Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia
Abstract
:1. Introduction
2. Results and Discussion
2.1. Metabolite Profiling Determined via LC-MS/MS
2.2. Molecular Network
2.2.1. Metabolite Profiling of the Rhizome Extract Based on LC-MS/MS and MN
Peak Number | Retention Time (RT) | [M − H]− (m/z) | MS/MS (m/z) | Proposed Compound | Reference |
---|---|---|---|---|---|
1 | 5.39 | 353 | 353, 191 | 4-[[3-(3,4- Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid. | [27] |
2 | 5.46 | 495 | 495, 315, 161 | Curculigine | [36] |
3 | 5.61 | 991 | 991, 495 | Unknown | - |
4 | 5.74 | 353 | 353, 155, 135 | Curculigine M | [34] |
5 | 5.85 | 333 | 333, 315, 109 | Curculigine G | [18] |
6 | 6.20 | 477 | 477, 109 | Curcapicycloside | [25,37] |
7 | 6.46 | 407 | 407, 379, 226 | 1-(2,3-Dihydroxyphenyl)-2-phenyl-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethanone | [35] |
8 | 6.63 | 315 | 315, 297, 150 | Sinensigenin A | [30] |
9 | 6.84 | 509 | 509, 311,174 | 1-O-methylisocurculigine | [28,32] |
10 | 6.97 | 509 | 509, 371 | Breviscaside B | [31] |
11 | 7.04 | 477 | 477, 315, 297, 161 | Crassifoside D | [29,38] |
12 | 7.50 | 347 | 347, 315, 109 | Curculigenin | [28] |
13 | 7.65 | 377 | 377, 347,174 | Unknown | - |
14 | 7.93 | 347 | 347, 315 | Unknown | - |
15 | 8.11 | 511 | 511, 181 | Sinenside B | [32] |
16 | 10.58 | 395 | 395, 138, 79 | Orcinoside J | [26] |
17 | 11.06 | 493 | 493, 447, 315, 161 | Crassifoside C | [29] |
2.2.2. Metabolite Profiling of the Leaf Extract Based on LC-MS/MS and MN
Peak Number | Retention Time (RT) | [M − H]− (m/z) | MS/MS (m/z) | Proposed Compound | Reference |
---|---|---|---|---|---|
1 | 4.35 | 431 | 431, 385, 289, 179 | Tetrahydromethylmononyasine A | [39] |
2 | 5.38 | 403 | 403, 223 401, 241, 223 | 2-(4-Ethylbenzyl)-5-hydroxymethylphenyl 4-deoxy-4-C-methyl-beta-D-glucopyranoside | [44] |
3 | 6.15 | 415 | 415, 248, 226, 174 | Orcinosides E | [41] |
4 | 7.86 | 445 | 445, 384, 174 | Orcinol gentiobioside | [27] |
5 | 8.51 | 327 | 327, 248, 225, 174 | Unknown | - |
6 | 9.07 | 329 | 329, 248, 226, 191, 174 | (1R, 2R)-crassifogenin D or (1S, 2R)-crassifogenin D | [33] |
7 | 12.20 | 267 | 267, 248, 194, | (2R,4S,5S,6R)-2-Ethyl-6-(4-methylphenoxy)oxane-3,4,5-triol | [43] |
8 | 12.90 13.84 | 723 721 | 721, 514, 248 | Unknown | - |
9 | 13.34 14.99 | 293 | 293, 248, 236, 174 | 3, 4, 5-Triacetoxybenzoic acid | [42] |
10 | 14.11 | 559 | 559, 514, 384, 248, 174 | Unknown | - |
11 | 14.30 14.87 | 295 297 | 295, 190 | Sinensigenin B | [32] |
12 | 15.79 | 555 | 555, 391, 226 | (Z)-Resveratrol 3,4′-diglucoside | [40,45] |
13 | 16.99 | 271 | 271, 248, 212, 197 | Unknown | - |
14 | 17.47, 18.61 | 377 379 | 377, 277, 248, 212 | Unknown | - |
15 | 19.70 | 355 | 355, 299, 226, 194 | Curculigine M | [34] |
16 | 19.87 | 381 | 381, 349, 281, 226 | Unknown | - |
2.3. The Total Phenolic Content of Methanol Extracts
2.4. Antioxidant Capacity of Curculigo Latifolia Extract (Fruit, Leaves, and Rhizome)
2.4.1. DPPH• Radical Scavenging Activity Assay
2.4.2. Determination of Antioxidant Activity via the β-Carotene Bleaching Method
2.5. Antimicrobial Assay
3. Materials and Methods
3.1. Sample Collection
3.2. Extraction
3.2.1. Fruits
3.2.2. Leaf and Rhizomes
3.3. Ultra-High Performance Liquid Chromatography–MS/MS (UHPLC-MS/MS) Analysis
3.4. Molecular Networking (MN)
3.5. Antioxidant Assay
3.5.1. 2,2-Diphenyl-1-picryl-hydrazyl-hydrate (DPPH•) Assay
3.5.2. Total Phenolic Content (TPC)
3.5.3. β-Carotene Bleaching Assays
3.6. Antimicrobial Screening of Extracts
3.6.1. Microorganisms
3.6.2. Antibacterial Assay Methodology (Disk Diffusion Assay)
3.6.3. Determination of Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) Values
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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DPPH• IC50 (µg/mL) | TPC GAE (µg/g) | β-Carotene (%) | |
---|---|---|---|
Fruit | 26.99 ± 1.58 | 153.34 ± 0.32 | 28.55 ± 4.17 |
Rhizome | 18.10 ± 0.91 | 175.75 ± 0.43 | 35.20 ± 4.74 |
Leaf | 547.29 ± 5.09 | 130.69 ± 0.48 | 31.38 ± 0.60 |
Vitamin C | 11.49 ± 0.071 | - | 52.71 ± 5.25 |
Vitamin E | - | 93.35 ± 0.30 | |
BHA | - | 80.56 ± 2.78 | |
BHT | - | 77.76 ± 0.80 |
Sample | Target Microbe | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
Bacillus subtilis B29 | Staphylococcus aureus ATCC 43300 | Escherichia coli UPMC 25922 | Salmonella choleraesuis ATCC 10708 | |||||||||
Inhibition Zone (mm) | Inhibition Zone (mm) | Inhibition Zone (mm) | Inhibition Zone (mm) | |||||||||
i | ii | iii | i | ii | iii | i | ii | iii | i | ii | iii | |
Fruit | - | - | - | 7 | 8 | 7 | - | - | - | - | - | - |
Leaf | - | - | - | 15 | 16 | 15 | - | - | - | 8 | 8 | 8 |
Rhizome | - | - | - | - | - | - | - | - | - | - | - | - |
Streptomycin (+ve) | 29 | 30 | 25 | 32 |
Experimental Strain | Leaf (1.0 mg/mL) | |
---|---|---|
Minimum Inhibitory Concentration, MIC (mg/mL) | Minimum Bactericidal Concentration, MBC (mg/mL) | |
Staphylococcus aureus | ±0.25 | ±0.25 |
Salmonella choleraesuis | ±0.25 | ±0.25 |
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Mad Nasir, N.; Ezam Shah, N.S.; Zainal, N.Z.; Kassim, N.K.; Faudzi, S.M.M.; Hasan, H. Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia. Plants 2021, 10, 1488. https://doi.org/10.3390/plants10081488
Mad Nasir N, Ezam Shah NS, Zainal NZ, Kassim NK, Faudzi SMM, Hasan H. Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia. Plants. 2021; 10(8):1488. https://doi.org/10.3390/plants10081488
Chicago/Turabian StyleMad Nasir, Nadiah, Nur Syafiqah Ezam Shah, Nurul Zulaikha Zainal, Nur Kartinee Kassim, Siti Munirah Mohd Faudzi, and Hanan Hasan. 2021. "Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia" Plants 10, no. 8: 1488. https://doi.org/10.3390/plants10081488