Supplementary Data
Uptake and degradation of trimethylamine by Euphorbia milii
Dian Siswanto a,b, Yanvary Chhon a and Paitip Thiravetyan a,*
a School of Bioresources and Technology, King Mongkut’s University of Technology Thonburi, Bangkok 10150, Thailand
b Faculty of Mathematics and Natural Sciences, Brawijaya University, Malang 65145, Indonesia
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*Corresponding author; Tel. 66-2-470-7535, Fax: 66-2-452-3455.
E-mail address: (P. Thiravetyan).
Table S1 Summarize metabolic compounds found in E. milii under non-treatment (control) and TMA treatment conditions
Metabolic compounds / %Similarity / %
of total / Metabolic compounds / %
Similarity / %
of total /
4 h : Control (non-treatment) / 4 h of TMA Treatment
Leaves / Leaves
1,2,3-Benzenetriol / 94 / 47.95 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 50 / 1.10
Hexadecanamide / 76 / 10.39 / 4-Vinylphenol / 72 / 0.86
9-Octadecenamide, (Z)- / 94 / 41.66 / Benzocyclooctene, 6,8-dimethyl- / 90 / 1.41
1,2,3-Benzenetriol / 91 / 57.41
1,8-Octanediamine, N,N'-dimethyl- / 38 / 2.32
Butanoic acid, 3-[(Phenylmethyl)amino]-, (R)- / 38 / 1.07
1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid / 58 / 8.57
n-Hexadecanoic acid / 95 / 1.75
Hexadecanamide / 74 / 3.29
9-Octadecenamide, (Z)- / 98 / 20.74
Octadecanamide / 80 / 1.48
Stems / Stems
2-Propanone, 1,3-dihydroxy- / 78 / 2.78 / 2-Propanone, 1,3-dihydroxy- / 83 / 5.11
1,3-Cyclopentanedione / 50 / 1.21 / (3-Methyl-2-oxiranyl) methanol / 38 / 0.60
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 81 / 1.26 / 2,3-Dihydro-3,5-dihydroxy-6-methyl / 58 / 1.18
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 91 / 3.47 / 2(3H)-Furanone, 5-ethyldihydro- / 46 / 0.27
2-Butanone, 4-hydroxy-3-methyl- / 18 / 2.50 / 1H-Imidazole-4-carboxamide, 5-amino- / 43 / 3.00
1-Cyclopentene-1-methanol, .alpha. –ethyl- / 43 / 2.85 / Pentanal / 59 / 0.66
1,2,3-Propanetriol, monoacetate / 32 / 4.37 / Ethanamine, N-ethyl-N-nitroso / 42 / 1.22
d-Mannitol, 1,4-anhydro- / 37 / 3.72 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 95 / 8.26
1,1,3,3-Tetramethylguanidin / 35 / 4.09 / 2,6,6-Trideuterio-2-dimethylaminocyclohexanone / 41 / 1.47
Propanoic acid, 2-methyl-, hexyl ester / 59 / 5.00 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 93 / 6.51
Carbamic acid ethyl ester / 43 / 10.85 / 1,2,3-Propanetriol, monoacetate / 47 / 3.62
Butanoic acid, 3-(methoxymethylamino)-3-methyl-, methyl ester / 47 / 8.87 / 1-Hexanamine / 14 / 0.90
3-Deoxy-d-mannoic lactone / 87 / 29.58 / 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one / 38 / 3.26
Hexadecanamide / 87 / 4.64 / 2-Propanol, 1-amino- / 35 / 1.80
9-Octadecenamide, (Z) - / 93 / 13.74 / Tetradecane / 22 / 3.12
9-Octadecenamide / 93 / 1.06 / 1,2,3-Benzenetriol / 46 / 2.20
1,4-Dimethyl-2,5-piperazinedione / 38 / 1.64
N-Propylacetamide / 50 / 2.03
Pentadeuterio-2-acetyl-1pyrroline / 52 / 10.08
N-Methoxymethyl-N-methylacetamide / 43 / 33.66
Hexadecanoic Acid / 72 / 0.40
Hexadecanamide / 91 / 1.11
9-Octadecenamide, (Z)- / 98 / 7.43
Octadecanamide / 95 / 0.47
Roots / Roots
2-Propanone, 1,3-dihydroxy- / 43 / 2.34 / Isothiazolo[3,4-E]-2,1,3-benzothiadiazole, 4-methyl- / 38 / 3.15
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 70 / 0.71 / Ethanamine, 2-propoxy- / 47 / 1.50
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 90 / 1.16 / Urea, trimethyl / 42 / 1.15
4-Vinylphenol / 59 / 0.27 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 94 / 5.32
Propanoic acid, 2-methyl-, hexyl ester / 35 / 3.11 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 94 / 8.68
Propane, 2-(ethenyloxy)- / 43 / 6.18 / Hexanoic acid, 3-hydroxy-5-methyl-, methyl ester / 37 / 2.32
Dihydroxymaleic acid / 22 / 7.57 / Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid / 47 / 1.11
3-Deoxy-d-mannoic lactone / 68 / 47.07 / N-(2-methoxycarbonylethylidene)-N'-dimethylhydrazine- / 38 / 2.33
Hexadecanoic acid / 95 / 6.61 / Butanal, dimethylhydrazone / 35 / 2.97
Hexadecanamide / 94 / 3.09 / 2-Propenamide / 38 / 1.69
Benzoic acid, 2-[4-(1,1-dimethylethyl) phenoxy]- / 59 / 1.57 / 1,2,3-Benzenetriol / 91 / 4.00
9-Octadecenamide, (Z)- / 99 / 14.8 / 1-Methyl-4-nitro-1H-pyrazol-5-amine / 35 / 1.90
5-Androstene, 4,4-dimethyl- / 38 / 2.36 / 1,6-Anhydro-2,4-dideoxy-.beta.-D-ribo-hexopyranose / 58 / 10.00
Octadecanamide / 90 / 1.65 / Undecanoic acid / 52 / 4.71
5-Chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid / 22 / 1.52 / 2R,3S-9-[1,3,4-Trihydroxy-2-butoxymethyl] guanine / 50 / 7.62
3-Deoxy-d-mannoic lactone / 93 / 18.49
n-Hexadecanoic acid / 80 / 1.60
Hexadecanamide / 90 / 2.90
Benzoic acid, 2-[4-(1,1-dimethylethyl)phenoxy]- / 59 / 1.67
9-Octadecenamide, (Z)- / 98 / 13.03
4,4a,5,9-Tetrahydro-4a,8-dimethyl-5,9-dioxoazuleno[6,5-B]furan-3-carboxylic acid methyl ester / 86 / 2.30
Octadecanamide / 83 / 1.59
48 h : Control (non-treatment) / 48 h of TMA Treatment
Leaves / Leaves
2-cyclohexen-1-one, 3,5,5-trimethyl- / 87 / 4.12 / Benzeneacetaldehyde / 64 / 2.15
1,2,3-benzenetriol / 93 / 22.78 / 2-Cyclohexen-1-one, 3,5,5-trimethyl- / 70 / 1.16
Hexadecanamide / 76 / 13.38 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 76 / 1.81
9-octadecenamide, (Z)- / 98 / 59.71 / 4-Vinylphenol / 72 / 1.04
Propanoic acid, 2-methyl-, 2-methylpropyl ester / 45 / 1.70
1,2,3-Benzenetriol / 83 / 24.67
2,2'-(Methylimino)diethanol / 46 / 3.48
Urea, N-methyl-N-nitroso- / 46 / 18.66
n-Hexadecanoic acid / 97 / 3.43
Hexadecanamide / 94 / 5.53
9-Octadecenamide, (Z)- / 98 / 33.26
Octadecanamide / 43 / 3.12
Stems / Stems
2-Propanone, 1,3-dihydroxy- / 78 / 3.98 / 2-Furanmethanol / 92 / 11.57
Butane-1,4-D2 / 64 / 1.59 / 2-Propanone, 1,3-dihydroxy- / 78 / 2.85
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 81 / 1.69 / Benzeneacetaldehyde / 43 / 0.52
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 90 / 3.19 / 1,3,5-Triazine-2,4,6-triamine / 38 / 1.31
3,4-Furandiol, tetrahydro-, trans- / 25 / 2.02 / n-Methylethanolamine / 42 / 0.61
6-Acetyl-.beta.-d-mannose / 37 / 3.13 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 94 / 5.51
Butanoic acid, 2,2-diacetyl-3-oxo-, ethyl ester / 37 / 4.29 / Thiazole / 27 / 1.17
Bacchotricuneatin C / 43 / 3.44 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 89 / 3.80
Propanoic acid, 2-methyl-, hexyl ester / 50 / 5.42 / 1,2,3-Propanetriol, monoacetate / 45 / 3.69
Pentadeuterio-2-acetyl-1-pyrroline / 38 / 11.00 / N-(2-Methoxycarbonylethylidene)-N'-dimethylhydrazine / 52 / 3.15
2-Hexanone, 1,1,3,3,5-pentadeutero-5-methyl-4-oxa- / 50 / 37.57 / Butanamide, N,N,2,3-tetramethyl- / 49 / 4.47
Hexadecanamide / 95 / 2.73 / Nicotinic acid-D1-.alpha.,.alpha.'-D2 / 83 / 2.04
9-Octadecenamide, (Z)- / 99 / 18.49 / 1-Hexanamine, 2-ethyl-N-(2-ethylhexyl)- / 30 / 1.46
Octadecanamide / 90 / 1.46 / 1-Octanamine- / 38 / 2.07
L-Alanine, N-Acetyl- / 38 / 10.32
2-Deoxypentopyranose / 46 / 33.90
n-Hexadecanoic Acid / 92 / 3.66
Hexadecanamide / 94 / 0.97
9-Octadecenamide, (Z)- / 98 / 6.44
Tetradecanamide / 50 / 0.48
Roots / Roots
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 81 / 2.30 / 2-Propanone, 1,3-dihydroxy- / 40 / 1.68
Propanoic acid, 2-methyl-, hexyl ester / 43 / 6.58 / Urea, N-methyl-N-nitroso- / 50 / 1.11
Carbamic acid,ethyl ester / 47 / 30.56 / 2-Cyclohexen-1-one, 3,5,5-trimethyl- / 81 / 0.95
Hexadecanamide / 76 / 10.13 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 93 / 1.26
Benzoic acid, 2-[4-(1,1-dimethylethyl) phenoxy]- / 64 / 7.10 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 92 / 2.53
N-(4,4-Dideuterio-4-phenyl-butyl) phthalimide / 25 / 1.68 / 2-Propanol, 1-amino- / 14 / 1.50
9-Octadecenamide, (Z)- / 98 / 25.33 / 1,1,3,3-Tetramethylguanidin / 43 / 1.34
5-Androstene, 4,4-dimethyl- / 90 / 12.27 / 1-Nonanamine / 22 / 5.44
5-Chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid / 38 / 4.04 / 1-Nitro-2-acetamido-1,2-dideoxy-d-monnitol / 43 / 13.87
Urea / 35 / 43.92
n-Hexadecanoic acid / 96 / 3.20
Hexadecanoic acid, ethyl ester / 99 / 5.11
Hexadecanamide / 72 / 2.73
Benzoic Acid, 2-[4-(1,1-dimethylethyl)phenoxy]- / 64 / 1.54
9-Octadecenamide, (Z)- / 98 / 9.53
4,4a,5,9-Tetrahydro-4a,8-dimethyl-5,9-dioxoazuleno[6,5-B]furan-3-Carboxylic acid methyl ester / 80 / 1.92
Octadecanamide / 50 / 1.24
Acetamide, 2-[6-cyclopropyl-3-cyano-4-(2furyl)-2-pyridylthio]- / 43 / 1.12
60 h : Control (non-treatment) / 60 h of TMA Treatment
Leaves / Leaves
1,2,3-Benzenetriol / 96 / 8.71 / Benzeneacetaldehyde / 80 / 4.23
Hexadecanamide / 94 / 15.04 / 2-Cyclohexen-1-one, 3,5,5-trimethyl- / 76 / 4.99
9-Octadecenamide, (Z)- / 98 / 76.25 / 1,2,3-Benzenetriol / 55 / 12.65
Dimethylamine / 16 / 1.32
1,2-Ethanediol, diformate / 38 / 21.72
15-Tetramethylhexadec-2-en-1-ol / 70 / 2.82
Hexadecanamide / 74 / 7.51
9-Octadecenamide, (Z)- / 98 / 44.76
Stems / Stems
2-Propanone, 1,3-dihydroxy- / 64 / 2.07 / 2-Cyclohexen-1-one, 3,5,5-trimethyl- / 81 / 1.69
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 76 / 1.81 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 91 / 13.29
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 90 / 2.25 / Propanoic acid, 2-methyl-, butyl ester / 64 / 16.60
Butanoic acid, 2,2-diacetyl-3-oxo-, ethyl ester / 27 / 3.54 / 1-Hexanamine / 43 / 31.88
6-Acetyl-.beta.-d-mannose / 40 / 9.90 / 3-Deoxy-d-mannoic lactone / 90 / 7.85
d-Glycero-d-ido-heptose / 38 / 14.02 / 3-Hydroxy-N,N-dimethylpropanamide / 46 / 28.68
Propanoic acid, 2-methyl-, butyl ester / 47 / 50.90 / Tetradecanamide / 80 / 1.69
Gala-l-ido-octose / 47 / 3.17 / 9-Octadecenamide, (Z)- / 99 / 13.29
3-Deoxy-d-mannoic lactone / 58 / 11.33
Hexadecanamide / 95 / 1.02
9-Octadecenamide, (Z)- / 99 / 2.07
Octadecanamide / 92 / 1.81
Roots / Roots
2-Hydroxycyclopent-2-en-1-one / 43 / 0.01 / 2-Oxo-4-nitrosomethyl-6-trifluoro-methyl-1,2-dihydropyrimidine / 30 / 1.20
3-Ethoxy,3-(methylamino)-2-Propenoic acid methyl ester / 64 / 0.62 / 2-Cyclohexen-1-one, 3,5,5-trimethyl- / 70 / 0.84
2-Cyclohexen-1-one, 3,5,5-trimethyl- / 42 / 0.49 / 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 90 / 1.71
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- / 94 / 1.42 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 78 / 1.35
1,2-Benzenediol / 44 / 1.35 / Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester / 27 / 0.59
2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 64 / 1.95 / N-Hydroxymethylacetamide / 47 / 1.63
Alpha.-Hydroperoxy diethyl ether / 38 / 2.34 / 1-Nitro-2-acetamido-1,2-dideoxy-d-monnitol / 38 / 11.44
N-(2-Methoxycarbonylethylidene)-N'-dimethylhydrazine / 16 / 1.70 / 3-Deoxy-d-Mannoic lactone / 49 / 53.65
1,2,3-Benzenetriol / 70 / 9.08 / n-Hexadecanoic Acid / 95 / 3.87
Carbamic acid, ethyl ester / 27 / 13.37 / Hexadecanamide / 87 / 3.56
3-Deoxy-d-mannoic lactone / 74 / 59.97 / Phenanthrene, 1,2,3,4,4a,9,10,10a octahydro-1,1,4a-trimethyl-7-(1-methylethyl)-, (4as-rans)- / 50 / 1.55
Tetradecanamide / 86 / 1.49 / 9-Octadecenamide, (Z)- / 99 / 14.23
Phenanthrene, 1,2,3,4,4a,9,10,10a octahydro-1,1,4a-trimethyl-7-(1-methylethyl)-, (4as-trans)- / 50 / 0.59 / 4,4a,5,9-Tetrahydro-4a,8-dimethyl-5,9-dioxoazuleno[6,5-B]furan-3-carboxylic acid methyl ester / 72 / 1.73
9-Octadecenamide, (Z)- / 96 / 4.08 / Octadecanamide / 64 / 1.43
4H-1-Benzopyran-4-one, 3-hydroxy-2-(phenyl-D5)- / 38 / 1.05 / Benzaldehyde, 2-nitro-, diaminomethylidenhydrazon / 30 / 1.22
Pregnane-3,17,20-triol / 25 / 0.48
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