CHARACTERIZATION OF DESERT DATE (Balanites aegyptiaca)

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Table 2.1. Major HPLC-RI peaks of methanol-extracted B. aegyptiaca mesocarp, with m/z values obtained from ESI-MS. Peaks Retention Time (min) m/z a [M-H] - Amount (%) b 1 4.2 1195 1.35 2 4.8 1063 18.75 3 6.0 1077 0.95 4 7.2 1209 7.15 5 8.2 1077 5.62 6 9.6 1209 4.65 7 11.1 1077 4.32 8 12.4 1045 1.55 a The m/z values cited are integers obtained by truncating (not rounding off) measured values. b Amount is calculated based on the chromatographic peak area from the injected sample. Characterization of the B. aegyptiaca mesocarp saponins by LC-ESI-MS n Characterization of the saponin peaks obtained from the LC-MS was carried out by MS n experiment in order to determine the structural pattern of each of the saponin peaks. The ESI-MS/MS in negative ion mode of saponin peaks of B. aegyptiaca fruit mesocarp obtained from the LC-RI and LC-ELS (m/z 1195, 1063, 1077, 1209, and 1045) is presented in Figure 2.3. The ESI-MS/MS spectra of the largest peak (Peak 2, m/z 1063) shows the six main fragment ions at m/z 917, 901, 755, 593, 431, and 413 (Figure 2.3b). The differences in mass between the parent ion (m/z 1063) and the fragment ions (m/z 917 and 901) are 146 and 162 Da, indicating the loss of a deoxyhexose sugar and a hexose sugar unit, respectively. The competing lost sugar units suggest that there are two different terminal residues in the oligosaccharide chains, one a hexose unit (most probably glucose), the other a deoxyhexose unit (most probably rhamnose) which fits with the earlier study of saponins (Cui et al., 2000). The fragment ion at m/z 755 corresponds to loss of a disaccharide consisting of a deoxyhexose and a hexose. The ion at m/z 593 shows the loss of a hexose unit; the ion at m/z 431 shows the loss of two hexose units from the ion at m/z 755. The smallest fragment ion (m/z 413) corresponds with the further loss of one H2O unit. This, the smallest of the fragments, fits the molecular mass of dehydrated diosgenin (-H2O), indicating that this is the type of aglycone that comprises B. aegyptiaca saponin. This 23
corresponds with the claims of earlier studies that diosgenin is the sapogenin of B. aegyptiaca (Liu and Nakanishi, 1982; Kamel, 1998). In addition, in the CID spectrum of the main fragment ions, the elimination of 18 Da, corresponding to cleavage of the H2O, was also observed. However, the loss of 18 Da was always at low intensity (Figure 2.3b). For further characterization, an MS n experiment was carried out on the m/z 1063 parent ion. The cleavages of the main peak (MS 2 ) are at m/z 917, 901, 883, 755, 737, 593, 431, and 413. The intensity of the peak at m/z 901 is greater than that at m/z 917, demonstrating that the [M-H] - ion preferentially expels glucoside from the C-26 position (Liu et al., 2004). The MS 3 of the m/z 901 produces m/z 755, m/z 739, and m/z 593. Further, MS (MS 4 ) of the m/z 755 produces fragment ions at m/z 737, m/z 593, and m/z 575 (Table 2.2). Figure 2.3a shows the fragment ions of the m/z 1195 parent ion (Peak 1). There are seven fragment ions: at m/z 1063, 1049, 917, 901, 755, 593, and 431. The mass differences between the parent ion and the fragment ions at m/z 1063 and 1049 are 132 and 146 Da, respectively. These indicate losses of a pentose sugar and a deoxyhexose sugar, respectively. The competing losses of a pentose and a deoxyhexose sugar suggest that there are two different terminal residues in the oligosaccharide chains, most probably a xylose and a rhamnose. The presence of the ESI-MS pattern of the other succeeding fragment ions (917, 901, 977, and 413) shows the similarity of the behavioral pathway of this saponin with the saponin (m/z 1063) described earlier. This suggests that this saponin peak has one more pentose (most probably xylose) unit than the main saponin of B. aegyptiaca fruit mesocarp (MW 1064 Da) described previously with the same aglycone, diogenin. 24
Page 1 and 2: CHARACTERIZATION OF DESERT DATE (Ba
Page 3 and 4: This work was carried out under the
Page 5 and 6: Abstract The desert date (Balanites
Page 7 and 8: of various Balanites tissues sugges
Page 9 and 10: Contents Acknowledgements i Abstrac
Page 11 and 12: Materials and methods 38 - Sample c
Page 13 and 14: - Effect of the saponin source on p
Page 15 and 16: Figure 2.9 1 H NMR spectrum showing
Page 17 and 18: List of Tables Table 2.1 Major HPLC
Page 19 and 20: Glossary CID collision induced diss
Page 21 and 22: Thesis organization This thesis is
Page 23 and 24: fruits have been found in Pharaohs'
Page 25 and 26: Fig 1.3. Map showing the Balanites
Page 27 and 28: themselves provide shade and shelte
Page 29 and 30: should be no surprise that the name
Page 31 and 32: Association with membranes Most bio
Page 33 and 34: the African or Indian samples. No w
Page 35 and 36: Objective and Hypothesis Objectives
Page 37 and 38: CHAPTER 2 Characterization of the f
Page 39 and 40: Extraction and separation For the e
Page 41 and 42: and analysed with an ELS detector (
Page 43: c d a Figure 2.2. Electrospray mass
Page 47 and 48: Table 2.2. MS n Electrospray mass s
Page 49 and 50: 1209, and could be isomers of these
Page 51 and 52: compound as 26-(O-β-D-glucopyranos
Page 53 and 54: In the 1 H NMR spectrum, resonances
Page 55 and 56: Figure 2.11. Structure of the sapon
Page 57 and 58: Conclusions From this study we can
Page 59 and 60: that a study of the saponin profile
Page 61 and 62: HPLC pump and a refractive index (R
Page 63 and 64: Table 3.1 Peaks, retention time, am
Page 65 and 66: (a) (b) (c) (d) (e) Figure 3.2 ESI-
Page 67 and 68: Table 3.2 The LC-ESI-MS and corresp
Page 69 and 70: quoted here also are integers obtai
Page 71 and 72: (a) (b) (c) (d) (e) (f) (g) (i) Fig
Page 73 and 74: considered cleavage behavior, from
Page 75 and 76: Table 3.4 The LC-ESI-MS and corresp
Page 77 and 78: The results of this study also show
Page 79 and 80: ich extracts of Agave sisalana (Piz
Page 81 and 82: food preparation based on baby food
Page 83 and 84: Table 4.3 LC50 and LC90 (ppm) of sa
Page 85 and 86: 1 2 3 Figure 4.1 Structure of the t
Page 87 and 88: When the images of dead larvae were
Page 89 and 90: CHAPTER 5 Antifungal activity of sa
Page 91 and 92: visually and microscopically, and s
Page 93 and 94: Effects of the SREs on in vitro gro
Page 95 and 96:
Table 5.2 Effect of saponin rich ex
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(Table 5.3). In the case of C. cocc
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CHAPTER 6 Effect of saponins on del
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astomatous cuticles from the upper
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Results Effect of the saponin sourc
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Effect of humidity and temperature
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Table 6.3 Effect of humidity and te
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Discussion and conclusions Agro-mat
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solutions used in our studies has s
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CHAPTER 7 General conclusions and s
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as a delivery adjuvant, not only in
Page 117 and 118:
Botanic Gardens, Kew. 960 pp. Bushw
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Ganzera, M., Bedir, E., Khan ,I.A.
Page 121 and 122:
Keukens, E.A.J., de Vrije, T., van
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Morrissey, J.P., Osbourn, A.E. (199
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Schonherr, J., Riederer, M. (1986).
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Appendices A1 - A4: Articles publis
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new and alternative sources of thes
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first dissolved in 1 ml methanol an
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In Table 1, the total sapogenin as
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114 5. Beneytout JL, Nappez C, Lebo
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Appendix: A2 Natural Product Commun
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min, and finally rinsed three times
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level was significantly increased f
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Table1. Effect of plant growth regu
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A B C D Fig 1. Different callus typ
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Appendix: A3 African Journal of Bio
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The data obtained were statisticall
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Table 4. Mortality of Culex pipiens
Page 153 and 154:
Appendix: A4 Dengue Bulletin 2005;
Page 155 and 156:
of the Institutes for Applied Resea
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References 136 1. Halstead SB. Glob
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112 H20a-H21-H23b-H24bb 23a 31.5 1.
Page 161 and 162:
112.0 H15 β -H17a-H20a-H21 23a 31.
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112 H20b-H24aa-H24bb 23a 31.4 1.64
Page 165 and 166:
םהיתויוליעפו םהיתו
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. םיינגוזה םורדו תח
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םוקאזה ישרושב ירקי
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םיטביה לש הנבהה היי
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CHARACTERIZATION OF DESERT DATE (Balanites aegyptiaca)

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