Phytochemical and Bioactivity Studies on Hedera helix L. (Ivy) Flower Pollen and Ivy Bee Pollen
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Samples
2.3. Preparation of Standard Solutions
2.4. Preparation of Sample Test Solutions
2.5. Isolation and Structure Elucidation of the Marker Compounds from the Bee Pollen Sample
2.6. MS/MS Analyses
2.7. HPTLC Analyses
2.8. HPLC Analyses
2.9. In Vitro Bioactivity Analyses
2.9.1. DPPH• Assay
2.9.2. FRAP Assay
2.9.3. CUPRAC Assay
2.9.4. ABTS Assay
2.9.5. Xanthine Oxidase Inhibitory Activity
2.9.6. Superoxide Radical Scavenging (SOD) Activity
2.10. HPTLC-Effect-Directed Analyses (EDA)
2.10.1. HPTLC-DPPH•
2.10.2. HPTLC-Xanthine Oxidase Inhibitory Activity
2.11. Statistical Analyses
3. Results and Discussion
3.1. Isolation and Structural Elucidation of Compounds Isolated from BP-SI
3.2. HPTLC Chemical Profiling
3.3. HPLC Analyses
3.3.1. HPLC Method Validation
Specificity
Linearity of the Calibration Curve, Limit of Detection (LOD), and Limit of Quantification (LOQ)
Precision
Accuracy
3.3.2. Quantitative Analyses
3.4. In Vitro Bioactivity Analyses
3.4.1. Antioxidant Activity Determined by DPPH, FRAP, ABTS, and CUPRAC Assays
3.4.2. Xanthine Oxidase Inhibitory Activity and Superoxide Radicals Scavenging Activity
3.5. HPTLC-Effect-Directed Analyses
3.5.1. HPTLC-DPPH Analyses of Antioxidant Activity
3.5.2. HPTLC-XO Inhibitory Activity
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compounds | MS (m/z) [Relative Intensity] | MSn (m/z) [Relative Intensity] |
---|---|---|
Quercetin-3-O-β- glucopyrnosyl-(1→2)- β-galactopyranoside | 625 [100], 626 [41], 627 [10], 723 [6], 661 [3], 1251 [3] | MS2 [625]: 300 [100], 301 [73], 445 [33], 505 [17], 271 [16], 463 [11], 355 [9], 255 [8], 343 [8], 299 [6], 325 [5], 273 [4], 409 [4], 427 [4], 367 [3] |
MS3 [625 → 300]: 271 [100], 255 [61], 272 [12], 254 [7], 243 [3] | ||
MS2 [723]: 625 [100], 399 [34], 437 [21], 687 [21], 685 [21]. 437 [21] MS3 [723 → 625]: 300 [100], 301 [76], 445 [40], 271 [17], 505 [17], 463 [13] MS2 [661]: 625 [100] MS3 [661 → 625]: 300 [100] | ||
Platanoside | 723 [100], 724 [49], 725 [13], 759 [13], 739 [9], 1447 [5] | MS2 [723]: 437 [100], 285 [36], 577 [4] MS3 [723 → 437]: 145 [100], 291 [72], 163 [71], 273 [63], 187 [23], 211 [16], 229 [14], 419 [14], 201 [10], 375 [7] MS2 [759]: 723 [100] MS3 [759 → 723]: 437 [100], 285 [31], 577 [4] MS4 [759 → 723 → 437]: 145 [100], 291 [70], 163 [68], 273 [54], 187 [21], 211 [16], 229 [15], 419 [14], 201 [8] MS2 [739]: 453 [100], 593 [24], 285 [19], 301 [14], 307 [4], 437 [3], 300 [2] MS3 [739 → 453]: 307 [100], 161 [45], 179 [34], 289 [22], 163 [13], 291 [12], 1445 [10], 217 [9], 263 [7], 135 [6], 227 [6] MS4 [739 → 453 → 307]: 161 [100], 135 [39], 179 [34] |
Afzelin | 431 [100], 432 [27], 863 [19], 467 [15], 630 [9], 285 [3] | MS2 [431]: 285 [100], 284 [44], 327 [5] MS3 [431→285]: 257 [100], 229 [46], 267 [40], 241 [30], 213 [20], 285 [18], 197 [18], 239 [15], 163 [15] MS4 [431→285 → 257]: 229 [100], 163 [67], 239 [38], 213 [22], 185 [11], 187 [9], 189 [9], 257 [7] MS2 [863]: 701 [100], 717 [97], 727 [64], 697 [32], 831 [24], 571 [17], 561 [17] 285 [6], 431 [2] MS2 [467]: 431 MS3 [467 → 431]: 285 [100], 327 [8], 255 [6] |
Standards | Linearity Range (µg/mL) | r2 | S * | Intercept | SD ** | LOD (µg/mL) | LOQ (µg/mL) |
---|---|---|---|---|---|---|---|
Chlorogenic acid | 0.5–50 | 0.9995 | 20.590 | 2.950 | 0.186 | 0.027 | 0.090 |
Quercetin-3-O-β-glucopyranosyl- (1→2)-β-galactopyranoside | 0.5–50 | 0.9998 | 7.899 | 2.244 | 0.058 | 0.022 | 0.073 |
3,5-Dicaffeoylquinic acid | 1–100 | 0.9994 | 31.248 | 9.637 | 0.790 | 0.076 | 0.253 |
Afzelin | 1–50 | 0.9974 | 23.451 | 30.016 | 0.266 | 0.041 | 0.136 |
Platanoside | 0.5–50 | 0.9998 | 38.132 | 0.982 | 0.271 | 0.021 | 0.071 |
Intraday Precision | Interday Precision | ||||
---|---|---|---|---|---|
Standards | Concentration (µg/mL) | Average Concentration (µg/mL ± SD) (n = 3) | RSD (%) (n = 3) | Average Concentration (µg/mL ± SD) (n = 3) | RSD (%) (n = 3) |
Chlorogenic acid | 5 | 5.283 ± 0.028 | 0.539 | 5.265 ± 0.014 | 0.266 |
5.272 ± 0.008 | 0.160 | 5.269 ± 0.006 | 0.106 | ||
5.259 ± 0.003 | 0.053 | 5.338 ± 0.023 | 0.430 | ||
Quercetin-3-O-β-glucopyraosyl- (1→2)-β-galactopyranoside | 5 | 5.155 ± 0.032 | 0.618 | 5.172 ± 0.013 | 0.245 |
5.142 ± 0.039 | 0.752 | 5.218 ± 0.015 | 0.280 | ||
5.146 ± 0.013 | 0.246 | 5.311 ± 0.022 | 0.413 | ||
Platanoside | 5 | 5.134 ± 0.007 | 0.135 | 5.165 ± 0.007 | 0.128 |
5.141 ± 0.004 | 0.078 | 5.201 ± 0.008 | 0.162 | ||
5.142 ± 0.007 | 0.135 | 5.263 ± 0.003 | 0.050 | ||
3,5-Dicaffeoylquinic acid | 10 | 9.936 ± 0.033 | 0.335 | 9.921 ± 0.032 | 0.318 |
9.907 ± 0.004 | 0.037 | 9.951 ± 0.020 | 0.201 | ||
9.904 ± 0.002 | 0.019 | 10.052 ± 0.043 | 0.424 | ||
Afzelin | 10 | 9.492 ± 0.020 | 0.206 | 9.526 ± 0.004 | 0.045 |
9.489 ± 0.002 | 0.026 | 9.590 ± 0.011 | 0.118 | ||
9.501 ± 0.004 | 0.045 | 9.704 ± 0.009 | 0.091 |
Added Concentration (µg/mL) | Recovery (%) (n = 3) | Added Concentration (µg/mL) | Recovery (%) (n = 3) | ||||
---|---|---|---|---|---|---|---|
Samples | Chlorogenic Acid | Quercetin-3-O-β- glucopyranosyl-(1→2)-β-galactopyranoside | Platanoside | 3,5-Dicaffeoyl- quinic Acid | Afzelin | ||
BP-TR | 12.5 | 103.9 | 102.9 | 104.9 | 25 | 108.4 | 95.8 |
6.25 | 97.3 | 104.4 | 94.6 | 12.5 | 90.9 | 82.6 | |
3.125 | 94.0 | 102.6 | 105.9 | 6.25 | 72.3 | 85.0 | |
BP-SI | 12.5 | 100.8 | 98.6 | 105.0 | 25 | 107.2 | 95.2 |
6.25 | 103.6 | 102.5 | 107.4 | 12.5 | 91.8 | 87.1 | |
3.125 | 103.8 | 106.1 | 105.9 | 6.25 | 72.2 | 92.4 | |
FP | 12.5 | 100.6 | 96.3 | 93.1 | 25 | 83.8 | 78.4 |
6.25 | 97.3 | 93.7 | 104.4 | 12.5 | 99.6 | 86.3 | |
3.125 | 90.3 | 80.0 | 96.6 | 6.25 | 76.9 | 87.7 |
Samples | Chlorogenic Acid | Quercetin-3-O-β- glucopyranosyl-(1→2)-β- galactopyranoside | Platanoside | 3,5-Dicaffeoylquinic Acid | Afzelin |
---|---|---|---|---|---|
mg/g ± SD (n = 3) | |||||
BP-TR | N.d. | 29.041 ± 0.088 a | 2.030 ± 0.009 c | N.d. | 2.052 ± 0.002 c |
BP-SI | N.d. | 24.400 ± 0.211 b | 7.283 ± 0.107 a | N.d. | 2.419 ± 0.007 b |
FP | 3.480 ± 0.010 | 3.959 ± 0.082 c | 6.242 ± 0.039 b | 22.372 ± 0.032 | 6.598 ± 0.010 a |
Compounds and Samples | DPPH | FRAP | ABTS | CUPRAC |
---|---|---|---|---|
mg TE/g (n = 3) | ||||
Quercetin-3-O-β-glucopyranosyl- (1→2)-β-galactopyranoside | 400.21 ± 11.78 c | 227.30 ± 2.65 c | 242.13 ± 5.88 c | 560.53 ± 14.74 c |
Chlorogenic acid | 812.72 ± 4.99 a | 676.51 ± 2.34 a | 803.52 ± 1.12 a | 950.43 ± 7.64 a |
Afzelin | 149.35 ± 4.28 d | 58.54 ± 2.37 d | 104.71 ± 0.25 e | 171.40 ± 8.24 e |
3,5-Dicaffeoylquinic acid | 665.53 ± 1.96 b | 542.36 ± 15.41 b | 701.64 ± 13.63 b | 760.83 ± 12.84 b |
Platanoside | 143.11 ± 1.31 d | 49.06 ± 0.91 de | 173.15 ± 0.86 d | 213.68 ± 8.41 d |
FP | 42.28 ± 0.68 e | 34.49 ± 0.05 e | 41.82 ± 2.87 f | 98.96 ± 4.22 f |
BP-TR | 11.00 ± 0.04 f | 6.99 ± 0.12 f | 6.24 ± 0.14 g | 22.20 ± 1.31 g |
BP-SI | 14.61 ± 0.75 f | 7.61 ± 0.27 f | 9.35 ± 0.15 g | 30.35 ± 1.56 g |
Compounds and DSTSs | XO Inhibitory Activity | SOD Activity |
---|---|---|
IC50 (µg/mL ± SD) (n = 3) | ||
Quercetin-3-O-β-glucopyranosyl-(1→2)-β-galactopyranoside | 73.01 ± 3.42 d | 5.09 ± 0.36 a |
Chlorogenic acid | 12.68 ± 1.12 b | 1.58 ± 0.09 a |
Afzelin | 14.46 ± 1.47 bc | 20.61 ± 1.30 b |
3,5-Dicaffeoylquinic acid | 17.47 ± 2.23 c | 5.87 ± 0.32 a |
Platanoside | N.d. | N.d. |
FP | N.d. | 36.92 ± 3.49 c |
BP-TR | N.d. | 63.08 ± 4.00 e |
BP-SI | N.d. | 48.14 ± 2.42 d |
Allopurinol | 2.25 ± 0.04 a | 3.03 ± 0.10 a |
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Sen, N.B.; Guzelmeric, E.; Vovk, I.; Glavnik, V.; Kırmızıbekmez, H.; Yesilada, E. Phytochemical and Bioactivity Studies on Hedera helix L. (Ivy) Flower Pollen and Ivy Bee Pollen. Antioxidants 2023, 12, 1394. https://doi.org/10.3390/antiox12071394
Sen NB, Guzelmeric E, Vovk I, Glavnik V, Kırmızıbekmez H, Yesilada E. Phytochemical and Bioactivity Studies on Hedera helix L. (Ivy) Flower Pollen and Ivy Bee Pollen. Antioxidants. 2023; 12(7):1394. https://doi.org/10.3390/antiox12071394
Chicago/Turabian StyleSen, Nisa Beril, Etil Guzelmeric, Irena Vovk, Vesna Glavnik, Hasan Kırmızıbekmez, and Erdem Yesilada. 2023. "Phytochemical and Bioactivity Studies on Hedera helix L. (Ivy) Flower Pollen and Ivy Bee Pollen" Antioxidants 12, no. 7: 1394. https://doi.org/10.3390/antiox12071394