Whitening Agents from Reseda luteola L. and Their Chemical Characterization Using Combination of CPC, UPLC-HRMS and NMR
Abstract
:1. Introduction
2. Material and Methods
2.1. Plant Material
2.2. Materials
2.3. Plant Extraction
2.3.1. Soxhlet Extraction
2.3.2. Liquid-Liquid Extraction (LLE)
2.4. Biological Activity Assays
2.4.1. Instrumentation
2.4.2. DPPH Radical Scavenging Assay
2.4.3. Tyrosinase Assay
2.4.4. Lipoxygenase Assay
2.5. High-Performance-Liquid-Chromatography
2.6. Centrifugal Partition Chromatography Purification
2.7. UPLC-ESI-HRMS Analyses of Fractions
2.8. 1H NMR Analysis of Isolated Compounds
3. Results and Discussion
3.1. Fractionation Strategy
3.2. Putative Identification of Compounds
3.3. Final Purification and Identification of Active Compounds
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Extract | Inhibition (%) | ||
---|---|---|---|
DPPH | Tyrosinase | Lipoxygenase | |
RL1 | 7.00 ± 0.05 | 12.00 ± 0.03 | / |
RL2 | 7.00 ± 0.05 | 38.00 ± 0.03 | / |
RL3 | 25.00 ± 0.05 | 45.00 ± 0.01 | 52.00 ± 0.05 |
RL4 | 53.00 ± 0.05 | 18.00 ± 0.01 | 63.00 ± 0.05 |
RL5 | 16.00 ± 0.05 | / | / |
Vitamin C | 99.00 ± 0.05 | - | - |
Kojic acid | - | 96.00 ± 0.00 | - |
Quercetin hydrate | - | - | 92.00 ± 0.05 |
Compound | rt (min) | Positive Mode | Negative Mode | RDBeq | Putative Identification | ||||
---|---|---|---|---|---|---|---|---|---|
[M + H]+ m/z | EC | Fragment ions (m/z) | [M − H]− m/z | EC | Fragment Ions (m/z) | ||||
1 | 6.53 | 527.0884 | C18H23O18 | 365.0335 | 525.0695 | C18H21O18 | 363.0218 | 8 | Unknown |
153.0188 | 299.0564 | ||||||||
150.9901 | |||||||||
91.0100 | |||||||||
2 | 6.62 | 611.1619 | C27H31O16 | 449.1084 | 609.1461 | C27H29O16 | 447.0848 | 14 | Luteolin-3',7-diglucoside |
287.0568 | 285.0420 | ||||||||
365.0343 | |||||||||
3 | 7.67 | 449.1079 | C21H21O11 | 287.0555 | 447.0927 | C21H19O11 | 285.0382 | 12 | Luteolin glycoside |
4 | 8.67 | 433.1132 | C21H21O10 | 301.0723 | 431.0975 | C21H19O10 | 268.0375 | 12 | Apigenin-7-O-glucoside |
271.0615 | |||||||||
153.0190 | |||||||||
119.0504 | |||||||||
5 | 9.12 | 491.119 | C23H23O12 | 287.0566 | 489.1016 | C23H21O12 | 285.0397 | 13 | Acetylated luteolin-O-glycoside |
153.0566 | 429.0814 | ||||||||
6 | 9.30 | 449.1084 | C21H21O11 | 287.0558 | 447.0927 | C21H19O11 | 285.0390 | 12 | Luteolin glycoside |
153.0184 | |||||||||
7 | 9.57 | 365.0328 | C12H13O13 | 286.0471 | 363.0173 | C12H11O13 | 299.0561 | 7 | Unknown |
258.0539 | 211.005 | ||||||||
153.0193 | 173.0255 | ||||||||
151.0023 | |||||||||
125.0230 | |||||||||
109.0312 | |||||||||
8 | 9.91 | 491.119 | C23H23O12 | 287.0558 | 489.1033 | C23H21O12 | 285.0413 | 13 | Acetylated luteolin-O-glycoside |
153.0184 | |||||||||
9 | 10.04 | 491.119 | C23H23O12 | 287.0558 | 489.1033 | C23H21O12 | 285.0468 | 13 | Acetylated luteolin-O-glycoside |
153.0184 | |||||||||
10 | 10.21 | 475.124 | C23H23O11 | 271.0617 | 473.1084 | C23H21O11 | 268.0369 | 13 | Acetylated apigenin-O-glycoside |
153.0184 | 269.0456 | ||||||||
199.1416 | |||||||||
11 | 11.00 | 475.1247 | C23H23O11 | 271.0605 | 473.107 | C23H21O11 | 285.0338 | 13 | Acetylated apigenin-O-glycoside |
153.0184 | 268.0369 | ||||||||
269.0456 | |||||||||
12 | 11.40 | 533.1298 | C25H25O13 | 287.0558 | 531.1096 | C25H23O13 | 327.2147 | 14 | Unknown |
153.0184 | 285.0399 | ||||||||
13 | 11.60 | 287.0561 | C15H11O6 | 269.0455 | 285.0401 | C15H9O6 | 241.0473 | 11 | Luteolin |
241.0492 | 217.0513 | ||||||||
213.0549 | 199.0341 | ||||||||
179.0345 | 175.0378 | ||||||||
153.0190 | 151.0019 | ||||||||
135.0447 | 133.0285 | ||||||||
117.0338 | 107.0126 | ||||||||
14 | 12.17 | 555.0931 | C30H19O11 | 403.0839 | 553.0783 | C30H17O11 | 459.0345 | 22 | Unknown |
287.0559 | 433.0530 | ||||||||
153.0180 | 391.0460 | ||||||||
285.0389 | |||||||||
15 | 12.43 | 301.0718 | C16H13O6 | 286.0484 | 299.0553 | C16H11O6 | 284.0312 | 11 | O-Methylluteolin |
258.0535 | 256.0360 | ||||||||
229.0504 | 227.0360 | ||||||||
153.0199 | 199.0379 | ||||||||
105.0707 | 151.0028 | ||||||||
16 | 12.56 | 271.0609 | C15H11O5 | 229.0520 | 269.0451 | C15H9O5 | 225.0554 | 11 | Apigenin |
187.0404 | 201.0554 | ||||||||
153.0187 | 183.0455 | ||||||||
119.0499 | 151.0032 | ||||||||
149.0236 | |||||||||
117.0343 | |||||||||
107.0128 | |||||||||
83.0142 | |||||||||
17 | 13.02 | 495.1291 | C26H23O10 | 409.0918 | 493.1097 | C26H21O10 | 403.3051 | 16 | Unknown |
287.0552 | 285.0408 | ||||||||
257.0459 | |||||||||
18 | 13.18 | 465.1179 | C25H21O9 | 447.1079 | 463.102 | C25H19O9 | 283.0240 | 16 | Unknown |
287.0549 | 255.0293 | ||||||||
286.0464 | |||||||||
257.0454 |
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Burger, P.; Monchot, A.; Bagarri, O.; Chiffolleau, P.; Azoulay, S.; Fernandez, X.; Michel, T. Whitening Agents from Reseda luteola L. and Their Chemical Characterization Using Combination of CPC, UPLC-HRMS and NMR. Cosmetics 2017, 4, 51. https://doi.org/10.3390/cosmetics4040051
Burger P, Monchot A, Bagarri O, Chiffolleau P, Azoulay S, Fernandez X, Michel T. Whitening Agents from Reseda luteola L. and Their Chemical Characterization Using Combination of CPC, UPLC-HRMS and NMR. Cosmetics. 2017; 4(4):51. https://doi.org/10.3390/cosmetics4040051
Chicago/Turabian StyleBurger, Pauline, André Monchot, Olivier Bagarri, Philippe Chiffolleau, Stéphane Azoulay, Xavier Fernandez, and Thomas Michel. 2017. "Whitening Agents from Reseda luteola L. and Their Chemical Characterization Using Combination of CPC, UPLC-HRMS and NMR" Cosmetics 4, no. 4: 51. https://doi.org/10.3390/cosmetics4040051