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H 3 R 1CH 2 1 20 O H OR 2 R 4 6 7 13 OR 3 O H 15 CH2R5 17 R1 R2 R3 R4 R5 (100) H C(O)CH3 H β-OH OC(O)CH3 (101) OC(O)CH3 C(O)CH3 H α- H (102) OC(O)CH3 H C(O)CH3 OC(O)CH3 α-OH H (103) OC(O)CH3 H C(O)CH3 β-OH H 19 H 3CCO O 3 1 18 20 O H 6 7 OH OH OR R (106) H (107) C(O)CH3 O H CH 3 19 3 1 18 RCH 2 20 O H 19 6 7 3 OH 1 20 OH O (108) O 6 7 OH O OCCH 3 H 18 OH O (104) R H (105) OC(O)CH3 O OCCH 3 Twenty-two quinone methides, 109-130 were isolated from ten Plectranthus species (Table 8). Eight compounds were isolated from P. strigosus and six from P. lanuginosus and P. parviflorus while the other species yielded less than four compounds each. Compounds 109-120 closely resemble benzoquinones, but there is only one carbonyl present in ring C, located at C-12 instead of C-11 and C-14 and has double bonds at ∆ 7 , C-9(11) and ∆ 13 . Compounds 121-130 have an additional double bond in ring B at ∆ 5 . Yet again variation of the isopropyl group at C-13 is observed in compounds 109-117. In compound 118 the isopropyl group has cyclised onto ring C, resulting in a partially H CH 3 55 H CH 3
educed furan ring. The linear side chains which have replaced the isopropyl group are either saturated as in 112, oxidized to a double bond as in compound 116 or contain methoxy groups (114) and hydroxy groups (111, 112, 115, 117, 119-122). The tertiary methyl group usually present at C-19, has been oxidized to a formyloxy (-OCHO) group in compounds 114 and 117. In abietanes 126-130 the methyl group at position 19 has been modified to include either an aromatic group as in 126-129 or a prenylated group as in 130. Compound 122 has an acetyl group present at C-3 as well as a hydroxy group at C-15 while compounds 123-125 have aromatic substituents at C-2. Continued on next page….. Table 8: Vinylogous quinones isolated from Plectranthus species Compound Name Synonym 109 110 111 112 113 114 115 116 11-hydroxy-7,9(11),13abietatriene-12-one11,14-dihydroxy-7,9(11),13abietatriene-6,12-dione 11,14,16-trihydroxy- 7,9(11),13-abietatriene-6,12dione 11,14,16-trihydroxy- 17(15→16)-abeoabieta- 7,9(11),13-triene-6,12-dione 16-acetoxy-11,14-dihydroxy- 17(15→16)-abeoabieta- 7,9(11),13-triene-6,12-dione 19-formyloxy-6β,11,14trihydroxy-16-methoxy- 17(15→16)-abeoabieta- 7,9(11),13-triene-12-one 6β,19-epoxy-11,14dihydroxy-13-(2hydroxypropyl)-7,9(11),13abietatriene-12-one13-allyl-6β,19-epoxy-11,14dihydroxy-7,9(11),13abietatriene-12-one 14hydroxytaxodione Lanugone O Lanugone N Lanugone L Lanugone M Isolated from Plectranthus (P) species Reference P. elegans Dellar et al., 1996 P. grandidentatus Uchida et al., 1981 P. lanuginosus; P. edulis Schmid et al., 1982; Kunzle et al., 1987 P. edulis Kunzle et al., 1987 56
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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
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 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: R 1 19 3 3 1 18 1 18 20 20 O H O H
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
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esonance showed HMBC correlations t
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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,
Page 179 and 180:
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
Page 236 and 237:
HO 218
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HO 220
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222
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225
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