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Physical data for compounds I-VI Compound I Chemical name: 7β-acetoxy-6β,12-dihydroxy-8,12-abietadiene-11,14-dione Common name: 7β-acetoxy-6β-hydroxyroyleanone Molecular formula: C22H30O6 Physical description: yellow crystals Melting point: 197 o C (228 o C, Mehrotra et al., 1989) Optical rotation:[ ] 20 α D +29 o (c 0.0052g/100ml, DCM) (lit. value = +23 o (CHCl3; Cl), Mehrotra et al., 1989) Infrared spectrum ν KBr max cm-1 : 3377 (O-H stretching bands), 1734 (carbonyl stretching bands), 1375 (C-H stretching vibrations), 1641 (alkene stretching bands) Ultraviolet spectrum (λ max): 275 nm (log ε = 1.61) GC-MS (70eV, direct inlet), relative intensity %: m/z 390 (1.46) [M] + , m/z 372 (4.85) [M – H2O] + , m/z 357 (0.97) [M - H2O - Me] + , m/z 71 (100) 1 H NMR and 13 C NMR data (CDCl3, 400MHz): Refer to tables 15 and 16 on pages 109 and 110 Compound II: Chemical name: 6β,7β,12-trihydroxy-8,12-abietadiene-11,14-dione Common name: 6β,7β-dihydroxyroyleanone Molecular formula: C20H28O5 Physical description: yellow residue Melting point: 125 o C (203-205 o C, Hensch et al., 1975) Optical rotation: [ ] 20 α D -47 o (c 0.0063g/100ml, DCM) (lit. value = -77 o , Hensch et al., 1975) Infrared spectrum ν KBr vibrations), 1638 (alkene stretching bands) max cm-1 : 3369 (O-H stretching bands), 1376 (C-H bending 133
Ultraviolet spectrum (λ max): 192nm (log ε = 2.73) LC-MS (70eV, direct inlet): [M] + at 347 (negative ion mode) 1 H and 13 C NMR data (CDCl3, 400MHz): Refer to tables 17 and 18 on pages 111 and 112 Compound III: Chemical name: ent-pimara-8(14),15-dien-3α,11β-diol Physical description: white residue Molecular formula: C20H32O2 Melting point: 89 o C (125-130 o C, Ansell, 1989) Optical rotation: [ ] 20 α D -79° (c 0.0082g/100ml, DCM) Infrared spectrum ν KBr vibrations) max cm-1 : 3396 (O-H stretching bands), 2930 (C-H stretching Ultraviolet spectrum (λ max): 228nm (log ε = 1.70) GC-MS (70eV, direct inlet), relative intensity %: m/z 304 (1.94) [M] + , m/z 135 (100), m/z 286 (10.68) [M – H2O] + , m/z 268 (5.34) [M – 2Me] + 1 H NMR and 13 C NMR data (CDCl3, 400MHz): Refer to table 19 on page 116 Compound IV: Chemical name: 2α,3α,19α-trihydroxyurs-12-en-28-oic acid Common name: euscaphic acid, jacarandic acid Molecular formula: C30H48O5 Physical description: white residue Melting point: 255 o C Optical rotation: [ ] 20 α D +32.26° (c 0.0186g/100ml, MeOH) Infrared spectrum ν KBr 1687 (C=O) max cm-1 : 3424 (O-H stretching bands), 2927 (C-H stretching bands), Ultraviolet spectrum (λ max): 211nm (log ε = 2.05) 134
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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
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Compound Name Synonym 163 164 165 R
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Table 9c: Coleon-type abietanes wit
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1 18 3 20 4 O 5 19 R 1 R2 11 9 10 A
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The majority of the abietanes isola
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Plectranthus species Plant part Com
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The leaves seem to be the most freq
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Table 14 contains six abietanes iso
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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
Page 117 and 118: The leaves (184.63g) were air-dried
Page 119 and 120: The ethyl acetate extract (0.98g) w
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 and 134: The proton NMR data for compound II
Page 135 and 136: Position 6 7 Compound III (400MHz)
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: 1 H Position Compound VI Burns et a
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°
Page 163 and 164: This indicated that the dihydroxy c
Page 165 and 166: acetic acid and air drying the plat
Page 167 and 168: whereas GI50 values for the renal a
Page 169 and 170: Table 28: Growth inhibition values
Page 171 and 172: Gaspar-Marques, C., Duarte, M.A., S
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,
Page 179 and 180: Compound II, 6β,7β-dihydroxyroyle
Page 181 and 182: Compound IV, euscaphic acid HO HO 2
Page 183: HO Compound VI, lupeol 3 24 25 26 2
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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
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