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13 pages, 1076 KiB

Open AccessArticle

Chemical Composition, Antioxidant Properties, and Antibacterial Activity of Essential Oils of Satureja macrostema (Moc. and Sessé ex Benth.) Briq

by Lucia Barrientos Ramírez, José Antonio Silva Guzmán, Edison Antonio Osorio Muñoz, Carlos Alvarez Moya, Mónica Reynoso Silva, Abraham Francisco Cetina Corona, Josefina Casas Solis and J. Jesús Vargas Radillo

Molecules 2023, 28(12), 4719; https://doi.org/10.3390/molecules28124719 - 12 Jun 2023

Cited by 1 | Viewed by 1582

Abstract

Satureja macrostema is a plant that is located in various regions of Mexico and is used in a traditional way against illness. Essential oils (EOs) were obtained from leaves Satureja macrostema and the chemical composition was evaluated by gas chromatography–mass spectrometry (GC-MS). The [...] Read more.

Satureja macrostema is a plant that is located in various regions of Mexico and is used in a traditional way against illness. Essential oils (EOs) were obtained from leaves Satureja macrostema and the chemical composition was evaluated by gas chromatography–mass spectrometry (GC-MS). The antioxidant effect of the oil was assayed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and by Trolox Equivalent Antioxidant Capacity (TEAC). In vitro antibacterial activity against Escherichia coli and Staphylococcus aureus was determined using a broth microdilution assay and thin layer chromatography–direct bioautography (TLC-DB) to identify active antibacterial compounds. The EOs analysis showed 21 compounds, 99% terpenes, and 96% oxygenated monoterpenes, with trans-piperitone epoxide (46%), cis-piperitone epoxide (22%), and piperitenone oxide (11%) as more abundant compounds. Likewise, S. macrostema EOs showed an antioxidant activity of DPPH = 82%, with 50% free radical scavenging (IC₅₀) = 7 mg/mL and TEAC = 0.005, an antibacterial effect against E. coli of 73% inhibition, and 81% over S. aureus at dose of 100 µL of undiluted crude oil. The TLC-DB assay showed that the most active compounds were derived from piperitone. The comparison with other studies on S. macrostema shows variability in the compounds and their abundances, which can be attributed to climatic factors and the maturity of plants with similar antioxidant and antibacterial activities. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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19 pages, 4373 KiB

Open AccessArticle

Selective Photooxidation of Valencene and Thymol with Nano-TiO₂ and O₂ as Oxidant

by Henry Martínez, Jane Neira, Álvaro A. Amaya, Edgar A. Páez-Mozo and Fernando Martínez Ortega

Molecules 2023, 28(9), 3868; https://doi.org/10.3390/molecules28093868 - 04 May 2023

Cited by 1 | Viewed by 1543

Abstract

The selective photocatalytic oxidation with O₂ as oxidant of valencene and thymol was evaluated using nanostructured TiO₂ under UV-Vis radiation at atmospheric conditions. The effect of the morphology and optical properties of TiO₂ nanotubes and aminate nanoparticles was studied. Different [...] Read more.

The selective photocatalytic oxidation with O₂ as oxidant of valencene and thymol was evaluated using nanostructured TiO₂ under UV-Vis radiation at atmospheric conditions. The effect of the morphology and optical properties of TiO₂ nanotubes and aminate nanoparticles was studied. Different scavengers were used to detect the presence of positive holes (h⁺), electrons (e⁻), hydroxyl radicals (•OH), and the superoxide radical anion (O₂⁻) during the photooxidation reaction. Superoxide anion radical is the main oxidizing specie formed, which is responsible for the selective formation of nootkatone and thymoquinone using aminated TiO₂ nanoparticles under 400 nm radiation. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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17 pages, 758 KiB

Open AccessArticle

Chemical Characterization and Determination of the Antioxidant Properties of Phenolic Compounds in Three Scutellaria sp. Plants Grown in Colombia

by Silvia M. Porras, Rogerio A. Saavedra, Lady J. Sierra, Robert T. González, Jairo R. Martínez and Elena E. Stashenko

Molecules 2023, 28(8), 3474; https://doi.org/10.3390/molecules28083474 - 14 Apr 2023

Viewed by 1423

Abstract

Plants of the genus Scutellaria (Lamiaceae) have a wide variety of bioactive secondary metabolites with diverse biological properties, e.g., anti-inflammatory, antiallergenic, antioxidant, antiviral, and antitumor activities. The chemical composition of the hydroethanolic extracts, obtained from dried plants of S. incarnata, S [...] Read more.

Plants of the genus Scutellaria (Lamiaceae) have a wide variety of bioactive secondary metabolites with diverse biological properties, e.g., anti-inflammatory, antiallergenic, antioxidant, antiviral, and antitumor activities. The chemical composition of the hydroethanolic extracts, obtained from dried plants of S. incarnata, S. coccinea, and S. ventenatii × S. incarnata, was determined by UHPLC/ESI-Q-Orbitrap-MS. The flavones were found in a higher proportion. Baicalin and dihydrobaicalein-glucuronide were the major extract components in S. incarnata (287.127 ± 0.005 mg/g and 140.18 ± 0.07 mg/g), in S. coccinea (158.3 ± 0.34 mg/g and 51.20 ± 0.02 mg/g), and in S. ventenatii × S. incarnata (186.87 ± 0.01 mg/g and 44.89 ± 0.06 mg/g). The S. coccinea extract showed the highest antioxidant activity in the four complementary techniques employed to evaluate all extracts: ORAC (3828 ± 3.0 µmol Trolox^®/g extract), ABTS^+• (747 ± 1.8 µmol Trolox^®/g extract), online HPLC-ABTS^+• (910 ± 1.3 µmol Trolox^®/g extract), and β-carotene (74.3 ± 0.8 µmol Trolox^®/g extract). Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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14 pages, 2524 KiB

Open AccessArticle

Echinophora tenuifolia subsp. sibthorpiana—Study of the Histochemical Localization of Essential Oil

by Stanislava Ivanova, Stanislav Dyankov, Diana Karcheva-Bahchevanska, Velislava Todorova, Yoana Georgieva, Niko Benbassat and Kalin Ivanov

Molecules 2023, 28(7), 2918; https://doi.org/10.3390/molecules28072918 - 24 Mar 2023

Viewed by 1379

Abstract

Background: Echinophora tenuifolia L. subsp. sibthorpiana is a perennial, aromatic plant used in traditional folk medicine and cuisine of the Mediterranean and the Middle East. However, scholars have not fully studied the pharmacological potential of the herb, and the scientific data on this [...] Read more.

Background: Echinophora tenuifolia L. subsp. sibthorpiana is a perennial, aromatic plant used in traditional folk medicine and cuisine of the Mediterranean and the Middle East. However, scholars have not fully studied the pharmacological potential of the herb, and the scientific data on this plant species are limited. This study aimed to evaluate the chemical composition of the essential oil (EO) obtained from the aerial parts of E. tenuifolia subsp. sibthorpiana growing wild in Bulgaria and to perform histochemical analysis. Methods: A microscopic histochemical analysis and gas chromatography with mass spectrometry were performed. Results: The histochemical analysis confirmed the presence of terpenes in the stem and leaf of E. tenuifolia subsp. sibthorpiana. The phenylpropanoid methyleugenol was identified as the main compound in the EO, representing 48.13% of the total oil composition. There were also found considerable amounts of monoterpene hydrocarbons, representing 41.68% of the total EO. Alpha-phellandrene, o-cymene, and β-phellandrene were the most abundant monoterpene hydrocarbons. Conclusion: This is the first histochemical analysis performed on E. tenuifolia subsp. sibthorpiana. This is the first report of the EO composition from Bulgarian E. tenuifolia subsp. sibthorpiana, and our results indicate some future possibilities for evaluating of the biological activity of the EO of E. tenuifolia subsp. sibthorpiana and highlight the potential future use of the EO of this plant species. E. tenuifolia L. subsp. sibthorpiana EO possesses a good potential for use as a biopesticide and repellent an environmentally friendly alternative of synthetic pesticides. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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14 pages, 2496 KiB

Open AccessArticle

Essential Oils Distilled from Colombian Aromatic Plants and Their Constituents as Penetration Enhancers for Transdermal Drug Delivery

by Heider Carreño, Elena E. Stashenko and Patricia Escobar

Molecules 2023, 28(6), 2872; https://doi.org/10.3390/molecules28062872 - 22 Mar 2023

Cited by 3 | Viewed by 1412

Abstract

The study aimed to determine the enhanced effects of essential oils (EOs) and plant-derived molecules (PDMs) as penetration enhancers (PEs) for transdermal drug delivery (TDD) of caffeine. A 1% w/w solution of eight EOs and seven PDMs was included in the [...] Read more.

The study aimed to determine the enhanced effects of essential oils (EOs) and plant-derived molecules (PDMs) as penetration enhancers (PEs) for transdermal drug delivery (TDD) of caffeine. A 1% w/w solution of eight EOs and seven PDMs was included in the 1% caffeine carbopol hydrogel. Franz diffusion cell experiments were performed using mice with full-thickness skin. At various times over 24 h, 300 μL of the receptor were withdrawn and replaced with fresh medium. Caffeine was analyzed spectrophotometrically at 272 nm. The skin irritation effects of the hydrogels applied once a day for 21 days were investigated in mice. The steady-state flux (J_SS) of the caffeine hydrogel was 30 ± 19.6 µg cm⁻² h⁻¹. An increase in caffeine J_SS was induced by Lippia origanoides > Turnera diffusa > eugenol > carvacrol > limonene, with values of 150 ± 14.1, 130 ± 47.6, 101 ± 21.7, 90 ± 18.4, and 86 ± 21.0 µg cm⁻² h⁻¹, respectively. The Kp of caffeine was 2.8 ± 0.26 cm h⁻¹, almost 2–4 times lower than that induced by Lippia origanoides > Turnera diffusa > limonene > eugenol > carvacrol, with Kp values of 11 ± 1.7, 8.8 ± 4.2, 6.8 ± 1.7, 6.3 ± 1.2, and 5.15 ± 1.0 cm h⁻¹, respectively. No irritating effects were observed. Lippia origanoides, Turnera diffusa, eugenol, carvacrol, and limonene improved caffeine’s skin permeation. These compounds may be as effective as the PE in TDD systems. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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13 pages, 762 KiB

Open AccessArticle

Volatile Metabolites of Piper eriopodon (Miq.) C.DC. from Northern Region of Colombia and Assessment of In Vitro Bioactivities of the Leaf Essential Oil

by Amner Muñoz-Acevedo, María C. González, Yurina Sh. De Moya and Juan D. Rodríguez

Molecules 2023, 28(6), 2594; https://doi.org/10.3390/molecules28062594 - 13 Mar 2023

Cited by 1 | Viewed by 1310

Abstract

Piper eriopodon is one of the Piper species found in the Sierra Nevada de Santa Marta, and the species has been reported with different compositions of their essential oils (EO). In this study, the volatile fractions/essential oil (by HS-SPME/SDE/MWHD-GC–MS/¹H-NMR) of different [...] Read more.

Piper eriopodon is one of the Piper species found in the Sierra Nevada de Santa Marta, and the species has been reported with different compositions of their essential oils (EO). In this study, the volatile fractions/essential oil (by HS-SPME/SDE/MWHD-GC–MS/¹H-NMR) of different parts from the plant were characterized, and assessments of the in vitro bio-properties of the leaf EO were conducted. The results indicated the following: (i) in the volatile fractions were β-caryophyllene (~23%)/myrcene (~20%) (inflorescences) and β-caryophyllene (~43%)/β-selinene (~20%) (leaves) using HS-SPME; myrcene (~31%)/β-pinene (~23%) (inflorescences), gibbilimbol B (~60%) (fruits) and gibbilimbol B (~46%)/β-caryophyllene (~11%) (leaves) through SDE; (ii) leaf EO contained gibbilimbol B (~72%), confirmed with ¹H-NMR; (iii) the cytotoxic values (µg/mL) in erythrocytes/lymphocytes/Hep-2 were HC₅₀: 115 ± 3 (eryth.), LC₅₀: 71 ± 4 (lymph.) and LC₅₀: 33 ± 2 (cell-line); (iv) the antibacterial susceptibilities (ϕ inh. zone, mm; 4–16 µg EO) were 22.5 ± 0.4–97 ± 4 (Staphylococcus aureus), 23 ± 2–77 ± 4 (Escherichia coli) and 17 ± 1–48 ± 3 (Listeria monocytogenes); (v) the TAA value was 2249 ± 130 mmol Trolox^®/kg; (vi) the IC₅₀ value was 13±1 µg/mL (AChE) with 20 ± 0–37 ± 6% repellency (2–4 h, Sitophilus zeamais). Thus, the EO of P. eriopodon leaves from northern Colombia could be a promising species for sustainable exploitation in the future due to its outstanding bioactivities. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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18 pages, 6909 KiB

Open AccessArticle

Color, Antioxidant Capacity and Flavonoid Composition in Hibiscus rosa-sinensis Cultivars

by Jesica J. Mejía, Lady J. Sierra, José G. Ceballos, Jairo R. Martínez and Elena E. Stashenko

Molecules 2023, 28(4), 1779; https://doi.org/10.3390/molecules28041779 - 13 Feb 2023

Cited by 5 | Viewed by 4712

Abstract

Hibiscus rosa-sinensis plants are mainly cultivated as ornamental plants, but they also have food and medicinal uses. In this work, 16 H. rosa-sinensis cultivars were studied to measure their colorimetric parameters and the chemical composition of hydroethanolic extracts obtained from their petals. These [...] Read more.

Hibiscus rosa-sinensis plants are mainly cultivated as ornamental plants, but they also have food and medicinal uses. In this work, 16 H. rosa-sinensis cultivars were studied to measure their colorimetric parameters and the chemical composition of hydroethanolic extracts obtained from their petals. These extracts were characterized using UHPLC-ESI⁺-Obitrap-MS, and their antioxidant activity was evaluated using the ORAC assay. The identified flavonoids included anthocyanins derived from cyanidin, glycosylated flavonols derived from quercetin and kaempferol, and flavan-3-ols such as catechin and epicatechin. Cyanidin-sophoroside was the anthocyanin present in extracts of lilac, pink, orange, and red flowers, but was not detected in extracts of white or yellow flowers. The total flavonol concentration in the flower extracts was inversely proportional to the total anthocyanin content. The flavonol concentration varied according to the cultivar in the following order: red < pink < orange < yellow ≈ white, with the extract from the red flower presenting the lowest flavonol concentration and the highest anthocyanin concentration. The antioxidant activity increased in proportion to the anthocyanin concentration, from 1580 µmol Trolox^®/g sample (white cultivar) to 3840 µmol Trolox^®/g sample (red cultivar). Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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22 pages, 6943 KiB

Open AccessArticle

Essential Oils from Colombian Plants: Antiviral Potential against Dengue Virus Based on Chemical Composition, In Vitro and In Silico Analyses

by Lina Silva-Trujillo, Elizabeth Quintero-Rueda, Elena E. Stashenko, Sergio Conde-Ocazionez, Paola Rondón-Villarreal and Raquel E. Ocazionez

Molecules 2022, 27(20), 6844; https://doi.org/10.3390/molecules27206844 - 12 Oct 2022

Cited by 5 | Viewed by 2331

Abstract

Currently, there are no therapies to prevent severe dengue disease. Essential oils (EOs) can serve as primary sources for research and the discovery of phytomedicines for alternative therapy. Fourteen EOs samples were obtained by distillation from six plants used in Colombian folk medicine. [...] Read more.

Currently, there are no therapies to prevent severe dengue disease. Essential oils (EOs) can serve as primary sources for research and the discovery of phytomedicines for alternative therapy. Fourteen EOs samples were obtained by distillation from six plants used in Colombian folk medicine. GC/MS analysis identified 125 terpenes. Cytopathic effect (CPE) reduction assays revealed differences in antiviral activity. EOs of Lippia alba, citral chemotype and carvone-rich fraction; Lippia origanoides, phellandrene chemotype; and Turnera diffusa, exhibited strong antiviral activity (IC₅₀: 29 to 82 µg/mL; SI: 5.5 to 14.3). EOs of Piper aduncum, Ocimum basilicum, and L. origanoides, carvacrol, and thymol chemotypes, exhibited weak antiviral activity (32 to 53% DENV-CPE reduction at 100 µg/mL; SI > 5.0). Cluster and one-way ANOVA analyses suggest that the strong antiviral activity of EOs could be attributed to increased amounts of non-phenolic oxygenated monoterpenes and sesquiterpene hydrocarbons. Docking analyses (AutoDock Vina) predicted binding affinity between the DENV-2 E protein and terpenes: twenty sesquiterpene hydrocarbons (−8.73 to −6.91 kcal/mol), eight oxygenated monoterpenes (−7.52 to −6.98 kcal/mol), and seven monoterpene hydrocarbons (−7.60 to −6.99 kcal/mol). This study reports for the first time differences in the antiviral activity of EOs against DENV, corresponding to their composition of monoterpenes and sesquiterpenes. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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13 pages, 1389 KiB

Open AccessArticle

In Vitro Activity of Essential Oils Distilled from Colombian Plants against Candidaauris and Other Candida Species with Different Antifungal Susceptibility Profiles

by Carolina Zapata-Zapata, Manuela Loaiza-Oliva, María C. Martínez-Pabón, Elena E. Stashenko and Ana C. Mesa-Arango

Molecules 2022, 27(20), 6837; https://doi.org/10.3390/molecules27206837 - 12 Oct 2022

Cited by 7 | Viewed by 2191

Abstract

Multi-drug resistant species such as Candida auris are a global health threat. This scenario has highlighted the need to search for antifungal alternatives. Essential oils (EOs), or some of their major compounds, could be a source of new antifungal molecules. The aim of [...] Read more.

Multi-drug resistant species such as Candida auris are a global health threat. This scenario has highlighted the need to search for antifungal alternatives. Essential oils (EOs), or some of their major compounds, could be a source of new antifungal molecules. The aim of this study was to evaluate the in vitro activity of EOs and some terpenes against C. auris and other Candida spp. The eleven EOs evaluated were obtained by hydro-distillation from different Colombian plants and the terpenes were purchased. EO chemical compositions were obtained by gas chromatography/mass spectrometry (GC/MS). Antifungal activity was evaluated following the CLSI standard M27, 4th Edition. Cytotoxicity was tested on the HaCaT cell line and fungal growth kinetics were tested by time–kill assays. Candida spp. showed different susceptibility to antifungals and the activity of EOs and terpenes was strain-dependent. The Lippia origanoides (thymol + p-cymene) chemotype EO, thymol, carvacrol, and limonene were the most active, mainly against drug-resistant strains. The most active EOs and terpenes were also slightly cytotoxic on the HaCaT cells. The findings of this study suggest that some EOs and commercial terpenes can be a source for the development of new anti-Candida products and aid the identification of new antifungal targets or action mechanisms. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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11 pages, 317 KiB

Open AccessArticle

Inhibitory Effect of GRAS Essential Oils and Plant Extracts on the Growth of Aspergillus westerdijkiae and Aspergillus carbonarius Strains

by Mariana Paiva Rodrigues, Águida Aparecida de Oliveira, Gabriela Lago Biscoto, Priscila Natália Pinto, Raul Roque de Souza Dias, Lauranne Alves Salvato, Luiz Antonio Moura Keller, Lilia Reneé Cavaglieri, Carlos Alberto da Rocha Rosa and Kelly Moura Keller

Molecules 2022, 27(19), 6422; https://doi.org/10.3390/molecules27196422 - 29 Sep 2022

Cited by 2 | Viewed by 1182

Abstract

The effect of essential oils (obtained using hydrodistillation) and plant extracts (ethanolic, aqueous, and hexanic extractions) of 10 different plants cultivated in Brazil were tested using the diffusion agar method, with the objective of evaluating the inhibitory effect of the oils and extracts [...] Read more.

The effect of essential oils (obtained using hydrodistillation) and plant extracts (ethanolic, aqueous, and hexanic extractions) of 10 different plants cultivated in Brazil were tested using the diffusion agar method, with the objective of evaluating the inhibitory effect of the oils and extracts on the mycelial growth of Aspergillus westerdijkiae NRRL 3174 and A. carbonarius RC 2054 (UNRC). Of the 40 essential oils and plant extracts analyzed, oregano essential oil and plant extract, rosemary essential oil, and the clove ethanolic extract were the best choice to obtain the growth parameters (radial growth rates (mm day⁻¹) and lag phase (h)) due the good results presented and the volume of oil/extract obtained. Comparing all the essential oils and plant extracts that were tested for growth parameters, the best results were obtained for the clove ethanolic extract for both strains assayed. These results demonstrated an outstanding potential use of some of these products in prevention of fungal contamination in food. However, further studies need to be conducted to determine the ability of these oils and extracts to inhibit or reduce ochratoxin A production. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

7 pages, 1592 KiB

Open AccessArticle

Acetone as Artifact of Analysis in Terpene Samples by HS-GC/MS

by Sytze Elzinga, Jorge Dominguez-Alonzo, Raquel Keledjian, Brad Douglass and Jeffrey C. Raber

Molecules 2022, 27(18), 6037; https://doi.org/10.3390/molecules27186037 - 16 Sep 2022

Cited by 1 | Viewed by 2142

Abstract

Cannabis-infused product manufacturers often add terpenes to enhance flavor. Meanwhile, labeling requirements for these same products necessitate testing for residual solvent levels. We have found that heating terpene samples containing an oxygen or air atmosphere results in the detection of significantly higher levels [...] Read more.

Cannabis-infused product manufacturers often add terpenes to enhance flavor. Meanwhile, labeling requirements for these same products necessitate testing for residual solvent levels. We have found that heating terpene samples containing an oxygen or air atmosphere results in the detection of significantly higher levels of acetone when compared to the same compound in argon atmosphere using temperature regimes common to headspace autosampler routines. This formation was statistically significant (p = 0.05) for most of the predominant terpenes found in cannabis. The largest increase in acetone formation was seen for terpinolene which showed an 885% increase in oxygen atmosphere (4603.6 PPM) when compared to analysis under argon (519.9 PPM). Cannabinoids were shown to reduce this formation and explain why high levels of acetone are not reported in cannabis extracts, even though these can contain up to 40% terpenes. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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14 pages, 6759 KiB

Open AccessArticle

Characterization of Bioactive Compounds from Patchouli Extracted via Supercritical Carbon Dioxide (SC-CO₂) Extraction

by Syaifullah Muhammad, Abdul Khalil H. P. S., Shazlina Abd Hamid, Mohammed Danish, M. Marwan, Yunardi Yunardi, C. K. Abdullah, M. Faisal and Esam Bashir Yahya

Molecules 2022, 27(18), 6025; https://doi.org/10.3390/molecules27186025 - 15 Sep 2022

Cited by 11 | Viewed by 2557

Abstract

Patchouli extracts and oils extracted from Pogostemon cablin are essential raw material for the perfume and cosmetics industries, in addition to being used as a natural additive for food flavoring. Steam distillation is a standard method used for plant extraction. However, this method [...] Read more.

Patchouli extracts and oils extracted from Pogostemon cablin are essential raw material for the perfume and cosmetics industries, in addition to being used as a natural additive for food flavoring. Steam distillation is a standard method used for plant extraction. However, this method causes thermal degradation of some essential components of the oil. In this study, patchouli was extracted with supercritical carbon dioxide (SC-CO₂) under different conditions of pressure (10–30 MPa) and temperature (40–80 °C). The chemical components of the crude extracted oil and the functional group were characterized using gas chromatography-mass spectrometry (GC-MS) and Fourier Transform Infrared Spectroscopy (FT-IR). The extraction with supercritical carbon dioxide was shown to provide a higher yield (12.41%) at a pressure of 20 MPa and a temperature of 80 °C. Patchouli alcohol, Azulene, δ-Guaiene, and Seychellene are the main bioactive compounds that GC-MS results have identified. FTIR spectra showed alcohol, aldehyde, and aromatic ring bond stretching peaks. Extraction of patchouli with supercritical carbon dioxide provided a higher yield and a better quality of the crude patchouli oil. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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17 pages, 2143 KiB

Open AccessArticle

Flower Extracts from Ornamental Plants as Sources of Sunscreen Ingredients: Determination by In Vitro Methods of Photoprotective Efficacy, Antigenotoxicity and Safety

by Jorge Luis Fuentes, Carlos Adolfo Pedraza Barrera, Diego Armando Villamizar Mantilla, Silvia Juliana Flórez González, Lady Johanna Sierra, Raquel Elvira Ocazionez and Elena E. Stashenko

Molecules 2022, 27(17), 5525; https://doi.org/10.3390/molecules27175525 - 27 Aug 2022

Cited by 5 | Viewed by 4612

Abstract

Plants are sources of sunscreen ingredients that prevent cellular mutations involved in skin cancer and aging. This study investigated the sunscreen properties of the extracts from some ornamental plants growing in Colombia. The UV filter capability of the flower extracts obtained from Rosa [...] Read more.

Plants are sources of sunscreen ingredients that prevent cellular mutations involved in skin cancer and aging. This study investigated the sunscreen properties of the extracts from some ornamental plants growing in Colombia. The UV filter capability of the flower extracts obtained from Rosa centifolia L., Posoqueria latifolia (Rudge) Schult, and Ipomoea horsfalliae Hook. was examined. Photoprotection efficacies were evaluated using in vitro indices such as sun protection factor and critical wavelength. UVB antigenotoxicity estimates measured with the SOS Chromotest were also obtained. Extract cytotoxicity and genotoxicity were studied in human fibroblasts using the trypan blue exclusion and Comet assays, respectively. Major compounds of the promising flower extracts were identified by UHPLC–ESI+–Orbitrap–MS. The studied extracts showed high photoprotection efficacy and antigenotoxicity against UVB radiation, but only the P. latifolia extract showed broad-spectrum photoprotection at non-cytotoxic concentrations. The P. latifolia extract appeared to be safer for human fibroblast cells and the R. centifolia extract was shown to be moderately cytotoxic and genotoxic at the highest assayed concentrations. The I. horsfalliae extract was unequivocally cytotoxic and genotoxic. The major constituents of the promising extracts were as follows: chlorogenic acid, ecdysterone 20E, rhamnetin-rutinoside, cis-resveratrol-diglucoside, trans-resveratrol-diglucoside in P. latifolia; quercetin, quercetin-glucoside, quercetin-3-rhamnoside, kaempferol, kaempferol-3-glucoside, and kaempferol-rhamnoside in R. centifolia. The potential of the ornamental plants as sources of sunscreen ingredients was discussed. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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19 pages, 5655 KiB

Open AccessArticle

Comparison by Life-Cycle Assessment of Alternative Processes for Carvone and Verbenone Production

by Jaime-Andrés Becerra, Juan-Miguel González and Aída-Luz Villa

Molecules 2022, 27(17), 5479; https://doi.org/10.3390/molecules27175479 - 26 Aug 2022

Cited by 1 | Viewed by 1788

Abstract

Verbenone and carvone are allylic monoterpenoid ketones with many applications in the fine chemicals industry that can be obtained, respectively, from the allylic oxidation of α-pinene and limonene over a silica-supported iron hexadecachlorinated phthalocyanine (FePcCl₁₆-NH₂-SiO₂) catalyst [...] Read more.

Verbenone and carvone are allylic monoterpenoid ketones with many applications in the fine chemicals industry that can be obtained, respectively, from the allylic oxidation of α-pinene and limonene over a silica-supported iron hexadecachlorinated phthalocyanine (FePcCl₁₆-NH₂-SiO₂) catalyst and with t-butyl hydroperoxide (TBHP) as oxidant. As there are no reported analyses of the environmental impacts associated with catalytic transformation of terpenes into value-added products that include the steps associated with synthesis of the catalyst and several options of raw materials in the process, this contribution reports the evaluation of the environmental impacts in the conceptual process to produce verbenone and carvone considering two scenarios (SI-raw-oils and SII-purified-oils). The impact categories were evaluated using ReCiPe and IPCC methods implemented in SimaPro 9.3 software. The environmental impacts in the synthesis of the heterogeneous catalyst FePcCl₁₆-NH₂-SiO₂ showed that the highest burdens in terms of environmental impact come from the use of fossil fuel energy sources and solvents, which primarily affect human health. The most significant environmental impacts associated with carvone and verbenone production are global warming and fine particulate matter formation, with fewer environmental impacts associated with the process that starts directly from turpentine and orange oils (SI-raw-oils) instead of the previously extracted α-pinene and limonene (SII-purified-oils). As TBHP was identified as a hotspot in the production process of verbenone and carvone, it is necessary to choose a more environmentally friendly and energy-efficient oxidizing agent for the oxidation of turpentine and orange oils. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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11 pages, 1000 KiB

Open AccessArticle

Chemical Composition and Antifungal, Anti-Inflammatory, Antiviral, and Larvicidal Activities of the Essential Oils of Zanthoxylum acanthopodium DC. from China and Myanmar

by Jingjing Yang, Xingzhen Song, Huabin Hu, Wu Zhong, Ruiyuan Cao, Youkai Xu and Ren Li

Molecules 2022, 27(16), 5243; https://doi.org/10.3390/molecules27165243 - 17 Aug 2022

Cited by 4 | Viewed by 1753

Abstract

Zanthoxylum acanthopodium DC. is a widely used traditional medicinal plant to treat fever, flu, stomachache, traumatic injury, and mosquito bite in tropical and subtropical Asia. This study aimed to investigate the antifungal, anti-inflammatory, antiviral, and larvicidal activities of its fruit essential oil. The [...] Read more.

Zanthoxylum acanthopodium DC. is a widely used traditional medicinal plant to treat fever, flu, stomachache, traumatic injury, and mosquito bite in tropical and subtropical Asia. This study aimed to investigate the antifungal, anti-inflammatory, antiviral, and larvicidal activities of its fruit essential oil. The essential oil sample from China (EOZC) was mainly composed of limonene (29.78%) and β-myrcene (26.65%), while the sample from Myanmar (EOZM) was dominated by Terpinen-4-ol (43.35%). Both essential oils showed antifungal activity, with 90% minimum inhibitory concentration (MIC₉₀) values ranging from 26.3 to 499 μg/mL. By obviously inhibiting nitric oxide (NO) in RAW 264.7 cells, EOZC (IC₅₀, 16 μg/mL) showed comparable anti-inflammatory activity to the positive control L-NMMA (IC₅₀, 12.2 μg/mL). EOZM showed significant antiviral activity against the dengue virus with an IC₅₀ value of 13 μg/mL. Additionally, both EOZC and EOZM demonstrated dose-dependent larvicidal activity against Aedes albopictus, with LC₅₀ and LC₉₀ values ranging from 45.8 to 144.0 μg/mL. Our results contribute a theoretical foundation for the further application of Zanthoxylum acanthopodium DC. as an antifungal and anti-inflammatory ingredient in the pharmaceutical industry and further indicate that it has the potential to be developed as a new source of natural and eco-friendly medicine for the prevention and treatment of dengue virus. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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15 pages, 1179 KiB

Open AccessArticle

Evaluation of Antioxidant and Cytotoxic Activity of Hydro-Ethanolic Extracts Obtained from Steiractinia aspera Cuatrec

by Laura Gamboa-Carvajal, Carlos Jara-Gutiérrez, Joan Villena, Lautaro Taborga, Jairo René Martínez, Luis Espinoza and Elena E. Stashenko

Molecules 2022, 27(13), 4186; https://doi.org/10.3390/molecules27134186 - 29 Jun 2022

Cited by 2 | Viewed by 1375

Abstract

In this work, the antioxidant activity of the hydro-ethanolic extracts of the leaves, flowers, and aerial parts of Steiractinia aspera Cuatrec, both fresh and post-distillation, was evaluated by ABTS^+·, FRAP, H₂O₂ and DPPH assays. The cytotoxic activity was [...] Read more.

In this work, the antioxidant activity of the hydro-ethanolic extracts of the leaves, flowers, and aerial parts of Steiractinia aspera Cuatrec, both fresh and post-distillation, was evaluated by ABTS^+·, FRAP, H₂O₂ and DPPH assays. The cytotoxic activity was evaluated in MCF-7, MCF-10A and HT-29 cell lines. The hydro-ethanolic extracts were obtained by matrix solid-phase dispersion (MSPD) and ultrasound-assisted solvent extraction (SE). The fresh-leaf MSPD extract had the highest antioxidant activity, and the post-distillation leaf ultrasound-assisted SE extract had the highest cytotoxicity in the MCF-7 breast cancer cell line, although not selective, which was evaluated by sulforhodamine B assay. On the other hand, ROS was evaluated by flow cytometry which showed that post-distillation leaf extract is pro-oxidant. Chlorogenic acid, kaempferol-3-glucoside and quercetin were found in the fresh leaves’ extracts, according to HPLC-DAD. PLC-DAD permitted the isolation of p-coumaric acid, E-3-(4-(((E)-3-(3,4-dihydroxyphenyl) acryloyl) oxy)-3-hydroxyphenyl) acrylic acid and a diglucosylated derivative of ursolic acid, which were analyzed by ¹H and ¹³C NMR. Our results suggest that the fresh leaf extract of Steiractinia aspera Cuatrec has potential use for antioxidant applications. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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Review

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27 pages, 816 KiB

Open AccessReview

The Cytotoxic and Inhibitory Effects of Plant Derivatives on Candida albicans Biofilms: A Scoping Review

by Manuela Loaiza-Oliva, Laura Arias-Durango and María Cecilia Martínez-Pabón

Molecules 2023, 28(1), 130; https://doi.org/10.3390/molecules28010130 - 23 Dec 2022

Cited by 2 | Viewed by 1643

Abstract

Candida albicans infections are related to biofilm formation. The increase in antifungal resistance and their adverse effects have led to the search for therapeutic options as plant derivatives. This scoping review aims to identify the current status of in vitro research on the [...] Read more.

Candida albicans infections are related to biofilm formation. The increase in antifungal resistance and their adverse effects have led to the search for therapeutic options as plant derivatives. This scoping review aims to identify the current status of in vitro research on the cytotoxicity and inhibitory effects of plant derivatives on C. albicans biofilms. In this study, PRISMA items were followed. After recognition of the inclusion criteria, full texts were read and disagreements were resolved with a third party. A risk of bias assessment was performed, and information was summarized using Microsoft Office Excel. Thirty-nine papers fulfilling the selection criteria were included. The risk of bias analysis identified most of the studies as low risk. Studies evaluated plant derivatives such as extracts, essential oils, terpenes, alkaloids, flavonoids and polyphenols. Some studies evaluated the inhibition of C. albicans biofilm formation, inhibition on preformed biofilms or both. The derivatives at concentrations greater than or equal to those that have an inhibitory effect on C. albicans biofilms, without showing cytotoxicity, include magnoflorin, ellagic acid, myricetin and eucarobustol from Eucalyptus robusta and, as the works in which these derivatives were studied are of good quality, it is desirable to carry out study in other experimental phases, with methodologies that generate comparable information. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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54 pages, 12123 KiB

Open AccessReview

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

by Mohammed F. Arshad, Aftab Alam, Abdullah Ayed Alshammari, Mohammed Bader Alhazza, Ibrahim Mohammed Alzimam, Md Anish Alam, Gulam Mustafa, Md Salahuddin Ansari, Abdulelah M. Alotaibi, Abdullah A. Alotaibi, Suresh Kumar, Syed Mohammed Basheeruddin Asdaq, Mohd. Imran, Pran Kishore Deb, Katharigatta N. Venugopala and Shahamah Jomah

Molecules 2022, 27(13), 3994; https://doi.org/10.3390/molecules27133994 - 21 Jun 2022

Cited by 47 | Viewed by 6826

Abstract

For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds [...] Read more.

For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds rendering aromatic ring properties. On account of its aromaticity, the ring has many reactive positions where donor–acceptor, nucleophilic, oxidation reactions, etc., may take place. Molecules containing a thiazole ring, when entering physiological systems, behave unpredictably and reset the system differently. These molecules may activate/stop the biochemical pathways and enzymes or stimulate/block the receptors in the biological systems. Therefore, medicinal chemists have been focusing their efforts on thiazole-bearing compounds in order to develop novel therapeutic agents for a variety of pathological conditions. This review attempts to inform the readers on three major classes of thiazole-bearing molecules: Thiazoles as treatment drugs, thiazoles in clinical trials, and thiazoles in preclinical and developmental stages. A compilation of preclinical and developmental thiazole-bearing molecules is presented, focusing on their brief synthetic description and preclinical studies relating to structure-based activity analysis. The authors expect that the current review may succeed in drawing the attention of medicinal chemists to finding new leads, which may later be translated into new drugs. Full article

(This article belongs to the Special Issue Essential Oils and Their Derivatives: Fundamental and Applied Studies towards the Development of the Circular Bioeconomy)

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