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16 pages, 3820 KiB

Open AccessEditor’s ChoiceArticle

Simple Green Purification of Spilanthol from Natural Deep Eutectic Solvent and Ethanolic Acmella oleracea (L.) R.K. Jansen Extracts Using Solid-Phase Extraction

by Fabian Alperth, Sebastian Erhart, Olaf Kunert and Franz Bucar

Separations 2024, 11(8), 251; https://doi.org/10.3390/separations11080251 - 20 Aug 2024

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Abstract

Spilanthol is a major N-alkylamide constituent of Acmella oleracea (L.) R.K. Jansen with diverse pharmacological properties. We recently showed the applicability of NADES (natural deep eutectic solvents) for the green extraction of spilanthol. However, the purification of targets from NADES poses a [...] Read more.

Spilanthol is a major N-alkylamide constituent of Acmella oleracea (L.) R.K. Jansen with diverse pharmacological properties. We recently showed the applicability of NADES (natural deep eutectic solvents) for the green extraction of spilanthol. However, the purification of targets from NADES poses a challenging step due to their non-volatility. A simple green method to retrieve spilanthol with minimal instrumental effort was devised, fractioning NADES (choline chloride/methylurea, choline chloride/1,2-propanediol, choline chloride/citric acid) and dry ethanolic extracts by SPE on C18 material, eluting merely with ethanolic solutions. The relative distribution of spilanthol and organic adulteration in SPE fractions were detected by HPLC-DAD, followed by scale-up, quantification and purity determination in an NMR-based approach. Isocratic elution with 52% ethanol (v/v) proved suitable in all experiments. The three purest 10 mL fractions combined yielded 12.21 mg spilanthol at 71.65% purity from NADES extract ChCl/P (choline chloride/1,2-propanediol, molar ratio 1:2, +20% m/m water). Ethanolic extract samples showed purities ranging from 77.27 to 80.27% in combined raw fractions. For all samples, purity increased by removing non-soluble substances from organic solutions. Pooled NADES extract fractions showed 89.71% in final samples, ethanolic extracts 87.25 to 91.93%. The highest purities of individual fractions per extract were 89.23 to 94.15%. This cheap and simple purification process is promising to acquire spilanthol for research purposes or as a sample preparation step before HPLC on a semi-preparative to preparative scale, as the substance is highly priced and scarcely available on the market. Organic solvents can be reused, and preliminary scale-up possibilities are shown. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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9 pages, 1567 KiB

Open AccessArticle

Synthesis and Biological Evaluation of Desacetylmatricarin Derivatives Isolated from Basin Big Sagebrush

by N. Evelin Paucar, Shanae Van Leuven, Karl De Jesus, Srinath Pashikanti, Sameena Mateen, Samjhana Pradhan and Kavita Sharma

Separations 2024, 11(7), 217; https://doi.org/10.3390/separations11070217 - 19 Jul 2024

Viewed by 731

Abstract

Desacetylmatricarin, a sesquiterpene lactone (SL), is the major component extracted from the aerial parts of basin big sagebrush (Artemisia tridentata subsp. tridentata). The medicinal benefits of desacetylmatricarin have not been fully exploited; thus, the current study is an exploratory study to [...] Read more.

Desacetylmatricarin, a sesquiterpene lactone (SL), is the major component extracted from the aerial parts of basin big sagebrush (Artemisia tridentata subsp. tridentata). The medicinal benefits of desacetylmatricarin have not been fully exploited; thus, the current study is an exploratory study to assess its biological activity as a potential source for anti-cancer properties. Herein, we have synthesized desacetylmatricarin derivatives using reported methodologies and examined their anti-cancer properties by submitting the synthesized compounds to the National Cancer Institute (NCI). Our previous studies on the evaluation of the biological activity of the SLs isolated from the basin big sagebrush against the NCI-60 cancer cell line screening expanded our work on derivatizing desacetylmatricarin. All of the compounds synthesized from desacetylmatricarin, which was isolated and purified from the basin big sagebrush, were obtained in high yields. The structures of the synthesized desacetylmatricarin derivatives were confirmed by NMR experiments. These compounds were then evaluated against the NCI-60 cancer cell line screening. NCI-60 cancer cell line screening revealed that some of the chemically modified desacetylmatricarin derivatives showed greater biological activity as compared to the natural precursor in a one-dose assay. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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18 pages, 4369 KiB

Open AccessArticle

Effects of Extraction Methods on Volatile Oil Profiles of Cinnamomi ramulus–Zingiberis rhizoma recens Couplet Medicines

by Xiaodong Xin, Xinnong Li, Jiabao Chen, Chuanghui Shen, Xiaohan Shi, Lei Wang and Chunhua Li

Separations 2024, 11(7), 206; https://doi.org/10.3390/separations11070206 - 2 Jul 2024

Viewed by 931

Abstract

Cinnamomi ramulus (CR, Guizhi in Chinese) and Zingiberis rhizoma recens (ZRR, Shengjiang in Chinese) are couplet medicines (drug pairs or drug combinations) in traditional Chinese medicine prescriptions. They contain a high amount of volatile oils which endow them with unique flavors and pharmacological [...] Read more.

Cinnamomi ramulus (CR, Guizhi in Chinese) and Zingiberis rhizoma recens (ZRR, Shengjiang in Chinese) are couplet medicines (drug pairs or drug combinations) in traditional Chinese medicine prescriptions. They contain a high amount of volatile oils which endow them with unique flavors and pharmacological activities. Extraction methods have a great influence on the extraction efficiency and composition of volatile oils. Firstly, the volatile oils of CR and ZRR were extracted by steam distillation (SD) and analyzed by GC-MS to obtain their chemical profiles. In total, 35 and 55 compounds were identified in the volatile oils of CR and ZRR, respectively. In order to find a suitable extraction method for the couplet medicine CR-ZRR, subsequently, steam distillation (SD), azeotropic distillation (AD) and supercritical fluid extraction (SFE) were applied to extract the volatile oils from CR-ZRR. The average extraction yields by SD, AD and SFE were 0.573%, 0.62% and 2.135%, respectively. The chemical composition of the volatile oils was then analyzed by GC-MS. In total, 73, 59 and 71 compounds were identified from the extracts obtained by SD, AD and SFE, respectively. Principal component analysis (PCA) and OPLS-DA showed that citral, (E)-cinnamaldehyde dimethyl acetal, zingiberene, cinnamaldehyde and β-sesquiphellandrene were the main contributors to distinguish the volatile oils that were obtained by different processes. Considering the chemical diversity and the total content of the main bioactive components of the volatiles oils, SD was more suitable for CR-ZRR volatile oil extraction. This study provides a basis for elucidating the chemical composition and suitable extraction method for the volatile oils of CR-ZRR. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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20 pages, 5831 KiB

Open AccessArticle

Enhanced Antioxidant Extraction from Lonicerae japonicae Flos Based on a Novel Optimization Strategy with Tailored Deep Eutectic Solvents

by Wen-Wen Deng, Bo Sun, Han Yang, Xiao-Jie Hou, Yong-Jian Zhang, Tian-Xiang Gan, Xin-Yi Cheng, Ao Yuan, Xiao-Yang Dong, Cong-Yu Zhou, Ying Deng, Ya-Qian Xiao, Reza Ghiladi, Hui Li and Jun Wang

Separations 2024, 11(6), 189; https://doi.org/10.3390/separations11060189 - 17 Jun 2024

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Abstract

Lonicerae japonicae Flos (LJF) is a natural plant containing abundant antioxidant ingredients. In order to extract more antioxidants from LJF, in this study, a novel strategy was proposed for optimizing the extraction factor level by response surface methodology with a tailored deep eutectic [...] Read more.

Lonicerae japonicae Flos (LJF) is a natural plant containing abundant antioxidant ingredients. In order to extract more antioxidants from LJF, in this study, a novel strategy was proposed for optimizing the extraction factor level by response surface methodology with a tailored deep eutectic solvent (DES) as the extraction solvent and antioxidant ability as the evaluation index. After optimizing the composition of DES and the extraction condition, the extracts obtained by our proposed method yielded better antioxidant ability (229.1–249.1 μmol TE/g DW) and higher antioxidant contents (34.2–36.5 mg GAE/g DW for total phenolics and 119.6–123.0 mg RE/g DW for total flavonoids) from LJF in 5 min without organic solvent consumption that were significantly superior to the Chinese Pharmacopoeia extraction method. The K-T solvation parameter and a scanning electron microscope were adopted to explore the extraction mechanism, and the results showed that the polarity and damage effect on plant cells of DES were crucial for the extraction of antioxidants. In addition, after combining the HPLC fingerprint and partial least squares model, chlorogenic acid, rutin, and 3,5-O-Dicaffeoylquinic acid were screened as the antioxidant Q-markers of LJF. This work demonstrates that an optimization strategy based on antioxidant ability and tailored DES has the potential to extract more antioxidants from natural plants. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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16 pages, 2857 KiB

Open AccessArticle

Natural Deep Eutectic Solvent-Based Ultrasound-Assisted Extraction of Flavonoids from Fagopyrum tataricum Bran

by Zhou Xu, Xiaomei Da, Jipeng Qu and Shiming Xiao

Separations 2024, 11(5), 145; https://doi.org/10.3390/separations11050145 - 8 May 2024

Cited by 1 | Viewed by 1369

Abstract

In this study, eleven kinds of flavonoids were identified from F. tataricum bran (FTB) by UPLC-Q-TOF-MS, and HPLC-DAD analysis revealed that four compounds, including rutin, quercetin, kaempferol, and nicotiflorin, were the most significant components. Subsequently, natural deep eutectic solvent-based ultrasound-assisted extraction (NADES-UAE) was [...] Read more.

In this study, eleven kinds of flavonoids were identified from F. tataricum bran (FTB) by UPLC-Q-TOF-MS, and HPLC-DAD analysis revealed that four compounds, including rutin, quercetin, kaempferol, and nicotiflorin, were the most significant components. Subsequently, natural deep eutectic solvent-based ultrasound-assisted extraction (NADES-UAE) was employed to extract flavonoids from FTB. Among the six kinds of NADES prepared, choline chloride–ethylene glycol (ChCl-EG) was identified as a promising candidate for extracting flavonoids due to its superior extraction performance. The extraction conditions were statistically investigated using response surface methodology conducted by Box-Behnken design (BBD). The optimal operational conditions were as follows: ultrasonic time 268 s, ultrasonic temperature 76 °C, and liquid–solid ratio 43 mL/g, which resulted in a high total flavonoid yield of 40.29 mg/g. Afterwards, the efficient extraction mechanism of NADES-UAE was comprehensively explored through FT-IR spectra, COSMO model, and microstructural analysis. In conclusion, NADES-UAE extraction is considered a green, efficient, and sustainable method for FTB flavonoids. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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16 pages, 4537 KiB

Open AccessArticle

Variations in Essential Oil Biological Activities of Female Cones at Different Developmental Stages from Azorean Cryptomeria japonica (Thunb. ex L.f.) D. Don (Cupressaceae)

by Alexandre Janeiro, Ana Lima, Filipe Arruda, Tanner Wortham, Tânia Rodrigues, José Baptista and Elisabete Lima

Separations 2024, 11(4), 102; https://doi.org/10.3390/separations11040102 - 29 Mar 2024

Cited by 3 | Viewed by 1570

Abstract

In the Azores Archipelago, Cryptomeria japonica is, currently, the most cultivated forestry tree for timber production, landscaping, and gardening, generating large amounts of foliage waste that is used for local essential oils (EOs) production. However, the existing literature on the biological potential of [...] Read more.

In the Azores Archipelago, Cryptomeria japonica is, currently, the most cultivated forestry tree for timber production, landscaping, and gardening, generating large amounts of foliage waste that is used for local essential oils (EOs) production. However, the existing literature on the biological potential of EOs from different C. japonica foliage parts, such as female cones (FC), remains limited. Thus, in the present study, EOs extracted by hydrodistillation from Azorean C. japonica immature and mature FC (IFC and MFC), as well as some major EO components, were screened for their: (i) antioxidant capacity, evaluated by DPPH free-radical-scavenging activity (FRSA) and β-carotene-linoleic acid bleaching activity (BCBA), (ii) antimicrobial activities, assessed by the disc diffusion method against eight bacteria and one fungus, and (iii) toxicity against Artemia salina. Among both FC EO samples, the IFC EO exhibited the best DPPH–FRSA, BCBA, and growth inhibitory activity against Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Penicillium italicum, as well as a slightly increased toxic potential, due to their differential compositions, as assessed by GC–MS analysis. Thus, the FC’s maturation process decreased their EOs’ bioactivities. In conclusion, this finding could help in determining the optimal developmental stage for enhancing the antioxidant and antimicrobial compounds content in FC EOs. In turn, this contributes to increasing the commercial potential of C. japonica’s EO industry. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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17 pages, 4291 KiB

Open AccessArticle

Comprehensive Analysis of Phytochemical Composition, Antioxidant Potential, and Antibacterial Activity of T. polium

by Zineb Timizar, Khalida Boutemak, Amel Hadj Ziane-Zafour, Nabil Touzout, Hichem Tahraoui, Bassem Jaouadi, Meriem Zamouche, Mohammed Kebir, Jie Zhang and Abdeltif Amrane

Separations 2024, 11(4), 90; https://doi.org/10.3390/separations11040090 - 24 Mar 2024

Viewed by 1708

Abstract

This study aims to thoroughly examine the chemicals and effects of the ethanol extract from T. polium’s upper parts. We used the Soxhlet method for extraction, resulting in an extract with a significant yield of 20.6%. Qualitative analysis identified a variety of [...] Read more.

This study aims to thoroughly examine the chemicals and effects of the ethanol extract from T. polium’s upper parts. We used the Soxhlet method for extraction, resulting in an extract with a significant yield of 20.6%. Qualitative analysis identified a variety of compounds, such as tannins, saponins, reducing compounds, terpenoids, quinones, and alkaloids. In quantitative analysis using the colorimetric method, we found the extract was rich in total flavonoids (20.78 mg equivalent QE/g DW extract) and total polyphenols (227.43 mg equivalent GAE/g DW extract). To assess antioxidant potential, we used the ferric reducing antioxidant power (FRAP) method, with ascorbic acid and butylated hydroxytoluene (BHT) as standards. The extract showed moderate activity in both the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and FRAP methods at concentrations of 65 µg/mL and 21 mg/mL, respectively. Additionally, we tested the ethanolic extract against various bacteria using the disk diffusion technique on agar medium. The results indicated that the T. polium extract had moderate effectiveness against Gram-negative bacteria like Pseudomonas aeruginosa ATCC 9027 and Escherichia coli ATCC 8739, as well as Gram-positive bacteria like Staphylococcus aureus ATCC 6538 and Bacillus subtilis ATCC 6633. We further investigated the composition of the ethanolic extract through LC-MS/MS analysis, establishing a detailed profile of phenolic compounds, with six flavonoids identified as the main polyphenolic constituents. This thorough evaluation provides insights into the potential therapeutic uses of T. polium. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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Review

Jump to: Research

27 pages, 9407 KiB

Open AccessReview

Paeoniae Radix Alba and Network Pharmacology Approach for Osteoarthritis: A Review

by Bo Wang, Changcai Bai and Yuanyuan Zhang

Separations 2024, 11(6), 184; https://doi.org/10.3390/separations11060184 - 12 Jun 2024

Viewed by 742

Abstract

Osteoarthritis (OA) is the most common type of arthritis and affects more than 240 million people worldwide; the most frequently affected areas are the hips, knees, feet, and hands. OA pathophysiology is multifactorial, involving genetic, developmental, metabolic, traumatic, and inflammation factors. Therefore, treatments [...] Read more.

Osteoarthritis (OA) is the most common type of arthritis and affects more than 240 million people worldwide; the most frequently affected areas are the hips, knees, feet, and hands. OA pathophysiology is multifactorial, involving genetic, developmental, metabolic, traumatic, and inflammation factors. Therefore, treatments able to address several path mechanisms can help control OA. Network pharmacology is developing as a next-generation research strategy to shift the paradigm of drug discovery from “one drug, one target” to “multi-component, multi-target”. In this paper, network pharmacology is employed to investigate the potential role of Paeoniae Radix Alba (PRA) in the treatment of OA. PRA is a natural product known for its protective effects against OA, which has recently drawn attention because of its ability to provide physiological benefits with fewer toxic effects. This review highlights the anti-inflammatory properties of PRA in treating OA. PRA can be used alone or in combination with conventional therapies to enhance their effectiveness and reduce side effects. The study also demonstrates the use of network pharmacology as a cost-effective and time-saving method for predicting therapeutic targets of PRA in OA treatment. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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30 pages, 1718 KiB

Open AccessReview

Nanofiltration-Assisted Concentration Processes of Phenolic Fractions and Carotenoids from Natural Food Matrices

by Roberto Castro-Muñoz

Separations 2024, 11(2), 64; https://doi.org/10.3390/separations11020064 - 19 Feb 2024

Cited by 1 | Viewed by 2363

Abstract

In new food formulations, carotenoids and phenolic compounds are likely to be the most sought after food ingredients according to their bioactivity, nutraceutical, nutritional value, and compatibility properties once incorporated into food formulations. Such solutes are naturally present in many plant-based sources, and [...] Read more.

In new food formulations, carotenoids and phenolic compounds are likely to be the most sought after food ingredients according to their bioactivity, nutraceutical, nutritional value, and compatibility properties once incorporated into food formulations. Such solutes are naturally present in many plant-based sources, and some portions are directly consumed when enriching food products and formulations; however, some portions, which are contained in the parts of the plant sources not considered edible, including the leaves, peel, and seeds, among other by-products, are commonly wasted. Related to this, scientists have found a new window for obtaining these bioactive molecules, but their recovery remains a challenge. To some extent, the final purification and polishing requires highly selective performance to guarantee the desired properties and concentration. In this regard, membrane technologies, such as nanofiltration (NF), represent an alternative, owing to their highly selective properties when separating low-molecular-weight compounds. NF becomes immediately suitable when the pretreated extracts are subjected to further efficient concentration, fractionation, and polishing of phenolic fractions and carotenoids. The separation efficiency (usually higher than 97%) of NF technology is high according to the low pore size of NF membranes, but the low temperature in process separation also contributes to the separation of thermolabile compounds. Therefore, this paper reviews the ongoing cases of studies reporting the successful separation and polishing of phenolic fractions and carotenoids from distinct sources. In particular, we have focused our attention on the main interactions during the separation process and the drawbacks and advantages of using membranes for such a case study. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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17 pages, 1055 KiB

Open AccessReview

Research Progress on Extraction, Separation, and Purification Methods of Plant Essential Oils

by Weiwei Zhou, Jun Li, Xuefeng Wang, Ling Liu, Yun Li, Rui Song, Mengxue Zhang and Xiumei Li

Separations 2023, 10(12), 596; https://doi.org/10.3390/separations10120596 - 7 Dec 2023

Cited by 4 | Viewed by 6568

Abstract

Essential oils (EOs), also called liquid gold, are known for their wide range of applications and biological activities. The modern use of EOs has received increasing attention for more than 60 years. The precious EOs have been refined from plant raw materials using [...] Read more.

Essential oils (EOs), also called liquid gold, are known for their wide range of applications and biological activities. The modern use of EOs has received increasing attention for more than 60 years. The precious EOs have been refined from plant raw materials using a variety of methods. Since the extraction, separation, and purification methods determine the type, quantity, and stereochemical structure of EO molecules as well as the final yield and quality of EOs, the selection of an appropriate method is crucial. The traditional and emerging extraction methods (hydrodistillation, steam distillation, organic solvent extraction, etc.), as well as separation and purification methods (chromatography, macroporous resin, chemical reaction, etc.), of plant EOs and their main volatile compounds were shown. Our review focused on the principles, processes, characteristics, and applications of these methods, so as to better understand the preparation of pure plant EOs and further guide their large-scale use. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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27 pages, 388 KiB

Open AccessReview

Valorization of Olive Leaves through Polyphenol Recovery Using Innovative Pretreatments and Extraction Techniques: An Updated Review

by Espérance Debs, Anna-Maria Abi-Khattar, Hiba N. Rajha, Roula M. Abdel-Massih, Jean-Claude Assaf, Mohamed Koubaa, Richard G. Maroun and Nicolas Louka

Separations 2023, 10(12), 587; https://doi.org/10.3390/separations10120587 - 29 Nov 2023

Cited by 3 | Viewed by 2612

Abstract

Olive leaves are naturally generated as a by-product during olive harvesting and olive oil production. Usually discarded with no specific use, they are a valuable source of bioactive compounds that should not be overlooked. Their valorization must therefore be achieved through the recovery [...] Read more.

Olive leaves are naturally generated as a by-product during olive harvesting and olive oil production. Usually discarded with no specific use, they are a valuable source of bioactive compounds that should not be overlooked. Their valorization must therefore be achieved through the recovery of their polyphenols using an ecological strategy. Conventional extraction is commonly known as an energy- and solvent-consuming process, whereas emerging and innovative extraction technologies, such as ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE), pulsed-electric-field-assisted extraction (PEF), high-voltage-electric-discharge-assisted extraction (HVED), supercritical fluid extraction (SFE), infrared-assisted extraction (IAE), and “Intensification of Vaporization by Decompression to the Vacuum” (IVDV), are considered more sustainable and environmentally friendly. The aim of this review is to provide a comprehensive and updated overview of the valorization of olive leaves through both pretreatment and extraction techniques via an analysis of the recovered polyphenols and their potential applications. Full article

(This article belongs to the Special Issue Extraction and Analysis of Chemical Compositions of Natural Products and Plants)

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