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Two compounds, 7α-acetoxy-6β-hydroxyroyleanone (36) and coleon U (149) have shown to have the widest range of biological activity with compound 149 always being more active than compound 36 and occasionally having even stronger activity than the well known drugs used as controls. Although much has been done on testing the abietanes for biological activity, there are still many abietanes which have not been tested for any biological or pharmacological activity. These assays will prove useful in determining the structure-activity relationships of the abietanes. 79
References Abdel-Mogib, M., Albar, H.A. and Batterjee, S.M. (2002) Chemistry of the genus Plectranthus, Molecules, 7, 271-301 Alder, A.C., Ruedi, P. and Eugster, C. H. (1984a) Glandular pigments from labiates: polar diterpenoids from Plectranthus argentatus S. T. Blake, Helvetica Chimica Acta, 67, 1523-1530 Alder, A.C., Ruedi, P. and Eugster, C. H. (1984b) Glandular pigments from tropical labiates: parviflorones from Plectranthus strigosus Benth, Helvetica Chimica Acta, 67, 1531-1534 Almeida, F.C.G. and Lemonica, I.P. (2000) The toxic effects of Coleus barbatus B. on the different periods of pregnancy in rats, Journal of Ethnopharmacology, 73, 53-60 Alsufyani, T., Fatani, A., Khorshedm, F., Shaker, S. and Albar, H.A.H., Phytochemical composition and antimicrobial activities of the essential oil from Plectranthus tenuiflorus growing in Saudi Arabia, 9 pp, http://www.kau.edu.sa (accessed on 27/09/2010) Arihara, S., Ruedi, P. and Eugster, C. H. (1977) Diterpenoid leaf-gland pigments: coleons S and T from Plectranthus caninus Roth (Labiatae), a new diosphenol-trans- A/B-6,7-diketone pair of the abietane series, Helvetica Chimica Acta, 60, 1443-1447 Ascensao, L., Figueiredo, A.C., Barroso, J.G., Pedro, L.G., Schripsema, J., Deans, S.G. and Scheffer, J.J.C. (1998) Plectranthus madagascariensis: morphology of the glandular trichomes, essential oil composition and it’s biological activity, International Journal of Plant Science, 159, 31-38 Ayyanar, M and Ignacimuthu, S. (2005) Traditional knowledge of the Kani tribals of Kouthalai of Tirunelveli Hills, Tamil Nadu, India, Journal of Ethnopharmacology, 102, 246-255 Batista, O., Duarte, A., Nascimento, J. and Simoes, M.F. (1994) Structure and antimicrobial activity of diterpenes from the roots of Plectranthus hereroensis, Journal of Natural Products, 57, 858-861 80
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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
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: Table 14 contains six abietanes iso
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
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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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227
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