Dataset Information

Chemical Analysis of the Essential Oil from Siparuna echinata (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A.

ABSTRACT: The phytochemical research on the species Siparuna echinata, 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 ?-pinene (24.3%, 20.3%), ?-pinene (21.7%, 22.7%), ?-myrcene (11.3%, 14.8%), limonene (10.0%, 11.3%), cis-ocimene (8.5%, 8.1%), and trans-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 (+)-?-pinene and 6.7% for (+)-?-pinene.

SUBMITTER: Garcia J

PROVIDER: S-EPMC7076530 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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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.

García Jessica J Gilardoni Gianluca G Cumbicus Nixon N Morocho Vladimir V

Plants (Basel, Switzerland) 20200204 2

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 identifi ...[more]

PMID: 32033003

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Project description:Medicinal plants play a crucial role in the search for components that are capable of neutralizing the multiple mechanisms of fungal resistance. Psidium salutare (Kunth) O. Berg is a plant native to Brazil used as both food and traditional medicine to treat diseases and symptoms such as stomach ache and diarrhea, whose symptoms could be related to fungal infections from the genus Candida. The objective of this study was to investigate the influence of seasonal variability on the chemical composition of the Psidium salutare essential oil, its antifungal potential and its effect on the Candida albicans morphogenesis. The essential oils were collected in three different seasonal collection periods and isolated by the hydrodistillation process in a modified Clevenger apparatus with identification of the chemical composition determined by gas chromatography coupled to mass spectrometry (GC/MS). The antifungal assays were performed against Candida strains through the broth microdilution method to determine the minimum fungicidal concentration (MFC). Fungal growth was assessed by optical density reading and the Candida albicans dimorphic effect was evaluated by optical microscopy in microculture chambers. The chemical profile of the essential oils identified 40 substances in the different collection periods with γ-terpinene being the predominant constituent. The antifungal activity revealed an action against the C. albicans, C. krusei and C. tropicalis strains with an IC50 ranging from 345.5 to 2,754.2 µg/mL and a MFC higher than 1,024 µg/mL. When combined with essential oils at sub-inhibitory concentrations (MIC/16), fluconazole had its potentiated effect, i.e. a synergistic effect was observed in the combination of fluconazole with P.salutare oil against all Candida strains; however, for C. albicans, its effect was reinforced by the natural product in all the collection periods. The results show that the Psidium salutare oil affected the dimorphic transition capacity, significantly reducing the formation of hyphae and pseudohyphae in increasing concentrations. The results show that P. salutare oil exhibits a significant antifungal activity against three Candida species and that it can act in synergy with fluconazole. These results support the notion that this plant may have a potential use in pharmaceutical and preservative products.

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Dataset Information

Chemical Analysis of the Essential Oil from Siparuna echinata (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A.

Publications

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.

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