g dw, total phenols at a concentration of 28.4 mg GAE/g dw and total flavonoids at 5.5 mg QE/g dw where as ascorbic acids was found to be 119 mg/g dw (Fig. 1b). As methanol extract was found to be rich in important phytochemicals, further pharmacological evaluations were done using this extract only. Table 1. Yield of total phenols from S. grandiflora leaves by using various solvents Yield in various extraction solvents Phytochemicals Total Phenols Petroleum ether Chloroform Methanol Ethanol Acetone (mg GAE/g d wt.) 61

3 Table 2. Yield of total flavonoids from S. grandiflora leaves by using various solvents Phytochemicals Total Flavonoids (mg QE/g d wt.) Yield in various extraction solvents Petroleum ether Chloroform Methanol Ethanol Acetone Table 3- Screening of Phytochemicals in S.grandiflora (Methanolic Leaf extract) S.No. Chemical content Result 1 Flavonoids + 2 Tannins + 3 Steriods + 4 Alkaloids + 5 Terpenoids + 6 Anthroquinone + 7 Saponins + 8 Protein + 9 Carbohydrate + 10 Glycosides + 11 Lipid + 62

4 6 Concentration (mg/g dry weight) Protein Free amino acid Carbohydrate Lipid Fig. 1a Proximate analysis Phytochemicals (Methanolic extract) Concentration (mg/g dry weight) Total Phenols 5.5 Total Flavonoids Ascorbic acid Phytochemicals Alkaloids Fig. 1b - Phytochemical analysis 63

5 Minerals Analysis Concentration (mg/g dry weight) Ca P K Cu Fe Minerals Minerals Fig. 2- Minerals analysis Pigments Analysis Concntration (mg/g fresh weight) Chlorophyll a Chlorophyll b Carotenoid Pigments Pigments Fig. 3- Pigment analysis 64

6 Absorbance at 750nm Gallic acid Standard curve y = 0.097x R 2 = Concentration (mg/ml) Gallic acid Fig. 4- Gallic acid Standard curve 0.3 Quercetin Standard curve y = 0.013x R 2 = Absorbance at 420nm Quercetin Concentration (mg/ml) Fig. 5 - Quercetin Standard curve 65

7 Pharmacological potentials of crude extract The crude methanol extract was tested against bacterial and fungal pathogens and the results were given below. Antibacterial In the present investigation the methanol extract of S grandiflora leaves showed highest activity to S. aureus (25mm) followed by B.cereus (18mm), E.coli (16mm), P. aeruginosa (11mm), L. monocytogenes (9mm), S. typhi (5mm), V. cholerae (5mm) and S. flexneri (5mm). It did not show any activity against S. paratyphi and V. parahaemolyticus. The MIC values obtained in the present study against various pathogens were in the range of 11 to 22 mg/ml. This value was comparatively lesser to the S. grandiflora extracts tested by others in various regions. The lowest MIC value was observed against S. aureus and the highest MIC of 22mg/mL was observed against S. typhi (Table 4). 66

8 Table 4 - Antibacterial activity of crude extract of S.grandiflora against human bacterial pathogens Pathogens Petroleum ether Chloroform Methanol Ethanol Acetone S. aureus 13mm 14mm 25mm 10mm 11mm B.cereus 9mm 6mm 18mm 6mm 5mm E.coli 5mm 7mm 16mm 3mm 2mm P.aeruginosa 3mm 2mm 11mm 5mm 4mm L.monocytogenes 2mm 1mm 9mm 2mm 3mm S.typhi 2mm 1mm 5mm 1mm 1mm V.cholerae 1mm 1mm 5mm 2mm -- S.flexneri 1mm -- 5mm 1mm -- S.typhi V.parahaemolyticus Antifungal In the present study along with C.albicans a human pathogen ten different plant fungal pathogens were also evaluated against the methanol extract. Lower activity was observed towards C.albicans whereas none of the plant fungal pathogens was inhibited. 67

9 On contrary to the higher antibacterial activity, S. grandiflora did not show appreciable antifungal activity. In the present investigation C. albicans was the only human fungal pathogens tested to which moderate activity observed. The MIC value observed was 25mg/mL. For the rest of the 10 plant pathogens tested, none of the pathogen activity was found MIC values could not be atributed as no inhibitory activity was observed when tested up to 50mg/mL The crude methanol extract was tested for various antioxidant assays to evaluate its potencial. In the present investigation total antioxidant assay, DPPH scavenging activity, super oxide radical scavenging activity, hydroxyl radical scavenging activity, hydrogen peroxide scavenging activity were done. Purification and identification of compounds Based on the antimicrobial activity further purification was done using column chromatography by adopting the following methodology. Air-dried aerial parts of the plant (500 g) were extracted 3 times (3x1L) with MeOH at 40 o C. The extracts were filtrated and combined. The combined filtrate was evaporated under vacuum to dryness (62 g). The residue was suspended in H 2 O (100 ml) and partitioned with CHCl 3 (4 x 100 ml). The aqueous layer (34 g) was subjected to a column of Sephadex LH 20 eluting with CH 3 OH to yield 7 main fractions (F1-F7): F1-4.9 g, F2-2.8 g, F3-2.3 g, F4-1.7 g, F5-1.2 g, F6-0.9 g and F7-0.63). F5 was eluted with CH 3 OH from the Sephadex LH 20 column and was separated by preparative TLC using CHCl 3 - CH 3 OH -H 2 O (61:32:7) mixtures as developing solvent to yield 5 main fractions: F5.1- F5.5. F5.3 was purified by preparative TLC using 68

10 CH 3 COOCH 2 CH 3 -HCOOH- CH 3 COOH -H 2 O (100:11:11:27) solvent to give compound 2 (4.1 mg). F5.4 was purified by preparative TLC using CH 3 COOCH 2 CH 3 - HCOOH- CH 3 COOH -H 2 O (100:11:11:27) solvent to give compound 3 (2.7mg) and compound 4 (5.4 mg). F5.5 was subjected to a column of Sephadex LH 20 eluting with CH 3 OH to give compound 1 (1.8 mg). F5.5 was subjected to a column of Sephadex LH 20 eluting with CH 3 OH to give compound 5 (4mg) and was separated by preparative TLC using CHCl 3 - CH 3 OH -H 2 O (60:30:10) mixtures as developing solvent to yield single fraction. All the compounds from the fractions were purified using preparative TLC and individual compounds were checked for antibacterial and antioxidant activity. Positive samples were further characterized were readily identified based on their spectroscopic data (1D- and 2D-NMR), FTIR and also by comparing their physico-chemical and spectroscopic data with those reported in the literature. Among the 5 compounds only three were considered for the present study. Identification of compounds using advanced techniques The compounds were identified as Lupeol, Kaempferol and gallic acid and their molecular structures were elucidated. Identification of compound -1 Compound 1 was identified as lupeol and the results are given below 69

11 NMR Analysis of Sesbania grandifolra Compound-1 Analysis of 1 H NMR spectrum of compound-1 1 H NMR (CDCl 3, 400MHz) δ 0.761, 0.788, 0.829, 0.945, 0.968, 1.030, The 1 H NMR spectrum revealed the presence of seven tertiary methyl protons at δ 0.761, 0.788, 0.829, 0.945, 0.968, and A sextet of one proton at δ ascribable to 19β H is characteristic of lupeol. The 1 H NMR spectrum revealed the presence of seven tertiary methyl protons at δ 0.77, 0.79, 0.85, 0.94, 0.97, 1.05 and 1.65 (integrated for 3H-each). A pair of broad singlets at δ and δ (IH, each) was indicative of olefinic protons at H-29 a and b. These assignments are in good agreement for the structure of lupeol (Stahl, 1969 and Abdullahi et al., 2013). Analysis of IR spectrum of compound-1 IR v max (CCl 4 ) cm -1 : CH, C=C, and Aromate, O-H, Ether C-O. The IR spectrum of R1 showed characteristic absorption frequencies at and cm- 1 typical of the O-H and C-O bond vibrations, respectively. Stretching vibration band at 2947cm -1 was due to methyl group. The signal at 1463cm -1 was due to methylenic vibration. Vibration at 1462cm -1 and was due to CH 2 and C-H bend respectively. Analysis of 13 C NMR spectrum of compound-1 13 C NMR (CDCl 3, 100MHz) δc 38.72(C-1), 27.46(C-2), 79.04(C-3), 38.88(C-4), 55.31(C-5), 18.02, 18.34(C-6), 34.29(C-7), 40.85(C-8), 50.45(C-9), 37.19(C-10), 20.94(C-11), 25.15(C-12), 37.19(C-13), 42.85(C-14), 27.46(C-15), 35.60(C-16), 42.85(C-17), 48.32(C-18), 48.01(C-19), (C-20), 29.86(C-21), 40.02(C-22), 28.01, 70

12 27.46(C-23), 15.39(C-24), 16.14(C-25), 15.99(C-26), 14.57(C-27), 18.02(C-28), (C-29) and 19.32(C-30). The 13 C NMR experiments which showed seven methyl groups at (δc: 28.01(C- 23), 18.02(C-28), 16.14(C-25), 15.99(C-26), 15.39(C-24), 14.57(C-27) and 19.32(C-30). The signals due to an exomethylene group found at δc: (C-29) and (C-20). Ten methylene, five methine and five quaternary carbons were assigned with the aid of DEPT experiment. The deshielded singnal at δc was due to the attachment of C-3 with a hydroxyl group. The confirmation of the structure of Compound-6 was accomplished through the 2D NMR experiments (COSY and HMBC). The COSY spectrum of Compound-6 exhibited some cross peaks such as between δh 2.37, H-19 and one sp 3 methylene proton signal (δh 1.37, H-21) and another sp 3 methine proton signal (δ H 1.89, H-18); and between oxygenated methine proton signal (δh 3.2, H-30 and sp 3 methylene signal (δh 1.60, H-2). In the HMBC spectrum, the methine proton signal at δh 3.2 (H-3) showed cross peaks with a methyl carbon signal (δc 28.0, C-23) by J2 correlation and a methyl carbon signal (δc 18.5, C-6) by J3 correlation. The sextet methyl signal at δh 2.37 (H-19) showed cross peaks with two methylene carbon signals δc 29.9 (C-21) and δc (C- 29)], a methine carbon signal [δc 48.3 (C- 18), a methyl carbon signal [δc 19.5 (C-30)] and a quaternary carbon signal [δc (C-20)]. The pair of broad singlets of olefinic proton at δh 4.55 and 4.70 showed cross peaks with a methylene carbon signal (δc 48.0 (C-19) and δc 19.5 (C-30) by J3 correlation. The forgoing spectral analysis and, comparison with reported data, led us to propose the structure of R1 as lupeol, a 71

13 pentacylic tri-terpenoid, and the respective figure is given below. Hence, the probable structure of compound was Lupeol (Molecular formula C 30 H 50 O). Fig. 6 Lupeol structure Fig. 7 FT-IR (KBr) Spectrum of Lupeol 72

14 Fig. 8 COSY NMR (CDCl 3-400MHz) analysis of Lupeol 73

15 Fig. 9a 13 C NMR (CDCl MHz) spectrum of Lupeol 74

16 Fig. 9b Expansion of Fig. 9a 75

17 Fig. 10 DEPT NMR (CDCl MHz) Spectrum of Lupeol 76

18 Fig. 11a 1 H NMR Spectrum (CDCl MHz) of Lupeol 77

19 Fig. 11b Expansion of Fig. 11a 78

20 Fig. 12a HMBC NMR (CDCl 3-100MHz) analysis of Lupeol 79

21 Fig. 12b Expansion of Fig. 12a 80

22 Fig. 13a HSQC NMR (CDCl 3-100MHz) analysis of Lupeol 81

23 Fig. 13b Expansion of Fig. 13a 82

24 Identification of compound -2 Compound 2 was identified as Kaempferol and the results are given below NMR Analysis of Compound 2 Analysis of 1 H NMR spectrum of compound-2 In 1 H NMR spectrum of compound-2, there was no proton signal at in the aliphatic region. All signals are all observed between δ 6.3 to 11.98ppm. The signals at δ 9.35, and 11.98ppm are due to phenolic and enolic OH protons. The other protons at δ 6.30, 6.43, 6.96 and 8.07 were assigned to aromatic protons. The 13 C shows no signals in the aliphatic region, all signals were observed only in aromatic regions. Analysis of 1 H- 1 H COSY and HSQC spectrum of compound-2 Only one correlation (cross peak) observed in COSY spectrum shows correlation between 6.98ppm and 8.09ppm. This revealed that these two protons are adjacent to each other. and carbons. In HSQC spectrum four correlations were observed between the following proton ppm ppm pm ppm 83

25 Analysis of IR spectrum of compound-2 IR spectrum of compound-2 showed a strong broad absorption at cm -1. This absorption band was due to hydrogen bonded phenolic or enolic OH. Two moderate absorption bands at 2899 and 2833cm -1 were due to aromatic CH. Stretching and one broad absorption at 1649cm -1 due to hydrogen bounded carboxyl stretching. Structure of compound-2 All IR and NMR spectra showed four OH groups. Among the four, three of them were phenolic in nature and remaining OH was found to be enolic and hydrogen bonded with carboxyl group. Hence, the probable structure of compound was kaempferol (Molecular formula C 15 H 10 O 6 ). Fig. 14- kaempferol structure 84

26 Fig FTIR spectral analysis of Kaempferol 85

27 Fig C NMR (CDCl 3-100MHz) Analysis of Kaempferol 86

28 Fig. 17a COSY NMR (CDCl 3-400MHz) Analysis of Kaempferol 87

29 Fig. 17b Expansion of Fig. 17a 88

30 Fig. 18 DEPT NMR (CDCl 3-100MHz) Analysis of Kaempferol 89

31 Fig. 29a 1 H NMR (CDCl 3-400MHz) Analysis of Kaempferol 90

32 Fig. 19b Expansion of Fig. 19a 91

33 Fig. 20a HMBC NMR (CDCl 3-100MHz) Analysis of Kaempferol 92

34 Fig. 20b Expansion of Fig. 20a 93

35 Fig. 21a HSQC NMR (CDCl 3-100MHz) Analysis of Kaempferol 94

36 Fig. 21b Expansion of Fig. 21a 95

37 Identification of compound -3: Compound 1 was identified as Gallic acid and the results are given below NMR Analysis of Compound 3 Analysis of 1 H NMR spectrum of compound-3 Analysis of 1 H NMR spectrum of compound-3 (Plate-1) three proton signals was observed at δ 7.161, and 8.274ppm. The two broad signals at δ and 8.274ppm are due to the phenolic OH protons. The aromatic CH protons are appeared at δ 7.161ppm with proton integral. Analysis of 13 C NMR spectrum of compound-3 The 13 C NMR spectrum of compound-3 showed five signals at δ 109.6, 121.4, 137.3, and 168.8ppm. The carbon resonate at 168.8ppm is due to the carbonyl carbon. The aromatic carbons are appeared in the range of ppm. The specific assignment was carried out from HSQC spectrum of compound-3. Analysis of HSQC and COSY of compound-3 Analysis of HSQC and COSY of compound-3 gave only the correlation between proton signal at δ 7.161ppm and carbon signal at 109.6ppm this correlation revealed that the proton signal at δ 7.161ppm is due to the aromatic CH proton and the carbon signal at 109.6ppm is due to the aromatic carbon. No other correlations were observed in HSQC. Hence, there was no cross peaks observed in 1 H- 1 H, COSY spectrum it revealed that there is no coupling between two aromatic protons. 96

38 From the analysis of all the spectral data, the compound was found to contain three phenolic OH group and carboxyl group with symmetrical structure without direct coupling protons. Hence, the structure of the compared was found to be 3, 4, 5- Trihydroxyl benzoic acid (i.e.) gallic acid (Molecular formula C 7 H 6 O 5 ) as given below. Fig. 22 Gallic acid structure Fig. 23 FTIR spectral analysis of Gallic Acid 97

39 Fig C NMR (CDCl 3-100MHz) Analysis of Gallic Acid 98

40 Fig. 25a COSY NMR (CDCl 3-400MHz) Analysis of Gallic Acid 99

41 Fig. 25b Expansion of Fig. 25a 100

42 Fig. 26 DEPT NMR (CDCl 3-100MHz) Analysis of Gallic Acid 101

43 Fig H NMR (CDCl 3-400MHz) Analysis of Gallic Acid 102

44 Fig. 28a HMBC NMR (CDCl 3-100MHz) Analysis of Gallic Acid 103

45 Fig. 28b Expansion of Fig. 28a 104

46 Fig. 29a HSQC NMR (CDCl 3-100MHz) Analysis of Gallic Acid 105

47 Fig. 29b Expansion of Fig. 29a 106

48 The identified compounds were further evaluated for their pharmacological potential. Antibacterial When 25µg/mL of lupeol was tested it resulted in highest inhibitory activity to S. aureus with 45mm zone of clearance followed by B. cereus (40mm), E. coli (35mm), P. aeruginosa (30mm), L. monocytogens (15mm) and V. parahaemolyticus. When crude extract showed lower activity to S.typhi and V.cholerae lupeol did not show any inhibitory activity to these organisms. Surprisingly, when crude extract did not show any activity towards S.typhi and V.parahaemolyticus. lupeol showed lower inhibitory activity against these organisms. The MIC values obtained in the present study against various pathogens were in the range of 11 to 22 mg/ml. Gallic acid also showed most inhibitory activity against S. aureus (43mm) followed by B.cereus (32mm) and E.coli (21mm) P.aeruginosa (27mm) and L.monocytogenes (15mm) whereas S.typhi and V.cholerae showed only 5mm zone of clearance. Kaempferol also showed higher inhibitory activity compared to crude extract. This compound also most inhibited S.aureus (43mm) followed by B.cerus (25mm) and E.coli (19mm) and L.monocytogenes (10mm) and S.typhi (5mm). Kaemferol did not show inhibitory activity against P.aeruginosa, S. typhi, V.cholerae, S. flexeneri and V.parahaemolyticus. 107

49 Table 5 - Antibacterial activity of crude extract and purified compounds of S.grandiflora against human bacterial pathogens Pathogens Crude Lupeol Kemferol Gallic acid S. aureus 25mm 45mm 43mm 43mm B.cereus 18mm 40mm 25mm 32mm E.coli 16mm 35mm 19mm 21mm P.aeruginosa 11mm 30mm - 27mm L.monocytogenes 9mm 15mm 10mm 15mm S.typhi 5mm mm V.cholerae 5mm mm S.flexneri 5mm 5mm S.typhi -- 5mm 5mm 5mm V.parahaemolyticus -- 10mm

50 Lupeol Gallic acid Kaempferol 1- Control, 2 Activity of the compound Fig Antibacterial activity of Lupeol, Kaempferol and Gallic acid against S.aureus 109

51 Kaempferol Gallic acid Lupeol 1- Control, 2 Activity of the compound Fig Antibacterial activity of Lupeol, Kaempferol and Gallic acid against B.cereus 110

52 Lupeol Gallic acid Kaempferol 1- Control, 2 Activity of the compound Fig Antibacterial activity of Lupeol, Kaempferol and Gallic acid against E.coli 111

53 Lupeol Gallic acid 1- Control, 2 Activity of the compound Fig Antibacterial activity of Lupeol and Gallic acid against P.aeruginosa 112

54 Antifungal activity Lupeol showed lower activity (7mm) towards C.albicans a human fungal pathogen. However when tested against plant pathogens like Colletotrichum musae, Sclerotium roysii, Aspergillus niger, Colletotrichum capsici, Fusarium oxysporum, Fusarium udum, Botrytis cinera, Alternaria alternate, Rhizoctonia solani and Macrophomia phaseolina lupeol inhibited 6 pathogens with highest activity towards B.cinera (35mm), followed by F.udum (30mm) C.musae (30mm), A, niger (17mm) and Alternaria alternata (10mm). Gallic acid inhibited C. albicans only at a moderate level (i.e.) 8mm. The plant pathogens F.udam was most inhibited (18mm) by this compound followed by A.alternata (17mm), B.cinera (16mm), A.niger (15mm) and C.musae (15mm). In the present investigation compared to lupeol and kempferol gallic acid showed slightly higher level of inhibition. Kaempferol inhibited C. albicans at moderate level only. However compared to other compounds, the zone of inhibition was observed larger (13mm). Among the fungi tested B.cinera was the most inhibited (26mm) followed by C.musae (18mm) A.niger (10mm) F.udum (10mm) and A. alternata (10mm). The other fungi were found to be resistant to these compounds. 113

55 Table 6 - Antifungal activity of crude extract and purified compounds S.grandiflora against human plant pathogenic fungi Zone of Inhibition (mm) Pathogens tested Lupeol Gallic acid Kaempferol Colletotrichum musae Sclerotium roysii Aspergillus niger Colletotrichum capsici Fusarium oxysporum Fusarium udum Botrytis cinera Alternaria alternata Rhizoctonia solani Macrophomia phaseolina Candida albicans 6mm 114

56 Fusarium udum Aspergillus niger Botrytis cinera Sclerotium roysii Colletotrichum musae Alternaria alternata 1- Control, 2 Lupeol, 3 Gallic acid, 4 - Kaempferol Fig. 34- Antifungal activity of Phytocompounds against plant pathogenic fungi 115

57 Fig. 35- Antifungal activity of Gallic acid, Kaempferol and Lupeol against Candida albicans MIC The MIC value against S. aureus was 2µg/mL where as it was 10µg/mL for L.monocytogens. Among 10 pathogens tested only 5 were inhibited. P. aeruginosa which was inhibited by lupeol and gallic acid was resistant to kaempferol. Moreover when crude extract could not inhibit V.parahaemolyticus, kaempferol showed moderated activity to that pathogen. The MIC values of purified compounds observed in the present study were many fold lower compared to the crude extract. The MIC values observed for lupeol against bacteria were in the range of 1 to 14µg/mL. (Table -7). 116

58 In the present investigation MIC value observed for kemferol was in the range of 1 to 10µg/mL. (Table - 7). (Table - 7) MIC value observed for Gallic acid was in the range of 2.8 to 11µg/mL. However the trend of inhibition was found to be the same.all the three compounds inhibited S.aureus at the level of 1µg/mL. All of them inhibited C.albicans at the level of 3 to10µg/ml.(i.e) The MIC value of Gallic acid against C.albicans was 3µg/mL, Kemferol was 10µg/mL whereas lupeol inhibited at 5µg/mL. Table 7 - MIC for purified phytocompounds from S.grandiflora against human bacterial pathogens MIC Pathogens tested Crude methanolic Purified compounds (µg/ml) extract (mg/ml) Lupeol Kaempferol Gallic acid S. aureus B.cereus E.coli P.aeruginosa L.monocytogenes S.typhi V.cholerae S.flexneri V.parahaemolyticus S.paratyphi

59 Table 8 - MIC for S.grandiflora phytocompounds against human and plant pathogenic fungi MIC Pathogens tested Purified compounds (µg/ml) Lupeol Gallic acid Kaempferol Colletotrichum musae Sclerotium roysii 150 >200 >200 Aspergillus niger Colletotrichumcapsici >200 >200 >200 Fusarium oxysporum >200 >200 >200 Fusarium udum Botrytis cinera Alternaria alternata Rhizoctoniasolani MacrophomiaPhaseolina Candida albicans

60 Antioxidative potential In the present investigation though 5 different assays were done for crude. Only DPPH. assay was followed for purified compounds. When lupeol was tested at the concentration range of 2-10µg/mL respectively, 14, 20, 48, 82 and 99% scavenging activity was observed at 2, 4, 6, 8 and 10 µg. With a mere 2µg of pure compound, it showed 14% activity and also was found to be around 6.1µg/mL (Fig. 41). Among the three isolated compounds, lupeol showed highest reducing activity. DPPH and FRAP assay are general tests used to evaluate the antioxidant capacity of substance. The DPPH radical is commonly used for fast evaluation of the antioxidant property of a given compound. Lupeol is a pentacyclic triterpenes that exhibit antioxidative activity through direct scavenging of free radicals and protects membrane permeability. This property can be related to its hepatoprotective and anticancer properties. In the present investigation though 5 different assays were done for crude, only DPPH. assay was followed for purified compounds. When gallic acid was tested at the concentration range of 2-10µg/mL respectively 12, 15, 40, 76 and 92% scavenging activity was observed at 2, 4, 6, 8 and 10 µg/ml respectively. With a mere 2µg of pure compound, it showed 12% activity and (Fig. 43). Among the three isolated compounds, gallic acid showed the least reducing activity (92%). The present study showed that kaempferol of S.grandiflora origin is of potential scavenger of DPPH. The ability of kaempferol to decrease free radicals levels at low concentrations may play an important role in its antioxidant activity. The DPPH 119

61 scavenging activity was slightly found to be higher compared to the other two compounds. The DPPH activity for kaempferol was found to be 96%. Table 9. Determination of enzymatic antioxidants Concentration (Units/mg protein) Catalase Sample Superoxide dismutase Peroxidase Ascorbic oxidase (µm H 2 O 2 decomposed/min/mg protein) Sesbania grandiflora Leaf extract (Methanol extract) Total Antioxidant activity Antioxidant activity (mg/ml) Concentration (mg/ml) Antioxi - TAA Fig Total antioxidant activity of crude methanolic extract of S.grandiflora 120

62 DPPH scavenging activity Antioxidant activity % Concentration (mg/ml) Antioxi - DPPH Fig. 37- DPPH scavenging activity of crude methanolic extract of S.grandiflora Superoxide radical scavenging activity Superoxide radical scavenging activity (%) Concentration (µg/ml) Superoxide radical Fig. 38- Superoxide radical scavenging activity of crude methanolic extract of S.grandiflora 121

63 Hydroxyl radical scavenging activity Hydroxyl radical scavenging activity (%) Concentration (µg/ml) Hydroxyl radical Fig. 39- Hydroxyl radical scavenging activity of crude methanolic extract of S.grandiflora Hydrogen peroxide scavenging activity Chelation Activity (%) Concentration (µg/ml) Hydrogen peroxide scavenging Fig. 40- Hydrogen peroxide scavenging activity of crude methanolic extract of S.grandiflora 122

64 DPPH Scavenging activity of Lupeol Antioxidant activity % Concentration (µg/ml) Lupeol Fig. 41- DPPH scavenging activity of purified Lupeol from S.grandiflora DPPH Scavenging activity of Kaempferol 100 Antioxidant activity % Concentration (µg/ml) Kaempferol Fig. 42- DPPH scavenging activity of purified Kaempferol from S.grandiflora 123

65 DPPH Scavenging activity of Gallic acid Antioxidant activity % Concentration (µg/ml) Gallic acid Fig. 43- DPPH scavenging activity of purified Gallic acid from S.grandiflora Antiproliferative potential When purified lupeol was used against cancer cell lines (HEP G 2 ), it inhibited the cell viability to 12.5% at a concentration of 1000µg/mL. At 1:64 dilution (i.e.) with 7.81µg/mL of lupeol, it resulted in 75.22% and the IC 50 was found at 62.5µg/mL. This result clearly indicated the potential of lupeol in killing HEP G 2 cancer cells. In the present study Lupeol was found to have both antioxidant and anticancer properties. β-lupeol had been reported not only to induce differentiation and inhibit the growth of melanoma and leukemia cells but also to inhibit tumor promotion in two-stage mouse skim carcinogenesis and to inhibit growth apoptosis in both prostate and pancreatic cancer 124

66 When purified gallic acid was used against cancer cell lines (HEP G 2 ) it inhibited the cell viability to 6.32% at a concentration of 1000µg/mL. At 1:64 dilution i.e. with 7.82µg/mL of gallic acid, resulted in 84.1% and the IC 50 was fund at 31.25µg/mL. This result clearly indicated the potential of gallic acid in killing HEP G 2 cancer cells. Cytotoxity The present investigation clearly indicated kaempferol isolated from S.grandiflora leaves inhibited HEPG 2 (i.e) Lung Cancer cells, a concentration of 62.5 µg/ml (i.e) it seemed to have potent anticarcinogenic activity and possessed preventive and therapeutic properties. However this value seemed to be higher compared to the IC 50 value of lupeol and Gallic acid which was found to be µg/ml. The present study strongly endorsed the role of dietary flavonoids in the prevention of cancer. The study clearly showed that kaempferol as well as the other two compounds of Sesbania grandiflora leaves had potential antibacterial, antifungal, antioxidant as well as anticancer properties. In the present investigation though 5 different assays were done for crude. Only DPPH. assay was followed for purified compounds. The purified kaempferol showed 12% scavenging activity at the concentration to 2µg/mL. which was gradually increased to18, 44, 78 and 96% respectively at 4, 6, 8 and 10 µg/ml respectively. 125

67 Table 10- Cytotoxicity effect of Lupeol on HEP G 2 S.No Concentration (µg/ml) Dilutions Cell Viability Neat : : : : : : : Cell control Cell viability MTT ASSAY IC Concentration (µg/ml) Fig. 44 IC 50 value of Lupeol on HEP G 2 126

68 1000 µg/ml High toxicity 250 µg/ml Medium toxicity µg/ml Normal HEP G 2 cell lines Fig Cytotoxicity (Anticancer) effect of Lupeol on HEP G 2 (Liver Cancer Cell lines) 127

69 Table 11 - Cytotoxicity effect of Kaemferol on HEP G 2 S.No Concentration (µg/ml) Dilutions Cell Viability Neat : : : : : : : Cell control MTT ASSAY Cell viability IC Concentration (µg/ml) Fig. 46 IC 50 value of Kaempferol on HEP G 2 128

70 Toxicity 1 (1000µg/mL) Toxicity 2 (125µg/mL) Toxicity 3 (62.5 µg/ml ) Toxicity 4 ( µg/ml ) Fig Cytotoxicity (Anticancer) effect of Kaempferol on HEP G 2 (Liver Cancer Cell lines) 129

71 Table 12 - Cytotoxicity effect of Gallic acid on HEP G 2 S.No Concentration (µg/ml) Dilutions Cell Viability Neat : : : : : : : Cell control MTT ASSAY Cell viability IC Concentration (µg/ml) Fig. 48 IC 50 value of Gallic acid on HEP G 2 130

72 1000 µg/ml 250 µg/ml µg/ml µg/ml Fig Cytotoxicity (Anticancer) effect of Gallic acid on HEP G 2 (Liver Cancer Cell lines) 131

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