university of kwazulu-natal faculty of science and agriculture school ...

More documents

Recommendations

Info

Compound Name Synonym 65 66 67 68 69 19 18 OH O 11 15 OCCH3 20 1 10 13 14 O 16 H 17(1516)abeo-3α,18diacetoxy-6β,7α,12,16tetrahydroxy-8,12- abietadiene-11,14-dione 3β-acetoxy-6β,7α,12trihydroxy-17(15→16),18(4→3)bisabeo-abieta- 4(18),8,12,16-tetraene- OH 11,14-dione 17(1516),19α(43)bisabeo-6β,7α,12trihydroxy-4(18),8,12,16- abietatetraene-11,14-dione 17(1516),19β(43)bisabeo-6β,7α,12,16tetrahydroxy-4(18),8,12- abietatriene-11,14-dione 17(1516),19β(43)bisabeo-6β,12,16trihydroxy-7α-methoxy- 4(18),8,12-abietatriene- 11,14-dione O R 1 1 20 O H 19 18 17(1516),19(43)bisabeo-6β,7α,16trihydroxyroyleanone 17(1516),19(43)bisabeo-6β,16-dihydroxy- 7α-methoxyroyleanone 10 6 R 2 OH 11 13 14 OH (54) R1 R2 (55) H H (56) H OH (57) OCH(O) OH 15 O 16 Isolated from Plectranthus (P) or Coleus (C) species R 1O CH 2 19 4 O H 11 OH 7 OH 13 14 O OR 2 R1 R2 (58) CH(O) H (59) H C2H5 47 Reference C. coerulescens Grob et al., 1978 P. grandidentatus Gaspar-Marques et al., 2006 P. edulis Kunzle et al., 1987 C. coerulescens Grob et al., 1978 15 16
R 1 R2CH2 19 O H 3CCO 19 O H 6 12 OH 14 8 O R1 R2 (60) H H (61) OCH(O) H (62) H OH (63) H OCH(O) 3 1 4 18 O H 10 6 7 OH OH 12 16 OH O 15 19 O OH 1 O H 3 7 20 O OH 17 16 O OCCH 3 O H 3CCO 3 H3CCOH2C 18 O (64) (65) 1 O H 6 7 OH OH OR 1 (66) R1 R2 (67) H CH2CH=CH2 (68) H CH2CH(OH)CH3 (69) CH3 CH2CH(OH)CH3 18 Thirty-eight compounds 70-108, commonly referred to as spirocoleons were isolated from P. edulis (eleven compounds), C. garckeanus (nine compounds), P. lanuginosus and C. coerulescens (seven compounds), C. barbatus (three compounds), P. grandis and C. somaliensis (two compounds) and P. barbatus (one compound) (Table 7). These compounds are refered to as spirocoleons as C-13 is the common carbon atom which links the cyclopropyl ring to the coleon-type abietane. The cyclopropyl bridge is represented as being either in the α or β position with the methyl group at C-15 being oriented such that the molecule is either R or S with respect to C-15. In compounds 71- 82, R1 to R4 have either hydrogen, acetyl or formyloxy groups. The difference between 72 and 83 is the orientation/stereochemistry of the methyl group at C-15. Oxidised R 2 1 20 O H 12 6 7 OH OH OH 48 O 16 OH
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 and 30: in the kauranes. From the kauranes,
Page 31 and 32: References Abad, A., Agullo, C., Cu
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: Table 6c: Royleanone-type abietanes
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
show all

university of kwazulu-natal faculty of science and agriculture school ...

Create successful ePaper yourself

Delete template?

Save as template?