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R 2 HO 5 11 9 HO 9 H O O H C 7 O 11 13 13 OH O 7 14 O 15 16 17 R HO O H 9 O O 11 13 5 7 OH (118) R (119) H (120) OC(O)CH3 2 COCH 2 19 (123) R = OC OH O O (124) R = OC OH OH (125) R = OC OH OH 5 (130) 11 9 O 7 O 13 OCH 3 RCH 2 19 OH OH 5 OH 11 9 O 7 R 13 3 HO 5 11 9 O 7 13 14 15 R (121) H (122) OC(O)CH3 59 OH (126) R = OC(O)CH=(CH 3) 2 O (127) R = OC OH (128) R = O OC OH O OH (129) R = OC OH OCH 3
Thirty-six compounds (131-167) having a coleon-type structure were isolated from eleven Plectranthus and ten Coleus species, where most of the compounds have been isolated from P. edulis and C. coerulescens (Table 9a-c). The coleon-type compounds differ from the royleanones in that ring C is aromatic in coleon-type compounds as apposed to having a hydroxybenzoquinone or p-quinoid ring system. Compounds 131-148 (Table 9a) differ in ring B with regard to positions 6 and 7 as they both could be saturated as in 131, or oxidized, with either a hydroxy or carbonyl group (132-135) or two carbonyl groups (136-145). Alternatively either C-6 or C-7 could be oxidized as in 132-134. Compounds 138 to 141 are the only compounds where the methyl group/s at C-15 have been oxidized to an alcohol or acetyl group, while 134 is the only compound where the methyl group at C-20 has been oxidized to an alcohol. Plectranthol B (131), has an aromatic substituent at C-19 with a prenyl group occurring at C-12. In compounds 146 to 148, an oxygen bridge is formed between C-20 and either C- 6 or C-7. Compound 147 has a methoxy group present at C-20 while 148 has a carbonyl function at C-7. Table 9a: Coleon-type abietanes isolated from Plectranthus and Coleus species Compound Name Synonym 131 132 133 134 135 Continued on next page…. 12-O-(3-methyl-2-butenoyl)- 19-O-(3,4dihydroxybenzoyl)-11hydroxy-8,11,13-abietatriene7α,11-dihydroxy-12- methoxy-8,11,13-abietatriene 11,12-dihydroxy-8,11,13abietatriene-7-one 11,12,20-trihydroxy-8,11,13abietatriene-7-one 6β,11,12,14-tetrahydroxy- 8,11,13-abietatriene-7-one Isolated from Plectranthus (P) or Coleus (C) species Plectranthol B P. nummularius 11,20dihydroxysugiol 11hydroxysugiol 5,6dihydrocoleon U Reference Narukawa et al. 2001 P. elegans Dellar et al., 1996 P. cyaneus P. cyaneus; C. forskohlii P. argentatus Horvath et al., 2004 Horvath et al., 2004; Lingling et al., 2005 Alder et al., 1984a 60
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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
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 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: Compound Name Synonym HCO O 128 129
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
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Position Moiety Compound I 3 CH2 5
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Table 18: 13 C NMR data for compoun
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The equatorial methyl group at C-4,
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The proton NMR data for compound II
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Position 6 7 Compound III (400MHz)
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3.4.3 Structure elucidation of Comp
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showed HMBC correlations to another
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H HO 3 OH H 2 4 24 eq 1 23 5 ax Hax
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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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