Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities
Extracts of <i>Peperomia pellucida</i> [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this st...
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MDPI AG
2020-10-01
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| author | I Gusti Agung Ayu Kartika In Jae Bang Catur Riani Muhamad Insanu Jong Hwan Kwak Kyu Hyuck Chung I Ketut Adnyana |
| author_facet | I Gusti Agung Ayu Kartika In Jae Bang Catur Riani Muhamad Insanu Jong Hwan Kwak Kyu Hyuck Chung I Ketut Adnyana |
| author_sort | I Gusti Agung Ayu Kartika |
| collection | DOAJ |
| description | Extracts of <i>Peperomia pellucida</i> [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate and elucidate potential compounds with estrogenic activity. The structures of the isolated compounds were identified using 1D <sup>1</sup>H and <sup>13</sup>C-NMR and confirmed by 2D FT-NMR. The estrogenic activity was evaluated using the E-SCREEN assay, and a molecular docking study was performed to predict the binding affinity of the isolated compounds to estrogen receptors. In this experiment, we successfully isolated three phenylpropanoids and two lignan derivatives, namely, 6-allyl-5-methoxy-1,3-benzodioxol-4-ol (<b>1</b>), pachypostaudin B (<b>2</b>), pellucidin A (<b>3</b>), dillapiole (<b>4</b>), and apiol (<b>5</b>). Among these compounds, the isolation of <b>1</b> and <b>2</b> from <i>P. pellucida</i> is reported for the first time in this study. Activity assays clearly showed that the ethyl acetate extract and its fractions, subfractions, and isolated compounds exerted estrogenic activity. Methanol fraction of the ethyl acetate extract produced the highest estrogenic activity, while <b>1</b> and <b>2</b> had partial agonist activity. Some compounds (derivates of dillapiole and pellucidin A) also had, in addition, anti-estrogenic activity. In the docking study, the estrogenic activities of <b>1</b>–<b>5</b> appeared to be mediated by a classical ligand-dependent mechanism as suggested by the binding interaction between the compounds and estrogen receptors; binding occurred on Arg 394 and His 524 of the alpha receptor and Arg 346 and His 475 of the beta receptor. In summary, we reveal that <i>P. pellucida</i> is a promising anti-osteoporotic agent due to its estrogenic activity, and the compounds responsible for this activity were found to be lignan and phenylpropanoid derivatives. The presence of other compounds in either the extract or fraction may contribute to a synergistic effect, as suggested by the higher estrogenic activity of the methanol fraction. Hence, we suggest further research on the osteoporotic activity and safety of the identified compounds, especially regarding their effects on estrogen-responsive organs. |
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| spelling | doaj.art-5c44b2a839fb4c22a2fac44dff4134702023-11-20T18:21:46ZengMDPI AGMolecules1420-30492020-10-012521491410.3390/molecules25214914Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic ActivitiesI Gusti Agung Ayu Kartika0In Jae Bang1Catur Riani2Muhamad Insanu3Jong Hwan Kwak4Kyu Hyuck Chung5I Ketut Adnyana6Pharmacology and Clinical Pharmacy Department, School of Pharmacy, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, IndonesiaPrevent Pharm Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon-Si, Gyeonggi-Do 16419, KoreaLaboratory of Pharmaceutical Biotechnology, School of Pharmacy, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, IndonesiaPharmaceutical Biology Department, School of Pharmacy, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, IndonesiaPhytochemistry Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon-Si, Gyeonggi-Do 16419, KoreaPrevent Pharm Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon-Si, Gyeonggi-Do 16419, KoreaPharmacology and Clinical Pharmacy Department, School of Pharmacy, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, IndonesiaExtracts of <i>Peperomia pellucida</i> [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate and elucidate potential compounds with estrogenic activity. The structures of the isolated compounds were identified using 1D <sup>1</sup>H and <sup>13</sup>C-NMR and confirmed by 2D FT-NMR. The estrogenic activity was evaluated using the E-SCREEN assay, and a molecular docking study was performed to predict the binding affinity of the isolated compounds to estrogen receptors. In this experiment, we successfully isolated three phenylpropanoids and two lignan derivatives, namely, 6-allyl-5-methoxy-1,3-benzodioxol-4-ol (<b>1</b>), pachypostaudin B (<b>2</b>), pellucidin A (<b>3</b>), dillapiole (<b>4</b>), and apiol (<b>5</b>). Among these compounds, the isolation of <b>1</b> and <b>2</b> from <i>P. pellucida</i> is reported for the first time in this study. Activity assays clearly showed that the ethyl acetate extract and its fractions, subfractions, and isolated compounds exerted estrogenic activity. Methanol fraction of the ethyl acetate extract produced the highest estrogenic activity, while <b>1</b> and <b>2</b> had partial agonist activity. Some compounds (derivates of dillapiole and pellucidin A) also had, in addition, anti-estrogenic activity. In the docking study, the estrogenic activities of <b>1</b>–<b>5</b> appeared to be mediated by a classical ligand-dependent mechanism as suggested by the binding interaction between the compounds and estrogen receptors; binding occurred on Arg 394 and His 524 of the alpha receptor and Arg 346 and His 475 of the beta receptor. In summary, we reveal that <i>P. pellucida</i> is a promising anti-osteoporotic agent due to its estrogenic activity, and the compounds responsible for this activity were found to be lignan and phenylpropanoid derivatives. The presence of other compounds in either the extract or fraction may contribute to a synergistic effect, as suggested by the higher estrogenic activity of the methanol fraction. Hence, we suggest further research on the osteoporotic activity and safety of the identified compounds, especially regarding their effects on estrogen-responsive organs.https://www.mdpi.com/1420-3049/25/21/4914<i>Peperomia pellucida</i>phenylpropanoid and lignanphytoestrogenE-SCREENdocking |
| spellingShingle | I Gusti Agung Ayu Kartika In Jae Bang Catur Riani Muhamad Insanu Jong Hwan Kwak Kyu Hyuck Chung I Ketut Adnyana Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities Molecules <i>Peperomia pellucida</i> phenylpropanoid and lignan phytoestrogen E-SCREEN docking |
| title | Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities |
| title_full | Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities |
| title_fullStr | Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities |
| title_full_unstemmed | Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities |
| title_short | Isolation and Characterization of Phenylpropanoid and Lignan Compounds from <i>Peperomia pellucida</i> [L.] Kunth with Estrogenic Activities |
| title_sort | isolation and characterization of phenylpropanoid and lignan compounds from i peperomia pellucida i l kunth with estrogenic activities |
| topic | <i>Peperomia pellucida</i> phenylpropanoid and lignan phytoestrogen E-SCREEN docking |
| url | https://www.mdpi.com/1420-3049/25/21/4914 |
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