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Essential Oils: Extraction, Separation and Biological Activities

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

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 17857

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Institute for Medicinal Plants Research “Dr Josif Pancic”, 11000 Belgrade, Serbia
Interests: essential oils; cultivation; statistics
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Special Issue Information

Dear Colleagues,

Essential oils are products obtained from plants or fruits, like by steam distillation, mechanical processes of citrus fruit epicarp , or dry distillation after separation of the aqueous phase by physical processes. They are a complex mixture of volatile secondary metabolites essentially composed of terpenoids and phenolic compounds usually with oxygenated structures such as alcohols, ketones, aldehydes, and esters. Essential oils and isolated essential oil compounds are known to pocess various bioacitve properties, such as antibacterial, antiviral, anti-inflammatory, anti-immunomodulatory and antioxidant effects.

This Special Issue deals with the potential bioactivities of essential oils and essential oil compounds together with their extraction and separation methods. Original research papers, communications, review articles, and opinions are all welcomed.

Dr. Dejan S. Pljevljakušić
Dr. Laura De Martino
Guest Editors

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Keywords

  • essential oils
  • extraction
  • separation
  • bioactive compounds
  • bioactivities

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Published Papers (8 papers)

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Research

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25 pages, 3884 KiB  
Article
Potential of Thuja occidentalis L. Essential Oil and Water Extracts against Field Crop Pests
by Janina Gospodarek, Agnieszka Krajewska, Iwona B. Paśmionka, Joanna Bruździńska and Gedyon Tamiru
Molecules 2024, 29(7), 1457; https://doi.org/10.3390/molecules29071457 - 24 Mar 2024
Viewed by 1508
Abstract
Thuja occidentalis L. essential oil (EOTO) and its compounds, such as terpinyl acetate, bornyl acetate, and β-thujone, are claimed to be highly effective against some storage pests, sanitary insects, or pests of fruit trees, while data about its use in protecting field crops [...] Read more.
Thuja occidentalis L. essential oil (EOTO) and its compounds, such as terpinyl acetate, bornyl acetate, and β-thujone, are claimed to be highly effective against some storage pests, sanitary insects, or pests of fruit trees, while data about its use in protecting field crops are very scarce. There is also a lack of information in the literature about the insecticidal value of water extracts from T. occidentalis (WETOs). Both essential oils (EOs) and water extracts (WEs) from various plants have advantages and disadvantages in terms of their use as insecticides. EOs are generally more effective, but their preparation is more complicated and quite expensive. In turn, WEs are simple to prepare and cheap, but they often have limited effectiveness. Moreover, significant differences in responses exist depending on the species of the donor plant, the method of preparing the extract, its concentration, the species of the pest being controlled, the developmental stage, and even the gender of the pest. The goals of the research were to assess the effect of EOTO and WETOs prepared from dry and fresh matter on the mortality, feeding, and body mass changes of important crop pests, i.e., the black bean aphid, pea leaf weevil, and Colorado potato beetle (CPB), respectively, as well as on the mortality and voracity of non-target organism Asian lady beetle young larvae. EOTO showed significant aphicidal activity with LC50 = 0.8267% and 0.2453% after 42 h of the experiment for nymphs and wingless females of black bean aphid, respectively. Adults of CPB were more resistant to EOTO than aphids, with LC50 values for females equal to 1.5327% and 1.3113% after 48 h and after 72 h of the experiment. There was no significant effect of EOTO on CPB foraging. Calculated LC50 values for pea leaf weevil adults were lower than those for CPB (0.9638% and 0.8573% for males after 12 h and 24 h, respectively). In the case of this pest, a clear reduction in foraging was obtained, with higher concentrations of EOTO resulting in more pronounced reductions in foraging behavior. Concentrations of EOTO above 0.5%, which showed efficacy against the aphid, were lethal to 3-day-old larvae of the Asian lady beetle. WETOs, in turn, showed significant potential in inhibiting adult pea leaf weevil feeding, with very low or no effectiveness in reducing A. fabae and CPB, respectively. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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14 pages, 2036 KiB  
Article
Extraction, Chemical Composition and Insecticidal Activities of Lantana camara Linn. Leaf Essential Oils against Tribolium castaneum, Lasioderma serricorne and Callosobruchus chinensis
by Kolapparamban Aisha, Naduvilthara U. Visakh, Berin Pathrose, Nicola Mori, Rowida S. Baeshen and Rady Shawer
Molecules 2024, 29(2), 344; https://doi.org/10.3390/molecules29020344 - 10 Jan 2024
Cited by 10 | Viewed by 3459
Abstract
Storage pests and the food spoilage they cause are problems of great concern. Using essential oil obtained from different plants as an insecticide against these storage pests can be considered an environmentally friendly pest management option. Lantana camara Linn. (family Verbenaceae) is a [...] Read more.
Storage pests and the food spoilage they cause are problems of great concern. Using essential oil obtained from different plants as an insecticide against these storage pests can be considered an environmentally friendly pest management option. Lantana camara Linn. (family Verbenaceae) is a flowering species, and is also a noxious weed that can proliferate well in nearly all geographical habitats. A biopesticide derived from the essential oil extracted from this plant can offer an effective solution for controlling storage pests. The goal of this study is to extract and analyse the chemical composition of essential oil obtained from L. camara leaves, and assess its effectiveness as a bioactive substance against three storage pests: Tribolium castaneum, Lasioderma serricorne, and Callosobruchus chinensis. The yield of essential oil extracted from L. camara leaves was about 0.24 ± 0.014%. By employing the GC-MS technique, the major phytochemicals contained in L. camara leaf essential oil were identified as caryophyllene (69.96%), isoledene (12%), and ɑ-copaene (4.11%). The essential oil exhibited excellent fumigant toxicity (LC50 of 16.70 mg/L air for T. castaneum, 4.141 mg/L air for L. serricorne and 6.245 mg/L air for C. chinensis at 24 h), contact toxicity (LC50 of 8.93 mg/cm2 for T. castaneum, 4.82 mg/cm2 for L. serricorne and 6.24 mg/cm2 for C. chinensis after 24 h) along with effective repellent activity towards the test insects. In addition, the oil showed no significant phytotoxicity on the germination of paddy seeds. This presents the potential to utilize a weed in developing a biopesticide for effectively managing stored product insects because of its strong bioactivity. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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19 pages, 2713 KiB  
Article
Chemical Composition, Preliminary Toxicity, and Antioxidant Potential of Piper marginatum Sensu Lato Essential Oils and Molecular Modeling Study
by 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 and Eloisa Helena de Aguiar Andrade
Molecules 2023, 28(15), 5814; https://doi.org/10.3390/molecules28155814 - 1 Aug 2023
Cited by 4 | Viewed by 1572
Abstract
The essential oils (OEs) of the leaves, stems, and spikes of P. marginatum 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 [...] Read more.
The essential oils (OEs) of the leaves, stems, and spikes of P. marginatum 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 Artemia salina Leach larvae and calculating the mortality rate and lethal concentration (LC50). 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 P. marginatum are characterized by the high contents of (E)-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 P. marginatum extracted by SD in November (84.9 ± 4.0 mg TE·mL−1) and the OEs of the leaves extracted by HD in March (126.8 ± 12.3 mg TE·mL−1). 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−1. 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. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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13 pages, 2549 KiB  
Article
Quality Control and Authentication of Black Betel Leaf Extract (Piper acre Blume) from East Kalimantan as an Antimicrobial Agent Using a Combination of High-Performance Liquid Chromatography and Chemometric Fourier Transform Infrared
by Vina Maulidya, Aliya Nur Hasanah, Laode Rijai and Muchtaridi Muchtaridi
Molecules 2023, 28(15), 5666; https://doi.org/10.3390/molecules28155666 - 26 Jul 2023
Cited by 2 | Viewed by 1527
Abstract
Black betel leaf from East Kalimantan contains various secondary metabolites such as alkaloid saponins, flavonoids, and tannins. A compound, piperenamide A, which has antimicrobial activity, is also found in black betel leaf. This study aims to identify and authenticate the compound piperenamide A [...] Read more.
Black betel leaf from East Kalimantan contains various secondary metabolites such as alkaloid saponins, flavonoids, and tannins. A compound, piperenamide A, which has antimicrobial activity, is also found in black betel leaf. This study aims to identify and authenticate the compound piperenamide A found in black betel leaf extract in other types of betel plant using HPLC and FTIR-chemometrics. The extraction method used was maceration with 70% ethanol solvent. Determination of piperenamide A content in black betel leaf extract was via HPLC column C18, with a maximum wavelength of 259 nm and a mobile phase of water:acetonitrile at a flow rate of 1 mL/minute. From the results, piperenamide A was only found in black betel (Piper acre) and not in Piper betel and Piper crocatum. Piperenamide A levels obtained were 4.03, 6.84, 5.35, 13.85, and 2.15%, respectively, in the samples studied. The combination of FTIR spectra with chemometric methods such as PCA and PLS-DA was used to distinguish the three types of betel. Discriminant analysis can classify black betel (Piper acre), Piper betel, and Piper crocatum according to its type. These methods can be used for identification and authentication of black betel. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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18 pages, 2680 KiB  
Article
Contact and Gastric Effect of Peppermint Oil on Selected Pests and Aphid Predator Harmonia axyridis Pallas
by Janina Gospodarek, Agnieszka Krajewska and Iwona B. Paśmionka
Molecules 2023, 28(12), 4647; https://doi.org/10.3390/molecules28124647 - 8 Jun 2023
Cited by 2 | Viewed by 2435
Abstract
Peppermint essential oil (EO) has been extensively tested to date in reducing stored-product insects and insects of public health concern with very promising results, while only a few studies target important crop pests. There is also very little information on the effects of [...] Read more.
Peppermint essential oil (EO) has been extensively tested to date in reducing stored-product insects and insects of public health concern with very promising results, while only a few studies target important crop pests. There is also very little information on the effects of peppermint EO on non-target organisms, especially concerning contact and gastric effects at the same time. The goal of the investigation was the determination of the effect of peppermint EO on the mortality of Aphis fabae Scop.; the feeding intensity and weight gain of Leptinotarsa decemlineata Say. larvae; and the mortality and voracity of non-target organism Harmonia axyridis Pallas larvae. Our research indicates promising use for the M. piperita EO against aphids and young larvae (second instars) of the Colorado potato beetle. M. piperita EO showed good insecticidal efficacy against A. fabae with LC50 = 0.5442% for nymphs and 0.3768% for wingless females after 6 h. Over time, the LC50 value decreased. For the second instar larvae of L. decemlineata, the LC50 values were 0.6278%, 0.3449%, and 0.2020% after 1, 2, and 3 days of the experiment, respectively. On the other hand, older larvae (fourth instar) were characterized by significant resistance to the tested oil concentrations with LC50 value = 0.7289% after 96 h. M. piperita oil (contact and gastric effects) at a concentration of 0.5% was found to be toxic to young larvae (2 and 5 days old) of H. axyridis, while EO at a concentration of 1% was toxic to 8-day-old larvae. Thus, for the sake of ladybug safety, it would be advisable to use EO from M. piperita against aphids at concentrations lower than 0.5%. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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16 pages, 3427 KiB  
Article
Chemometrics of the Composition and Antioxidant Capacity of Hyptis crenata Essential Oils from Brazil
by Maria Nancy N. de Lima, Jamile Silva da Costa, Bruna A. Guimarães, Jofre Jacob S. Freitas, William N. Setzer, Joyce Kelly R. da Silva, José Guilherme S. Maia and Pablo Luis B. Figueiredo
Molecules 2023, 28(8), 3371; https://doi.org/10.3390/molecules28083371 - 11 Apr 2023
Cited by 3 | Viewed by 2097
Abstract
Hyptis crenata (Pohl) ex Benth is used in traditional medicine as an analgesic to treat general pain. Six Hyptis crenata samples (Hc-1 to Hc-6) were collected in Pará state, Brazil. The leaf essential oils were obtained by hydrodistillation, and GC-MS and GC-FID were [...] Read more.
Hyptis crenata (Pohl) ex Benth is used in traditional medicine as an analgesic to treat general pain. Six Hyptis crenata samples (Hc-1 to Hc-6) were collected in Pará state, Brazil. The leaf essential oils were obtained by hydrodistillation, and GC-MS and GC-FID were used to analyze their chemical compositions. The antioxidant capacity was measured in vitro using DPPH and carotene/linoleic acid assays. Chemometrics analysis (PCA, HCA, and clustered heat map) were used to identify the sample relationships between those collected in this study and those from the literature (Hc-7 to Hc-16) samples. According to the main chemical constituents identified in the samples described in this work and the literature, the sixteen samples were classified into ten groups. Group I was characterized by 1,8-cineole (31.0%), α-pinene (13.6%), (E)-caryophyllene (7.8%), and β-pinene (7.6%); and Group IV was characterized by 1,8-cineole (17.4–23.5%), α-pinene (15.7–23.5%), β-pinene (10.5–13.4%), and limonene (8.5–9.7%). Both groups are described for the first time. The total antioxidant capacity was expressed in Trolox Equivalent Antioxidant Capacity values (TEAC): TEAC of Hc-5 (551.9 mg.TE/g) and Hc-6 (475.1 mg.TE/g). In the β-carotene/linoleic acid assay, the highest inhibition was from Hc-2 (40.0%), Hc-6 (39.0%), and Hc-3 (29.4%). Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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17 pages, 4601 KiB  
Article
Volatile Components, Antioxidant and Phytotoxic Activity of the Essential Oil of Piper acutifolium Ruiz & Pav. from Peru
by Carmela Fiorella Cuadros-Siguas, Oscar Herrera-Calderon, Gaber El-Saber Batiha, Najlaa Hamed Almohmadi, Nada H. Aljarba, José Alfonso Apesteguia-Infantes, Eddie Loyola-Gonzales, Freddy Emilio Tataje-Napuri, José Francisco Kong-Chirinos, José Santiago Almeida-Galindo, Haydee Chávez and Josefa Bertha Pari-Olarte
Molecules 2023, 28(8), 3348; https://doi.org/10.3390/molecules28083348 - 10 Apr 2023
Cited by 3 | Viewed by 2597
Abstract
Piper acutifolium Ruiz & Pav is known as “matico” and belongs to the Piperaceae family, and in Peru it is traditionally used as an infusion or decoction to ameliorate wound healings or ulcers. In this study, the aim was to investigate the volatile [...] Read more.
Piper acutifolium Ruiz & Pav is known as “matico” and belongs to the Piperaceae family, and in Peru it is traditionally used as an infusion or decoction to ameliorate wound healings or ulcers. In this study, the aim was to investigate the volatile components, the antioxidant profile, and the phytotoxic activity of the essential oil (EO) of P. acutifolium from Peru. To identify the phytoconstituents, the EO was injected into a Gas Chromatography-Mass Spectrometry (GC-MS) to obtain the chemical profile of the volatile components, followed by the antioxidant activity carried out by the reaction with three organic radicals (2,2-diphenyl-1-picrylhydrazyl (DPPH); 2,2′-azinobis-(3-ethylbenzothiazoline)-6- sulfonic acid (ABTS); ferric reducing/antioxidant power (FRAP)). Finally, the phytotoxic capabilities of the EO were tested on two model plants, Lactuca sativa seeds and Allium cepa bulbs. As a result, the analysis identified α-phellandrene as its main volatile chemical at 38.18%, followed by β-myrcene (29.48%) and β-phellandrene (21.88%). Regarding the antioxidant profile, the half inhibitory concentration (IC50) in DPPH was 160.12 ± 0.30 µg/mL, for ABTS it was 138.10 ± 0.06 µg/mL and finally in FRAP it was 450.10 ± 0.05 µg/mL. The phytotoxic activity demonstrated that the EO had high activity at 5% and 10% against L. sativa seed germination, the inhibition of root length, and hypocotyl length. Additionally, in A. cepa bulbs, the inhibition root length was obtained at 10%, both comparable to glyphosate, which was used as a positive control. The molecular docking on 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) revealed that α-phellandrene had −5.8 kcal/mol, being near to glyphosate at −6.3 kcal/mol. The conclusion shows that the EO of P. acutifolium presented antioxidant and phytotoxic activity and might be useful as a bioherbicide in the future. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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Review

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42 pages, 24839 KiB  
Review
Phytochemistry and Pharmacology of Sesquiterpenoids from Atractylodes DC. Genus Rhizomes
by Zhengyi Qu, Hongqun Liu, Zhenghai Zhang, Peihe Zheng, Shuting Zhao and Wei Hou
Molecules 2024, 29(6), 1379; https://doi.org/10.3390/molecules29061379 - 20 Mar 2024
Cited by 2 | Viewed by 1884
Abstract
The rhizomes of the genus Atractylodes DC. consist of various bioactive components, including sesquiterpenes, which have attracted a great deal of research interest in recent years. In the present study, we reviewed the previously published literatures prior to November 2023 on the chemical [...] Read more.
The rhizomes of the genus Atractylodes DC. consist of various bioactive components, including sesquiterpenes, which have attracted a great deal of research interest in recent years. In the present study, we reviewed the previously published literatures prior to November 2023 on the chemical structures, biosynthetic pathways, and pharmacological activities of the sesquiterpenoids from this genus via online databases such as Web of Science, Google Scholar, and ScienceDirect. Phytochemical studies have led to the identification of more than 160 sesquiterpenes, notably eudesmane-type sesquiterpenes. Many pharmacological activities have been demonstrated, particularly anticancer, anti-inflammatory, and antibacterial and antiviral activities. This review presents updated, comprehensive and categorized information on the phytochemistry and pharmacology of sesquiterpenes in Atractylodes DC., with the aim of offering guidance for the future exploitation and utilization of active ingredients in this genus. Full article
(This article belongs to the Special Issue Essential Oils: Extraction, Separation and Biological Activities)
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