Evaluation of Radio Frequency-Assisted Enzymatic Extraction of Non-Anthocyanin Polyphenols from Akebia trifoliata Flowers and Their Biological Activities Using UPLC-PDA-TOF-ESI-MS and Chemometrics
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Reagents
2.2. Extraction Procedures
2.3. Determination of Total Phenolics and Flavonoids
2.4. Identification of Non-Anthocyanin Polyphenols by UPLC-MS/MS
2.5. Structure Analysis
2.6. Biological Activities
2.6.1. Angiotensin-I Converting Enzyme (ACE) Inhibitory Activity
2.6.2. In Vitro Anti-Inflammatory Activities
2.6.3. Antibacterial Activities
2.7. Statistical Analysis
3. Results and Discussion
3.1. TPC and TFC
3.2. UPLC-MS Analysis
3.3. UV and FTIR
3.4. ACE Inhibitory Activity
3.5. In Vitro Anti-Inflammatory Activities
3.6. Antibacterial Activities
3.7. Chemometrics Analysis
3.7.1. Principal Component Analysis (PCA) and Heatmap Analysis
3.7.2. Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA)
3.8. Correlation Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | RT | Mass Error | [M-H]- | Fragment Ions | Formula | Suggested Compounds | Response | Reference/Standard | |||
---|---|---|---|---|---|---|---|---|---|---|---|
(min) | (ppm) | RF-E | EA | AE | HW | ||||||
1 | 3.79 | −0.5 | 353 | 191, 135, 131 | C16H18O9 | Chlorogenic acid | 126,206 | 128,733 | 71,463 | 83,772 | Standard |
2 | 4.16 | 0 | 353 | 201, 173, 135, 93 | C16H18O9 | Cryptochlorogenic acid | 62,857 | 61,068 | 48,717 | 56,961 | [26] |
3 | 4.24 | 0.1 | 353 | 191, 135, 131 | C16H18O9 | Neochlorogenic acid | 188,402 | 185,048 | 123,760 | 138,942 | [26] |
4 | 4.26 | 0.3 | 367 | 191, 135, 93 | C17H20O9 | Methyl 3-caffeoylquinate | 14,443 | 11,797 | 6043 | 7380 | [25] |
5 | 4.47 | −0.4 | 179 | 135 | C9H8O4 | Caffeic acid | 9373 | 8474 | 5642 | 6592 | Standard |
6 | 5.06 | 0.5 | 367 | 191, 161 | C17H20O9 | 3-feruloylquinic acid | 7987 | 6995 | 3181 | 4042 | Standard |
7 | 5.28 | −0.5 | 755 | 575, 413, 284, 161 | C33H40O20 | Quercetin 3-O-(2,6-α-L-dirhamno-pyranosyl)-β-D-galactopyranoside | 7456 | 7794 | 2041 | 2653 | [27] |
8 | 5.56 | 0.8 | 163 | 119 | C9H8O3 | p-coumaric acid | 1573 | 1220 | 878 | 899 | [28] |
9 | 5.67 | −1.3 | 609 | 429, 284, 227 | C27H30O16 | Quercetin 3-O-robinobioside, | 28,035 | 26,725 | 8604 | 6329 | [29] |
10 | 5.92 | −1.4 | 609 | 477, 301, 271, 161 | C27H30O16 | Quercetin-3-rutinoside | 39,759 | 38,015 | 13,955 | 16,940 | [27] |
11 | 6.26 | −1.7 | 463 | 301, 271 | C21H20O12 | Quercetin-3-O-glucoside | 12,350 | 12,659 | 1906 | 2903 | [25] |
12 | 6.94 | −0.9 | 515 | 375, 353, 335, 191, 179, 161 | C25H24O12 | Isochlorogenic acid | 183,785 | 176,185 | 48,219 | 55,802 | Standard |
13 | 7.02 | −1 | 609 | 301, 227, 151 | C27H30O16 | Quercetin 3-O-neohesperidoside | 80,762 | 75,630 | 15,931 | 22,194 | [29] |
14 | 7.24 | −0.8 | 447 | 285, 255, 151 | C21H20O11 | Kaempferol-3-O-galactopyranoside | 24,253 | 23,487 | 3459 | 4552 | [27] |
15 | 10.05 | −0.7 | 301 | / | C15H10O7 | Quercetin | 2629 | 4694 | 33,129 | 24,271 | Standard |
16 | 11.31 | −0.3 | 285 | 227, 211, 185 | C15H10O6 | Kaempferol | 46,545 | 58,540 | 75,225 | 53,514 | Standard |
Hydroxicinnamic acids | 594,626 | 579,520 | 307,903 | 354,390 | |||||||
Flavonols | 241,789 | 247,544 | 154,250 | 133,356 | |||||||
Total non-anthocyanin polyphenols | 836,415 | 827,064 | 462,153 | 487,746 |
Non-Anthocyanin Polyphenols ≠ | ACE Inhibitory | GM-CSF | TNF-β | DPPH | ABTS | CUPRAC | RP | α-Amylase | Tyrosinase | PTP-1B | S. aureus | E. coli |
---|---|---|---|---|---|---|---|---|---|---|---|---|
1 | ** | * | - | - | - | * | - | - | - | - | - | - |
2 | * | ** | - | - | * | - | - | - | - | - | - | - |
3 | *** | ** | * | - | - | - | - | - | - | - | - | - |
4 | ** | ** | ** | - | - | - | - | - | - | - | - | - |
5 | *** | ** | * | - | - | - | - | - | - | - | - | - |
6 | *** | ** | * | - | - | - | - | - | - | - | - | - |
7 | ** | * | - | - | * | - | - | - | - | - | - | |
8 | * | ** | *** | - | - | - | * | - | - | - | - | - |
9 | ** | - | * | * | - | - | * | - | * | * | - | - |
10 | *** | * | * | - | - | - | - | - | - | - | - | - |
11 | ** | * | - | - | * | - | - | - | - | - | - | |
12 | ** | * | * | * | - | - | - | - | - | - | - | - |
13 | ** | * | * | - | - | - | - | - | - | - | - | - |
14 | ** | * | * | * | - | - | - | - | - | - | - | - |
15 | *** | ** | - | - | - | - | - | - | - | - | - | |
16 | - | - | - | - | - | - | - | - | - | - | - | - |
Hydroxycinnamic acids | *** | * | * | - | - | - | - | - | - | - | - | - |
Flavonols | * | - | * | ** | - | - | * | * | * | * | - | * |
Total non-anthocyanin polyphenols | ** | * | * | * | - | - | - | - | - | - | - | - |
Total phenolics | - | - | - | - | - | * | - | - | - | - | - | - |
Total flavonoids | - | - | - | - | - | - | - | - | - | - | ** | - |
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Song, X.; Jiang, Y.; Zhong, Y.; Wang, D.; Deng, Y. Evaluation of Radio Frequency-Assisted Enzymatic Extraction of Non-Anthocyanin Polyphenols from Akebia trifoliata Flowers and Their Biological Activities Using UPLC-PDA-TOF-ESI-MS and Chemometrics. Foods 2022, 11, 3410. https://doi.org/10.3390/foods11213410
Song X, Jiang Y, Zhong Y, Wang D, Deng Y. Evaluation of Radio Frequency-Assisted Enzymatic Extraction of Non-Anthocyanin Polyphenols from Akebia trifoliata Flowers and Their Biological Activities Using UPLC-PDA-TOF-ESI-MS and Chemometrics. Foods. 2022; 11(21):3410. https://doi.org/10.3390/foods11213410
Chicago/Turabian StyleSong, Xiaoyong, Yongli Jiang, Yu Zhong, Danfeng Wang, and Yun Deng. 2022. "Evaluation of Radio Frequency-Assisted Enzymatic Extraction of Non-Anthocyanin Polyphenols from Akebia trifoliata Flowers and Their Biological Activities Using UPLC-PDA-TOF-ESI-MS and Chemometrics" Foods 11, no. 21: 3410. https://doi.org/10.3390/foods11213410