Chemistry of the Genus Plectranthus
Abstract
:Introduction
Diterpenoids
Diterpenoids isolated from Plectranthus
Essential oils
Long-chain alkylphenols
Long-chain alkylphenols
Miscellaneous constituents
Miscellaneous constituents
Conclusions
Plectranthus species | Isolated chemical constituents | References |
---|---|---|
Abyssinian P. sp. | D1, D5, D9, D10, D12-D14, D21, D30 | 37 |
P. albidus | L1-L8, L10-L12 | 28 |
P. aliciae | ─── | 62 |
P. alloplectus | ─── | 63 |
P. ambiguus | D141-D146, flavonoid M10 | 33 |
P. amboinicus | Essential oil | 19 |
P. argentatus | D4, D5, D8, D21, D25, D101, D102, D112 | 38 |
P. asirensis | ─── | 13 |
P. australis | ─── | 64 |
P. barbatus | D29, D65, D75, D76, D115, D117 | 39 |
D65 | 16 | |
P. burorum | ─── | 65 |
P. caninus | D108, D109 | 40 |
D59-D64 | 86 | |
P. ciliatus | ─── | 61 |
P. coesta | D148 | 41 |
D147 | 42 | |
P. coetsa | ─── | 66 |
P. coetsoides | D147, D149-D154 | 43 |
P. coleoides | Essential oil | 25 |
P. cyrpiculoides | ─── | 67 |
P. defoliatus | Essential oil | 26 |
P. ecklonii | D86, M12-M15 | 68 |
P. edulis | D17, D18, D21, D22, D23, D24, D38-D48, D50, D55, D56, D66, D67, D69, D70, D94-D100, D106, D107, D118, D119, D137, D138 | 44 |
D118 | 45 | |
P. elegans | D93, D120 | 46 |
P. esculentus | ─── | 69 |
P. fasciculatos | ─── | 70 |
P. floribundus | ─── | 11 |
P. fruticosus | Essential oil | 20 |
P. gandicalyx | ─── | 65 |
P. garckeanus | ─── | 65 |
P. geradianus | ─── | 71 |
P. glandulosus | Essential oil | 23 |
P. glaucocalyx | An antimicrobial diterpenoid | 47 |
P. grandidentatus | D68, D101, D102, D128-D134 | 48 |
D5, D11 | 49 | |
P. gratus | ─── | 63 |
P. hadiensis | ─── | 67 |
P. hereroensis | D9, D35, D36 | 50 |
D37 | 51 | |
D9, D16 | 52 | |
Sesquiterpene M1 | 30 | |
P. hilliardiae | ─── | 61 |
P. incanus (= P. mollis) | Essential oil | 27, 79 |
Fatty acids | 35 | |
P. inflexus | ─── | 72 |
P. japonicus | D155 | 53 |
Caffeic acid derivative | 36 | |
P. japonicus var. glaucocalyx | ─── | 77 |
P. kapatensis | ─── | 65 |
P. lanuginosus | D17, D30-D34, D45, D47, D52-D54, D57, D58, D67, D71, D74, D88-D90, D100, D103, D110, D111 | 54 |
P. lucidus | ─── | 62 |
P. madagascariensis | Essential oil | 24 |
P. malvinus | ─── | 62 |
P. marrubioides | Flavonoid M11 | 34 |
P. melissoides | ─── | 79 |
P. mollis (= P. incanus) | ─── | 79 |
P. mollis | ─── | 79 |
P. myrianthus | D128 | 48 |
D2, D4, D96, D98, D101 | 87 | |
P. neochilus | ─── | 73 |
P. nilgherricus | D82, D83, D139, D140 | 88 |
P. oribiensis | ─── | 61 |
P. ornatus | ─── | 74 |
P. parviflorus | D77, D82-D86 | 55 |
P. pentheri | ─── | 62 |
P. porpeodon | ─── | 65 |
P. pseudobarbatus | ─── | 65 |
P. puberulentus | ─── | 65 |
P. purpuratus | D72, D73, D77, D79, D91, D92, D121, D122, D140 | 56 |
P. purpuratus subsp. montanus | ─── | 62 |
P. purpuratus subsp. tongaensis | ─── | 62 |
P. reflexus | ─── | 61 |
P. rugosus | Essential oil | 18 |
Triterpenoids M2-M6 & β-sitosterol | 31, 32 | |
Triterpenoids M7-M9, β-sitosterol & hexacosanol | 85 | |
P. saccatus subsp. pondoensis | ─── | 62 |
P. saccatus var. longitubus | ─── | 61 |
P. sanguineus | D3, D4-D7, D9, D15, D21, D25, D26, D68, D99, D102, D128-D131, D139 | 57 |
P. schimperi | ─── | 65 |
P. sp. from the borders of Lake Kiwu, Rwanda | D19-D21, D27-D29, D49, D51, D75, D76, D104, D105, D113-D116, D123-D127D123-D126 | 58 |
59 | ||
P. spectabilis | ─── | 63 |
P. stenophyllus | ─── | 75 |
P. stocksii | ─── | 79 |
P. strigosus | D77, D78, D82-D87 | 60 |
P. sylvestris | L9, L13-L18 | 29 |
P. tenuiflorus | Essential oil | 21,22 |
P. vestitus | Essential oil | 76 |
P. vettiveroides | ─── | 78 |
P. zatarhendi | ─── | 67 |
P. zatarhendi var. tomentosus | ─── | 67 |
P. zuluensis | ─── | 61 |
Diterp. | Name of diterpenoid | Diterp. | Name of diterpenoid |
---|---|---|---|
D1 | Royleanone | D79 | (11-Hydroxy-19-isovaleroyloxy-5,7,9(11),13-abietatetraen-12-one) |
D2 | 6β, 7α-Dihydroxy-royleanone | D80 | Fuerstione |
D3 | 7-O-Formylhorminone | D81 | 3β-Acetoxyfuerstione |
D4 | 6β-Hydroxy-7α-formyloxyroyleanone | D82 | Parviflorone C |
D5 | 6β-Hydroxy-7α-acetoxyroyleanone | D83 | Parviflorone E |
D6 | 6β-Hydroxyroyleanone | D84 | Parviflorone B |
D7 | 5,6-Dihydrocoleone U | D85 | Parviflorone D |
D8 | 6β-Formyloxy-7α-hydroxyroyleanone | D86 | Parviflorone F |
D9 | Horminone | D87 | Parviflorone G |
D10 | 7α-Acetoxyroyleanone | D88 | Lanugone M |
D11 | 6β-Hydroxy-7α-acyloxyroyleanone | D89 | Lanugone L |
D12 | Taxoquinone (= 7β-Hydroxyroyleanone) | D90 | Lanugone N |
D13 | 7-Oxoroyleanone | D91 | 6α,11-Dihydroxy-19-isovaleroyloxy-7, 9(11), 13-abietatrien-12-one |
D14 | 8α,9α-Epoxy-7-oxoroyleanone | D92 | 6α,11-Dihydroxy-19-senecioyloxy-7,9(11), 13-abietatrien-12-one |
D15 | 6β,7α-Dihydroxy(allyl)royleanone | D93 | 11-Hydroxy-12-oxo-7,9(11),13-abietatriene |
D16 | 7α,12-Dihydroxy-17(15°16)-abeo-abieta-8,12,16-trien-11,14-dione | D94 | (2'ξ,3aR,10bR)-8-(2'-Acetoxy-1'-methyl-ethyl)-3,3a-dihydro-7,9,10-trihydroxy-3a, 10b-dimethyl-1H-phenanthro[10,1bc]-furan-4(2H),6(10bH)-dione |
D17 | Lanugone A | D95 | 16-O-Acetylcoleon C |
D18 | (4bS,7R,8aR)-7-Formyloxy-4b,5,6,7,8,8a-hexahydro-3-hydroxy-4b,8,8-trimethyl-2-(2-propenyl)phenanthren-1,4-dione | D96 | Coleon U |
D19 | Plectranthone F | D97 | Coleon C |
D20 | Plectranthone G | D98 | |
D21 | 6β,7α-Dihydroxyroyleanone | D99 | 16-O-Acetylcoleon D |
D22 | (4bS,7R,8aR,9S,10S)-7-Formyloxy-4b,5,6, 7,8,8a,9,10-octahydro-3,9,10-trihydroxy-4b, 8,8-trimethyl-2-(2-propenyl)-phenanthren-1,4-dione | D100 | (15S)-Coleon D |
D23 | (4bS,7R,8aS,9S,10S)-4b,5,6,7,8,8a,9,10-Octahydro-3,9,10-trihydroxy-4b,7-dimethyl-8-methyliden-2-(2-propenyl)-phenanthren-1,4-dione | D101 | Coleon V |
D24 | (2'ξ,4bS,7R,8aS,9S,10S)-4b,5,6,7,8,8a,9, 10-Octahydro-3,9,10-trihydroxy-2-(2'-hydroxypropyl)-4b,7-dimethyl-8-meth-ylidenphenanthren-1,4-dione | D102 | Coleon U |
D25 | Coleon-U-quinone | D103 | (15S)-Coleon C |
D26 | 8α,9α-Epoxy-8,9-dihydrocoleon-U-quinone | D104 | (15S)-2α-Acetoxycoleon C |
D27 | Plectranthone H | D105 | (15S)-Coleon H |
D28 | Plectranthone I | D106 | (2'ξ,4aS,10aS)-1,2,3,4,4a,10a-Hexahydro-5,6,8-trihydroxy-7-(2'-hydroxypropyl)-1,1,4a-trimethylphenanthren-9,10-dione |
D29 | Plectranthone J | D107 | (2'ξ,4aR)-2,3,4,4a-Tetrahydro-5,6,8,10-tetrahydroxy-7-(2'-hydroxypropyl)-1,1,4a-trimethylphenanthren-9(1H)-one |
D30 | 6,7-Didehydroroyleanone | D108 | Coleon T |
D31 | Lanugone B | D109 | Coleon S |
D32 | Lanugone C | D110 | Lanugone R |
D33 | Lanugone D | D111 | Lanugone S |
D34 | Lanugone E | D112 | 5,6-Dihydrocoleon U |
D35 | 3β-Acetoxy-6β,7α,12-trihydroxy-17-(15°16);18(4°3)-bisabeo-abieta-4(19), 8.12,16-tetraen-11,14-dione | D113 | (15S)-2α-Acetoxycoleon D |
D36 | 16-Acetoxyhorminone | D114 | (15S)-Coleon I |
D37 | 16-Acetoxy-7α,12-dihydroxy-8,12-abieta-dien-11,14-dione | D115 | Plectrinone B |
D38 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-3',10'-Diacetoxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-9'-hydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D116 | (16S)-Plectrinone A |
D39 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-3'- Acetoxy,10'-formyloxy-4'b,5',6',7',8',8'a,9',10'-octahydro-9'-hydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D117 | (16R)-Plectrinone A |
D40 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-10'-Acetoxy-4'b,5',6',7',8',8'a,9',10'-octahydro-3',9'-dihydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D118 | Edulone A |
D41 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-3'- Acetoxy-4'b,5',6',7',8',8'a,9',10'-octahydro-9',10'-dihydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D119 | (1'S,10bS)-7,9,10-Trihydroxy-8-(2'-hydroxy-1'-methylethyl)-3,10b-dimethyl-1H-benzo[g]cyclopenta[de][1]benzopyran-4(2H),6(10bH)-dione |
D42 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-10'-Formyloxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-3',9'-dihydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D120 | 7α,11-Dihydroxy-12-methoxy-8,11,13-abietatriene |
D43 | (2R,2'S,3'R,4'bS,7'R,8'aS,9'S,10'S)-4'b,5', 6',7',8',8'a,9',10'-Octahydro-3',9',10'-tri-hydroxy-2,4'b,7'-trimethyl-8'-methyliden-spiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D121 | 11,12-Dihydroxy-19-isovaleroyloxy-8,11,13-abietatrien-7-one |
D44 | (2R,2'S,3'R,4'bS,7'R,8'aR,9'S,10'S)-9-Acetoxy-7'-formyloxy-4'b,5',6',7',8',8'a, 9',10'-octahydro-3',10'-dihydroxy-2,4'b, 8',8'-tetramethylspiro[cyclopropan-1,2' (1'H)-phenanthren]-1',4'(3'H)-dione | D122 | 11,12-Dihydroxy-19-senecioyloxy-8,11,13-abietatrien-7-one |
D45 | Lanugon G | D123 | Plectranthone B |
D46 | (2R,2'S,3'R,4'bS,7'R,8'aR,9'S)-7'-Formyl-oxy-4'b,5',6',7',8',8'a,9',10'-octahydro-3',9'-dihydroxy-2,4'b,8',8'-tetramethylspiro-[cyclopropan-1,2'(1'H)-phenanthren]-1',4' (3'H)-dione | D124 | Plectranthone A |
D47 | Lanugone F | D125 | Plectranthone C |
D48 | (2R,2'S,3'R,4'bS,7'R,8'aR,9'S,10'S)-7',10'-Bisformyloxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-3',9'-dihydroxy-2,4'b,8',8'-tetra-methylspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D126 | Plectranthone D |
D49 | Plectranthone K | D127 | Plectranthone E |
D50 | (2R,2'S,3'R,4'bS,7'ξ,8'aR,9'S,10'S)-7',10'-Diacetoxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-3',9'-dihydroxy-2,4'b,7'-trimethyl-8'-methylidenspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D128 | Grandidone A |
D51 | Plectranthone L | D129 | 7-Epigrandidone A |
D52 | Lanugone H | D130 | Grandidone B |
D53 | Lanugone I | D131 | 7-Epigrandidone B |
D54 | Lanugone J | D132 | Grandidone D |
D55 | (2S,2'S,3'R,4'bS,7'R,8'aR,9'S,10'S)-7-Formyloxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-3',9'-diacetoxy-10'-hydroxy-2,4'b,8', 8'-tetramethylspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D133 | 7-Epigrandidone D |
D56 | (2S,2'S,3'R,4'bS,7'R,8'aR,9'S,10'S)-7',10'-Bisformyloxy-4'b,5',6',7',8',8'a,9',10'-octa-hydro-3',9'-dihydroxy-2,4'b,8',8'-tetra-methylspiro[cyclopropan-1,2'(1'H)-phenanthren]-1',4'(3'H)-dione | D134 | Grandidone C |
D57 | Lanugone K | D135 | Nilgherron A |
D58 | Lanugone K' | D136 | Nilgherron B |
D59 | Coleon R | D137 | (3R)-6,9-Dihydroxy-3,4-dimethyl-7-(1-methylethyl)-3-(2-propenyl)naphtho[2,3-b]- furan-2-(3H),5,8-trione |
D60 | Coleon M | D138 | (2'ξ,3R)-7-(2'-Acetoxy-1'-methylethyl)-6,9-dihydroxy-3,4-dimethyl-3-(2''-propenyl)-naphtho[2,3-b]furan-2-(3H),5,8-trione |
D61 | 7,12-Diacetylcoleon J | D139 | Sanguinon A |
D62 | Coleon N | D140 | (16R)-17,19-Diacetoxy-16-hydroxy-13β-kauran-3-one |
D63 | Coleon Q | D141 | (16R)-2α-Senecioyloxy-3α-acetoxyphyllocladan-16,17-diol |
D64 | Coleon P | D142 | (16R)-2α-Senecioyloxy-3α,17-diacetoxy-16-hydroxyphyllocladane |
D65 | Plectrin | D143 | (16R)-2α-Isovaleroyloxy-3α-acetoxyphyllocladan-16,17-diol |
D66 | Coleon Z | D144 | (16R)-2α-Isovaleroyloxy-3α,17-diacetoxy-16-hydroxyphyllocladane |
D67 | (15S)-Lanugone O | D145 | (16R)-3α-Acetoxyphyllocladan-16,17-diol |
D68 | 14-Hydroxytaxodione | D146 | (16R)-2α-Senecioyloxy-16,17-dihydroxyphyllocladan-3-one |
D69 | (4bS,8aS)-2-(2-Acetoxypropyl)-4b,5,6,7,8, 8a-hexahydro-1,4-dihydroxy-4b,8,8-tri-methylphenanthren-3,9-dione | D147 | Plecostonol (= coetsidin A) |
D70 | (2'ξ,4bS,8aS)-4b,5,6,7,8,8a-Hexahydro-1,4-dihydroxy-2-(2'-hydroxypropyl)-4b,8,8-trimethylphenanthren-3,9-dione | D148 | Coestinol |
D71 | Lanugone P | D149 | Coetsidin B |
D72 | 19-Isovaleroyloxytaxodione | D150 | Coetsidin C |
D73 | 19-Senecioyloxytaxodione | D151 | Coetsidin D |
D74 | Lanugone Q | D152 | Coetsidin E |
D75 | Coleon F | D153 | Coetsidin F |
D76 | (16S)-Coleon E | D154 | Coetsidin G |
D77 | Parviflorone A (= 11-hydroxy-19-senecioyl-oxy-5,7,9(11),13-abietatetraen-12-one) | D155 | Rabdosin B |
D78 | Parviflorone H |
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Abdel-Mogib, M.; Albar, H.A.; Batterjee, S.M. Chemistry of the Genus Plectranthus. Molecules 2002, 7, 271-301. https://doi.org/10.3390/70200271
Abdel-Mogib M, Albar HA, Batterjee SM. Chemistry of the Genus Plectranthus. Molecules. 2002; 7(2):271-301. https://doi.org/10.3390/70200271
Chicago/Turabian StyleAbdel-Mogib, M., H. A. Albar, and S. M. Batterjee. 2002. "Chemistry of the Genus Plectranthus" Molecules 7, no. 2: 271-301. https://doi.org/10.3390/70200271
APA StyleAbdel-Mogib, M., Albar, H. A., & Batterjee, S. M. (2002). Chemistry of the Genus Plectranthus. Molecules, 7(2), 271-301. https://doi.org/10.3390/70200271