Supplementary Data 1. Floral scent composition of species analyzed
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Supplementary Data 1. Floral scent composition of species analyzed in this study. Compounds belonging to the same chemical class are arranged according to retention times. S.colorata S.longicilia nigth night S.longicilia S.tridentata S.tridentata S.diclinis S.diclinis day night day night day S.giraldii S.giraldii S.frivaldszkyana S.frivaldszkyana night day night day Aromatic compounds 1, 4-Benzoquinone# 0.03 - - 1.82 0.26 - - - - - - Benzaldehyde# 79.21 - - 39.07 - - 18.68 - - - - Benzyl alcohol# 1.54 0.21 - - - - - - - - - Phenylacetaldehyde# 10.90 - - - - - 62.51 - - - - 2-Methoxyphenol# - - - 0.85 - - - - - - - Methyl benzoate# 1.27 - - - - - - 0.45 13.10 - - 2-Phenylethanol# 1.36 - - - - 100.00 18.22 - - 1.05 - - - - - - - - - - - - 0.04 - - - - - - - - - - *p-Methoxystyrene # *2-Phenylpropenal N - 46.30 22.72 - - - - - - 2.06 - 0.12 - - - - - - - - - - 1-Phenyl-1,2-propanedione# 0.43 - - 0.33 - - - - - - - Methyl salicylate# 1.44 - - - - - - - - - - 3-Phenylpropanol# 0.05 - - - - - - - - - - - - - - - - 0.27 - - 0.06 - 0.71 - - - - - - - - - - - - - 0.45 - - - - - - - (Z)-Cinnamyl alcohol# - - - - - - - - - - - (E)-Cinnamaldehyde# 0.67 - - - - - - - - - - (E)-Cinnamyl alcohol# 0.89 - - - - - - - - - - - - - - - - - - - - - Benzyl acetate# 3-Phenylpropanal N 2-Phenylethyl acetate# *p-Methoxybenzaldehyde# *Hydroquinone N1 Methyl o-methoxybenzoate# S.colorata S.longicilia nigth night - *Benzyl butyrateA S.longicilia S.tridentata S.tridentata S.diclinis S.diclinis day night day night day - S.giraldii S.giraldii S.frivaldszkyana S.frivaldszkyana night day night day - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 3-Phenylpropyl acetateN - - - - - - - - - - - Methyleugenol# - - - - - - - - - - - 0.04 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0.69 - - - - - - - 2-MethylbutylaldoximeMS - - - - - - - - - 20.21 - 3-Methylbutylaldoxime# - - - - - - - - - 0.40 - *1-NitropentaneN3 - - - - - - - - - 72.14 - *Methyl nicotinateN 0.14 - - - - - - - - - - *Phenylacetonitrile# - - - - - - - - - 0.50 - *NonanenitrileN - - - - - - - - - - - *2-Aminobenzaldehyde# - - - - - - - - - - - (E)+(Z)-Phenylacetaldoxime# - - - - - - - - - 1.35 - - - - - - - - - - - - *Eugenol# 3,4-Dimethoxystyrene# *4-Methoxyphenethyl alcohol N *Vanillin# Isoamyl benzoateA (E)-Cinnamyl acetate A *(Z)-Methyl isoeugenol A *3,4-Dimethoxybenzaldehyde *(E)-Methyl isoeugenol N A (Z)-3-Hexenyl benzoate N2 *3,4,5-Trimethoxybenzaldehyde Benzyl benzoate# N N-containing compounds N *Decanenitrile S.colorata S.longicilia nigth night - Indole# S.longicilia S.tridentata S.tridentata S.diclinis S.diclinis day night day night day - S.giraldii S.giraldii S.frivaldszkyana S.frivaldszkyana night day night day 0.01 - - - - - - - - - - 0.22 0.55 - - - - - - - - - - - *Prenyl acetate# - - - - - - - - - 0.04 - Camphene# - 0.59 - - 17.43 - - 14.09 - - 56.95 - 2.12 - - 55.97 - - 65.54 - - - - 0.67 - - 26.34 - - 18.58 - - 42.50 - - - - - - - - - - - (Z)-β-Ocimene# - 0.82 - - - - - - - - - (E)-β-Ocimene# - 46.36 29.82 55.44 - - - 0.61 63.57 1.18 - (Z)-Arbusculone# - 0.09 5.61 - - - - - - - - (E)-Arbusculone# - - - - - - - - - - - Linalool# - - - - - - - - - - - *Allo-/neoallo-ocimeneA - - - - - - - - - - - (E)-Ocimene oxide# - 0.13 - - - - - - - - - Lilac aldehyde A# - 0.24 17.19 - - - - - - - - 4-Oxoisophorone# 0.09 - - - - - - - - - - Lilac aldehyde B+C# - 0.14 18.01 - - - - - - - - Lilac aldehyde D# - <0.01 6.66 - - - - - - - - (Z)+(E)-Linalool oxide pyranoid# - - - - - - - - - - - Lilac alcohol A# - - - - - - - - - - - Lilac alcohol B+C# - - - - - - - - - - - Lilac alcohol D# - - - - - - - - - - - *Geraniol# - - - - - - - - - - - *1-Nitro-2-phenylethane# *2-(Dimethylamino)benzaldehyde MS Terpenoids Sabinene A β-Pinene# α-Phellandrene A S.colorata S.longicilia nigth night 0.07 Lilac alcohol formate AMS S.longicilia S.tridentata S.tridentata S.diclinis S.diclinis day night day night day - S.giraldii S.giraldii S.frivaldszkyana S.frivaldszkyana night day night day - Lilac alcohol formate B+CMS - 0.02 - - - - - - - - - *Geranyl acetate# - - - - - - - - - - - - - - - - - - - 2.20 - - *Longifolene# - - - - - - - - - - - Germacrene D# - - - - - - - - 2.13 - - (E,E)-α-Farnesene# β-Bourbonene A - - - - - - - - - - - N4 *β-Selinene - - - - - - - 0.73 19.01 - - (E)-Nerolidol# - - - - - - - - - - - *CubenolA - - - - - - - - - - - *Farnesol/al isomerA - - - - - - - - - - - - - - - - - - - - - - m/z 54, 55, 84, 39, 41, 64KI<900 - - - - - - - - - 0.78 - m/z 81,79,43,109,53,77KI1098 - - - - - - - - - - - - - - - - - - - - - - Spiroacetal *2-Ethyl-1,6 dioxaspiro[4.4]nonaneMS Unknown compounds m/z 124, 151, 81, 95, 165, 53KI1185 0.07 - - 1.35 - - - - - - - m/z 93, 43, 55, 81, 111, 67 KI1244 - - - - - - - - - - - m/z 43, 71, 39, 55, 83, 107 KI1349 m/z 91, 43, 65, 162, 119, 145 KI1212 - - - - - - - - - - - m/z 91, 150, 39, 107, 79, 135 KI1428 - 0.14 - - - - - - - - - m/z 91, 39, 161, 204, 105, 79 KI1487 - - - - - - - - - - - m/z 43, 108, 58, 93, 123, 67KI1704 S.colorata S.longicilia nigth night - S.longicilia S.tridentata S.tridentata S.diclinis S.diclinis day night day night day - S.giraldii S.giraldii S.frivaldszkyana S.frivaldszkyana night day night day - Other unknowns$ 0.997 2.1018 - - - - 0.322 - - - - ng/g of dry flower weight * min 156 315 1 22 39 1 74 154 6 26 1 3 3 3 3 3 2 2 2 2 3 N *: compunds so far undescribed for Sileneae. #: authentic standards were available for identification. $: unknowns < 1% in any species/time period were pooled with the upperscript digit giving the number of pooled compounds. N,A: compounds were identified based on ms data and comparison of Kovats retention index (KI) data provided by Adams (A)or NIST (N) (deviation of in the maximum ± 10). N1: the KI of present work (1266) differed by 25 from the KI provided by NIST (1241). N2: the KI of present work (1582) differed by 16 from the KI provided by Adams (1566). N3: the KI of present work (900) differed by 25 from the KI provided by NIST (925). N4: the KI of present work (1511) differed by 21 from the KI provided by Adams (1490). MS: Identification of compounds was based on ms data (see also Methods and Materials). 3 S.boryi night S.boryi day S.uniflora S.uniflora S.zawadzkii S.zawadzkii S.variegata S.variegata night day night day night day S.saxatilis night S.saxatilis day S. flavescens night 1, 4-Benzoquinone# - - - - - - - - - - - Benzaldehyde# - - 80.88 - - - - - - - 98.47 Benzyl alcohol# 7.81 - - - - - - - - - - Phenylacetaldehyde# - - - - - - - - - - - 2-Methoxyphenol# - - - - - - - - - - - Methyl benzoate# - - - - - - - - 1.11 - - 2-Phenylethanol# - - 0.22 - - - 1.21 - - - - - - - - - - - - - - - Aromatic compounds *p-Methoxystyrene # - - - - - - - - - - - 5.95 - - - - - - - - 0.29 - 3-PhenylpropanalN - - - - - - - - - - - 1-Phenyl-1,2-propanedione# - - 0.25 - - - - - - - 0.03 Methyl salicylate# - - 4.27 - - - - - 1.99 - - 3-Phenylpropanol# - - - - - - - - - - - 2-Phenylethyl acetate# - - - - - - - - - - - *p-Methoxybenzaldehyde# - - - - - - - - - - - - - - - - - - - - - - (Z)-Cinnamyl alcohol# - - - - - - - - - - - (E)-Cinnamaldehyde# - - - - - - - - - - - (E)-Cinnamyl alcohol# - - - - - - - - - - - Methyl o-methoxybenzoate# - - 0.03 - - - - - - - - *Benzyl butyrateA - - - - - - - - - - - *Eugenol# - - - - - - - - - - - 3,4-Dimethoxystyrene# - - - - - - - - - - - *2-Phenylpropenal N Benzyl acetate# *Hydroquinone N1 S.boryi night - S.boryi day - S.saxatilis night - S.saxatilis day - S. flavescens night - 0.03 - - - - - - Methyleugenol# - - - - - - - - - - - - - - - *Vanillin# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0.27 - - - - - - - - 2-MethylbutylaldoximeMS - - - - - - - - - - - 3-Methylbutylaldoxime# 2.57 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - *Phenylacetonitrile# - - - - - - - - - - - *NonanenitrileN - - - - - - - - - - - *2-Aminobenzaldehyde# - - - - - - - - - - - (E)+(Z)-Phenylacetaldoxime# - - - - - - - - - - - - - - - - - - - - - - 0.74 - - - - - - - - - - *1-Nitro-2-phenylethane# - - - - - - - - - - - *2-(Dimethylamino)benzaldehydeMS - - - - - - - - - - - *4-Methoxyphenethyl alcoholN 3-Phenylpropyl acetateN Isoamyl benzoateA (E)-Cinnamyl acetate A *(Z)-Methyl isoeugenol A *3,4-Dimethoxybenzaldehyde N *(E)-Methyl isoeugenolA (Z)-3-Hexenyl benzoate N2 *3,4,5-Trimethoxybenzaldehyde N Benzyl benzoate# S.uniflora S.uniflora S.zawadzkii S.zawadzkii S.variegata S.variegata night day night day night day 0.05 - N-bearing compounds *1-Nitropentane N3 *Methyl nicotinate N N *Decanenitrile Indole# S.boryi night S.boryi day S.uniflora S.uniflora S.zawadzkii S.zawadzkii S.variegata S.variegata night day night day night day S.saxatilis night S.saxatilis day S. flavescens night 0.05 - - - - - - - - - - - - - - 37.57 - - - - - - - 8.01 18.62 - 10.22 - - 54.09 - 69.55 - - - - 77.47 - - - 22.49 - 17.83 - - - - - - - - - - - - (Z)-β-Ocimene# - - - - - - - - - - - (E)-β-Ocimene# 80.71 66.75 - 22.53 - - 0.84 1.06 95.69 1.62 1.32 (Z)-Arbusculone# - - 5.54 - 5.04 16.84 8.14 0.59 - - - (E)-Arbusculone# - - 1.17 - - - 10.48 0.74 - - - Terpenoids *Prenyl acetate# Camphene# Sabinene A β-Pinene# α-Phellandrene A - - - - 1.01 - - - - - - *Allo-/neoallo-ocimene 0.04 - - - - - - - 0.02 - - (E)-Ocimene oxide# 0.24 - - - - - - - 0.47 0.34 0.02 Lilac aldehyde A# - - 0.14 - 17.98 42.72 14.57 0.25 - - - 4-Oxoisophorone# - - - - - - - - - - - Lilac aldehyde B+C# - - 1.41 - 21.97 3.17 31.25 0.81 - - - Lilac aldehyde D# - - 0.58 - 7.64 14.52 14.41 0.70 - - - (Z)+(E)-Linalool oxide pyranoid# - - - - - - - - - - - Lilac alcohol A# - - 0.10 - 2.21 4.34 0.58 - - - - Lilac alcohol B+C# - - 0.33 - 4.79 7.28 0.73 0.28 - - - Lilac alcohol D# - - 0.06 - 0.44 2.56 0.84 0.13 - - - - - 0.10 - - - 0.79 - - - - - - - - - - - - - - - - - - - - - - - - - - 0.28 - - - - - - - - - - Linalool# A *Geraniol# Lilac alcohol formate A MS Lilac alcohol formate B+CMS *Geranyl acetate# β-BourboneneA S.boryi night - S.boryi day - *Longifolene# - - - - - - - Germacrene D# - - - - - - - 0.03 - - - - - *β-SelineneN4 - - - - - (E)-Nerolidol# 0.06 - - - - - - 0.21 - - - - m/z 124, 151, 81, 95, 165, 53KI1185 KI1212 (E,E)-α-Farnesene# *Cubenol A *Farnesol/al isomer A S.uniflora S.uniflora S.zawadzkii S.zawadzkii S.variegata S.variegata night day night day night day - S.saxatilis night - S.saxatilis day - S. flavescens night - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 3.52 - - 2.19 2.55 - - - - - - - - - - - - - - - 0.07 - - - - - - - 0.14 Spiroacetal *2-Ethyl-1,6 dioxaspiro[4.4]nonaneMS Unknown compounds m/z 54, 55, 84, 39, 41, 64KI<900 m/z 81,79,43,109,53,77 KI1098 - - m/z 93, 43, 55, 81, 111, 67 KI1244 - - - - - 1.44 0.83 - - - - m/z 43, 71, 39, 55, 83, 107 KI1349 - - 0.36 - 1.36 4.95 3.43 0.14 - - - 0.11 3.71 - - - - - - 0.3 0.14 <0.01 - - - - - - - - - - - m/z 91, 43, 65, 162, 119, 145 m/z 91, 150, 39, 107, 79, 135KI1428 m/z 91, 39, 161, 204, 105, 79 m/z 43, 108, 58, 93, 123, 67 Other unknowns KI1487 KI1704 $ ng/g of dry flower weight * min - 29.54 - - - - - - - - - 1.189 - 0.691 - - - 1.283 0.11 0.433 0.021 0.024 114 2 113 12 4 5 15 6 51 88 703 N 1 1 2 2 1 1 2 2 1 1 $ *: compunds so far undescribed for Sileneae. #: authentic standards were available for identification. : unknowns < 1% in any species/time period were pooled with the upperscript digit giving the number of pooled compounds. N,A: compounds were identified based on ms data and comparison of Kovats retention index (KI) data provided by Adams (A)or NIST (N) (deviation of in the maximum ± 10). N1: the KI of present work (1266) differed by 25 from the KI provided by NIST (1241). N2: the KI of present work 1 (1582) differed by 16 from the KI provided by Adams (1566). N3: the KI of present work (900) differed by 25 from the KI provided by NIST (925). N4: the KI of present work (1511) differed by 21 from the KI provided by Adams (1490). MS: Identification of compounds was based on ms data (see also Methods and Materials). S.aegyptiaca night S.aegyptiaca day S.linicola night S.linicola day S.fraudatrix night S.fraudatrix day S.fuscata night S.fuscata day S.littorea night S.littorea day 1, 4-Benzoquinone# - - - - - - - 0.19 - - Benzaldehyde# - - - - - - - - 63.59 - Benzyl alcohol# - - - - - - - - 0.58 - Phenylacetaldehyde# - - - - - - - - - - 2-Methoxyphenol# - - - - - - - - - - Methyl benzoate# - - - - - - - - 0.02 - 2-Phenylethanol# - - - - - 1.96 - - 0.01 - - - - - - - - - 0.01 - - - - - - - - - - - Benzyl acetate# - - - 0.63 - - - - 35.72 - 3-PhenylpropanalN - - - - - - - - - - 1-Phenyl-1,2-propanedione# - - - - - - - - - - Methyl salicylate# - - - - - - - - - - 3-Phenylpropanol# - - - - - - - - - - 2-Phenylethyl acetate# - - - - - - - - - *p-Methoxybenzaldehyde# - - - - - - - - <0.01 - - - - - - - - - - - (Z)-Cinnamyl alcohol# - - - - - - - - - - (E)-Cinnamaldehyde# - - - - - - - - - - (E)-Cinnamyl alcohol# - - - - - - - - - - Methyl o-methoxybenzoate# - - - - - - - - - - *Benzyl butyrateA - - - - - - - - - - *Eugenol# - - - - - - - - 0.01 - 3,4-Dimethoxystyrene# - - - - - - - - 0.01 - Aromatic compounds *p-Methoxystyrene # *2-Phenylpropenal *Hydroquinone N N1 - S.aegyptiaca night - S.aegyptiaca day - S.linicola night - S.linicola day - S.fraudatrix night - S.fraudatrix day - S.fuscata night - S.fuscata day - S.littorea night - S.littorea day - 3-Phenylpropyl acetateN - - - - - - - Methyleugenol# - - - - - - - - - - - 0.01 - *Vanillin# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - <0.01 0.01 - - - - - - - - - - 0.01 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 2-MethylbutylaldoximeMS - - - - - - - - - - 3-Methylbutylaldoxime# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - *Phenylacetonitrile# - - - - - - - - - - *NonanenitrileN - - - - - - - - - - *2-Aminobenzaldehyde# - - - - - - - - - - (E)+(Z)-Phenylacetaldoxime# - - - - - - - - - - *Decanenitrile - - - - - - - - - - Indole# - - - - - - - - - - *1-Nitro-2-phenylethane# - - - - - - - - - - *2-(Dimethylamino)benzaldehydeMS - - - - - - - - - - *4-Methoxyphenethyl alcoholN Isoamyl benzoateA (E)-Cinnamyl acetate A *(Z)-Methyl isoeugenol A *3,4-Dimethoxybenzaldehyde N *(E)-Methyl isoeugenolA (Z)-3-Hexenyl benzoate N2 *3,4,5-Trimethoxybenzaldehyde N Benzyl benzoate# - N-containing compounds *1-Nitropentane N3 *Methyl nicotinate N N S.aegyptiaca night S.aegyptiaca day S.linicola night S.linicola day S.fraudatrix night S.fraudatrix day S.fuscata night S.fuscata day S.littorea night S.littorea day *Prenyl acetate# - - - - - - - - - - Camphene# - 16.13 - 15.20 - - - - - - - 53.38 - 47.90 - - - - - - - 19.34 - 22.72 - - - - - - - - - - - - - - - - (Z)-β-Ocimene# - - - 0.02 - - - - - - (E)-β-Ocimene# 99.18 10.32 100.00 12.99 - 96.41 96.33 75.80 0.01 100.00 (Z)-Arbusculone# - - - - - - - - - - (E)-Arbusculone# - - - - - - - - - - Terpenoids Sabinene A β-Pinene# α-Phellandrene A - - - - - - - - - - 0.10 - - - - - - - - - (E)-Ocimene oxide# - - - 0.08 100.00 1.64 - - - - Lilac aldehyde A# - - - - - - - - - - 4-Oxoisophorone# - - - - - - - - - - Lilac aldehyde B+C# - - - - - - - - - - Lilac aldehyde D# - - - - - - - - - - (Z)+(E)-Linalool oxide pyranoid# - - - - - - - - - - Lilac alcohol A# - - - - - - - - - - Lilac alcohol B+C# - - - - - - - - - - Lilac alcohol D# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - Lilac alcohol formate B+CMS - - - - - - - - - - *Geranyl acetate# - - - - - - - - - - Linalool# A *Allo-/neoallo-ocimene *Geraniol# Lilac alcohol formate A MS β-BourboneneA S.aegyptiaca night - S.aegyptiaca day - S.linicola night - S.linicola day - S.fraudatrix night - S.fraudatrix day - S.fuscata night - S.fuscata day - S.littorea night - S.littorea day - *Longifolene# - - - - - - 0.29 4.84 - - Germacrene D# - - - - - - - - - - (E,E)-α-Farnesene# - - - - - - - - - - *β-SelineneN4 - - - - - - - - - - (E)-Nerolidol# - - - - - - - - - - - - - - - - 0.29 - - - - - - - - - - - - - 0.57 0.15 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0.29 1.48 - - *Cubenol A *Farnesol/al isomer A Spiroacetal *2-Ethyl-1,6 dioxaspiro[4.4]nonaneMS Unknown compounds m/z 54, 55, 84, 39, 41, 64KI<900 m/z 81,79,43,109,53,77 KI1098 m/z 124, 151, 81, 95, 165, 53KI1185 0.05 0.69 - - - - - - - - m/z 93, 43, 55, 81, 111, 67 KI1244 - - - - - - - - - - m/z 43, 71, 39, 55, 83, 107 KI1349 - - - - - - - - - - m/z 91, 150, 39, 107, 79, 135KI1428 - - - - - - - - - - KI1487 - - - - - - 2.19 17.68 - - m/z 91, 43, 65, 162, 119, 145 m/z 91, 39, 161, 204, 105, 79 m/z 43, 108, 58, 93, 123, 67 Other unknowns KI1212 KI1704 $ ng/g of dry flower weight * min - - - - - - - - - - 0.091 - - 0.473 - - 0.611 - - - 10 20 <1 86 <1 4 18 1 3570 2 N 3 3 2 2 2 2 2 2 3 $ *: compunds so far undescribed for Sileneae. #: authentic standards were available for identification. : unknowns < 1% in any species/time period were pooled with the upperscript digit giving the number of pooled compounds. N,A: compounds were identified based on ms data and comparison of Kovats retention index (KI) data provided by Adams (A)or NIST (N) (deviation of in the maximum ± 10). N1: the KI of present work (1266) differed by 25 from the KI provided by NIST (1241). N2: the KI of present work 3 (1582) differed by 16 from the KI provided by Adams (1566). N3: the KI of present work (900) differed by 25 from the KI provided by NIST (925). N4: the KI of present work (1511) differed by 21 from the KI provided by Adams (1490). MS: Identification of compounds was based on ms data (see also Methods and Materials). S.cambessedesii night S.cambessedesii day S.psammitis night S.psammitis day S.scabriflora night S.scabriflora day S.fabaria night S.fabaria day - - - - - - 4.22 9.24 Benzaldehyde# 86.65 - 39.82 - - - - - Benzyl alcohol# 3.32 - 2.38 - - - - - Phenylacetaldehyde# - - - - - - - - 2-Methoxyphenol# - - - - - - - - Methyl benzoate# - - - - - - - - 2-Phenylethanol# 0.38 - 1.50 - - - - - 2.50 - - - - - - - - - - - - - - - - - - 0.40 - - - - 0.87 - - - - - - - 1-Phenyl-1,2-propanedione# - - - - - - - - Methyl salicylate# - - - - - - - - 3-Phenylpropanol# 1.61 - 0.25 - - - - - - - - - - - - - 0.19 - - - - - - - - - - - - - 2.16 2.64 (Z)-Cinnamyl alcohol# 0.11 - 0.32 - - - - - (E)-Cinnamaldehyde# 0.70 - 1.57 - - - - - (E)-Cinnamyl alcohol# 1.34 - 4.45 - - - - - - - - - - - - - 0.02 - - - - - - - - - - - - - - - 0.32 - - - - - - - Aromatic compounds 1, 4-Benzoquinone# *p-Methoxystyrene # *2-Phenylpropenal N Benzyl acetate# 3-PhenylpropanalN 2-Phenylethyl acetate# *p-Methoxybenzaldehyde# *Hydroquinone N1 Methyl o-methoxybenzoate# *Benzyl butyrateA *Eugenol# 3,4-Dimethoxystyrene# S.cambessedesii night - S.cambessedesii day - S.psammitis night - S.psammitis day - S.scabriflora night - S.scabriflora day - S.fabaria night - S.fabaria day - 3-Phenylpropyl acetateN - - - - - - - - Methyleugenol# - - - - - - - - *Vanillin# - - - - - - - - - - - - - - - - - - 0.18 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0.04 - - - - - 1.20 - - - - - - - 2-MethylbutylaldoximeMS - - 38.93 - - - - - 3-Methylbutylaldoxime# - - - - - - - - - - - - - - - - - - - - - - - - *Phenylacetonitrile# - - - - 3.46 - - - *NonanenitrileN - - 0.08 - - - - - *2-Aminobenzaldehyde# - - - 0.07 - - - - (E)+(Z)-Phenylacetaldoxime# - - - - 2.77 - - - *Decanenitrile - - 0.05 - - - - - Indole# - - - 2.40 - - - - *1-Nitro-2-phenylethane# - - - - 0.97 - - - *2-(Dimethylamino)benzaldehydeMS - - - 0.04 - - - - *4-Methoxyphenethyl alcoholN Isoamyl benzoateA (E)-Cinnamyl acetate A *(Z)-Methyl isoeugenol A *3,4-Dimethoxybenzaldehyde N *(E)-Methyl isoeugenolA (Z)-3-Hexenyl benzoate N2 *3,4,5-Trimethoxybenzaldehyde N Benzyl benzoate# N-containing compounds *1-Nitropentane N3 *Methyl nicotinate N N S.cambessedesii night S.cambessedesii day S.psammitis night S.psammitis day S.scabriflora night S.scabriflora day S.fabaria night S.fabaria day *Prenyl acetate# - - - - - - - - Camphene# - - - 15.37 - - - 87.24 - - - 78.30 - - - - - - - - - - - - - - - - - - - - (Z)-β-Ocimene# - - - - - - - - (E)-β-Ocimene# 0.56 100.00 1.52 3.31 90.18 59.98 1.54 0.88 (Z)-Arbusculone# - - - - - - - - (E)-Arbusculone# - - - - - - - - - - - - - 9.76 91.12 - *Allo-/neoallo-ocimene - - - - - - - - (E)-Ocimene oxide# - - - - - - - - Lilac aldehyde A# - - - - - - 0.01 - 4-Oxoisophorone# - - - - - - - - Lilac aldehyde B+C# - - - - - - 0.37 - Lilac aldehyde D# - - - - - - 0.37 - (Z)+(E)-Linalool oxide pyranoid# - - - - 1.71 18.91 - - Lilac alcohol A# - - - - - - - - Lilac alcohol B+C# - - - - - - 0.06 - Lilac alcohol D# - - - - - - 0.05 - - - - - - - - - - - - - - - - - Lilac alcohol formate B+CMS - - - - - - - - *Geranyl acetate# - - - - - - - - Terpenoids Sabinene A β-Pinene# α-Phellandrene A Linalool# A *Geraniol# Lilac alcohol formate A MS β-BourboneneA S.cambessedesii night - S.cambessedesii day - S.psammitis night - S.psammitis day - S.scabriflora night - S.scabriflora day 1.63 S.fabaria night - S.fabaria day - *Longifolene# - - - - - - - - Germacrene D# - - - - - - - - 0.22 - 0.16 - - - - - *β-SelineneN4 - - - - - 8.50 - - (E)-Nerolidol# - - - - - - 0.10 - - - - - - - - - - - - - - - - - - - - - - - - - - - 8.29 - - - - - - - - - - - - - m/z 124, 151, 81, 95, 165, 53KI1185 - - - - - - - - KI1212 (E,E)-α-Farnesene# *Cubenol A *Farnesol/al isomer A Spiroacetal *2-Ethyl-1,6 dioxaspiro[4.4]nonaneMS Unknown compounds m/z 54, 55, 84, 39, 41, 64KI<900 m/z 81,79,43,109,53,77 KI1098 - - - - - - - - KI1244 - - - - - - - - KI1349 - - - - - - - - m/z 91, 150, 39, 107, 79, 135KI1428 - - - - - - - - KI1487 - - - - - - - - - - - - - - - - - - 0.441 0.111 0.91 1.232 - - 433 2 39 21 3 1 9 3 m/z 91, 43, 65, 162, 119, 145 m/z 93, 43, 55, 81, 111, 67 m/z 43, 71, 39, 55, 83, 107 m/z 91, 39, 161, 204, 105, 79 m/z 43, 108, 58, 93, 123, 67 Other unknowns KI1704 $ ng/g of dry flower weight * min N 3 3 3 3 3 3 3 3 $ *: compunds so far undescribed for Sileneae. #: authentic standards were available for identification. : unknowns < 1% in any species/time period were pooled with the upperscript digit giving the number of pooled compounds. N,A: compounds were identified based on ms data and comparison of Kovats retention index (KI) data provided by Adams (A)or NIST (N) (deviation of in the maximum ± 10). N1: the KI of present work (1266) differed by 25 from the KI provided by NIST (1241). N2: the KI of present work (1582) differed by 16 from the KI provided by Adams (1566). N3: the KI of present work (900) differed by 25 from the KI provided by NIST (925). N4: the KI of present work (1511) differed by 21 from the KI provided by Adams (1490). MS: Identification of compounds was based on ms data (see also Methods and Materials). S.fabarioides night S.fabarioides day S.holzmannii night L.coronaria night L.coronaria day S.tatarica night S.tatarica day 1, 4-Benzoquinone# - - - - - - 17.46 Benzaldehyde# - - - - - - - Benzyl alcohol# - - - - - 5.48 - Phenylacetaldehyde# - - - - - - - 2-Methoxyphenol# - - - - - - - Methyl benzoate# - - - - - - - 2-Phenylethanol# - - - 100.00 62.50 - 2.11 - - - - - - - - - - - - - - Benzyl acetate# - - - - - - - 3-PhenylpropanalN - - - - - - - 1-Phenyl-1,2-propanedione# - - - - - - - Methyl salicylate# - - - - - - - 3-Phenylpropanol# - - - - - - - 2-Phenylethyl acetate# - - - - - - - *p-Methoxybenzaldehyde# - - - - - - - - - - - - - - (Z)-Cinnamyl alcohol# - - - - - - - (E)-Cinnamaldehyde# - - - - - - - (E)-Cinnamyl alcohol# - - - - - 0.46 - Methyl o-methoxybenzoate# - - - - 37.50 - - *Benzyl butyrateA - - - - - - - *Eugenol# - - - - - - - 3,4-Dimethoxystyrene# - - - - - - - Aromatic compounds *p-Methoxystyrene # *2-Phenylpropenal *Hydroquinone N N1 S.fabarioides night - S.fabarioides day - S.holzmannii night - L.coronaria night - L.coronaria day - S.tatarica night - S.tatarica day - 3-Phenylpropyl acetateN - - - - - - - Methyleugenol# - - - - - - - *Vanillin# - - - - - - - - - - - - 0.07 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0.17 - - - - - - - - - - - - - 1.39 - 2-MethylbutylaldoximeMS - - - - - 42.10 - 3-Methylbutylaldoxime# - - - - - 9.20 - - - - - - 23.33 - - - - - - - - *Phenylacetonitrile# - - - - - - - *NonanenitrileN - - - - - - - *2-Aminobenzaldehyde# - - - - - - - (E)+(Z)-Phenylacetaldoxime# - - - - - - - *Decanenitrile - - - - - - - Indole# - - - - - - - *1-Nitro-2-phenylethane# - - - - - - - *2-(Dimethylamino)benzaldehydeMS - - - - - - - *4-Methoxyphenethyl alcoholN Isoamyl benzoateA (E)-Cinnamyl acetate A *(Z)-Methyl isoeugenol A *3,4-Dimethoxybenzaldehyde N *(E)-Methyl isoeugenolA (Z)-3-Hexenyl benzoate N2 *3,4,5-Trimethoxybenzaldehyde N Benzyl benzoate# N-containing compounds *1-Nitropentane N3 *Methyl nicotinate N N S.fabarioides night S.fabarioides day S.holzmannii night L.coronaria night L.coronaria day S.tatarica night S.tatarica day *Prenyl acetate# - - - - - - - Camphene# - 99.27 - - - - - - - - - - - - - - - - - - - - - - - - 0.16 - (Z)-β-Ocimene# - - - - - - - (E)-β-Ocimene# - - - - - 0.51 75.51 (Z)-Arbusculone# - - - - - - - (E)-Arbusculone# - - - - - - - 97.82 - 100.00 - - 10.96 - *Allo-/neoallo-ocimene - - - - - - - (E)-Ocimene oxide# - - - - - 0.04 4.92 Lilac aldehyde A# 0.32 0.09 - - - - - 4-Oxoisophorone# - - - - - - - Lilac aldehyde B+C# 1.27 0.46 - - - - - Lilac aldehyde D# 0.59 0.18 - - - - - (Z)+(E)-Linalool oxide pyranoid# - - - - - - - Lilac alcohol A# - - - - - - - Lilac alcohol B+C# - - - - - - - Lilac alcohol D# - - - - - - - - - - - - - - - - - - - - - Lilac alcohol formate B+CMS - - - - - - - *Geranyl acetate# - - - - - - - Terpenoids Sabinene A β-Pinene# α-Phellandrene A Linalool# A *Geraniol# Lilac alcohol formate A MS β-BourboneneA S.fabarioides night - S.fabarioides day - S.holzmannii night - L.coronaria night - L.coronaria day - S.tatarica night - S.tatarica day - *Longifolene# - - - - - - - Germacrene D# - - - - - - - (E,E)-α-Farnesene# - - - - - 0.19 - *β-SelineneN4 - - - - - - - (E)-Nerolidol# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 5.88 - - - - - - - - m/z 124, 151, 81, 95, 165, 53KI1185 - - - - - - - KI1212 *Cubenol A *Farnesol/al isomer A Spiroacetal *2-Ethyl-1,6 dioxaspiro[4.4]nonaneMS Unknown compounds m/z 54, 55, 84, 39, 41, 64KI<900 m/z 81,79,43,109,53,77 KI1098 - - - - - - - m/z 93, 43, 55, 81, 111, 67 KI1244 - - - - - - - m/z 43, 71, 39, 55, 83, 107 KI1349 - - - - - - - m/z 91, 150, 39, 107, 79, 135KI1428 - - - - - - - KI1487 - - - - - - - - - - - - - - - - - - - 0.071 - <1 <1 - <1 <1 28 1 m/z 91, 43, 65, 162, 119, 145 m/z 91, 39, 161, 204, 105, 79 m/z 43, 108, 58, 93, 123, 67 Other unknowns KI1704 $ ng/g of dry flower weight * min N 1 1 1 1 2 3 3 $ *: compunds so far undescribed for Sileneae. #: authentic standards were available for identification. : unknowns < 1% in any species/time period were pooled with the upperscript digit giving the number of pooled compounds. N,A: compounds were identified based on ms data and comparison of Kovats retention index (KI) data provided by Adams (A)or NIST (N) (deviation of in the maximum ± 10). N1: the KI of present work (1266) differed by 25 from the KI provided by NIST (1241). N2: the KI of present work (1582) differed by 16 from the KI provided by Adams (1566). N3: the KI of present work (900) differed by 25 from the KI provided by NIST (925). N4: the KI of present work (1511) differed by 21 from the KI provided by Adams (1490). MS: Identification of compounds was based on ms data (see also Methods and Materials).
