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Keywords = deterpenation

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23 pages, 3063 KB  
Article
Lavandula austroapennina (Lamiaceae): Getting Insights into Bioactive Polyphenols of a Rare Italian Endemic Vascular Plant
by Claudia Gravina, Marialuisa Formato, Simona Piccolella, Marika Fiorentino, Adriano Stinca, Severina Pacifico and Assunta Esposito
Int. J. Mol. Sci. 2023, 24(9), 8038; https://doi.org/10.3390/ijms24098038 - 28 Apr 2023
Cited by 15 | Viewed by 2615
Abstract
Lavandula austroapennina N.G. Passal., Tundis and Upon has recently been described as a new species endemic to the southern Apennines (Italy). Locally, this species has a long ethnobotanical tradition of use for curative and decoration purposes and has been the protagonist of a [...] Read more.
Lavandula austroapennina N.G. Passal., Tundis and Upon has recently been described as a new species endemic to the southern Apennines (Italy). Locally, this species has a long ethnobotanical tradition of use for curative and decoration purposes and has been the protagonist of a flourishing essential oil production chain. Currently, while this tradition has long since ended, attention to the species is necessary, with a view to enhancing marginal and rural areas, as a recovery of a precious resource to (i) get insights into its (poly)phenolic fraction and (ii) address new and innovative uses of all its organs in various application fields (e.g., cosmeceutical sector). Therefore, after field sampling and dissection of its organs (i.e., corolla, calyx, leaf, stem and root), the latter, previously deterpenated and defatted, were subjected to accelerated ultrasound extraction and the related alcoholic extracts were obtained. Chemical composition, explored by UHPLC-QqTOF-MS/MS, and the following multivariate data analysis showed that the hydroxycinnamoyl derivatives are abundant in the leaf, stem and root, while flavonoids are more present in corolla and calyx. In particular, coumaroyl flavonoids with glyconic portion containing also hexuronyl moieties differentiated corolla organ, while yunnaneic acid D isomers and esculin distinguished root. When antiradical and reducing properties were evaluated (by means of ABTS, DPPH and PFRAP tests), a similar clustering of organs was achieved and the marked antioxidant efficacy of leaf, stem and root extracts was found. Thus, following cytotoxicity screening by MTT test on HaCaT keratinocytes, the protective effects of the organ extracts were assessed by wound closure observed after the scratch test. In addition, the extracts from corolla, leaf and stem were particularly active at low doses inducing rapid wound closure on HaCaT cells at a concentration of 1 μg/mL. The diversity in (poly)phenols of each organ and the promising bioactivity preliminarily assessed suggest further investigation to be carried out to fully recover and valorize this precious endemic vascular plant. Full article
(This article belongs to the Special Issue Polyphenols and Their Impact on Human Health)
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14 pages, 2208 KB  
Article
Separation of D-Limonene and Other Oxygenated Compounds from Orange Essential Oil by Molecular Distillation and Fractional Distillation with a Wiped Film Evaporator
by Jorge Alberto García-Fajardo, David Antonio Flores-Méndez, Ángela Suárez-Jacobo, Lilia Guadalupe Torres-Martínez, Miriam Granados-Vallejo, Rosa Isela Corona-González, Guadalupe María Guatemala-Morales and Enrique Arriola-Guevara
Processes 2023, 11(4), 991; https://doi.org/10.3390/pr11040991 - 24 Mar 2023
Cited by 15 | Viewed by 7796
Abstract
Orange essential oil (OEO) is mainly composed of D-Limonene and other oxygenated compounds that contribute to the orange flavor and aroma. However, D-Limonene is unstable in the presence of heat, light, and water, affecting the quality of the OEO. Therefore, the objective of [...] Read more.
Orange essential oil (OEO) is mainly composed of D-Limonene and other oxygenated compounds that contribute to the orange flavor and aroma. However, D-Limonene is unstable in the presence of heat, light, and water, affecting the quality of the OEO. Therefore, the objective of this study was to fractionate OEO by distillation, both molecular and fractionated (hybrid), producing a D-Limonene-rich fraction. The OEO was characterized by physicochemical tests and gas chromatography combined with mass spectrometry (GC–MS). The fractionation of the OEO was carried out by molecular distillation and fractional distillation following, in both cases, a factorial design (23) with central points, considering the D-Limonene percentage in the distillate and the residue as a response variable. According to the physicochemical characterization, the predominant optical isomer was dextrorotatory, where D-Limonene is the main component of OEO (92.584%). For molecular distillation, the D-Limonene content was reduced to 47.964% in the residue or deterpenated fraction, while for fractional distillation, it was 86.779%. For this study, molecular distillation was considered a non-thermal process (use of low temperatures) that promoted the efficient recovery of oxygenated compounds. In contrast, fractional distillation favored the recovery of D-Limonene in the light fraction. Full article
(This article belongs to the Section Separation Processes)
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14 pages, 3898 KB  
Article
The Role of the Anion in Imidazolium-Based Ionic Liquids for Fuel and Terpenes Processing
by Aline Zambom, Sérgio M. Vilas-Boas, Liliana P. Silva, Mónia A. R. Martins, Olga Ferreira and Simão P. Pinho
Molecules 2023, 28(6), 2456; https://doi.org/10.3390/molecules28062456 - 7 Mar 2023
Cited by 6 | Viewed by 2605
Abstract
The potentialities of methylimidazolium-based ionic liquids (ILs) as solvents were evaluated for some relevant separation problems—terpene fractionation and fuel processing—studying selectivities, capacities, and solvent performance indices. The activity coefficients at infinite dilution of the solute (1) in the IL (3), γ13 [...] Read more.
The potentialities of methylimidazolium-based ionic liquids (ILs) as solvents were evaluated for some relevant separation problems—terpene fractionation and fuel processing—studying selectivities, capacities, and solvent performance indices. The activity coefficients at infinite dilution of the solute (1) in the IL (3), γ13, of 52 organic solutes were measured by inverse gas chromatography over a temperature range of 333.2–453.2 K. The selected ILs are 1-butyl-3-methylimidazolium hexafluorophosphate, [C4mim][PF6], and the equimolar mixture of [C4mim][PF6] and 1-butyl-3-methylimidazolium chloride, [C4mim]Cl. Generally, low polar solutes follow γ1,C4mimCl > γ1,C4mimPF6+C4mimCl > γ1,C4mimPF6 while the opposite behavior is observed for alcohols and water. For citrus essential oil deterpenation, the results suggest that cations with long alkyl chains, such as C12mim+, promote capacity, while selectivity depends on the solute polarity. Promising results were obtained for the separation of several model mixtures relevant to fuel industries using the equimolar mixture of [C4mim][PF6] and [C4mim]Cl. This work demonstrates the importance of tailoring the polarity of the solvents, suggesting the use of ILs with mixed anions as alternative solvents for the removal of aliphatic hydrocarbons and contaminants from fuels. Full article
(This article belongs to the Special Issue Properties and Applications of Ionic Liquids-Based Advanced Materials)
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11 pages, 2014 KB  
Article
Translational Value of the Transdermal Administration of Bergamot Essential Oil and of Its Fractions
by Damiana Scuteri, Laura Rombolà, Michele Crudo, Chizuko Watanabe, Hirokazu Mizoguchi, Shinobu Sakurada, Kengo Hamamura, Tsukasa Sakurada, Luigi Antonio Morrone, Paolo Tonin, Giacinto Bagetta and Maria Tiziana Corasaniti
Pharmaceutics 2022, 14(5), 1006; https://doi.org/10.3390/pharmaceutics14051006 - 7 May 2022
Cited by 18 | Viewed by 2995
Abstract
The essential oil of bergamot (BEO) has consistently proven antinociceptive and antiallodynic properties. Accordingly, the analgesic efficacy of the decolored essential oil (DEC), with higher levels of limonene, and the deterpenated (DET) fraction, with higher levels of linalool and linalyl acetate, was investigated [...] Read more.
The essential oil of bergamot (BEO) has consistently proven antinociceptive and antiallodynic properties. Accordingly, the analgesic efficacy of the decolored essential oil (DEC), with higher levels of limonene, and the deterpenated (DET) fraction, with higher levels of linalool and linalyl acetate, was investigated using a formalin test after inhalation. The present study was aimed at characterizing the effects of BEO, its components with the highest pharmacological activity (represented by linalool, limonene, and linalyl acetate), and its DEC and DET fractions on the formalin test after transdermal administration relevant to clinical translation through topical application. To this aim, the schedule of intervention involved administration immediately after formalin injection or as a 5 min pretreatment followed by washout in ddY-strain mice. This study demonstrates, for the first time, the significant analgesic effect of all three constituents in the first and second phases, accounting for the efficacy of the essential oil in the formalin test. While all fractions revealed equal activity toward the phytocomplex in the early phase, the reduction in time of licking/biting during the late phase was more markedly induced by DEC. Moreover, pretreatment with BEO and its fractions followed by washout did not produce a significant reduction in licking/biting time in both phases of formalin-induced nociceptive response. Full article
(This article belongs to the Special Issue Pharmaceutical Applications of Plant Extracts)
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32 pages, 4928 KB  
Article
A Comprehensive Phytochemical Analysis of Terpenes, Polyphenols and Cannabinoids, and Micromorphological Characterization of 9 Commercial Varieties of Cannabis sativa L.
by Eugenia Mazzara, Jacopo Torresi, Gelsomina Fico, Alessio Papini, Nicola Kulbaka, Stefano Dall’Acqua, Stefania Sut, Stefania Garzoli, Ahmed M. Mustafa, Loredana Cappellacci, Dennis Fiorini, Filippo Maggi, Claudia Giuliani and Riccardo Petrelli
Plants 2022, 11(7), 891; https://doi.org/10.3390/plants11070891 - 27 Mar 2022
Cited by 40 | Viewed by 10173
Abstract
New hemp (Cannabis sativa L.) strains developed by crossbreeding selected varieties represent a novel research topic worthy of attention and investigation. This study focused on the phytochemical characterization of nine hemp commercial cultivars. Hydrodistillation was performed in order to collect the essential [...] Read more.
New hemp (Cannabis sativa L.) strains developed by crossbreeding selected varieties represent a novel research topic worthy of attention and investigation. This study focused on the phytochemical characterization of nine hemp commercial cultivars. Hydrodistillation was performed in order to collect the essential oils (EO), and also the residual water and deterpenated biomass. The volatile fraction was analyzed by GC-FID, GC-MS, and SPME-GC-MS, revealing three main chemotypes. The polyphenolic profile was studied in the residual water and deterpenated biomass by spectrophotometric assays, and HPLC-DAD-MSn and 1H-NMR analyses. The latter were employed for quali–quantitative determination of cannabinoids in the deterpenated material in comparison with the one not subjected to hydrodistillation. In addition, the glandular and non-glandular indumentum of the nine commercial varieties was studied by means of light microscopy and scanning electron microscopy in the attempt to find a possible correlation with the phytochemical and morphological traits. The EO and residual water were found to be rich in monoterpene and sesquiterpene hydrocarbons, and flavonol glycosides, respectively, while the deterpenated material was found to be a source of neutral cannabinoids. The micromorphological survey allowed us to partly associate the phytochemistry of these varieties with the hair morphotypes. This research sheds light on the valorization of different products from the hydrodistillation of hemp varieties, namely, essential oil, residual water, and deterpenated biomass, which proved to be worthy of exploitation in industrial and health applications. Full article
(This article belongs to the Special Issue 10th Anniversary of Plants—Recent Advances and Perspectives)
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10 pages, 3153 KB  
Article
Preclinical Characterization of Antinociceptive Effect of Bergamot Essential Oil and of Its Fractions for Rational Translation in Complementary Therapy
by Damiana Scuteri, Laura Rombolà, Michele Crudo, Chizuko Watanabe, Hirokazu Mizoguchi, Shinobu Sakurada, Kengo Hamamura, Tsukasa Sakurada, Paolo Tonin, Maria Tiziana Corasaniti and Giacinto Bagetta
Pharmaceutics 2022, 14(2), 312; https://doi.org/10.3390/pharmaceutics14020312 - 28 Jan 2022
Cited by 25 | Viewed by 3845
Abstract
Bergamot essential oil (BEO) is endowed with consistent and reproducible antinociceptive and anti-allodynic properties when administered via an inhalation route. However, the effects of its main constituents and of its decolored (DEC) and deterpenated (DET) fractions, which are enriched in limonene or in [...] Read more.
Bergamot essential oil (BEO) is endowed with consistent and reproducible antinociceptive and anti-allodynic properties when administered via an inhalation route. However, the effects of its main constituents and of its decolored (DEC) and deterpenated (DET) fractions, which are enriched in limonene or in linalool and linalyl acetate, respectively, on spontaneous motor activity related to anxiety and on formalin-induced licking/biting biphasic behavior have never been investigated before. Therefore, the present research aims to characterize the role of BEO components on an experimental pain model that is relevant to clinical translation. Under our present experimental conditions, a paper filter disc soaked with different volumes of the phytocomplex and of its fractions that was applied at the edge of the observation chamber allowed the effects on the spontaneous motor activity and on the formalin-induced nocifensive response in ddY-strain mice to be studied. The present research demonstrated the effects of the DEC fraction of BEO on motor activity and on formalin-induced licking/biting behavior for the first time, proving that limonene is implicated in reduced motor activity and that it is important for the analgesic effect. Full article
(This article belongs to the Special Issue Essential Oils in Pharmaceutical Products)
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17 pages, 20458 KB  
Article
Effect of Deterpenated Origanum majorana L. Essential Oil on the Physicochemical and Biological Properties of Chitosan/β-Chitin Nanofibers Nanocomposite Films
by Rut Fernández-Marín, Muhammad Mujtaba, Demet Cansaran-Duman, Ghada Ben Salha, Mª Ángeles Andrés Sánchez, Jalel Labidi and Susana C. M. Fernandes
Polymers 2021, 13(9), 1507; https://doi.org/10.3390/polym13091507 - 7 May 2021
Cited by 13 | Viewed by 5097
Abstract
Herein, the effect of three deterpenated fractions from Origanum majorana L. essential oil on the physicochemical, mechanical and biological properties of chitosan/β-chitin nanofibers-based nanocomposite films were investigated. In general, the incorporation of Origanum majorana L. original essential oil or its deterpenated fractions increases [...] Read more.
Herein, the effect of three deterpenated fractions from Origanum majorana L. essential oil on the physicochemical, mechanical and biological properties of chitosan/β-chitin nanofibers-based nanocomposite films were investigated. In general, the incorporation of Origanum majorana L. original essential oil or its deterpenated fractions increases the opacity of the nanocomposite films and gives them a yellowish color. The water solubility decreases from 58% for chitosan/β-chitin nanofibers nanocomposite film to around 32% for the nanocomposite films modified with original essential oil or its deterpenated fractions. Regarding the thermal stability, no major changes were observed, and the mechanical properties decreased. Interestingly, data show differences on the biological properties of the materials depending on the incorporated deterpenated fraction of Origanum majorana L. essential oil. The nanocomposite films prepared with the deterpenated fractions with a high concentration of oxygenated terpene derivatives show the best antifungal activity against Aspergillus niger, with fungal growth inhibition of around 85.90%. Nonetheless, the only nanocomposite film that does not present cytotoxicity on the viability of L929 fibroblast cells after 48 and 72 h is the one prepared with the fraction presenting the higher terpenic hydrocarbon content (87.92%). These results suggest that the composition of the deterpenated fraction plays an important role in determining the biological properties of the nanocomposite films. Full article
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