Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities
Abstract
:1. Introduction
2. Results
2.1. Isolation and Identification of Compounds from P. pellucida Ethyl Acetate Extract
2.2. Cytotoxicity Assay
2.3. E-SCREEN Assay
2.4. Molecular Docking
3. Discussion
4. Materials and Methods
4.1. Instruments and Materials
4.2. Extraction Process
4.3. Isolation Process
4.4. Cell Lines
4.5. Cytotoxicity Assay
4.6. E-SCREEN Assay
4.7. Molecular Docking Test
4.8. Data Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Carbon Position | DEPT | HSQC | COSY | NOESY | HMBC | |
---|---|---|---|---|---|---|
C/H | 13C | 1H | ||||
1 | CH | 28.5 | 4.89 (1H, d, 8.11 Hz) | H-2 | C-2, 3, 8, 9, 10, 1a, 2a, 6a | |
2 | CH2 | 29.9 | 2.42/2.66 (2H, m) | H-1 | C-3, 4, 1a | |
3 | CH | 123.7 | 5.68 (1H, m) | H-2 | H-4 | C-2, 10 |
4 | CH | 121.3 | 6.82 (1H, dd, 3.19, 9.75 Hz) | H-2, 3 | C-2 | |
5 | C | 151.7 | ||||
6 | CH | 96.0 | 6.44 (1H, s) | H-OMe | C-5, 7, 8, 10 | |
7 | C | 152.6 | ||||
8 | C | 140.4 | ||||
9 | C | 124.6 | ||||
10 | C | 117.1 | ||||
1a | C | 132.4 | ||||
2a | C | 150.8 | ||||
3a | CH | 98.0 | 6.30 (1H, s) | H-OMe | C-2a, 4a | |
4a | C | 148.0 | ||||
5a | C | 142.5 | ||||
6a | CH | 114.4 | 6.53 (1H, s) | C-1, 2a, 4a, 5a | ||
8-OMe | CH3 | 60.6 | 3.39 (3H, s) | C-8 | ||
5a-OMe | CH3 | 57.0 | 3.57 (3H, s) | H-6a | C-5a | |
4xOMe | CH3 | 56.9, 56.4, 56.2, 56.1 | 3.84, 3.86, 3.87, 3.91 (each 3H, s) | H-6, 3a | C-5, 7, 2a, 4a |
Group of Samples | Cell Viability (in%, Mean ± SD) | ||||||||
---|---|---|---|---|---|---|---|---|---|
0.1 µg/mL | 1 µg/mL | 10 µg/mL | |||||||
Methanol Fraction | 97.15 | ± | 14.97 | 114.01 | ± | 48.88 | 118.99 | ± | 30.94 |
Petroleum Ether Fraction | 67.67 | ± | 8.09 | 72.33 | ± | 8.78 | 76.60 | ± | 12.25 |
Subfraction 1 | 101.75 | ± | 15.31 | 104.48 | ± | 18.09 | 106.23 | ± | 17.42 |
Subfraction 2 | 103.15 | ± | 52.06 | 104.41 | ± | 12.63 | 108.90 | ± | 23.77 |
Subfraction 3 | 118.42 | ± | 6.28 | 97.23 | ± | 10.37 | 81.20 | ± | 9.80 |
Subfraction 4 | 118.66 | ± | 19.22 | 95.83 | ± | 12.79 | 87.17 | ± | 0.17 |
Subfraction 5 | 80.47 | ± | 21.69 | 91.55 | ± | 20.19 | 97.91 | ± | 29.11 |
Subfraction 6 | 124.44 | ± | 23.11 | 106.25 | ± | 0.67 | 101.85 | ± | 47.25 |
Subfraction 7 | 104.56 | ± | 12.10 | 107.05 | ± | 30.85 | 115.53 | ± | 18.68 |
Subfraction 8 | 108.36 | ± | 0.87 | 109.53 | ± | 17.14 | 112.90 | ± | 33.80 |
Subfraction 9 | 111.34 | ± | 6.68 | 110.83 | ± | 6.07 | 98.07 | ± | 27.05 |
Derivate of Dillapiole | 113.95 | ± | 18.36 | 107.08 | ± | 19.05 | 101.65 | ± | 19.26 |
Pachypostaudin B | 105.43 | ± | 12.92 | 86.94 | ± | 8.93 | 82.06 | ± | 14.77 |
Pellucidin A | 88.82 | ± | 2.65 | 107.92 | ± | 11.05 | 125.56 | ± | 23.10 |
Dillapiole | 89.88 | ± | 19.04 | 105.00 | ± | 11.97 | 104.96 | ± | 4.49 |
Apiol | 116.88 | ± | 5.39 | 110.04 | ± | 33.57 | 104.68 | ± | 23.58 |
Compounds | Hydrogen Bonding (ER α) | Hydrogen Bonding (ER β) | ||||
---|---|---|---|---|---|---|
ΔG Bind (kcal/mol) | Amino Acid Residues | H-Bond Distance (Å) | ΔG Bind (kcal/mol) | Amino Acid Residues | H-Bond Distance (Å) | |
17β-Estradiol | −9.55 | ARG 394 | 2.26 | −9.55 | ARG 346 | 2.05 |
HIS 524 | 2.24 | HIS 475 | 2.16 | |||
Derivate of Dillapiole | −5.45 | - | - | −5.29 | LEU 298 | 2.09 |
Pachypostaudin B | −8.17 | HIS-524 | 3.02 | −7.03 | HIS-475 | 1.91 |
LEU-476 | 2.74 | |||||
Pellucidin A | −8.20 | HIS-524 | 3.15 | −7.65 | - | - |
Dillapiole | −5.14 | - | - | −5.26 | LEU 476 | 3.09 |
Apiol | −5.58 | ARG-394 | 3.01 | −5.44 | ARG 346 | 2.11 |
Sample Availability: Samples of the compounds are available from the authors. |
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Kartika, I.G.A.A.; Bang, I.J.; Riani, C.; Insanu, M.; Kwak, J.H.; Chung, K.H.; Adnyana, I.K. Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities. Molecules 2020, 25, 4914. https://doi.org/10.3390/molecules25214914
Kartika IGAA, Bang IJ, Riani C, Insanu M, Kwak JH, Chung KH, Adnyana IK. Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities. Molecules. 2020; 25(21):4914. https://doi.org/10.3390/molecules25214914
Chicago/Turabian StyleKartika, I Gusti Agung Ayu, In Jae Bang, Catur Riani, Muhamad Insanu, Jong Hwan Kwak, Kyu Hyuck Chung, and I Ketut Adnyana. 2020. "Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities" Molecules 25, no. 21: 4914. https://doi.org/10.3390/molecules25214914