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20 pages, 12676 KiB

Open AccessArticle

Homoleptic Complexes of Heterocyclic Curcuminoids with Mg(II) and Cu(II): First Conformationally Heteroleptic Case, Crystal Structures, and Biological Properties

by William Meza-Morales, Yuritzi Alejo-Osorio, Yair Alvarez-Ricardo, Marco A. Obregón-Mendoza, Juan C. Machado-Rodriguez, Antonino Arenaza-Corona, Rubén A. Toscano, María Teresa Ramírez-Apan and Raúl G. Enríquez

Molecules 2023, 28(3), 1434; https://doi.org/10.3390/molecules28031434 - 2 Feb 2023

Cited by 6 | Viewed by 1955

Abstract

We report herein the synthesis and characterization of three heterocyclic curcuminoid ligands and their homoleptic metal complexes with magnesium and copper. Thus, N-methyl-2-pyrrolecarboxaldehyde, Furan-2-carboxaldehyde, and 2-Thiophenecarboxaldehyde were condensed with 2,4-pentanedione-boron trioxide complex. The first N-methyl-2-pyrrole curcuminoid and its Mg(II) complex are reported. All [...] Read more.

We report herein the synthesis and characterization of three heterocyclic curcuminoid ligands and their homoleptic metal complexes with magnesium and copper. Thus, N-methyl-2-pyrrolecarboxaldehyde, Furan-2-carboxaldehyde, and 2-Thiophenecarboxaldehyde were condensed with 2,4-pentanedione-boron trioxide complex. The first N-methyl-2-pyrrole curcuminoid and its Mg(II) complex are reported. All curcuminoid ligands and their corresponding metal complexes were characterized by infrared spectroscopy (IR), liquid state nuclear magnetic resonance (LSNMR), electron paramagnetic resonance (EPR), mass spectrometry (MS) and single crystal X-ray diffraction (SCXRD). The ThiopheneCurc-Cu (9) constitutes the first case of a “conformationally-heteroleptic” complex. The unique six-peaks star arrangement for the ThiopheneCurc ligand derived from the supramolecular description is reported. The metal complexes of FuranCurc-Mg (5) and ThiopheneCurc-Cu (9) have a good antioxidant effect (IC₅₀ = 11.26 ± 1.73 and 10.30 ± 0.59 μM), three and two times higher than their free ligands respectively. Additionally, (5) shows remarkable cytotoxicity against colon cancer adenocarcinoma cell line HCT-15, comparable to that of cisplatin, with a negligible toxic effect in vitro towards a healthy monkey kidney cell line (COS-7). Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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12 pages, 5548 KiB

Open AccessArticle

Rutin Improves Anxiety and Reserpine-Induced Depression in Rats

by Ahmed I Foudah, Mohammed H Alqarni, Aftab Alam, Sushma Devi, Mohammad A Salkini and Prawez Alam

Molecules 2022, 27(21), 7313; https://doi.org/10.3390/molecules27217313 - 27 Oct 2022

Cited by 21 | Viewed by 3241

Abstract

Mental disorders have a poor clinical prognosis and account for approximately 8% of the global burden of disease. Some examples of mental disorders are anxiety and depression. Conventional antidepressants have limited efficacy in patients because their pharmacological effects wear off, and side effects [...] Read more.

Mental disorders have a poor clinical prognosis and account for approximately 8% of the global burden of disease. Some examples of mental disorders are anxiety and depression. Conventional antidepressants have limited efficacy in patients because their pharmacological effects wear off, and side effects increase with prolonged use. It is claimed that herbal medicine’s antioxidant capacity helps regulate people’s mood and provide a more substantial pharmacological effect. With this background, the purpose of this study is to investigate the effect of rutin on reserpine-induced anxiety and depression in rats. The animals were divided into groups of six rats each: normal control (water), a depression model, a rutin-treated rat model, and an amitriptyline-treated rat model. According to the results, 14 days of treatment with rutin, once daily, showed a modest antidepressant effect. This effect was mediated by increased serotonin, norepinephrine, and dopamine levels in cortical and hippocampal regions. The antioxidant and vasodilator properties of rutin may contribute to its antidepressant properties. According to this study, rutin has shown antidepressant effects by reducing antioxidant activity and acetylcholinesterase. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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15 pages, 2876 KiB

Open AccessArticle

Chemical Composition of Tagetes patula Flowers Essential Oil and Hepato-Therapeutic Effect against Carbon Tetrachloride-Induced Toxicity (In-Vivo)

by Hanan Y. Aati, Mahmoud Emam, Jawaher Al-Qahtani, Sultan Aati, Abdulrahman Aati, Juergen Wanner and Mohamed M. Seif

Molecules 2022, 27(21), 7242; https://doi.org/10.3390/molecules27217242 - 25 Oct 2022

Cited by 5 | Viewed by 1950

Abstract

The liver is a crucial organ among body organs due to its wide functions, in particular, detoxification and metabolism. Exposure to detrimental chemicals or viral infections may provoke liver dysfunction and ultimately induce liver tissue damage. Finding natural substances for liver disease treatment [...] Read more.

The liver is a crucial organ among body organs due to its wide functions, in particular, detoxification and metabolism. Exposure to detrimental chemicals or viral infections may provoke liver dysfunction and ultimately induce liver tissue damage. Finding natural substances for liver disease treatment to overcome the conventional treatments’ side effects has attracted the attention of researchers worldwide. Our current work was conducted to investigate the hepato-therapeutic activities of essential oil (EO) isolated from Tagetes patula flowers. EO was extracted using the hydro-distillation (HD) technique and its chemical composition was identified by GC/MS. Then, the hepatic treatment potential of extracted EO was evaluated in vivo against CCL₄ in rats. HD of T. patula flowers yielded highly chemical constituents of EO along with significant antioxidant potential. A coherent molecular network was fashioned via the Global Natural Products Social Molecular Networking (GNPS) to visualize the essential components and revealed that the sesquiterpene (E)-β-caryophyllene was the most predominant volatile constituent which accounted for 24.1%. The treatment of CCL₄ led to significant induced oxidative stress markers malonaldehyde, total protein, and non-protein sulfhydryl, as well as elevated serum aminotransferase, gamma-glutamyl transferase, alkaline phosphatase, and bilirubin. In addition, it disrupted the level of lipid profile. The post-treatment using T. patula EO succeeded in relieving all toxic effects of CCl₄ and recuperating the histopathological signs induced by CCL₄. Silymarin was used as a standard hepatoprotective agent. The obtained results demonstrated that the extracted EO exerted high protective activities against the toxicity of CCL₄. Moreover, the T. patula flowers EO can be used as a natural remedy to relieve many contemporary liver diseases related to oxidative stress. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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21 pages, 2167 KiB

Open AccessArticle

Understanding the Antilymphoma Activity of Annona macroprophyllata Donn and Its Acyclic Terpenoids: In Vivo, In Vitro, and In Silico Studies

by Jesica Ramírez-Santos, Fernando Calzada, Jessica Elena Mendieta-Wejebe, Rosa María Ordoñez-Razo, Rubria Marlen Martinez-Casares and Miguel Valdes

Molecules 2022, 27(20), 7123; https://doi.org/10.3390/molecules27207123 - 21 Oct 2022

Cited by 2 | Viewed by 2110

Abstract

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as [...] Read more.

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as antilymphoma agents. We identified the terpenoids farnesyl acetate (FA), phytol (PT) and geranylgeraniol (Gg) using gas chromatography–mass spectroscopy (GC-MS) and spectroscopic (¹H, and ¹³C NMR) methods applied to petroleum ether extract of leaves from A. macroprophyllata (PEAm). We investigated antitumor potential in Balb/c mice inoculated with U-937 cells by assessing brine shrimp lethality (BSL), and cytotoxic activity in these cells. In addition, to assess the potential toxicity of PEAm, FA, PT and Gg in humans, we tested their acute oral toxicity in mice. Our results showed that the three terpenoids exhibited considerable antilymphoma and cytotoxic activity. In terms of lethality, we determined a median lethal dose (LD₅₀) for thirteen isolated products of PEAm. Gg, PT and AF all exhibited a higher lethality with values of 1.41 ± 0.42, 3.03 ± 0.33 and 5.82 ± 0.58 µg mL⁻¹, respectively. To assess cytotoxic activity against U-937 cells, we calculated the mean cytotoxic concentration (CC₅₀) and found that FA and PT were closer in respect to the control drug methotrexate (MTX, 0.243 ± 0.007 µM). In terms of antilymphoma activity, we found that FA, PT and Gg considerably inhibited lymph node growth, with median effective doses (ED₅₀) of 5.89 ± 0.39, 6.71 ± 0.31 and 7.22 ± 0.51 mg kg⁻¹ in females and 5.09 ± 0.66, 5.83 ± 0.50 and 6.98 ± 0.57mg kg ⁻¹ in males, respectively. Regarding acute oral toxicity, we classified all three terpenoids as category IV, indicating a high safety margin for human administration. Finally, in a molecular docking study of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, we found binding of terpenoids to some amino acids of the catalytic site, suggesting an effect upon activity with a resulting decrease in the synthesis of intermediates involved in the prenylation of proteins involved in cancer progression. Our findings suggest that the acyclic terpenoids FA, PT, and Gg may serve as scaffolds for the development of new treatments for non-Hodgkin’s lymphoma. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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13 pages, 1670 KiB

Open AccessArticle

Influence of Molecular Weight of Polysaccharides from Laminaria japonica to LJP-Based Hydrogels: Anti-Inflammatory Activity in the Wound Healing Process

by Yifan Chen, Weixuan Huang, Yang Chen, Minqian Wu, Ruohan Jia and Lijun You

Molecules 2022, 27(20), 6915; https://doi.org/10.3390/molecules27206915 - 15 Oct 2022

Cited by 10 | Viewed by 2071

Abstract

In this study, polysaccharides from Laminaria japonica (LJP) were produced by the treatment of ultraviolet/hydrogen peroxide (UV/H₂O₂) degradation into different molecular weights. Then, the degraded LJP were used to prepare LJP/chitosan/PVA hydrogel wound dressings. As the molecular weight of [...] Read more.

In this study, polysaccharides from Laminaria japonica (LJP) were produced by the treatment of ultraviolet/hydrogen peroxide (UV/H₂O₂) degradation into different molecular weights. Then, the degraded LJP were used to prepare LJP/chitosan/PVA hydrogel wound dressings. As the molecular weight of LJP decreased from 315 kDa to 20 kDa, the swelling ratio of the LJP-based hydrogels rose from 14.38 ± 0.60 to 20.47 ± 0.42 folds of the original weight. However, the mechanical properties of LJP-based hydrogels slightly decreased. With the extension of the UV/H₂O₂ degradation time, the molecular weight of LJP gradually decreased, and the anti-inflammatory activities of LJP-based hydrogels gradually increased. LJP that were degraded for 60 min (60-gel) showed the best inhibition effects on proinflammatory cytokines, while the contents of TNF-α, IL-6, and IL-1β decreased by 57.33%, 44.80%, and 67.72%, respectively, compared with the Model group. The above results suggested that low Mw LJP-based hydrogels showed great potential for a wound dressing application. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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21 pages, 2856 KiB

Open AccessArticle

Sahlep (Dactylorhiza osmanica): Phytochemical Analyses by LC-HRMS, Molecular Docking, Antioxidant Activity, and Enzyme Inhibition Profiles

by Hatice Kiziltas, Ahmet Ceyhan Goren, Saleh H. Alwasel and İlhami Gulcin

Molecules 2022, 27(20), 6907; https://doi.org/10.3390/molecules27206907 - 14 Oct 2022

Cited by 29 | Viewed by 2738

Abstract

Studies have shown an inverse correlation among age-related illnesses like coronary heart disease and cancer and intake of fruit and vegetable. Given the probable health benefits of natural antioxidants from plants, research on them has increased. Dactylorhiza osmanica is consumed as a food [...] Read more.

Studies have shown an inverse correlation among age-related illnesses like coronary heart disease and cancer and intake of fruit and vegetable. Given the probable health benefits of natural antioxidants from plants, research on them has increased. Dactylorhiza osmanica is consumed as a food and traditional medicine plant in some regions of Turkey, so evaluation of the biological ability of this species is important. In this study, the amount of phenolic content (LC-HRMS), antioxidant activities and enzyme inhibitory properties of an endemic plant, D. osmanica, were investigated. The antioxidant capacities of an ethanol extract of D. osmanica aerial parts (EDOA) and roots (EDOR) were evaluated with various antioxidant methods. Additionally, the enzyme inhibitory effects of EDOA and EDOR were examined against acetylcholinesterase (AChE), α-glycosidase, and α-amylase enzymes, which are associated with common and global Alzheimer’s disease and diabetes mellitus. The IC₅₀ values of EDOA against the enzymes were found to be 1.809, 1.098, and 0.726 mg/mL, respectively; and the IC₅₀ values of EDOR against the enzymes were found to be 2.466, 0.442, and 0.415 mg/mL, respectively. Additionally, LC-HRMS analyses revealed p-Coumaric acid as the most plentiful phenolic in both EDOA (541.49 mg/g) and EDOR (559.22 mg/g). Furthermore, the molecular docking interaction of p-coumaric acid, quercitrin, and vanillic acid, which are the most plentiful phenolic compounds in the extracts, with AChE, α-glucosidase, and α-amylase, were evaluated using AutoDock Vina software. The rich phenolic content and the effective antioxidant ability and enzyme inhibition potentials of EDOA and EDOR may support the plant’s widespread food and traditional medicinal uses. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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11 pages, 1873 KiB

Open AccessArticle

Development of Stable Liposomal Drug Delivery System of Thymoquinone and Its In Vitro Anticancer Studies Using Breast Cancer and Cervical Cancer Cell Lines

by Mohammad Hossain Shariare, Md Asaduzzaman Khan, Abdullah Al-Masum, Junayet Hossain Khan, Jamal Uddin and Mohsin Kazi

Molecules 2022, 27(19), 6744; https://doi.org/10.3390/molecules27196744 - 10 Oct 2022

Cited by 15 | Viewed by 3035

Abstract

Thymoquinone, a well-known phytoconstituent derived from the seeds of Nigella sativa, exhibits unique pharmacological activities However, despite the various medicinal properties of thymoquinone, its administration in vivo remains challenging due to poor aqueous solubility, bioavailability, and stability. Therefore, an advanced drugdelivery system [...] Read more.

Thymoquinone, a well-known phytoconstituent derived from the seeds of Nigella sativa, exhibits unique pharmacological activities However, despite the various medicinal properties of thymoquinone, its administration in vivo remains challenging due to poor aqueous solubility, bioavailability, and stability. Therefore, an advanced drugdelivery system is required to improve the therapeutic outcome of thymoquinone by enhancing its solubility and stability in biological systems. Therefore, this study is mainly focused on preparing thymoquinone-loaded liposomes to improve its physicochemical stability in gastric media and its performance in different cancer cell line studies. Liposomes were prepared using phospholipid extracted from egg yolk. The liposomal nano preparations were evaluated in terms of hydrodynamic diameter, zeta potential, microscopic analysis, and entrapment efficiency. Cell-viability measurements were conducted using breast and cervical cancer cell lines. Optimized liposomal preparation exhibited polygonal, globule-like shape with a hydrodynamic diameter of less than 260 nm, PDI of 0.6, and zeta potential values of −23.0 mV. Solid-state characterizations performed using DSC and XRPD showed that the freeze-dried liposomal preparations were amorphous in nature. Gastric pH stability data showed no physical changes (precipitation, degradation) or significant growth in the average size of blank and thymoquinone-loaded liposomes after 24 h. Cell line studies exhibited better performance for thymoquinone-loaded liposomal drug delivery system compared with the thymoquinone-only solution; this finding can play a critical role in improving breast and cervical cancer treatment management. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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16 pages, 2482 KiB

Open AccessArticle

Two Ways to Achieve the Same Goal—Two Validated Quantitative NMR Strategies for a Low-Abundance Natural Product in Standardized Extracts: The Case of Hepatodamianol in Turnera diffusa

by Aída Parra-Naranjo, Cecilia Delgado-Montemayor, Ricardo Salazar-Aranda, Rocío Castro-Ríos, Alma L. Saucedo and Noemí Waksman-Minsky

Molecules 2022, 27(19), 6593; https://doi.org/10.3390/molecules27196593 - 5 Oct 2022

Cited by 1 | Viewed by 1858

Abstract

The quantification of low-abundance secondary metabolites in plant extracts is an analytical problem that can be addressed by different analytical platforms, the most common being those based on chromatographic methods coupled to a high-sensitivity detection system. However, in recent years nuclear magnetic resonance [...] Read more.

The quantification of low-abundance secondary metabolites in plant extracts is an analytical problem that can be addressed by different analytical platforms, the most common being those based on chromatographic methods coupled to a high-sensitivity detection system. However, in recent years nuclear magnetic resonance (NMR) has become an analytical tool of primary choice for this type of problem because of its reliability, inherent simplicity in sample preparation, reduced analysis time, and low solvent consumption. The versatility of strategies based on quantitative NMR (qNMR), such as internal and external standards and electronic references, among others, and the need to develop validated analytical methods make it essential to compare procedures that must rigorously satisfy the analytical well-established acceptance criteria for method validation. In this work, two qNMR methods were developed for the quantification of hepatodamianol, a bioactive component of T. diffusa. The first method was based on a conventional external standard calibration, and the second one was based on the pulse length-based concentration determination (PULCON) method using the ERETIC2 module as a quantitation tool available in TopSpin software. The results show that both procedures allow the content of the analyte of interest in a complex matrix to be determined in a satisfactory way, under strict analytical criteria. In addition, ERETIC2 offers additional advantages such as a reduction in experimental time, reagent consumption, and waste generated. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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14 pages, 5981 KiB

Open AccessArticle

Antioxidant, Anti-Bacterial, and Congo Red Dye Degradation Activity of Ag_xO-Decorated Mustard Oil-Derived rGO Nanocomposites

by G. S. Lekshmi, Tamilselvi Ramasamy, Olha Bazaka, Igor Levchenko, Kateryna Bazaka, Raji Govindan and Mohandas Mandhakini

Molecules 2022, 27(18), 5950; https://doi.org/10.3390/molecules27185950 - 13 Sep 2022

Cited by 6 | Viewed by 2267

Abstract

Scaling up the production of functional reduced graphene oxide (rGO) and its composites requires the use of low-cost, simple, and sustainable synthesis methods, and renewable feedstocks. In this study, silver oxide-decorated rGO (Ag_xO−rGO) composites were prepared by open-air combustion of mustard [...] Read more.

Scaling up the production of functional reduced graphene oxide (rGO) and its composites requires the use of low-cost, simple, and sustainable synthesis methods, and renewable feedstocks. In this study, silver oxide-decorated rGO (Ag_xO−rGO) composites were prepared by open-air combustion of mustard oil, essential oil-containing cooking oil commercially produced from the seeds of Brassica juncea. Silver oxide (Ag_xO) nanoparticles (NPs) were synthesized using Coleus aromaticus leaf extract as a reducing agent. Formation of mustard seed rGO and Ag_xO NPs was confirmed by UV-visible characteristic peaks at 258 nm and 444 nm, respectively. rGO had a flake-like morphology and a crystalline structure, with Raman spectra showing clear D and G bands with an I_D/I_G ratio of 0.992, confirming the fewer defects in the as-prepared mustard oil-derived rGO (M−rGO). The rGO-Ag_xO composite showed a degradation efficiency of 81.9% with a rate constant k⁻¹ of 0.9506 min⁻¹ for the sodium salt of benzidinediazo-bis-1-naphthylamine-4-sulfonic acid (known as the azo dye Congo Red) in an aqueous solution under visible light irradiation. The composite also showed some antimicrobial activity against Klebsilla pneomoniae, Escherichiacoli, and Staphylococcusaureus bacterial cells, with inhibition zones of ~15, 18, and 14 mm, respectively, for a concentration of 300 µg/mL. At 600 µg/mL concentration, the composite also showed moderate scavenging activity for 2,2-diphenyl-1-picrylhydrazyl of ~30.6%, with significantly lower activities measured for Ag_xO (at ~18.1%) and rGO (~8%) when compared to control. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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17 pages, 1860 KiB

Open AccessArticle

Antioxidant, Antidiabetic, Anticholinergic, and Antiglaucoma Effects of Magnofluorine

by Lokman Durmaz, Hatice Kiziltas, Leyla Guven, Hasan Karagecili, Saleh Alwasel and İlhami Gulcin

Molecules 2022, 27(18), 5902; https://doi.org/10.3390/molecules27185902 - 11 Sep 2022

Cited by 41 | Viewed by 3404

Abstract

Magnofluorine, a secondary metabolite commonly found in various plants, has pharmacological potential; however, its antioxidant and enzyme inhibition effects have not been investigated. We investigated the antioxidant potential of Magnofluorine using bioanalytical assays with 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS^•+), N,N [...] Read more.

Magnofluorine, a secondary metabolite commonly found in various plants, has pharmacological potential; however, its antioxidant and enzyme inhibition effects have not been investigated. We investigated the antioxidant potential of Magnofluorine using bioanalytical assays with 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS^•+), N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD^•+), and 1,1-diphenyl-2-picrylhydrazyl (DPPH^•) scavenging abilities and K₃[Fe(CN)₆] and Cu²⁺ reduction abilities. Further, we compared the effects of Magnofluorine and butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), α-Tocopherol, and Trolox as positive antioxidant controls. According to the analysis results, Magnofluorine removed 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals with an IC₅₀ value of 10.58 μg/mL. The IC₅₀ values of BHA, BHT, Trolox, and α-Tocopherol were 10.10 μg/mL, 25.95 μg/mL, 7.059 μg/mL, and 11.31 μg/mL, respectively. Our results indicated that the DPPH· scavenging effect of Magnofluorine was similar to that of BHA, close to that of Trolox, and better than that of BHT and α-tocopherol. The inhibition effect of Magnofluorine was examined against enzymes, such as acetylcholinesterase (AChE), α-glycosidase, butyrylcholinesterase (BChE), and human carbonic anhydrase II (hCA II), which are linked to global disorders, such as diabetes, Alzheimer’s disease (AD), and glaucoma. Magnofluorine inhibited these metabolic enzymes with Ki values of 10.251.94, 5.991.79, 25.411.10, and 30.563.36 nM, respectively. Thus, Magnofluorine, which has been proven to be an antioxidant, antidiabetic, and anticholinergic in our study, can treat glaucoma. In addition, molecular docking was performed to understand the interactions between Magnofluorine and target enzymes BChE (D: 6T9P), hCA II (A:3HS4), AChE (B:4EY7), and α-glycosidase (C:5NN8). The results suggest that Magnofluorine may be an important compound in the transition from natural sources to industrial applications, especially new drugs. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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16 pages, 6699 KiB

Open AccessArticle

Apoptotic and Cell Cycle Effects of Triterpenes Isolated from Phoradendron wattii on Leukemia Cell Lines

by Lía S. Valencia-Chan, Dafné Moreno-Lorenzana, Jimmy Josué Ceballos-Cruz, Sergio R. Peraza-Sánchez, Antonieta Chávez-González and Rosa E. Moo-Puc

Molecules 2022, 27(17), 5616; https://doi.org/10.3390/molecules27175616 - 31 Aug 2022

Cited by 3 | Viewed by 2129

Abstract

Current antineoplastic agents present multiple disadvantages, driving an ongoing search for new and better compounds. Four lupane-type triterpenes, 3α,24-dihydroxylup-20(29)-en-28-oic acid (1), 3α,23-dihydroxy-30-oxo-lup-20(29)-en-28-oic acid (2), 3α,23-O-isopropylidenyl-3α,23-dihydroxylup-20(29)-en-28-oic acid (3), and 3α,23-dihydroxylup-20(29)-en-28-oic acid (4), previously isolated [...] Read more.

Current antineoplastic agents present multiple disadvantages, driving an ongoing search for new and better compounds. Four lupane-type triterpenes, 3α,24-dihydroxylup-20(29)-en-28-oic acid (1), 3α,23-dihydroxy-30-oxo-lup-20(29)-en-28-oic acid (2), 3α,23-O-isopropylidenyl-3α,23-dihydroxylup-20(29)-en-28-oic acid (3), and 3α,23-dihydroxylup-20(29)-en-28-oic acid (4), previously isolated from Phoradendron wattii, were evaluated on two cell lines of chronic (K562) and acute (HL60) myeloid leukemia. Compounds 1, 2, and 4 decreased cell viability and inhibit proliferation, mainly in K562, and exhibited an apoptotic effect from 24 h of treatment. Of particular interest is compound 2, which caused arrest in active phases (G2/M) of the cell cycle, as shown by in silico study of the CDK1/Cyclin B/Csk2 complex by molecular docking. This compound [3α,23-dihydroxy-30-oxo-lup-20(29)-en-28-oic acid] s a promising candidate for incorporation into cancer treatments and deserves further study. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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10 pages, 12468 KiB

Open AccessArticle

Cytotoxic Effects on Breast Cancer Cell Lines of Chalcones Derived from a Natural Precursor and Their Molecular Docking Analysis

by Luis Bustos, Carlos Echiburú-Chau, Alejandro Castro-Alvarez, Ben Bradshaw, Mario J. Simirgiotis, Marco Mellado, Claudio Parra and Mauricio Cuellar

Molecules 2022, 27(14), 4387; https://doi.org/10.3390/molecules27144387 - 8 Jul 2022

Cited by 8 | Viewed by 2594

Abstract

This study aimed to determine the in vitro cytotoxicity and understand possible cytotoxic mechanisms via an in silico study of eleven chalcones synthesized from two acetophenones. Five were synthesized from a prenylacetophenone isolated from a plant that grows in the Andean region of [...] Read more.

This study aimed to determine the in vitro cytotoxicity and understand possible cytotoxic mechanisms via an in silico study of eleven chalcones synthesized from two acetophenones. Five were synthesized from a prenylacetophenone isolated from a plant that grows in the Andean region of the Atacama Desert. The cytotoxic activity of all the synthesized chalcones was tested against breast cancer cell lines using an MTT cell proliferation assay. The results suggest that the prenyl group in the A-ring of the methoxy and hydroxyl substituents of the B-ring appear to be crucial for the cytotoxicity of these compounds. The chalcones 12 and 13 showed significant inhibitory effects against growth in MCF-7 cells (IC₅₀ 4.19 ± 1.04 µM and IC₅₀ 3.30 ± 0.92 µM), ZR-75-1 cells (IC₅₀ 9.40 ± 1.74 µM and IC₅₀ 8.75 ± 2.01µM), and MDA-MB-231 cells (IC₅₀ 6.12 ± 0.84 µM and IC₅₀ 18.10 ± 1.65 µM). Moreover, these chalcones showed differential activity between MCF-10F (IC₅₀ 95.76 ± 1.52 µM and IC₅₀ 95.11 ± 1.97 µM, respectively) and the tumor lines. The in vitro results agree with molecular coupling results, whose affinity energies and binding mode agree with the most active compounds. Thus, compounds 12 and 13 can be considered for further studies and are candidates for developing new antitumor agents. In conclusion, these observations give rise to a new hypothesis for designing chalcones with potential cytotoxicity with high potential for the pharmaceutical industry. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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Review

Jump to: Research

38 pages, 4828 KiB

Open AccessReview

Overview of the Justicia Genus: Insights into Its Chemical Diversity and Biological Potential

by Marcos Rodrigo Beltrão Carneiro, Lóide Oliveira Sallum, José Luís Rodrigues Martins, Josana de Castro Peixoto, Hamilton Barbosa Napolitano and Lucimar Pinheiro Rosseto

Molecules 2023, 28(3), 1190; https://doi.org/10.3390/molecules28031190 - 25 Jan 2023

Cited by 10 | Viewed by 4146

Abstract

The genus Justicia has more than 600 species distributed in both hemispheres, in the tropics and temperate regions, and it is used in the treatment of numerous pathologies. This study presents a review of the biological activities of plant extracts and isolated chemical [...] Read more.

The genus Justicia has more than 600 species distributed in both hemispheres, in the tropics and temperate regions, and it is used in the treatment of numerous pathologies. This study presents a review of the biological activities of plant extracts and isolated chemical constituents of Justicia (ACANTHACEAE), identified in the period from May 2011 to August 2022. We analyzed over 176 articles with various biological activities and chemical compound descriptions present in the 29 species of Justicia. These have a variety of applications, such as antioxidant and antimicrobial, with alkaloids and flavonoids (e.g., naringenin) the most frequently identified secondary metabolites. The most observed species were Justicia gendarussa Burm., Justicia procumbens L., Justicia adhatoda L., Justicia spicigera Schltdl, and Justicia pectoralis Jacq. The frontier molecular orbitals carried out using density functional theory (M062X and basis set 6-311++G(d,p) indicate reactive sites for naringenin compound and a chemical reaction on phytomedicine activity. The energy gap (206.99 kcal/mol) and dimer solid state packing point to chemical stability. Due to the wide variety of pharmacological uses of these species, this review points toward the development of new phytomedicines. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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23 pages, 6236 KiB

Open AccessReview

Strategies for Solubility and Bioavailability Enhancement and Toxicity Reduction of Norcantharidin

by Qian Liu, Henglai Sun, Xinyu Li, Huagang Sheng and Liqiao Zhu

Molecules 2022, 27(22), 7740; https://doi.org/10.3390/molecules27227740 - 10 Nov 2022

Cited by 5 | Viewed by 2011

Abstract

Cantharidin (CTD) is the main active ingredient isolated from Mylabris, and norcantharidin (NCTD) is a demethylated derivative of CTD, which has similar antitumor activity to CTD and lower toxicity than CTD. However, the clinical use of NCTD is limited due to its poor [...] Read more.

Cantharidin (CTD) is the main active ingredient isolated from Mylabris, and norcantharidin (NCTD) is a demethylated derivative of CTD, which has similar antitumor activity to CTD and lower toxicity than CTD. However, the clinical use of NCTD is limited due to its poor solubility, low bioavailability, and toxic effects on normal cells. To overcome these shortcomings, researchers have explored a number of strategies, such as chemical structural modifications, microsphere dispersion systems, and nanodrug delivery systems. This review summarizes the structure–activity relationship of NCTD and novel strategies to improve the solubility and bioavailability of NCTD as well as reduce the toxicity. This review can provide evidence for further research of NCTD. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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29 pages, 4636 KiB

Open AccessReview

Biomedical and Antioxidant Potentialities in Chilli: Perspectives and Way Forward

by Solanki Bal, Amit Baran Sharangi, Tarun Kumar Upadhyay, Fahad Khan, Pratibha Pandey, Samra Siddiqui, Mohd Saeed, Hae-Jeung Lee and Dharmendra K. Yadav

Molecules 2022, 27(19), 6380; https://doi.org/10.3390/molecules27196380 - 27 Sep 2022

Cited by 21 | Viewed by 5857

Abstract

Worldwide, since ages and nowadays, traditional medicine is well known, owing to its biodiversity, which immensely contributed to the advancement and development of complementary and alternative medicines. There is a wide range of spices, herbs, and trees known for their medicinal uses. Chilli [...] Read more.

Worldwide, since ages and nowadays, traditional medicine is well known, owing to its biodiversity, which immensely contributed to the advancement and development of complementary and alternative medicines. There is a wide range of spices, herbs, and trees known for their medicinal uses. Chilli peppers, a vegetable cum spice crop, are bestowed with natural bioactive compounds, flavonoids, capsaicinoids, phytochemicals, phytonutrients, and pharmacologically active compounds with potential health benefits. Such compounds manifest their functionality over solo-treatment by operating in synergy and consortium. Co-action of these compounds and nutrients make them potentially effective against coagulation, obesity, diabetes, inflammation, dreadful diseases, such as cancer, and microbial diseases, alongside having good anti-oxidants with scavenging ability to free radicals and oxygen. In recent times, capsaicinoids especially capsaicin can ameliorate important viral diseases, such as SARS-CoV-2. In addition, capsaicin provides an ability to chilli peppers to ramify as topical agents in pain-relief and also benefitting man as a potential effective anesthetic agent. Such phytochemicals involved not only make them useful and a much economical substitute to wonder/artificial drugs but can be exploited as obscene drugs for the production of novel stuffs. The responsibility of the TRPV1 receptor in association with capsaicin in mitigating chronic diseases has also been justified in this study. Nonetheless, medicinal studies pertaining to consumption of chilli peppers are limited and demand confirmation of the findings from animal studies. In this artifact, an effort has been made to address in an accessible format the nutritional and biomedical perspectives of chilli pepper, which could precisely upgrade and enrich our pharmaceutical industries towards human well-being. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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29 pages, 22531 KiB

Open AccessReview

Unveiling Natural and Semisynthetic Acylated Flavonoids: Chemistry and Biological Actions in the Context of Molecular Docking

by Dina M. El-Kersh, Rania F. Abou El-Ezz, Marwa Fouad and Mohamed A. Farag

Molecules 2022, 27(17), 5501; https://doi.org/10.3390/molecules27175501 - 26 Aug 2022

Cited by 8 | Viewed by 2715

Abstract

Acylated flavonoids are widely distributed natural metabolites in medicinal plants and foods with several health attributes. A large diversity of chemical structures of acylated flavonoids with interesting biological effects was reported from several plant species. Of these, 123 compounds with potential antimicrobial, antiparasitic, [...] Read more.

Acylated flavonoids are widely distributed natural metabolites in medicinal plants and foods with several health attributes. A large diversity of chemical structures of acylated flavonoids with interesting biological effects was reported from several plant species. Of these, 123 compounds with potential antimicrobial, antiparasitic, anti-inflammatory, anti-nociceptive, analgesic, and anti-complementary effects were selected from several databases including SCI-Finder, Scopus, Google Scholar, Science Direct, PubMed, and others. Some selected reported biologically active flavonoids were docked in the active binding sites of some natural enzymes, namely acetylcholinesterase, butyrylcholinesterase, α-amylase, α-glucosidase, aldose reductase, and HIV integrase, in an attempt to underline the key interactions that might be responsible for their biological activities. Full article

(This article belongs to the Special Issue Structural Modifications and Biological Activity of Natural Products and Their Derivatives Beneficial for Improving Human Health)

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