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Keywords = 1,8-cineole metabolism

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23 pages, 3020 KiB  
Article
Effects of Monoterpene-Based Biostimulants on Chickpea (Cicer arietinum L.) Plants: Functional and Molecular Insights
by Lamyae Et-Tazy, Riccardo Fedeli, Oussama Khibech, Abdeslam Lamiri, Allal Challioui and Stefano Loppi
Biology 2025, 14(6), 657; https://doi.org/10.3390/biology14060657 - 5 Jun 2025
Cited by 1 | Viewed by 853
Abstract
This study evaluated the physiological and biochemical responses of chickpea (Cicer arietinum L.) to foliar application of cineole, carvacrol, and thymol at concentrations of 500 and 1000 ppm. Carvacrol at 1000 ppm significantly enhanced fresh biomass (+15.4%) and aerial biomass (+46.2%), whereas [...] Read more.
This study evaluated the physiological and biochemical responses of chickpea (Cicer arietinum L.) to foliar application of cineole, carvacrol, and thymol at concentrations of 500 and 1000 ppm. Carvacrol at 1000 ppm significantly enhanced fresh biomass (+15.4%) and aerial biomass (+46.2%), whereas thymol significantly reduced plant height (−20.2%) and overall biomass, yet notably increased chlorophyll content (+23.3%) and vitamin C levels (+41.4%) at the same concentration. Cineole significantly improved antioxidant capacity by increasing total phenolic content (+15.5% at 1000 ppm) and total flavonoid content (+19.1% at 500 ppm), but simultaneously decreased soluble protein synthesis and chlorophyll content (−39% at 500 ppm). Mineral analysis showed notable increases in calcium content following treatment with cineole (+30.5% at 1000 ppm) and carvacrol (+32% at 500 ppm), while thymol at 1000 ppm significantly reduced phosphorus, potassium, manganese, iron, copper, and zinc accumulation. Molecular docking and dynamic simulations revealed strong interactions of thymol and carvacrol with essential enzymes, specifically ascorbate peroxidase and phenylalanine ammonia-lyase, which are involved in antioxidant and phenolic metabolism pathways. These molecular interactions suggest potential contributions of thymol and carvacrol to plant stress resilience mechanisms, although further experimental validation is needed to confirm their roles in vivo. These findings emphasize the importance of optimizing monoterpene concentrations, indicating that carefully calibrated treatments could effectively enhance chickpea growth, nutritional quality, and stress tolerance within sustainable agricultural practices. Full article
(This article belongs to the Section Plant Science)
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17 pages, 1031 KiB  
Article
Comprehensive Analysis of Volatile Organic Compounds and Their Impact on Apple Quality Following Some Essential Oil Treatments Against Botrytis cinerea
by Sinem Karakus, Harlene Hatterman-Valenti, Muge Sahin and Ozkan Kaya
Horticulturae 2024, 10(12), 1359; https://doi.org/10.3390/horticulturae10121359 - 18 Dec 2024
Viewed by 1394
Abstract
The susceptibility of apples to post-harvest decay by the fungus Botrytis cinerea has prompted innovative research into alternative preservation methods. In this regard, essential oils (EOs) have emerged as promising candidates due to their natural origin and potential antimicrobial properties. Investigating the biological [...] Read more.
The susceptibility of apples to post-harvest decay by the fungus Botrytis cinerea has prompted innovative research into alternative preservation methods. In this regard, essential oils (EOs) have emerged as promising candidates due to their natural origin and potential antimicrobial properties. Investigating the biological significance of EO blends is crucial for understanding their potential antimicrobial mechanisms and evaluating their capacity to modulate metabolic responses that could inhibit post-harvest fungal decay in fruit tissues. This study delves into the intricate chemistry of apples when subjected to various EO treatments, shedding light on the profound changes in alcohols, esters, C6 compounds, terpenes, and volatile compounds. Based on our results, terpene concentrations exhibit significant variations with α-Pinene ranging from 13.4 µg L−1 in Fungus + Thymol + 1,8-Cineole treatment (Fun+Thy+Cin) to 28.7 µg L−1 in Fungus + Thymol + 1,8-Cineole + Eugenol treatment (Fun+Thy+Cin+Eug), and β-Pinene concentrations spanning 19.3 µg L−1 in Fungus + 1,8-Cineole + Eugenol treatment (Fun+Cin+Eug) to 45.5 µg L−1 in Fungus + Thymol + 1,8-Cineole + Eugenol treatment (Fun+Thy+Cin+Eug). Ester elaboration presents marked changes, with ethyl octanoate peaking at 715.7 µg L−1 in Fungus + Thymol + 1,8-Cineole + Eugenol treatment (Fun+Thy+Cin+Eug) and ethyl propionate reaching 152.9 µg L−1 in Fungus + Thymol treatment (Fun+Thy). The volatile compound dynamics also demonstrate significant variations, with hexanoic acid concentrations ranging from 0.1 to 0.2 among treatments and 3-Methylbutanal displaying concentrations from 0.8 to 6.4, with the highest concentration observed in the Control. The essential oil combination of Thymol, Eugenol, and 1,8-Cineol (Fun+Thy+Cin+Eug) had the most significant impact on the volatile compound content in the fruits. The findings from this study unveil the intricate responses of apple chemistry to various EO treatments. These insights hold promise for enhancing post-harvest apple preservation strategies through the modulation of EO treatments. Full article
(This article belongs to the Special Issue Advances in Postharvest Packaging and Preservation Techniques)
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17 pages, 704 KiB  
Article
Agronomic Evaluation and Chemical Characterization of Salvia lavandulifolia Vahl. over 3 Consecutive Years Cultivated Under Harsh Climatic Conditions in Southeast Spain
by Gustavo J. Cáceres-Cevallos, María Quílez, Gonzalo Ortiz de Elguea-Culebras, Enrique Melero-Bravo, Raúl Sánchez-Vioque and María J. Jordán
Plants 2024, 13(21), 3022; https://doi.org/10.3390/plants13213022 - 29 Oct 2024
Cited by 1 | Viewed by 1071
Abstract
The cultivation of Salvia lavandulifolia, Spanish sage, makes an important contribution to the economy of many rural areas in Southeastern Spain. This aromatic plant species is characterized by high intraspecific variability, which makes the selection process for the establishment of homogeneous crops [...] Read more.
The cultivation of Salvia lavandulifolia, Spanish sage, makes an important contribution to the economy of many rural areas in Southeastern Spain. This aromatic plant species is characterized by high intraspecific variability, which makes the selection process for the establishment of homogeneous crops difficult. Additionally, imminent climate change threatens to reduce its production, especially when cultivated in drylands. Therefore, to guarantee the continued production of this type of sage, it is essential to study its agronomic behavior and production quality. For this, clones from four ecotypes were cultivated for three years, assessing changes in their biomass production, essential oil yield and quality, and phenolic fraction, as well as the corresponding antioxidant activity. The results suggest that essential oil yield is genetically predetermined, greater biomass not being associated with higher quantities of essential oil. Weather conditions affected both essential oil and phenolic fraction secondary metabolism. Under very harsh conditions, Spanish sage produces higher concentrations of camphor and 1,-8-cineole along with luteolin-7-O-glucoside, and lithospermic, rosmarinic, and salvianolic A acids in its phenolic fraction. The synthesis of these components helps the species to withstand the hot and dry conditions typical of southeast Spain. Full article
(This article belongs to the Special Issue Propagation and Cultivation of Medicinal Plants―2nd Edition)
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18 pages, 3813 KiB  
Article
Integration of RNA-Seq and Metabolite Analysis Reveals the Key Floral Scent Biosynthetic Genes in Herbaceous Peony
by Shadrack Kanyonji Kimani, Shuxian Wang, Jinyi Xie, Tingting Bao, Xiaotong Shan, Hongjie Li, Adnan, Li Wang, Xiang Gao and Yueqing Li
Horticulturae 2024, 10(6), 617; https://doi.org/10.3390/horticulturae10060617 - 10 Jun 2024
Cited by 2 | Viewed by 2127
Abstract
Floral scent is an essential and genetically complex trait in herbaceous peonies (Paeonia lactiflora Pall.); however, specific genes related to metabolic and regulatory networks remain scantily studied. Our study integrated metabolite profiling and RNA-sequencing to screen floral scent biosynthetic genes. Hence, the [...] Read more.
Floral scent is an essential and genetically complex trait in herbaceous peonies (Paeonia lactiflora Pall.); however, specific genes related to metabolic and regulatory networks remain scantily studied. Our study integrated metabolite profiling and RNA-sequencing to screen floral scent biosynthetic genes. Hence, the major molecules identified by headspace collection combined with cultivar-specific GC-MS analysis were geraniol, β-caryophyllene, 2-phenylethanol (2-PE), citronellol, and 1,8-cineole. Genes related to terpenoids and 2-PE biosynthesis were identified after the assembly and annotation of the P. lactiflora transcriptomes. Eight angiosperm-specific terpene synthases (TPSs) from the TPS-a and TPS-b clades, as well as enzymes linked to 2-PE synthesis such as aromatic amino acid decarboxylase (AADC), phenylacetaldehyde reductase (PAR), and geranial reductase (GER) were identified. The biochemical analysis of the enzymes encoded by PlPAR1 and PlGER1 generated 2-PE from phenylacetaldehyde (PAld). The pairwise alignment of AADC1 reveals a splice variant lacking a 124 bp fragment, thus highlighting the possible role of alternative splicing in modulating floral scent composition. This study offers insights into the molecular-level biosynthesis of terpenoids and 2-PE in Peonia taxa, and provides the basis for the functional characterization, breeding, and bioengineering of prospective candidate genes for the production of floral volatiles in the Paeonia genus. Full article
(This article belongs to the Section Floriculture, Nursery and Landscape, and Turf)
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24 pages, 4134 KiB  
Article
Effect of Light Conditions, Trichoderma Fungi and Food Polymers on Growth and Profile of Biologically Active Compounds in Thymus vulgaris and Thymus serpyllum
by Kamila Kulbat-Warycha, Justyna Nawrocka, Liliana Kozłowska and Dorota Żyżelewicz
Int. J. Mol. Sci. 2024, 25(9), 4846; https://doi.org/10.3390/ijms25094846 - 29 Apr 2024
Cited by 3 | Viewed by 1827
Abstract
The research investigates the influence of different lighting conditions and soil treatments, in particular the application of food polymers separately and in combination with spores of Trichoderma consortium, on the growth and development of herbs—Thymus vulgaris and Thymus serpyllum. The metabolic [...] Read more.
The research investigates the influence of different lighting conditions and soil treatments, in particular the application of food polymers separately and in combination with spores of Trichoderma consortium, on the growth and development of herbs—Thymus vulgaris and Thymus serpyllum. The metabolic analysis focuses on detecting changes in the levels of biologically active compounds such as chlorophyll a and b, anthocyanins, carotenoids, phenolic compounds (including flavonoids), terpenoids, and volatile organic compounds with potential health-promoting properties. By investigating these factors, the study aims to provide insights into how environmental conditions affect the growth and chemical composition of selected plants and to shed light on potential strategies for optimising the cultivation of these herbs for the improved quality and production of bioactive compounds. Under the influence of additional lighting, the growth of T. vulgaris and T. serpyllum seedlings was greatly accelerated, resulting in an increase in shoot biomass and length, and in the case of T. vulgaris, an increase in carotenoid and anthocyanin contents. Regarding secondary metabolites, the most pronounced changes were observed in total antioxidant capacity and flavonoid content, which increased significantly under the influence of additional lighting. The simultaneous or separate application of Trichoderma and food polymers resulted in an increase in flavonoid content in the leaves of both Thymus species. The increase in terpenoid content under supplemental light appears to be related to the presence of Trichoderma spores as well as food polymers added to the soil. However, the nature of these changes depends on the thyme species. Volatile compounds were analysed using an electronic nose (E-nose). Eight volatile compounds (VOCs) were tentatively identified in the vapours of T. vulgaris and T. serpyllum: α-pinene, myrcene, α-terpinene, γ-terpinene; 1,8-cineole (eucalyptol), thymol, carvacrol, and eugenol. Tendencies to increase the percentage of thymol and γ-terpinene under supplemental lighting were observed. The results also demonstrate a positive effect of food polymers and, to a lesser extent, Trichoderma fungi on the synthesis of VOCs with health-promoting properties. The effect of Trichoderma and food polymers on individual VOCs was positive in some cases for thymol and γ-terpinene. Full article
(This article belongs to the Special Issue Regulation and Application of Bioactive Metabolites in Plants)
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33 pages, 7318 KiB  
Article
Chemical Composition Antioxidant and Anti-Inflammatory Activities of Myrtus communis L. Leaf Extract: Forecasting ADMET Profiling and Anti-Inflammatory Targets Using Molecular Docking Tools
by Samia Belahcene, Widad Kebsa, Tomilola Victor Akingbade, Haruna Isiyaku Umar, Damilola Alex Omoboyowa, Abdulaziz A. Alshihri, Adel Abo Mansour, Abdulaziz Hassan Alhasaniah, Mohammed A. Oraig, Youssef Bakkour and Essaid Leghouchi
Molecules 2024, 29(4), 849; https://doi.org/10.3390/molecules29040849 - 14 Feb 2024
Cited by 7 | Viewed by 4454
Abstract
Compounds derived from natural sources continue to serve as chemical scaffolds for designing prophylactic/therapeutic options for human healthcare. In this study, we aimed to systematically unravel the chemical profile and antioxidant and anti-inflammatory activities of myrtle methanolic extract (MMEx) using in vitro, in [...] Read more.
Compounds derived from natural sources continue to serve as chemical scaffolds for designing prophylactic/therapeutic options for human healthcare. In this study, we aimed to systematically unravel the chemical profile and antioxidant and anti-inflammatory activities of myrtle methanolic extract (MMEx) using in vitro, in vivo, and in silico approaches. High levels of TPC (415.85 ± 15.52 mg GAE/g) and TFC (285.80 ± 1.64 mg QE/g) were observed. Mass spectrophotometry (GC-MS) analysis revealed the presence of 1,8-cineole (33.80%), α-pinene (10.06%), linalool (4.83%), p-dimethylaminobenzophenone (4.21%), thunbergol (4%), terpineol (3.60%), cis-geranyl acetate (3.25%), and totarol (3.30%) as major compounds. MMEx induced pronounced dose-dependent inhibition in all assays, and the best antioxidant activity was found with H2O2, with an IC50 of 17.81 ± 3.67 µg.mL−1. MMEx showed a good anti-inflammatory effect in vivo by limiting the development of carrageenan-induced paw edema. The pharmacokinetic profiles of the active molecules were determined using the SwissADME website, followed by virtual screening against anti-inflammatory targets including phospholipase A2 (PLA-2), cyclooxygenase-2 (COX-2), tumor necrosis factor alpha (TNF-α), interleukin-1β (IL-1β), and NF-κB. A pharmacokinetic study revealed that the molecules have good absorption, distribution, and metabolism profiles, with negative organ toxicity. Among the compounds identified by GC-MS analysis, pinostrobin chalcone, cinnamyl cinnamate, hedycaryol, totarol, and p-dimethylaminobenzophenone were observed to have good binding scores, thus appreciable anti-inflammatory potential. Our study reveals that MMEx from Algerian Myrtus communis L. can be considered to be a promising candidate for alleviating many health complaints associated with oxidative stress and inflammation. Full article
(This article belongs to the Section Natural Products Chemistry)
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16 pages, 1603 KiB  
Article
A New Lavender (Lavandula multifida L.) Ecotype from Arid Tunisia, with Differential Essential Oil Composition and Higher Antimicrobial Potential
by Mohanad Lateef Tofah, Khalil Mseddi, Omar K. Al-Abbasi, Ahmed Ben Yazid, Ahmed Khechine, Radhouane Gdoura and Lamia Khannous
Life 2023, 13(1), 103; https://doi.org/10.3390/life13010103 - 30 Dec 2022
Cited by 8 | Viewed by 3437
Abstract
The lavender Lavandula multifida L., a medicinal plant grown in arid regions of Tunisia, was recently considered an endangered species; thus, its habitats regressed to some difficult zones in terms of access, such as the watershed of Oued Agareb in central-eastern Tunisia. This [...] Read more.
The lavender Lavandula multifida L., a medicinal plant grown in arid regions of Tunisia, was recently considered an endangered species; thus, its habitats regressed to some difficult zones in terms of access, such as the watershed of Oued Agareb in central-eastern Tunisia. This species was recorded only in deep and narrow shady Wadi of the watershed and benefited from protection against overgrazing, erosion and sunlight. L. multifida was rarely observed in an open area, such as a plateau or large-bed valley. The plant’s metabolism is linked to its response to environmental conditions, which is of particular interest to understanding the components of the considered population of L. multifida. Consequently, biochemical and antimicrobial analyses have been evaluated. Using gas chromatography-mass spectrometry (GC-MS) analysis reveals that among the 58 compounds identified in L. multifida essential oil extracted from aboveground plant tissues, camphor was the major component (15.68%), followed by 1,8-cineole (14.14%) and alpha-pinene (13.82%). Moreover, it has been observed that Escherichia coli was more susceptible than Staphylococcus aureus to the antimicrobial properties of L. multifida essential oil, while in the case of camphor, S. aureus was more susceptible than E. coli. The protected population of L. multifida exhibits a distinctive vegetative development and growth cycle, resulting in specific secondary metabolites and distinguished antimicrobial activity. Full article
(This article belongs to the Special Issue The Discovery and Application of Phytochemicals and Bio Actives)
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17 pages, 7907 KiB  
Article
Essential Oil Composition and Antioxidant and Antifungal Activities of Two Varieties of Ocimum basilicum L. (Lamiaceae) at Two Phenological Stages
by Guedri Mkaddem Mounira, Zrig Ahlem, Ben Abdallah Mariem, Mehrez Romdhane, Mohammad K. Okla, Abdulrahman Al-Hashimi, Yasmeen A. Alwase, Mahmoud M. Madnay, Gehad AbdElgayed, Han Asard, Gerrit T. S. Beemster and Hamada AbdElgawad
Agronomy 2022, 12(4), 825; https://doi.org/10.3390/agronomy12040825 - 28 Mar 2022
Cited by 24 | Viewed by 3835
Abstract
Ocimum basilicum is a valuable source of bioactive metabolites with high preventive and therapeutic effectiveness. Here we aimed to investigate the effect of phenological stages (vegetative and flowering stages) on essential oil composition and biological activities of two varieties of O. basilicum (Fino [...] Read more.
Ocimum basilicum is a valuable source of bioactive metabolites with high preventive and therapeutic effectiveness. Here we aimed to investigate the effect of phenological stages (vegetative and flowering stages) on essential oil composition and biological activities of two varieties of O. basilicum (Fino Verde variety and Genovese varieties). To this end, the level of essential oils, flavonoids and phenols, as well as antioxidant and antifungal activities were measured. At the metabolic level, essential oil at vegetative stage of O. bailicum Fino Verde and Genovese variety was constituted by 22 and 26 compounds representing 71.68% and 82.54% of the total oil, respectively. Where germacrene D (10.07%), bicyclogermacrene (6.07%) and β-elemene (4.88%) were the most present components in Fino Verde variety. Moreover, 22.19% are oxygenated monoterpenes represented mainly by the linalool (15.18%) and 1.8 cineole (6.36%) in Genovese variety. The individuals of essential oils were significantly increased to 40 components in Fino Verde variety (98.01% of total essential oil) and decreased to 15 components (95.6% of total essential oil) in Genovese variety at flowering stage. At this stage, the oxygenated monoterpenes (78.4%) were the major fraction represented by linalool (40.1%) and 1.8 cineole (30.96%) in Fino Verde variety, however 64.69% were esters which mainly represented by the methyl cinnamate (64.69%), and 16.83% of oxygenated monoterpenes and Linalool (12.7%) were recorded for Genovese variety. Genovese variety showed the highest levels at both vegetative and flowering stage compared to Fino Verde variety. At flowering stage, the two varieties showed high antioxidant and antifungal activities. Overall, O. basilicum properties offer prospects for their use as a source, particularly at flowering stage to extend new medicines based on natural bioactive molecules. Full article
(This article belongs to the Special Issue Bioactivity of Natural Products from Raw Horticultural Crops)
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14 pages, 1114 KiB  
Article
In Vitro Hepatic Assessment of Cineole and Its Derivatives in Common Brushtail Possums (Trichosurus vulpecula) and Rodents
by Ravneel R. Chand, Mhairi Nimick, Belinda Cridge and Rhonda J. Rosengren
Biology 2021, 10(12), 1326; https://doi.org/10.3390/biology10121326 - 15 Dec 2021
Cited by 4 | Viewed by 2561
Abstract
Folivore marsupials, such as brushtail possum (Trichosurus Vulpecula) and koala (Phascolarctos cinereus), can metabolise higher levels of dietary terpenes, such as cineole, that are toxic to eutherian mammals. While the highly efficient drug metabolising enzymes, cytochrome P450 3A (CYP3A) [...] Read more.
Folivore marsupials, such as brushtail possum (Trichosurus Vulpecula) and koala (Phascolarctos cinereus), can metabolise higher levels of dietary terpenes, such as cineole, that are toxic to eutherian mammals. While the highly efficient drug metabolising enzymes, cytochrome P450 3A (CYP3A) and phase II conjugating enzymes (UDP-glucuronosyltransferase, UGT), are involved in the metabolism of high levels of dietary terpenes, evidence for inhibitory actions on these enzymes by these terpenes is scant. Thus, this study investigated the effect of cineole and its derivatives on catalytic activities of hepatic CYP3A and UGT in mice, rats, and possums. Results showed that cineole (up to 50 µM) and its derivatives (up to 25 µM) did not significantly inhibit CYP3A and UGT activities in mice, rats, and possums (both in silico and in vitro). Interestingly, basal hepatic CYP3A catalytic activity in the possums was ~20% lower than that in rats and mice. In contrast, possums had ~2-fold higher UGT catalytic activity when compared to mice and rats. Thus, these basal enzymatic differences may be further exploited in future pest management strategies. Full article
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15 pages, 649 KiB  
Article
Effects of Biostimulants on the Chemical Composition of Essential Oil and Hydrosol of Lavandin (Lavandula x intermedia Emeric ex Loisel.) Cultivated in Tuscan-Emilian Apennines
by Eleonora Truzzi, Stefania Benvenuti, Davide Bertelli, Enrico Francia and Domenico Ronga
Molecules 2021, 26(20), 6157; https://doi.org/10.3390/molecules26206157 - 12 Oct 2021
Cited by 15 | Viewed by 3321
Abstract
In recent years, it has been shown that biostimulants can efficiently enhance plant metabolic processes, leading to an increased production of essential oil (EO) in aromatic plants. The present study aimed to evaluate the effects of two different commercial biostimulants composed of amino [...] Read more.
In recent years, it has been shown that biostimulants can efficiently enhance plant metabolic processes, leading to an increased production of essential oil (EO) in aromatic plants. The present study aimed to evaluate the effects of two different commercial biostimulants composed of amino acids and seaweed extract, normally used for food organic crops, on the production and composition of EO and hydrosol of Lavandula x intermedia, cultivar “Grosso”. The products were applied during 2020 growing season on lavender crops in three different locations of the Northern Italian (Emilia-Romagna Region) Apennines. Plants were harvested and EOs extracted by steam distillation and analyzed by gas chromatography. Both biostimulants affected the yield of EO per plant (+11% to +49% depending on the treatment/farm combination) without significantly changing the chemical composition of EOs and hydrosols. Conversely, the composition of EOs and hydrosols are related to the location, and the main compounds of “Grosso” cultivar, limonene, 1,8-cineole, cis-ocimene, linalool, camphor, borneol, terpinen-4-ol, and linalyl acetate, show different ratios at the experimental test sites. The differences might be due to the sunlight exposure and various maintenance of the crops over the years. In conclusion, these results suggest that the employment of biostimulants on lavandin crops do not endanger the quality of the EO while increasing biomass production and promoting the sustainability of the crop. Full article
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19 pages, 2927 KiB  
Article
3D-ALMOND-QSAR Models to Predict the Antidepressant Effect of Some Natural Compounds
by Speranta Avram, Miruna Silvia Stan, Ana Maria Udrea, Cătălin Buiu, Anca Andreea Boboc and Maria Mernea
Pharmaceutics 2021, 13(9), 1449; https://doi.org/10.3390/pharmaceutics13091449 - 10 Sep 2021
Cited by 15 | Viewed by 3613
Abstract
The current treatment of depression involves antidepressant synthetic drugs that have a variety of side effects. In searching for alternatives, natural compounds could represent a solution, as many studies reported that such compounds modulate the nervous system and exhibit antidepressant effects. We used [...] Read more.
The current treatment of depression involves antidepressant synthetic drugs that have a variety of side effects. In searching for alternatives, natural compounds could represent a solution, as many studies reported that such compounds modulate the nervous system and exhibit antidepressant effects. We used bioinformatics methods to predict the antidepressant effect of ten natural compounds with neuroleptic activity, reported in the literature. For all compounds we computed their drug-likeness, absorption, distribution, metabolism, excretion (ADME), and toxicity profiles. Their antidepressant and neuroleptic activities were predicted by 3D-ALMOND-QSAR models built by considering three important targets, namely serotonin transporter (SERT), 5-hydroxytryptamine receptor 1A (5-HT1A), and dopamine D2 receptor. For our QSAR models we have used the following molecular descriptors: hydrophobicity, electrostatic, and hydrogen bond donor/acceptor. Our results showed that all compounds present drug-likeness features as well as promising ADME features and no toxicity. Most compounds appear to modulate SERT, and fewer appear as ligands for 5-HT1A and D2 receptors. From our prediction, linalyl acetate appears as the only ligand for all three targets, neryl acetate appears as a ligand for SERT and D2 receptors, while 1,8-cineole appears as a ligand for 5-HT1A and D2 receptors. Full article
(This article belongs to the Special Issue In Silico Strategies for Prospective Drug Repositionings)
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18 pages, 2725 KiB  
Article
Antioxidant Activities of a New Chemotype of Piper cubeba L. Fruit Essential Oil (Methyleugenol/Eugenol): In Silico Molecular Docking and ADMET Studies
by Fahad Alminderej, Sana Bakari, Tariq I. Almundarij, Mejdi Snoussi, Kaïss Aouadi and Adel Kadri
Plants 2020, 9(11), 1534; https://doi.org/10.3390/plants9111534 - 10 Nov 2020
Cited by 75 | Viewed by 5646
Abstract
Piper cubeba L. fruit is an important species used in folk medicine for different types of pains such as rheumatism, chills, flu, colds, muscular aches, and fever. This study examines the chemical constituents, antioxidant activity, and potential inhibitory effect against human peroxiredoxin 5, [...] Read more.
Piper cubeba L. fruit is an important species used in folk medicine for different types of pains such as rheumatism, chills, flu, colds, muscular aches, and fever. This study examines the chemical constituents, antioxidant activity, and potential inhibitory effect against human peroxiredoxin 5, a key enzyme of P. cubeba essential oil from fruits. Using gas chromatography coupled with mass spectrometry (GC–MS), the principal components were methyleugenol (41.31%) and eugenol (33.95%), followed by (E)-caryophyllene (5.65%), p-cymene-8-ol (3.50%), 1,8-cineole (2.94%), and α-terpinolene (1.41%). Results showed similar scavenging activity via 2,2-diphenyl-1-picrylhydrazyl DPPH radical scavenging activity (IC50 = 110.00 ± 0.08 μg/mL), as well as very potent antioxidant activity against both ferric reducing/antioxidant power (FRAP) (106.00 ± 0.11 μg/mL) and β-carotene bleaching (IC50 = 315.00 ± 2.08 μg/mL) assays when compared to positive butylated hydroxytoluene and ascorbic acid. The molecular docking approach has also been performed to screen the antioxidant activities of the major and potent compounds against human protein target peroxiredoxin 5. Results showed good binding profiles and attributed the strongest inhibitory activity to β-caryophyllene oxide (–5.8 kcal/mol), followed respectively by isocembrol and α-selinene (–5.4 kcal/mol), and viridiflorol (–5.1 kcal/mol). Furthermore, ADME (absorption, distribution, metabolism and excretion)-related physicochemical and pharmacokinetic properties have been assessed and support our in vitro findings. This work demonstrates the powerful antioxidant potency of cubeba pepper and paves the way for the discovery and development of antioxidant agent with high potency. Full article
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17 pages, 747 KiB  
Article
Bio-Guided Fractionation Driven by In Vitro α-Amylase Inhibition Assays of Essential Oils Bearing Specialized Metabolites with Potential Hypoglycemic Activity
by Francesca Capetti, Cecilia Cagliero, Arianna Marengo, Carlo Bicchi, Patrizia Rubiolo and Barbara Sgorbini
Plants 2020, 9(9), 1242; https://doi.org/10.3390/plants9091242 - 21 Sep 2020
Cited by 30 | Viewed by 4526
Abstract
Type 2 diabetes mellitus (T2DM) is a metabolic disorder characterized by unpaired blood glycaemia maintenance. T2DM can be treated by inhibiting carbohydrate hydrolyzing enzymes (α-amylases and α-glucosidases) to decrease postprandial hyperglycemia. Acarbose and voglibose are inhibitors used in clinical practice. However, these drugs [...] Read more.
Type 2 diabetes mellitus (T2DM) is a metabolic disorder characterized by unpaired blood glycaemia maintenance. T2DM can be treated by inhibiting carbohydrate hydrolyzing enzymes (α-amylases and α-glucosidases) to decrease postprandial hyperglycemia. Acarbose and voglibose are inhibitors used in clinical practice. However, these drugs are associated with unpleasant gastrointestinal side effects. This study explores new α-amylase inhibitors deriving from plant volatile specialized metabolites. Sixty-two essential oils (EOs) from different plant species and botanical families were subjected to α-amylase in vitro enzymatic assay and chemically characterized using gas chromatography coupled to mass spectrometry. Several EOs were found to be potential α-amylase inhibitors, and Eucalyptus radiata, Laurus nobilis, and Myristicafragrans EOs displayed inhibitory capacities comparable to that of the positive control (i.e., acarbose). A bio-guided fractionation approach was adopted to isolate and identify the active fractions/compounds of Eucalyptus radiata and Myristica fragrans EOs. The bio-guided fractionation revealed that EOs α-amylase inhibitory activity is often the result of antagonist, additive, or synergistic interactions among their bioactive constituents and led to the identification of 1,8-cineole, 4-terpineol, α-terpineol, α-pinene, and β-pinene as bioactive compounds, also confirmed when they were tested singularly. These results demonstrate that EO oils are a promising source of potential α-amylase inhibitors. Full article
(This article belongs to the Special Issue Plant Volatiles: A Goldmine Not Fully Explored)
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16 pages, 1255 KiB  
Article
Effects of Water Stress and Modern Biostimulants on Growth and Quality Characteristics of Mint
by Hosam O. Elansary, Eman A. Mahmoud, Diaa O. El-Ansary and Mohamed A. Mattar
Agronomy 2020, 10(1), 6; https://doi.org/10.3390/agronomy10010006 - 18 Dec 2019
Cited by 44 | Viewed by 7227
Abstract
Natural biostimulants combine different elicitors that may influence economic properties of herbal crops, such as mint. Mint (Mentha longifolia L.) plants were subjected to three water levels based on container substrate capacity (CSC; 100% CSC, 70% CSC, and 50% CSC) and/or applications [...] Read more.
Natural biostimulants combine different elicitors that may influence economic properties of herbal crops, such as mint. Mint (Mentha longifolia L.) plants were subjected to three water levels based on container substrate capacity (CSC; 100% CSC, 70% CSC, and 50% CSC) and/or applications of four biostimulants (CRADLE™, Mobilizer™, Nanozim De’Lite™ [ND], and Nanozim NXT™ [NN]). ND and NN exhibited higher vegetative growth and root dry weight than the control (without biostimulants) and other treatments. NN produced the highest fresh and dry mint yields under all water levels. Irrigation water-use efficiency (IWUE) of NN was highest (2.78 kg m−3) with 70% CSC, whereas the control produced the lowest IWUE (1.85 kg m−3) with 100% CSC. Biostimulants boosted physiological and metabolic responses, including gas exchange, leaf water potential, relative water content, and proline accumulation of stressed plants. NN treatment with 70% CSC had the highest essential oil (EO) ratio (3.35%). Under 70% and 50% CSC with NN treatment, the proportion of 1,8-cineol increased and that of pulegone decreased in EOs. Increased antioxidant activities, reduced H2O2 levels, and increased catalase and superoxide dismutase activities were observed. Applications of ND and NN during water stress conditions increased economic and medicinal properties of mint EOs with applications in the agricultural and pharmaceutical industries. Full article
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15 pages, 4375 KiB  
Article
GC-MS and HS-SPME-GC×GC-TOFMS Determination of the Volatile Composition of Essential Oils and Hydrosols (By-Products) from Four Eucalyptus Species Cultivated in Tuscany
by Francesca Ieri, Lorenzo Cecchi, Elena Giannini, Clarissa Clemente and Annalisa Romani
Molecules 2019, 24(2), 226; https://doi.org/10.3390/molecules24020226 - 9 Jan 2019
Cited by 28 | Viewed by 7560
Abstract
Essential oils are widely used as functional ingredients for potential multi-purpose functional uses. Hydrosols, co-products of the distillation of plant material, are used in food and cosmetic industries and in biological agriculture, but their volatile composition is poorly investigated. The volatile fractions of [...] Read more.
Essential oils are widely used as functional ingredients for potential multi-purpose functional uses. Hydrosols, co-products of the distillation of plant material, are used in food and cosmetic industries and in biological agriculture, but their volatile composition is poorly investigated. The volatile fractions of essential oils and hydrosols from four less-studied 1,8-cineol-rich Eucalyptus species (E. parvula L.A.S. Johnson & K.D. Hill, E. cinerea F. Muell, E. pulverulenta Sims and E. pulverulenta baby blue Sims), cultivated in Tuscany in a system of organic farming, were characterized by solvent dilution (essential oils) or extraction (hydrosols) followed by GC-MS and by HS-SPME-GC×GC-TOFMS analysis. GC-MS analysis showed that essential oils were mainly constituted by oxygenated monoterpenes, particularly 1,8-cineole, with monoterpenes hydrocarbons up to 10.8%. Relative differences in the abundance of minor terpenes as limonene, α-pinene, γ-terpinene, p-cymene, terpinen-4-ol, α-terpineol, and alloaromandrene were pointed out and seem to be suitable for differentiation among EOs of the four different Eucalyptus species. Hydrosols of these species were characterized for the first time: they were mainly constituted by oxygenated monoterpenes (97.6–98.9%), with 1,8-cineole up to 1.6 g/L, while monoterpene and sesquiterpene hydrocarbons were detected only in traces. HS-SPME-GC×GC-TOFMS analysis also allowed providing metabolic profiling of hydrosols for the direct comparison and visualization of volatile components, pointing out the potentially different uses of these products as functional ingredients in food, beverage, and cosmetic industries. Full article
(This article belongs to the Special Issue Solid-Phase Microextraction)
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