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Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques

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A special issue of Separations (ISSN 2297-8739). This special issue belongs to the section "Analysis of Natural Products and Pharmaceuticals".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 17153

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Dr. Faiyaz Shakeel

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Department of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Interests: HPTLC; HPLC, nanotechnology; GC-MS; pharmaceutical analysis; phytochemical analysis
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

A growing tendency toward the discovery and use of natural bioactive compounds that are the least harmful, have the fewest side effects, and fit the human body the most naturally has been seen over the past few decades. As evidenced by the rise in recent studies on the therapeutic properties of plants, this trend has caused a return of healthcare professionals to nature and plants, but with a modern approach that specifically questions how plants help to heal humans and what their exact effects on the human body are. The medicinal properties of plants are related to their phytochemical makeup, which is a complex matrix with a large number of naturally occurring bioactive molecules that must be distinguished in order to be identified. The separation of natural bioactive chemicals from plants can be accomplished utilizing cutting-edge, high-tech, hyphenated chromatographic approaches, which also give us a ton of information to be able to identify compounds. In order to explain a plant's mechanism of action and therapeutic effect, modern healthcare providers need to be able to link the phytochemical profile of a plant employed in therapy to a biological activity. In addition to plants, natural bioactive substances can be found in a variety of foods and pharmaceuticals. As a result, it is crucial to analyze these chemicals in plant, food, and pharmaceutical products. In order to identify and analyze natural bioactive compounds in plant, food, and pharmaceutical products, this Special Issue attempts to compile the latest improvements, advancements, and analytical innovations in chromatographic techniques. Additionally, we seek to enable researchers to link the phytochemical profiles of plants, foods, and pharmaceuticals with proven therapeutic effects, which may later substantiate the health-related claims made for these products.

Dr. Faiyaz Shakeel
Guest Editor

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Keywords

phytochemical analysis
food composition analysis
pharmaceutical analysis
gas chromatography mass spectrometry
liquid chromatography mass spectrometry
high-performance thin-layer chromatography
high-performance liquid chromatography
ultra-high performance liquid chromatography
supercritical fluid chromatography

Published Papers (11 papers)

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Editorial

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4 pages, 192 KiB

Open AccessEditorial

Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques

by Faiyaz Shakeel

Separations 2023, 10(10), 541; https://doi.org/10.3390/separations10100541 - 13 Oct 2023

Viewed by 1192

Abstract

A growing tendency toward the discovery and use of natural bioactive compounds that are the least harmful, have the fewest side effects, and are the most natural for the human body has been noticed during the past few decades [...] Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

Research

Jump to: Editorial

11 pages, 1854 KiB

Open AccessArticle

Rapid and Simultaneous Extraction of Bisabolol and Flavonoids from Gymnosperma glutinosum and Their Potential Use as Cosmetic Ingredients

by Mayra Beatriz Gómez-Patiño, Juan Pablo Leyva Pérez, Marcia Marisol Alcibar Muñoz, Israel Arzate-Vázquez and Daniel Arrieta-Baez

Separations 2023, 10(7), 406; https://doi.org/10.3390/separations10070406 - 14 Jul 2023

Cited by 1 | Viewed by 1157

Abstract

Gymnosperma glutinosum is a plant popularly known as “popote”, “tatalencho”, “tezozotla” or “pegajosa”, and it is used in traditional medicine in the region of Tehuacán, Puebla (Mexico), for the treatment of jiotes and acne and to cure diarrhea using the aerial parts in infusions. To analyze the phytochemical composition, we have developed a rapid protocol for the extraction and separation of the components of the aerial parts of G. glutinosum. After a maceration process, chloroformic and methanolic extracts were obtained and analyzed. Extracts were evaluated by GC-MS (gas chromatography-mass spectrometry), and their composition revealed the presence of (−)-α-bisabolol (BIS) as the main component in the chloroformic extract, which was isolated and analyzed by ¹H NMR to confirm its presence in the plant. The analysis of methanolic extracts by UPLC-MS (ultra-performance liquid chromatography-mass spectrometry) revealed the occurrence of six methoxylated flavones with m/z 405.08 (C₁₉H₁₈O₁₀), m/z 419.09 (C₂₀H₂₀O₁₀) and m/z 433.11 (C₂₁H₂₂O₁₀), and a group of C20-, C18-hydroxy-fatty acids, which give the plant its sticky characteristic. The presence of BIS, an important sesquiterpene with therapeutic skin effects, as well as some antioxidant compounds such as methoxylated flavones and their oils, could play an important role in cosmetology and dermatology formulations. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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16 pages, 2404 KiB

Open AccessArticle

Fractions of Methanol Extracts from the Resurrection Plant Haberlea rhodopensis Have Anti-Breast Cancer Effects in Model Cell Systems

by Diana Zasheva, Petko Mladenov, Krasimir Rusanov, Svetlana Simova, Silvina Zapryanova, Lyudmila Simova-Stoilova, Daniela Moyankova and Dimitar Djilianov

Separations 2023, 10(7), 388; https://doi.org/10.3390/separations10070388 - 01 Jul 2023

Cited by 3 | Viewed by 1291

Abstract

Breast cancer is among the most problematic diseases and a leading cause of death in women. The methods of therapy widely used, so far, are often with many side effects, seriously hampering patients’ quality of life. To overcome these constraints, new cancer treatment alternatives are constantly tested, including bioactive compounds of plant origin. Our aim was to study the effects of Haberlea rhodopensis methanol extract fractions on cell viability and proliferation of two model breast cancer cell lines with different characteristics. In addition to the strong reduction in cell viability, two of the fractions showed significant influence on the proliferation rate of the hormone receptor expressing MCF7 and the triple negative MDA-MB231 breast cancer cell lines. No significant effects on the benign MCF10A cell line were observed. We applied a large scale non-targeted approach to purify and identify highly abundant compounds from the active fractions of H. rhodopensis extracts. By the combined NMR/MS approach, myconoside was identified in the fractions and hispidulin 8-C-(6-O-acetyl-2″-O-syringoyl-β-glucopyranoside) was found in one of them. We further performed molecular docking analysis of possible myconoside interactions with several proteins, important for breast cancer proliferation. High probability of binding was established for GLUT1 transporter, estrogen receptor and MYST acetyltransferase. Our results are a good background for future studies on the use of myconoside for targeted breast cancer therapy. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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17 pages, 3698 KiB

Open AccessArticle

Impact and Optimization of the Conditions of Extraction of Phenolic Compounds and Antioxidant Activity of Olive Leaves (Moroccan picholine) Using Response Surface Methodology

by El Mustapha El Adnany, Najat Elhadiri, Ayoub Mourjane, Mourad Ouhammou, Nadia Hidar, Abderrahim Jaouad, Khalid Bitar and Mostafa Mahrouz

Separations 2023, 10(6), 326; https://doi.org/10.3390/separations10060326 - 25 May 2023

Cited by 4 | Viewed by 1069

Abstract

The Moroccan picholine tree’s leaves contain phenolic compounds that benefit human health. However, the amount and type of these compounds can vary based on factors such as the extraction method and conditions. This study aimed to improve phenolic compounds’ extraction while minimising harmful chemicals’ use. It has been found that using ethanol as a solvent with ultrasonic extraction is the most effective and environmentally friendly technique. Several parameters, such as the extraction time, solid/solvent ratio, and ethanol concentration as independent variables, were evaluated using a surface response method (RSM) based on the Box–Behnken design (BBD) to optimize the extraction conditions. The experimental data were fitted to a second-order polynomial equation using multiple regression analysis and also examined using the appropriate statistical methods. In optimal conditions, the ultrasonic time, the ratio (solvent/solid) and the concentration (ethanol/water), the content of total polyphenols (TPC), total flavonoids (TFC), and antioxidant activity (by DPPH, ABTS, FRAP) were, respectively, 74.45 ± 1.22 mg EAG/g DM, 17.08 ± 1.85 mg EC/g DM, 83.45 ± 0.89% 82.85 ± 1.52%, and 85.01 ± 2.35%. The identification of phenolic compounds by chromatography coupled with mass spectrum (HPLC-MS) under optimal conditions with two successive extractions showed the presence of hydroxytyrosol, catechin, caffeic acid, vanillin, naringin, oleuropein, quercetin, and kaempferol at high concentrations. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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13 pages, 1524 KiB

Open AccessArticle

Evaluation of Chinese Prickly Ash and Cinnamon to Mitigate Heterocyclic Aromatic Amines in Superheated Steam-Light Wave Roasted Lamb Meat Patties Using QuEChERS Method Coupled with UPLC-MS/MS

by Raheel Suleman, Muawuz Ijaz, Huan Liu, Alma D. Alarcon-Rojo, Zhenyu Wang and Dequan Zhang

Separations 2023, 10(6), 323; https://doi.org/10.3390/separations10060323 - 25 May 2023

Cited by 2 | Viewed by 994

Abstract

Chinese prickly ash and cinnamon contain many antioxidants, which scavenge free radicals and can reduce many harmful compounds, such as heterocyclic aromatic amines (HAAs). Modern technologies used for cooking, such as the use of superheated steam roasting, are beneficial in decreasing the development of HAAs. The current study was based on the use of these two spices in roasted lamb patties to mitigate the formation of HAAs in superheated steam roasted patties. Results exhibited significant differences (p < 0.05) in the content of both polar and non-polar HAAs as compared to control patties. In cinnamon roasted patties, polar HAAs were reduced from 23.76 to 10.56 ng g⁻¹, and non-polar HAAs were reduced from 21.34 to 15.47 ng g⁻¹. In Chinese prickly ash patties, polar and non-polar HAAs were 43.60 ng g⁻¹ and 35.74 ng g⁻¹, respectively. Similarly, cinnamon-treated patties showed a significantly higher (p < 0.05) reduction in polar HAAs (23.52 to 12.41 ng g⁻¹) than non-polar (16.08 to 9.51 ng g⁻¹) at concentrations of 0.5–1.5%, respectively, as compared to the control, with 45.81 ng g⁻¹ polar and 35.09 ng g⁻¹ non-polar HAAs. The polar HAAs tested were PhIP, DMIP, IQx, and 8-MeIQx, while the non-polar were harman and norharman. Both spices and superheated steam controlled HAAs to a significant level in lamb meat patties. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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11 pages, 614 KiB

Open AccessArticle

Determination of Pterostilbene in Pharmaceutical Products Using a New HPLC Method and Its Application to Solubility and Stability Samples

by Nazrul Haq, Faiyaz Shakeel, Mohammed M. Ghoneim, Syed Mohammed Basheeruddin Asdaq, Prawez Alam, Fahad Obaid Aloatibi and Sultan Alshehri

Separations 2023, 10(3), 178; https://doi.org/10.3390/separations10030178 - 07 Mar 2023

Cited by 2 | Viewed by 1693

Abstract

The quantification of a natural bioactive compound, pterostilbene (PTT), in commercial capsule dosage form, solubility, and stability samples was carried out using a rapid and sensitive high-performance liquid chromatography (HPLC) approach. PTT was quantified on a Nucleodur (150 mm × 4.6 mm) RP C₁₈ column with a particle size of 5 µm. Acetonitrile and water (90:10 v/v) made up the mobile phase, which was pumped at a flow speed of 1.0 mL/min. At a wavelength of 254 nm, PTT was detected. The developed HPLC approach was linear in 1–75 µg/g range, with a determination coefficient of 0.9995. The developed HPLC approach for PTT estimation was also rapid (R_t = 2.54 min), accurate (%recoveries = 98.10–101.93), precise (%CV = 0.59–1.25), and sensitive (LOD = 2.65 ng/g and LOQ = 7.95 ng/g). The applicability of developed HPLC approach was revealed by determining PTT in commercial capsule dosage form, solubility, and stability samples. The % assay of PTT in marketed capsules was determined to be 99.31%. The solubility of PTT in five different green solvents, including water, propylene glycol, ethanol, polyethylene glycol-400, and Carbitol was found to be 0.0180 mg/g, 1127 mg/g, 710.0 mg/g, 340.0 mg/g, and 571.0 mg/g, respectively. In addition, the precision and accuracy of stability samples were within the acceptable limit, hence PTT was found to be stable in solution. These results suggested that PTT in commercial products, solubility, and stability samples may be routinely determined using the established HPLC method. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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12 pages, 1584 KiB

Open AccessArticle

UPLC-MS/MS Method for Simultaneous Estimation of Neratinib and Naringenin in Rat Plasma: Greenness Assessment and Application to Therapeutic Drug Monitoring

by Ali Altharawi, Safar M. Alqahtani, Sagar Suman Panda, Majed Alrobaian, Alhumaidi B. Alabbas, Waleed Hassan Almalki, Manal A. Alossaimi, Md. Abul Barkat, Rehan Abdur Rub, Shehla Nasar Mir Najib Ullah, Mahfoozur Rahman and Sarwar Beg

Separations 2023, 10(3), 167; https://doi.org/10.3390/separations10030167 - 01 Mar 2023

Cited by 1 | Viewed by 1520

Abstract

Tyrosine kinase inhibitors have often been reported to treat early-stage hormone-receptor-positive breast cancers. In particular, neratinib has shown positive responses in stage I and II cases in women with HER2-positive breast cancers with trastuzumab. In order to augment the biopharmaceutical attributes of the drug, the work designed endeavors to explore the therapeutic benefits of neratinib in combination with naringenin, a phytoconstituent with reported uses in breast cancer. A UPLC-MS/MS method was developed for the simultaneous estimation of neratinib and naringenin in rat plasma, while imatinib was selected as the internal standard (IS). Acetonitrile was used as the liquid extractant. The reversed-phase separation was achieved on a C18 column (100 mm × 2.1 mm, 1.7 µm) with the isocratic flow of mobile phase-containing acetonitrile (0.1% formic acid) and 0.002 M ammonium acetate (50:50, % v/v) at flow rate 0.5 mL·min⁻¹. The mass spectra were recorded by multiple reaction monitoring of the precursor-to-product ion transitions for neratinib (m/z 557.138→111.927), naringenin (m/z 273.115→152.954), and the IS (m/z 494.24→394.11). The method was validated for selectivity, trueness, precision, matrix effect, recovery, and stability over a concentration range of 10–1280 ng·mL⁻¹ for both targets and was acceptable. The method was also assessed for greenness profile by an integrative qualitative and quantitative approach; the results corroborated the eco-friendly nature of the method. Therefore, the developed method has implications for its applicability in clinical sample analysis from pharmacokinetic studies in human studies to support the therapeutic drug monitoring (TDM) of combination drugs. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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10 pages, 1455 KiB

Open AccessArticle

Analysis of Sugars in Honey Samples by Capillary Zone Electrophoresis Using Fluorescence Detection

by Melinda Andrasi, Gyongyi Gyemant, Zsofi Sajtos and Cynthia Nagy

Separations 2023, 10(3), 150; https://doi.org/10.3390/separations10030150 - 23 Feb 2023

Cited by 2 | Viewed by 1918

Abstract

The applicability of capillary electrophoresis (CE) with light-emitting diode-induced fluorescence detection (LEDIF) for the separation of sugars in honey samples was studied. An amount of 25 mM ammonium acetate (pH 4.5) with 0.3% polyethylene oxide (PEO) was found to be optimal for the efficient separation of carbohydrates. 8-aminopyrene-1,3,6-trisulfonic acid (APTS) was used for the labeling of the carbohydrate standards and honey sugars for fluorescence detection. The optimized method was applied in the quantitative analysis of fructose and glucose by direct injection of honey samples. Apart from the labeling reaction, no other sample preparation was performed. The mean values of the fructose/glucose ratio for phacelia honey, acacia honey and honeydew honey were 0.86, 1.61 and 1.42, respectively. The proposed method provides high separation efficiency and sensitive detection within a short analysis time. Apart from the labeling reaction, it enables the injection of honeys without sample pretreatment. This is the first time that fluorescence detection has been applied for the CE analysis of sugars in honeys. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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15 pages, 1987 KiB

Open AccessArticle

Greener Stability-Indicating HPLC Approach for the Determination of Curcumin in In-House Developed Nanoemulsion and Curcuma longa L. Extract

by Nazrul Haq, Faiyaz Shakeel, Mohammed M. Ghoneim, Syed Mohammed Basheeruddin Asdaq, Prawez Alam, Saleh A. Alanazi and Sultan Alshehri

Separations 2023, 10(2), 98; https://doi.org/10.3390/separations10020098 - 01 Feb 2023

Cited by 3 | Viewed by 1495

Abstract

Despite the fact that several analytical methodologies have been reported for the determination of curcumin (CCM) in a wide range of sample matrices, the greener liquid chromatographic approaches to determine CCM are scarce in the literature. Therefore, this research is designed to develop and validate a greener stability-indicating “high-performance liquid chromatography (HPLC)” methodology to determine CCM in an in-house developed nanoemulsion, Curcuma longa L. extract, and commercial tablets. CCM was measured on a Nucleodur (150 mm × 4.6 mm) RP C₁₈ column with 5 µm-sized particles. Ethanol and ethyl acetate (83:17 v/v) made up the greener eluent system, which was pumped at a flow speed of 1.0 mL/min. At a wavelength of 425 nm, CCM was detected. The greener HPLC methodology was linear in the 1–100 µg/mL range, with a determination coefficient of 0.9983. The greener HPLC methodology for CCM estimation was also rapid (R_t = 3.57 min), accurate (%recoveries = 98.90–101.85), precise (%CV = 0.90–1.11), and sensitive (LOD = 0.39 µg/mL and LOQ = 1.17 µg/mL). The AGREE approach predicted the AGREE score of 0.81 for the established HPLC technique, indicating an outstanding greenness profile. The utility of the greener HPLC methodology was demonstrated by determining CCM in the in-house developed nanoemulsion, Curcuma longa extract, and commercial tablets. The % amount of CCM in the in-house developed nanoemulsion, Curcuma longa extract, and commercial tablets was found to be 101.24%, 81.15%, and 78.41%, respectively. The greener HPLC methodology was able to detect its degradation product under various stress conditions, suggesting its stability-indication characteristics. These results suggested that CCM in developed nanoemulsion, plant extract samples, and commercial tablets may be routinely determined using the greener HPLC methodology. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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15 pages, 1241 KiB

Open AccessArticle

Cytotoxic, Scolicidal, and Insecticidal Activities of Lavandula stoechas Essential Oil

by Abdel-Azeem S. Abdel-Baki, Shawky M. Aboelhadid, Saleh Al-Quraishy, Ahmed O. Hassan, Dimitra Daferera, Atalay Sokmen and Asmaa A. Kamel

Separations 2023, 10(2), 100; https://doi.org/10.3390/separations10020100 - 01 Feb 2023

Cited by 1 | Viewed by 1689

Abstract

Essential oils (EOs) have recently attracted more interest due to their insecticidal activities, low harmfulness, and rapid degradation in the environment. Therefore, Lavandula steochas (L. steochas) essential oil was assessed for its chemical constituents, in vitro cytotoxicity, and scolicidal, acaricidal, and insecticidal activities. Using spectrometry and gas chromatography, the components of L. steochas EOs were detected. Additionally, different oil concentrations were tested for their anticancer activities when applied to human embryonic kidney cells (HEK-293 cells) and the human breast cancer cell line MCF-7. The oil’s scolicidal activity against protoscolices of hydatid cysts was evaluated at various concentrations and exposure times. The oil’s adulticidal, larvicidal, and repelling effects on R. annulatus ticks were also investigated at various concentrations, ranging from 0.625 to 10%. Likewise, the larvicidal and pupicidal activities of L. steochas against Musca domestica were estimated at different concentrations. The analyses of L. steochas oil identified camphor as the predominant compound (58.38%). L. steochas oil showed significant cytotoxicity against cancer cells. All of the tested oil concentrations demonstrated significant scolicidal activities against the protoscoleces of hydatid cysts. L. steochas EO (essential oil) showed 100% adulticidal activity against R. annulatus at a 10% concentration with an LC₅₀ of 2.34%, whereas the larvicidal activity was 86.67% and the LC₅₀ was 9.11%. On the other hand, the oil showed no repellent activity against this tick’s larva. Furthermore, L. steochas EO achieved 100% larvicidal and pupicidal effects against M. domestica at a 10% concentration with LC₅₀ values of 1.79% and 1.51%, respectively. In conclusion, the current work suggests that L. steochas EO could serve as a potential source of scolicidal, acaricidal, insecticidal, and anticancer agents. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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11 pages, 2062 KiB

Open AccessArticle

GC-MS Analysis, Phytochemical Screening, and Antibacterial Activity of Cerana indica Propolis from Kashmir Region

by Ishfaq Mohiuddin, T. Ramesh Kumar, Mohammed Iqbal Zargar, Shahid Ud Din Wani, Wael A. Mahdi, Sultan Alshehri, Prawez Alam and Faiyaz Shakeel

Separations 2022, 9(11), 363; https://doi.org/10.3390/separations9110363 - 09 Nov 2022

Cited by 6 | Viewed by 2268

Abstract

Propolis is a resinous compound produced by honey bees. It contains bioactive molecules that possess a wide range of biological functions. The chemical composition of propolis is affected by various variables, including the vegetation, the season, and the area from which the sample was collected. The aim of this study was to analyze the chemical composition and assess Cerana indica propoli’s antibacterial efficacy from the Kashmir region. Gas chromatography-mass spectrometry (GC-MS) analysis was used to determine the chemical composition of Kashmiri propolis. A range of bacterial strains was tested for antimicrobial activity using different extracts of propolis by agar well diffusion technique. Propolis was found to be rich in alkaloids, saponins, tannins, and resins. The chemical characterization revealed the presence of 68 distinct phytocompounds using GC-MS, and the most predominant compounds were alpha-D-mannopyranoside, methyl, cyclic 2,3:4,6-bis-ethyl boronate (21.17%), followed by hexadecanoic acid, methyl ester (9.91%), and bacteriochlorophyll-c-stearyl (4.41%). The different extracts of propolis showed specific antibacterial efficacy against multidrug-resistant (MDR) strains viz., Pseudomonas aeruginosa (MTCC1688), Escherichiacoli (MTCC443), Klebsiella pneumonia (MTCC19), Cutibacterium acnes (MTCC843), and Staphylococcus aureus (MTCC96). The EEKP showed the highest zone of inhibition against S. aureus (17.33) at 400 µg mL⁻¹. According to the findings of this study, bee propolis contains a variety of secondary metabolites with various pharmacological activities. Furthermore, because of its broad spectrum of positive pharmacological actions and the fact that it is a promising antibacterial agent, more research on propolis is warranted. Full article

(This article belongs to the Special Issue Analysis of Natural Bioactive Compounds in Plant, Food, and Pharmaceutical Products Using Chromatographic Techniques)

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