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Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts

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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 June 2023) | Viewed by 17350

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Prof. Dr. Mourad A. M. Aboul-Soud

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Chair of Medical and Molecular Genetics Research, Department of Clinical Laboratory Sciences, College of Applied Medical Sciences, King Saud University, P.O. Box 10219, Riyadh 11433, Saudi Arabia
Interests: chemical characterization of natural products; pharmacological activities of natural products and their mode-of-action; biochemistry & molecular biology

Special Issue Information

Dear Colleagues,

Globally, herbal medicine relying on aromatic and medicinal plants has been widely practiced by indigenous cultures to combat a myriad of pathological conditions. Medicinal plants constitute a rich source of bioactive natural products (NPs) with diverse pharmacological activities. These include antioxidant, anti-inflammatory, antimicrobial, insecticidal and anticancer properties. Bioactive NPs can be extracted from different plant parts such as leaf, stem, bark, seed and root to produce extracts or essential oils (EOs), whose biological activity is dependent upon their chemical composition and abundance. Determinants impacting the chemical composition of plant extracts and EOs have been reported to include extraction protocol, surrounding environmental factors, geographical origin and nutritional conditions. Plant extracts are comprised of diverse phytochemicals such as phenolic and flavonoid constituents, whereas EOs are rich in terpenes (e.g., monoterpenes and sesquiterpenes), terpenoids as well as low molecular weight aliphatic and aromatic compounds. Despite being a cheaper and safer alternative to synthetic pharmaceutically formulated drugs, the full therapeutic potential of plant-derived NPs has not been fully exploited as yet, particularly at the level of the pharmaceutical industry.

The current Special Issue therefore invites submissions of original research articles focusing on the chemical characterization and bioactivity screening of plant extracts and EOs. Phytochemical instrumental analyses, which are directed at the identification, quantification and structural elucidation of fractionated purified single entities and/or their complex mixtures, are prerequisites for submitted author contributions.

Prof. Dr. Mourad A. M. Aboul-Soud
Guest Editor

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Keywords

natural products
pharmaceutical activity
plant extracts
essential oils
chemical composition
GC-MS
LC-MS/MS

Published Papers (8 papers)

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Research

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9 pages, 900 KiB

Open AccessArticle

Development of a GC/Q-ToF-MS Method Coupled with Headspace Solid-Phase Microextraction to Evaluate the In Vitro Metabolism of β-Caryophyllene

by Joseph Lee, Mei Wang, Goutam Mondal, Ikhlas A. Khan and Charles R. Yates

Molecules 2022, 27(21), 7441; https://doi.org/10.3390/molecules27217441 - 02 Nov 2022

Viewed by 1185

Abstract

Sample preparation remains both a challenging and time-consuming process in the field of bioanalytical chemistry. Many traditional techniques often require multi-step processes, which can introduce additional errors to the analytical method. Given the complexity of many biological matrices, thorough analyte extraction presents a major challenge to researchers. In the present study, a headspace solid-phase microextraction (HS-SPME) coupled with a GC/Q-ToF-MS method, was developed to quantify in vitro metabolism of β-caryophyllene by both human liver microsome (HLM) and S9 liver fractions. Validation of the method was demonstrated both in terms of linearity (R² = 0.9948) and sensitivity with a limit of detection of 3 ng/mL and a limit of quantitation of 10 ng/mL. In addition, the method also demonstrated both inter- and intra-day precision with the relative standard deviation (RSD) being less than 10% with four concentrations ranging from 50–500 ng/mL. Since this method requires no solvents and minimal sample preparation, it provides a rapid and economical alternative to traditional extraction techniques. The method also eliminates the need to remove salts or buffers, which are commonly present in biological matrices. Although this method was developed to quantify in vitro metabolism of one analyte, it could easily be adapted to detect or quantify numerous volatiles and/or semi-volatiles found in biological matrices. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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17 pages, 5576 KiB

Open AccessArticle

Curcumin and Its Derivatives Induce Apoptosis in Human Cancer Cells by Mobilizing and Redox Cycling Genomic Copper Ions

by Mohammed Ahmed Ismail Alhasawi, Mohammad Aatif, Ghazala Muteeb, Mir Waqas Alam, Mohamed El Oirdi and Mohd Farhan

Molecules 2022, 27(21), 7410; https://doi.org/10.3390/molecules27217410 - 01 Nov 2022

Cited by 14 | Viewed by 2039

Abstract

Turmeric spice contains curcuminoids, which are polyphenolic compounds found in the Curcuma longa plant’s rhizome. This class of molecules includes curcumin, demethoxycurcumin, and bisdemethoxycurcumin. Using prostate cancer cell lines PC3, LNCaP, DU145, and C42B, we show that curcuminoids inhibit cell proliferation (measured by MTT assay) and induce apoptosis-like cell death (measured by DNA/histone ELISA). A copper chelator (neocuproine) and reactive oxygen species scavengers (thiourea for hydroxyl radical, superoxide dismutase for superoxide anion, and catalase for hydrogen peroxide) significantly inhibit this reaction, thus demonstrating that intracellular copper reacts with curcuminoids in cancer cells to cause DNA damage via ROS generation. We further show that copper-supplemented media sensitize normal breast epithelial cells (MCF-10A) to curcumin-mediated growth inhibition, as determined by decreased cell proliferation. Copper supplementation results in increased expression of copper transporters CTR1 and ATP7A in MCF-10A cells, which is attenuated by the addition of curcumin in the medium. We propose that the copper-mediated, ROS-induced mechanism of selective cell death of cancer cells may in part explain the anticancer effects of curcuminoids. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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14 pages, 3325 KiB

Open AccessArticle

Antioxidant, Antimicrobial and In Silico NADPH Oxidase Inhibition of Chemically-Analyzed Essential Oils Derived from Ballota deserti (Noë) Jury

by Basim R. Al Shammari

Molecules 2022, 27(19), 6636; https://doi.org/10.3390/molecules27196636 - 06 Oct 2022

Viewed by 1223

Abstract

Ballota deserti (Noë) Jury (B. deserti) is a medicinal plant used in Ayurvedic medicine. The chemical composition, antioxidant, antibacterial, and antifungal properties of essential oils from B. deserti (EOBD) against drug-resistant microorganisms were examined in this work. Hydrodistillation was used to extract EOBD, and gas chromatography–mass spectrometry was used to identify its constituents. Ferric reducing antioxidant power (FRAP), 1,1-diphenyl-2-picrylhydrazyl (DPPH), and total antioxidant capacity (TAC) were used to assess the antioxidant effect of EOBD. The disc diffusion agar and the microdilution tests were used in the assessment of the antibacterial properties of EOBD against clinically resistant pathogenic microorganisms. An in silico approach was used to evaluate the inhibitory potential of EOBD against NADPH oxidase. The yield of EOBD was 0.41%, and was primarily composed of linalool (37.82%), cineole (12.04%), and borneol (11.07%). EOBD had good antioxidant potency, with calculated values of 19.82 ± 1.14 µg/mL (DPPH), 64.78 ± 5.21 µg/mL (FRAP), 996.84 ± 20.18 µg EAA/ mg (TAC). Both Gram-negative and Gram-positive bacteria were inhibited by EOBD with inhibition zones ranging from 17.481.75 mm to 28.471.44 mm. EOBD exhibited MICs ranging from 10.78 g/mL to 22.48 g/mL when tested against bacteria using the minimum inhibitory concentration (MIC) assay. Similarly, impressive antifungal activity was observed against fungal strains with inhibition zone widths ranging from 16.761.83 to 36.791.35 mm. Results of MICs assay against fungi showed that EOBD had MICs values ranging from 15.32 ± 1.47 to 23.74 ± 1.54 µg/mL. Docking results showed that thujone, o-cymene, and butanoic acid contained in EOBD possessed strong activity against NADPH oxidase, with glide scores of −5.403, −5.344, and −4.973 Kcal/mol, respectively. In light of these findings, the EOBD may be seen as a potential source of chemical compounds with significant biological capabilities that can be advantageous as natural antioxidants and develop an effective weapon against a wide range of pathogenic bacteria. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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18 pages, 1232 KiB

Open AccessArticle

Chemical Composition, Antioxidant and Antiproliferative Activities of Taraxacum officinale Essential Oil

by Fatima Zahra Kamal, Radu Lefter, Cosmin-Teodor Mihai, Hanane Farah, Alin Ciobica, Ahmad Ali, Iulian Radu, Ioannis Mavroudis and Abdellah Ech-Chahad

Molecules 2022, 27(19), 6477; https://doi.org/10.3390/molecules27196477 - 01 Oct 2022

Cited by 3 | Viewed by 2298

Abstract

Taraxacum officinale (TO) has been historically used for medicinal purposes due to its biological activity against specific disorders. To investigate the antioxidant and the antiproliferativepotential of TO essential oil in vitro and in vivo, the chemical composition of the essential oil was analyzed by GC-MS. The in vivo antioxidant capacity was assessed on liver and kidney homogenate samples from mice subjected to acetaminophen-induced oxidative stress and treated with TO essential oil (600 and 12,000 mg/kg BW) for 14 days. The in vitro scavenging activity was assayed using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the reducing power methods. The cytotoxic effects against the HeLa cancer cell line were analyzed. The GC-MS analysis showed the presence of 34 compounds, 8 of which were identified as major constituents. The TO essential oil protected mice’s liver and kidneys from acetaminophen-induced oxidative stress by enhancing antioxidant enzymes (catalase, superoxide dismutase, and glutathione) and lowering malondialdehyde levels. In vitro, the TO essential oil demonstrated low scavenging activity against DPPH (IC₅₀ = 2.00 ± 0.05 mg/mL) and modest reducing power (EC₅₀ = 0.963 ± 0.006 mg/mL). The growth of the HeLa cells was also reduced by the TO essential oil with an inhibition rate of 83.58% at 95 µg/mL. Current results reveal significant antioxidant and antiproliferative effects in a dose-dependent manner and suggest that Taraxacum officinale essential oil could be useful in formulations for cancer therapy. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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15 pages, 782 KiB

Open AccessArticle

Promising Antioxidant and Antimicrobial Potencies of Chemically-Profiled Extract from Withania aristata (Aiton) Pauquy against Clinically-Pathogenic Microbial Strains

by Alhusain J. Alzahrani

Molecules 2022, 27(11), 3614; https://doi.org/10.3390/molecules27113614 - 04 Jun 2022

Cited by 5 | Viewed by 1691

Abstract

Withania aristata (Aiton) Pauquy, a medicinal plant endemic to North African Sahara, is widely employed in traditional herbal pharmacotherapy. In the present study, the chemical composition, antioxidant, antibacterial, and antifungal potencies of extract from the roots of Withania aristata (Aiton) Pauquy (RWA) against drug-resistant microbes were investigated. Briefly, RWA was obtained by maceration with hydro-ethanol and its compounds were identified by use of high-performance liquid chromatography (HPLC). The antioxidant activity of RWA was determined by use of ferric-reducing antioxidant power (FRAP), 1,1-diphenyl-2-picrylhydrazyl (DPPH), and total antioxidant capacity (TAC). The evaluation of the antimicrobial potential of RWA was performed against drug-resistant pathogenic microbial strains of clinical importance by use of the disc diffusion agar and microdilution assays. Seven compounds were identified in RWA according to HPLC analysis, including cichoric acid, caffeic acid, apigenin, epicatechin, luteolin, quercetin, and p-catechic acid. RWA had excellent antioxidant potency with calculated values of 14.0 ± 0.8 µg/mL (DPPH), 0.37 ± 0.08 mg/mL (FRAP), 760 ± 10 mg AAE/g (TAC), and 81.4% (β-carotene). RWA demonstrated good antibacterial potential against both Gram-negative and Gram-positive bacteria, with inhibition zone diameters ranging from 15.24 ± 1.31 to 19.51 ± 0.74 mm, while all antibiotics used as drug references were infective, except for Oxacillin against S. aureus. Results of the minimum inhibitory concentration (MIC) assay against bacteria showed that RWA had MIC values ranging from 2.13 to 4.83 mg/mL compared to drug references, which had values ranging from 0.031 ± 0.003 to 0.064 ± 0.009 mg/mL. Similarly, respectable antifungal potency was recorded against the fungal strains with inhibition zone diameters ranging from 25.65 ± 1.14 to 29.00 ± 1.51 mm compared to Fluconazole, used as a drug reference, which had values ranging from 31.69 ± 1.92 to 37.74 ± 1.34 mg/mL. Results of MIC assays against fungi showed that RWA had MIC values ranging from 2.84 ± 0.61 to 5.71 ± 0.54 mg/mL compared to drug references, which had values ranging from 2.52 ± 0.03 to 3.21 ± 0.04 mg/mL. According to these outcomes, RWA is considered a promising source of chemical compounds with potent biological properties that can be beneficial as natural antioxidants and formulate a valuable weapon in the fight against a broad spectrum of pathogenic microbes. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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15 pages, 1486 KiB

Open AccessArticle

Antioxidant, Antimicrobial, and Insecticidal Properties of a Chemically Characterized Essential Oil from the Leaves of Dittrichia viscosa L.

by Ibrahim Mssillou, Abdelkrim Agour, Aimad Allali, Hamza Saghrouchni, Mohammed Bourhia, Abdelfattah El Moussaoui, Ahmad Mohammad Salamatullah, Abdulhakeem Alzahrani, Mourad A. M. Aboul-Soud, John P. Giesy, Badiaa Lyoussi and Elhoussine Derwich

Molecules 2022, 27(7), 2282; https://doi.org/10.3390/molecules27072282 - 31 Mar 2022

Cited by 21 | Viewed by 2428

Abstract

Since some synthetic insecticides cause damage to human health, compounds in plants can be viable alternatives to conventional synthetic pesticides. Dittrichia viscosa L. is a perennial Mediterranean plant known to possess biological activities, including insecticidal properties. The chemical composition of an essential oil (EOD) from D. viscosa, as well as its antioxidant, antimicrobial, and insecticidal effects on the cowpea weevil (Callosobruchus maculatus) were determined. Forty-one volatile compounds were identified in EOD, which accounted for 97.5% of its constituents. Bornyl acetate (41%) was a major compound, followed by borneol (9.3%), α-amorphene (6.6%), and caryophyllene oxide (5.7%). EOD exhibited significant antioxidant activity in all tests performed, with an IC₅₀ of 1.30 ± 0.05 mg/mL in the DPPH test and an EC₅₀ equal to 36.0 ± 2.5 mg/mL in the FRAP assay. In the phosphor-molybdenum test, EOD results ranged from 39.81 ± 0.7 to 192.1 ± 0.8 mg AAE/g E. EOD was active on E. coli (9.5 ± 0.5 mm), S. aureus (31.0 ± 1.5 mm), C. albicans (20.4 ± 0.5 mm), and S. cerevisiae (28.0 ± 1.0 mm), with MICs ranging from 0.1 mg/mL to 3.3 mg/mL. We found that 1 µL of EOD caused 97.5 ± 5.0% insect mortality after 96 h in the inhalation test and 60.0 ± 8.3% in the ingestion assay. The median lethal concentration (LC₅₀) was 7.8 ± 0.3 μL EO/L, while the effective concentration in the ingestion test (LC₅₀) was 15.0 ± 2.1 μL EO/L. We found that 20 µL of EOD caused a reduction of more than 91% of C. maculatus laid eggs. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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15 pages, 20417 KiB

Open AccessArticle

Antioxidant and Antimicrobial Activities of Chemically-Characterized Essential Oil from Artemisia aragonensis Lam. against Drug-Resistant Microbes

by Khalid Chebbac, Hazem K. Ghneim, Abdelfattah El Moussaoui, Mohammed Bourhia, Azeddin El Barnossi, Zineb Benziane Ouaritini, Ahmad Mohammad Salamatullah, Abdulhakeem Alzahrani, Mourad A. M. Aboul-Soud, John P. Giesy and Raja Guemmouh

Molecules 2022, 27(3), 1136; https://doi.org/10.3390/molecules27031136 - 08 Feb 2022

Cited by 35 | Viewed by 3555

Abstract

This study investigated the chemical composition, antioxidant and antimicrobial activity of essential oil extracted from Artemisia aragonensis Lam. (EOA). Hydrodistillation was employed to extract EOA. Gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometry analyses (GC-MS) were used to determine the phytochemical composition of EOA. Antioxidant potential was examined in vitro by use of three tests: 2.2-diphenyl-1-picrilhidrazil (DPPH), ferric reducing activity power (FRAP) and total antioxidant capacity assay (TAC). Agar diffusion and microdilution bioassays were used to assess antimicrobial activity. GC/MS and GC-FID detected 34 constituents in the studied EOA. The major component was Camphor (24.97%) followed by Borneol (13.20%), 1,8 Cineol (10.88%), and Artemisia alcohol (10.20%). EOA exhibited significant antioxidant activity as measured by DPPH and FRAP assays, with IC₅₀ and EC₅₀ values of 0.034 ± 0.004 and 0.118 ± 0.008 mg/mL, respectively. EOA exhibited total antioxidant capacity of 7.299 ± 1.774 mg EAA/g. EOA exhibited potent antibacterial activity as judged by the low minimum inhibitory concentration (MIC) values against selected clinically-important pathogenic bacteria. MIC values of 6.568 ± 1.033, 5.971 ± 1.033, 7.164 ± 0.0 and 5.375 ± 0.0 μg/mL were observed against S. aureus, B. subtills, E. coli 97 and E. coli 57, respectively. EOA displayed significant antifungal activity against four strains of fungi: F. oxysporum, C. albicans, A. flavus and A. niger with values of 21.50 ± 0.43, 5.31 ± 0.10, 21.50 ± 0.46 and 5.30 ± 0.036 μg/mL, respectively. The results of the current study highlight the importance of EOA as an alternative source of natural antioxidant and antibacterial drugs to combat antibiotic-resistant microbes and free radicals implicated in the inflammatory responses accompanying microbial infection. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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Review

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21 pages, 5868 KiB

Open AccessReview

Efforts in Bioprospecting Research: A Survey of Novel Anticancer Phytochemicals Reported in the Last Decade

by Saheed O. Anifowose, Wejdan S. N. Alqahtani, Badr A. Al-Dahmash, Florenz Sasse, Maroua Jalouli, Mourad A. M. Aboul-Soud, Ahmed Y. Badjah-Hadj-Ahmed and Yasser A. Elnakady

Molecules 2022, 27(23), 8307; https://doi.org/10.3390/molecules27238307 - 28 Nov 2022

Cited by 3 | Viewed by 1946

Abstract

Bioprospecting natural products to find prominent agents for medical application is an area of scientific endeavor that has produced many clinically used bioactive compounds, including anticancer agents. These compounds come from plants, microorganisms, and marine life. They are so-called secondary metabolites that are important for a species to survive in the hostile environment of its respective ecosystem. The kingdom of Plantae has been an important source of traditional medicine in the past and is also enormously used today as an exquisite reservoir for detecting novel bioactive compounds that are potent against hard-to-treat maladies such as cancer. Cancer therapies, especially chemotherapies, are fraught with many factors that are difficult to manage, such as drug resistance, adverse side effects, less selectivity, complexity, etc. Here, we report the results of an exploration of the databases of PubMed, Science Direct, and Google Scholar for bioactive anticancer phytochemicals published between 2010 and 2020. Our report is restricted to new compounds with strong-to-moderate bioactivity potential for which mass spectroscopic structural data are available. Each of the phytochemicals reported in this review was assigned to chemical classes with peculiar anticancer properties. In our survey, we found anticancer phytochemicals that are reported to have selective toxicity against cancer cells, to sensitize MDR cancer cells, and to have multitarget effects in several signaling pathways. Surprisingly, many of these compounds have limited follow-up studies. Detailed investigations into the synthesis of more functional derivatives, chemical genetics, and the clinical relevance of these compounds are required to achieve safer chemotherapy. Full article

(This article belongs to the Special Issue Pharmacological Activities of Chemically-Characterized Plant-Derived Essential Oils and Extracts)

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