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20 pages, 3632 KiB

Open AccessArticle

Extraction of Diterpene-Phytochemicals in Raw and Roasted Coffee Beans and Beverage Preparations and Their Relationship

by Fábio Junior Moreira Novaes, Maria Alice Esteves da Silva, Diana Cardoso Silva, Francisco Radler de Aquino Neto and Claudia Moraes Rezende

Plants 2023, 12(8), 1580; https://doi.org/10.3390/plants12081580 - 07 Apr 2023

Viewed by 1781

Abstract

Cafestol and kahweol are expressive furane-diterpenoids from the lipid fraction of coffee beans with relevant pharmacological properties for human health. Due to their thermolability, they suffer degradation during roasting, whose products are poorly studied regarding their identity and content in the roasted coffee [...] Read more.

Cafestol and kahweol are expressive furane-diterpenoids from the lipid fraction of coffee beans with relevant pharmacological properties for human health. Due to their thermolability, they suffer degradation during roasting, whose products are poorly studied regarding their identity and content in the roasted coffee beans and beverages. This article describes the extraction of these diterpenes, from the raw bean to coffee beverages, identifying them and understanding the kinetics of formation and degradation in roasting (light, medium and dark roasts) as the extraction rate for different beverages of coffee (filtered, Moka, French press, Turkish and boiled). Sixteen compounds were identified as degradation products, ten derived from kahweol and six from cafestol, produced by oxidation and inter and intramolecular elimination reactions, with the roasting degree (relationship between time and temperature) being the main factor for thermodegradation and the way of preparing the beverage responsible for the content of these substances in them. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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12 pages, 1842 KiB

Open AccessArticle

Microwave-Assisted Hydrodistillation of the Insecticidal Essential Oil from Carlina acaulis: A Fractional Factorial Design Optimization Study

by Eleonora Spinozzi, Marta Ferrati, Desiree Lo Giudice, Eugenio Felicioni, Riccardo Petrelli, Giovanni Benelli, Filippo Maggi and Marco Cespi

Plants 2023, 12(3), 622; https://doi.org/10.3390/plants12030622 - 31 Jan 2023

Cited by 2 | Viewed by 1585

Abstract

Recently, microwave-assisted hydrodistillation (MAH) has been reported as an innovative technique leading to increased essential oil (EO) extraction yield, coupled with reduced extraction time and energy costs. The EO of Carlina acaulis L. (Asteraceae), mainly constituted by carlina oxide (>95%) and conventionally obtained [...] Read more.

Recently, microwave-assisted hydrodistillation (MAH) has been reported as an innovative technique leading to increased essential oil (EO) extraction yield, coupled with reduced extraction time and energy costs. The EO of Carlina acaulis L. (Asteraceae), mainly constituted by carlina oxide (>95%) and conventionally obtained through traditional hydrodistillation (HD), has been reported as extremely effective against several arthropod vectors and pests of medical and economic importance with limited impact on non-target species, including mammals. This study aimed to the optimization of the EO extraction through MAH by using a one-step design of experiments (DoE) approach that allowed us to relate the characteristics of the produced EOs with the applied experimental conditions using mathematical models. The preliminary screening allowed us to optimize the protocol only by the extraction time, skipping complex data analysis. Moreover, the comparison of the optimized MAH conditions with traditional HD pointed out the higher efficiency of MAH in terms of EO yield (0.65 and 0.49% for MAH and HD, respectively) and extraction time (210 min for MAH). The results obtained confirmed the promising role that MAH could have in C. acaulis EO extraction, with increased yield and reduced extraction time, water consumption, and energy costs, and being employable on an industrial scale, with special reference to insecticidal and acaricidal formulations. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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18 pages, 2481 KiB

Open AccessArticle

Volatile Metabolome and Aroma Differences of Six Cultivars of Prunus mume Blossoms

by Ting Li, Xi Zhao and Xueli Cao

Plants 2023, 12(2), 308; https://doi.org/10.3390/plants12020308 - 09 Jan 2023

Cited by 4 | Viewed by 1862

Abstract

Prunus mume is a traditional Chinese plant with high ornamental and application values due to its very early blooming and unique fragrance. Long-term breeding and cultivation have resulted in a variety of P. mume blossoms and have made their exploitation more possible. Existing [...] Read more.

Prunus mume is a traditional Chinese plant with high ornamental and application values due to its very early blooming and unique fragrance. Long-term breeding and cultivation have resulted in a variety of P. mume blossoms and have made their exploitation more possible. Existing studies on the volatile metabolome and aroma of P. mume blossoms are limited. In this study, six extensively planted cultivars of P. mume blossoms, including Gulihong (GLH), Yudie (YD), LvE (LE), Dongfang Zhusha (DFZS), Jiangmei (JM), and Gongfen (GF), were investigated for their differences in terms of volatile metabolome, as well as their aroma characteristics based on the strategies and methods of metabolomics. The volatile metabolites were analyzed using HS-SPME-GC-MS technique. A total of eighty-nine compounds were detected and sixty-five of them were tentatively identified, including thirty-seven phenylpropanoids/benzenes, seventeen fatty acid derivatives, ten terpenoids, and one other compound. YD contains the most volatile metabolites in terms of number and amounts, which impart more abundant aromas to this cultivar. Fifteen differential compounds were screened through the untargeted metabolic analysis of twenty-nine samples by principal component analysis (PCA) and partial least squares-discriminant analysis (PLS-DA), while nine compounds were screened based on the odor activity value (OAV) analysis of the sixty-five identified compounds. GLH and GF, JM and LE were found to be more similar to each other based on chemometrics analysis of both volatile contents and OAVs, while YD and DFZS were markedly different from other cultivars. Six main metabolites, including benzaldehyde, methyl benzoate, benzyl acetate, eugenol, (E)-cinnamic alcohol, and 4-allylphenol, together with 2-nonenal, 3,4-dimethoxytoluene, and trans-β-Ionone were screened as differential compounds, owing to their higher contents and/or lower olfactory threshold, which endow an almond, cherry, phenolic, wintergreen, cananga odorata, floral, jasmine, hyacinth, cinnamon, clove, woody, medicinal, and violet fragrance to each variety, and greatly contribute to the aroma differences of six cultivars of P. mume blossom. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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22 pages, 1007 KiB

Open AccessArticle

Volatile Compounds in Norway Spruce (Picea abies) Significantly Vary with Season

by Katja Schoss, Nina Kočevar Glavač and Samo Kreft

Plants 2023, 12(1), 188; https://doi.org/10.3390/plants12010188 - 02 Jan 2023

Viewed by 2107

Abstract

Norway spruce (Picea abies) is one of the most important commercial conifer species naturally distributed in Europe. In this paper, the composition and abundance of essential oil and hydrosol from the needles and branches of P. abies were investigated with an [...] Read more.

Norway spruce (Picea abies) is one of the most important commercial conifer species naturally distributed in Europe. In this paper, the composition and abundance of essential oil and hydrosol from the needles and branches of P. abies were investigated with an additional evaluation of changes related to different times of the year, annual shoots and branches, and differences in composition under different microenvironments. Essential oils and hydrosols obtained via hydrodistillation were analyzed using gas chromatography–mass spectrometry (GC-MS), where 246 compounds in essential oil and 53 in hydrosols were identified. The relative amounts of monoterpenes, sesquiterpenes, and diterpenes in essential oil changed significantly during the year, with the highest peak of monoterpenes observed in April (72%), the highest abundance of sesquiterpenes observed in August (21%), and the highest abundance of diterpenes observed in June (27%). The individual compound with the highest variation was manool, with variation from 1.5% (April) to 18.7% (June). Our results also indicate that the essential oil with the lowest allergenic potential (lowest quantity of limonene and linalool) was obtained in late spring or summer. Location had no significant influence on composition, while the method of collection for distillation (whole branch or annual shoots) had a minor influence on the composition. All nine main compounds identified in the hydrosol samples were oxygenated monoterpenes. The composition of P. abies hydrosol was also significantly affected by season. The method of preparing the branches for distillation did not affect the composition of P. abies hydrosol, while the location had a minor effect on composition. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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11 pages, 4424 KiB

Open AccessCommunication

Tissue-Specific Profiling of Biflavonoids in Ginkgo (Ginkgo biloba L.)

by Marija Kovač Tomas, Iva Jurčević and Dunja Šamec

Plants 2023, 12(1), 147; https://doi.org/10.3390/plants12010147 - 28 Dec 2022

Cited by 4 | Viewed by 1735

Abstract

Biflavonoids are flavonoid dimers that are much less studied than monomeric flavonoids. Their precise distribution among plants and their role in plants is still unknown. Here, we have developed a HPLC-DAD method that allows us to separate and simultaneously determine the five major [...] Read more.

Biflavonoids are flavonoid dimers that are much less studied than monomeric flavonoids. Their precise distribution among plants and their role in plants is still unknown. Here, we have developed a HPLC-DAD method that allows us to separate and simultaneously determine the five major biflavonoids (amentoflavone, bilobetin, ginkgetin, isoginkgetin, and sciadopitysin) in ginkgo (Ginkgo biloba L.). We performed tissue-specific profiling of biflavonoids in ten different plant parts: tree bark, twigs bark, twigs without bark, buds, leaf petioles, leaf blades, seed stalks, sarcotesta, nutshells, and kernels. We did not detect biflavonoids in plant parts not in direct contact with the environment (twigs without bark, nutshells, and kernels). We found the highest total biflavonoids content in leaves, where sciadopitysin was predominant. In contrast, in the bark, amentoflavone was the predominant biflavonoid, suggesting that more methylated biflavonoids accumulate in leaves and seeds. This is probably related to their biological function, which remains to be determined. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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8 pages, 613 KiB

Open AccessFeature PaperArticle

Essential Oil Variability of Superior Myrtle (Myrtus communis L.) Accessions Grown under the Same Conditions

by Donya Shahbazian, Akbar Karami, Fatemeh Raouf Fard, Saeid Eshghi and Filippo Maggi

Plants 2022, 11(22), 3156; https://doi.org/10.3390/plants11223156 - 18 Nov 2022

Viewed by 1271

Abstract

Myrtle (Myrtus communis L., Myrtaceae) has numerous applications in pharmacology, food technology, and cosmetic industry. The current research aimed at measuring variations in the leaf essential oil (EO) compositions of 14 superior myrtle accessions originating in natural habitats of south Iran. The [...] Read more.

Myrtle (Myrtus communis L., Myrtaceae) has numerous applications in pharmacology, food technology, and cosmetic industry. The current research aimed at measuring variations in the leaf essential oil (EO) compositions of 14 superior myrtle accessions originating in natural habitats of south Iran. The plants were grown under greenhouse conditions. Fresh leaf samples were harvested in June 2021. Based on dry matter, the extractable amount of EO in the accessions ranged from 0.42% (BN2) to 2.6% (BN5). According to GC/MS analysis, the major compounds in the EO were α-pinene (2.35–53.09%), linalyl acetate (0–45.3%), caryophyllene oxide (0.97–21.8%), germacrene D (0–19.19%), α-humulene (0–18.97%), 1,8-cineole (0–18.0%), limonene (0–17.4%), and p-cymene (0–13.2%). These myrtle accessions were classified into four groups, including I: caryophyllene oxide/germacrene D/α-humulene/methyl eugenol chemotype; II: α-pinene/p-cymene/α-humulene and (E)-β-caryophyllene; III: α-pinene/1,8-cineole, and linalool; IV: linalyl acetate/γ-terpinene/1,8, cineole/limonene. These classifications were established by considering the main EO components using hierarchical cluster analysis (HCA) and principal component analysis (PCA). In summary, this study provided new insights into available opportunities of selecting suitable genotypes for commercial cultivation purposes and planning breeding programs in the future. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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13 pages, 1317 KiB

Open AccessArticle

Efficiency of Natural Deep Eutectic Solvents to Extract Phenolic Compounds from Agrimonia eupatoria: Experimental Study and In Silico Modelling

by Mila Lazović, Ilija Cvijetić, Milica Jankov, Dušanka Milojković-Opsenica, Jelena Trifković and Petar Ristivojević

Plants 2022, 11(18), 2346; https://doi.org/10.3390/plants11182346 - 08 Sep 2022

Cited by 4 | Viewed by 1849

Abstract

To replace common organic solvents that present inherent toxicity and have high volatility and to improve the extraction efficiency, a range of natural deep eutectic solvents (NADESs) were evaluated for the extraction of phenolic compounds from Agrimonia eupatoria. Screening of NADES efficiency [...] Read more.

To replace common organic solvents that present inherent toxicity and have high volatility and to improve the extraction efficiency, a range of natural deep eutectic solvents (NADESs) were evaluated for the extraction of phenolic compounds from Agrimonia eupatoria. Screening of NADES efficiency was carried out based on the total phenolic and flavonoid content and radical-scavenging activity, determined by spectrophotometry, as well as phenolic compounds quantified, obtained using ultra-high-performance liquid chromatography with a diode array detector and a triple-quadrupole mass spectrometer. Increased extraction efficiency when compared with organic solvent was achieved using NADES mixtures choline chloride (ChCl):urea 1:2 and choline chloride:glycerol 1:1. Flavonol glycosides were the most abundant compounds in all extracts. The COSMO-RS model provided insights into the most important intermolecular interactions that drive the extraction process. Moreover, it could explain the extraction efficiency of flavonol glycosides using ChCl:glycerol NADES. The current article offers experimental evidence and mechanistic insights for the selection of optimal NADES to extract bioactive components from Agrimonia eupatoria. Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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16 pages, 4419 KiB

Open AccessArticle

Isolation and In Silico Inhibitory Potential against SARS-CoV-2 RNA Polymerase of the Rare Kaempferol 3-O-(6″-O-acetyl)-Glucoside from Calligonum tetrapterum

by Yerlan M. Suleimen, Rani A. Jose, Gulnur K. Mamytbekova, Raigul N. Suleimen, Margarita Y. Ishmuratova, Wim Dehaen, Bshra A. Alsfouk, Eslam B. Elkaeed, Ibrahim H. Eissa and Ahmed M. Metwaly

Plants 2022, 11(15), 2072; https://doi.org/10.3390/plants11152072 - 08 Aug 2022

Cited by 12 | Viewed by 2398

Abstract

The phytochemical constituents of Calligonum tetrapterum Jaub. & Spach (Family Polygonaceae) were studied for the first time. The study resulted in the isolation of the rare flavonol glycoside, kaempferol 3-O-(6″-O-acetyl)-glucoside,(K3G-A). The potential inhibitive activity of K3G-A toward SARS-CoV-2 was [...] Read more.

The phytochemical constituents of Calligonum tetrapterum Jaub. & Spach (Family Polygonaceae) were studied for the first time. The study resulted in the isolation of the rare flavonol glycoside, kaempferol 3-O-(6″-O-acetyl)-glucoside,(K3G-A). The potential inhibitive activity of K3G-A toward SARS-CoV-2 was investigated utilizing several in silico approaches. First, molecular fingerprints and structural similarity experiments were carried out for K3G-A against nine co-crystallized ligands of nine proteins of SARS-CoV-2 to reveal if there is a structural similarity with any of them. The conducted studies showed the high similarity of K3G-A and remdesivir, the co-crystallized ligand of SARS-CoV-2 RNA-dependent RNA polymerase (PDB ID: 7BV2), RdRp. To validate these findings, a DFT study was conducted and confirmed the proposed similarity on the electronic and orbital levels. The binding of K3G-A against RdRp was confirmed through molecular docking studies exhibiting a binding energy of −27.43 kcal/mol, which was higher than that of remdesivir. Moreover, the RdRp-K3G-A complex was subjected to several MD studies at 100 ns that authenticated the accurate mode of binding and the correct dynamic behavior. Finally, in silico ADMET and toxicity evaluation of K3G-A was conducted and denoted the safety and the drug-likeness of K3G-A. In addition to K3G-A, two other metabolites were isolated and identified to be kaempferol (K) and β-sitosterol (β-S). Full article

(This article belongs to the Special Issue Extraction Technologies, Isolation, Separation, and Application of Phytochemicals)

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