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Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II

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

Deadline for manuscript submissions: closed (30 September 2023) | Viewed by 24605

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Prof. Dr. Marcello Iriti

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Guest Editor

Department of Biomedical, Surgical and Dental Sciences, Università degli Studi di Milano, 20133 Milan, Italy
Interests: essential oils; bioactive phytochemicals; ethnopharmacology; antimicrobial resistance; one health; food security
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Dr. Moshfekus Saleh-E-In

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Guest Editor

Division of Forest Resources, College of Forest and Environmental Sciences, Kangwon National University, Chunchon 200-701, Republic of Korea
Interests: essential oils; extraction; isolation; structure elucidation; identification and quantification of secondary metabolites by GC/MS, LC/MS/MS, HPLC and NMR techniques; biological activities; in silico prediction
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The biomolecules of medicinal and aromatic plants include essential oils and non-essential oil constituents. Essential oils are a complex natural mixture of terpenoids, phenylpropenes, allyl and isoallyl phenols, phenolic acids, related esters, as well as minor amounts of coumarins, anthraquinones, and alkaloids. Nearly 400 plant species have been identified as commercially important for essential oils. Though these plants are the major source of essential oils, they also contain a pool of bioactive compounds as well as plant products which have served humans for innumerable therapeutic applications. Biomolecules from these plants can be extracted through hydrodistillation, steam distillation, supercritical fluids, as well as ultrasound-assisted, microwave-assisted, and solvent extraction methods. The essential oils and byproducts of these plants are used in perfumery, cosmetics, aromatherapy, pharmaceutical and agrochemical industries, and as cleaning materials and scenting agents in beverages and foods. The most promising applications of essential oils are in biofuels, natural flavoring, and pesticides. Many studies have been conducted regarding the biological activities of essential oils and biomolecules, such as antioxidant, antimicrobial, antifungal, anti-inflammatory, neuroprotective, antiparasitic, cytotoxic, anticancer, insecticidal, and synergistic effects. A vigorous resurgence of interest has been observed among researchers regarding essential-oil-bearing plants due to their multidisciplinary industrial applications. Therefore, many industries have connected with research organizations and scientists in order to develop modern medicines to treat acute and chronic diseases, and for the formulation of cosmetics, pesticides, food processing and preservation agents, and biofuels.

This Special Issue focuses on the extraction, isolation, chemical analysis, and identification of essential oils and biomolecules utilizing advanced chromatographic techniques (GC-MS, LC-MS, MS/MS, QTOF); the biological activities (in vivo, vitro, and silico) of extracts and compounds from essential-oil-bearing plants; as well as the assessment of their safety and quality parameters for a wider range of industrial applications. Papers describing biotechnological approaches for the enhancement of essential oil production and quality are also encouraged.

We cordially invite authors to submit their original articles and reviews to this Special Issue with the aim of revealing the importance of naturally occurring products from essential-oil-bearing plants in order to open up new opportunities in pharmaceuticals, fuels, cosmetics, and food industries in the future.

Prof. Dr. Marcello Iriti
Dr. Moshfekus Saleh-E-In
Guest Editors

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Keywords

essential oils
biomolecules
chemical composition
extraction and isolation
GC-MS, LC-MS/MS
QTOF
biological activities
in silico
biotechnology
biofuels
pesticides
antimicrobial resistance
plant secondary metabolites
chemical ecology
phytotherapy
traditional herbal medicine

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Published Papers (7 papers)

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Research

15 pages, 3940 KiB

Open AccessArticle

Cymbopogon citratus and Citral Overcome Doxorubicin Resistance in Cancer Cells via Modulating the Drug’s Metabolism, Toxicity, and Multidrug Transporters

by Mohammed Hasan Mukhtar, Mahmoud Zaki El-Readi, Mohamed E. Elzubier, Sameer H. Fatani, Bassem Refaat, Usama Shaheen, Elshiekh Babiker Adam Khidir, Hesham Hamada Taha and Safaa Yehia Eid

Molecules 2023, 28(8), 3415; https://doi.org/10.3390/molecules28083415 - 12 Apr 2023

Cited by 4 | Viewed by 2980

Abstract

Multidrug resistance (MDR) is the major complex mechanism that causes the failure of chemotherapy, especially with drugs of natural origin such as doxorubicin (DOX). Intracellular drug accumulation and detoxification are also involved in cancer resistance by reducing the susceptibility of cancer cells to death. This research aims to identify the volatile composition of Cymbopogon citratus (lemon grass; LG) essential oil and compare the ability of LG and its major compound, citral, to modulate MDR in resistant cell lines. The composition of LG essential oil was identified using gas chromatography mass spectrometry (GC-MS). In addition, a comparison of the modulatory effects of LG and citral, performed on breast (MCF-7/ADR), hepatic (HepG-2/ADR), and ovarian (SKOV-3/ADR) MDR cell lines, were compared to their parent sensitive cells using the MTT assay, ABC transporter function assays, and RT-PCR. Oxygenated monoterpenes (53.69%), sesquiterpene hydrocarbons (19.19%), and oxygenated sesquiterpenes (13.79%) made up the yield of LG essential oil. α-citral (18.50%), β-citral (10.15%), geranyl acetate (9.65%), ylangene (5.70), δ-elemene (5.38%), and eugenol (4.77) represent the major constituents of LG oil. LG and citral (20 μg/mL) synergistically increased DOX cytotoxicity and lowered DOX dosage by >3-fold and >1.5-fold, respectively. These combinations showed synergism in the isobologram and CI < 1. DOX accumulation or reversal experiment confirmed that LG and citral modulated the efflux pump function. Both substances significantly increased DOX accumulation in resistant cells compared to untreated cells and verapamil (the positive control). RT-PCR confirmed that LG and citral targeted metabolic molecules in resistant cells and significantly downregulated PXR, CYP3A4, GST, MDR1, MRP1, and PCRP genes. Our results suggest a novel dietary and therapeutic strategy combining LG and citral with DOX to overcome multidrug resistance in cancer cells. However, these results should be confirmed by additional animal experiments before being used in human clinical trials. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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13 pages, 722 KiB

Open AccessArticle

Preliminary Study on Insecticidal Potential and Chemical Composition of Five Rutaceae Essential Oils against Thrips flavus (Thysanoptera: Thripidae)

by Tian-Hao Pei, Yi-Jin Zhao, Sheng-Yuan Wang, Xiao-Feng Li, Chen-Qi Sun, Shu-Sen Shi, Meng-Lei Xu and Yu Gao

Molecules 2023, 28(7), 2998; https://doi.org/10.3390/molecules28072998 - 28 Mar 2023

Cited by 6 | Viewed by 3401

Abstract

To meet the demand for novel pest management strategies to combat the development of insecticide resistance, plant essential oils may be a promising alternative source. This study investigated the insecticidal activity of five essential oils from the Rutaceae plant family against Thrips flavus Schrank (Thysanoptera: Thripidae) under laboratory conditions. The plant essential oils were citrus oil (Citrus reticulata Blanco), Chuan-shan pepper oil (Zanthoxylum piasezkii Maxim.), zanthoxylum oil (Zanthoxylum bungeanum Maxim.), pomelo peel oil (Citrus maxima (Burm.) Merr.) and orange leaf oil (Citrus sinensis (L.) Osbeck). Among the essential oils evaluated, orange leaf oil (LC₅₀ = 0.26 g/L), zanthoxylum oil (LC₅₀ = 0.27 g/L), and pomelo peel oil (LC₅₀ = 0.44 g/L) resulted in a higher gastric toxicity under laboratory conditions. The results of the pot experiment also showed that orange leaf oil (93.06 ± 3.67% at 540.00 g a.i.·hm⁻², 97.22 ± 1.39% at 720 g a.i.·hm⁻², 100.00% at 900.00 g a.i.·hm⁻²) zanthoxylum oil (98.73 ± 1.27% at 900 g a.i.·hm⁻²), and pomelo peel oil (100.00% at 900 g a.i.·hm⁻²) exhibited a higher control efficacy, being the most effective against T. flavus after 7 days of treatment. The essential oil components were then identified by gas chromatography–mass spectrometry (GC–MS). The insecticidal activity of orange leaf oil, pomelo peel oil, and zanthoxylum oil could be attributed to their main constituents, such as methyl jasmonate (50.92%), D-limonene (76.96%), and linalool (52.32%), respectively. In the olfactory test, adult T. flavus were attracted by zanthoxylum oil and Chuan-shan pepper oil. We speculated that linalool might be the key signaling compound that attracts T. flavus. These results showed that orange leaf oil, zanthoxylum oil, and pomelo peel oil exhibited insecticidal activities under controlled conditions. They can be implemented as effective and low-toxicity botanical insecticides and synergistic agents against T. flavus. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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14 pages, 4560 KiB

Open AccessArticle

Phytochemical Composition and Antimicrobial Activity of Essential Oil from the Leaves of Artemisia vulgaris L.

by Nameirakpam Bunindro Singh, Moirangthem Lakshmipriyari Devi, Thokchom Biona, Nanaocha Sharma, Sudripta Das, Jharna Chakravorty, Pulok Kumar Mukherjee and Yallappa Rajashekar

Molecules 2023, 28(5), 2279; https://doi.org/10.3390/molecules28052279 - 28 Feb 2023

Cited by 23 | Viewed by 4444

Abstract

Artemisia vulgaris is an enormously useful aromatic plant known for its insecticidal, antifungal, parasiticidal, and medicinal values. The main aim of this study is to investigate phytochemical contents and the potential antimicrobial activities of Artemisia vulgaris essential oil (AVEO) from the fresh leaves of A. vulgaris grown in Manipur. The AVEO isolated by hydro-distillation from A. vulgaris were analyzed by gas chromatography/mass spectrometry and solid-phase microextraction-GC/MS to describe their volatile chemical profile. There were 47 components identified in the AVEO by GC/MS, amounting to 97.66% of the total composition, while 97.35% were identified by SPME-GC/MS. The prominent compounds present in AVEO analyzed by direct injection and SPME methods are found to be eucalyptol (29.91% and 43.70%), sabinene (8.44% and 8.86%), endo-Borneol (8.24% and 4.76%), 2,7-Dimethyl-2,6-octadien-4-ol (6.76% and 4.24%), and 10-epi-γ-Eudesmol (6.50% and 3.09%). The consolidated component in the leaf volatiles comes to the terms of monoterpenes. The AVEO exhibits antimicrobial activities against fungal pathogens such as Sclerotium oryzae (ITCC 4107) and Fusarium oxysporum (MTCC 9913) and bacterial cultures such as Bacillus cereus (ATCC 13061) and Staphylococcus aureus (ATCC 25923). The percent inhibition of AVEO against the S. oryzae and F. oxysporum was found up to 50.3% and 33.13%, respectively. The MIC and MBC of the essential oil tested for B. cereus and S. aureus were found to be (0.3%, 0.63%) and (0.63%, 2.5%), respectively. Finally, the results revealed that the AVEO characterized by the hydro-distillation and SPME extraction yielded the same chemical profile and showed potent antimicrobial activities. Further research into A. vulgaris’s antibacterial properties can be performed in order to use it as a source for natural antimicrobial medications. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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14 pages, 1373 KiB

Open AccessArticle

Anti-Trypanosomatidae Activity of Essential Oils and Their Main Components from Selected Medicinal Plants

by María Bailén, Cristina Illescas, Mónica Quijada, Rafael Alberto Martínez-Díaz, Eneko Ochoa, María Teresa Gómez-Muñoz, Juliana Navarro-Rocha and Azucena González-Coloma

Molecules 2023, 28(3), 1467; https://doi.org/10.3390/molecules28031467 - 2 Feb 2023

Cited by 3 | Viewed by 2165

Abstract

Kinetoplastida is a group of flagellated protozoa characterized by the presence of a kinetoplast, a structure which is part of a large mitochondria and contains DNA. Parasites of this group include genera such as Leishmania, that cause disease in humans and animals, and Phytomonas, that are capable of infecting plants. Due to the lack of treatments, the low efficacy, or the high toxicity of the employed therapeutic agents there is a need to seek potential alternative treatments. In the present work, the antiparasitic activity on Leishmania infantum and Phytomonas davidi of 23 essential oils (EOs) from plants of the Lamiaceae and Asteraceae families, extracted by hydrodistillation (HD) at laboratory scale and steam distillation (SD) in a pilot plant, were evaluated. The chemical compositions of the EOs were determined by gas chromatography-mass spectrometry. Additionally, the cytotoxic activity on mammalian cells of the major components from the most active EOs was evaluated, and their anti-Phytomonas and anti-Leishmania effects analyzed. L. infantum was more sensitive to the EOs than P. davidi. The EOs with the best anti-kinetoplastid activity were S. montana, T. vulgaris, M. suaveolens, and L. luisieri. Steam distillation increased the linalyl acetate, β-caryophyllene, and trans-α-necrodyl acetate contents of the EOs, and decreased the amount of borneol and 1,8 cineol. The major active components of the EOs were tested, with thymol being the strongest anti-Phytomonas compound followed by carvacrol. Our study identified potential treatments against kinetoplastids. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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19 pages, 2622 KiB

Open AccessArticle

Chemical Composition, Enantiomeric Distribution, Antimicrobial and Antioxidant Activities of Origanum majorana L. Essential Oil from Nepal

by Prem Narayan Paudel, Prabodh Satyal, Rakesh Satyal, William N. Setzer and Rajendra Gyawali

Molecules 2022, 27(18), 6136; https://doi.org/10.3390/molecules27186136 - 19 Sep 2022

Cited by 25 | Viewed by 4456

Abstract

This study was conducted to examine the chemical constituents of Origanum majorana L. essential oils (EOs) that originate in Nepal, as well as their biological activities, antioxidant properties, and enantiomeric compositions. The EOs were extracted by the hydro-distillation method using a Clevenger-type apparatus and their chemical compositions were determined through gas chromatography and mass spectrometry (GC-MS). Chiral GC-MS was used to evaluate the enantiomeric compositions of EOs. The minimum inhibitory concentrations (MICs) of the essential oils were determined by the micro-broth dilution method, and the antioxidant activity was evaluated by the 2,2-diphenyl-1-picrylhydrazyl scavenging assay and ferric-reducing antioxidant power (FRAP). GC-MS analysis showed the presence of 50 and 41 compounds in the EO samples, (S₁) and (S₂), respectively, representing the Kathmandu and Bhaktapur districts. The oxygenated monoterpenoids, along with terpinen-4-ol, were predominant constituents in both EO samples. However, the EOs from two locations showed some variations in their major components. The chiral terpenoids for two EO samples of marjoram have also been reported in this study in an elaborative way for the first time in accordance with the literature review. A hierarchical cluster analysis based on the compositions of EOs with 50 compositions reported in the literature revealed at least 5 different chemotypes of marjoram oil. The antioxidant activity for the sample (S₂) was found to be relatively moderate, with an IC₅₀ value of 225.61 ± 0.05 μg/mL and an EC₅₀ value of 372.72 ± 0.84 µg/mL, as compared to the standard used. Furthermore, with an MIC value of 78.1 µg/mL, the EO from sample (S₂) demonstrated effective antifungal activity against Aspergillus niger and Candida albicans. Moreover, both samples displayed considerable antimicrobial activity. The results suggest that EOs of Origanum majorana possess some noteworthy antimicrobial properties as well as antioxidant activity, and hence can be used as a natural preservative ingredient in the food and pharmaceutical industries. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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15 pages, 3415 KiB

Open AccessArticle

Essential Oil Compositions of Pinus Species (P. contorta Subsp. contorta, P. ponderosa var. ponderosa, and P. flexilis); Enantiomeric Distribution of Terpenoids in Pinus Species

by Elizabeth Ankney, Kathy Swor, Prabodh Satyal and William N. Setzer

Molecules 2022, 27(17), 5658; https://doi.org/10.3390/molecules27175658 - 2 Sep 2022

Cited by 11 | Viewed by 2282

Abstract

Pinus species are important in traditional medicine throughout their ranges, and pine essential oils are of interest in aromatherapy and as topical treatments. In this work, the leaf (needle) essential oils of Pinus ponderosa var. ponderosa and Pinus contorta subsp. contorta from Oregon and Pinus flexilis growing in Idaho, have been obtained by hydrodistillation and analyzed by gas chromatographic techniques. The leaf essential oil of P. ponderosa was dominated by β-pinene (21.5–55.3%), methyl chavicol (8.5–41.5%), α-pinene (3.6–9.6%), δ-3-carene (3.6–6.2%), and α-terpineol (1.4–5.3%). The major components of P. contorta essential oil were β-phellandrene (23.8%), terpinen-4-ol (11.0%). The essential oil of P. flexilis was dominated by α-pinene (37.1%), β-pinene (21.9%), bornyl acetate (12.8%), and camphene (8.5%). Chiral gas chromatography revealed the enantiomeric ratios of α-pinene and limonene to be variable, but (−)-β-pinene predominated in Pinus essential oils. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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17 pages, 3456 KiB

Open AccessArticle

Synthesis of Carvacrol Derivatives as Potential New Anticancer Agent against Lung Cancer

by Anu Bansal, Md. Moshfekus Saleh-E-In, Pallab Kar, Ayan Roy and Neeta Raj Sharma

Molecules 2022, 27(14), 4597; https://doi.org/10.3390/molecules27144597 - 19 Jul 2022

Cited by 20 | Viewed by 3424

Abstract

Lung cancer remains a major public health concern among all cancer diseases due to the toxicity and side-effects of the available commercially synthesized drugs. Natural product-derived synthesized anticancer drugs are now of promising interest to fight against cancer death. Carvacrol is a major component of most essential oil-bearing plants with potential pharmacological activity, especially against various cancer cell lines. Among the other organometallic compounds, copper complexes have been reported to be effective anticancer agents against various cancer cell lines, especially lung and leukemia cancers, due to the nontoxic nature of copper in normal cells since it is an endogenic metal. In this study, we synthesized three carvacrol derivatives, i.e., carvacrol aldehyde, Schiff base, and copper–Schiff base complex, through an established synthesis protocol and characterized the synthesized product using various spectroscopic techniques. The synthesized derivatives were evaluated for in vitro cytotoxic activity against different cancer cell lines, including human lung cancer (A549) and human fibroblast (BALB-3T3). Our findings showed that the copper–Schiff base complex derived from carvacrol inhibited the proliferation and migration of the A549 cell lines in a dose-dependent manner. This activity might be due to the inhibition of cell proliferation and migration at the G₂/M cell-cycle phase, as well as apoptosis, possibly through the activation of the mitochondrial apoptotic pathway. To our knowledge, this is the first report on the activity of the copper–Schiff base complex of carvacrol against A549 cell lines. Our result highlights that a new synthesized copper complex from carvacrol could be a novel potential drug in the treatment of lung cancer. Full article

(This article belongs to the Special Issue Biomolecules from Essential Oil Bearing Plants: Biological and Industrial Applications II)

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