NMR Metabolomics of Arctium lappa L., Taraxacum officinale and Melissa officinalis: A Comparison of Spontaneous and Organic Ecotypes
Abstract
:1. Introduction
2. Materials and Methods
2.1. Sampling
2.2. Chemicals
2.3. Extraction Procedure for NMR Analysis
2.4. NMR Analysis
2.5. Statistical Analysis
3. Results and Discussions
3.1. NMR Assignment of Hydroalcoholic and Organic Fractions
NMR Identification of Polyphenols
3.2. Characterisation and Comparison among the Three Ecotypes of the Same Species
3.2.1. Burdock—Arctium lappa L.
3.2.2. Dandelion—Taraxacum officinale
3.2.3. Lemon Balm—Melissa officinalis
3.3. Comparison of Burdock, Dandelion and Lemon Balm
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviation
DGG | Digalactosyldiacylglycerol |
DUFA | Di-unsaturated fatty acids |
GABA | γ-amino-butyric acid |
GC-MS | Gas Chromatography–Mass Spectroscopy |
1H-13C | HSQC Heteronuclear single quantum coherence Spectroscopy |
1H-13C | HMBC Heteronuclear Multiple Bond Correlation Spectroscopy |
1H-1H | TOCSY Total Correlation Spectroscopy |
HPLC-DAD | High-Performance Liquid Chromatography–Diode Array Detector |
HPLC-MS | High-Performance Liquid Chromatography–Mass Spectroscopy |
LSE | Land Spontaneous Ecotype |
MUFA | Mono-unsaturated fatty acids |
MSE | Mountain Spontaneous Ecotype |
NMR | Nuclear Magnetic Resonance |
OE | Organic Ecotype |
PCA | Principal Component Analysis |
QTRAP-MS | Mass Spectroscopy |
UFA | Unsaturated Fatty Acids |
UHPLC-MS | Ultra-High-Performance Liquid Chromatography-Mass Spectroscopy |
UPLC | Ultra-Pressure Liquid Chromatography |
TBZ | 3,4,5-Trimethoxybenzaldehyde |
TSP | 3-(trimethylsilyl)-propionic-2,2,3,3-d4 acid sodium salt |
TUFA | Tri-unsaturated fatty acids |
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Plant | Harvesting Time | Ecotype | Altitude | Treatment |
---|---|---|---|---|
Burdock (root) | October | Land Spontaneous (LSE) | 150 m | No treat, wild grown |
Mountain Spontaneous (MSE) | 800 m | No treat, wild grown | ||
Organic (OE) | 150 m | Remotion of other vegetable species from the soil | ||
Dandelion (aerial part and root) | October | Land Spontaneous (LSE) | 150 m | No treat, wild grown |
Mountain Spontaneous (MSE) | 800 m | No treat, wild grown | ||
Organic (OE) | 150 m | Remotion of other vegetable species from the soil | ||
Lemon Balm (aerial part) | May | Land Spontaneous (LSE) | 150 m | No treat, wild grown |
Mountain Spontaneous (MSE) | 800 m | No treat, wild grown | ||
Organic (OE) | 150 m | Remotion of other vegetable species from the soil |
Compound | Assignment | 1H (ppm) | Multiplicity [J(Hz)] | 13C (ppm) | Burdock | Dandelion | Lemon Balm |
---|---|---|---|---|---|---|---|
Sugars | |||||||
α-D-Fructofuranose | C-2 | 105.9 | ● | ● | ● | ||
CH-3 | 4.11 | 82.3 | |||||
β-D-Fructofuranose | C-2 | 102.6 | ● | ● | ● | ||
CH-4 | 4.12 | 75.6 | |||||
β-D-Fructopyranose | C-2 | 99.3 | ● | ● | ● | ||
CH-3 | 3.80 | 68.6 | |||||
β-Galactose | CH-1 | 4.60 D,L | d [7.9] | 97.3 | ● | ● | |
CH-2 | 3.51 | ||||||
CH-3 | 3.67 | ||||||
CH-4 | 3.95 | ||||||
CH-5 | 4.05 | ||||||
CH-6 | 3.78 | ||||||
α-Glucose | CH-1 | 5.23 B,D,L | d [3.8] | 93.3 | ● | ● | ● |
CH-2 | 3.54 | 72.6 | |||||
CH-3 | 3.72 | 73.3 | |||||
CH-4 | 3.41 | 70.8 | |||||
CH-5 | 3.84 | 72.5 | |||||
β-Glucose | CH-1 | 4.66 B,D,L | d [7.9] | 97.0 | ● | ● | ● |
CH-2 | 3.25 | 75.3 | |||||
Inulin | CH-1 (Glc) | 5.44 | 93.9 | ● | ● | ||
CH-2 | 3.57 | 72.1 | |||||
CH-3 | 3.78 | 73.6 | |||||
CH-4 | 3.48 | 70.2 | |||||
CH-5 | 3.85 | 73.4 | |||||
CH2-6 | 3.83 | 61.1 | |||||
CH2-1′ (Fru) | 3.75; 3.89 | ||||||
CH-3′a | 4.21 | 77.5 | |||||
CH-3′b | 4.26 | ||||||
CH-4′a | 4.05 | 74.9 | |||||
CH-5′ | 3.89 | 82.2 | |||||
Myo-inositol | CH-2,5 | 3.56 | ● | ● | |||
CH-3,6 | 3.65 | ||||||
CH-4 | 3.28 D,L | 75.0 | |||||
Sucrose | CH-1 (Glc) | 5.42 B,D,L | d [3.9] | 93.1 | ● | ● | ● |
CH-2 | 3.53 | 71.8 | |||||
CH–3 | 3.72 | 73.6 | |||||
CH–4 | 3.42 | 70.2 | |||||
CH–5 | 3.84 | 73.5 | |||||
C2′ (Fru) | 104.8 | ||||||
CH–3′ | 4.23 | 77.4 | |||||
CH–5′ | 3.92 | 82.4 | |||||
CH–4′ | 3.83 | 61.2 | |||||
Organic acids | |||||||
Acetate | CH3 | 1.92 B,D | s | 24.4 | ● | ● | ● |
COO- | 184.4 | ||||||
Citrate | α, γ-CH | 2.56 B,D,L | d [16.0] | 46.0 | ● | ● | ● |
α′, γ′-CH | 2.68 | 46.0 | |||||
β-C | 73.2 | ||||||
1,5-COO- | 180.2 | ||||||
6-COO- | 183.0 | ||||||
Formate | HCOO- | 8.46 B,D,L | s | ● | ● | ● | |
Fumarate | α, β-CH=CH | 6.53 B,D | s | 136.7 | ● | ● | |
Lactate | β -CH3 | 1.34 B | d [7.1] | 21.4 | ● | ||
Malate | α-CH | 4.31 B,D,L | dd [9.9; 3.1] | 71.0 | ● | ● | ● |
β-CH | 2.68 | dd [15.5; 3.1] | 43.5 | ||||
β′-CH | 2.41 | dd [15.5; 9.9] | 43.5 | ||||
Succinate | α, β-CH2 | 2.42 B,D,L | s | 35.2 | ● | ● | ● |
Tartrate | CH(OH)COO- | 4.34 D,L | s | 75.3 | ● | ● | |
Amino acids | |||||||
Alanine | α-CH | 3.80 | 51.0 | ● | ● | ● | |
β-CH3 | 1.49 B,D,L | d [7.2] | 17.3 | ||||
COO- | 178.6 | ||||||
Arginine | α-CH | 3.77 | 55.4 | ● | ● * | ||
β-CH2 | 1.91 | m | 28.0 | ||||
γ-CH | 1.67 B,D | m | 25.3 | ||||
γ′-CH | 1.74 | m | 25.3 | ||||
δ-CH3 | 3.24 | 41.5 | |||||
Asparagine | α-CH | 4.00 | 52.8 | ● | ● | ||
β, β′-CH2 | 2.88 B; 2.96 D | dd [7.7; 16.8] dd [4.3; 16.8] | 35.6 | ||||
COO- | 176.5 | ||||||
Aspartate | β, β′-CH2 | 2.70 L; 2.81 D | dd [3.7; 17.5] | 37.0 | ● | ● | |
α-CH | 3.92 | 54.0 | |||||
γ-COO- | 177.3 | ||||||
GABA | α-CH2 | 2.30 D,L | t [7.4] | 35.4 | ● | ● | |
β-CH2 | 1.90 | 24.9 | |||||
γ-CH2 | 3.01 | t [7.5] | 40.4 | ||||
Glutamine | α-CH | 3.76 | 55.3 | ● | ● | ● | |
β, β′-CH2 | 2.14 | m | 27.5 | ||||
γ-CH | 2.45 B,D,L | m | 31.9 | ||||
Glycine | α-CH2 | 3.58 | s | 42.5 | ● | ||
Isoleucine | α-CH | 1.97 | 38.0 | ● | ● | ● | |
β-CH | 1.27 | 29.4 | |||||
γ-CH3 | 1.01 B,D,L | d [7.1] | 15.7 | ||||
δ-CH3 | 0.89 | d [7.4] | |||||
Leucine | β-CH2 | 1.74 | 41.0 | ● | ● | ● | |
γ-CH | 1.71 | ||||||
δ-CH3 | 0.97 B,D,L | d [6.2] | 23.1 | ||||
δ′-CH3 | 0.96 | 22.1 | |||||
Phenylalanine | CH-2,6 | 7.33 | m | 130.7 | ● | ||
CH-4 | 7.38 | ||||||
CH-3,5 | 7.43 D | m | 130.6 | ||||
Proline | α-CH | 4.13 L | 62.5 | ● | ● | ● | |
β, β′-CH2 | 2.07, 2.33 | 30.0 | |||||
γ-CH3 | 2.01 B,D | m | 25.0 | ||||
δ, δ′-CH3 | 3.33, 3.41 | 47.4 | |||||
Threonine | α-CH | 3.59 | 62.3 | ● | ● | ● | |
γ-CH3 | 1.33 B,D,L | d [6.7] | 20.7 | ||||
Tyrosine | CH-2, 6 ring | 7.22 | d [8.2] | 132.0 | ● | ● | |
CH-3, 5 ring | 6.96 B,D | d [8.5] | 117.0 | ||||
Tryptophan | CH-4 ring | 7.74 | ● | ● | |||
CH-5 ring | 7.20 | ||||||
CH-6 ring | 7.29 | ||||||
CH-7 ring | 7.53 B,D | d [8.1] | |||||
Valine | α-CH | 3.60 | ● | ● | ● | ||
β-CH | 2.27 | ||||||
γ-CH3 | 1.10 | d [7.1] | 17.7 | ||||
γ′-CH3 | 1.04 B,D,L | d [7.1] | 19.0 | ||||
Other compounds | |||||||
Choline | +N(CH3)3 | 3.20 B,D,L | s | 55.1 | ● | ● | ● |
Ethanolamine | α, β-CH2 | 3.14 B,D | t [5.2] | 42.1 | ● | ● | |
Trigonelline | CH-1 | 9.13 B,D | s | ● | ● | ||
CH-3 | 4.42 | s | |||||
CH-4 | 8.09 | ||||||
Caftaric acid | CH-10 | 5.31 D | d [2.2] | ● | |||
CH-11 | 4.57 | d [2.2] | |||||
CH-2 | 6.49 | d [16.0] | 115.4 | ||||
CH-3 | 7.72 | d [16.0] | 148.0 | ||||
CH-8 ring | 6.96 | d [8.2] | 117.6 | ||||
CH-9 ring | 7.17 | dd [2.0; 8.2] | 124.2 | ||||
CH-5 ring | 7.25 | d [2.0] | 117.5 | ||||
COO− | 171.4 | ||||||
Chicoric acid | CH-10,10a | 5.54 D | s | 75.9 | ● | ||
CH-2, 2a | 6.49 | d [16.0] | 115.4 | ||||
CH-3, 3a | 7.72 | d [16.0] | 148.0 | ||||
CH-8, 8a ring | 6.96 | d [8.2] | 117.6 | ||||
CH-9, 9a ring | 7.17 | dd [2.0; 8.2] | 124.2 | ||||
CH-5, 5a ring | 7.25 | d [2.0] | 117.5 | ||||
COO− | 171.4 | ||||||
Chlorogenic acid | CH-2 | 6.22 | d [16.0] | 115.8 | ● | ||
CH-3 | 7.37 | d [16.0] | 146.8 | ||||
CH2-2′ | 1.89; 2.10 | m | 41.7 | ||||
CH-4′ | 3.90 | m | 70.8 | ||||
CH2-6′ | 1.99; 2.06 | m | 38.6 | ||||
3,5-Di-caffeoylquinic acid | CH-2, 2a | 6.13, 6.25 B | d [16.0] | 115.7, 116.5 | ● | ||
CH-3, 3a | 7.40, 7.32 | d [16.0] | 148.0, 147.8 | ||||
CH-3′, 5′ | 5.335.37 | m m | 72.3 72.9 | ||||
CH2-2′, 6′ | 1.99, 2.02 | m | 40.0 | ||||
CH-8, 8a ring | 6.58, 6.66 | d [8.3] | 116,9, 117.0 | ||||
CH-9, 9a ring | 6.70, 6.74 | dd [1.7; 8.3] | 123.9, 124.0 | ||||
CH-5, 5a ring | 7.21, 7.24 | d [1.7] | 116.2, 117.0 | ||||
Rosmarinic acid | CH-2 | 6.22 | d [16.0] | 115.8 | ● | ||
CH-3 | 7.37 | d [16.0] | 146.8 | ||||
CH-1a | 5.01 | m | 77.5 | ||||
CH2-2a | 2.85; 2.93 | m | 37.9 | ||||
Uracil | CH | 7.84 L | d | ● | |||
CH | 5.80 | d | |||||
Uridine | CH-6 | 5.90 B | d [8.1] | ● | ● | ||
CH-5 | 7.87 D | d [8.1] | |||||
CH-1′ | 5.89 | d [4.8] |
ppm | Group | Compounds | Burdock | Dandelion | Lemon Balm | ||
---|---|---|---|---|---|---|---|
Root | Leaves | ||||||
Iβ-Sit | 0.65 | CH3-18 | β-Sitosterol | ● | ● | ● | ● |
IStig | 0.67 | CH3-18 | Stigmasterol | ● | ● | ● | ● |
IFA | 2.30 | CH2-11 | Totally fatty acids | ● | ● | ● | ● |
IDUFA | 2.73 | CH2-11 | Linoleic acid | ● | ● | ● | ● |
ITUFA | 2.77 | CH2-11,14 | Linolenic acid | ● | ● | ● | ● |
IPCG | 3.23 | N(CH3)3 | Glyceroylphosphatidylcholine | ● | ● | ● | ● |
IDGG | 4.87 | CH-1 | Glyceroyldigalactose | ● | ● | ||
IPHEO | 11.15 | CH-5 | Pheophytin | ● | ● | ||
ICHL | 11.13 | CH-5 | Chlorophyll | ● | ● |
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© 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
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Ambroselli, D.; Masciulli, F.; Romano, E.; Guerrini, R.; Ingallina, C.; Spano, M.; Mannina, L. NMR Metabolomics of Arctium lappa L., Taraxacum officinale and Melissa officinalis: A Comparison of Spontaneous and Organic Ecotypes. Foods 2024, 13, 1642. https://doi.org/10.3390/foods13111642
Ambroselli D, Masciulli F, Romano E, Guerrini R, Ingallina C, Spano M, Mannina L. NMR Metabolomics of Arctium lappa L., Taraxacum officinale and Melissa officinalis: A Comparison of Spontaneous and Organic Ecotypes. Foods. 2024; 13(11):1642. https://doi.org/10.3390/foods13111642
Chicago/Turabian StyleAmbroselli, Donatella, Fabrizio Masciulli, Enrico Romano, Ruggero Guerrini, Cinzia Ingallina, Mattia Spano, and Luisa Mannina. 2024. "NMR Metabolomics of Arctium lappa L., Taraxacum officinale and Melissa officinalis: A Comparison of Spontaneous and Organic Ecotypes" Foods 13, no. 11: 1642. https://doi.org/10.3390/foods13111642