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Chemical Analyses and Applications of Essential Oils

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: 31 January 2025 | Viewed by 9476

Special Issue Editors


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Guest Editor
Department of Pharmaceutical Microbiology, Medical University of Lublin, Chodzki Str. 1, 20-093 Lublin, Poland
Interests: medical microbiology; antimicrobial compounds of synthetic and natural origin; human microbiota
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Special Issue Information

Dear Colleagues,

Essential oils (EOs) are complex mixtures of volatile compounds obtained from materials derived mainly from aromatic plants. These natural products are particularly interesting as they exhibit a wide variety of biological effects, including antimicrobial, antiviral, antioxidant, antiamnestic, nematicidal, expectorant, anti-inflammatory, diuretic properties, etc.

The multidirectional biological properties of EOs result in their potential applications in various medicine and veterinary fields as well as in several branches of industry, such as the cosmetics, food, and agricultural industries.

The purpose of this Special Issue is to increase the knowledge of different approaches for the chemical analysis of liquid and vapor phases of EOs and the isolation of single components from the biological matrix as well as to correlate the chemical data with the bioactivity of EOs and their compounds in the aspect of the exploration of their new potential applications.

Prof. Dr. Anna Malm
Prof. Dr. Wirginia Kukula-Koch
Guest Editors

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Keywords

  • essential oils
  • bioactive compounds
  • liquid phase
  • vapor phase
  • potential applications

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Published Papers (5 papers)

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Research

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20 pages, 2429 KiB  
Article
Analysis of Chemical Composition, Antioxidant Activity, and Toxicity of Essential Oil from Virola sebifera Aubl (Myristicaceae)
by Jorddy Neves Cruz, Mozaniel Santana de Oliveira, Oberdan Oliveira Ferreira, Antonio Rafael Quadros Gomes, Suraj N. Mali, Soluan Felipe Melo Pereira, Sabah Ansar, Cleydson Breno Rodrigues dos Santos, Rafael Rodrigues Lima and Eloisa Helena Aguiar de Andrade
Molecules 2024, 29(14), 3431; https://doi.org/10.3390/molecules29143431 - 22 Jul 2024
Viewed by 1119
Abstract
Volatile oils or essential oils (EOs) were extracted from three V. sebifera samples (labeled as A, B, and C) in September 2018 and February 2019; the extraction process involved hydrodistillation of the leaves. The chemical compositions of the EOs were analyzed using gas [...] Read more.
Volatile oils or essential oils (EOs) were extracted from three V. sebifera samples (labeled as A, B, and C) in September 2018 and February 2019; the extraction process involved hydrodistillation of the leaves. The chemical compositions of the EOs were analyzed using gas chromatography-mass spectrometry (GC/MS). The volatile components were identified by comparing their retention indices and mass spectra with standard substances documented in the literature (ADAMS). The antioxidant activity of the EOs was evaluated using 2, 2-diphenyl-1-picrylhydrazyl (DPPH), while their toxicity was assessed using Artemia salina Leach. Molecular docking was utilized to examine the interaction between the major constituents of V. sebifera EO and acetylcholinesterase (AChE), a molecular target linked to toxicity in A. salina models. The EO obtained from specimen A, collected in September 2018, was characterized by being primarily composed of (E,E)-α-farnesene (47.57%), (E)-caryophyllene (12.26%), and α-pinene (6.93%). Conversely, the EO from specimen A, collected in February 2019, was predominantly composed of (E,E)-α-farnesene (42.82%), (E)-caryophyllene (16.02%), and bicyclogermacrene (8.85%), the EO from specimen B, collected in September 2018, primarily contained (E,E)-α-farnesene (47.65%), (E)-caryophyllene (19.67%), and α-pinene (11.95%), and the EO from the leaves collected in February 2019 was characterized by (E,E)-α-farnesene (23.57%), (E)-caryophyllene (19.34%), and germacrene D (7.33%). The EO from the leaves collected in September 2018 contained (E,E)-α-farnesene (26.65%), (E)-caryophyllene (15.7%), and germacrene D (7.72%), while the EO from the leaves collected in February 2019 was primarily characterized by (E,E)-α-farnesene (37.43%), (E)-caryophyllene (21.4%), and α-pinene (16.91%). Among these EOs, sample B collected in February 2019 demonstrated the highest potential for inhibiting free radicals, with an inhibition rate of 34.74%. Conversely, the EOs from specimen A exhibited the highest toxic potentials, with an lethal concentration 50 (LC50) value of 57.62 ± 1.53 µg/mL, while specimen B had an LC50 value of 74.72 ± 2.86 µg/mL. Molecular docking results suggested that hydrophobic interactions significantly contributed to the binding of the major compounds in the EO from sample B to the binding pocket of AChE. Full article
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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18 pages, 4838 KiB  
Article
Chemical Composition of Piper nigrum L. Cultivar Guajarina Essential Oils and Their Biological Activity
by Bruna de Souza Feitosa, Oberdan Oliveira Ferreira, Celeste de Jesus Pereira Franco, Himani Karakoti, Ravendra Kumar, Marcia Moraes Cascaes, Rahul D. Jawarkar, Suraj N. Mali, Jorddy Neves Cruz, Ilmarina Campos de Menezes, Mozaniel Santana de Oliveira and Eloisa Helena de Aguiar Andrade
Molecules 2024, 29(5), 947; https://doi.org/10.3390/molecules29050947 - 21 Feb 2024
Cited by 1 | Viewed by 1984
Abstract
The essential oils and aroma derived from the leaves (L), stems (St), and spikes (s) of Piper nigrum L. cv. Guajarina were extracted; the essential oils were extracted using hydrodistillation (HD), and steam distillation (SD), and the aroma was obtained by simultaneous distillation [...] Read more.
The essential oils and aroma derived from the leaves (L), stems (St), and spikes (s) of Piper nigrum L. cv. Guajarina were extracted; the essential oils were extracted using hydrodistillation (HD), and steam distillation (SD), and the aroma was obtained by simultaneous distillation and extraction (SDE). Chemical constituents were identified and quantified using GC/MS and GC-FID. Preliminary biological activity was assessed by determining the toxicity against Artemia salina Leach larvae, calculating mortality rates, and determining lethal concentration values (LC50). The predominant compounds in essential oil samples included α-pinene (0–5.6%), β-pinene (0–22.7%), limonene (0–19.3%), 35 linalool (0–5.3%), δ-elemene (0–10.1%), β-caryophyllene (0.5–21.9%), γ-elemene (7.5–33.9%), and curzerene (6.9–31.7%). Multivariate analysis, employing principal component analysis (PCA) and hierarchical cluster analysis (HCA), revealed three groups among the identified classes and two groups among individual compounds. The highest antioxidant activity was found for essential oils derived from the leaves (167.9 41 mg TE mL−1). Larvicidal potential against A. salina was observed in essential oils obtained from the leaves (LC50 6.40 μg mL−1) and spikes (LC50 6.44 μg mL−1). The in silico studies demonstrated that the main compounds can interact with acetylcholinesterase, thus showing the potential molecular interaction responsible for the toxicity of the essential oil in A. salina. Full article
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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14 pages, 5477 KiB  
Article
RNA-Seq-Based Transcriptomics and GC–MS Quantitative Analysis Reveal Antifungal Mechanisms of Essential Oil of Clausena lansium (Lour.) Skeels Seeds against Candida albicans
by Yinzheng Ma, Jinlei Sui, Yan Wang, Wanying Sun, Guohui Yi, Jinyan Wu, Shi Qiu, Lili Wang, Aihua Zhang and Xiaowen He
Molecules 2023, 28(24), 8052; https://doi.org/10.3390/molecules28248052 - 12 Dec 2023
Cited by 1 | Viewed by 1315
Abstract
Infections caused by Candida albicans (C. albicans) and increasing resistance to commonly used drugs lead to a variety of mucosal diseases and systemic infectious diseases. We previously confirmed that the essential oil of Clausena lansium (Lour.) Skeels seeds (CSEO) had antifungal [...] Read more.
Infections caused by Candida albicans (C. albicans) and increasing resistance to commonly used drugs lead to a variety of mucosal diseases and systemic infectious diseases. We previously confirmed that the essential oil of Clausena lansium (Lour.) Skeels seeds (CSEO) had antifungal activity against C. albicans, but the detailed mechanism between the chemical components and antifungal activity is unclear. In this study, a quantitative analysis of five volatile components of CSEO, including sabinene, α-phellandrene, β-phellandrene, 4-terpineol, and β-caryophyllene, was carried out using the gas chromatography–mass spectrometry (GC–MS) method. Both the broth dilution and kinetic growth methods proved that the antifungal activity of CSEO against fluconazole-resistant C. albicans was better than that of its main components (sabinene and 4-terpineol). To further investigate the inhibitory mechanism, the transcriptional responses of C. albicans to CSEO, sabinene, and 4-terpineol treatment were determined based on RNA-seq. The Venn diagram and clustering analysis pattern of differential expression genes showed the mechanism of CSEO and 4-terpineol’s anti-C. albicans activity might be similar from the perspective of the genes. Functional enrichment analysis suggested that CSEO regulated adherence-, hyphae-, and biofilm-formation-related genes, which may be CSEO’s active mechanism of inhibiting the growth of fluconazole-resistant C. albicans. Overall, we preliminarily revealed the molecular mechanism between the chemical components and the antifungal activity of CSEO against C. albicans. This study provides new insights to overcome the azole resistance of C. albicans and promote the development and application of C. lansium (Lour.) Skeels seeds. Full article
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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14 pages, 1174 KiB  
Article
Volatile Composition, Antimicrobial Activity, and In Vitro Innate Immunomodulatory Activity of Echinacea purpurea (L.) Moench Essential Oils
by Noura S. Dosoky, Liliya N. Kirpotina, Igor A. Schepetkin, Andrei I. Khlebnikov, Brent L. Lisonbee, Jeffrey L. Black, Hillary Woolf, Trever L. Thurgood, Brittany L. Graf, Prabodh Satyal and Mark T. Quinn
Molecules 2023, 28(21), 7330; https://doi.org/10.3390/molecules28217330 - 29 Oct 2023
Cited by 8 | Viewed by 2605
Abstract
Echinacea purpurea (L.) Moench is a medicinal plant commonly used for the treatment of upper respiratory tract infections, the common cold, sore throat, migraine, colic, stomach cramps, and toothaches and the promotion of wound healing. Based on the known pharmacological properties of essential oils [...] Read more.
Echinacea purpurea (L.) Moench is a medicinal plant commonly used for the treatment of upper respiratory tract infections, the common cold, sore throat, migraine, colic, stomach cramps, and toothaches and the promotion of wound healing. Based on the known pharmacological properties of essential oils (EOs), we hypothesized that E. purpurea EOs may contribute to these medicinal properties. In this work, EOs from the flowers of E. purpurea were steam-distilled and analyzed by gas chromatography–mass spectrometry (GC–MS), GC with flame-ionization detection (GC–FID), and chiral GC–MS. The EOs were also evaluated for in vitro antimicrobial and innate immunomodulatory activity. About 87 compounds were identified in five samples of the steam-distilled E. purpurea EO. The major components of the E. purpurea EO were germacrene D (42.0 ± 4.61%), α-phellandrene (10.09 ± 1.59%), β-caryophyllene (5.75 ± 1.72%), γ-curcumene (5.03 ± 1.96%), α-pinene (4.44 ± 1.78%), δ-cadinene (3.31 ± 0.61%), and β-pinene (2.43 ± 0.98%). Eleven chiral compounds were identified in the E. purpurea EO, including α-pinene, sabinene, β-pinene, α-phellandrene, limonene, β-phellandrene, α-copaene, β-elemene, β-caryophyllene, germacrene D, and δ-cadinene. Analysis of E. purpurea EO antimicrobial activity showed that they inhibited the growth of several bacterial species, although the EO did not seem to be effective for Staphylococcus aureus. The E. purpurea EO and its major components induced intracellular calcium mobilization in human neutrophils. Additionally, pretreatment of human neutrophils with the E. purpurea EO or (+)-δ-cadinene suppressed agonist-induced neutrophil calcium mobilization and chemotaxis. Moreover, pharmacophore mapping studies predicted two potential MAPK targets for (+)-δ-cadinene. Our results are consistent with previous reports on the innate immunomodulatory activities of β-caryophyllene, α-phellandrene, and germacrene D. Thus, this study identified δ-cadinene as a novel neutrophil agonist and suggests that δ-cadinene may contribute to the reported immunomodulatory activity of E. purpurea. Full article
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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Review

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23 pages, 1882 KiB  
Review
Exploring the Potential of Myrcia Genus Essential Oils: A Review of Biological Activities and Recent Advances
by Eliza de Jesus Barros dos Santos, Fernanda Wariss Figueiredo Bezerra, Luiz Renan Ramos da Silva, Marcilene Paiva da Silva, Oberdan Oliveira Ferreira, Luiza Helena da Silva Martins, Antônio Maia de Jesus Chaves-Neto, Anderson de Santana Botelho, Ravendra Kumar, Pooja Bargali, Karyme do Socorro de Souza Vilhena, Eloisa Helena de Aguiar Andrade and Mozaniel Santana de Oliveira
Molecules 2024, 29(12), 2720; https://doi.org/10.3390/molecules29122720 - 7 Jun 2024
Viewed by 1241
Abstract
The present study provides a comprehensive analysis of the chemical composition of essential oils from species of the Myrcia genus and their applications. The compiled results highlight the chemical diversity and biological activities of these oils, emphasizing their potential importance for various therapeutic [...] Read more.
The present study provides a comprehensive analysis of the chemical composition of essential oils from species of the Myrcia genus and their applications. The compiled results highlight the chemical diversity and biological activities of these oils, emphasizing their potential importance for various therapeutic and industrial applications. The findings reveal that Myrcia essential oils present a variety of bioactive compounds, such as monoterpenes and sesquiterpenes, which demonstrate antimicrobial activities against a range of microorganisms, including Gram-positive and Gram-negative bacteria, as well as yeasts. Furthermore, this study highlights the phytotoxic activity of these oils, indicating their potential for weed control. The results also point to the insecticidal potential of Myrcia essential oils against a range of pests, showing their viability as an alternative to synthetic pesticides. Additionally, species of the genus Myrcia have demonstrated promising hypoglycemic effects, suggesting their potential in diabetes treatment. This comprehensive synthesis represents a significant advancement in understanding Myrcia essential oils, highlighting their chemical diversity and wide range of biological activities. However, the need for further research is emphasized to fully explore the therapeutic and industrial potential of these oils, including the identification of new compounds, understanding of their mechanisms of action, and evaluation of safety and efficacy in different contexts. Full article
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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