Position Moiety Compound III (400MHz) 11 CH-OH 3.85, m 1 H Ansell, 1989 (80MHz) 3.86, ddd (J = 4.7, 7.1, 11.7 Hz) Compound III (400MHz) 13 C # Ansell, 1989 (20MHz) 66.19 69.3 12 CH2 1.82 (α) 1.35 (β) 45.85 40.7 *13 C 39.57 38.7 14 CH= 5.20, s 5.21, d (J = 1.5 Hz) 127.64 128.4 15 CH= 5.72, dd (J = 10.57, 17.21 Hz) 5.74, sx (J = 9.5, 18.1 Hz) 4.87, dd 146.18 145.4 16 CH2 4.89, dd (J = 9.28, 17.4 Hz) (J = 1.9, 18.1 Hz) 4.91, dd (J = 1.9, 9.5 Hz) 112.69 112.5 17 CH3 1.01, s 1.02, s 29.51 29.5 18 CH3 0.99, s 1.00, s 28.43 28.3 19 CH3 0.78, s 0.79, s 15.59 15.7 20 CH3 0.75, s 0.76, s 15.82 16.6 3 OCOCH3 --- --- --- 170.2 3 OCOCH3 --- --- --- 21.1 11 OCOCH3 --- --- --- 170.6 11 OCOCH3 --- --- --- 21.5 * these resonances can be used interchangeably # The 13 C NMR data corresponds to the acetylated product <strong>of</strong> compound III Position 1 2 3 Table 20: 1 H NMR data for compound III (CDCl3) compared with two similar compounds Compound III (400MHz) Compound 3.1 (80MHz) 1 H Compound 3.2 (300MHz) Compound 3.3 (600MHz) Ansell, 1989 Kang et al., 2005 Meragelman et al., 2003 2.35 2.68, s 1.71, dt (J = 13.1, 3.5 Hz) 2.02 0.98 1.69 1.61, m 1.57 1.61, m 3.26, dd (J = 3.84, 10.84 Hz) 3.31, dd (J = 4.5, 9.6 Hz) 4.0, s 3.21, dd (J = 11.1, 5,2 Hz) 5 1.08 1.68, m 0.82 Continued on next page…. 117
Position 6 7 Compound III (400MHz) 9 1.61 Compound 3.1 (80MHz) 1 H Compound 3.2 (300MHz) Compound 3.3 (600MHz) Ansell, 1989 Kang et al., 2005 Meragelman et al., 2003 1.63 1.73, m 1.63, qd (J = 13.4, 3.2 Hz) 1.38 1.49 1.48 2.13, m 1.22 1.85 2.35, m 2.02, d (J = 5.7 Hz) 11 3.85 4.0, m 12 1.82 1.63, m 15 16 5.72, dd (J = 10.57, 17.21 Hz) 4.89, dd (J = 9.28, 17.4 Hz) 5.74, septet (J = 18.4, 8.6 Hz) 4.90, dd (J = 2.1, 18.4 Hz) 4.96, dd (J = 2.2, 8.5 Hz) 5.83, dd (J = 10, 17.8 Hz) 4.94, d (J = 10 Hz) 5.00, d (J = 17.8 Hz) 1.78, dt (J = 13.4, 3.2 Hz) 0.85 1.47 (α), qd (J = 13.4, 3.1 Hz) 1.47 (β), m 2.01, dq (J = 13.7, 3.1 Hz) 5.98, dd (J = 17.9, 11.0 Hz) 5.09, dd (J = 11.0, 1.2 Hz) 5.14, dd (J = 17.9, 1.2 Hz) 17 1.01, s *1.09, s 1.05, s 0.91, s 18 0.99, s *1.10, s 1.19, s 0.99, s 19 0.78, s *0.84, s 0.69, s 0.81, s 20 0.75, s *0.92, s 0.80, s 0.93, s * Resonance for each methyl group not specified Table 21: 13 C NMR data for compound III (CDCl3) compared with two similar compounds Compound 3.1 Compound 3.2 Compound 3.3 Position Compound III (80MHz) (75MHz) (50MHz) Ansell, 1989 Kang et al., 2005 Meragelman et al., 2003 1 35.74 37.3 52.2 37.8 2 27.59 27.7 211.0 27.2 3 78.86 79.2 82.2 79.1 4 39.11 38.3 45.3 38.9 5 53.99 54.3 53.3 55.6 6 22.55 22.3 22.3 17.8 7 38.38 35.8 35.2 42.0 8 137.46 137.9 134.6 72.3 9 59.83 51.3 59.1 56.2 Continued on next page… 118
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UNIVERSITY OF KWAZULU-NATAL FACULTY
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Preface The experimental work descr
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Acknowledgements First and foremost
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GC-MS - gas chromatography-mass spe
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Table 19: NMR data of compound III
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Spectrum 1d: Expanded DEPT spectrum
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Compound V, stigmasterol 217 Spectr
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2 19 1 4 18 O 20 5 Structures of co
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3.4 Results and Discussion of the c
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compounds are also classified as tr
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1 H CO2H 19 20 CHO 18 10 5 H 12 14
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may be referred to as a norabietane
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In the mevalonic acid pathway, the
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N thiamine diphosphate (TPP) O OH N
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in the kauranes. From the kauranes,
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References Abad, A., Agullo, C., Cu
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The flower colour varies among the
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Clade 1 unplaced groups Group A: Pl
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different medical conditions and in
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Plectranthus species Skin condition
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Plectranthus species Heart, circula
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Use of the minimum inhibitory conce
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Plectranthus species Coleus kiliman
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Plectranthus species Extraction med
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Plectranthus species Coleus kiliman
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Methanol, ethanol and water seem to
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Plectranthus species P. amboinicus
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Plectranthus species P. amboinicus
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variation is observed within ring B
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Compound Name Synonym 39 40 41 42 4
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compounds (Table 6b). Depending on
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Table 6c: Royleanone-type abietanes
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R 1 R2CH2 19 O H 3CCO 19 O H 6 12 O
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Compound Name Synonym 81 82 83 84 8
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Compound Name Synonym 104 105 106 1
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R 1 19 3 3 1 18 1 18 20 20 O H O H
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educed furan ring. The linear side
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Compound Name Synonym HCO O 128 129
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Thirty-six compounds (131-167) havi
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Compound Name Synonym 147 148 HO HO
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In compounds 149-165 (Table 9b), an
- Page 83 and 84: Compound Name Synonym 163 164 165 R
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- Page 87 and 88: 1 18 3 20 4 O 5 19 R 1 R2 11 9 10 A
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- Page 95 and 96: Table 14 contains six abietanes iso
- Page 97 and 98: References Abdel-Mogib, M., Albar,
- Page 99 and 100: Cos, P., Hermans, N., de Bryne, T.,
- Page 101 and 102: Hulme, M. (1954) Wild flowers of Na
- Page 103 and 104: Lingling, X., Jie, L., Weijia, L. a
- Page 105 and 106: Oliveira, P.M., Alves, R.B., Ferrei
- Page 107 and 108: Ruedi, P. and Eugster, C. H. (1977)
- Page 109 and 110: Ulubelen, A., Birman, H., Oksuz, S.
- Page 111 and 112: Chapter 3 Extractives from Plectran
- Page 113 and 114: 4 20 10 O H 19 18 6 7 OH OH C 13 R
- Page 115 and 116: a few cases (specifically stated in
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- Page 121 and 122: 3.4.1 Structural elucidation of Com
- Page 123 and 124: esonance showed HMBC correlations t
- Page 125 and 126: esonance at δC 185.76 of C-14 is a
- Page 127 and 128: Position Moiety Compound I 3 CH2 5
- Page 129 and 130: Table 18: 13 C NMR data for compoun
- Page 131 and 132: The equatorial methyl group at C-4,
- Page 133: The proton NMR data for compound II
- Page 137 and 138: 3.4.3 Structure elucidation of Comp
- Page 139 and 140: showed HMBC correlations to another
- Page 141 and 142: H HO 3 OH H 2 4 24 eq 1 23 5 ax Hax
- Page 143 and 144: HO HO Position 2 23 4 10 24 25 26 9
- Page 145 and 146: Position Compound IV 4.1 4.2 4.3 b
- Page 147 and 148: multiplet at δH 1.91 (H-21) and a
- Page 149 and 150: 1 H Position Compound VI Burns et a
- Page 151 and 152: Ultraviolet spectrum (λ max): 192n
- Page 153 and 154: References Ansell, S.M. (1989) The
- Page 155 and 156: Laing, M.D., Drewes, S.E. and Gurla
- Page 157 and 158: van Vuuren, S. (2007) The antimicro
- Page 159 and 160: Since the 7α-isomers of compounds
- Page 161 and 162: eing incubated for 24 hours at 37°
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- Page 167 and 168: whereas GI50 values for the renal a
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- Page 173 and 174: Chapter 5 Conclusion The aim of thi
- Page 175 and 176: References Abdel-Mogib, M., Albar,
- Page 177 and 178: Table of Contents Page Compound I,
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HO 218
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HO 220
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222
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225
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227