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Extraction and Analysis of New Bioactive Compounds Derived from Natural Products

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 27541

Special Issue Editors

Dr. Irinel Adriana Badea

E-Mail Website
Guest Editor
Department of Analytical Chemistry and Physical Chemistry, Faculty of Chemistry, University of Bucharest, 030018 Bucharest, Romania
Interests: separation sciences; HPLC; HPLC-MS; GC-MS; spectrometry; NMR; IR; pharmaceutical analysis; electrochemistry
Special Issues, Collections and Topics in MDPI journals
Dr. Rodica Olar

E-Mail Website
Guest Editor
Department of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 050663 Bucharest, Romania
Interests: coordination chemistry; biological active species (organic and inorganic); characterization methods (ESI-MS, NMR, IR, EPR)
Special Issues, Collections and Topics in MDPI journals
Dr. Magdalena Mititelu

E-Mail Website
Guest Editor
Department of Clinical Laboratory and Food Safety, Faculty of Pharmacy, Carol Davila University of Medicine and Pharmacy, 020956 Bucharest, Romania
Interests: nutrition; food safety; food technology; biotechnology; pharmaceutical research and development; dosage form development; pharmaceutical analysis; clinical biochemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural products have been used for a very long time as food supplements and drugs. To date, according to the WHO, more than 80% of countries have developed treatments based on traditional medicine, which employs phytochemical compounds, and almost 70000 species have been tested for their biological properties. These studies reveal the huge advantage of using compounds derived from natural products, relying on their safety and broad efficiency to treat diseases. Thus, they present real competition to synthetic molecules.

Under these circumstances, the assessment of new compounds from natural products derived from terrestrial or marine plants and animals represents a continuous area of interest. Thus, new extraction and analytical methodologies that fit the requirement of green chemistry should be encouraged in order to obtain not only valuable extracts, but, most importantly, standardized ones. Despite the rewarding utilization of these natural products, the interest in them has decreased in recent years; therefore, it is high time that this field was revitalized.

Thus, this Special Issue will be devoted to the extraction and analysis of new bioactive compounds derived from natural products.

Dr. Irinel Adriana Badea
Dr. Rodica Olar
Dr. Magdalena Mititelu
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • phytochemicals
  • natural products
  • traditional medicine
  • liquid–liquid extraction
  • hydro distillation and steam distillation
  • solid-phase extraction
  • soxhlet extraction
  • pressurized liquid extraction
  • supercritical fluid extraction
  • ultrasound-assisted extraction
  • microwave-assisted extraction
  • enzyme-assisted extraction
  • pulsed electric field extraction
  • HPLC/HPLC–MS/GC–MS/NMR/IR
  • in vitro assay
  • in vivo assay
  • antioxidant/anti-inflammatory/antimicrobial/antitumoral activity

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Published Papers (18 papers)

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11 pages, 1667 KiB  
Article
Six New Compounds from the Herbaceous Stems of Ephedra intermedia Schrenket C. A. Meyer and Their Lung-Protective Activity
by Xiling Fan, Yangang Cao, Mengnan Zeng, Yingjie Ren, Xiaoke Zheng and Weisheng Feng
Molecules 2024, 29(2), 432; https://doi.org/10.3390/molecules29020432 - 16 Jan 2024
Viewed by 683
Abstract
Six new compounds, (7R,8S,8′R)-balanophorone (1), (7′S,8′R,8R)-yunnanensin A (2), (3S)-thunberginol C (3), (8R,8′R)-maninsigin B (4), (7S,8 [...] Read more.
Six new compounds, (7R,8S,8′R)-balanophorone (1), (7′S,8′R,8R)-yunnanensin A (2), (3S)-thunberginol C (3), (8R,8′R)-maninsigin B (4), (7S,8R)-4,7,8-dihydroxy-9,9-dimethyl-chroman (5), and 4-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butan-1-one (6), along with eight known compounds (7–14), were isolated from the herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer. Their structures were elucidated based on their spectroscopic (MS, NMR, IR, and UV) data, and their absolute configurations were determined by comparing their calculated and experimental electronic circular dichroic (ECD) spectra. Moreover, compounds 1 and 3–6 were evaluated for their ability to protect human pulmonary epithelial cells (BEAS-2B) from injury induced by lipopolysaccharide (LPS) in vitro. The results showed that compound 6 exhibited a significant protective effect against LPS-induced injury in BEAS-2B, and compound 5 exhibited a slightly protective effect at the concentration of 10 μM. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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27 pages, 5859 KiB  
Article
HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds
by Mohammed Lamine Khenifi, Talia Serseg, Piotr Migas, Mirosława Krauze-Baranowska, Sadin Özdemir, Chawki Bensouici, Mohammed I. Alghonaim, Khattab Al-Khafaji, Sulaiman A. Alsalamah, Messaoud Boudjeniba, Mohamed Yousfi, Fehmi Boufahja, Hamdi Bendif and Mohamed Mahdid
Molecules 2023, 28(23), 7798; https://doi.org/10.3390/molecules28237798 - 27 Nov 2023
Viewed by 1271
Abstract
Fenugreek (Trigonella foenum-graecum) has a great beneficial health effect; it has been used in traditional medicine by many cultures. Likewise, the α-amylase inhibitors are potential compounds in the development of drugs for the treatment of diabetes. The beneficial health effects of [...] Read more.
Fenugreek (Trigonella foenum-graecum) has a great beneficial health effect; it has been used in traditional medicine by many cultures. Likewise, the α-amylase inhibitors are potential compounds in the development of drugs for the treatment of diabetes. The beneficial health effects of fenugreek lead us to explore the chemical composition of the seeds and their antioxidant and α-amylase inhibition activities. The flavonoid extraction from fenugreek seeds was achieved with methanol through a Soxhlet apparatus. Then, the flavonoid glycosides were characterized using HPLC-DAD-ESI-MS analysis. The antioxidant capacity of fenugreek seed was measured using DPPH, FRAP, ABTS, and CUPRAC assays. Finally, the α-amylase inhibition activity was carried out using in vitro and in silico methods. The methanolic extract was found to contain high amounts of total phenolics (154.68 ± 1.50 μg GAE/mg E), flavonoids (37.69 ± 0.73 μg QE/mg E). The highest radical-scavenging ability was recorded for the methanolic extract against DPPH (IC50 = 556.6 ± 9.87 μg/mL), ABTS (IC50 = 593.62 ± 9.35 μg/mL). The ME had the best reducing power according to the CUPRAC (A 0.5 = 451.90 ± 9.07 μg/mL). The results indicate that the methanolic extracts of fenugreek seed best α-amylase inhibition activities IC50 = 653.52 ± 3.24 μg/mL. Twenty-seven flavonoids were detected, and all studied flavonoids selected have good affinity and stabilize very well in the pocket of α-amylase. The interactions between the studied flavonoids with α-amylase were investigated. The flavonoids from fenugreek seed present a good inhibitory effect against α-amylase, which is beneficial for the prevention of diabetes and its complications. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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19 pages, 642 KiB  
Article
Superior Valorisation of Juglans regia L. Leaves of Different Maturity through the Isolation of Bioactive Compounds
by Mihaela Tociu, Fulvia Manolache, Brîndușa Bălănucă, Alina Moroșan and Raluca Stan
Molecules 2023, 28(21), 7328; https://doi.org/10.3390/molecules28217328 - 29 Oct 2023
Cited by 1 | Viewed by 795
Abstract
Extracts rich in bioactive compounds from natural sources have received great interest due to their great impact on human health. The aim of this research is focused on the obtaining and characterization of several extracts from Juglans regia L. leaves in four different [...] Read more.
Extracts rich in bioactive compounds from natural sources have received great interest due to their great impact on human health. The aim of this research is focused on the obtaining and characterization of several extracts from Juglans regia L. leaves in four different maturity phases: young green leaves (YGL), green leaves (GL), mature green leaves (MGL), and yellow leaves (YL), using different solvents: ethanol (e), water (w), or water:ethanol (1:1 (v/v)—m) by employing several methods: magnetic stirring (MS), ultrasound-assisted (UA), as well as maceration (M). The obtained extracts were quantitatively evaluated through spectrophotometric methods: Total Polyphenol Content (TPC-Folin–Ciocalteu assay) and Total Antioxidant Capacity (TEAC assay). Phytochemical screening by means of Fourier-Transform Ion–Cyclotron-Resonance High-Resolution Mass Spectrometry (FT-ICR-MS) indicated the presence of 40 compounds belonging to different phytochemical classes: phenolic acids, flavonoids, flavones, flavanones, flavonones, flavanols, vitamins, tereponoid, steroid, anthocyanidin, and other compounds. Based on TPC and TEAC assays, the water-ethanol mixture was found to be the proper extraction solvent, with the best results being obtained for YL plant material: 146.29 mg GAE/g DM (TPC) and 11.67 mM TE/g DM (TEAC). This type of extract may be used in various domains, such as the cosmetics industry, the biomedical field, and/or the design of functional foods, relying on their phytochemical composition. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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22 pages, 14813 KiB  
Article
Peculiarities of the Variation of Biologically Active Compounds in Fruit of Vaccinium oxycoccos L. Growing in the Čepkeliai State Strict Nature Reserve
by Rima Šedbarė, Onutė Grigaitė and Valdimaras Janulis
Molecules 2023, 28(15), 5888; https://doi.org/10.3390/molecules28155888 - 5 Aug 2023
Viewed by 751
Abstract
This study was carried out to analyze the accumulation patterns of anthocyanins, proanthocyanidins, flavonols, chlorogenic acid, and triterpene compounds in fruit samples of Vaccinium oxycoccos L. berries growing in the Čepkeliai State Strict Nature Reserve in Lithuania. Studies were carried out on the [...] Read more.
This study was carried out to analyze the accumulation patterns of anthocyanins, proanthocyanidins, flavonols, chlorogenic acid, and triterpene compounds in fruit samples of Vaccinium oxycoccos L. berries growing in the Čepkeliai State Strict Nature Reserve in Lithuania. Studies were carried out on the phytochemical composition of cranberry fruit samples during the period of 2020–2022. Anthocyanins, flavonols, chlorogenic acid and triterpene compounds were identified and quantified using UPLC-DAD methods, and proanthocyanins were determined using spectrophotometric methods. The content of identified compounds varied, as reflected in the total amounts of anthocyanins (710.3 ± 40 µg/g to 6993.8 ± 119 µg/g), proanthocyanidins (378.4 ± 10 µg EE/g to 3557. 3 ± 75 µg EE/g), flavonols (479.6 ± 9 µg/g to 7291.2 ± 226 µg/g), chlorogenic acid (68.0 ± 1 µg/g to 3858.2 ± 119 µg/g), and triterpenoids (3780.8 ± 98 µg/g to 7226.9 ± 224 µg/g). Cranberry fruit samples harvested from open oligotrophic wetland habitats contained higher levels of anthocyanins, anthocyanidins, flavonol glycosides, and proanthocyanidins. The highest levels of triterpene compounds were found in the cranberry fruits harvested in the spring of the following year after the snowmelt. The use of principal component analysis showed that cranberry plant material harvested in October and November had higher levels of bioactive compounds. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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11 pages, 1484 KiB  
Article
Determination of Active Ingredients, Mineral Composition and Antioxidant Properties of Hydroalcoholic Macerates of Vinca minor L. Plant from the Dobrogea Area
by Ana-Maria Neculai, Gabriela Stanciu and Magdalena Mititelu
Molecules 2023, 28(15), 5667; https://doi.org/10.3390/molecules28155667 - 26 Jul 2023
Cited by 2 | Viewed by 1207
Abstract
In recent decades, new alternative therapies using drugs containing active ingredients of natural origin have been a hot topic for medical research. Based on the confirmed therapeutic potential of the Vinca minor plant, considered in the specialized literature to be of pharmaceutical interest, [...] Read more.
In recent decades, new alternative therapies using drugs containing active ingredients of natural origin have been a hot topic for medical research. Based on the confirmed therapeutic potential of the Vinca minor plant, considered in the specialized literature to be of pharmaceutical interest, the purpose of this study is to determine the chemical and mineral composition of the Vinca minor plant grown in the Dobrogea area, with a view to its use in the formulation of dermal preparations. For this purpose, plant materials were collected from the mentioned area and hydroalcoholic macerates of different concentrations were obtained: 40%, 70% and 96% from leaves (F40, F70, F96) and stems (T40, T70, T96) of Vinca minor plant to determine the optimal extraction solvent. The hydroalcoholic macerates were analyzed via the HPLC method for the identification and quantification of the main bioactive compounds, and two methods were used to evaluate their antioxidant properties: the DPPH radical scavenging test and the photochemiluminescence method. HPLC analysis showed the presence of four indole alkaloids: vincamine, 1,2-dehydroaspidospermidine, vincaminoreine and eburnamonine. Vincamine was the alkaloid found in the highest concentration in Vinca leaves (2.459 ± 0.035 mg/100 g d.w.). The antioxidant activity of Vinca minor hydroalcoholic macerates showed values between 737.626–1123.500 mg GAE/100 g d.w (DPPH test) and 77.439–187.817 mg TE/100 g d.w (photochemiluminescence method). The concentrations of toxic metals Cd, Cu, Ni, Pb in dried leaves and stems of Vinca minor, determined by AAS, were below detection limits. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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20 pages, 7283 KiB  
Article
Exploration and Evaluation of Secondary Metabolites from Trichoderma harzianum: GC-MS Analysis, Phytochemical Profiling, Antifungal and Antioxidant Activity Assessment
by Wassima Lakhdari, Ibtissem Benyahia, Mustapha Mounir Bouhenna, Hamdi Bendif, Hafida Khelafi, Hakim Bachir, Amel Ladjal, Hamida Hammi, Dajwahir Mouhoubi, Hanane Khelil, Taghrid S. Alomar, Najla AlMasoud, Nabil Boufafa, Fehmi Boufahja and Abderrahmene Dehliz
Molecules 2023, 28(13), 5025; https://doi.org/10.3390/molecules28135025 - 27 Jun 2023
Cited by 4 | Viewed by 2414
Abstract
In this study, we investigated in vitro the potential of Trichoderma harzianum to produce bioactive secondary metabolites that can be used as alternatives to synthetic compounds. The study focused on analyzing two extracts of T. harzianum using ethyl acetate and n-butanol solvents [...] Read more.
In this study, we investigated in vitro the potential of Trichoderma harzianum to produce bioactive secondary metabolites that can be used as alternatives to synthetic compounds. The study focused on analyzing two extracts of T. harzianum using ethyl acetate and n-butanol solvents with different polarities. The extracts were examined using phytochemical analysis to determine the content of polyphenols, flavonoids, tannins, and alkaloids. Thin-layer chromatography (TLC) and Gas chromatography-mass spectroscopy (GC-MS) analysis were used to profile volatile organic metabolites (VOCs) present in the extracts. Furthermore, the extracts were tested for their antifungal ability using the poison food technique. For measuring antioxidant activity, the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) test was used. Trichoderma harzianum was shown to have a significantly high content of tannins and alkaloids, with a noticeable difference between the two extracts. GC-MS analysis identified 33 potential compounds with numerous benefits that could be used in agriculture and the medicinal industry. Moreover, strong antifungal activity was identified against Sclerotinia sclerotiorum by 94.44%, Alternaria sp. by 77.04%, and Fusarium solani by 51.48; similarly, the IC50 of antioxidant activity was estimated for ethyl acetate extract by 71.47% and n-butanol extract by 56.01%. This leads to the conclusion that Trichoderma harzianum VOCs play a significant role as an antifungal and antioxidant agent when taking into account the advantageous bioactive chemicals noted in the extracts. However, to our knowledge, this is the first study in Algeria presenting detailed phytochemical analysis and GC-MS profiling of Trichoderma harzianum for two extracts, ethyl acetate and n-butanol. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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13 pages, 528 KiB  
Article
Chemical Composition, Antioxidant Activity, and Antibacterial Activity of Black Poplar Buds’ Hydroalcoholic Macerates from Dobrogea Area
by Gabriela Stanciu, Florin Aonofriesei, Simona Lupsor, Elena Oancea and Magdalena Mititelu
Molecules 2023, 28(13), 4920; https://doi.org/10.3390/molecules28134920 - 22 Jun 2023
Cited by 3 | Viewed by 1276
Abstract
Black poplar buds have high contents of many compounds with therapeutic potential, which are useful in cosmetics and the treatment of various dermatitis, respiratory diseases, etc. The aim of this study was to identify and exploit the local plant resources with biologically active [...] Read more.
Black poplar buds have high contents of many compounds with therapeutic potential, which are useful in cosmetics and the treatment of various dermatitis, respiratory diseases, etc. The aim of this study was to identify and exploit the local plant resources with biologically active properties from the Dobrogea area, Romania. For this purpose, materials were collected from the mentioned area, and macerates of black poplar were prepared in order to evaluate their qualities as antioxidant and antimicrobial agents. Three different black poplar buds’ hydroalcoholic macerates were analyzed by the Folin–Ciocâlteau method to estimate the total content of phenolic compounds, by the HPLC-DAD method for identification and quantification of the main bioactive compounds and by the DPPH radical scavenging method to evaluate the antioxidant activity. All hydroalcoholic macerates showed high concentrations of phenolic compounds, the main individual compounds being gallic acid, chlorogenic acid, cinnamic acid, and methyl gallic acid. The antioxidant activity of the black poplar buds’ hydroalcoholic macerates, evaluated by the DPPH radical scavenging test, showed high values, between 496 and 1200 mg GAE /100 g d.w. The Cd, Cu, Zn, Ni, and Pb concentrations released in dry poplar buds, determined by AAS, were below the detection limits. Hydroalcoholic macerates of black poplar were tested against two groups of gram-positive bacteria (Enterococcus and Staphylococcus) using an agar well diffusion assay. The in vitro inhibitory activities of the macerates were important and ranged from 8.2–9.4 mm inhibition zones (Staphylococcus) to 8.6 −10 mm inhibition zones (Enterococcus). Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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14 pages, 1002 KiB  
Article
Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
by Antonio Cobo, Alfonso Alejo-Armijo, Daniel Cruz, Joaquín Altarejos, Sofía Salido and Elena Ortega-Morente
Molecules 2023, 28(12), 4844; https://doi.org/10.3390/molecules28124844 - 19 Jun 2023
Viewed by 1141
Abstract
Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with [...] Read more.
Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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22 pages, 12329 KiB  
Article
Mitigation of Hepatotoxicity via Boosting Antioxidants and Reducing Oxidative Stress and Inflammation in Carbendazim-Treated Rats Using Adiantum Capillus-Veneris L. Extract
by Mohamed Seif, Hanan Aati, May Amer, Arthur J. Ragauskas, Amr Seif, Ahmed H. El-Sappah, Abdulrahman Aati, Abd El-Nasser A. Madboli and Mahmoud Emam
Molecules 2023, 28(12), 4720; https://doi.org/10.3390/molecules28124720 - 12 Jun 2023
Viewed by 1342
Abstract
Exposure to food contaminants continues to be a substantial source of human health risks all over the world, particularly in developing countries. Carbendazim (CBZ) is a chemical fungicide used to control the spread of various fungi and other pathogens in the agriculture and [...] Read more.
Exposure to food contaminants continues to be a substantial source of human health risks all over the world, particularly in developing countries. Carbendazim (CBZ) is a chemical fungicide used to control the spread of various fungi and other pathogens in the agriculture and veterinary sectors. The hazardous effects of CBZ on human health occur due to the accumulation of its residues in agricultural food products. In this study, the possible hepatoprotective effects of Adiantum capillus-veneris L. (ACVL) extract were evaluated in CBZ-treated rats. A GC-MS analysis revealed that ACVL extract contained several bioactive hydrocarbon components and fatty acids, and that the components exerted hepatic protection by mitigating oxidative stress via upregulating antioxidant agents and neutralizing nitrogen and oxygen free radicals. Moreover, ACVL extracts relieved hepatic inflammation via decreasing NO, NF-κB, and pro-inflammatory cytokines (TNF-a, IL-6) in the liver of CBZ-treated rats, both at protein and mRNA levels. In addition, the protective effect of ACVL has appeared in the histopathological figures and function markers in the livers of CBZ-treated rats. According to the present results, ACVL extract can protect the hepatic tissue and restore its functions to a control level in CBZ-treated rats; this effect may be attributed to its antioxidant and anti-inflammatory activities. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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15 pages, 2419 KiB  
Article
Two New Cytotoxic Sesquiterpene-Amino Acid Conjugates and a Coumarin-Glucoside from Crossostephium chinense
by Zhichao Wang, Ben-Yeddy Abel Chitama, Keisuke Suganuma, Yoshi Yamano, Sachiko Sugimoto, Susumu Kawakami, Osamu Kaneko, Hideaki Otsuka and Katsuyoshi Matsunami
Molecules 2023, 28(12), 4696; https://doi.org/10.3390/molecules28124696 - 11 Jun 2023
Cited by 2 | Viewed by 1292
Abstract
The Asteraceae family is a promising source of bioactive compounds, such as the famous Asteraceae plants Tanacetum cinerariifolium (pyrethrin) and Artemisia annua (artemisinin). As a result of our series of phytochemical studies of the subtropical plants, two novel sesquiterpenes, named crossoseamines A and [...] Read more.
The Asteraceae family is a promising source of bioactive compounds, such as the famous Asteraceae plants Tanacetum cinerariifolium (pyrethrin) and Artemisia annua (artemisinin). As a result of our series of phytochemical studies of the subtropical plants, two novel sesquiterpenes, named crossoseamines A and B in this study (1 and 2, respectively), one undescribed coumarin-glucoside (3), and eighteen known compounds (4–21) were isolated from the aerial part of Crossostephium chinense (Asteraceae). The structures of isolated compounds were elucidated by spectroscopic methods, including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, HSQC, HMBC, and NOESY), IR spectrum, circular dichroism spectrum (CD), and high-resolution electrospray ionization–mass spectrometry (HR-ESI–MS). All isolated compounds were evaluated for their cytotoxic activities against Leishmania major, Plasmodium falciparum, Trypanosoma brucei (gambiense and rhodesiense), and human lung cancer cell line A549 because of the high demand for the discovery of new drug leads to overcome the present side effects and emerging drug-resistant strains. As a result, the new compounds (1 and 2) showed significant activities against A549 (IC50, 1: 3.3 ± 0.3; 2: 12.3 ± 1.0 μg/mL), L. major (IC50, 1: 6.9 ± 0.6; 2: 24.9 ± 2.2 μg/mL), and P. falciparum (IC50, 1: 12.1 ± 1.1; 2: 15.6 ± 1.2 μg/mL). Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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14 pages, 2501 KiB  
Article
In Vitro: The Effects of the Anticoccidial Activities of Calotropis procera Leaf Extracts on Eimeria stiedae Oocysts Isolated from Rabbits
by Mutee Murshed, Hossam M. A. Aljawdah, Mohammed Mares and Saleh Al-Quraishy
Molecules 2023, 28(8), 3352; https://doi.org/10.3390/molecules28083352 - 10 Apr 2023
Cited by 2 | Viewed by 1481
Abstract
Hepatic coccidiosis is an infectious and mortal disease that causes global economic losses in rabbits. The research aimed to assess the efficacy of Calotropis procure leaf extracts on the inhibition of Eimeria stiedae oocysts and to determine the optimal dosage for suppressing the [...] Read more.
Hepatic coccidiosis is an infectious and mortal disease that causes global economic losses in rabbits. The research aimed to assess the efficacy of Calotropis procure leaf extracts on the inhibition of Eimeria stiedae oocysts and to determine the optimal dosage for suppressing the parasite’s infective phase. In this experiment, oocyst samples per milliliter were tested, and 6-well plates (2 mL) of 2.5% potassium dichromate solution containing 102 non-sporulated oocysts on Calotropis procera leaf extracts were exposed after 24, 48, 72, and 96 h, and the treatments were as follows: a nontreated control, 25%, 50%, 100%, and 150% of C. procera for oocyst activities. In addition, amprolium was utilized as a reference drug. The Calotropis procera was analyzed by GC-Mass, and results showed that the botanical extract contained 9 chemical components that were able to inhibit the oocysts of E. stiedae at 100% and 150% concentrations by about 78% and 93%, respectively. In general, an increase in the incubation period and a greater dose resulted in a decrease in the inhibition rate. The results showed that C. procera has an effective ability, inhibitory potential, and protective effect on the coccidian oocyst sporulation of E. stiedae. It can be used in the disinfection and sterilization of poultry and rabbit houses to get rid of Eimeria oocysts. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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18 pages, 3543 KiB  
Article
Anti–Zika Virus Activity and Isolation of Flavonoids from Ethanol Extracts of Curatella americana L. Leaves
by Lienne D’Auria Lima, Adriana Cotta Cardoso Reis, Jordano Augusto Carvalho Sousa, Gabriel Mendonça Valente, Breno de Mello Silva, Cíntia Lopes de Brito Magalhães, Markus Kohlhoff, Luiz Fernando de Medeiros Teixeira and Geraldo Célio Brandão
Molecules 2023, 28(6), 2546; https://doi.org/10.3390/molecules28062546 - 10 Mar 2023
Viewed by 1395
Abstract
The ethnomedicinal plant Curatella americana L. (Dilleniaceae) is a common shrub in the Brazilian Cerrado, whose ethanolic extract showed significant in vitro anti–Zika virus activity by the MTT colorimetric method. Currently, there is no drug in clinical use specifically for the treatment of [...] Read more.
The ethnomedicinal plant Curatella americana L. (Dilleniaceae) is a common shrub in the Brazilian Cerrado, whose ethanolic extract showed significant in vitro anti–Zika virus activity by the MTT colorimetric method. Currently, there is no drug in clinical use specifically for the treatment of this virus; therefore, in this work, the antiviral and cytotoxic properties of the ethanolic extract, fractions, and compounds were evaluated. The ethanolic extract of the leaves showed no cytotoxicity for the human MRC-5 cell and was moderately cytotoxic for the Vero cell (CC50 161.5 ± 2.01 µg/mL). This extract inhibited the Zika virus multiplication cycle with an EC50 of 85.2 ± 1.65 µg/mL. This extract was fractionated using the liquid–liquid partition technique, and the ethyl acetate fraction showed significant activity against the Zika virus with an EC50 of 40.7 ± 2.33 µg/mL. From the ethyl acetate fraction, the flavonoids quercetin-3-O-hexosylgallate (1), quercetin-3-O-glucoside (2), and quercetin (5) were isolated, and in addition to these compounds, a mixture of quercetin-3-O-rhamnoside (3) and quercetin-3-O-arabinoside (4) was also obtained. The isolated compounds quercetin and quercetin-3-O-hexosylgallate inhibited the viral cytopathic effect at an EC50 of 18.6 ± 2.8 and 152.8 ± 2.0, respectively. Additionally, analyses by liquid chromatography coupled to a mass spectrometer allowed the identification of another 24 minor phenolic constituents present in the ethanolic extract and in the ethyl acetate fraction of this species. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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14 pages, 2230 KiB  
Article
Unraveling the Variability of Essential Oil Composition in Different Accessions of Bunium persicum Collected from Different Temperate Micro-Climates
by Mudasir Hafiz Khan, Niyaz Ahmad Dar, Bashir Ahmad Alie, Sher Ahmad Dar, Ajaz Ahmad Lone, Ghulam Hassan Mir, Uzma Fayaz, Sajad Ali, Anshika Tyagi, Mohamed A. El-Sheikh and Saleh Alansi
Molecules 2023, 28(5), 2404; https://doi.org/10.3390/molecules28052404 - 6 Mar 2023
Cited by 2 | Viewed by 1399
Abstract
The present investigation was performed to evaluate the variability of the essential oil composition present in the seed extract of Kala zeera (Bunium persicum Bioss.) obtained from different geographical zones of Northwestern-Himalayan using Gas Chromatography-Mass Spectrum (GC-MS). The results of the GC-MS [...] Read more.
The present investigation was performed to evaluate the variability of the essential oil composition present in the seed extract of Kala zeera (Bunium persicum Bioss.) obtained from different geographical zones of Northwestern-Himalayan using Gas Chromatography-Mass Spectrum (GC-MS). The results of the GC-MS analysis revealed significant differences in the essential oil content. Significant variability was observed in the chemical constituents of the essential oils mainly for p-cymene, D-limonene, Gamma-terpinene, Cumic aldehyde and 1, 4-p-menthadien-7-al. Among these compounds, the highest average percentage across the locations was observed for gamma-terpinene (32.08%) which was followed by cumic aldehyde (25.07%), and 1, 4-p-menthadien-7-al (15.45%). Principal component analysis (PCA) also grouped the 4 highly significant compounds i.e., p-Cymene, Gamma-Terpinene, Cumic aldehyde, and 1,4-p-Menthadien-7-al into same cluster which are mainly distributed in Shalimar Kalazeera-1, and Atholi Kishtwar zones. The highest value of gamma-terpinene was recorded in Atholi accession (40.66%). However, among climatic zones Zabarwan Srinagar and Shalimar Kalazeera-1 was found to have highly positive significant correlation (0.99). The cophenetic correlation coefficient (c) was found to be 0.8334 during hierarchical clustering for 12 essential oil compounds showing that our results are highly correlated. Network analysis also showed the overlapping pattern and similar interaction between the 12 compounds as shown by hierarchical clustering analysis. From the results, it could be concluded that existence of variability among the various bioactive compounds of B. persicum which are probably to be incorporated to the potential list of drugs and may serve as good genetic source for various modern breeding programs. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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19 pages, 3718 KiB  
Article
Optimization and Preparation of Tallow with a Strong Aroma by Mild Oxidation
by Yanjing Jin, Junaid Raza, Huanlu Song, Lijin Wang, Qiaojun Wang, Guoli Ma and Yang Xiao
Molecules 2022, 27(24), 9047; https://doi.org/10.3390/molecules27249047 - 19 Dec 2022
Cited by 3 | Viewed by 1319
Abstract
This study was performed to extract and separate the volatiles with solid-phase microextraction (SPME), and was conducted to analyze volatile odor compounds qualitatively and quantitatively in the production of a strong aroma tallow by mild oxidation. A total of 51 odor compounds were [...] Read more.
This study was performed to extract and separate the volatiles with solid-phase microextraction (SPME), and was conducted to analyze volatile odor compounds qualitatively and quantitatively in the production of a strong aroma tallow by mild oxidation. A total of 51 odor compounds were detected in the tallow smelted under different conditions. It was found that the high proportion of aldehydes was an important feature of the aroma components in the oxidized melted tallow, such as 1-hexanal, heptanal, nonanal, octanal, benzaldehyde, etc. Through the determination of various indicators, sensory evaluation, and the gas chromatography-olfaction–mass spectrometry (GC-O–MS) analysis and, in combination with response surface methodology, the optimal process parameters for oxidative smelting of tallow were determined as follows: a reaction temperature of 149.61 °C, a reaction time of 31.68 min, and an airflow rate of 97.44 L/h. The accelerated oxidation test further verified the quality of the oxidized tallow. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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Graphical abstract

11 pages, 1256 KiB  
Article
Seasonal Variability of Juniperus communis L. Berry Ethanol Extracts: 2. In Vitro Ferric Reducing Ability of Plasma (FRAP) Assay
by Jozef Fejér, Daniela Gruľová, Adriana Eliašová and Ivan Kron
Molecules 2022, 27(24), 9027; https://doi.org/10.3390/molecules27249027 - 18 Dec 2022
Cited by 2 | Viewed by 1227
Abstract
In the present study, the seasonal variability of the in vitro ferric reducing ability of plasma (FRAP), total phenols, and terpene hydrocarbon content in 70% ethanol extracts were evaluated. The samples of crushed (CBs) and non-crushed ripe juniper berries (NCBs) collected at five [...] Read more.
In the present study, the seasonal variability of the in vitro ferric reducing ability of plasma (FRAP), total phenols, and terpene hydrocarbon content in 70% ethanol extracts were evaluated. The samples of crushed (CBs) and non-crushed ripe juniper berries (NCBs) collected at five localities in North-East Slovakia during the years 2012–2014 were compared. The method of preparation of the extract influenced the amount of dry matter (DM) in the extracts. In the CB extracts were statistically higher contents of DM (from 13.91 ± 0.11 g·L−1 to 23.84 ± 0.14 g·L−1) compared to NCB extracts (from 1.39 ± 0.01 g·L−1 to 16.55 ± 0.09 g·L−1). The differences in antioxidant activity between the investigated localities were statistically significant for both types of extract. For example, in 2013 in the locality of Zbojné, the FRAP in NCBs was 76.62 µmol·L−1·g−1 DM and in CBs was 138.27 µmol·L−1·g−1 DM, while in the Miľpoš locality, in NCBs there was 232.66 µmol·L−1·g−1 DM and in CBs there was 1178.98 µmol·L−1·g−1 DM. The differences in the antioxidant activity between the studied years in the case of NCB extracts were not statistically significant. In the case of CB extracts, significant differences between the evaluated years were found. Statistics by ANOVA confirmed that CB extracts prepared from berries in the year 2013 showed significantly higher activity compared to CB extracts from berries from the years 2012 and 2014. Based on the Pearson we found a negative correlation coefficient between the FRAP assay and the content of total polyphenols in NCB extracts (−0.531 in 2012; −0.349 in 2013; and −0.224 in 2014). In contrast, CB extracts showed a positive correlation coefficient (0.843 in 2012; 0.742 in 2013; 0.617 in 2014). Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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Review

Jump to: Research

47 pages, 1131 KiB  
Review
Design of Experiments for Optimizing Ultrasound-Assisted Extraction of Bioactive Compounds from Plant-Based Sources
by Luis Miguel Anaya-Esparza, Edward F. Aurora-Vigo, Zuamí Villagrán, Ernesto Rodríguez-Lafitte, José Martín Ruvalcaba-Gómez, Miguel Ángel Solano-Cornejo, Victor Manuel Zamora-Gasga, Efigenia Montalvo-González, Horacio Gómez-Rodríguez, César Eduardo Aceves-Aldrete and Napoleón González-Silva
Molecules 2023, 28(23), 7752; https://doi.org/10.3390/molecules28237752 - 24 Nov 2023
Viewed by 1769
Abstract
Plant-based materials are an important source of bioactive compounds (BC) with interesting industrial applications. Therefore, adequate experimental strategies for maximizing their recovery yield are required. Among all procedures for extracting BC (maceration, Soxhlet, hydro-distillation, pulsed-electric field, enzyme, microwave, high hydrostatic pressure, and supercritical [...] Read more.
Plant-based materials are an important source of bioactive compounds (BC) with interesting industrial applications. Therefore, adequate experimental strategies for maximizing their recovery yield are required. Among all procedures for extracting BC (maceration, Soxhlet, hydro-distillation, pulsed-electric field, enzyme, microwave, high hydrostatic pressure, and supercritical fluids), the ultrasound-assisted extraction (UAE) highlighted as an advanced, cost-efficient, eco-friendly, and sustainable alternative for recovering BC (polyphenols, flavonoids, anthocyanins, and carotenoids) from plant sources with higher yields. However, the UAE efficiency is influenced by several factors, including operational variables and extraction process (frequency, amplitude, ultrasonic power, pulse cycle, type of solvent, extraction time, solvent-to-solid ratio, pH, particle size, and temperature) that exert an impact on the molecular structures of targeted molecules, leading to variations in their biological properties. In this context, a diverse design of experiments (DOEs), including full or fractional factorial, Plackett–Burman, Box-Behnken, Central composite, Taguchi, Mixture, D-optimal, and Doehlert have been investigated alone and in combination to optimize the UAE of BC from plant-based materials, using the response surface methodology and mathematical models in a simple or multi-factorial/multi-response approach. The present review summarizes the advantages and limitations of the most common DOEs investigated to optimize the UAE of bioactive compounds from plant-based materials. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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50 pages, 2777 KiB  
Review
Advances in Natural Product Extraction Techniques, Electrospun Fiber Fabrication, and the Integration of Experimental Design: A Comprehensive Review
by Juthaporn Ponphaiboon, Wantanwa Krongrawa, Wah Wah Aung, Nawinda Chinatangkul, Sontaya Limmatvapirat and Chutima Limmatvapirat
Molecules 2023, 28(13), 5163; https://doi.org/10.3390/molecules28135163 - 2 Jul 2023
Cited by 10 | Viewed by 4092
Abstract
The present review explores the growing interest in the techniques employed for extracting natural products. It emphasizes the limitations of conventional extraction methods and introduces superior non-conventional alternatives, particularly ultrasound-assisted extraction. Characterization and quantification of bioactive constituents through chromatography coupled with spectroscopy are [...] Read more.
The present review explores the growing interest in the techniques employed for extracting natural products. It emphasizes the limitations of conventional extraction methods and introduces superior non-conventional alternatives, particularly ultrasound-assisted extraction. Characterization and quantification of bioactive constituents through chromatography coupled with spectroscopy are recommended, while the importance of method development and validation for biomarker quantification is underscored. At present, electrospun fibers provide a versatile platform for incorporating bioactive extracts and have extensive potential in diverse fields due to their unique structural and functional characteristics. Thus, the review also highlights the fabrication of electrospun fibers containing bioactive extracts. The preparation of biologically active extracts under optimal conditions, including the selection of safe solvents and cost-effective equipment, holds promising potential in the pharmaceutical, food, and cosmetic industries. Integration of experimental design into extraction procedures and formulation development is essential for the efficient production of health products. The review explores potential applications of encapsulating natural product extracts in electrospun fibers, such as wound healing, antibacterial activity, and antioxidant properties, while acknowledging the need for further exploration and optimization in this field. The findings discussed in this review are anticipated to serve as a valuable resource for the processing industry, enabling the utilization of affordable and environmentally friendly, natural, and raw materials. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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22 pages, 3952 KiB  
Review
Cavitation-Effect-Based Treatments and Extractions for Superior Fruit and Milk Valorisation
by Madalina-Petruta Bucur, Maria-Cristina Radulescu, Gabriel Lucian Radu and Bogdan Bucur
Molecules 2023, 28(12), 4677; https://doi.org/10.3390/molecules28124677 - 9 Jun 2023
Cited by 2 | Viewed by 1312
Abstract
Ultrasound generates cavities in liquids with high-energy behaviour due to large pressure variations, leading to (bio)chemical effects and material modification. Numerous cavity-based treatments in food processes have been reported, but the transition from research to industrial applications is hampered by specific engineering factors, [...] Read more.
Ultrasound generates cavities in liquids with high-energy behaviour due to large pressure variations, leading to (bio)chemical effects and material modification. Numerous cavity-based treatments in food processes have been reported, but the transition from research to industrial applications is hampered by specific engineering factors, such as the combination of several ultrasound sources, more powerful wave generators or tank geometry. The challenges and development of cavity-based treatments developed for the food industry are reviewed with examples limited to two representative raw materials (fruit and milk) with significantly different properties. Both active compound extraction and food processing techniques based on ultrasound are taken into consideration. Full article
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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