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5 pages, 207 KiB

Open AccessEditorial

Biological Activities of Natural Products III

by Halina Maria Ekiert and Agnieszka Szopa

Molecules 2023, 28(12), 4854; https://doi.org/10.3390/molecules28124854 - 19 Jun 2023

Viewed by 1384

Abstract

The search for natural products that display biological activity is invariably an attractive research area for scientific centers and teams from around the world [...] Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

Research

Jump to: Editorial, Review

13 pages, 3850 KiB

Open AccessArticle

Assessment of the Anticancer Effect of Chlorojanerin Isolated from Centaurothamnus maximus on A549 Lung Cancer Cells

by Omar Noman, Fahd A. Nasr, Mohammad Z. Ahmed, Md Tabish Rehman, Wajhul Qamar, Ali S. Alqahtani and Sebastian Guenther

Molecules 2023, 28(7), 3061; https://doi.org/10.3390/molecules28073061 - 29 Mar 2023

Cited by 4 | Viewed by 1782

Abstract

The goal of this study was to assess the anticancer efficacy of chlorojanerin against various cancer cells. The effects of chlorojanerin on cell cytotoxicity, cell cycle arrest, and cell apoptosis were examined using MTT assay, propidium iodide staining, and FITC Annexin V assay. [...] Read more.

The goal of this study was to assess the anticancer efficacy of chlorojanerin against various cancer cells. The effects of chlorojanerin on cell cytotoxicity, cell cycle arrest, and cell apoptosis were examined using MTT assay, propidium iodide staining, and FITC Annexin V assay. RT-PCR was employed to determine the expression levels of apoptosis-related genes. Furthermore, docking simulations were utilized to further elucidate the binding preferences of chlorojanerin with Bcl-2. According to MTT assay, chlorojanerin inhibited the proliferation of all tested cells in a dose-dependent manner with a promising effect against A549 lung cancer cells with an IC₅₀ of 10 µM. Cell growth inhibition by chlorojanerin was linked with G2/M phase cell cycle arrest in A549 treated cells. Flow cytometry analysis indicated that the proliferation inhibition effect of chlorojanerin was associated with apoptosis induction in A549 cells. Remarkably, chlorojanerin altered the expression of many genes involved in apoptosis initiation. Moreover, we determined that chlorojanerin fit into the active site of Bcl-2 according to the molecular docking study. Collectively, our results demonstrate that chlorojanerin mediated an anticancer effect involving cell cycle arrest and apoptotic cell death and, therefore, could potentially serve as a therapeutic agent in lung cancer treatment. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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26 pages, 5084 KiB

Open AccessArticle

Different Types of Hypericum perforatum cvs. (Elixir, Helos, Topas) In Vitro Cultures: A Rich Source of Bioactive Metabolites and Biological Activities of Biomass Extracts

by Inga Kwiecień, Natalizia Miceli, Elżbieta Kędzia, Emilia Cavò, Maria Fernanda Taviano, Ludger Beerhues and Halina Ekiert

Molecules 2023, 28(5), 2376; https://doi.org/10.3390/molecules28052376 - 4 Mar 2023

Cited by 8 | Viewed by 2337

Abstract

Microshoot agitated and bioreactor cultures (PlantForm bioreactors) of three Hypericum perforatum cultivars (Elixir, Helos, Topas) were maintained in four variants of Murashige and Skoog medium (MS) supplemented with 6-benzylaminopurine (BAP) and 1-naphthaleneacetic acid (NAA) (in the range of 0.1–3.0 mg/L). In both types [...] Read more.

Microshoot agitated and bioreactor cultures (PlantForm bioreactors) of three Hypericum perforatum cultivars (Elixir, Helos, Topas) were maintained in four variants of Murashige and Skoog medium (MS) supplemented with 6-benzylaminopurine (BAP) and 1-naphthaleneacetic acid (NAA) (in the range of 0.1–3.0 mg/L). In both types of in vitro cultures, the accumulation dynamics of phenolic acids, flavonoids, and catechins were investigated during 5- and 4-week growth cycles, respectively. The contents of metabolites in methanolic extracts from biomasses collected in 1-week intervals were estimated by HPLC. The highest total contents of phenolic acids, flavonoids, and catechins were 505, 2386, and 712 mg/100 g DW, respectively (agitated cultures of cv. Helos). The extracts from biomass grown under the best in vitro culture conditions were examined for antioxidant and antimicrobial activities. The extracts showed high or moderate antioxidant activity (DPPH, reducing power, and chelating activity assays), high activity against Gram-positive bacteria, and strong antifungal activity. Additionally, experiments with phenylalanine feeding (1 g/L) in agitated cultures were performed reaching the highest enhancement of the total contents of flavonoids, phenolic acids, and catechins on day 7 after the addition of the biogenetic precursor (2.33-, 1.73- and 1.33-fold, respectively). After feeding, the highest accumulation of polyphenols was detected in the agitated culture of cv. Elixir (4.48 g/100 g DW). The high contents of metabolites and the promising biological properties of the biomass extracts are interesting from a practical point of view. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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20 pages, 6066 KiB

Open AccessArticle

Superparamagnetic Iron-Oxide Nanoparticles Synthesized via Green Chemistry for the Potential Treatment of Breast Cancer

by Neha Tyagi, Priya Gupta, Zafar Khan, Yub Raj Neupane, Bharti Mangla, Nikita Mehra, Tanya Ralli, Abdulsalam Alhalmi, Asgar Ali, Omkulthom Al Kamaly, Asmaa Saleh, Fahd A. Nasr and Kanchan Kohli

Molecules 2023, 28(5), 2343; https://doi.org/10.3390/molecules28052343 - 3 Mar 2023

Cited by 15 | Viewed by 3465

Abstract

In the emerging field of nanomedicine, nanoparticles have been widely considered as drug carriers and are now used in various clinically approved products. Therefore, in this study, we synthesized superparamagnetic iron-oxide nanoparticles (SPIONs) via green chemistry, and the SPIONs were further coated with [...] Read more.

In the emerging field of nanomedicine, nanoparticles have been widely considered as drug carriers and are now used in various clinically approved products. Therefore, in this study, we synthesized superparamagnetic iron-oxide nanoparticles (SPIONs) via green chemistry, and the SPIONs were further coated with tamoxifen-conjugated bovine serum albumin (BSA-SPIONs-TMX). The BSA-SPIONs-TMX were within the nanometric hydrodynamic size (117 ± 4 nm), with a small poly dispersity index (0.28 ± 0.02) and zeta potential of −30.2 ± 0.09 mV. FTIR, DSC, X-RD, and elemental analysis confirmed that BSA-SPIONs-TMX were successfully prepared. The saturation magnetization (M_s) of BSA-SPIONs-TMX was found to be ~8.31 emu/g, indicating that BSA-SPIONs-TMX possess superparamagnetic properties for theragnostic applications. In addition, BSA-SPIONs-TMX were efficiently internalized into breast cancer cell lines (MCF-7 and T47D) and were effective in reducing cell proliferation of breast cancer cells, with IC₅₀ values of 4.97 ± 0.42 μM and 6.29 ± 0.21 μM in MCF-7 and T47D cells, respectively. Furthermore, an acute toxicity study on rats confirmed that these BSA-SPIONs-TMX are safe for use in drug delivery systems. In conclusion, green synthesized superparamagnetic iron-oxide nanoparticles have the potential to be used as drug delivery carriers and may also have diagnostic applications. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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19 pages, 3851 KiB

Open AccessArticle

The Anti-Obesity and Anti-Steatotic Effects of Chrysin in a Rat Model of Obesity Mediated through Modulating the Hepatic AMPK/mTOR/lipogenesis Pathways

by Ghaleb Oriquat, Inas M. Masoud, Maher A. Kamel, Hebatallah Mohammed Aboudeya, Marwa B. Bakir and Sara A. Shaker

Molecules 2023, 28(4), 1734; https://doi.org/10.3390/molecules28041734 - 11 Feb 2023

Cited by 13 | Viewed by 2912

Abstract

Background: Obesity is a complex multifactorial disease characterized by excessive adiposity, and is linked to an increased risk of nonalcoholic fatty liver disease (NAFLD). Flavonoids are natural polyphenolic compounds that exert interesting pharmacological effects as antioxidant, anti-inflammatory, and lipid-lowering agents. In the present [...] Read more.

Background: Obesity is a complex multifactorial disease characterized by excessive adiposity, and is linked to an increased risk of nonalcoholic fatty liver disease (NAFLD). Flavonoids are natural polyphenolic compounds that exert interesting pharmacological effects as antioxidant, anti-inflammatory, and lipid-lowering agents. In the present study, we investigated the possible therapeutic effects of the flavonoid chrysin on obesity and NAFLD in rats, and the role of AMP-activated protein kinase (AMPK)/mammalian target of rapamycin (mTOR) pathways in mediating these effects. Method: Thirty-two Wistar male rats were divided into two groups: the control group and the obese group. Obesity was induced by feeding with an obesogenic diet for 3 months. The obese rats were subdivided into four subgroups, comprising an untreated group, and three groups treated orally with different doses of chrysin (25, 50, and 75 mg/kg/day for one month). Results revealed that chrysin treatment markedly ameliorated the histological changes and significantly and dose-dependently reduced the weight gain, hyperglycemia, and insulin resistance in the obese rats. Chrysin, besides its antioxidant boosting effects (increased GSH and decreased malondialdehyde), activated the AMPK pathway and suppressed the mTOR and lipogenic pathways, and stimulated expression of the genes controlling mitochondrial biogenesis in the hepatic tissues in a dose-dependent manner. In conclusion, chrysin could be a promising candidate for the treatment of obesity and associated NAFLD, aiding in attenuating weight gain and ameliorating glucose and lipid homeostasis and adipokines, boosting the hepatic mitochondrial biogenesis, and modulating AMPK/mTOR/SREBP-1c signaling pathways. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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20 pages, 4924 KiB

Open AccessArticle

GC/MS Analysis, Cytotoxicity, and Antiviral Activities of Annona glabra Hexane Extract Supported by In Silico Study

by Dalia M. Soleman, Omayma A. Eldahshan, Mona H. Ibrahim, Hanan A. Ogaly, Heba M. Galal, Gaber El-Saber Batiha and Rawah H. Elkousy

Molecules 2023, 28(4), 1628; https://doi.org/10.3390/molecules28041628 - 8 Feb 2023

Cited by 5 | Viewed by 3180

Abstract

Annona glabra Linn is employed in conventional medicine to treat a number of human disorders, including cancer and viruses. In the present investigation, the significant phytochemical components of Annona glabra hexane extract were identified using gas chromatography–mass spectrometry (GC-MS) analysis. Three major compounds [...] Read more.

Annona glabra Linn is employed in conventional medicine to treat a number of human disorders, including cancer and viruses. In the present investigation, the significant phytochemical components of Annona glabra hexane extract were identified using gas chromatography–mass spectrometry (GC-MS) analysis. Three major compounds were identified in the hexane extract: tritriacontane (30.23%), 13, 17-dimethyl-tritriacontane (22.44%), and limonene (18.97%). MTT assay was used to assess the cytotoxicity of the extract on six human cancer cell lines including liver (HepG-2), pancreas (PANC-1), lung (A-549), breast (MCF-7, HTB-22), prostate (PC-3), and colon (CACO-2, ATB-37). The extract exhibited significant cytotoxic activity against both CACO-2 and A-549 cancer cell lines (IC₅₀ = 47 ± 0.74 μg/mL and 56.82 ± 0.92 μg/mL) in comparison with doxorubicin (IC₅₀ = 31.91 ± 0.81 μg/mL and 23.39 ± 0.43 μg/mL) and of SI of 3.8 and 3.1, respectively. It also induced moderate-to-weak activities against the other cancerous cell lines: PC-3, PANC-1, MCF-7, and HepG-2 (IC₅₀ = 81.86 ± 3.26, 57.34 ± 0.77, 80.31 ± 4.13, and 57.01 ± 0.85 μg/mL) in comparison to doxorubicin (IC₅₀ = 32.9 ± 1.74, 19.07 ± 0.2, 15.48 ± 0.84 and 5.4 ± 0.22 μg/mL, respectively) and SI of 2.2, 3.1, 2.2, and 3.1, respectively. In vitro anti-HSV1 (Herpes simplex 1 virus) and HAV (Hepatitis A virus) activity was evaluated using MTT colorimetric assay with three different protocols to test protective, anti-replicative, and anti-infective antiviral activities, and three separate replications of each experiment were conducted. The plant extract showed promising protective and virucidal activity against HSV1 with no significant difference with acyclovir (79.55 ± 1.67 vs. 68.44 ± 7.62 and 70.91 ± 7.02 vs. 83.76 ± 5.67), while it showed mild protective antiviral activity against HAV (48.08 ±3.46) with no significant difference vs. acyclovir (36.89 ± 6.61). The selected main compounds were examined for their bioactivity through in silico molecular docking, which exhibited that limonene could possess the strongest antiviral properties. These findings support Annona glabra’s conventional use, which is an effective source of antiviral and anticancer substances that could be used in pharmaceuticals. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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12 pages, 1013 KiB

Open AccessArticle

Phytochemical Compounds, Acute Toxicity, Anti-Inflammatory and Antioxidant Activities of Thymus leptobotrys Murb Essential Oil

by Asmaa Oubihi, Fatima Zahrae Ballaoui, Hamada Imtara, Hassna Jaber, Abdessamad Ettouil, Sara Haida, Mohammed Ouhssine, Omar M. Noman, Ramzi A. Mothana, Mahmoud Tarayrah and Zineb Guessous

Molecules 2023, 28(3), 1355; https://doi.org/10.3390/molecules28031355 - 31 Jan 2023

Cited by 5 | Viewed by 2377

Abstract

The present study was conducted to evaluate the acute toxicity and anti-inflammatory effect in vivo, as well as the antioxidant activity, of the essential oil of Thymus leptobotrys Murb. The results indicate that the tested essential oil is non-toxic, with an estimated [...] Read more.

The present study was conducted to evaluate the acute toxicity and anti-inflammatory effect in vivo, as well as the antioxidant activity, of the essential oil of Thymus leptobotrys Murb. The results indicate that the tested essential oil is non-toxic, with an estimated LD50 of 2500 mg kg⁻¹ of mice body weight. The anti-inflammatory test revealed that, at a dose of 200 mg kg⁻¹, the essential oil reduced rat paw edemas by 89.59% within 3 h of oral administration, this reduction in edema size was greater than that obtained with indomethacin (75.78%). The antioxidant activity (IC50) of Thymus leptobotrys Murb essential oil was 346.896 µg mL⁻¹ and 861.136 mg Trolox equivalent/g essential oil in the 2.2-diphenyl1-picryl-hydrazyl radical scavenging capacity (DPPH) and Trolox equivalent antioxidant capacity (TEAC) assays, respectively. The toxicity test reveals an LD₅₀ greater than 2500 mg kg⁻¹ of body weight of mice which classifies it within category 5 of non-toxic substances that can be administered orally. These results suggest that the essential oil of Thymus leptobotrys Murb is not toxic, and it represents a valuable source of anti-inflammatory and antioxidant metabolites. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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14 pages, 1796 KiB

Open AccessArticle

Metabolite Profiling of Gardenia jasminoides Ellis In Vitro Cultures with Different Levels of Differentiation

by Gergana Krasteva, Strahil Berkov, Atanas Pavlov and Vasil Georgiev

Molecules 2022, 27(24), 8906; https://doi.org/10.3390/molecules27248906 - 14 Dec 2022

Cited by 3 | Viewed by 2284

Abstract

Gardenia jasminoides Ellis is an aromatic and medicinal plant of high economic value. Much research has focused on the phytochemistry and biological activities of Gardenia fruit extracts; however, the potential of the Gardenia plant in vitro cultures used as mass production systems of [...] Read more.

Gardenia jasminoides Ellis is an aromatic and medicinal plant of high economic value. Much research has focused on the phytochemistry and biological activities of Gardenia fruit extracts; however, the potential of the Gardenia plant in vitro cultures used as mass production systems of valuable secondary metabolites has been understudied. This paper presents data on metabolite profiling (GC/MS and HPLC), antioxidant activities (DPPH, TEAC, FRAP, and CUPRAC), and SSR profiles of G. jasminoides plant leaves and in vitro cultures with different levels of differentiation (shoots, callus, and cell suspension). The data show strong correlations (r = 0.9777 to r = 0.9908) between antioxidant activity and the concentrations of chlorogenic acid, salicylic acid, rutin, and hesperidin. Eleven co-dominant microsatellite simple sequence repeats (SSRs) markers were used to evaluate genetic variations (average PIC = 0.738 ± 0.153). All of the investigated Gardenia in vitro cultures showed high genetic variabilities (average Na = 5.636 ± 2.157, average Ne = 3.0 ± 1.095). This is the first report on a study on metabolite profiles, antioxidant activities, and genetic variations of G. jasminoides in vitro cultures with different levels of differentiation. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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10 pages, 677 KiB

Open AccessArticle

Glucosinolates of Sisymbrium officinale and S. orientale

by Azra Đulović, Marijana Popović, Franko Burčul, Vedrana Čikeš Čulić, Sandra Marijan, Mirko Ruščić, Nikolina Anđelković and Ivica Blažević

Molecules 2022, 27(23), 8431; https://doi.org/10.3390/molecules27238431 - 2 Dec 2022

Cited by 7 | Viewed by 1776

Abstract

Glucosinolates (GSLs) from Sysimbrium officinale and S. orientale were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS. Eight GSLs were identified in S. officinale, including Val-derived (glucoputranjivin) and Trp-derived (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin) as the major ones followed by Leu-derived [...] Read more.

Glucosinolates (GSLs) from Sysimbrium officinale and S. orientale were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS. Eight GSLs were identified in S. officinale, including Val-derived (glucoputranjivin) and Trp-derived (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin) as the major ones followed by Leu-derived (Isobutyl GSL), Ile-derived (glucocochlearin) and Phe/Tyr-derived (glucosinalbin). Different S. orientale plant parts contained six GSLs, with Met-derived (progoitrin, epiprogoitrin, and gluconapin) and homoPhe-derived (gluconasturtiin) as the major ones, followed by glucosinalbin and neoglucobrassicin. GSL breakdown products obtained by hydrodistillation (HD) and microwave-assisted distillation from S. officinale, as well as isopropyl isothiocyanate, as the major volatile in both isolates, were tested for their cytotoxic activity using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Generally, all volatile isolates showed similar activity toward the three cancer cell lines. The best activity was shown by isopropyl isothiocyanate at a concentration of 100 µg/mL after 72 h of incubation, with 53.18% for MDA-MB-231, 56.61% for A549, and 60.02% for the T24 cell line. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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13 pages, 3502 KiB

Open AccessArticle

Anticancer Effects of Propolis Extracts Obtained with the Cold Separation Method on PC-3 and DU-145 Prostate Cancer Cell Lines

by Marek Gogacz, Jerzy Peszke, Dorota Natorska-Chomicka, Anna Makuch-Kocka and Katarzyna Dos Santos Szewczyk

Molecules 2022, 27(23), 8245; https://doi.org/10.3390/molecules27238245 - 26 Nov 2022

Cited by 6 | Viewed by 1967

Abstract

Plant extracts are increasingly tested for their biological activity and interactions with neoplastic cells. One of such sources of biologically active substances is propolis. This product has been known for thousands of years and is widely used in alternative, folk medicine. Articles describing [...] Read more.

Plant extracts are increasingly tested for their biological activity and interactions with neoplastic cells. One of such sources of biologically active substances is propolis. This product has been known for thousands of years and is widely used in alternative, folk medicine. Articles describing its effects on the metabolism and cell signaling pathways of neoplastic cells derived from different organs are also published more and more frequently. The purpose of our study was to evaluate the biological activity of propolis extract produced with the cold separation method into hormone-dependent and hormone-independent prostate cancer cell lines. In our study, the propolis extracts showed at least an inhibitory effect on the growth of PC-3 and DU-145 neoplastic cells. Our results suggest that propolis extracts obtained with the cold separation method may be considered as promising compounds for the production of health-promoting supplements. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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14 pages, 881 KiB

Open AccessArticle

Optimization of Extraction Conditions and Cytotoxic Activity of Rapanone in Comparison to Its Homologue, Embelin

by Dagmara Wróbel-Biedrawa, Agnieszka Galanty, Paweł Zagrodzki and Irma Podolak

Molecules 2022, 27(22), 7912; https://doi.org/10.3390/molecules27227912 - 16 Nov 2022

Cited by 2 | Viewed by 1752

Abstract

Rapanone is a plant-derived simple alkyl-dihydroxybenzoquinone structurally close to embelin, a well-known cytotoxic agent. The pharmacological characterization of rapanone is still incomplete, and to fill the data gap, a good source for its acquisition is required to conduct further research. This study aimed [...] Read more.

Rapanone is a plant-derived simple alkyl-dihydroxybenzoquinone structurally close to embelin, a well-known cytotoxic agent. The pharmacological characterization of rapanone is still incomplete, and to fill the data gap, a good source for its acquisition is required to conduct further research. This study aimed to optimize the conditions for the extraction of rapanone from the leaves of white-berried Ardisia crenata Sims. For this purpose, three methods were employed: heat reflux (HRE), shaking (SE), and ultrasound-assisted extraction (UAE), and such parameters as the extraction time, solvent, and the number of extractions from the same sample were set as experimental variables. Furthermore, cytotoxic activity toward prostate cancer, thyroid cancer, and colorectal carcinoma cell lines was investigated and compared with doxorubicin and embelin. The most effective and economical method for the extraction of rapanone was shown to be 20 min UAE with ethyl acetate or chloroform. Rapanone exhibited high cytotoxic activity against PC3 (IC₅₀ = 6.50 μg/mL), Du145 (IC₅₀ = 7.68 μg/mL), FTC133 (IC₅₀ = 6.01 μg/mL), 8505C (IC₅₀ = 7.84 μg/mL), and Caco-2 (IC₅₀ = 8.79 μg/mL) cell lines after 24 h and against the HT29 cell line after 48 h (IC₅₀ = 11.67 μg/mL). Furthermore, it revealed a more favorable safety profile than either its homologue, embelin, or doxorubicin. The set of optimal extraction parameters obtained may be utilized for scientific and industrial purposes to achieve the best rapanone yield. Moreover, this benzoquinone revealed a high cytotoxic activity with good selectivity. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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19 pages, 1868 KiB

Open AccessArticle

Assessment of Cucurbita spp. Peel Extracts as Potential Sources of Active Substances for Skin Care and Dermatology

by Katarzyna Gaweł-Bęben, Karolina Czech, Marcelina Strzępek-Gomółka, Marcin Czop, Monika Szczepanik, Anna Lichtarska and Wirginia Kukula-Koch

Molecules 2022, 27(21), 7618; https://doi.org/10.3390/molecules27217618 - 6 Nov 2022

Cited by 8 | Viewed by 3170

Abstract

By-products of cultivated plants are one of the major environmental concerns worldwide. Due to the high concentration of bioactive chemicals, such waste may be considered hazardous due to the interference with the plant growth, deterioration of the drinking water quality or toxic effects [...] Read more.

By-products of cultivated plants are one of the major environmental concerns worldwide. Due to the high concentration of bioactive chemicals, such waste may be considered hazardous due to the interference with the plant growth, deterioration of the drinking water quality or toxic effects on sensitive marine organisms. Moreover, plant-derived by-products, with proper handling, may represent a low-cost source of bioactive compounds potentially important for pharmaceutical and cosmetics industries. The aim of the study was to evaluate the phytochemical composition, antioxidant activity, the influence of tyrosinase activity, in vitro sun protecting factor and cytotoxicity of 15 extracts from peels of five cultivars of Cucurbita maxima and C. moschata. The extracts were prepared using “green solvents” (water, 50% propylene glycol, and 20% ethanol) and ultrasound-assisted extraction. The performed analysis showed that the peel extracts from various cultivars differ significantly in respect to the phytochemical content and activity. The type of solvent also had a significant impact on the extract’s composition and bioactivity. Aqueous peel extracts contained the highest amounts of flavonoids, showed the greatest antioxidant potential and the most significant in vitro SPF values. In vitro studies showed that the analyzed peel extracts are not cytotoxic for human keratinocytes up to the concentration of 1000 µg/mL and thus might be considered as non-irritant for the skin. The study confirms the potential application of peel extracts from Cucurbita spp. cultivars in cosmetic products. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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13 pages, 1509 KiB

Open AccessArticle

Synthesis and Biological Activity of Novel Oxazinyl Flavonoids as Antiviral and Anti-Phytopathogenic Fungus Agents

by Yucong Ma, Lu Wang, Aidang Lu and Wei Xue

Molecules 2022, 27(20), 6875; https://doi.org/10.3390/molecules27206875 - 13 Oct 2022

Cited by 9 | Viewed by 1841

Abstract

A series of oxazinyl flavonoids were synthesized on the basis of flavone. The structures of all target compounds were characterized by ¹H NMR, ¹³C NMR, and HRMS. The effect of the different substituent on the N-position of oxazinyl flavonoids against tobacco [...] Read more.

A series of oxazinyl flavonoids were synthesized on the basis of flavone. The structures of all target compounds were characterized by ¹H NMR, ¹³C NMR, and HRMS. The effect of the different substituent on the N-position of oxazinyl flavonoids against tobacco mosaic virus (TMV) activities and plant pathogen activities was systematically investigated. In vivo anti-TMV activity showed that most of the compounds showed moderate-to-excellent antiviral activities against TMV at 500 μg/mL. Compounds 6b, 6d, 6j–6k, and 6n–6q showed better antiviral activities than ribavirin (a commercially available antiviral agent) and apigenin. In particular, compounds 6n and 6p even displayed slightly higher activities than ningnanmycin, which were expected to become new antiviral candidates. Antiviral mechanism research by molecular docking exhibited that compounds 6n and 6p could interact with TMV CP and inhibit virus assembly. Then, the antifungal activities of these compounds against six kinds of plant pathogenic fungi were tested, and the results showed that these oxazinyl flavonoids had broad-spectrum fungicidal activities. Compounds 6h exhibited antifungal activity of up to 91% against Physalospora piricola and might become a candidate drug for new fungicides. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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13 pages, 2161 KiB

Open AccessArticle

Pomegranate Flower Extract—The Health-Promoting Properties Optimized by Application of the Box–Behnken Design

by Anna Gościniak, Aleksandra Bazan-Woźniak, Robert Pietrzak and Judyta Cielecka-Piontek

Molecules 2022, 27(19), 6616; https://doi.org/10.3390/molecules27196616 - 5 Oct 2022

Cited by 7 | Viewed by 2480

Abstract

Herbal raw materials with antidiabetic activity can be a valuable support to therapy. An optimized extraction process allows for the best possible health-promoting effect. Box–Behnken design was employed to optimize the content of methanol used in the extraction mixture, its time, and temperature. [...] Read more.

Herbal raw materials with antidiabetic activity can be a valuable support to therapy. An optimized extraction process allows for the best possible health-promoting effect. Box–Behnken design was employed to optimize the content of methanol used in the extraction mixture, its time, and temperature. The aim of this study was to enhance the efficiency of the pomegranate flowers extraction process in order to obtain extracts with the highest enzyme inhibition power (α-amylase and α-glucosidase), which is important for the antidiabetic effect and the highest antioxidant activity (DPPH assay). In the Box–Behnken design model, the content of pelargonidin-3,5-glucoside–anthocyanin compound that is associated with antidiabetic activity was also optimized as a variable associated with the action profile of pomegranate flower extracts. The process optimization carried out in this study provides a basis for further research using the pomegranate flower extract with the most potent desired properties, essential for supporting diabetes treatment based on pomegranate flowers. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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13 pages, 4220 KiB

Open AccessArticle

Biological Activity of Copaiba in Damage to the Alveolar Bone in a Model of Periodontitis Induced in Rats

by Vinicius Ruan Neves dos Santos, João Victor da Silva Motta, Deborah Ribeiro Frazão, Railson de Oliveira Ferreira, Deiweson Souza-Monteiro, Daiane Claydes Baia-da-Silva, Paulo Fernando Santos Mendes, Leonardo Oliveira Bittencourt, João Daniel Mendonça de Moura, Osmar Alves Lameira, Gabriela de Souza Balbinot, Fabrício Mezzomo Collares, Cassiano Kuchenbecker Rösing and Rafael Rodrigues Lima

Molecules 2022, 27(19), 6255; https://doi.org/10.3390/molecules27196255 - 23 Sep 2022

Cited by 5 | Viewed by 3154

Abstract

Several studies have investigated the effects of natural products in the treatment of diseases. Traditional Amazonian populations commonly use copaiba due to its well-known anti-inflammatory, antibacterial, and healing properties. In this study, we aimed to investigate the effects of systemic administration of copaiba [...] Read more.

Several studies have investigated the effects of natural products in the treatment of diseases. Traditional Amazonian populations commonly use copaiba due to its well-known anti-inflammatory, antibacterial, and healing properties. In this study, we aimed to investigate the effects of systemic administration of copaiba oleoresin (Copaifera reticulata Ducke) on ligature-induced periodontitis in rats. To do so, 21 adult rats were divided into three groups (n = 7 each): a control group, ligature-induced periodontitis group, and ligature-induced periodontitis group treated with copaiba oleoresin (200 mg/kg/day). The ligature remained from day 0 to 14, and the copaiba oleoresin was administered via oral gavage during the last seven days. On day 14, the animals were euthanized, and mandibles were collected for histopathological evaluation and microcomputed tomography analysis. Our data showed that the administration of copaiba considerably reduced the inflammatory profile. Moreover, copaiba oleoresin limited alveolar bone loss, increased trabecular thickness and bone-to-tissue volume ratio, and decreased the number of trabeculae compared with those of the untreated experimental periodontitis group. Our findings provide pioneering evidence that supports the potential of copaiba oleoresin in reducing periodontitis-induced alveolar bone damage in rats. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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12 pages, 2419 KiB

Open AccessArticle

Phytoecdysteroids from Serratula coronata L. for Psoriatic Skincare

by Anna Kroma, Mariola Pawlaczyk, Agnieszka Feliczak-Guzik, Maria Urbańska, Dorota Jenerowicz, Agnieszka Seraszek-Jaros, Małgorzata Kikowska and Justyna Gornowicz-Porowska

Molecules 2022, 27(11), 3471; https://doi.org/10.3390/molecules27113471 - 27 May 2022

Cited by 3 | Viewed by 2584

Abstract

Phytoecdysones from Serratula coronata seem to be promising agents for skincare in patients with psoriasis. The aim of the study was to determine the effects of creams containing the extract of S. coronata on psoriatic lesions. Creams with different formulas were prepared: 0-Lekobaza [...] Read more.

Phytoecdysones from Serratula coronata seem to be promising agents for skincare in patients with psoriasis. The aim of the study was to determine the effects of creams containing the extract of S. coronata on psoriatic lesions. Creams with different formulas were prepared: 0-Lekobaza^®, 1-Lekobaza^®, S. coronata, 2-Lekobaza^®, Salicylic acid, 3-Lekobaza^®, S. coronata, Salicylic acid. After examination of skin penetration and biosafety, the designated cream was applied twice daily for 6 weeks on 72 psoriatic plaques located on elbows or knees. The lesions were assessed at baseline and follow-up of 6 weeks. The lesions area was measured, and severity of scaling, erythema, and infiltration was assessed using a 5-point scale (from 0—none to 4—very severe). Skin hydration and structure, pH, transepidermal water loss, erythema, and melanin index were analyzed instrumentally. Creams 1, 2, and 3 significantly reduced the area of psoriatic plaques. Improvement in erythema and infiltration was observed for creams 1 and 3. Creams 1–3 reduced scaling. Our study confirmed a beneficial effect of creams containing S. coronata extract on psoriatic lesions. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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Review

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24 pages, 4895 KiB

Open AccessReview

Schisandra henryi—A Rare Species with High Medicinal Potential

by Karolina Jafernik, Halina Ekiert and Agnieszka Szopa

Molecules 2023, 28(11), 4333; https://doi.org/10.3390/molecules28114333 - 25 May 2023

Cited by 4 | Viewed by 1926

Abstract

Schisandra henryi (Schisandraceae) is a plant species endemic to Yunnan Province in China and is little known in Europe and America. To date, few studies, mainly performed by Chinese researchers, have been conducted on S. henryi. The chemical composition of this plant [...] Read more.

Schisandra henryi (Schisandraceae) is a plant species endemic to Yunnan Province in China and is little known in Europe and America. To date, few studies, mainly performed by Chinese researchers, have been conducted on S. henryi. The chemical composition of this plant is dominated by lignans (dibenzocyclooctadiene, aryltetralin, dibenzylbutane), polyphenols (phenolic acids, flavonoids), triterpenoids, and nortriterpenoids. The research on the chemical profile of S. henryi showed a similar chemical composition to S. chinensis—a globally known pharmacopoeial species with valuable medicinal properties whichis the best-known species of the genus Schisandra. The whole genus is characterized by the presence of the aforementioned specific dibenzocyclooctadiene lignans, known as “Schisandra lignans”. This paper was intended to provide a comprehensive review of the scientific literature published on the research conducted on S. henryi, with particular emphasis on the chemical composition and biological properties. Recently, a phytochemical, biological, and biotechnological study conducted by our team highlighted the great potential of S. henryi in in vitro cultures. The biotechnological research revealed the possibilities of the use of biomass from S. henryi as an alternative to raw material that cannot be easily obtained from natural sites. Moreover, the characterization of dibenzocyclooctadiene lignans specific to the Schisandraceae family was provided. Except for several scientific studies which have confirmed the most valuable pharmacological properties of these lignans, hepatoprotective and hepatoregenerative, this article also reviews studies that have confirmed the anti-inflammatory, neuroprotective, anticancer, antiviral, antioxidant, cardioprotective, and anti-osteoporotic effects and their application for treating intestinal dysfunction. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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12 pages, 1170 KiB

Open AccessReview

Effect of the Citrus Flavone Nobiletin on Circadian Rhythms and Metabolic Syndrome

by Gael N. N. Neba Ambe, Carlo Breda, Avninder Singh Bhambra and Randolph R. J. Arroo

Molecules 2022, 27(22), 7727; https://doi.org/10.3390/molecules27227727 - 10 Nov 2022

Cited by 8 | Viewed by 2803

Abstract

The importance of the circadian clock in maintaining human health is now widely acknowledged. Dysregulated and dampened clocks may be a common cause of age-related diseases and metabolic syndrome Thus, circadian clocks should be considered as therapeutic targets to mitigate disease symptoms. This [...] Read more.

The importance of the circadian clock in maintaining human health is now widely acknowledged. Dysregulated and dampened clocks may be a common cause of age-related diseases and metabolic syndrome Thus, circadian clocks should be considered as therapeutic targets to mitigate disease symptoms. This review highlights a number of dietary compounds that positively affect the maintenance of the circadian clock. Notably the polymethoxyflavone nobiletin has shown some encouraging results in pre-clinical experiments. Although many more experiments are needed to fully elucidate its exact mechanism of action, it is a promising candidate with potential as a chronotherapeutic agent. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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19 pages, 2222 KiB

Open AccessFeature PaperReview

Natural Compounds in the Battle against Microorganisms—Linalool

by Wanda Mączka, Anna Duda-Madej, Małgorzata Grabarczyk and Katarzyna Wińska

Molecules 2022, 27(20), 6928; https://doi.org/10.3390/molecules27206928 - 15 Oct 2022

Cited by 31 | Viewed by 7166

Abstract

The purpose of this article is to present recent studies on the antimicrobial properties of linalool, the mechanism of action on cells and detoxification processes. The current trend of employing compounds present in essential oils to support antibiotic therapy is becoming increasingly popular. [...] Read more.

The purpose of this article is to present recent studies on the antimicrobial properties of linalool, the mechanism of action on cells and detoxification processes. The current trend of employing compounds present in essential oils to support antibiotic therapy is becoming increasingly popular. Naturally occurring monoterpene constituents of essential oils are undergoing detailed studies to understand their detailed effects on the human body, both independently and in doses correlated with currently used pharmaceuticals. One such compound is linalool, which is commonly found in many herbs and is used to flavor black tea. This compound is an excellent fragrance additive for cosmetics, enhancing the preservative effect of the formulations used in them or acting as an anti-inflammatory on mild skin lesions. Previous studies have shown that it is extremely important due to its broad spectrum of biological activities, i.e., antioxidant, anti-inflammatory, anticancer, cardioprotective and antimicrobial. Among opportunistic hospital strains, it is most active against Gram-negative bacteria. The mechanism of action of linalool against microorganisms is still under intensive investigation. One of the key aspects of linalool research is biotransformation, through which its susceptibility to detoxification processes is determined. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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25 pages, 5783 KiB

Open AccessReview

A Review of Polygonatum Mill. Genus: Its Taxonomy, Chemical Constituents, and Pharmacological Effect Due to Processing Changes

by Lu Luo, Yixing Qiu, Limin Gong, Wei Wang and Ruiding Wen

Molecules 2022, 27(15), 4821; https://doi.org/10.3390/molecules27154821 - 28 Jul 2022

Cited by 24 | Viewed by 4090

Abstract

Ethnopharmacological relevance: The genus Polygonatum Tourn, ex Mill. contains numerous chemical components, such as steroidal saponins, polysaccharides, flavonoids, alkaloids, and others, it possesses diverse pharmacological activities, such as anti-aging, anti-tumor, immunological regulation, as well as blood glucose management and fat reducing properties. Aim [...] Read more.

Ethnopharmacological relevance: The genus Polygonatum Tourn, ex Mill. contains numerous chemical components, such as steroidal saponins, polysaccharides, flavonoids, alkaloids, and others, it possesses diverse pharmacological activities, such as anti-aging, anti-tumor, immunological regulation, as well as blood glucose management and fat reducing properties. Aim of the review: This study reviews the current state of research on the systematic categorization, chemical composition, pharmacological effects, and processing changes of the plants belonging to the genus Polygonatum, to provide a theoretical foundation for their scientific development and rational application. Materials and methods: The information was obtained by searching the scientific literature published between 1977 and 2022 on online databases (including PubMed, CNKI, SciFinder, and Web of Science) and other sources (such as the Chinese Pharmacopoeia 2020 edition, and Chinese herbal books). Results: The genus Polygonatum contains 79 species, and 233 bioactive chemical compounds were identified in them. The abundance of pharmacological activities, such as antioxidant activities, anti-fatigue activities, anti-inflammatory activities, etc., were revealed for the representatives of this genus. In addition, there are numerous processing methods, and many chemical constituents and pharmacological activities change after the unappropriated processing. Conclusions: This review summarizes the taxonomy classification, chemical composition, pharmacological effects, and processing of the plants belonging to the genus Polygonatum, providing references and research tendencies for plant-based drug development and further clinical applications. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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23 pages, 982 KiB

Open AccessReview

Potential Natural Biomolecules Targeting JAK/STAT/SOCS Signaling in the Management of Atopic Dermatitis

by Spandana Rajendra Kopalli, Venkata Prakash Annamneedi and Sushruta Koppula

Molecules 2022, 27(14), 4660; https://doi.org/10.3390/molecules27144660 - 21 Jul 2022

Cited by 19 | Viewed by 4846

Abstract

Atopic dermatitis (AD) is a chronic inflammatory skin disease caused by the dysregulation of cytokines and other immune mediators. JAK/STAT is a classical signal transduction pathway involved in various biological processes, and its dysregulation contributes to the key aspects of AD pathogenesis. Suppressor [...] Read more.

Atopic dermatitis (AD) is a chronic inflammatory skin disease caused by the dysregulation of cytokines and other immune mediators. JAK/STAT is a classical signal transduction pathway involved in various biological processes, and its dysregulation contributes to the key aspects of AD pathogenesis. Suppressor of cytokine signaling (SOCS) proteins negatively regulate the immune-related inflammatory responses mediated by the JAK/STAT pathway. JAK/STAT-mediated production of cytokines including IL-4, IL-13, IL-31, and TSLP inhibits the expression of important skin barrier proteins and triggers pruritus in AD. The expression of SOCS proteins regulates the JAK-mediated cytokines and facilitates maintaining the skin barrier disruptions seen in AD. STATs are crucial in dendritic-cell-activated Th2 cell differentiation in the skin, releasing inflammatory cytokines, indicating that AD is a Th2-mediated skin disorder. SOCS proteins aid in balancing Th1/Th2 cells and, moreover, regulate the onset and maintenance of Th2-mediated allergic responses by reducing the Th2 cell activation and differentiation. SOCS proteins play a pivotal role in inflammatory cytokine-signaling events that act via the JAK/STAT pathway. Therapies relying on natural products and derived biomolecules have proven beneficial in AD when compared with the synthetic regimen. In this review, we focused on the available literature on the potential natural-product-derived biomolecules targeting JAK/STAT/SOCS signaling, mainly emphasizing the SOCS family of proteins (SOCS1, SOCS3, and SOCS5) acting as negative regulators in modulating JAK/STAT-mediated responses in AD pathogenesis and other inflammatory disorders. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products III)

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