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Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum
The essential oil and the major non-volatile secondary metabolites from the leaves of Piper subscutatum (Miq.) C. DC. (Family Piperaceae), collected in the Ecuadorian Amazon, were analyzed for the first time in the present study. The essential oil was submitted to chemical and enantioselective analy...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8228786/ https://www.ncbi.nlm.nih.gov/pubmed/34207495 http://dx.doi.org/10.3390/plants10061168 |
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author | Ramírez, Jorge Andrade, María Daniela Vidari, Giovanni Gilardoni, Gianluca |
author_facet | Ramírez, Jorge Andrade, María Daniela Vidari, Giovanni Gilardoni, Gianluca |
author_sort | Ramírez, Jorge |
collection | PubMed |
description | The essential oil and the major non-volatile secondary metabolites from the leaves of Piper subscutatum (Miq.) C. DC. (Family Piperaceae), collected in the Ecuadorian Amazon, were analyzed for the first time in the present study. The essential oil was submitted to chemical and enantioselective analyses by GC-MS and GC-FID. (E)-β-caryophyllene (25.3–25.2%), β-chamigrene (10.3–7.8%), (E)-nerolidol (8.1–7.7%), β-selinene (7.2–7.7%), δ-cadinene (2.7–3.9%), bicyclogermacrene (3.7–2.4%), and β-pinene (2.6–3.4%) were the major components. The enantioselective analysis, carried out on a β-cyclodextrin-based column, showed four scalemic mixtures in which (1R,5R)-(+)-α-pinene, (1S,5S)-(−)-β-pinene, (S)-(−)-limonene, and (1R,2S,6S,7S,8S)-(−)-α-copaene were the major enantiomers, with enantiomeric excesses of 28.8%, 77.8%, 18.4%, and 6.0%, respectively. The study was complemented with the chemical analysis of the organic fraction dissolved in the hydrolate, whose major components were 6-methyl-5-hepten-2-one (63.7–64.4%) and linalool (6.5–6.0%). Concerning the non-volatile fraction, five lignans were the major components. (–)-Beilshminol B, (–)-grandisin, (–)-3′,4′-methylenedioxy-3,4,5-trimethoxy-7,7′-epoxylignan, (–)-3′,4′-methylenedioxy-3,4,5,5′-tetramethoxy-7,7′-epoxylignan, and (–)-3,4,3′,4′-dimethylenedioxy-5,5′-dimethoxy-7,7′-epoxylignan were identified by means of NMR spectroscopy, mass spectrometry and X-ray crystallography. The absolute configuration 7S,8S,7′S,8′S was tentatively assigned to all of them. |
format | Online Article Text |
id | pubmed-8228786 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-82287862021-06-26 Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum Ramírez, Jorge Andrade, María Daniela Vidari, Giovanni Gilardoni, Gianluca Plants (Basel) Article The essential oil and the major non-volatile secondary metabolites from the leaves of Piper subscutatum (Miq.) C. DC. (Family Piperaceae), collected in the Ecuadorian Amazon, were analyzed for the first time in the present study. The essential oil was submitted to chemical and enantioselective analyses by GC-MS and GC-FID. (E)-β-caryophyllene (25.3–25.2%), β-chamigrene (10.3–7.8%), (E)-nerolidol (8.1–7.7%), β-selinene (7.2–7.7%), δ-cadinene (2.7–3.9%), bicyclogermacrene (3.7–2.4%), and β-pinene (2.6–3.4%) were the major components. The enantioselective analysis, carried out on a β-cyclodextrin-based column, showed four scalemic mixtures in which (1R,5R)-(+)-α-pinene, (1S,5S)-(−)-β-pinene, (S)-(−)-limonene, and (1R,2S,6S,7S,8S)-(−)-α-copaene were the major enantiomers, with enantiomeric excesses of 28.8%, 77.8%, 18.4%, and 6.0%, respectively. The study was complemented with the chemical analysis of the organic fraction dissolved in the hydrolate, whose major components were 6-methyl-5-hepten-2-one (63.7–64.4%) and linalool (6.5–6.0%). Concerning the non-volatile fraction, five lignans were the major components. (–)-Beilshminol B, (–)-grandisin, (–)-3′,4′-methylenedioxy-3,4,5-trimethoxy-7,7′-epoxylignan, (–)-3′,4′-methylenedioxy-3,4,5,5′-tetramethoxy-7,7′-epoxylignan, and (–)-3,4,3′,4′-dimethylenedioxy-5,5′-dimethoxy-7,7′-epoxylignan were identified by means of NMR spectroscopy, mass spectrometry and X-ray crystallography. The absolute configuration 7S,8S,7′S,8′S was tentatively assigned to all of them. MDPI 2021-06-09 /pmc/articles/PMC8228786/ /pubmed/34207495 http://dx.doi.org/10.3390/plants10061168 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Ramírez, Jorge Andrade, María Daniela Vidari, Giovanni Gilardoni, Gianluca Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title | Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title_full | Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title_fullStr | Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title_full_unstemmed | Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title_short | Essential Oil and Major Non-Volatile Secondary Metabolites from the Leaves of Amazonian Piper subscutatum |
title_sort | essential oil and major non-volatile secondary metabolites from the leaves of amazonian piper subscutatum |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8228786/ https://www.ncbi.nlm.nih.gov/pubmed/34207495 http://dx.doi.org/10.3390/plants10061168 |
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