Prediction of Flavor Potential of Ocimum basilicum L. Side-Stream Phytoconstituents, Using Liquid Chromatography–Tandem Mass Spectrometry Analysis and In Silico Techniques
Abstract
:1. Introduction
2. Materials and Methods
2.1. Plant Material
2.2. Extraction of the Phenolic Fraction of Basil Side-Streams
2.3. Liquid Chromatography–Tandem Mass Spectrometry (LC-MS/MS) Information-Dependent Acquisition (IDA) for the Screening of Phenolic Compounds
- Chromatographic System:
- Mass Spectral Analysis:
2.4. Flavor Prediction Tools
2.4.1. Organoleptic Profile Prediction
2.4.2. Molecular Docking Studies
2.4.3. Bitter Taste Prediction Tool
3. Results and Discussion
3.1. Determining the Phenolic Profile of Post-Distillation Basil Side-Streams Using Liquid Chromatography–Tandem Mass Spectrometry (LC-MS/MS) Information-Dependent Acquisition (IDA)
3.2. In Silico Tools for Ocimum basilicum Side-Stream Phytochemical Flavor Prediction
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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Compounds | Precursor Ion [M − H]− | Product Ions MS/MS | Chemical Group |
---|---|---|---|
1-octen-yl pentosyl glucoside | 421.20 | 259.22 | O-acyl carbohydrate |
3-(3,4-dihydroxyphenyl) lactic acid glucoside | 359.10 | 310.10, 219.10, 197.10, 161.10, 145.10 | Hydroxy monocarboxylic acid glucoside |
Caffeic acid | 179.04 | 135.04, 117.03, 107.05 | Phenolic acid |
Caffeoyl-dihydroxyphenyllactoyltartaric acid | 491.12 | 329.03, 293.04, 251.04 | Phenolic acid derivative |
Caffeoylferuloyltartaric acid (cichoric acid methyl ether) | 487.08 | 325.60, 310.70, 291.50 | Phenolic acid derivative |
Caftaric acid (Caffeoryl-tartaric acid) | 311.04 | 179.03, 149.01, 135.04 | Phenolic acid |
Chicoric acid | 947.10 * | 473.10, 341.10, 311.10, 293.10, 149.10 | Phenolic acid |
Chlorogenic acid | 353.09 | 191.05, 179.04, 161.02 | Phenolic acid |
Dihydroxy dimethoxyflavone | 313.07 | 298.10, 283.11 | Flavone |
Dihydroxybenzoic acid-O-pentosyl pentoside | 447.11 | 429.10, 403.10, 297.10, 153.10, 137.10 | Phenolic acid glucoside |
Dihydroxy-octadecadienoic acid | 311.22 | 275.21 | Hydroxy fatty acid |
Dihydroxy-octadecatrienoic acid | 309.21 | 273.20 | Hydroxy fatty acid |
Dihydroxy-oleanenoic acid | 471.34 | 399.30 | Hydroxy fatty acid |
Ethyl caffeate | 207.07 | 179.03, 161.02, 135.04 | Phenolic acid ester |
Ethyl protocatechuate | 181.05 | 153.02, 108.02 | Phenolic acid ester |
Fertaric acid (feruloytartaric acid) | 325.06 | 193.10, 134.04, 149.10 | Phenolic acid |
Ferulic acid | 193.05 | 178.03, 149.06, 134.04 | Phenolic acid |
Gallic acid | Phenolic acid | ||
Galloylglucose | 331.07 | 271.04, 211.02, 169.01, 151.00 | Tannin |
Hydroxy jasmonic acid-O-glucoside | 387.17 | 207.20, 163.20 | Sesquiterpene derivative |
Hydroxy-octadecatrienoic acid | 293.21 | 275.20, 211.20, 161.20 | Lineolic acid derivative |
Hydroxy-oxo-phytodienoic acid | 307.19 | 289.20, 265.20, 223.20 | Derivative of fatty acid |
Isocitric acid | Tricarboxylic acid | ||
Isoquercetin | 463.09 | 300.04, 286.90, 243.90 | Tetrahydroxyflavone |
Lithospermic acid A | 537.10 | 493.10, 358.10, 339.50, 293.50, 135.40 | Phenolic acid |
Methyl gallate | 183.03 | 168.00, 124.02 | Phenolic acid ester |
Nepetoidin glucoside | 475.12 | 323.10, 313.10, 161.10, 151.10 | Caffeic acid derivative |
O-caffeoyl rosmarinic acid (isomelitric acid A) | 537.10 | 493.10, 427.10, 377.10, 339.10, 161.10 | Catechol |
Palmitic acid | 255.23 | 182.20 | Fatty acids |
p-Coumaric acid | 163.04 | 133.03, 119.05, 121.01 | Phenolic acid |
p-Hydroxybenzoic acid | 137.02 | 108.2, 93.04, 90.90 | Phenolic acid |
Protocatechuic acid | 153.11 | 135.10, 132.91, 123.04, 109.03 | Phenolic acid |
Quercetin 3-O-glucoside | 463.10 | 301.04 | Flavonol derivative |
Quercetin-3-O-apiosyl (1–2) galactoside | 595.10 | 445.10, 300.04 | Flavonol derivative |
Quercetin-O-pentosyl-glucoside | 595.13 | 463.10, 445.10, 301.10 | Flavonol derivative |
Rosmarinic acid | 359.08 | 223.04,197.05, 179.04, 161.03, 135.03 | Phenolic acid |
Rosmarinic acid glucoside A | 521.12 | 359.10, 197.10, 179.04, 161.04, 135.06 | Phenolic acid derivative |
Rosmarinic acid glucoside B | 521.12 | 359.10, 323.10, 197.04, 179.04, 161.04, 135.06 | Phenolic acid derivative |
Rosmarinic acid-O-glucoside | 521.14 | 359.10, 341.10 | Phenolic acid derivative |
Rutin | 609.5 | 463.04, 301.10, 272.05, 256.03, 179.10, 151.10 | Flavonol derivative |
Sagerinic acid | 719.10 | 359.60, 197.70, 179.70, 161.10 | Lignan |
Salvialinic acid (danshensu) | 197.04 | 161.06 | Phenolic acid |
Salvianolic acid A | 493.10 | 359.10, 313.10, 295.10, 185.10 | Phenolic acid |
Salvianolic acid B | 717.14 | 519, 10, 339.10, 321.10, 293.10, 277.10 | Phenolic acid |
Salvianolic acid C | 491.10 | 311.90, 293.50, 179.30, 135.20 | Phenolic acid |
Salvianolic acid F | 313.07 | 269.60, 254,.50, 227.70 | Phenolic acid |
Salvianolic acid G | 717.14 | 555.10, 537.10, 519, 10, 339.10, 321.10, 295.10 | Phenolic acid |
Salvianolic acid H/I | 537.10 | 493.10, 339.04, 313.05, 295.10, 197.10, 179.10 | Phenolic acid |
Salvianolic acid K | 555.11 | 537.10, 493.10, 295.04 | Phenolic acid |
Salvigenin (5-Hydroxy-6,7,4’-trimethoxyflavone) | 327.21 | 311.12, 277.10, 215.04 | Flavone |
Trihydroxy-octadecendic acid | 329.07 | 315.10, 299.10 | Linoleic acid derivative |
Vanillic acid | 167.03 | 152.01, 125.87, 108.02 | Phenolic acid |
Compounds | %Bitter (Virtuous Multitaste) | TAS2R46 Probability (BitterX) |
---|---|---|
Strychnine | 75% | 74.34% |
Caffeoylferuloyltartaric acid | 55% | 58.26% |
Isoquercetin | 86% | 60.99% |
Lithospermic acid A | 53% | 70.83% |
Sagerinic acid | 52% | 51.78% |
Salvianolic acid C | 64% | 74.46% |
Salvianlolic acid F | 78% | 65.81% |
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Kritsi, E.; Tsiaka, T.; Boroboka, A.; Koletsou, G.; Theofilatos, S.; Maggenaki, A.; Christodoulou, P.; Ladika, G.; Tsiantas, K.; Sotiroudis, G.; et al. Prediction of Flavor Potential of Ocimum basilicum L. Side-Stream Phytoconstituents, Using Liquid Chromatography–Tandem Mass Spectrometry Analysis and In Silico Techniques. Separations 2024, 11, 261. https://doi.org/10.3390/separations11090261
Kritsi E, Tsiaka T, Boroboka A, Koletsou G, Theofilatos S, Maggenaki A, Christodoulou P, Ladika G, Tsiantas K, Sotiroudis G, et al. Prediction of Flavor Potential of Ocimum basilicum L. Side-Stream Phytoconstituents, Using Liquid Chromatography–Tandem Mass Spectrometry Analysis and In Silico Techniques. Separations. 2024; 11(9):261. https://doi.org/10.3390/separations11090261
Chicago/Turabian StyleKritsi, Eftichia, Thalia Tsiaka, Anna Boroboka, Garyfallia Koletsou, Spyridon Theofilatos, Artemis Maggenaki, Paris Christodoulou, Georgia Ladika, Konstantinos Tsiantas, Georgios Sotiroudis, and et al. 2024. "Prediction of Flavor Potential of Ocimum basilicum L. Side-Stream Phytoconstituents, Using Liquid Chromatography–Tandem Mass Spectrometry Analysis and In Silico Techniques" Separations 11, no. 9: 261. https://doi.org/10.3390/separations11090261