GC-MS (70eV, direct inlet), relative intensity %: m/z 426 (8.56) [M - COOH - OH] + , m/z 218 (100) 1 H NMR <strong>and</strong> 13 C NMR data (CD3OD, 600MHz): Refer to table 22 on page 124 Compound V: Chemical name: 5,22-Stigmastadien-3β-ol Common name: Stigmasterol Molecular formula: C29H42O Physical description: white residue Melting point: 168 o C (165 o C, Jamal et al., 2009) Optical rotation: [ ] 20 α D -40.8° (c 0.12g/100ml, CDCl3) Infrared spectrum ν KBr max cm-1 : 3305 cm -1 (O-H stretching b<strong>and</strong>s), 2932 cm -1 (C-H stretching vibrations), 1641 cm -1 (alkene stretching b<strong>and</strong>s) 1 H NMR <strong>and</strong> 13 C NMR data: Refer to table 25 on page 130 Compound VI: Chemical name: lup-20(29)-en-3β-ol Common name: Lupeol Molecular formula: C30H50O Physical description: white residue/powder Melting point: 214 o C (213 o C, Fotie et al., 2006; 214-215 o C, Saeed et al., 2003) Optical rotation: [ ] 20 α D +25.3° (c 1.2g/100ml, DCM) (lit. value = +25.7° (c 0.70, CHCl3), Fotie et al., 2006) Infrared spectrum ν KBr max cm-1 : 3332 cm -1 (O-H stretching b<strong>and</strong>s), 2941 cm -1 (C-H stretching vibrations), 1637 cm -1 (alkene stretching b<strong>and</strong>s) 1 H NMR <strong>and</strong> 13 C NMR data: Refer to table 26 on pages 131 135
References Ansell, S.M. (1989) The diterpenes <strong>of</strong> the genus Erythroxylum P. Browne, University <strong>of</strong> Natal, PhD Thesis, pp. 37-43, 247-248, 250-251 Begum, S., Hassan, S.I., Siddiqui, B.S., Shaheen, F., Ghayur, M.N. <strong>and</strong> Gilani, A.H. (2002) Triterpenoids from the leaves <strong>of</strong> Psidium guajava, Phytochemistry, 61, 399- 403 Burns, D., Reynolds, W.F., Buchanan, G., Reese, P.B. <strong>and</strong> Enriquez, R.G (2000) Assignment <strong>of</strong> 1 H <strong>and</strong> 13 C NMR spectra <strong>and</strong> investigation <strong>of</strong> hindered side-chain rotation in lupeol derivatives, Magnetic Resonance in Chemistry, 38, 488-493 Cerqueira, F., Cordeira-Da-Silva, A., Gaspar-Marques, C., Simoes, F., Pinto, M.M.M. <strong>and</strong> Nascimento, M.S.J. (2004) Effect <strong>of</strong> abietane diterpenes from Plectranthus gr<strong>and</strong>identatus on T- <strong>and</strong> B-lymphocyte proliferation, Bioorganic <strong>and</strong> Medicinal Chemistry, 12, 217-223 Chang C., Tseng M. <strong>and</strong> Kuo Y., (2005), Five new diterpenoids from the bark <strong>of</strong> Taiwania cryptomerioides, Chemical <strong>and</strong> Pharmaceutical Bulletin, 53, 286 Ci<strong>of</strong>fi, G., Bellino, A., Pizza, C., Venturella, F. <strong>and</strong> De Tommasi, N. (2001) Triterpene saponins from Tupidanthus calyptratus, Journal <strong>of</strong> Natural Products, 64, 750-753 Codd L. E. (1985) Flora <strong>of</strong> Southern Africa, South Africa Department <strong>of</strong> Agriculture, Volume 28, pp 137-172 D’Abrosca, B., Fiorentino, A., Monaco, P., Oriano, P. <strong>and</strong> Pacifico, S. (2006) Annurcoic acid: A new antioxidant ursane triterpene from fruits <strong>of</strong> cv. Annurca apple, Food Chemistry, 98, 285-290 Da Graca Rocha, G., Simoes, M., Lucio, K.A., Oliveira, R.R., Kaplan, M.A.C. <strong>and</strong> Gattass, C.R. (2007) Natural triterpenoids from Cecropia lyratiloba are cytotoxic to both sensitive <strong>and</strong> multidrug resistant leukemia cell lines, Bioorganic <strong>and</strong> Medicinal Chemistry, 15, 7355-7360 Delgado, G., Hern<strong>and</strong>ez, J. <strong>and</strong> Pereda-Mir<strong>and</strong>a, R. (1989) Triterpenoid acids from Cunila lythrifolia, Phytochemistry, 28, 1483-1485 Fang, J-M., Wang, K-C. <strong>and</strong> Cheng, Y-S. (1991) Steroids <strong>and</strong> triterpenoids from Rosa laevigata, Phytochemistry, 30, 3383-3387 136
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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,
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Cos, P., Hermans, N., de Bryne, T.,
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- 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
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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