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Natural Products: From Isolation and Identification to Biological Activity—Second Edition
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Natural Products: From Isolation and Identification to Biological Activity—Second Edition

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

Deadline for manuscript submissions: closed (31 January 2022) | Viewed by 61370

Special Issue Editor

Dr. Natalizia Miceli

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Guest Editor
Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, 98168 Messina, Italy
Interests: medicinal and aromatic plants; ethnobotanical uses; plant extracts; bioactive compounds; polyphenols; nutraceuticals
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

You are cordially invited to contribute to the second edition of a Special Issue, namely "Natural Products: From Isolation and Identification to Biological Activity—Second Edition".

It is widely accepted in the scientific community that natural products represent a major source of new chemical entities with potential applications for drug discovery (especially as anticancer and anti-infective agents). The discovery of new bioactive natural products as leads for therapeutic development can be inspired by ethnobotanical knowledge or achieved by screening a collection of extracts for bioactivity using in vitro, in cellulo, and even in vivo assays.

Traditionally, plants have been excellent sources of naturally produced compounds with biological effects; other organisms such as marine and terrestrial animals and microorganisms provide very important drug candidate molecules.

The biological activity and structural diversity of the bioactive compounds are unsurpassed by any available synthetic screening libraries. As such, these privileged scaffolds serve as important biologically prevalidated platforms for the design of compound libraries in the search for new drug candidates with diverse indications for human health.

This Special Issue aims at gathering updates and recent advances on natural products as sources of bioactive compounds. This Special Issue may include full articles and reviews focused on new extraction procedures; the isolation and characterization of biologically active compounds from a wide range of natural sources; as well as in vitro and in vivo studies of the biological properties of extracts, fractions, and isolated compounds which could potentially be explored for the development of pharmaceuticals, cosmeceuticals, and nutraceuticals.

Dr. Natalizia Miceli
Guest Editor

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14 pages, 712 KiB  
Article
Phenolic and Volatile Composition and Antioxidant Properties of the Leaf Extract of Brassica fruticulosa subsp. fruticulosa (Brassicaceae) Growing Wild in Sicily (Italy)
by Emilia Cavò, Maria Fernanda Taviano, Federica Davì, Francesco Cacciola, Yassine Oulad El Majdoub, Luigi Mondello, Monica Ragusa, Concetta Condurso, Maria Merlino, Antonella Verzera and Natalizia Miceli
Molecules 2022, 27(9), 2768; https://doi.org/10.3390/molecules27092768 - 26 Apr 2022
Cited by 5 | Viewed by 1820
Abstract
In continuation of research conducted on species of the spontaneous flora of Sicily (Italy) belonging to the Brassicaceae family, Brassica fruticulosa subsp. fruticulosa was selected. It is an edible species utilized in Sicilian traditional medicine. In this study, for the first time, the [...] Read more.
In continuation of research conducted on species of the spontaneous flora of Sicily (Italy) belonging to the Brassicaceae family, Brassica fruticulosa subsp. fruticulosa was selected. It is an edible species utilized in Sicilian traditional medicine. In this study, for the first time, the phenolic and the volatile compounds and the antioxidant properties of the hydroalcoholic extract obtained from the leaves of B. fruticulosa subsp. fruticulosa were characterized. Through HPLC-PDA/ESI-MS analysis, a total of 22 polyphenolic compounds (20 flavonoids and 2 phenolic acids) were identified, with 3-hydroxiferuloylsophoroside-7-O-glucoside (1.30 mg/g ± 0.01) and kaempferol-3-O-feruloylsophoroside-7-O-glucoside (1.28 mg/g ± 0.01) as the most abundant compounds. Through SPME-GC/MS several volatiles belonging to different chemical classes were characterized, with nitriles and aldehydes accounting for more than 54% of the whole volatile fraction. The extract of B. fruticulosa subsp. fruticulosa showed moderate activity in the DPPH assay (IC50 = 1.65 ± 0.08 mg/mL), weak reducing power (17.47 ± 0.65 ASE/mL), and good chelating properties (IC50 = 0.38 ± 0.02 mg/mL), reaching approximately 90% activity at the highest tested concentration. Lastly, the extract was non-toxic against Artemia salina, indicating its potential safety. According to the findings, it can be stated that B. fruticulosa subsp. fruticulosa represents a new valuable source of bioactive compounds. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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17 pages, 2673 KiB  
Article
Inhibition of the Quorum Sensing System, Elastase Production and Biofilm Formation in Pseudomonas aeruginosa by Psammaplin A and Bisaprasin
by Emmanuel T. Oluwabusola, Nursheena Parveen Katermeran, Wee Han Poh, Teo Min Ben Goh, Lik Tong Tan, Oluwatofunmilayo Diyaolu, Jioji Tabudravu, Rainer Ebel, Scott A. Rice and Marcel Jaspars
Molecules 2022, 27(5), 1721; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27051721 - 06 Mar 2022
Cited by 10 | Viewed by 3355
Abstract
Natural products derived from marine sponges have exhibited bioactivity and, in some cases, serve as potent quorum sensing inhibitory agents that prevent biofilm formation and attenuate virulence factor expression by pathogenic microorganisms. In this study, the inhibitory activity of the psammaplin-type compounds, psammaplin [...] Read more.
Natural products derived from marine sponges have exhibited bioactivity and, in some cases, serve as potent quorum sensing inhibitory agents that prevent biofilm formation and attenuate virulence factor expression by pathogenic microorganisms. In this study, the inhibitory activity of the psammaplin-type compounds, psammaplin A (1) and bisaprasin (2), isolated from the marine sponge, Aplysinellarhax, are evaluated in quorum sensing inhibitory assays based on the Pseudomonas aeruginosa PAO1 lasB-gfp(ASV) and rhlA-gfp(ASV) biosensor strains. The results indicate that psammaplin A (1) showed moderate inhibition on lasB-gfp expression, but significantly inhibited the QS-gene promoter, rhlA-gfp, with IC50 values at 14.02 μM and 4.99 μM, respectively. In contrast, bisaprasin (2) displayed significant florescence inhibition in both biosensors, PAO1 lasB-gfp and rhlA-gfp, with IC50 values at 3.53 μM and 2.41 μM, respectively. Preliminary analysis suggested the importance of the bromotyrosine and oxime functionalities for QSI activity in these molecules. In addition, psammaplin A and bisaprasin downregulated elastase expression as determined by the standard enzymatic elastase assay, although greater reduction in elastase production was observed with 1 at 50 μM and 100 μM. Furthermore, the study revealed that bisaprasin (2) reduced biofilm formation in P. aeruginosa. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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15 pages, 1950 KiB  
Article
Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik
by Ayşe Ünlü, Kerem Teralı, Zübeyde Uğurlu Aydın, Ali A. Dönmez, Hasan Soliman Yusufoğlu and İhsan Çalış
Molecules 2022, 27(3), 684; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030684 - 21 Jan 2022
Cited by 5 | Viewed by 2398
Abstract
Polygala species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on Polygala inexpectata [...] Read more.
Polygala species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on Polygala inexpectata, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3′-disinapoyl-sucrose (1), 6-O-sinapoyl,3′-O-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (2), 3′-O-(O-methyl-feruloyl)-sucrose (3), 3′-O-(sinapoyl)-sucrose (4), 3′-O-trimethoxy-cinnamoyl-sucrose (glomeratose) (5), 3′-O-feruloyl-sucrose (sibiricose A5) (6), sinapyl alcohol 4-O-glucoside (syringin or eleutheroside B) (7), liriodendrin (8), and 7,4′-di-O-methylquercetin-3-O-β-rutinoside (ombuin 3-O-rutinoside or ombuoside) (9). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (1H NMR, 13C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some Polygala-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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11 pages, 691 KiB  
Article
The Nutritional and Antioxidant Potential of Artisanal and Industrial Apple Vinegars and Their Ability to Inhibit Key Enzymes Related to Type 2 Diabetes In Vitro
by Driss Ousaaid, Hassan Laaroussi, Hamza Mechchate, Meryem Bakour, Asmae El Ghouizi, Ramzi A. Mothana, Omar Noman, Imane Es-safi, Badiaa Lyoussi and Ilham El Arabi
Molecules 2022, 27(2), 567; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27020567 - 17 Jan 2022
Cited by 8 | Viewed by 3453
Abstract
The main objective of the current study was to determine the physicochemical properties, antioxidant activities, and α-glucosidase and α-amylase inhibition of apple vinegar produced by artisanal and industrial methods. Apple vinegar samples were analyzed to identify their electrical conductivity, pH, titratable acidity, total [...] Read more.
The main objective of the current study was to determine the physicochemical properties, antioxidant activities, and α-glucosidase and α-amylase inhibition of apple vinegar produced by artisanal and industrial methods. Apple vinegar samples were analyzed to identify their electrical conductivity, pH, titratable acidity, total dry matter, Brix, density, mineral elements, polyphenols, flavonoids, and vitamin C. The antioxidant activity of apple vinegar samples was evaluated using two tests, total antioxidant capacity (TAC) and DPPH radical scavenging activity. Finally, we determined α-glucosidase and α-amylase inhibitory activities of artisanal and industrial apple vinegar. The results showed the following values: pH (3.69–3.19); electrical conductivity (2.81–2.79 mS/cm); titratable acidity (3.6–5.4); ash (4.61–2.90); °Brix (6.37–5.2); density (1.02476–1.02012), respectively, for artisanal apple vinegar and industrial apple vinegar. Concerning mineral elements, potassium was the most predominant element followed by sodium, magnesium, and calcium. Concerning bioactive compounds (polyphenols, flavonoids, and vitamin C), the apple vinegar produced by the artisanal method was the richest sample in terms of bioactive compounds and had the highest α-glucosidase and α-amylase inhibition. The findings of this study showed that the quality and biological activities of artisanal apple vinegar were more important than industrial apple vinegar. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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11 pages, 2253 KiB  
Article
Janerin Induces Cell Cycle Arrest at the G2/M Phase and Promotes Apoptosis Involving the MAPK Pathway in THP-1, Leukemic Cell Line
by Mohammad Z. Ahmed, Fahd A. Nasr, Wajhul Qamar, Omar M. Noman, Javed Masood Khan, Abdullah A. Al-Mishari and Ali S. Alqahtani
Molecules 2021, 26(24), 7555; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247555 - 13 Dec 2021
Cited by 7 | Viewed by 2372
Abstract
Janerin is a cytotoxic sesquiterpene lactone that has been isolated and characterized from different species of the Centaurea genus. In this study, janerin was isolated form Centaurothamnus maximus, and its cytotoxic molecular mechanism was studied in THP-1 human leukemic cells. Janerin inhibited [...] Read more.
Janerin is a cytotoxic sesquiterpene lactone that has been isolated and characterized from different species of the Centaurea genus. In this study, janerin was isolated form Centaurothamnus maximus, and its cytotoxic molecular mechanism was studied in THP-1 human leukemic cells. Janerin inhibited the proliferation of THP-1 cells in a dose-dependent manner. Janerin caused the cell cycle arrest at the G2/M phase by decreasing the CDK1/Cyclin-B complex. Subsequently, we found that janerin promoted THP-1 cell death through apoptosis as indicated by flow cytometry. Moreover, apoptosis induction was confirmed by the upregulation of Bax, cleaved PARP-1, and cleaved caspase 3 and the downregulation of an anti-apoptotic Bcl-2 biomarker. In addition, immunoblotting indicated a dose dependent upregulation of P38-MAPK and ERK1/2 phosphorylation during janerin treatment. In conclusion, we have demonstrated for the first time that janerin may be capable of inducing cell cycle arrest and apoptosis through the MAPK pathway, which would be one of the mechanisms underlying its anticancer activity. As a result, janerin has the potential to be used as a therapeutic agent for leukemia. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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12 pages, 1192 KiB  
Communication
New Polyesterified Ursane Derivatives from Leaves of Maesa membranacea and Their Cytotoxic Activity
by Klaudia Michalska, Agnieszka Galanty, Thanh Nguyen Le, Janusz Malarz, Nguyen Quoc Vuong, Van Cuong Pham and Anna Stojakowska
Molecules 2021, 26(22), 7013; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26227013 - 20 Nov 2021
Cited by 4 | Viewed by 1998
Abstract
Maesa membranacea A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic separation of a chloroform-soluble fraction [...] Read more.
Maesa membranacea A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic separation of a chloroform-soluble fraction of extract from leaves of M. membranacea led to the isolation of two new polyesterified ursane triterpenes (1–2) and two known apocarotenoids: (+)-dehydrovomifoliol (3) and (+)-vomifoliol (4). The chemical structures of the undescribed triterpenoids were elucidated using 1D and 2D MNR and HRESIMS spectral data as 2α,6β,22α-triacetoxy-11α-(2-methylbutyryloxy)-urs-12-ene-3α,20β-diol (1) and 2α,6β,22α-triacetoxy-urs-12-ene-3α,11α,20β-triol (2). The newly isolated triterpenoids were tested for their cytotoxic activity in vitro against two melanoma cell lines (HTB140 and A375), normal skin keratinocytes (HaCaT), two colon cancer cell lines (HT29 and Caco-2), two prostate cancer cell lines (DU145 and PC3) and normal prostate epithelial cells (PNT-2). Doxorubicin was used as a reference cytostatic drug. The 2α,6β,22α-triacetoxy-11α-(2-methylbutyryloxy)-urs-12-ene-3α,20β-diol demonstrated cytotoxic activity against prostate cancer cell lines (Du145—IC50 = 35.8 µg/mL, PC3—IC50 = 41.6 µg/mL), and at a concentration of 100 µg/mL reduced viability of normal prostate epithelium (PNT-2) cells by 41%. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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15 pages, 3583 KiB  
Article
Efficacy of Precocene I from Desmosstachya bipinnata as an Effective Bioactive Molecules against the Spodoptera litura Fab. and Its Impact on Eisenia fetida Savigny
by Narayanan Shyam Sundar, Sengodan Karthi, Haridoss Sivanesh, Vethamonickam Stanley-Raja, Kanagaraj Muthu-Pandian Chanthini, Ramakrishnan Ramasubramanian, Govindaraju Ramkumar, Athirstam Ponsankar, Kilapavoor Raman Narayanan, Prabhakaran Vasantha-Srinivasan, Jawaher Alkahtani, Mona S. Alwahibi, Wayne Brian Hunter, Sengottayan Senthil-Nathan, Krutmuang Patcharin, Ahmed Abdel-Megeed, Rady Shawer and Aml Ghaith
Molecules 2021, 26(21), 6384; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216384 - 22 Oct 2021
Cited by 9 | Viewed by 2156
Abstract
The sustainability of agroecosystems are maintained with agro-chemicals. However, after more than 80 years of intensive use, many pests and pathogens have developed resistance to the currently used chemistries. Thus, we explored the isolation and bioactivity of a chemical compound, Precocene I, isolated [...] Read more.
The sustainability of agroecosystems are maintained with agro-chemicals. However, after more than 80 years of intensive use, many pests and pathogens have developed resistance to the currently used chemistries. Thus, we explored the isolation and bioactivity of a chemical compound, Precocene I, isolated from the perennial grass, Desmosstachya bipinnata (L.) Stapf. Fractions produced from chloroform extractions showed suppressive activity on larvae of Spodoptera litura (Lepidoptera: Noctuidae), the Oriental armyworm. Column chromatography analyses identified Precocene I confirmed using FTIR, HPLC and NMR techniques. The bioactivity of the plant-extracted Dp-Precocene I was compared to a commercially produced Precocene I standard. The percentage of mortality observed in insects fed on plant tissue treated with 60 ppm Db-Precocene I was 97, 87 and 81, respectively, for the second, third and fourth instar larvae. The LC50 value of third instars was 23.2 ppm. The percentages of survival, pupation, fecundity and egg hatch were altered at sub-lethal concentrations of Db-Precocene I (2, 4, 6 and 8 ppm, sprays on castor leaves). The observed effects were negatively correlated with concentration, with a decrease in effects as concentrations increased. Distinct changes in feeding activity and damage to gut tissues were observed upon histological examination of S. litura larvae after the ingestion of Db-Precocene I treatments. Comparative analyses of mortality on a non-target organism, the earthworm, Eisenia fetida, at equal concentrations of Precocene I and two chemical pesticides (cypermethrin and monocrotophos) produced mortality only with the chemical pesticide treatments. These results of Db-Precocene I as a highly active bioactive compound support further research to develop production from the grass D. bipinnata as an affordable resource for Precocene-I-based insecticides. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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18 pages, 1704 KiB  
Article
Novel Glycerophospholipid, Lipo- and N-acyl Amino Acids from Bacteroidetes: Isolation, Structure Elucidation and Bioactivity
by Mona-Katharina Bill, Stephan Brinkmann, Markus Oberpaul, Maria A. Patras, Benedikt Leis, Michael Marner, Marc-Philippe Maitre, Peter E. Hammann, Andreas Vilcinskas, Sören M. M. Schuler and Till F. Schäberle
Molecules 2021, 26(17), 5195; https://doi.org/10.3390/molecules26175195 - 27 Aug 2021
Cited by 10 | Viewed by 3733
Abstract
The ‘core’ metabolome of the Bacteroidetes genus Chitinophaga was recently discovered to consist of only seven metabolites. A structural relationship in terms of shared lipid moieties among four of them was postulated. Here, structure elucidation and characterization via ultra-high resolution mass spectrometry (UHR-MS) [...] Read more.
The ‘core’ metabolome of the Bacteroidetes genus Chitinophaga was recently discovered to consist of only seven metabolites. A structural relationship in terms of shared lipid moieties among four of them was postulated. Here, structure elucidation and characterization via ultra-high resolution mass spectrometry (UHR-MS) and nuclear magnetic resonance (NMR) spectroscopy of those four lipids (two lipoamino acids (LAAs), two lysophosphatidylethanolamines (LPEs)), as well as several other undescribed LAAs and N-acyl amino acids (NAAAs), identified during isolation were carried out. The LAAs represent closely related analogs of the literature-known LAAs, such as the glycine-serine dipeptide lipids 430 (2) and 654. Most of the here characterized LAAs (1, 5–11) are members of a so far undescribed glycine-serine-ornithine tripeptide lipid family. Moreover, this study reports three novel NAAAs (N-(5-methyl)hexanoyl tyrosine (14) and N-(7-methyl)octanoyl tyrosine (15) or phenylalanine (16)) from Olivibacter sp. FHG000416, another Bacteroidetes strain initially selected as best in-house producer for isolation of lipid 430. Antimicrobial profiling revealed most isolated LAAs (1–3) and the two LPE ‘core’ metabolites (12, 13) active against the Gram-negative pathogen M. catarrhalis ATCC 25238 and the Gram-positive bacterium M. luteus DSM 20030. For LAA 1, additional growth inhibition activity against B. subtilis DSM 10 was observed. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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12 pages, 1668 KiB  
Article
Saponin Stabilization via Progressive Freeze Concentration and Sterilization Treatment
by Wan Nur Aisyah Wan Osman, Dineshraj Selvarajah and Shafirah Samsuri
Molecules 2021, 26(16), 4856; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164856 - 11 Aug 2021
Cited by 2 | Viewed by 2175
Abstract
Saponin is a biopesticide used to suppress the growth of the golden apple snail population. This study aims to determine the stabilized conditions for saponin storage. The maceration process was used for saponin extraction, and for saponin concentration, progressive freeze concentration (PFC) was [...] Read more.
Saponin is a biopesticide used to suppress the growth of the golden apple snail population. This study aims to determine the stabilized conditions for saponin storage. The maceration process was used for saponin extraction, and for saponin concentration, progressive freeze concentration (PFC) was used. Afterwards, stability analysis was performed by storing the sample for 21 days in two conditions: Room temperature (26 °C) and cold room (10 °C). The samples kept in a cold room were sterilized samples that undergo thermal treatment by placing the sample in the water bath. The non-sterilized samples were kept in room temperature condition for 21 days. The results showed that saponin stored in the cold room (sterilized sample) has low degradation with higher concentration than those stored at room temperature in stability analysis with the highest saponin concentration (0.730 mg/mL) at a concentration temperature of −6 °C and concentration time of 15 min. The lowest saponin concentration obtained by saponin stored at room temperature (non-sterilized sample) is 0.025 mg/mL at a concentration temperature of −6 °C and concentration time of 10 min. Thus, the finding concluded that saponin is sensitive to temperature. Hence, the best storage condition to store saponin after thermal treatment is to keep it in a cold room at 10 °C. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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12 pages, 1714 KiB  
Article
LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents
by Gabin Thierry M. Bitchagno, Jean Garba Koffi, Ingrid Konga Simo, Donald Ulrich K. Kagho, Augustin Silvere Ngouela, Bruno Ndjakou Lenta and Norbert Sewald
Molecules 2021, 26(16), 4810; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164810 - 09 Aug 2021
Cited by 4 | Viewed by 2225
Abstract
A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well [...] Read more.
A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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12 pages, 791 KiB  
Article
Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae)
by Romeo D. Tadjouate Nago, Paul Nayim, Armelle T. Mbaveng, James D. Simo Mpetga, Gabin T. Mbahbou Bitchagno, Badawe Garandi, Pierre Tane, Bruno N. Lenta, Norbert Sewald, Mathieu Tene, Victor Kuete and Augustin Silvere Ngouela
Molecules 2021, 26(16), 4717; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164717 - 04 Aug 2021
Cited by 16 | Viewed by 2178
Abstract
The local botanical Imperata cylindrica in Cameroon was investigated for its antibacterial potency. The methanol extract afforded a total of seven compounds, including five hitherto unreported compounds comprising three flavonoids (1–3) and two C-15 isoprenoid analogues (4 and [...] Read more.
The local botanical Imperata cylindrica in Cameroon was investigated for its antibacterial potency. The methanol extract afforded a total of seven compounds, including five hitherto unreported compounds comprising three flavonoids (1–3) and two C-15 isoprenoid analogues (4 and 5) together with known derivatives (6 and 7). The novelty of the flavonoids was related to the presence of both methyl and prenyl groups. The potential origin of the methyl in the flavonoids is discussed, as well as the chemophenetic significance of our findings. Isolation was performed over repeated silica gel and Sephadex LH-20 column chromatography and the structures were elucidated by (NMR and MS). The crude methanol extract and isolated compounds showed considerable antibacterial potency against a panel of multi-drug resistant (MDR) bacterial strains. The best MIC values were obtained with compound (2) against S. aureus ATCC 25923 (32 µg/mL) and MRSA1 (16 µg/mL). Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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17 pages, 628 KiB  
Article
Determination of Phenolic Compounds in Various Propolis Samples Collected from an African and an Asian Region and Their Impact on Antioxidant and Antibacterial Activities
by Soumaya Touzani, Hamada Imtara, Shankar Katekhaye, Hamza Mechchate, Hayat Ouassou, Ali S. Alqahtani, Omar M. Noman, Fahd A. Nasr, Hugo Fearnley, James Fearnley, Anant Paradkar, Ilham ElArabi and Badiaa Lyoussi
Molecules 2021, 26(15), 4589; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154589 - 29 Jul 2021
Cited by 30 | Viewed by 2641
Abstract
The biological activities of propolis samples are the result of many bioactive compounds present in the propolis. The aim of the present study was to determine the various chemical compounds of some selected propolis samples collected from Palestine and Morocco by the High-Performance [...] Read more.
The biological activities of propolis samples are the result of many bioactive compounds present in the propolis. The aim of the present study was to determine the various chemical compounds of some selected propolis samples collected from Palestine and Morocco by the High-Performance Liquid Chromatography–Photodiode Array Detection (HPLC-PDA) method, as well as the antioxidant and antibacterial activities of this bee product. The chemical analysis of propolis samples by HPLC-PDA shows the cinnamic acid content in the Palestinian sample is higher compared to that in Moroccan propolis. The results of antioxidant activity demonstrated an important free radical scavenging activity (2,2-Diphenyl-1-picrylhydrazyl (DPPH); 2,2′-azino-bis 3-ethylbenzothiazoline-6-sulphonic acid (ABTS) and reducing power assays) with EC50 values ranging between 0.02 ± 0.001 and 0.14 ± 0.01 mg/mL. Additionally, all tested propolis samples possessed a moderate antibacterial activity against bacterial strains. Notably, Minimum Inhibitory Concentrations (MICs) values ranged from 0.31 to 2.50 mg/mL for Gram-negative bacterial strains and from 0.09 to 0.125 mg/mL for Gram-positive bacterial strains. The S2 sample from Morocco and the S4 sample from Palestine had the highest content of polyphenol level. Thus, the strong antioxidant and antibacterial properties were apparently due to the high total phenolic and flavone/flavonol contents in the samples. As a conclusion, the activities of propolis samples collected from both countries are similar, while the cinnamic acid in the Palestinian samples was more than that of the Moroccan samples. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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18 pages, 2639 KiB  
Article
Novel Facet of an Old Dietary Molecule? Direct Influence of Caffeine on Glucose and Biogenic Amine Handling by Human Adipocytes
by Wiem Haj Ahmed, Nathalie Boulet, Anaïs Briot, Barry J. Ryan, Gemma K. Kinsella, Jeffrey O’Sullivan, Francisco Les, Josep Mercader-Barceló, Gary T. M. Henehan and Christian Carpéné
Molecules 2021, 26(13), 3831; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133831 - 23 Jun 2021
Cited by 7 | Viewed by 2423
Abstract
Caffeine is a plant alkaloid present in food and beverages consumed worldwide. It has high lipid solubility with recognized actions in the central nervous system and in peripheral tissues, notably the adipose depots. However, the literature is scant regarding caffeine’s influence on adipocyte [...] Read more.
Caffeine is a plant alkaloid present in food and beverages consumed worldwide. It has high lipid solubility with recognized actions in the central nervous system and in peripheral tissues, notably the adipose depots. However, the literature is scant regarding caffeine’s influence on adipocyte functions other than lipolysis, such as glucose incorporation into lipids (lipogenesis) and amine oxidation. The objective of this study was to explore the direct effects of caffeine and of isobutylmethylxanthine (IBMX) on these adipocyte functions. Glucose transport into fat cells freshly isolated from mice, rats, or humans was monitored by determining [3H]-2-deoxyglucose (2-DG) uptake, while the incorporation of radiolabeled glucose into cell lipids was used as an index of lipogenic activity. Oxidation of benzylamine by primary amine oxidase (PrAO) was inhibited by increasing doses of caffeine in human adipose tissue preparations with an inhibition constant (Ki) in the millimolar range. Caffeine inhibited basal and insulin-stimulated glucose transport as well as lipogenesis in rodent adipose cells. The antilipogenic action of caffeine was also observed in adipocytes from mice genetically invalidated for PrAO activity, indicating that PrAO activity was not required for lipogenesis inhibition. These caffeine inhibitory properties were extended to human adipocytes: relative to basal 2-DG uptake, set at 1.0 ± 0.2 for 6 individuals, 0.1 mM caffeine tended to reduce uptake to 0.83 ± 0.08. Insulin increased uptake by 3.86 ± 1.11 fold when tested alone at 100 nM, and by 3.21 ± 0.80 when combined with caffeine. Our results reinforce the recommendation of caffeine’s potential in the treatment or prevention of obesity complications. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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15 pages, 1926 KiB  
Article
Bertholletia excelsa Seeds Reduce Anxiety-Like Behavior, Lipids, and Overweight in Mice
by Oswaldo Frausto-González, Claudia J. Bautista, Fernando Narváez-González, Alberto Hernandez-Leon, Erika Estrada-Camarena, Fausto Rivero-Cruz and María Eva González-Trujano
Molecules 2021, 26(11), 3212; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113212 - 27 May 2021
Cited by 2 | Viewed by 2527
Abstract
Overweight, obesity, and psychiatric disorders are serious health problems. To evidence the anxiolytic-like effects and lipid reduction in mice receiving a high-calorie diet and Bertholletia excelsa seeds in a nonpolar extract (SBHX, 30 and 300 mg/kg), animals were assessed in open-field, hole-board, and [...] Read more.
Overweight, obesity, and psychiatric disorders are serious health problems. To evidence the anxiolytic-like effects and lipid reduction in mice receiving a high-calorie diet and Bertholletia excelsa seeds in a nonpolar extract (SBHX, 30 and 300 mg/kg), animals were assessed in open-field, hole-board, and elevated plus-maze tests. SBHX (3 and 10 mg/kg) potentiated the pentobarbital-induced hypnosis. Chronic administration of SBHX for 40 days was given to mice fed with a hypercaloric diet to determine the relationship between water and food intake vs. changes in body weight. Testes, epididymal white adipose tissue (eWAT), and liver were dissected to analyze fat content, triglycerides, cholesterol, and histological effects after administering the hypercaloric diet and SBHX. Fatty acids, such as palmitoleic acid (0.14%), palmitic acid (21.42%), linoleic acid (11.02%), oleic acid (59.97%), and stearic acid (7.44%), were identified as constituents of SBHX, producing significant anxiolytic-like effects and preventing body-weight gain in mice receiving the hypercaloric diet without altering their water or food consumption. There was also a lipid-lowering effect on the testicular tissue and eWAT and a reduction of adipocyte area in eWAT. Our data evidence beneficial properties of B. excelsa seeds influencing global health concerns such as obesity and anxiety. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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9 pages, 1800 KiB  
Article
Densazalin, a New Cytotoxic Diazatricyclic Alkaloid from the Marine Sponge Haliclona densaspicula
by Buyng Su Hwang, Yong Tae Jeong, Sangbum Lee, Eun Ju Jeong and Jung-Rae Rho
Molecules 2021, 26(11), 3164; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113164 - 25 May 2021
Cited by 4 | Viewed by 1759
Abstract
Densazalin, a polycyclic alkaloid, was isolated from the marine sponge Haliclona densaspicula collected in Korea. The complete structure of the compound was determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance techniques, high-resolution mass spectrometry, and comparison of the calculated and [...] Read more.
Densazalin, a polycyclic alkaloid, was isolated from the marine sponge Haliclona densaspicula collected in Korea. The complete structure of the compound was determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance techniques, high-resolution mass spectrometry, and comparison of the calculated and measured electronic circular dichroism spectra. Densazalin possesses a unique 5,11-diazatricyclo[7.3.1.02,7]tridecan-2,4,6-triene moiety, which is connected by two linear carbon chains. This compound was derived from the biogenetic precursor bis-1,3-dialkylpyridnium. Densazalin exhibited cytotoxic activity on two human tumor cell lines (AGS and HepG2) in the Cell Counting Kit-8 (CCK-8) bioassay, with IC50 values ranging from 15.5 to 18.4 μM. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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15 pages, 2430 KiB  
Article
Evaluation of the Antinociceptive, Antiallodynic, Antihyperalgesic and Anti-Inflammatory Effect of Polyalthic Acid
by Juan Rodríguez-Silverio, María Elena Sánchez-Mendoza, Héctor Isaac Rocha-González, Juan Gerardo Reyes-García, Francisco Javier Flores-Murrieta, Yaraset López-Lorenzo, Geovanna Nallely Quiñonez-Bastidas and Jesús Arrieta
Molecules 2021, 26(10), 2921; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26102921 - 14 May 2021
Cited by 5 | Viewed by 1777
Abstract
Nonsteroidal anti-inflammatory drugs (NSAIDs) are very commonly used, but their adverse effects warrant investigating new therapeutic alternatives. Polyalthic acid, a labdane-type diterpenoid, is known to produce gastroprotection, tracheal smooth muscle relaxation, and antitumoral, antiparasitic and antibacterial activity. This study aimed to evaluate the [...] Read more.
Nonsteroidal anti-inflammatory drugs (NSAIDs) are very commonly used, but their adverse effects warrant investigating new therapeutic alternatives. Polyalthic acid, a labdane-type diterpenoid, is known to produce gastroprotection, tracheal smooth muscle relaxation, and antitumoral, antiparasitic and antibacterial activity. This study aimed to evaluate the antinociceptive, antiallodynic, antihyperalgesic and anti-inflammatory effect of polyalthic acid on rats. Moreover, the effectiveness of treating hyperalgesia with a combination of polyalthic acid and naproxen was analyzed, as well as the type of drug–drug interaction involved. Nociception was examined by injecting 1% formalin into the right hind paw and thermal hyperalgesia and inflammation by injecting a 1% carrageenan solution into the left hind paw of rats. Allodynia was assessed on an L5/L6 spinal nerve ligation model. Polyalthic acid generated significant antinociceptive (56–320 mg/kg), antiallodynic (100–562 mg/kg), and antihyperalgesic and anti-inflammatory (10–178 mg/kg) effects. Antinociception mechanisms were explored by pretreating the rats with naltrexone, ODQ and methiothepin, finding the effect blocked by the former two compounds, which indicates the participation of opioid receptors and guanylate cyclase. An isobolographic analysis suggests synergism between polyalthic acid and naproxen in the combined treatment of hyperalgesia. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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Review

Jump to: Research

16 pages, 754 KiB  
Review
Fruits Vinegar: Quality Characteristics, Phytochemistry, and Functionality
by Driss Ousaaid, Hamza Mechchate, Hassan Laaroussi, Christophe Hano, Meryem Bakour, Asmae El Ghouizi, Raffaele Conte, Badiaa Lyoussi and Ilham El Arabi
Molecules 2022, 27(1), 222; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010222 - 30 Dec 2021
Cited by 34 | Viewed by 7144
Abstract
The popularity of fruits vinegar (FsV) has been increased recently as a healthy drink wealthy in bioactive compounds that provide several beneficial properties. This review was designed in the frame of valorization of fruits vinegar as a by-product with high value added by [...] Read more.
The popularity of fruits vinegar (FsV) has been increased recently as a healthy drink wealthy in bioactive compounds that provide several beneficial properties. This review was designed in the frame of valorization of fruits vinegar as a by-product with high value added by providing overall information on its biochemical constituents and beneficial potencies. It contains a cocktail of bioactive ingredients including polyphenolic acids, organic acids, tetramethylperazine, and melanoidins. Acetic acid is the most abundant organic acid and chlorogenic acid is the major phenol in apple vinegar. The administration of fruits vinegar could prevent diabetes, hypercholesterolemia, oxidative stress, cancer, and boost immunity as well as provide a remarkable antioxidant ability. The production techniques influence the quality of vinegar, and consequently, its health benefits. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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27 pages, 11027 KiB  
Review
Lamiaceae in Mexican Species, a Great but Scarcely Explored Source of Secondary Metabolites with Potential Pharmacological Effects in Pain Relief
by Alberto Hernandez-Leon, Gabriel Fernando Moreno-Pérez, Martha Martínez-Gordillo, Eva Aguirre-Hernández, María Guadalupe Valle-Dorado, María Irene Díaz-Reval, María Eva González-Trujano and Francisco Pellicer
Molecules 2021, 26(24), 7632; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247632 - 16 Dec 2021
Cited by 8 | Viewed by 3791
Abstract
The search for molecules that contribute to the relief of pain is a field of research in constant development. Lamiaceae is one of the most recognized families world-wide for its use in traditional medicine to treat diseases that include pain and inflammation. Mexico [...] Read more.
The search for molecules that contribute to the relief of pain is a field of research in constant development. Lamiaceae is one of the most recognized families world-wide for its use in traditional medicine to treat diseases that include pain and inflammation. Mexico can be considered one of the most important centers of diversification, and due to the high endemism of this family, it is crucial for the in situ conservation of this family. Information about the most common genera and species found in this country and their uses in folk medicine are scarcely reported in the literature. After an extensive inspection in bibliographic databases, mainly Sciencedirect, Pubmed and Springer, almost 1200 articles describing aspects of Lamiaceae were found; however, 217 articles were selected because they recognize the Mexican genera and species with antinociceptive and/or anti-inflammatory potential to relieve pain, such as Salvia and Agastache. The bioactive constituents of these genera were mainly terpenes (volatile and non-volatile) and phenolic compounds such as flavonoids (glycosides and aglycone). The aim of this review is to analyze important aspects of Mexican genera of Lamiaceae, scarcely explored as a potential source of secondary metabolites responsible for the analgesic and anti-inflammatory properties of these species. In addition, we point out the possible mechanisms of action involved and the modulatory pathways investigated in different experimental models. As a result of this review, it is important to mention that scarce information has been reported regarding species of this family from Mexican genera. In fact, despite Calosphace being one of the largest subgenera of Salvia in the world, found mainly in Mexico, it has been barely investigated regarding its potential biological activities and recognized bioactive constituents. The scientific evidence regarding the different bioactive constituents found in species of Lamiaceae demonstrates that several species require further investigation in preclinical studies, and of course also in controlled clinical trials evaluating the efficacy and safety of these natural products to support their therapeutic potential in pain relief and/or inflammation, among other health conditions. Since Mexico is one of the most important centers of diversification, and due to the high endemism of species of this family, it is crucial their rescue, in situ conservation, and investigation of their health benefits. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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16 pages, 1105 KiB  
Review
Andrographolide: A Herbal-Chemosynthetic Approach for Enhancing Immunity, Combating Viral Infections, and Its Implication on Human Health
by Archana Mishra, Haq Abdul Shaik, Rakesh Kumar Sinha and Bakht Ramin Shah
Molecules 2021, 26(22), 7036; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26227036 - 21 Nov 2021
Cited by 13 | Viewed by 4637
Abstract
Plants consistently synthesize and accumulate medically valuable secondary metabolites which can be isolated and clinically tested under in vitro conditions. An advancement with such important phytochemical production has been recognized and utilized as herbal drugs. Bioactive andrographolide (AGL; C20H30O [...] Read more.
Plants consistently synthesize and accumulate medically valuable secondary metabolites which can be isolated and clinically tested under in vitro conditions. An advancement with such important phytochemical production has been recognized and utilized as herbal drugs. Bioactive andrographolide (AGL; C20H30O5) isolated from Andrographis paniculate (AP) (Kalmegh) is a diterpenoid lactones having multifunctional medicinal properties including anti-manic, anti-inflammatory, liver, and lung protective. AGL is known for its immunostimulant activity against a variety of microbial infections thereby, regulating classical and alternative macrophage activation, Ag-specific antibody production during immune disorder therapy. In vitro studies with AGL found it to be effective against multiple tumors, neuronal disorders, diabetes, pneumonia, fibrosis, and other diverse therapeutic misadventures. Generally, virus-based diseases like ZIKA, influenza A virus subtype (H1NI), Ebola (EBOV), Dengue (DENV), and coronavirus (COVID-19) epidemics have greatly increased scientific interest and demands to develop more effective and economical immunomodulating drugs with minimal side effects. Trials and in vitro pharmacological studies with AGL and medicinally beneficial herbs might contribute to benefit the human population without using chemical-based synthetic drugs. In this review, we have discussed the possible role of AGL as a promising herbal-chemo remedy during human diseases, viral infections and as an immunity booster. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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45 pages, 1426 KiB  
Review
Stevia Genus: Phytochemistry and Biological Activities Update
by Jimena Borgo, Laura C. Laurella, Florencia Martini, Cesar A. N. Catalán and Valeria P. Sülsen
Molecules 2021, 26(9), 2733; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092733 - 06 May 2021
Cited by 18 | Viewed by 5083
Abstract
The Stevia genus (Asteraceae) comprises around 230 species, distributed from the southern United States to the South American Andean region. Stevia rebaudiana, a Paraguayan herb that produces an intensely sweet diterpene glycoside called stevioside, is the most relevant member of this genus. [...] Read more.
The Stevia genus (Asteraceae) comprises around 230 species, distributed from the southern United States to the South American Andean region. Stevia rebaudiana, a Paraguayan herb that produces an intensely sweet diterpene glycoside called stevioside, is the most relevant member of this genus. Apart from S. rebaudiana, many other species belonging to the Stevia genus are considered medicinal and have been popularly used to treat different ailments. The members from this genus produce sesquiterpene lactones, diterpenes, longipinanes, and flavonoids as the main types of phytochemicals. Many pharmacological activities have been described for Stevia extracts and isolated compounds, antioxidant, antiparasitic, antiviral, anti-inflammatory, and antiproliferative activities being the most frequently mentioned. This review aims to present an update of the Stevia genus covering ethnobotanical aspects and traditional uses, phytochemistry, and biological activities of the extracts and isolated compounds. Full article
(This article belongs to the Special Issue Natural Products: From Isolation and Identification to Biological Activity—Second Edition)
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