Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A
The phytochemical research on the species <i>Siparuna echinata</i>, collected in the Province of Loja (Ecuador), led to the isolation of a rare sesquiterpenoid, called Sipaucin A. The structure was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Furthermore, the...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-02-01
|
| Series: | Plants |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2223-7747/9/2/187 |
| _version_ | 1819278259140952064 |
|---|---|
| author | Jessica García Gianluca Gilardoni Nixon Cumbicus Vladimir Morocho |
| author_facet | Jessica García Gianluca Gilardoni Nixon Cumbicus Vladimir Morocho |
| author_sort | Jessica García |
| collection | DOAJ |
| description | The phytochemical research on the species <i>Siparuna echinata</i>, collected in the Province of Loja (Ecuador), led to the isolation of a rare sesquiterpenoid, called Sipaucin A. The structure was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Furthermore, the essential oil of the fruits was obtained by hydrodistillation and analyzed by gas chromatography, coupled to mass spectrometry (GC-MS) and flame ionization detector (GC-FID). Twenty-seven compounds were identified in a polydimethylsiloxane column (DB-5ms) and nineteen in a polyethylene glycol column (HP-INNOWax). Major compounds were α-pinene (24.3%, 20.3%), β-pinene (21.7%, 22.7%), β-myrcene (11.3%, 14.8%), limonene (10.0%, 11.3%), <i>cis</i>-ocimene (8.5%, 8.1%), and <i>trans</i>-ocimene (8.9%, 8.4%). In addition to the chemical analysis, the essential oil was submitted to enantioselective analysis of two major chiral monotherpenes, determining an enantiomeric excess of 100.0% for (+)-α-pinene and 6.7% for (+)-β-pinene. |
| first_indexed | 2024-12-24T00:09:10Z |
| format | Article |
| id | doaj.art-703052bc037244cf980ab54115322815 |
| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-12-24T00:09:10Z |
| publishDate | 2020-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Plants |
| spelling | doaj.art-703052bc037244cf980ab541153228152022-12-21T17:24:56ZengMDPI AGPlants2223-77472020-02-019218710.3390/plants9020187plants9020187Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin AJessica García0Gianluca Gilardoni1Nixon Cumbicus2Vladimir Morocho3Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja 1101608, EcuadorDepartamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja 1101608, EcuadorDepartamento de Ciencias Biológicas, Universidad Técnica Particular de Loja (UTPL), Loja 1101608, EcuadorDepartamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja 1101608, EcuadorThe phytochemical research on the species <i>Siparuna echinata</i>, collected in the Province of Loja (Ecuador), led to the isolation of a rare sesquiterpenoid, called Sipaucin A. The structure was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Furthermore, the essential oil of the fruits was obtained by hydrodistillation and analyzed by gas chromatography, coupled to mass spectrometry (GC-MS) and flame ionization detector (GC-FID). Twenty-seven compounds were identified in a polydimethylsiloxane column (DB-5ms) and nineteen in a polyethylene glycol column (HP-INNOWax). Major compounds were α-pinene (24.3%, 20.3%), β-pinene (21.7%, 22.7%), β-myrcene (11.3%, 14.8%), limonene (10.0%, 11.3%), <i>cis</i>-ocimene (8.5%, 8.1%), and <i>trans</i>-ocimene (8.9%, 8.4%). In addition to the chemical analysis, the essential oil was submitted to enantioselective analysis of two major chiral monotherpenes, determining an enantiomeric excess of 100.0% for (+)-α-pinene and 6.7% for (+)-β-pinene.https://www.mdpi.com/2223-7747/9/2/187<i>siparuna echinata</i>essential oilenantioselective analysissipaucin aecuador |
| spellingShingle | Jessica García Gianluca Gilardoni Nixon Cumbicus Vladimir Morocho Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A Plants <i>siparuna echinata</i> essential oil enantioselective analysis sipaucin a ecuador |
| title | Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A |
| title_full | Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A |
| title_fullStr | Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A |
| title_full_unstemmed | Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A |
| title_short | Chemical Analysis of the Essential Oil from <i>Siparuna echinata</i> (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A |
| title_sort | chemical analysis of the essential oil from i siparuna echinata i kunth a dc siparunaceae of ecuador and isolation of the rare terpenoid sipaucin a |
| topic | <i>siparuna echinata</i> essential oil enantioselective analysis sipaucin a ecuador |
| url | https://www.mdpi.com/2223-7747/9/2/187 |
| work_keys_str_mv | AT jessicagarcia chemicalanalysisoftheessentialoilfromisiparunaechinataikunthadcsiparunaceaeofecuadorandisolationoftherareterpenoidsipaucina AT gianlucagilardoni chemicalanalysisoftheessentialoilfromisiparunaechinataikunthadcsiparunaceaeofecuadorandisolationoftherareterpenoidsipaucina AT nixoncumbicus chemicalanalysisoftheessentialoilfromisiparunaechinataikunthadcsiparunaceaeofecuadorandisolationoftherareterpenoidsipaucina AT vladimirmorocho chemicalanalysisoftheessentialoilfromisiparunaechinataikunthadcsiparunaceaeofecuadorandisolationoftherareterpenoidsipaucina |