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Plectranthus species Plant part P. nummularis acetone lv Compound Other Activity Reference Antioxidant activity (124), (128), (131), (168) Antifeedant activity antioxidant activity P. aff. puberulentus acetone lv (168), (169) antifeedent activity against S. littoralis P. barbatus ether lv insect antifeedent (90) activity against S. gramium and P. gossypiella P. forsteri ‘marginatus’ acetone lv P. puberulentus (44) (170) antifeedent activity against S. littoralis Antimalarial activity P. ecklonii dichloromethane lv (123), (124) P. hadiensis dichloromethane lv (38), (36) P. lucidus P. purpuratus subsp. purpuratus P. purpuratus subsp. tongaensis dichloromethane lv (123), (126) (126) (127), (128) P. barbatus water lv (169) Other activity P. ecklonii ethyl acetate w (123), (124) P. grandis hexane lv (70), (87) P. hereroensis acetone rt (64) antimalarial activity; inhibits β-haematin formation antimalarial activity; inhibits β-haematin formation antimalarial activity; inhibits β-haematin formation antisecretory and antiulcer activities inhibits tyrosinase activity gastroprotective properties, in mice antiviral activity against Herpes virus ie. Herpes simplex type II Narukawa et al., 2001 Wellsow et al., 2006 Kubo et al., 1984 Wellsow et al., 2006 van Zyl et al., 2008 van Zyl et al., 2008 van Zyl et al., 2008 Schultz et al., 2007 Nyila et al., 2009 Rodrigues et al., 2010 Batista et al., 1995 NB. Coleus species are also included in this table because of the uncertain relationship to the Plectranthus species Key: lv: leaves, rt: roots, s: stems, a: aerial parts, w: whole plant, f: flowers, NS: not specified 77
Table 14 contains six abietanes isolated from five known Salvia species, one unknown Salvia species and one Lepechinia species. These compounds have been shown to possess anticancer, antioxidant or cardiovascular activity with compounds 27 (royleanone) having antitumor and antioxidant activity and 28 (horminone) having antitumor, anticancer and antioxidant activity. The royleanone-type abietanes (27, 28, 32 and 44) have shown to exhibit anticancer, antioxidant and cardiovascular activity while the coleon-type compounds (134 and 146) have proved to be active only against cancer cell lines. Table 14: Pharmacological activity of abietanes isolated from other plant species Plant species Compound Activity Reference Salvia pachyphylla (146) Active against human cancer cell lines Guerrero et al., 2006 Salvia hypargeia (134) Active against ovarian cancer cell line (A2780) Topcu et al., 2008 *Salvia species (27), (28), (32) Antitumor Topcu and Goren, 2007 Lepechinia bullata (28), (43) Anticancer Jonathan et al., 1989 Kolak et al., 2001; Salvia amplexicaulis Cardiovascular activity Ulubelen et al., Salvia amplexicaulis; Salvia eriophora (44) Antihypertensive 2003 Kolak et al., 2001; Ulubelen et al., 2002 Salvia barrelieri (27), (28), (31) Antioxidant activity Kabouche et al., 2007 * unknown species The distinguishing feature of an abietanoid structure which determines the activity of the compound, is the oxidation pattern within ring B and ring C. It has been observed that the oxidation patterns at C-6, C-7 and C-12 influence the activity of the abietanoid. Compounds having a coleon-type structure (where ring C is aromatic) have proven to be more active than royleanone-type compounds (where ring C has a 12-hydroxy-p- benzoquinone moeity) (Gaspar-Marques et al., 2006; Wellsow et al., 2006). 78
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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
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: The leaves seem to be the most freq
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
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Position Compound IV 4.1 4.2 4.3 b
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multiplet at δH 1.91 (H-21) and a
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1 H Position Compound VI Burns et a
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Ultraviolet spectrum (λ max): 192n
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References Ansell, S.M. (1989) The
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Laing, M.D., Drewes, S.E. and Gurla
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van Vuuren, S. (2007) The antimicro
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Since the 7α-isomers of compounds
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eing incubated for 24 hours at 37°
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This indicated that the dihydroxy c
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acetic acid and air drying the plat
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whereas GI50 values for the renal a
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Table 28: Growth inhibition values
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Gaspar-Marques, C., Duarte, M.A., S
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Chapter 5 Conclusion The aim of thi
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References Abdel-Mogib, M., Albar,
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Table of Contents Page Compound I,
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Compound II, 6β,7β-dihydroxyroyle
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Compound IV, euscaphic acid HO HO 2
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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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