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Synthesis, Extraction and Biological Evaluations of Natural Products
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Synthesis, Extraction and Biological Evaluations of Natural Products

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

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 19422

Special Issue Editor

Prof. Dr. George Albert Karikas

E-Mail Website
Guest Editor
Department of Biomedical Sciences, University of West Attica, 12243 Athens, Greece
Interests: pharmacognosy/chemistry of natural products; clinic biochemical and kinetic studies of drugs and biomarkers

Special Issue Information

Dear Colleagues,

Over recent decades, developed countries have had to deal with chronic degenerative diseases and pandemics closely related to the environment, modern lifestyles, and increasing life expectancy. Chronic inflammatory diseases are actually a significant burden on many patients, which may also increase the risk of certain cancers, as persistent inflammation results in DNA damage, which in turn could finally lead to various types of cancer. Considering the decrease in new drugs introduced to the market, along with nature’s high potential for yielding therapeutically relevant bioactive compounds, plant metabolites are emerging as new lead structures for the development of novel drugs for the prevention and cure of diseases. It is already the case that over 75% of anticancer compounds are either natural products or natural product-derived substances, whereas many anti-infective, anti-inflammatory, antioxidant, epigenetic and immunomodulatory agents come from nature. Biotargeted extraction guided by spectroscopy and metabolomic strategies, along with preliminary biological testing, supported by cancer cell lines, etc., followed by synthesis supported by docking analysis to enzymes/receptors would significantly accelerate the exploitation of natural products as sources of novel structures. The above modern approach has become a growing trend, which is expected to continue in the future.

Prof. Dr. George Albert Karikas
Guest Editor

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Keywords

  • degenerative
  • cancer
  • inflammation
  • antioxidants
  • bioactive compounds
  • targeted extraction
  • spectroscopy strategy
  • cell lines
  • docking

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Published Papers (7 papers)

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Research

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26 pages, 6806 KiB  
Article
Xanthophyll-Rich Extract of Phaeodactylum tricornutum Bohlin as New Photoprotective Cosmeceutical Agent: Safety and Efficacy Assessment on In Vitro Reconstructed Human Epidermis Model
by Antonella Smeriglio, Joseph Lionti, Mariarosaria Ingegneri, Bruno Burlando, Laura Cornara, Federica Grillo, Luca Mastracci and Domenico Trombetta
Molecules 2023, 28(10), 4190; https://doi.org/10.3390/molecules28104190 - 19 May 2023
Cited by 1 | Viewed by 2450
Abstract
The nutritional and health properties of algae make them perfect functional ingredients for nutraceutical and cosmeceutical applications. In this study, the Phaeodactylum tricornutum Bohlin (Phaeodactylaceae), a pleiomorphic diatom commonly found in marine ecosystems, was investigated. The in vitro culture conditions used favoured the [...] Read more.
The nutritional and health properties of algae make them perfect functional ingredients for nutraceutical and cosmeceutical applications. In this study, the Phaeodactylum tricornutum Bohlin (Phaeodactylaceae), a pleiomorphic diatom commonly found in marine ecosystems, was investigated. The in vitro culture conditions used favoured the fusiform morphotype, characterized by a high accumulation of neutral lipids, as detected by fluorescence microscopy after BODIPY staining. These data were confirmed by HPLC-DAD-APCI-MS/MS analyses carried out on the ethanolic extract (PTE), which showed a high content of xanthophylls (98.99%), and in particular of fucoxanthin (Fx, 6.67 g/100 g PTE). The antioxidant activity (ORAC, FRAP, TEAC and β-carotene bleaching) and photostability of PTE and Fx against UVA and UVB rays were firstly evaluated by in vitro cell-free assays. After this, phototoxicity and photoprotective studies were carried out on in vitro reconstructed human epidermidis models. Results demonstrated that PTE (0.1% Fx) and 0.1% Fx, both photostable, significantly (p < 0.05) reduce oxidative and inflammatory stress markers (ROS, NO and IL-1α), as well as cytotoxicity and sunburn cells induced by UVA and UVB doses simulating the solar radiation, with an excellent safety profile. However, PTE proved to be more effective than Fx, suggesting its effective and safe use in broad-spectrum sunscreens. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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12 pages, 451 KiB  
Article
Antimicrobial Activities of Saponaria cypria Boiss. Root Extracts, and the Identification of Nine Saponins and Six Phenolic Compounds
by Despina Charalambous, Michalis Christoforou, Elina N. Kitiri, Marios Andreou, Dora Partassides, Christoforos Papachrysostomou, Myriam Frantzi, George A. Karikas and Maria Pantelidou
Molecules 2022, 27(18), 5812; https://doi.org/10.3390/molecules27185812 - 8 Sep 2022
Cited by 4 | Viewed by 2251
Abstract
The purpose of this study was to identify the chemical components in root extracts of Saponaria cypria, an endemic species of Cyprus. Subsequently, the synergistic bioactivity of its root extracts through different extraction procedures was also investigated for the first time. A [...] Read more.
The purpose of this study was to identify the chemical components in root extracts of Saponaria cypria, an endemic species of Cyprus. Subsequently, the synergistic bioactivity of its root extracts through different extraction procedures was also investigated for the first time. A total of nine saponins, along with six phenolic compounds, were identified and quantified using the UHPLC/Q-TOF-MS method. Additionally, S. cypria root extracts demonstrated antibacterial potential against Escherichia coli, Staphylococcus aureus, Enterococcus faecalis and Salmonella enteritidis. S. aureus presented the highest susceptibility among all bacteria tested. These findings provide the first phytochemical data regarding the saponin, phenolic content and antimicrobial activity of S. cypria extracts, indicating that the Cyprus saponaria species is a rich natural source for bioactive compounds with a potentially wider bioactivity spectrum. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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14 pages, 1822 KiB  
Article
Enhancement of TRP Gene Expression and UV Absorption by Bioconverted Chestnut Inner Shell Extracts Using Lactiplantibacillus plantarum
by So-Hee Kim, Suh-Hee Yoem, Jun-Hee Kim, Ji-Woo Hong, Ye-Sol Oh and Jin-Woo Kim
Molecules 2022, 27(15), 4940; https://doi.org/10.3390/molecules27154940 - 3 Aug 2022
Cited by 5 | Viewed by 1975
Abstract
In this work, the suppression of tyrosinase-related genes, including an improvement in UV absorption effects of bioconverted CS extracts (BCS), was investigated to improve the skin-whitening effect. Total polyphenols and total flavonoids, which are bioactive components, increased 2.6- and 5.4-times in bioconversion using [...] Read more.
In this work, the suppression of tyrosinase-related genes, including an improvement in UV absorption effects of bioconverted CS extracts (BCS), was investigated to improve the skin-whitening effect. Total polyphenols and total flavonoids, which are bioactive components, increased 2.6- and 5.4-times in bioconversion using Lactiplantibacillus plantarum SM4, respectively, as compared to ultrasound-assisted extracts (UCS). The effect of BCS on radical scavenging activity, UV-A absorption, and tyrosinase activity inhibition, contributing to skin-whitening, were 1.3-, 1.2-, and 1.2-times higher than those of UCS, respectively. The main component identified in high-performance liquid chromatography (HPLC) was gallic acid in both UCS and BCS, which increased by 2.9-times following bioconversion. The gene expression of tyrosinase-related proteins, including TRP-1 and TRP-2 genes, was studied to confirm the suppression of melanin synthesis by BCS in order to identify the skin-whitening mechanism, and BCS decreased both genes’ expression by 1.7- and 1.6-times, demonstrating that BCS effectively suppressed melanin synthesis. These findings imply that the chestnut inner shell can be employed as a cosmetic material by simultaneously inhibiting melanogenesis and enhancing UV-A absorption through bioconversion using L. plantarum SM4. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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16 pages, 5561 KiB  
Article
Anti-Inflammatory and Wound Healing Properties of Leaf and Rhizome Extracts from the Medicinal Plant Peucedanum ostruthium (L.) W. D. J. Koch
by Cristina Danna, Miriam Bazzicalupo, Mariarosaria Ingegneri, Antonella Smeriglio, Domenico Trombetta, Bruno Burlando and Laura Cornara
Molecules 2022, 27(13), 4271; https://doi.org/10.3390/molecules27134271 - 2 Jul 2022
Cited by 20 | Viewed by 3005
Abstract
Peucedanum ostruthium (L.) W. D. J. Koch (Apiaceae) is a worldwide perennial herb native to the mountains of central Southern Europe. The rhizome has a long tradition in popular medicine, while ethnobotanical surveys have revealed local uses of leaves for superficial injuries. [...] Read more.
Peucedanum ostruthium (L.) W. D. J. Koch (Apiaceae) is a worldwide perennial herb native to the mountains of central Southern Europe. The rhizome has a long tradition in popular medicine, while ethnobotanical surveys have revealed local uses of leaves for superficial injuries. To experimentally validate these uses, plant material was collected in the Gran Paradiso National Park, Aosta Valley, Italy, and the rhizome and leaves were micromorphologically and phytochemically characterized. Polyphenol-enriched hydroalcoholic rhizome and leaf extracts, used in cell-free assays, showed strong and concentration-dependent antioxidant and anti-inflammatory activities. In vitro tests revealed cyclooxygenase and lipoxygenase inhibition by the leaf extract, while the rhizome extract induced only lipoxygenase inhibition. MTT assays on HaCaT keratinocytes and L929 fibroblasts showed low cytotoxicity of extracts. In vitro scratch wound test on HaCaT resulted in a strong induction of wound closure with the leaf extract, while the effect of the rhizome extract was lower. The same test on L929 cells showed similar wound closure induction with both extracts. The results confirmed the traditional medicinal uses of the rhizome as an anti-inflammatory and wound healing remedy for superficial injuries but also highlighted that the leaves can be exploited for these purposes with equal or superior effectiveness. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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15 pages, 520 KiB  
Article
Chemical Characterization, Antioxidant and Antimicrobial Properties of Different Types of Tissue of Cedrus brevifolia Henry Extracts
by Despina Charalambous, Nicolas-George Homer Eliades, Michalis Christoforou, Eleni Kakouri, Charalabos Kanakis, Petros A. Tarantilis and Maria Pantelidou
Molecules 2022, 27(9), 2717; https://doi.org/10.3390/molecules27092717 - 22 Apr 2022
Cited by 8 | Viewed by 1923
Abstract
This study aimed to determine the chemical composition of different types of tissue of Cedrus brevifolia Henry (Pinaceae) methanolic extracts, namely needles, twigs, branches, and bark. Cedrus brevifolia is a narrow endemic coniferous tree species of Cyprus, growing in a sole population in [...] Read more.
This study aimed to determine the chemical composition of different types of tissue of Cedrus brevifolia Henry (Pinaceae) methanolic extracts, namely needles, twigs, branches, and bark. Cedrus brevifolia is a narrow endemic coniferous tree species of Cyprus, growing in a sole population in the mountainous area of Paphos Forest. Chemical analysis of the extracts was performed using liquid chromatography combined with time-of-flight high-resolution mass spectrometry (LC/Q-TOF/HRMS). The majority of the 36 compounds tentatively identified belonged to the flavonoids family. The extract of needles was the richest extract in terms of secondary metabolites. The extracts were studied for their antioxidant activity using the DPPH free radical scavenging assay. Additionally, the antibacterial activity was evaluated by determining both the minimum inhibitory concentration and the minimum bactericidal concentration against Staphylococcus aureus and Escherichia coli. All extracts demonstrated antioxidant property, while bark gave the highest antioxidant capacity (IC50 value of 0.011 mg/mL) compared to the other tissues. Antibacterial activity was observed against both types of bacteria, with the extract of branches presenting the strongest activity against S. aureus (MIC, 0.097 mg/mL and MBC, 0.195 mg/mL). This is the first time that extracts of needles, twigs, branches, and bark of C. brevifolia are compared regarding their chemical composition as well as their antimicrobial and antioxidant properties. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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19 pages, 3610 KiB  
Article
Rosmarinus officinalis L. Leaf Extracts and Their Metabolites Inhibit the Aryl Hydrocarbon Receptor (AhR) Activation In Vitro and in Human Keratinocytes: Potential Impact on Inflammatory Skin Diseases and Skin Cancer
by Panagiotis Kallimanis, Ioanna Chinou, Angeliki Panagiotopoulou, Anatoly A. Soshilov, Guochun He, Michael S. Denison and Prokopios Magiatis
Molecules 2022, 27(8), 2499; https://doi.org/10.3390/molecules27082499 - 13 Apr 2022
Cited by 10 | Viewed by 3453
Abstract
Aryl hydrocarbon receptor (AhR) activation by environmental agents and microbial metabolites is potentially implicated in a series of skin diseases. Hence, it would be very important to identify natural compounds that could inhibit the AhR activation by ligands of microbial origin as 6-formylindolo[3,2-b]carbazole [...] Read more.
Aryl hydrocarbon receptor (AhR) activation by environmental agents and microbial metabolites is potentially implicated in a series of skin diseases. Hence, it would be very important to identify natural compounds that could inhibit the AhR activation by ligands of microbial origin as 6-formylindolo[3,2-b]carbazole (FICZ), indirubin (IND) and pityriazepin (PZ) or the prototype ligand 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). Five different dry Rosmarinus officinalis L. extracts (ROEs) were assayed for their activities as antagonists of AhR ligand binding with guinea pig cytosol in the presence of [3H]TCDD. The methanolic ROE was further assayed towards CYP1A1 mRNA induction using RT-PCR in human keratinocytes against TCDD, FICZ, PZ, and IND. The isolated metabolites, carnosic acid, carnosol, 7-O-methyl-epi-rosmanol, 4′,7-O-dimethylapigenin, and betulinic acid, were assayed for their agonist and antagonist activity in the presence and absence of TCDD using the gel retardation assay (GRA). All assayed ROE extracts showed similar dose-dependent activities with almost complete inhibition of AhR activation by TCDD at 100 ppm. The methanol ROE at 10 ppm showed 99%, 50%, 90%, and 85% inhibition against TCDD, FICZ, IND, and PZ, respectively, in human keratinocytes. Most assayed metabolites exhibited dose-dependent antagonist activity. ROEs inhibit AhR activation by TCDD and by the Malassezia metabolites FICZ, PZ, and IND. Hence, ROE could be useful for the prevention or treatment of skin diseases mediated by activation of AhR. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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Review

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21 pages, 385 KiB  
Review
Hypericum Essential Oils—Composition and Bioactivities: An Update (2012–2022)
by Maria-Eleni Grafakou, Christina Barda, George Albert Karikas and Helen Skaltsa
Molecules 2022, 27(16), 5246; https://doi.org/10.3390/molecules27165246 - 17 Aug 2022
Cited by 10 | Viewed by 2600
Abstract
Hypericum genus, considered to comprise over 500 species that exhibit cosmopolitan distribution, has attracted human interest since ancient times. The present review aims to provide and summarize the recent literature (2012–2022) on the essential oils of the title genus. Research articles were collected [...] Read more.
Hypericum genus, considered to comprise over 500 species that exhibit cosmopolitan distribution, has attracted human interest since ancient times. The present review aims to provide and summarize the recent literature (2012–2022) on the essential oils of the title genus. Research articles were collected from various scientific databases such as PubMed, ScienceDirect, Reaxys, and Google Scholar. Scientific reports related to the chemical composition, as well as the in vitro and in vivo pharmacological activities, are presented, also including a brief outlook of the potential relationship between traditional uses and Hypericum essential oils bioactivity. Full article
(This article belongs to the Special Issue Synthesis, Extraction and Biological Evaluations of Natural Products)
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