Extraction of Proanthocyanidins from Chinese Wild Rice (Zizania latifolia) and Analyses of Structural Composition and Potential Bioactivities of Different Fractions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Extraction of WRPs
2.1.1. Single Factor Experimental Analysis
2.1.2. Fitting the Model
2.1.3. Optimization of Extraction Conditions
2.2. Proanthocyanidin Content and In Vitro Bioactivities of the Isolated Fractions
2.3. Structural Composition of Fractions WRPs-1–WRPs-6
3. Materials and Methods
3.1. Plant Materials and Chemicals
3.2. Experimental Design to Set Up the Proanthocyanidins Extraction
3.2.1. Ultrasound-Assisted Extraction Procedure
3.2.2. Experimental Design
3.3. Partition and Purification of Crude WRPs
3.4. Fractionation of WRPs
3.5. Acid-Catalysis in the Presence of Phloroglucinol (Phloroglucinolysis)
3.6. UPLC-LTQ-Orbitrap-MS Analysis
3.7. Determination of Proanthocyanidin Content
3.8. DPPH Radical Scavenging Assay
3.9. α-Glucosidase Inhibition Assay
3.10. Pancreatic Lipase Inhibition Assay
3.11. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Not available. |
Source | Sum of Squares | Degree of Freedom | Mean Square | F-Value | p-Value |
---|---|---|---|---|---|
Model | 27.15 | 14 | 1.94 | 168.10 | <0.0001 * |
X1 | 7.74 | 1 | 7.74 | 670.94 | <0.0001 * |
X2 | 0.13 | 1 | 0.13 | 11.00 | 0.0051 * |
X3 | 0.12 | 1 | 0.12 | 10.00 | 0.0069 * |
X4 | 0.07 | 1 | 0.07 | 5.83 | 0.0300 * |
X1X2 | 7.78 × 10−4 | 1 | 7.78 × 10−4 | 0.067 | 0.7989 |
X1X3 | 0.35 | 1 | 0.35 | 30.53 | <0.0001 * |
X1X4 | 0.08 | 1 | 0.08 | 6.80 | 0.0206 * |
X2X3 | 7.30 × 10−3 | 1 | 7.30 × 10−3 | 0.63 | 0.4396 |
X2X4 | 0.27 | 1 | 0.27 | 23.00 | 0.0003 * |
X3X4 | 0.14 | 1 | 0.14 | 11.94 | 0.0039 * |
X12 | 12.23 | 1 | 12.23 | 105.89 | <0.0001 * |
X22 | 9.17 | 1 | 9.17 | 79.41 | <0.0001 * |
X32 | 0.41 | 1 | 0.41 | 35.66 | <0.0001 * |
X42 | 0.57 | 1 | 0.57 | 48.97 | <0.0001 * |
Residual | 0.16 | 14 | 0.012 | - | - |
Lack of fit | 0.14 | 10 | 0.014 | 2.88 | 0.1596 |
Pure error | 0.02 | 4 | 4.92 × 10−3 | - | - |
Cor total | 27.31 | 28 | - | - | - |
Fraction | Proanthocyanidin Content (mg/g Extract) | IC50/DPPH (μg/mL) | IC50/α-glucosidase (μg/mL) | IC50/pancreatic lipase (μg/mL) |
---|---|---|---|---|
WRPs-1 | 524.19 ± 3.56 e | 74.91 ± 0.83 c | 316.07 ± 1.08 a | >2000 |
WRPs-2 | 639.92 ± 5.77 c | 59.57 ± 1.52 d | 304.17 ± 2.46 b | >2000 |
WRPs-3 | 863.81 ± 8.02 a | 34.29 ± 0.78 e | 289.04 ± 3.11 c | >2000 |
WRPs-4 | 679.34 ± 4.55 b | 36.73 ± 0.96 e | 257.20 ± 3.85 d | >2000 |
WRPs-5 | 629.16 ± 6.82 c | 35.44 ± 1.02 e | 117.72 ± 1.45 f | >2000 |
WRPs-6 | 567.20 ± 5.76 d | 451.85 ± 2.47 a | 84.01 ± 0.74 g | 1054.01 ± 6.67 a |
ascorbic acid | - | 100.05 ± 0.94 b | - | - |
acarbose | - | - | 186.31 ± 1.04 e | - |
orlistat | - | - | - | 15.45 ± 0.14 b |
Retention Time (min) | [M + H]+ (m/z) | Fragment Ion (m/z) | Compound | ||
---|---|---|---|---|---|
Measured | Calculated | Error (ppm) | |||
2.71 | 431.0970 | 431.0973 | −0.67 | 305.0655, 263.0478 | EGC-Ph |
3.35 | 415.1024 | 415.1024 | −0.06 | 288.9869, 271.1326, 263.0480 | C-Ph |
3.67 | 415.1025 | 415.1024 | 0.27 | 288.9869, 271.1326, 263.0480 | EC-Ph |
4.18 | 307.0818 | 307.0812 | 1.89 | 181.0490 | EGC |
5.30 | 291.0862 | 291.0863 | −0.56 | 273.0747, 165.0544 | C |
6.00 | 291.0862 | 291.0863 | −0.56 | 273.0747, 165.0544 | EC |
Fraction | Terminal Unit (%) | Extension Unit (%) | mDP | ||||
---|---|---|---|---|---|---|---|
C | EC | EGC | C-Ph | EC-Ph | EGC-Ph | ||
WRPs-1 | 15.15 ± 0.30 a | 11.83 ± 0.42 a | 9.55 ± 0.33 a | 15.87 ± 0.31 d | 44.03 ± 0.53 e | 3.57 ± 0.11 b | 2.66 ± 0.04 f |
WRPs-2 | 8.95 ± 0.32 b | 9.62 ± 0.11 b | 4.35 ± 0.05 b | 22.89 ± 0.26 a | 49.91 ± 0.46 d | 3.28 ± 0.09 c | 4.32 ± 0.06 e |
WRPs-3 | 9.69 ± 0.47 b | 6.55 ± 0.13 c | 4.55 ± 0.04 b | 20.43 ± 0.24 b | 55.62 ± 0.59 c | 3.16 ± 0.12 cd | 4.81 ± 0.09 d |
WRPs-4 | 7.52 ± 0.48 c | 6.60 ± 0.32 c | 3.19 ± 0.17 c | 16.79 ± 0.45 c | 63.03 ± 0.80 b | 2.87 ± 0.08 e | 5.78 ± 0.12 c |
WRPs-5 | 6.01 ± 0.28 d | 4.83 ± 0.09 d | 4.45 ± 0.12 b | 16.92 ± 0.31 c | 64.71 ± 0.65 b | 3.08 ± 0.15 d | 6.54 ± 0.23 b |
WRPs-6 | 4.21 ± 0.12 e | 3.80 ± 0.06 e | 1.70 ± 0.04 d | 15.79 ± 0.21 d | 70.63 ± 0.69 a | 3.87 ± 0.10 a | 10.30 ± 0.46 a |
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Chu, M.-J.; Du, Y.-M.; Liu, X.-M.; Yan, N.; Wang, F.-Z.; Zhang, Z.-F. Extraction of Proanthocyanidins from Chinese Wild Rice (Zizania latifolia) and Analyses of Structural Composition and Potential Bioactivities of Different Fractions. Molecules 2019, 24, 1681. https://doi.org/10.3390/molecules24091681
Chu M-J, Du Y-M, Liu X-M, Yan N, Wang F-Z, Zhang Z-F. Extraction of Proanthocyanidins from Chinese Wild Rice (Zizania latifolia) and Analyses of Structural Composition and Potential Bioactivities of Different Fractions. Molecules. 2019; 24(9):1681. https://doi.org/10.3390/molecules24091681
Chicago/Turabian StyleChu, Mei-Jun, Yong-Mei Du, Xin-Min Liu, Ning Yan, Feng-Zhong Wang, and Zhong-Feng Zhang. 2019. "Extraction of Proanthocyanidins from Chinese Wild Rice (Zizania latifolia) and Analyses of Structural Composition and Potential Bioactivities of Different Fractions" Molecules 24, no. 9: 1681. https://doi.org/10.3390/molecules24091681