Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study
The essential oils (OEs) of the leaves, stems, and spikes of <i>P. marginatum</i> were obtained by hydrodistillation, steam distillation, and simultaneous extraction. The chemical constituents were identified and quantified by GC/MS and GC-FID. The preliminary biological activity was det...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/15/5814 |
| _version_ | 1797586259726565376 |
|---|---|
| author | Bruna de Souza Feitosa Oberdan Oliveira Ferreira Suraj N. Mali Amit Anand Jorddy Nevez Cruz Celeste de Jesus Pereira Franco Sonu Kumar Mahawer Ravendra Kumar Marcia Moraes Cascaes Mozaniel Santana de Oliveira Eloisa Helena de Aguiar Andrade |
| author_facet | Bruna de Souza Feitosa Oberdan Oliveira Ferreira Suraj N. Mali Amit Anand Jorddy Nevez Cruz Celeste de Jesus Pereira Franco Sonu Kumar Mahawer Ravendra Kumar Marcia Moraes Cascaes Mozaniel Santana de Oliveira Eloisa Helena de Aguiar Andrade |
| author_sort | Bruna de Souza Feitosa |
| collection | DOAJ |
| description | The essential oils (OEs) of the leaves, stems, and spikes of <i>P. marginatum</i> were obtained by hydrodistillation, steam distillation, and simultaneous extraction. The chemical constituents were identified and quantified by GC/MS and GC-FID. The preliminary biological activity was determined by assessing the toxicity of the samples to <i>Artemia salina</i> Leach larvae and calculating the mortality rate and lethal concentration (LC<sub>50</sub>). The antioxidant activity of the EOs was determined by the DPPH radical scavenging method. Molecular modeling was performed using molecular docking and molecular dynamics, with acetylcholinesterase being the molecular target. The OES yields ranged from 1.49% to 1.83%. The EOs and aromatic constituents of <i>P. marginatum</i> are characterized by the high contents of (<i>E</i>)-isoosmorhizole (19.4–32.9%), 2-methoxy-4,5-methylenedioxypropiophenone (9.0–19.9%), isoosmorhizole (1.6–24.5%), and 2-methoxy-4,5-methylenedioxypropiophenone isomer (1.6–14.3%). The antioxidant potential was significant in the OE of the leaves and stems of <i>P. marginatum</i> extracted by SD in November (84.9 ± 4.0 mg TE·mL<sup>−1</sup>) and the OEs of the leaves extracted by HD in March (126.8 ± 12.3 mg TE·mL<sup>−1</sup>). Regarding the preliminary toxicity, the OEs of Pm-SD-L-St-Nov and Pm-HD-L-St-Nov had mortality higher than 80% in concentrations of 25 µg·mL<sup>−1</sup>. This in silico study on essential oils elucidated the potential mechanism of interaction of the main compounds, which may serve as a basis for advances in this line of research. |
| first_indexed | 2024-03-11T00:20:49Z |
| format | Article |
| id | doaj.art-bd7c9ee4530f4632b1d8b2e6a6310ca1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T00:20:49Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-bd7c9ee4530f4632b1d8b2e6a6310ca12023-11-18T23:19:13ZengMDPI AGMolecules1420-30492023-08-012815581410.3390/molecules28155814Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling StudyBruna de Souza Feitosa0Oberdan Oliveira Ferreira1Suraj N. Mali2Amit Anand3Jorddy Nevez Cruz4Celeste de Jesus Pereira Franco5Sonu Kumar Mahawer6Ravendra Kumar7Marcia Moraes Cascaes8Mozaniel Santana de Oliveira9Eloisa Helena de Aguiar Andrade10School of Chemistry, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilGraduate Program in Biodiversity and Biotechnology—Rede Bionorte, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilDepartment of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Ranchi 835215, IndiaDepartment of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Ranchi 835215, IndiaSchool of Chemistry, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilSchool of Chemistry, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilDepartment of Chemistry, College of Basic Sciences and Humanities, Govind Ballabh Pant University of Agriculture and Technology, Pantnagar 263145, IndiaDepartment of Chemistry, College of Basic Sciences and Humanities, Govind Ballabh Pant University of Agriculture and Technology, Pantnagar 263145, IndiaGraduate Program in Chemistry, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilPrograma de Pós-Graduação em Ciências Biológicas—Botânica Tropical, Universidade Federal Rural da Amazônia, Museu Paraense Emílio Goeldi, Av. Perimetral, 1901, Terra Firme, Belém 66077-830, PA, BrazilSchool of Chemistry, Universidade Federal do Pará, Rua Augusto Corrêa S/N, Guamá, Belém 66075-900, PA, BrazilThe essential oils (OEs) of the leaves, stems, and spikes of <i>P. marginatum</i> were obtained by hydrodistillation, steam distillation, and simultaneous extraction. The chemical constituents were identified and quantified by GC/MS and GC-FID. The preliminary biological activity was determined by assessing the toxicity of the samples to <i>Artemia salina</i> Leach larvae and calculating the mortality rate and lethal concentration (LC<sub>50</sub>). The antioxidant activity of the EOs was determined by the DPPH radical scavenging method. Molecular modeling was performed using molecular docking and molecular dynamics, with acetylcholinesterase being the molecular target. The OES yields ranged from 1.49% to 1.83%. The EOs and aromatic constituents of <i>P. marginatum</i> are characterized by the high contents of (<i>E</i>)-isoosmorhizole (19.4–32.9%), 2-methoxy-4,5-methylenedioxypropiophenone (9.0–19.9%), isoosmorhizole (1.6–24.5%), and 2-methoxy-4,5-methylenedioxypropiophenone isomer (1.6–14.3%). The antioxidant potential was significant in the OE of the leaves and stems of <i>P. marginatum</i> extracted by SD in November (84.9 ± 4.0 mg TE·mL<sup>−1</sup>) and the OEs of the leaves extracted by HD in March (126.8 ± 12.3 mg TE·mL<sup>−1</sup>). Regarding the preliminary toxicity, the OEs of Pm-SD-L-St-Nov and Pm-HD-L-St-Nov had mortality higher than 80% in concentrations of 25 µg·mL<sup>−1</sup>. This in silico study on essential oils elucidated the potential mechanism of interaction of the main compounds, which may serve as a basis for advances in this line of research.https://www.mdpi.com/1420-3049/28/15/5814natural products<i>Piperaceae</i>Amazon<i>Artemia salina</i>volatile oilin silico study |
| spellingShingle | Bruna de Souza Feitosa Oberdan Oliveira Ferreira Suraj N. Mali Amit Anand Jorddy Nevez Cruz Celeste de Jesus Pereira Franco Sonu Kumar Mahawer Ravendra Kumar Marcia Moraes Cascaes Mozaniel Santana de Oliveira Eloisa Helena de Aguiar Andrade Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study Molecules natural products <i>Piperaceae</i> Amazon <i>Artemia salina</i> volatile oil in silico study |
| title | Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study |
| title_full | Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study |
| title_fullStr | Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study |
| title_full_unstemmed | Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study |
| title_short | Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of <i>Piper marginatum</i> Sensu Lato Essential Oils and Molecular Modeling Study |
| title_sort | chemical composition preliminary toxicity and antioxidant potential of i piper marginatum i sensu lato essential oils and molecular modeling study |
| topic | natural products <i>Piperaceae</i> Amazon <i>Artemia salina</i> volatile oil in silico study |
| url | https://www.mdpi.com/1420-3049/28/15/5814 |
| work_keys_str_mv | AT brunadesouzafeitosa chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT oberdanoliveiraferreira chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT surajnmali chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT amitanand chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT jorddynevezcruz chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT celestedejesuspereirafranco chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT sonukumarmahawer chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT ravendrakumar chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT marciamoraescascaes chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT mozanielsantanadeoliveira chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy AT eloisahelenadeaguiarandrade chemicalcompositionpreliminarytoxicityandantioxidantpotentialofipipermarginatumisensulatoessentialoilsandmolecularmodelingstudy |