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Advances in Essential Oils from Medicinal Plants

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A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (20 January 2025) | Viewed by 18639

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Prof. Dr. Milen I. Georgiev

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Metabolomics Laboratory, Institute of Microbiology, Bulgarian Academy of Sciences, 139 Ruski Blvd., 4000 Plovdiv, Bulgaria
Interests: plant secondary metabolism; natural products chemistry; leads finding; metabolomics; plant biotechnology
Special Issues, Collections and Topics in MDPI journals

Dr. Stanislava Ivanova

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Guest Editor

1. Department of Pharmacognosy and Pharmaceutical Chemistry, Faculty of Pharmacy, Medical University of Plovdiv, 4002 Plovdiv, Bulgaria
2. Research Institute, Medical University of Plovdiv, 4002 Plovdiv, Bulgaria
Interests: nutrition; phytochemistry; phytotherapy; pharmaceutical analysis
Special Issues, Collections and Topics in MDPI journals

Dr. Cédric Delattre

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Co-Guest Editor

1. Institut Universitaire de France (IUF), 1 rue Descartes, 75005 Paris, France
2. Clermont Auvergne INP, CNRS, Institut Pascal, Université Clermont Auvergne, 63000 Clermont-Ferrand, France
Interests: biomaterials; polymers; polysaccharides; nanomaterials
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Special Issue Information

Dear Colleagues,

Essential oils are sources of valuable compounds of a large variety of traditional applications. The huge diversity of terpenes, exceeding more than 30,000 compounds, attracts attention to essential oils, in the component composition of which they are principal constituents. This constituent variability also determines a wide range of pharmacological activities, including antiseptic, revulsive, cooling, local anesthetic, anti-inflammatory, expectorant, appetite-stimulating, cholagogue and choleretic, diuretic, and sedative, in dermatological and inhalation preparations, in aromatherapy, as flavoring agents in pharmaceutical manufacture, in perfumery and cosmetics, in the manufacture of soaps and detergents, and in the food (spices), alcohol, and tobacco industries. However, essential oils could offer many novel possible applications in different fields such as medicine, cosmetics, or agriculture. Of particular interest for this Special Issue are essential oils from endemic plants.

Submissions are invited on related topics that include, but are not limited to:

The chemical analysis of essential oils obtainedfrom endemic plants;
The histochemical analysis of essential oil-bearing plants;
The biological activity of essential oils;
Essential oils as a "green" alternative of pesticides.

Prof. Dr. Milen I. Georgiev
Dr. Stanislava Ivanova
Dr. Cédric Delattre
Guest Editors

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Keywords

essential oils
gas chromatography
pharmacological activity
endemic plants

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Published Papers (10 papers)

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15 pages, 7812 KiB

Open AccessArticle

Chemical Characterization and Antibiotic-Enhancing Activity of the Essential Oils of Propolis of Melipona quadrifasciata quadrifasciata

by Emílio Sousa Albuquerque, Cicera Laura Roque Paulo, João Arthur de Oliveira Borges, Sheila Alves Gonçalves, Gabriel Gonçalves Alencar, Judith Ferreira do Carmo, Angelica Isabely de Morais Almeida, Maura Lins dos Santos, José Weverton Almeida-Bezerra, Luiz Everson da Silva, Cícera Datiane de Morais Oliveira-Tintino and Henrique Douglas Melo Coutinho

Plants 2025, 14(4), 587; https://doi.org/10.3390/plants14040587 - 14 Feb 2025

Viewed by 717

Abstract

This study investigated the chemical composition and potential antibacterial activity of the essential oils from the propolis of Melipona quadrifasciata quadrifasciata (MQP) in samples collected from the cities of Paranaguá and Guaratuba, Paraná, Brazil, during summer and winter. The chemical composition of the oils was analyzed by GC-MS, and their minimum inhibitory concentration (MIC) was determined against standard ATCC strains and some clinical isolates (Escherichia coli 06 and Staphylococcus aureus 10). The essential oils’ MICs were determined using microdilution in 96-well plates and showed no significant antibacterial activity (MIC ≥ 1024 μg/mL) when used alone. However, the essential oils enhanced the action of norfloxacin, gentamicin, and ampicillin, especially against S. aureus 10. The chemical analysis identified 68 compounds, with β-bisabolene and β-caryophyllene as the predominant constituents. Subsequently, the antibiotic-enhancing activity against the clinical isolates was evaluated. The composition of the MQP oils varied according to seasonality and location, influenced by the microclimates of the cities. The results highlight the importance of MQP oils in enhancing antibiotic activity, particularly against Gram-positive bacteria, despite the lack of significant standalone antibacterial activity. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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15 pages, 2967 KiB

Open AccessArticle

Phytochemical Composition and Biological Activity of the Essential Oil from Ericameria nauseosa Collected in Southwestern Montana, United States

by Igor A. Schepetkin, Gulmira Özek, Temel Özek, Liliya N. Kirpotina, Andrei I. Khlebnikov, Kevser Ayçiçek, Matthew Lavin and Mark T. Quinn

Plants 2024, 13(15), 2063; https://doi.org/10.3390/plants13152063 - 26 Jul 2024

Viewed by 982

Abstract

Ericameria nauseosa (Pall. ex Pursh) G.L. Nesom & G.I. Baird) is used in traditional medicine to treat various diseases; however, little is known about the immunomodulatory activity of essential oil from this plant. Thus, we isolated essential oil from the aerial parts of E. nauseosa and evaluated their chemical composition and biological activity. Compositional analysis of E. nauseosa essential oil revealed that the main (>2%) components were γ-decalactone (13.3%), cryptone (9.4%), terpinen-4-ol (9.3%), (E)-methyl cinnamate (6.0%), T-cadinol (4.7%), spathulenol (3.6%), 8Z-2,3-dihydromatricaria ester (3.1%), β-phellandrene (3.0%), p-cymen-8-ol (2.2%), 3-ethoxy-2-cycloocten-1-one (2.2%), and trans-p-menth-2-en-1-ol (2.1%). Distinctive features were the lactones (up to 15%) and polyacetylenes (up to 3.1%), including (2Z,8Z)-matricaria ester and 8Z-2,3-dihydromatricaria ester. A comparison with other reported E. nauseosa essential oil samples showed that our samples were distinct from those collected in other areas of the country; however, they did have the most similarity to one sample collected in North Central Utah. Pharmacological studies showed that E. nauseosa essential oil activated human neutrophil Ca²⁺ influx, which desensitized these cells to subsequent agonist-induced functional responses. Based on our previously reported data that nerolidol, β-pinene, spathulenol, sabinene, and γ-terpinene were active in human neutrophils, these compounds are the most likely constituents contributing to this immunomodulatory activity. However, the relatively high amount of polyacetylenes may also contribute, as these compounds have been characterized as potent immunomodulators. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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10 pages, 1693 KiB

Open AccessCommunication

Chemical Characterization and Enantioselective Analysis of Tagetes filifolia Lag. Essential Oil and Crude Extract

by Vladimir Morocho, Anghela Chamba, Paulo Pozo, Mayra Montalván and Alírica I. Suárez

Plants 2024, 13(14), 1921; https://doi.org/10.3390/plants13141921 - 12 Jul 2024

Viewed by 1082

Abstract

The essential oil (EO) of Tagetes filifolia Lag. was obtained from dried plant material through Clevenger-type steam distillation and analyzed using gas chromatography–mass spectrometry (GC/MS), a gas chromatography–flame ionization detector (GC/FID) and enantioselective gas chromatography. The results showed 50 compounds (93.33%) with a predominance of oxygenated monoterpenes. The main components were trans-anethole (55.57 ± 9.83%), tridecene <1-> (8.66 ± 0.01), methyl chavicol (5.81 ± 0.85%) and Neophytadiene (3.45 ± 0.88) Enantioselective analysis revealed linalool and <methyl-γ-> ionone as enantiomers. The identification of secondary metabolites from the ethyl acetate extract obtained by maceration was performed by GC-MS, NMR and by a literature comparison, determining the presence of mostly trans-anethole and a mixture of two triterpenes, fernenol and lupeol. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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14 pages, 2029 KiB

Open AccessArticle

Crithmum maritimum L.—Study on the Histochemical Localization of Essential Oil

by Velina Dzhoglova, Kalin Ivanov, Niko Benbassat, Yoana Georgieva-Dimova, Rayna Ardasheva, Diana Karcheva-Bahchevanska and Stanislava Ivanova

Plants 2024, 13(4), 550; https://doi.org/10.3390/plants13040550 - 17 Feb 2024

Cited by 1 | Viewed by 1890

Abstract

Crithmum maritimum L. is a perennial halophyte plant that is a medicinal herb known by people from different cultures since ancient times. However, the therapeutic potential of this halophyte has not been completely investigated, and the scientific data on it are limited. The purpose of the present study was to estimate the chemical composition of the essential oil (EO) obtained from the aerial parts of Crithmum maritimum L. growing wild in Bulgaria, as well as the histolocalization of secretory structures for the synthesis and accumulation of volatile oils. The results obtained on the EO composition of Bulgarian Crithmum maritimum L. provide an opportunity to reveal potential future applications in various fields, such as medicine, pharmacy, agriculture, food, and the cosmetic industry. Gas chromatography with mass spectrometry was performed to assess the chemical profile of the isolated EO. The phenylpropanoid dillapiole was identified as the major compound in the EO, accounting for 34.09% of the total EO. Monoterpene hydrocarbons represented 62.07% of the total oil composition. γ-Terpinene, D-limonene, and β-pinene were the most abundant monoterpene hydrocarbons in the composition of the EO. In addition, histochemical localization of EO in the stem and leaves of Crithmum maritimum L. was carried out. The secretory structures were located in the cortical region of the stem and in the mesophyll tissues of the leaves in the form of secretory ducts. The performed histochemical analysis confirmed the lipophilic nature of the secretion from the duct cells. This is the first report related to the histolocalization and chemical composition of the EO from Bulgarian Crithmum maritimum L. Furthermore, our data indicate some potential possibilities for the evaluation of the therapeutic activity of the EO obtained from this plant species and outline its future applications as a therapeutic agent. Also, the EO from the studied halophyte plant has prominent potential to be used as a biopesticide, which is an environmentally friendly option compared to standard pesticides. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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17 pages, 1553 KiB

Open AccessArticle

Unveiling the Impact of Drying Methods on Phytochemical Composition and Antioxidant Activity of Anthemis palestina

by Mahmoud A. Al-Qudah, Hala I. Al-Jaber, Faten M. Abu Orabi, Hazem S. Hasan, Amal K. Aldahoun, Abdulrahman G. Alhamzani, Abbas I. Alakhras, Tareq T. Bataineh, Abdel Monem M. Rawashdeh and Sultan T. Abu-Orabi

Plants 2023, 12(22), 3914; https://doi.org/10.3390/plants12223914 - 20 Nov 2023

Cited by 2 | Viewed by 1845

Abstract

Different drying techniques may alter the chemical composition of plant extracts and consequently affect their bioactivity potential. The current study was designed to reveal the effect of four different drying methods on the phytochemical composition and antioxidant activity of hydrodistilled essential oil (HD-EO) and methanolic (APM) extract obtained from the aerial part of Anthemis palestina from Jordan. Aerial parts of A. palestina in their fresh (FR) form and after drying in shade (ShD), sun (SD), oven at 40 °C (O40D) and 60 °C (O60D), in addition to microwave (MWD), were used to extract their essential oils by hydrodistillation and to prepare the different methanolic extracts (APM). GC/MS analysis of the different HD-EOs revealed qualitative and quantitative differences among the different samples. While FR, O40D, O60D, and MWD EO samples contained mainly sesquiterpene hydrocarbons (35.43%, 29.04%, 53.69%, and 59.38%, respectively), ShD sample was rich in oxygenated monoterpenes (33.57%), and SD-EO contained mainly oxygenated sesquiterpenes (40.36%). Principal component analysis (PCA) and Cluster analysis (CA) grouped the different drying methods based on their impact on the concentration of chemical constituents. SD-EO demonstrated high DPPH and ABTS antioxidant activity (1.31 ± 0.03) × 10⁻²; (1.66 ± 0.06) × 10⁻² μg/mL, respectively). Furthermore, A. paleistina methanolic extracts (APM) obtained after subjecting the plant to different drying methods showed interesting patterns in terms of their TPC, TFC, antioxidant activity, and phytochemical profiling. Of all extracts, SD-APM extract had the highest TPC (105.37 ± 0.19 mg GA/g DE), highest TFC (305.16 ± 3.93 mg Q/g DE) and demonstrated the highest DPPH and ABTS scavenging activities ((4.42 ± 0.02) × 10⁻²; (3.87 ± 0.02) × 10⁻² mg/mL, respectively); all were supported by correlation studies. LC-MS/MS analysis of the different extracts revealed the richness of the SD-APM extract in phenolic acids and flavonoids. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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13 pages, 866 KiB

Open AccessArticle

Eucalyptus camaldulensis Dehnh Leaf Essential Oil from Palestine Exhibits Antimicrobial and Antioxidant Activity but No Effect on Porcine Pancreatic Lipase and α-Amylase

by Nidal Jaradat, Nawaf Al-Maharik, Mohammed Hawash, Mohammad Qadi, Linda Issa, Rashad Anaya, Ayham Daraghmeh, Lobna Hijleh, Tasneem Daraghmeh, Amal Alyat and Ro’a Aboturabi

Plants 2023, 12(22), 3805; https://doi.org/10.3390/plants12223805 - 8 Nov 2023

Cited by 4 | Viewed by 2258

Abstract

Eucalyptus camaldulensis Dehnh is a tree species that is commonly used for various purposes, including forestry, agroforestry, and conservation. The present investigation was designed to determine the composition of E. camaldulensis leaves essential oil and estimate its free radicals, porcine pancreatic lipase, α-amylase inhibitory, and antimicrobial properties in vitro. The chemical constituents were analyzed using the gas chromatography-mass spectrometry (GC-MS) technique. DPPH (2,2-diphenyl-1-picrylhydrazyl), p-nitrophenyl butyrate, and 3,5-dinitro salicylic acid (DNSA) methods were employed to estimate the antioxidant, antiobesity, and antidiabetic effects of the essential oil. The microdilution assay was employed to assess the antimicrobial efficacy of the substance against a total of seven distinct microbial species. The GC-MS results revealed that E. camaldulensis essential oil contains 52 components that makeup 100% of the entire oil. The main chemical constituents in E. camaldulensis essential oil are p-cymene (38.64%), followed by aromadendrene (29.65%), and 1,8-cineol (6.45%), with monocyclic monoterpene being the most abundant phytochemical group, followed by the sesquiterpene hydrocarbon group, representing 44.27 and 31.46%, respectively. The essential oil showed a weak antioxidant effect and had no antilipase or antiamylase effects. At the same time, the oil showed a strong antimicrobial effect against methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus aureus, and Proteus vulgaris, which was even more potent than the positive controls, ciprofloxacin and ampicillin, which had MIC doses of 0.2 ± 0.01, 0.2 ± 0.01, and 6.25 ± 0.1 µg/mL, respectively. It also has a strong anti-Candida albicans effect with a MIC of 0.2 ± 0.01 µg/mL. In light of these findings, in vivo studies should be conducted to determine the efficiency of the E. camaldulensis essential oil in treating microbial infections. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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16 pages, 1690 KiB

Open AccessArticle

Composition and Biological Activity of the Essential Oils from Wild Horsemint, Yarrow, and Yampah from Subalpine Meadows in Southwestern Montana: Immunomodulatory Activity of Dillapiole

by Igor A. Schepetkin, Gulmira Özek, Temel Özek, Liliya N. Kirpotina, Robyn A. Klein, Andrei I. Khlebnikov and Mark T. Quinn

Plants 2023, 12(14), 2643; https://doi.org/10.3390/plants12142643 - 14 Jul 2023

Cited by 4 | Viewed by 2202

Abstract

Agastache urticifolia (Benth.) Kuntze (horsemint), Achillea millefolium L. (yarrow), and Perideridia gairdneri (Hook. & Arn.) Mathias (yampah) are native, culturally important plants that grow in the subalpine meadows of Montana. Analysis of the composition of essential oils extracted from these plants showed that the main components of essential oils obtained from flowers and leaves of A. urticifolia (designated as AUF/AUL) were menthone (2.7/25.7%), isomenthone (2.6/29.1%), pulegone (78.9/28.8%), and limonene (4.2/6.2%), whereas essential oils obtained from the inflorescence of A. millefolium (designated as AMI) were high in α-thujone (17.1%) and β-thujone (14.9%), 1,8-cineole (17.0%), camphor (13.0%), sabinene (7.0%), guaia-3,9-dien-11-ol (3.2%), and terpinen-4-ol (2.5%). Essential oils obtained from the inflorescence of P. gairdneri (designated as PGI) contained high amounts of dillapiole (30.3%), p-cymen-8-ol (14.1%), terpinolene (12.0%), 4-hydroxy-4-methyl-cyclohex-2-enone (6.2%), and γ-terpinene (2.4%). Evaluation of their immunomodulatory activity demonstrated that essential oils extracted from all of these plants could activate human neutrophils with varying efficacy. Analysis of individual components showed that dillapiole activated human neutrophil intracellular Ca²⁺ flux ([Ca²⁺]_i) (EC₅₀ = 19.3 ± 1.4 μM), while α-thujone, β-thujone, menthone, isomenthone, and pulegone were inactive. Since dillapiole activated neutrophils, we also evaluated if it was able to down-regulate neutrophil responses to subsequent agonist activation and found that pretreatment with dillapiole inhibited neutrophil activation by the chemoattractant fMLF (IC₅₀ = 34.3 ± 2.1 μM). Pretreatment with P. gairdneri essential oil or dillapiole also inhibited neutrophil chemotaxis induced by fMLF, suggesting these treatments could down-regulate human neutrophil responses to inflammatory chemoattractants. Thus, dillapiole may be a novel modulator of human neutrophil function. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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18 pages, 2186 KiB

Open AccessArticle

Variation in the Chemical Composition of Endemic Specimens of Hedychium coronarium J. Koenig from the Amazon and In Silico Investigation of the ADME/Tox Properties of the Major Compounds

by Jorddy Neves Cruz, Mozaniel Santana de Oliveira, Marcia Cascaes, Suraj N. Mali, Srushti Tambe, Cleydson Breno Rodrigues dos Santos, Maria das Graças Bichara Zoghbi and Eloisa Helena de Aguiar Andrade

Plants 2023, 12(14), 2626; https://doi.org/10.3390/plants12142626 - 12 Jul 2023

Cited by 2 | Viewed by 1897

Abstract

Four species of the genus Hedychium can be found in Brazil. Hedychium coronarium is a species endemic to India and Brazil. In this paper, we collected six specimens of H. coronarium for evaluation of their volatile chemical profiles. For this, the essential oils of these specimens were extracted using hydrodistillation from plant samples collected in the state of Pará, Brazil, belonging to the Amazon region in the north of the country. Substance compounds were identified with GC/MS. The most abundant constituent identified in the rhizome and root oils was 1,8-cineole (rhizome: 35.0–66.1%; root: 19.6–20.8%). Leaf blade oil was rich in β-pinene (31.6%) and (E)-caryophyllene (31.6%). The results from this paper allow for greater knowledge about the volatile chemical profile of H. coronarium specimens, in addition to disseminating knowledge about the volatile compounds present in plant species in the Amazon region. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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21 pages, 33719 KiB

Open AccessArticle

Chamaecyparis lawsoniana Leaf Essential Oil as a Potential Anticancer Agent: Experimental and Computational Studies

by Eman Fikry, Raha Orfali, Samar S. Elbaramawi, Shagufta Perveen, Azza M. El-Shafae, Maher M. El-Domiaty and Nora Tawfeek

Plants 2023, 12(13), 2475; https://doi.org/10.3390/plants12132475 - 28 Jun 2023

Cited by 4 | Viewed by 2416

Abstract

Cancer remains one of the leading causes of death worldwide, affected by several factors including oxidative stress; and although conventional synthetic medicines have been used to treat cancer, they often result in various side effects. Consequently, there is a growing need for newer, safer and more effective alternatives, such as natural plant products. Essential oils (EOs) are one such alternative, offering a wide range of bioactivities, including antibacterial, antiviral, antioxidant, and anticancer properties. Accordingly, the objective of the present study was to investigate the chemical composition, as well as the antioxidant and anticancer properties of the leaf essential oil of Chamaecyparis lawsoniana (CLLEO) belonging to the Cupressaceae family. Totally, 59 constituents were identified by gas chromatography-mass spectrometry (GC-MS) analysis. cis-Abienol, trans-ferruginol, α-cadinol, δ-muurolene and α-pinene were the major components. The in vitro cytotoxicity study against human breast (MCF-7), colon (HCT-116), lung (A-549), hepatocellular (HepG-2) carcinoma cells using MTT assay indicated a promising cytotoxic activity against all the tested cancer cells, particularly HepG-2, with significant selectivity indices. CLLEO exhibited weak antioxidant activity according to the DPPH, ABTS and FRAP assays. In silico docking of these constituents against the epidermal growth factor receptor (EGFR), the myeloid cell leukemia-1 (Mcl-1) and caspase-8 using Molecular Operating Environment (MOE) software demonstrated good binding affinities of the components with the active site of these targets. These findings suggested using CLLEO, or its individual components, as a potentially viable therapeutic option for managing cancerous conditions. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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Review

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22 pages, 1917 KiB

Open AccessReview

Genus Echinophora—Biological Activity, Chemical Composition, and Future Perspectives

by Stanislava Ivanova, Stanislav Dyankov, Rayna Ardasheva and Kalin Ivanov

Plants 2024, 13(12), 1599; https://doi.org/10.3390/plants13121599 - 8 Jun 2024

Cited by 2 | Viewed by 2000

Abstract

Species belonging to the genus Echinophora (Apiaceae) have been used by humanity since ancient times as flavoring agents, preservatives, and medicines for the treatment of a broad spectrum of conditions, including respiratory, digestive and kidney disorders, fungi infections, wounds, and gastric ulcers. Phytochemical studies on this botanical genus mainly investigate the essential oil composition and reveal the species as a rich source of volatile compounds, including monoterpenes and phenylpropanoids. Among the non-volatile secondary metabolites, flavonoids, coumarins, phenolic acids, phytosterols, and polyacetylenes have been identified. Pharmacological studies revealed Echinophora extracts and essential oils exhibit different biological properties, including antibacterial, antifungal, anticancer, insecticidal, anti-inflammatory, and hepatoprotective activities. However, compared to other genera, the biological activity and chemical diversity of this genus are not well studied. In future decades, it is highly likely that the small genus Echinophora will play an important role in drug discovery and drug development. Full article

(This article belongs to the Special Issue Advances in Essential Oils from Medicinal Plants)

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