scholarly journals Synthesis of a Novel α-Glucosyl Ginsenoside F1 by Cyclodextrin Glucanotransferase and Its In Vitro Cosmetic Applications

Biomolecules ◽  
2018 ◽  
Vol 8 (4) ◽  
pp. 142 ◽  
Author(s):  
Seong Moon ◽  
Hye Lee ◽  
Ramya Mathiyalagan ◽  
Yu Kim ◽  
Dong Yang ◽  
...  
Keyword(s):  
Quantum Coherence ◽  
Dermal Fibroblast ◽  
Multiple Bond ◽  
Proton Nuclear Magnetic Resonance ◽  
Cyclodextrin Glucanotransferase ◽  
The Novel ◽  
Pharmacological Activities ◽  
Matrix Metalloproteinase 1 ◽  
Derivatives Of

Ginsenosides from Panax ginseng (Korean ginseng) are unique triterpenoidal saponins that are considered to be responsible for most of the pharmacological activities of P. ginseng. However, the various linkage positions cause different pharmacological activities. In this context, we aimed to synthesize new derivatives of ginsenosides with unusual linkages that show enhanced pharmacological activities. Novel α-glycosylated derivatives of ginsenoside F1 were synthesized from transglycosylation reactions of dextrin (sugar donor) and ginsenoside F1 (acceptor) by the successive actions of Toruzyme®3.0L, a cyclodextrin glucanotransferase. One of the resultant products was isolated and identified as (20S)-3β,6α,12β-trihydroxydammar-24ene-(20-O-β-D-glucopyranosyl-(1→2)-α-D-glucopyranoside) by various spectroscopic characterization techniques of fast atom bombardment-mass spectrometry (FAB-MS), infrared spectroscopy (IR), proton-nuclear magnetic resonance (1H-NMR), 13C-NMR, gradient heteronuclear single quantum coherence (gHSQC), and gradient heteronuclear multiple bond coherence (gHMBC). As expected, the novel α-glycosylated ginsenoside F1 (G1-F1) exhibited increased solubility, lower cytotoxicity toward human dermal fibroblast cells (HDF), and higher tyrosinase activity and ultraviolet A (UVA)-induced inhibitory activity against matrix metalloproteinase-1 (MMP-1) than ginsenoside F1. Since F1 has been reported as an antiaging and antioxidant agent, the enhanced efficacies of the novel α-glycosylated ginsenoside F1 suggest that it might be useful in cosmetic applications after screening.

scholarly journals N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl] quinoline]-acetamide

Molbank ◽  
10.3390/m1213 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1213
Author(s):  
Paolo Coghi ◽  
Jerome P. L. Ng ◽  
Ali Adnan Nasim ◽  
Vincent Kam Wai Wong
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Quantum Coherence ◽  
Biologically Active ◽  
Proton Nuclear Magnetic Resonance ◽  
Dipolar Cycloaddition ◽  
Heteronuclear Single Quantum Coherence ◽  
Pharmacokinetic Properties ◽  
Nuclear Magnetic

The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties.

scholarly journals Pharmacological Advances of Chloroquine and Hydroxychloroquine: From Antimalarials to Investigative Therapies in COVID-19

2020 ◽  
Vol 15 (9) ◽  
pp. 1934578X2095364
Author(s):  
Yang Song ◽  
Elise Fields
Keyword(s):  
Severe Acute Respiratory Syndrome ◽  
Adverse Effects ◽  
Viral Infection ◽  
Therapeutic Potential ◽  
Pharmacological Activities ◽  
Pharmaceutical Applications ◽  
Natural Alkaloid ◽  
Derivatives Of ◽  
Existing Chemicals

During the coronavirus disease 2019 (COVID-19) pandemic, numerous existing chemicals have been screened for antiviral potential against the emerging coronavirus severe acute respiratory syndrome coronavirus 2. Chloroquine and hydroxychloroquine, after exhibiting potent in vitro efficacy, have gained tremendous attention. Both therapeutics are derivatives of natural alkaloid quinine and were first synthesized to treat malaria. Thereafter, the pharmaceutical applications of the agents have expanded to many new areas. In this article, the medicinal history and pharmacological activities of chloroquine and hydroxychloroquine are summarized. Antimalarial, anti-inflammatory, antitumor, antiviral properties, and therapeutic potential in the emerging viral infection COVID-19 are discussed. Pharmacokinetics, adverse effects, and toxicities are reviewed.

scholarly journals Antioxidant Activity and Anti-Photoaging Effects on UVA-Irradiated Human Fibroblasts of Rosmarinic Acid Enriched Extract Prepared from Thunbergia laurifolia Leaves

Plants ◽  
2021 ◽  
Vol 10 (8) ◽  
pp. 1648
Author(s):  
Thanawat Pattananandecha ◽  
Sutasinee Apichai ◽  
Jakaphun Julsrigival ◽  
Malyn Ungsurungsie ◽  
Suched Samuhasaneetoo ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Antioxidant Activity ◽  
Rosmarinic Acid ◽  
Dermal Fibroblast ◽  
Human Fibroblasts ◽  
Potential Candidate ◽  
Normal Human Dermal Fibroblast ◽  
Matrix Metalloproteinase 1 ◽  
Thunbergia Laurifolia

The current study investigated the inhibiting effect on reactive oxygen species (ROS), reactive nitrogen species (RNS), and matrix metalloproteinase-1 (MMP-1) production in a cell-based study of standardized rosmarinic acid enriched extract (SRAEE) prepared from Thunbergia laurifolia leaves. HPLC chromatogram revealed that rosmarinic acid is a major component in prepared SRAEE, followed by caffeic acid. SRAEE exhibited antioxidant activity both in vitro and cell-based studies. SRAEE showed scavenging effects on nitric oxide and superoxide anion and inhibition effects on lipid peroxidation in vitro. SRAEE also inhibited ROS and MMP-1 production in normal human dermal fibroblast cells induced by H2O2 and UVA, respectively, without exerted cytotoxicity. Additionally, collagen degradation was protected by SRAEE induced by UVA. Nitric oxide and inducible nitric oxide synthase (iNOS) productions were also inhibited by SRAEE in RAW264.7 mouse macrophage cells induced by combined lipopolysaccharide (LPS)-interferon-γ (IFN-γ). The results indicated that SRAEE is a potential candidate as a natural pharmaceutical active ingredient for cosmeceutical product application.

scholarly journals Novel Endochin-Like Quinolones Exhibit Potent In Vitro Activity against Plasmodium knowlesi but Do Not Synergize with Proguanil

2020 ◽  
Vol 64 (5) ◽  
Author(s):  
Donelly A. van Schalkwyk ◽  
Michael K. Riscoe ◽  
Sovitj Pou ◽  
Rolf W. Winter ◽  
Aaron Nilsen ◽  
...  
Keyword(s):  
Plasmodium Knowlesi ◽  
Ex Vivo ◽  
Life Cycles ◽  
The Novel ◽  
Important Species ◽  
Content Type ◽  
Ongoing Development ◽  
Multiple Species ◽  
Derivatives Of

ABSTRACT Quinolones, such as the antimalarial atovaquone, are inhibitors of the malarial mitochondrial cytochrome bc1 complex, a target critical to the survival of both liver- and blood-stage parasites, making these drugs useful as both prophylaxis and treatment. Recently, several derivatives of endochin have been optimized to produce novel quinolones that are active in vitro and in animal models. While these quinolones exhibit potent ex vivo activity against Plasmodium falciparum and Plasmodium vivax, their activity against the zoonotic agent Plasmodium knowlesi is unknown. We screened several of these novel endochin-like quinolones (ELQs) for their activity against P. knowlesi in vitro and compared this with their activity against P. falciparum tested under identical conditions. We demonstrated that ELQs are potent against P. knowlesi (50% effective concentration, <117 nM) and equally effective against P. falciparum. We then screened selected quinolones and partner drugs using a longer exposure (2.5 life cycles) and found that proguanil is 10-fold less potent against P. knowlesi than P. falciparum, while the quinolones demonstrate similar potency. Finally, we used isobologram analysis to compare combinations of the ELQs with either proguanil or atovaquone. We show that all quinolone combinations with proguanil are synergistic against P. falciparum. However, against P. knowlesi, no evidence of synergy between proguanil and the quinolones was found. Importantly, the combination of the novel quinolone ELQ-300 with atovaquone was synergistic against both species. Our data identify potentially important species differences in proguanil susceptibility and in the interaction of proguanil with quinolones and support the ongoing development of novel quinolones as potent antimalarials that target multiple species.

Synthesis, structure and in vitro cytostatic activity study of the novel organotin(IV) derivatives of p -aminobenzenesulfonic acid

2018 ◽  
Vol 861 ◽  
pp. 151-158 ◽  
Author(s):  
Ge-Hua Wen ◽  
Ru-Fen Zhang ◽  
Qian-Li Li ◽  
Shao-Liang Zhang ◽  
Jing Ru ◽  
...  
Keyword(s):  
Cytostatic Activity ◽  
The Novel ◽  
Derivatives Of

scholarly journals A Novel Frameshifting Inhibitor Having Antiviral Activity against Zoonotic Coronaviruses

Viruses ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1639
Author(s):  
Dae-Gyun Ahn ◽  
Gun Young Yoon ◽  
Sunhee Lee ◽  
Keun Bon Ku ◽  
Chonsaeng Kim ◽  
...  
Keyword(s):  
Inhibitory Effect ◽  
Drug Candidate ◽  
Replicase Gene ◽  
The Novel ◽  
Viral Propagation ◽  
Infected Cells ◽  
Repurposed Drugs ◽  
Rna Pseudoknot ◽  
Derivatives Of

Recent outbreaks of zoonotic coronaviruses, such as Middle East respiratory syndrome coronavirus (MERS-CoV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), have caused tremendous casualties and great economic shock. Although some repurposed drugs have shown potential therapeutic efficacy in clinical trials, specific therapeutic agents targeting coronaviruses have not yet been developed. During coronavirus replication, a replicase gene cluster, including RNA-dependent RNA polymerase (RdRp), is alternatively translated via a process called -1 programmed ribosomal frameshift (−1 PRF) by an RNA pseudoknot structure encoded in viral RNAs. The coronavirus frameshifting has been identified previously as a target for antiviral therapy. In this study, the frameshifting efficiencies of MERS-CoV, SARS-CoV and SARS-CoV-2 were determined using an in vitro −1 PRF assay system. Our group has searched approximately 9689 small molecules to identify potential −1 PRF inhibitors. Herein, we found that a novel compound, 2-(5-acetylthiophen-2yl)furo[2,3-b]quinoline (KCB261770), inhibits the frameshifting of MERS-CoV and effectively suppresses viral propagation in MERS-CoV-infected cells. The inhibitory effects of 87 derivatives of furo[2,3-b]quinolines were also examined showing less prominent inhibitory effect when compared to compound KCB261770. We demonstrated that KCB261770 inhibits the frameshifting without suppressing cap-dependent translation. Furthermore, this compound was able to inhibit the frameshifting, to some extent, of SARS-CoV and SARS-CoV-2. Therefore, the novel compound 2-(5-acetylthiophen-2yl)furo[2,3-b]quinoline may serve as a promising drug candidate to interfere with pan-coronavirus frameshifting.

scholarly journals Anticancer Potential of Betulonic Acid Derivatives

2021 ◽  
Vol 22 (7) ◽  
pp. 3676
Author(s):  
Adelina Lombrea ◽  
Alexandra Denisa Scurtu ◽  
Stefana Avram ◽  
Ioana Zinuca Pavel ◽  
Māris Turks ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Betulonic Acid ◽  
Pharmacological Activities ◽  
Cellular Resistance ◽  
Drug Candidates ◽  
Starting Point ◽  
Derivatives Of ◽  
Biological And Pharmacological Activities

Clinical trials have evidenced that several natural compounds, belonging to the phytochemical classes of alkaloids, terpenes, phenols and flavonoids, are effective for the management of various types of cancer. Latest research has proven that natural products and their semisynthetic variants may serve as a starting point for new drug candidates with a diversity of biological and pharmacological activities, designed to improve bioavailability, overcome cellular resistance, and enhance therapeutic efficacy. This review was designed to bring an update regarding the anticancer potential of betulonic acid and its semisynthetic derivatives. Chemical derivative structures of betulonic acid including amide, thiol, and piperidine groups, exert an amplification of the in vitro anticancer potential of betulonic acid. With the need for more mechanistic and in vivo data, some derivatives of betulonic acids may represent promising anticancer agents.

IL-22 capacitates dermal fibroblast responses to TNF in scleroderma

2015 ◽  
Vol 75 (9) ◽  
pp. 1697-1705 ◽  
Author(s):  
Nicolò Costantino Brembilla ◽  
Aleksandra Maria Dufour ◽  
Montserrat Alvarez ◽  
Stéphanie Hugues ◽  
Elisa Montanari ◽  
...  
Keyword(s):  
Conditioned Medium ◽  
Transforming Growth Factor ◽  
Dermal Fibroblast ◽  
Dermal Fibroblasts ◽  
Th22 Cells ◽  
Matrix Metalloproteinase 1 ◽  
Dermal Thickness ◽  
Extracellular Matrix Components

ObjectivesInterleukin (IL) 22 mRNA in systemic sclerosis (SSc) skin and Th22 cells in SSc peripheral blood are increased, but the role of IL-22 in fibrosis development remains poorly understood.MethodsBiopsies were obtained from the involved skin of 15 SSc, 4 morphea and 8 healthy donors (HD). The presence of IL-22+ cells in the skin was determined by immunostaining. The in vitro response of HD and SSc fibroblasts to IL-22, IL-22 in conjunction with tumour necrosis factor (TNF) or keratinocyte conditioned medium was assessed by ELISA, radioimmunoassay (RIA), real-time PCR and western blot. The in vivo response in mice was assessed by histomorphometry.ResultsIL-22+ cells were over-represented in the dermis and epidermis of morphea and in the epidermis of SSc compared with HD. The majority of dermal IL-22+ cells were T cells. Dermal fibroblasts expressed both IL-22 receptor subunits IL-10RB and IL-22RA, expression of which was enhanced by TNF and reduced by transforming growth factor (TGF)-β. IL-22 induced rapid phosphorylation of p38 and ERK1/2 in fibroblasts, but failed to induce the synthesis of chemokines and extracellular matrix components. However, IL-22 enhanced the production of monocyte chemotactic protein 1, IL-8 and matrix metalloproteinase 1 induced by TNF. Fibroblast responses were maximal in the presence of conditioned medium from keratinocytes activated by IL-22 in conjunction with TNF. Dermal thickness was maximal in mice injected simultaneously with IL-22 and TNF.ConclusionsIL-22 capacitates fibroblast responses to TNF and promotes a proinflammatory fibroblast phenotype by favouring TNF-induced keratinocyte activation. These results define a novel role for keratinocyte–fibroblast interactions in the context of skin fibrosis.

scholarly journals Preparation and Characterization of Protocatechuic Acid Sulfates

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 307 ◽  
Author(s):  
Sofia Gutierrez-Zetina ◽  
Susana Gonzalez-Manzano ◽  
Jose Perez-Alonso ◽  
Ana Gonzalez-Paramas ◽  
Celestino Santos-Buelga
Keyword(s):  
Quantum Coherence ◽  
Protocatechuic Acid ◽  
Biological Fluids ◽  
Biological Effects ◽  
Multiple Bond ◽  
Human Organism ◽  
Dietary Polyphenols ◽  
13C Nuclear Magnetic Resonance

Protocatechuic acid (3,4-dihydroxybenzoic acid; PCA) is a phenolic acid present in plants as a secondary metabolite and is also produced in the human organism as a metabolite from the degradation of polyphenols by the intestinal microbiota, particularly of flavonoids. However, PCA, like most polyphenols, is biotransformed in the human body to different conjugates as sulfates, which are found circulating in blood and could be involved in the bioactivity of the original compound. This paper describes a simple process for the preparation of PCA monosulfates with satisfactory yields. Two compounds were obtained that were identified as PCA-3-sulfate and PCA-4-sulfate by mass spectrometry and 1H and 13C nuclear magnetic resonance using one- and two-dimensional techniques (heteronuclear single-quantum coherence and heteronuclear multiple-bond correlation). Differential MS fragmentation behavior and UV spectra were observed for each compound, which could be used for their identification in samples of unknown composition. The described procedure can be used for the preparation of these polyphenol metabolites in view of their use in in vivo and in vitro studies, as well as standards for their analysis in biological fluids, to contribute to the elucidation of biological effects of dietary polyphenols.

scholarly journals Alkoxyalkyl Esters of Cidofovir and Cyclic Cidofovir Exhibit Multiple-Log Enhancement of Antiviral Activity against Cytomegalovirus and Herpesvirus Replication In Vitro

2002 ◽  
Vol 46 (8) ◽  
pp. 2381-2386 ◽  
Author(s):  
James R. Beadle ◽  
Caroll Hartline ◽  
Kathy A. Aldern ◽  
Natalie Rodriguez ◽  
Emma Harden ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Clinical Problem ◽  
The Novel ◽  
Virus Infections ◽  
Treatment And Prevention ◽  
Resistant Strains ◽  
Simplex Virus ◽  
Cmv Disease ◽  
Derivatives Of

ABSTRACT The incidence of cytomegalovirus (CMV) retinitis is declining in AIDS patients but remains a significant clinical problem in patients with organ transplants and bone marrow transplants. Prophylaxis with ganciclovir (GCV) or valganciclovir reduces the incidence of CMV disease but may lead to the emergence of drug-resistant virus with mutations in the UL97 or UL54 gene. It would be useful to have other types of oral therapy for CMV disease. We synthesized hexadecyloxypropyl and octadecyloxyethyl derivatives of cyclic cidofovir (cCDV) and cidofovir (CDV) and found that these novel analogs had 2.5- to 4-log increases in antiviral activity against CMV compared to the activities of unmodified CDV and cCDV. Multiple-log increases in activity were noted against laboratory CMV strains and various CMV clinical isolates including GCV-resistant strains with mutations in the UL97 and UL54 genes. Preliminary cell studies suggest that the increase in antiviral activity may be partially explained by a much greater cell penetration of the novel analogs. 1-O-Hexadecyloxypropyl-CDV, 1-O-octadecyloxyethyl-CDV, and their corresponding cCDV analogs are worthy of further preclinical evaluation for treatment and prevention of CMV and herpes simplex virus infections in humans.

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