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Pharmacological Evaluation and Phytochemical Analysis of Natural Products

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

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 20154

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Prof. Dr. Sergio Faloni de Andrade

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Guest Editor

Research Center for Biosciences and Health Technologies (CBIOS), Lusofona University, Lisbon, Portugal
Interests: natural products; inflammation; ulcer; colitis; microcirculation, skin diseases
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Rivaldo Niero

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Guest Editor

Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade do vale do Itajaí, Itajái, Brazil
Interests: natural products; phytochemistry; secondary metabolites; extraction methods; spectroscopy

Special Issue Information

Dear Colleagues,

Natural products have been used by humans since antiquity for several purposes. It is believed that human beings have used natural components and their derived molecules to treat disorders in the last 60,000 years, and currently, the majority of new drugs are discovered from natural products (secondary metabolites) and/or their derivatives. Thus, there is no denying the contribution of research dedicated to the pharmacological evaluation and phytochemical analysis of natural products to the development of new drugs to treat the different diseases which affect human beings.

As Guest Editors of this Special Issue of Molecules, we are glad to invite researchers working in any field involving phytochemistry and pharmacology of natural products to publish your papers here. Original articles covering in vitro, in silico, preclinical, and clinical studies, as well as review articles, are welcome.

Prof. Dr. Sergio Faloni de Andrade
Prof. Dr. Rivaldo Niero
Guest Editors

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Keywords

natural products
phytochemistry
pharmacological evaluation
secondary metabolites
phytochemical analysis

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Published Papers (7 papers)

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Research

16 pages, 2146 KiB

Open AccessArticle

Chemical Composition, Antioxidant, and Antitumor Activity of Fucoidan from the Brown Alga Dictyota dichotoma

by Mostafa M. El-Sheekh, Fatma Ward, Mohamed A. Deyab, Majid Al-Zahrani and Hussein E. Touliabah

Molecules 2023, 28(20), 7175; https://doi.org/10.3390/molecules28207175 - 19 Oct 2023

Cited by 8 | Viewed by 2559

Abstract

Brown macroalgae are a rich source of fucoidans with many pharmacological uses. This research aimed to isolate and characterize fucoidan from Dictyota dichotoma var. dichotoma (Hudson) J.V. Lamouroux and evaluate in vitro its antioxidant and antitumor potential. The fucoidan yield was 0.057 g/g algal dry wt with a molecular weight of about 48.6 kDa. In terms of fucoidan composition, the sulfate, uronic acid, and protein contents were 83.3 ± 5.20 mg/g fucoidan, 22.5 ± 0.80 mg/g fucoidan, and 26.1 ± 1.70 mg/g fucoidan, respectively. Fucose was the primary sugar component, as were glucose, galactose, mannose, xylose, and glucuronic acid. Fucoidan exhibited strong antioxidant potential that increased by more than 3 times with the increase in concentration from 0.1 to 5.0 mg/mL. Moreover, different concentrations of fucoidan (0.05–1 mg/mL) showed their ability to decrease the viability of Ehrlich ascites carcinoma cells in a time-dependent manner. These findings provided a fast method to obtain an appreciable amount of natural fucoidan with established structural characteristics as a promising compound with pronounced antioxidant and anticancer activity. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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14 pages, 1865 KiB

Open AccessArticle

Antinociceptive Effect of a p-Cymene/β-Cyclodextrin Inclusion Complex in a Murine Cancer Pain Model: Characterization Aided through a Docking Study

by Wagner B. R. Santos, Lícia T. S. Pina, Marlange A. de Oliveira, Lucas A. B. O. Santos, Marcus V. A. Batista, Gabriela G. G. Trindade, Marcelo C. Duarte, Jackson R. G. S. Almeida, Lucindo J. Quintans-Júnior, Jullyana S. S. Quintans, Mairim R. Serafini, Henrique D. M. Coutinho, Grażyna Kowalska, Tomasz Baj, Radosław Kowalski and Adriana G. Guimarães

Molecules 2023, 28(11), 4465; https://doi.org/10.3390/molecules28114465 - 31 May 2023

Cited by 6 | Viewed by 1681

Abstract

Pain is one of the most prevalent and difficult to manage symptoms in cancer patients, and conventional drugs present a range of adverse reactions. The development of β-cyclodextrins (β-CD) complexes has been used to avoid physicochemical and pharmacological limitations due to the lipophilicity of compounds such as p-Cymene (PC), a monoterpene with antinociceptive effects. Our aim was to obtain, characterize, and measure the effect of the complex of p-cymene and β-cyclodextrin (PC/β-CD) in a cancer pain model. Initially, molecular docking was performed to predict the viability of complex formation. Afterward, PC/β-CD was obtained by slurry complexation, characterized by HPLC and NMR. Finally, PC/β-CD was tested in a Sarcoma 180 (S180)-induced pain model. Molecular docking indicated that the occurrence of interaction between PC and β-CD is favorable. PC/β-CD showed complexation efficiency of 82.61%, and NMR demonstrated PC complexation in the β-CD cavity. In the S180 cancer pain model, PC/β-CD significantly reduced the mechanical hyperalgesia, spontaneous nociception, and nociception induced by non-noxious palpation at the doses tested (p < 0.05) when compared to vehicle differently from free PC (p > 0.05). Therefore, the complexation of PC in β-CD was shown to improve the pharmacological effect of the drug as well as reducing the required dose. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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15 pages, 9154 KiB

Open AccessArticle

Analysis of Essential Oils Components from Aromatic Plants Using Headspace Repellent Method against Aedes aegypti Mosquitoes

by Mohammad Adam Mustapa, Ikhsan Guswenrivo, Ade Zurohtun, Nur Kusaira Khairul Ikram and Muchtaridi Muchtaridi

Molecules 2023, 28(11), 4269; https://doi.org/10.3390/molecules28114269 - 23 May 2023

Cited by 3 | Viewed by 2580

Abstract

This research serves as the basis for developing essential oil-based repellent activity tests against Aedes aegypti mosquitoes. The method used for the isolation of essential oils was the steam distillation method. Virus-free Aedes aegypti mosquitoes were used as test animals by applying the 10% essential oil repellent on the arms of volunteers. The analysis of the essential oils activities and aromas’ components was carried out using headspace repellent and GC-MS methods. Based on the results, the yields of essential oil from 5000 g samples for cinnamon bark, clove flowers, patchouli, nutmeg seed, lemongrass, citronella grass, and turmeric rhizome were 1.9%, 16%, 2.2%, 16.8%, 0.9%, 1.4%, and 6.8%, respectively. The activity test showed that the average repellent power of 10% essential oils, patchouli, cinnamon, nutmeg, turmeric, clove flowers, citronella grass, and lemongrass, was 95.2%, 83.8%, 71.4%, 94.7%, 71.4%, 80.4%, and 85%, respectively. Patchouli and cinnamon had the best average repellent power. Meanwhile, the aroma activities showed that the average repellent power of the patchouli oil was 96%, and the cinnamon oil was 94%. From the GC-MS analysis, nine components were identified in the patchouli essential oil aromas’ with the highest concentration being patchouli alcohol (42.7%), Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1α,7α,8aβ)] (10.8%), α-guaiene (9.22%), and seychellene (8.19%)., whereas using the GC-MS headspace repellent method showed that there were seven components identified in the patchouli essential oil aroma with a high concentration of the components, which were patchouli alcohol (52.5%), Seychellene (5.2%), and α-guaiene (5.2%). The analysis results of cinnamon essential oil using the GC-MS method showed that there were five components identified in the aroma, with E-cinnamaldehyde (73%) being the highest component, whereas using the GC-MS headspace repellent method showed that there were five components identified in the aroma, with highest concentrations of cinnamaldehyde (86.1%). It can be concluded that the chemical compounds contained in patchouli and cinnamon bark have the potential to be environmentally friendly repellents in controlling and preventing Aedes aegypti mosquitoes. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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13 pages, 499 KiB

Open AccessArticle

Chemical Composition and Biological Activities of Essential Oils of Four Asarum Species Growing in Vietnam

by Pham Thi Hong Minh, Nguyen Thuong Tuan, Nguyen Thi Hong Van, Hoang Thi Bich and Do Tien Lam

Molecules 2023, 28(6), 2580; https://doi.org/10.3390/molecules28062580 - 12 Mar 2023

Cited by 2 | Viewed by 2860

Abstract

The essential oils (EOs) of the aerial parts of four Asarum species (A. geophilum, A. yentunensis, A. splendens and A. cordifolium) were isolated by steam distillation and analyzed by the GC/MS method. The A. cordifolium EO contains 33 constituents with the main component being elemicine (77.20%). The A. geophilum EO was contains 49 constituents with the main components being determined as 9-epi-(E)-caryophyllene (18.43%), eudesm-7(11)-en-4-ol (13.41%), β-caryophyllene (8.05%) and phytol (7.23%). The A. yentunensis EO contains 26 constituents with the main components being safrole (64.74%) and sesquicineole (15.34%). The EO of A. splendens contains 41 constituents with the main components being 9-epi-(E)-caryophyllene (15.76%), eudesm-7(11)-en-4-ol (14.21%), β-caryophyllene (9.52%) and trans-bicyclogermacrene (7.50%). For antimicrobial activity, the A. yentunensis EO exhibited the highest inhibition activity against Staphylococcus aureus and the A. cordifolium EO against Bacillus subtillis (MIC values of 100 μg/mL). For antioxidant activity, the A. geophilum EO showed the highest potential with an SC (%) value of 63.34 ± 1.0%, corresponding to an SC₅₀ value of 28.57 µg/mL. For anti-inflammatory activity, the A. splendens EO exhibited the highest potential with an IC₅₀ value of 21.68 µg/mL, corresponding to an inhibition rate of NO production of 69.58 ± 1.3% and the percentage of cell life was 81.85 ± 0.9%. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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8 pages, 2179 KiB

Open AccessCommunication

Alkaloids and Styryl lactones from Goniothalamus ridleyi King and Their α-Glucosidase Inhibitory Activity

by Isaraporn Polbuppha, Passakorn Teerapongpisan, Piyaporn Phukhatmuen, Virayu Suthiphasilp, Tharakorn Maneerat, Rawiwan Charoensup, Raymond J. Andersen and Surat Laphookhieo

Molecules 2023, 28(3), 1158; https://doi.org/10.3390/molecules28031158 - 24 Jan 2023

Cited by 2 | Viewed by 2109

Abstract

Gonioridleylactam (1), a new compound, is a unique dimeric aristolactam isolated from the EtOAc extract of the twigs of Goniothalamus ridleyi King. The structure of gonioridleylactam (1) consists of two different aristolactams linked together with two methylenedioxy bridges at C–3/C–3′ and C–4/C–4′, generating a ten-membered ring of [1,3,6,8]tetraoxecine. A new natural product, gonioridleyindole (3-hydroxymethyl-1-methyl-1H-benz[f]indole-4,9-dione, 2), together with eight known compounds (3–10) were also isolated from this plant. Their structures were extensively characterized by spectroscopic methods and comparisons were made with the literature. Compounds 1–4, 7, and 9 were evaluated for their α-glucosidase inhibitory activity. Of these, 3,5-demethoxypiperolide (7) displayed the highest α-glucosidase inhibitory activity, with an IC₅₀ value of 1.25 µM. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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15 pages, 2684 KiB

Open AccessArticle

UHPLC-Q-Exactive Orbitrap MS/MS-Based Untargeted Metabolomics and Molecular Networking Reveal the Differential Chemical Constituents of the Bulbs and Flowers of Fritillaria thunbergii

by Xin Li, Pan Wang, Yingpeng Tong, Jie Liu and Guowei Shu

Molecules 2022, 27(20), 6944; https://doi.org/10.3390/molecules27206944 - 16 Oct 2022

Cited by 14 | Viewed by 3321

Abstract

Both the bulbs and flowers of Fritillaria thunbergii Miq. (BFT and FFT) are widely applied as expectorants and antitussives in traditional Chinese medicine, but few studies have been conducted to compare the chemical compositions of these plant parts. In this study, 50% methanol extracts of BFT and FFT were analyzed via UHPLC-Q-Exactive Orbitrap MS/MS, and the feasibility of using non-targeted UHPLC-HRMS metabolomics and molecular networking to address the authentication of bulb and flower samples was evaluated. Principal component analysis (PCA), Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA), and heat map analysis showed there were dissimilar metabolites in BFT and FFT. As a result, 252 and 107 peaks in positive ion mode and negative mode, respectively, were considered to represent significant difference variables between BFT and FFT. Then, MS/MS-based molecular networking of BFT and FFT was constructed to perform an in-depth characterization of the peaks using different variables. A total of 31 alkaloids with significant differences were annotated in this paper, including seven cis-D/E-vevanine without C20-OH and one trans-D/E-cevanine with C20-OH, thirteen trans-D/E-cevanine without C20-OH, five cevanine N-oxide, and five veratramine. Among the 31 alkaloids, eight alkaloids had higher FFT than BFT contents, while all the flavonoids identified in our work had greater FFT than BFT contents. The influence of different ingredients on the pharmacological activities of BFT and FFT should be investigated in future studies. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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15 pages, 2502 KiB

Open AccessArticle

An Evaluation of Antimicrobial, Anticancer, Anti-Inflammatory and Antioxidant Activities of Silver Nanoparticles Synthesized from Leaf Extract of Madhuca longifolia Utilizing Quantitative and Qualitative Methods

by Pooja Salve, Aruna Vinchurkar, Rajesh Raut, Ramesh Chondekar, Jaya Lakkakula, Arpita Roy, Md. Jamal Hossain, Saad Alghamdi, Mazen Almehmadi, Osama Abdulaziz, Mamdouh Allahyani, Anas S. Dablool, Md. Moklesur Rahman Sarker and Mohd Fahami Nur Azlina

Molecules 2022, 27(19), 6404; https://doi.org/10.3390/molecules27196404 - 28 Sep 2022

Cited by 32 | Viewed by 4146

Abstract

In the current decade, nanoparticles are synthesized using solvents that are environmentally friendly. A number of nanoparticles have been synthesized at room temperature using water as a solvent, such as gold (Au) and silver (Ag) nanoparticles. As part of nanotechnology, nanoparticles are synthesized through biological processes. Biological methods are the preferred method for the synthesis of inorganic nanoparticles (AgNPs) as a result of their simple and non-hazardous nature. Nanoparticles of silver are used in a variety of applications, including catalysts, spectrally selective coatings for solar absorption, optical objectives, pharmaceutical constituents, and chemical and biological sensing. Antimicrobial agents are among the top uses of silver nanoparticles. In the current study, silver nanoparticles were biologically manufactured through Madhuca longifolia, and their antibacterial activity against pathogenic microorganisms, anticancer, anti-inflammatory, and antioxidant activities were assessed. UV-Vis spectroscopy, XRD (X-ray diffraction), transmission electron microscopy, Zeta Potential, and FTIR were used to characterize silver nanoparticles. The current work describes a cheap and environmentally friendly method to synthesize silver nanoparticles from silver nitrate solution by using plant crude extract as a reducing agent. Full article

(This article belongs to the Special Issue Pharmacological Evaluation and Phytochemical Analysis of Natural Products)

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