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Chemical constituents of Rumex dentatus L. and their antimicrobial and anti-inflammatory activities.Phytochemistry Jan 2023Antimicrobial bioactivity-guided isolation of the root extract of Rumex dentatus L. resulted in the characterization of nineteen natural products, including three...
Antimicrobial bioactivity-guided isolation of the root extract of Rumex dentatus L. resulted in the characterization of nineteen natural products, including three undescribed compounds (rumexs A-C). Rumexs A and B are rare anthraquinone-anthrone dimers consisting of an emodin-10-C-glycoside linked via C-10 to C-7 of a chrysophanol moiety. They differed only in their configuration at C-10; their absolute configurations were determined by NOESY and ECD analysis. LC-HRMS analysis was performed to identify nineteen compounds. Anthraquinone derivatives such as anthraquinone aglycone, oxanthrone C-glycoside, anthraquinone O-glycoside and anthraquinone dimer were found to be the dominant components of R. dentatus. In addition, naphthol, naphthoquinone, chromone, flavonoid, isocoumarin, and lignanamide derivatives were also identified. Chrysophanol and emodin were the most abundant compounds in the crude ethanol extract; their contents were determined by HPLC to be 7.38 and 5.74 mg/g, respectively. The fractions and isolated compounds were tested for their inhibitory activity against Staphylococcus aureus, Candida albicans, and Escherichia coli. Most of them showed inhibitory activity against S. aureus, some fractions and 2-methoxy-6-acetyl-7-methyljuglone exhibited moderate inhibitory activity against C. albicans, and 2-methoxy-6-acetyl-7-methyljuglone had moderate inhibitory effects against E. coli. Emodin exhibited inhibitory activity against NO release in LPS-reduced RAW264.7 cells in a concentration-dependent manner.
Topics: Rumex; Staphylococcus aureus; Escherichia coli; Anti-Infective Agents; Anthraquinones; Anti-Inflammatory Agents; Plant Extracts
PubMed: 36372239
DOI: 10.1016/j.phytochem.2022.113509 -
Marine Drugs Oct 2022An unreported isocoumarin, (,4)-4-hydroxy-6-methoxymellein (), an undescribed propylpyridinium anthraquinone (), and an unreported C-glucosyl resorcinol derivative,...
New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, KUFA 2017.
An unreported isocoumarin, (,4)-4-hydroxy-6-methoxymellein (), an undescribed propylpyridinium anthraquinone (), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (), were isolated, together with eight previously reported metabolites including -hydroxybenzaldehyde (), 1,3-dimethoxy-8-hydroxy-6-methylanthraquinone (), 1,3-dimethoxy-2,8-dihydroxy-6-methylanthraquinone (), emodin (), 5[(3,5)-nona-3,5-dien-1-yl]benzene (), carnemycin E (), tajixanthone hydrate () and 15-acetyl tajixanthone hydrate (), from the ethyl acetate extract of the culture of a marine sponge-derived fungus, KUFA 2017. The structures of the undescribed compounds were elucidated by 1D and 2D NMR and high resolution mass spectral analyses. In the case of , the absolute configurations of the stereogenic carbons were determined by comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. The absolute configurations of the stereogenic carbons in and were also determined, for the first time, by X-ray crystallographic analysis. Compounds , , , , , , , , and were assayed for antibacterial activity against four reference strains, viz. two Gram-positive ( ATCC 29213, ATCC 29212) and two Gram-negative ( ATCC 25922, ATCC 27853), as well as three multidrug-resistant strains. However, only exhibited significant antibacterial activity against both reference and multidrug-resistant strains. Compound also showed antibiofilm activity against both reference strains of Gram-positive bacteria.
Topics: Animals; Isocoumarins; Porifera; Fungi; Anthraquinones; Anti-Bacterial Agents; Resorcinols; Microbial Sensitivity Tests
PubMed: 36354995
DOI: 10.3390/md20110672 -
Journal of Controlled Release :... Feb 2022Breast cancer is the most common cancer among women and a leading cause of death worldwide. Triple negative breast cancer (TNBC) is a highly aggressive subtype which is...
Breast cancer is the most common cancer among women and a leading cause of death worldwide. Triple negative breast cancer (TNBC) is a highly aggressive subtype which is the most challenging to treat. Due to heterogeneity and a lack of specific molecular targets, small molecule-based chemotherapy is the preferred course of treatment. However, these drugs have high toxicity due to off-target effects on healthy tissues, and tumors may develop resistance. Here, we present a polyethylene glycol-modified nanoscale liposomal formulation (LipoRV) of a new anthraquinone derivative which has potent effects on multiple TNBC cell lines. LipoRV readily inhibited the cell cycle, induced cell apoptosis, and reduced long-term proliferative potential of TNBC cells. In a xenograft animal model, LipoRV successfully cleared tumors and demonstrated a good safety profile, without detrimental effects on biochemical markers. Finally, RNA sequencing of LipoRV-treated TNBC cells was carried out, indicating that LipoRV may have immunomodulatory properties. These findings demonstrate that a liposomal anthraquinone-based molecule has excellent promise for TNBC therapy in the future.
Topics: Animals; Anthraquinones; Apoptosis; Cell Line, Tumor; Cell Proliferation; Female; Humans; Liposomes; Triple Negative Breast Neoplasms; Xenograft Model Antitumor Assays
PubMed: 34896187
DOI: 10.1016/j.jconrel.2021.12.001 -
Chemical Biology & Drug Design Aug 2022Cheminformatics utilizing machine learning (ML) techniques have opened up a new horizon in drug discovery. This is owing to vast chemical space expansion with rocketing... (Review)
Review
Cheminformatics utilizing machine learning (ML) techniques have opened up a new horizon in drug discovery. This is owing to vast chemical space expansion with rocketing numbers of expected hits and lead compounds that match druggable macromolecular targets, in particular from natural compounds. Due to the natural products' (NP) structural complexity, uniqueness, and diversity, they could occupy a bigger space in pharmaceuticals, allowing the industry to pursue more selective leads in the nanomolar range of binding affinity. ML is an essential part of each step of the drug design pipeline, such as target prediction, compound library preparation, and lead optimization. Notably, molecular mechanic and dynamic simulations, induced docking, and free energy perturbations are essential in predicting best binding poses, binding free energy values, and molecular mechanics force fields. Those applications have leveraged from artificial intelligence (AI), which decreases the computational costs required for such costly simulations. This review aimed to describe chemical space and compound libraries related to NPs. High-throughput screening utilized for fractionating NPs and high-throughput virtual screening and their strategies, and significance, are reviewed. Particular emphasis was given to AI approaches, ML tools, algorithms, and techniques, especially in drug discovery of macrocyclic compounds and approaches in computer-aided and ML-based drug discovery. Anthraquinone derivatives were discussed as a source of new lead compounds that can be developed using ML tools for diverse medicinal uses such as cancer, infectious diseases, and metabolic disorders. Furthermore, the power of principal component analysis in understanding relevant protein conformations, and molecular modeling of protein-ligand interaction were also presented. Apart from being a concise reference for cheminformatics, this review is a useful text to understand the application of ML-based algorithms to molecular dynamics simulation and in silico absorption, distribution, metabolism, excretion, and toxicity prediction.
Topics: Anthraquinones; Artificial Intelligence; Biological Products; Cheminformatics; Machine Learning; Molecular Dynamics Simulation
PubMed: 35490393
DOI: 10.1111/cbdd.14062 -
Biotechnology Advances 2023Natural anthraquinones are represented by a large group of compounds. Some of them are widespread across the kingdoms, especially in bacteria, fungi and plants, while... (Review)
Review
Recent advances in the identification of biosynthetic genes and gene clusters of the polyketide-derived pathways for anthraquinone biosynthesis and biotechnological applications.
Natural anthraquinones are represented by a large group of compounds. Some of them are widespread across the kingdoms, especially in bacteria, fungi and plants, while the others are restricted to certain groups of organisms. Despite the significant pharmacological potential of several anthraquinones (hypericin, skyrin and emodin), their biosynthetic pathways and candidate genes coding for key enzymes have not been experimentally validated. Understanding the genetic and epigenetic regulation of the anthraquinone biosynthetic gene clusters in fungal endophytes would help not only understand their pathways in plants, which ensure their commercial availability, but also favor them as promising systems for prospective biotechnological production.
Topics: Polyketides; Epigenesis, Genetic; Prospective Studies; Anthraquinones; Plants; Biosynthetic Pathways; Multigene Family
PubMed: 36716800
DOI: 10.1016/j.biotechadv.2023.108104 -
Bioorganic Chemistry May 2021Morinda (Morinda officinalis) is widely consumed as a health-care herb in Asia and reported to possess various biological activities. In this study, anti-inflammatory...
Morinda (Morinda officinalis) is widely consumed as a health-care herb in Asia and reported to possess various biological activities. In this study, anti-inflammatory phytochemicals were investigated and two pairs of new methyl-2-naphthoate enantiomers (1a/1b, 2a/2b), one new anthraquinone (3), three new natural unknown anthraquinones (5-6, 23), and eighteen known anthraquinones were isolated and elucidated from the roots of morinda. Anti-inflammatory activities of the isolated compounds were assessed in lipopolysaccharide-stimulated RAW 264.7 macrophages. Compounds 2b and 19 significantly inhibited the production of NO with IC values of 34.32 ± 4.87 and 17.17 ± 4.13 μM (indomethacin, IC 26.71 ± 6.32 μM), and they were further corroborated via immunoblotting, quantitative real-time PCR and immunofluorescence staining assays. They could dose-dependent suppress lipopolysaccharide-stimulated pro-inflammatory factors (COX-2 and iNOS) production and block nuclear translocation of NF-κB. The results implied that reasonable consumption of morinda may be beneficial for preventing and reducing the occurrence of inflammatory-associated diseases.
Topics: Animals; Anthraquinones; Anti-Inflammatory Agents, Non-Steroidal; Dose-Response Relationship, Drug; Lipopolysaccharides; Mice; Molecular Structure; Morinda; Naphthalenes; Nitric Oxide; Plant Roots; RAW 264.7 Cells; Structure-Activity Relationship
PubMed: 33761315
DOI: 10.1016/j.bioorg.2021.104800 -
Environmental Research Jul 2023Sulfate radical-based advanced oxidation processes (SR-AOPs) are gaining popularity as a feasible alternative for removing recalcitrant pollutants in an aqueous...
Sulfate radical-based advanced oxidation processes (SR-AOPs) are gaining popularity as a feasible alternative for removing recalcitrant pollutants in an aqueous environment. Persulfates, namely peroxydisulfate (PDS) and peroxymonosulfate (PMS) are the most common sulfate radical donors. Persulfates activation by ultraviolet (UV) irradiation is considered feasible due to the high concentration of radicals produced as well as the lack of catalysts leaching. The research focuses on determining the impact of activated PDS and PMS on the degradation of anthraquinone dye, i.e., Acid Blue 129 (AB129). UV-activated PDS and PMS can quickly degrade the AB129 as well as restrict the formation of by-products. This could explain the reduced ecotoxicity levels of the treated water after degradation, using an aquatic plant (Lemna minor) and a crustacean (Daphnia magna). This, on the other hand, can ensure that the sulfate radical-based processes can be an environmentally friendly technology.
Topics: Kinetics; Water Pollutants, Chemical; Oxidation-Reduction; Anthraquinones; Water Purification
PubMed: 37062479
DOI: 10.1016/j.envres.2023.115910 -
Chemical & Pharmaceutical Bulletin 2022Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together...
Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together with 6-methoxycomaparvin-5-methylether-8-O-sodium sulfate (6), 6-methoxycomaparvin-8-O-sodium sulfate (7), comaparvin-8-O-sodium sulfate (8), and 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone-6-O-sodium sulfate (9) were isolated from the Vietnamese crinoid Comanthus delicata. Their chemical structures were elucidated by extensive analysis of the one dimensional (1D) and 2D-NMR, high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra as well as calculation of optical rotation. In addition, significant cytotoxicity was observed for 6 against LNCaP (prostate cancer) cell line with IC value of 20.29 ± 2.43 µM, whereas moderate or weak cytotoxic effects were observed for 1-3 and 5-8 on SK-Mel-2 (melanoma) cell line and 7 and 8 against LNCaP cell line, with IC values ranging from 49.96 ± 1.74 to 76.92 ± 5.85 µM.
Topics: Animals; Anthraquinones; Antineoplastic Agents; Asian People; Echinodermata; Humans; Neoplasms
PubMed: 35491198
DOI: 10.1248/cpb.c21-00904 -
International Journal of Environmental... Jan 2022is a famous medicinal plant that is widely used in Asian countries. Its seed plays an important role in the treatment of many diseases because it contains various...
is a famous medicinal plant that is widely used in Asian countries. Its seed plays an important role in the treatment of many diseases because it contains various anthraquinones and flavonoids. Our previous studies have indicated that three space environment-induced lines (SP-lines) i.e., QC10, QC29, and QC46, have higher seed yield and aurantio-obtusin (AO) content. However, the underlying mechanism of higher AO content in SP-lines is still unknown. Herein, transcriptome sequencing and HPLC were employed to analyze the differences between SP-lines and ground control (GC3) and elucidate the regulatory mechanisms of AO accumulation in SP-lines. The results show that 4002 differentially expressed genes (DEGs) were identified in SP-lines versus (vs.) GC3. DEGs in the QC10 vs. GC3, QC29 vs. GC3, and QC46 vs. GC3 comparisons were classified into 28, 36, and 81 GO terms and involved in 63, 74, and 107 Kyoto Encyclopedia of Genes and Genomes (KEGG) pathways. KEGG pathway and gene expression analysis revealed that DEGs involved in anthraquinone pathways were significantly elevated in QC10 and QC46. Integrating the results of GO annotation, KEGG enrichment, and gene expression analysis, we propose that the elevated genes such as , , and enhance the metabolic flux in the anthraquinone pathway and promote AO content in QC10 and QC46. Taken together, this study elucidated the mechanism of AO content in SP-lines and provides valuable genetic information for . In addition, to the best of our knowledge, this study presents the first transcriptome analysis of environment-induced medicinal plants and paves the way to select elite varieties in the future.
Topics: Anthraquinones; Cassia; Chromatography, High Pressure Liquid; Gene Expression Profiling; Transcriptome
PubMed: 35055719
DOI: 10.3390/ijerph19020898 -
International Journal of Molecular... Sep 2021Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a naturally occurring anthraquinone derivative found in roots and leaves of various plants, fungi and lichens. For a... (Review)
Review
Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a naturally occurring anthraquinone derivative found in roots and leaves of various plants, fungi and lichens. For a long time it has been used in traditional Chinese medicine as an active ingredient in herbs. Among other sources, it is isolated from the rhubarb or tuber fleece-flower . Emodin has a wide range of biological activities, including diuretic, antibacterial, antiulcer, anti-inflammatory, anticancer and antinociceptive. According to the most recent studies, emodin acts as an antimalarial and antiallergic agent, and can also reverse resistance to chemotherapy. In the present work the potential therapeutic role of emodin in treatment of inflammatory diseases, cancers and microbial infections is analysed.
Topics: Emodin; Humans; Infections; Inflammation; Neoplasms; Rheum
PubMed: 34502424
DOI: 10.3390/ijms22179522