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H 1,3 H + migration H H 12 13 14 D H 16 15 Intermediate II H H D 16 15 13 C sandaracopimarenyl cation H H H 8 (Intermediate I) -H (17) 19 16 4 17 15 -H + (16) H H HO 16 14 H H 12 CH 2OH 15 13 17 13 12 17 15 9,16-bond formation 8 14 1,2 H + loss of CH2 11 20 H 9 shift 18 Atisirene (atisane type compound) 16 Beyerol (beyerane type diterpene) CH 2OH 15 -H (12) 12,15-bond formation 19 4 20 18 19 4 18 20 aconane type compound 12 17 15 13 16 9 8 trachylobane type diterpene 15 16 9 8 Figure 11: Biosynthesis of beyerane, trachylobane, atisane and aconane diterpenes (Manitto, 1981) The loss of a proton at C-14 in the sandaracopimarenyl cation leads to the formation of a double bond between C-8 and C-14 after which a methyl migration from C-17 to C-15 yields an abietenyl cation, which loses a proton at C-7 to produce abietadiene (figure 12). H H 8 14 16 H 17 H 8 sandaracopimarenyl cation (-)-sandaracopimaradiene H 15 17 14 H H H 7 H 16 15 abietenyl cation O (-)-abietadiene Figure 12: Synthesis of abietadiene (reproduced from Dewick, 2002) H H 13
References Abad, A., Agullo, C., Cunat, A.C., de Alfonso Marzal, I., Navarro, I. and Gris, A. (2006) A unified synthetic approach to trachylobane-, beyerane-, atisane- and kaurane-type diterpenes, Tetrahedron, 62, 3266-3283 Dev, S. (1985) CRC handbook of terpenoids, Diterpenoids, CRC Press, pp 37, 353-361 Dewick, P.M. (2002) Medicinal natural products: a biosynthetic approach, Wiley, pp 170, 171, 192, 204, 208, 210, 212 Hanson, J.R. (1968) The tetracyclic diterpenes, Pergamon, Volume 9, pp 114-120 Manitto, P. (1981) Biosynthesis of Natural Products, Ellis Horwood Limited, pp 258-262 Nakanishi, K. (1974) Natural products chemistry, Academic Press, Inc., Volume 1, pp 186-188, 218-230, 267-270 Newman, A.A. (1972) Chemistry of Terpenes and Terpenoids, Academic Press, pp 155- 191 Panico, R., Powell, W.H. and Richer, J.C. (1993) International Union of Pure and Applied Chemistry, Organic Chemistry Division, Commission of Nomenclature of Organic Chemistry, A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), Blackwell Scientific publications, pp 55-56 Rigandy, J. and Klesney, S.P. (1979) International Union of Pure and Applied Chemistry, Organic Chemistry Division, Commission of Nomenclature of Organic Chemistry, Nomenclature of Organic Chemistry, Sections A-H, Pergamon Press, pp 491-511 Templeton, W. (1969) An introduction to the chemistry of the terpenoids and steroids, Butterworths, pp 111-121 14
Page 1 and 2: UNIVERSITY OF KWAZULU-NATAL FACULTY
Page 3 and 4: Preface The experimental work descr
Page 5 and 6: Acknowledgements First and foremost
Page 7 and 8: GC-MS - gas chromatography-mass spe
Page 9 and 10: Table 19: NMR data of compound III
Page 11 and 12: Spectrum 1d: Expanded DEPT spectrum
Page 13 and 14: Compound V, stigmasterol 217 Spectr
Page 15 and 16: 2 19 1 4 18 O 20 5 Structures of co
Page 17 and 18: 3.4 Results and Discussion of the c
Page 19 and 20: compounds are also classified as tr
Page 21 and 22: 1 H CO2H 19 20 CHO 18 10 5 H 12 14
Page 23 and 24: may be referred to as a norabietane
Page 25 and 26: In the mevalonic acid pathway, the
Page 27 and 28: N thiamine diphosphate (TPP) O OH N
Page 29: in the kauranes. From the kauranes,
Page 33 and 34: The flower colour varies among the
Page 35 and 36: Clade 1 unplaced groups Group A: Pl
Page 37 and 38: different medical conditions and in
Page 39 and 40: Plectranthus species Skin condition
Page 41 and 42: Plectranthus species Heart, circula
Page 43 and 44: Use of the minimum inhibitory conce
Page 45 and 46: Plectranthus species Coleus kiliman
Page 47 and 48: Plectranthus species Extraction med
Page 49 and 50: Plectranthus species Coleus kiliman
Page 51 and 52: Methanol, ethanol and water seem to
Page 53 and 54: Plectranthus species P. amboinicus
Page 55 and 56: Plectranthus species P. amboinicus
Page 57 and 58: variation is observed within ring B
Page 59 and 60: Compound Name Synonym 39 40 41 42 4
Page 61 and 62: compounds (Table 6b). Depending on
Page 63 and 64: Table 6c: Royleanone-type abietanes
Page 65 and 66: R 1 R2CH2 19 O H 3CCO 19 O H 6 12 O
Page 67 and 68: Compound Name Synonym 81 82 83 84 8
Page 69 and 70: Compound Name Synonym 104 105 106 1
Page 71 and 72: R 1 19 3 3 1 18 1 18 20 20 O H O H
Page 73 and 74: educed furan ring. The linear side
Page 75 and 76: Compound Name Synonym HCO O 128 129
Page 77 and 78: Thirty-six compounds (131-167) havi
Page 79 and 80: Compound Name Synonym 147 148 HO HO
Page 81 and 82:
In compounds 149-165 (Table 9b), an
Page 83 and 84:
Compound Name Synonym 163 164 165 R
Page 85 and 86:
Table 9c: Coleon-type abietanes wit
Page 87 and 88:
1 18 3 20 4 O 5 19 R 1 R2 11 9 10 A
Page 89 and 90:
The majority of the abietanes isola
Page 91 and 92:
Plectranthus species Plant part Com
Page 93 and 94:
The leaves seem to be the most freq
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
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 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°
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
Page 236 and 237:
HO 218
Page 238 and 239:
HO 220
Page 240 and 241:
222
Page 242 and 243:
225
Page 244 and 245:
227
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