Microwave- and Ultrasound-Assisted Extraction of Cucurbitane-Type Triterpenoids from Momordica charantia L. Cultivars and Their Antiproliferative Effect on SAS Human Oral Cancer Cells
Abstract
:1. Introduction
2. Materials and Method
2.1. Chemicals and Reagents
2.2. Sample Preparation and Extraction
2.2.1. Plant Materials
2.2.2. Ultrasound-Assisted Extraction
2.2.3. Microwave-Assisted Extraction
2.3. Solid Phase Extraction Process Test
2.4. UHPLC–MS/MS Analysis
2.5. Method Validation Assay
2.6. Cell Culture
2.7. Cell Proliferation Assay
2.8. Statistical Analysis
3. Results and Discussion
3.1. Solid Phase Extraction Process
3.2. Method Validation
3.3. Comparison of Ultrasound-Assisted Extraction and Microwave-Assisted Extraction
3.4. Application of Microwave-Assisted Extraction on Six Different Wild Bitter Melons
3.5. 3β,7β,25-Trihydroxycucurbita-5,23(E)-dien-19-al and Momordicine I Suppressed the Proliferation of SAS Cells
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | Molecular Weight (g/mol) | Quantitative | Qualitative | ||||
---|---|---|---|---|---|---|---|
Parent Ions * > Product Ions (m/z) | Cone Voltage (V) | Collision Energy (eV) | Parent Ions * > Product Ions (m/z) | Cone Voltage (V) | Collision Energy (eV) | ||
Momordicoside A | 817.01 | 839 > 839 | 91 | 44 | 839 > 365 | 91 | 57 |
Momordicoside L | 634.40 | 657 > 477 | 78 | 41 | 657 > 203 | 78 | 43 |
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al | 472.40 | 495 > 495 | 93 | 13 | 495 > 477 | 93 | 35 |
Momordicoside K | 648.40 | 671 > 203 | 87 | 43 | 671 > 491 | 87 | 43 |
Momordicine Ⅰ | 472.70 | 495 > 495 | 61 | 3 | 495 > 477 | 61 | 33 |
Momordicoside I | 618.40 | 641 > 337 | 94 | 46 | 641 > 203 | 94 | 52 |
Momordicoside F2 | 618.40 | 641 > 337 | 94 | 46 | 641 > 203 | 94 | 52 |
Momordicoside I aglycone | 456.72 | 479 > 479 | 50 | 18 | - | - | - |
Momordicoside G | 632.42 | 655 > 625 | 68 | 42 | 655 > 337 | 68 | 38 |
Momordicoside F1 | 632.42 | 655 > 625 | 17 | 51 | 655 > 337 | 17 | 57 |
Compound | Linear Range (ng/mL) | Retention Time (min) | r | Calibration Curve | LOD (ng/mL) | LOQ (ng/mL) | Interday Recovery (%) | Interday (CV %) |
---|---|---|---|---|---|---|---|---|
Momordicoside A | 2–200 | 1.04 | 0.9989 | y = 142.41 x + 148.41 | 0.125 | 0.25 | 100.2 ± 4.7 | 7.77 |
Momordicoside L | 2–200 | 3.01 | 0.9973 | y = 204.67 x − 242.72 | 0.50 | 1.00 | 113.1 ± 5.7 | 12.19 |
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al | 2–200 | 4.26 | 0.9977 | y = 11,142.59 x − 14,020.99 | 0.50 | 1.00 | 110.9 ± 6.3 | 14.52 |
Momordicoside K | 2–200 | 6.24 | 0.9991 | y = 213.17 x − 571.18 | 1.50 | 2.00 | 95.5 ± 7.3 | 13.09 |
Momordicine Ⅰ | 20–200 | 6.72 | 0.9941 | y = 1444.18 x + 4685.53 | 10.00 | 15.00 | 101.5 ± 10.6 | 14.21 |
Momordicoside I | 20–200 | 6.88 | 0.9961 | y = 27.70 x + 62.06 | 3.00 | 10.00 | 99.1 ± 6.1 | 12.33 |
Momordicoside F2 | 20–200 | 7.11 | 0.9921 | y = 29.99 x − 189.06 | 3.00 | 10.00 | 85.5 ± 10.7 | 14.36 |
Momordicoside I aglycone | 20–200 | 8.54 | 0.9917 | y = 652.41 x + 479.97 | 3.00 | 10.00 | 103.0 ± 4.0 | 14.69 |
Momordicoside G | 2–200 | 9.42 | 0.9976 | y = 30.60 x + 3.14 | 1.50 | 2.00 | 106.5 ± 6.6 | 14.23 |
Momordicoside F1 | 2–200 | 9.31 | 0.9965 | y = 107.45 x + 184.30 | 0.25 | 0.50 | 115.3 ± 3.7 | 12.82 |
Compound | Contents (μg/g) | |||||
---|---|---|---|---|---|---|
No. 1 | No. 2 | No. 3 | No. 4 | No. 5 | No. 6 | |
Momordicoside A | 358.59 ± 18.12 A,x | 339.61 ± 31.92 A,x | 195.55 ± 6.88 A,y | 379.37 ± 27.53 B,x | 1261.6 ± 51.54 A,w | 11.64 ± 0.60 B,z |
Momordicine I | 24.78 ± 4.93 B,z | 94.08 ± 16.81 B,y | 141.35 ± 6.34 B,x | 470.01 ± 25.03 A,w | 155.83 ± 11.20 B,x | 43.93 ± 3.60 A,z |
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al | 1.89 ± 0.13 D,z | 4.03 ± 0.14 C,z | 6.94 ± 0.38 D,E,z | 189.84 ± 7.80 C,x | 37.67 ± 1.36 C,y | 4.15 ± 0.12 E,z |
Momordicoside K | 4.17 ± 1.31 C,D,y,z | 5.31 ± 1.33 C,y,z | 9.71 ± 2.05 D,x | 5.71 ± 0.47 E,y | 3.40 ± 0.52 D,z | 3.95 ± 0.65 E,y,z |
Momordicoside L | 10.15 ± 2.03 C,x,y | 12.32 ± 3.15 C,x | 61.15 ± 5.32 C,w | 7.16 ± 1.12 E,z | 14.54 ± 2.26 D,x | 10.74 ± 1.90 B,x,y |
Momordicoside I aglycone | N. D. * | N. D. | N. D. | N. D. | N. D. | N. D. |
Momordicoside I | 1.15 ± 0.18 D,z | 0.60 ± 0.71 C,z | 3.56 ± 0.62 E,F,y | 9.84 ± 0.73 E,x | 17.66 ± 0.85 D,w | 1.47 ± 0.38 F,z |
Momordicoside F2 | 3.06 ± 0.42 D,z | 3.30 ± 0.30 C,z | 6.14 ± 0.28 D,E,y | 75.63 ± 3.33 D,w | 11.44 ± 0.81 D,x | 6.27 ± 0.32 D,y |
Momordicoside F1 | 0.43 ± 0.10 D,y,z | 0.42 ± 0.15 C,y,z | 0.65 ± 0.18 F,y | 1.27 ± 0.24 E,x | 1.44 ± 0.23 D,x | 0.24 ± 0.16 F,z |
Momordicoside G | 6.68 ± 2.57 C,D,z | 6.36 ± 2.68 C,z | 7.74 ± 1.51 D,z | 11.49 ± 1.74 E,y | 6.11 ± 0.63 D,z | 8.20 ± 2.11 C,z |
Total | 410.91 ± 21.08 y | 466.04 ± 48.91 y | 432.79 ± 16.52 y | 1150.31 ± 52.06 x | 1509.71 ± 55.97 w | 90.58 ± 7.57 z |
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Lee, Y.-T.; Pao, L.-H.; Chen, C.-Y.; Huang, S.-Q.; Kumaran, A.; Chyuan, J.-H.; Chiu, C.-H. Microwave- and Ultrasound-Assisted Extraction of Cucurbitane-Type Triterpenoids from Momordica charantia L. Cultivars and Their Antiproliferative Effect on SAS Human Oral Cancer Cells. Foods 2022, 11, 729. https://doi.org/10.3390/foods11050729
Lee Y-T, Pao L-H, Chen C-Y, Huang S-Q, Kumaran A, Chyuan J-H, Chiu C-H. Microwave- and Ultrasound-Assisted Extraction of Cucurbitane-Type Triterpenoids from Momordica charantia L. Cultivars and Their Antiproliferative Effect on SAS Human Oral Cancer Cells. Foods. 2022; 11(5):729. https://doi.org/10.3390/foods11050729
Chicago/Turabian StyleLee, Yu-Tsung, Li-Heng Pao, Chi-Yuan Chen, Sui-Qing Huang, Alaganandam Kumaran, Jong-Ho Chyuan, and Chun-Hui Chiu. 2022. "Microwave- and Ultrasound-Assisted Extraction of Cucurbitane-Type Triterpenoids from Momordica charantia L. Cultivars and Their Antiproliferative Effect on SAS Human Oral Cancer Cells" Foods 11, no. 5: 729. https://doi.org/10.3390/foods11050729