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Molecules (Basel, Switzerland) Feb 2022belongs to the genus and is classified as an invasive parasitic plant in agriculture. Despite other species being widely used in herbal medicine due to their... (Review)
Review
belongs to the genus and is classified as an invasive parasitic plant in agriculture. Despite other species being widely used in herbal medicine due to their antimicrobial, antioxidant, antitumor, and anti-inflammatory effects, there are almost no information about the potential of confertus for the treatment of various diseases. In this review we analyzed scientific articles revealing properties of plant's substances against cancer, diabetes, pathogenic bacterial invasions, viruses, inflammation, and oxidative stress for the past 20 years. Compounds dominating in each composition of solvents for extraction were discussed, and common thin layer chromatography(TLC) and high performance liquid chromatography(HPLC) methods for efficient separation of the plant's extract are included. Physico-chemical properties such as solubility, hydrophobicity (Log P), pKa of flavonoids, anthraquinones, and other derivatives are very important for modeling of pharmacokinetic and pharmacodynamics. An overview of clinical studies for abounded selected substances of species is presented.
Topics: Anthraquinones; Anti-Bacterial Agents; Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Flavonoids; Rumex
PubMed: 35208994
DOI: 10.3390/molecules27041204 -
Steroids Sep 2022Aloe-emodin, known as a 3-hydroxymethyl-chrysazin, is one of anthraquinones mainly found in Rheum officinale Baill, Rheum palmatum L and Rheum tanguticum Maxim. Ex BALF.... (Review)
Review
Aloe-emodin, known as a 3-hydroxymethyl-chrysazin, is one of anthraquinones mainly found in Rheum officinale Baill, Rheum palmatum L and Rheum tanguticum Maxim. Ex BALF. In recent studies, aloe-emodin possesses many pharmacological effects, including antitumor, antibacterial, antiviral, anti-inflammatory, cardiovascular protection, liver protection, immune regulation, estrogenic activity as a phytoestrogen, and so on. Cytochrome P450 (CYP) 1B1 (CYP1B1), as a major estrogen metabolizing enzyme, can metabolize 17β-estradiol (E2) to 4-hydroxy-E2 (4-OH-E2), which cause DNA damage and lead to tumor. Few studies have found that anthraquinones possess inhibitory activity against CYP1B1 enzyme. In this study, compared with emodin (3-Hydroxy-6-methyl-chrysazin, CHO), the inhibition of aloe-emodin (3-hydroxymethyl-chrysazin, CHO) on the activity of CYP1B1 was studied. The molecular mechanism of inhibition and the structure-activity relationship were also discussed. Although isomeric, the IC50 values of aloe-emodin and emodin were 0.192 ± 0.015 nM and 0.067 ± 0.003 µM, indicating the inhibition of aloe-emodin was about 350times stronger than that of emodin. Through structure-activity relationship analyses, it revealed the difference of inhibitory activity only due to different hydroxyl positions. When the hydroxyl group is transferred from the chrysazin skeleton to the methyl group, the hydrogen bond formed by this structure with the CYP1B1 protein can change the protein conformation, which may interfere with the binding of the substrate to CYP1B1 protein active site pocket and inhibit the catalytic activity of the CYP1B1 protein. Although the hydroxyl position changed, the inhibition mechanism did not change, all of which were mixed inhibition. This study reveals an anti-tumor mechanism of the anthraquinone compound aloe-emodin.
Topics: Aloe; Anthraquinones; Emodin; Rheum; Structure-Activity Relationship
PubMed: 35661798
DOI: 10.1016/j.steroids.2022.109055 -
Phytomedicine : International Journal... Jul 2024Pancreatitis is a common exocrine inflammatory disease of the pancreas and lacks specific medication currently. Rhei Radix et Rhizoma (RR) and its anthraquinone... (Review)
Review
BACKGROUND
Pancreatitis is a common exocrine inflammatory disease of the pancreas and lacks specific medication currently. Rhei Radix et Rhizoma (RR) and its anthraquinone derivatives (AQs) have been successively reported for their pharmacological effects and molecular mechanisms in experimental and clinical pancreatitis. However, an overview of the anti-pancreatitis potential of RR and its AQs is limited.
PURPOSE
To summarize and analyze the pharmacological effects of RR and its AQs on pancreatitis and the underlying mechanisms, and discuss their drug-like properties and future perspectives.
METHODS
The articles related to RR and its AQs were collected from the Chinese National Knowledge Infrastructure, Wanfang data, PubMed, and the Web of Science using relevant keywords from the study's inception until April first, 2024. Studies involving RR or its AQs in cell or animal pancreatitis models as well as structure-activity relationship, pharmacokinetics, toxicology, and clinical trials were included.
RESULTS
Most experimental studies are based on severe acute pancreatitis rat models and a few on chronic pancreatitis. Several bioactive anthraquinone derivatives of Rhei Radix et Rhizoma (RRAQs) exert local protective effects on the pancreas by maintaining pancreatic acinar cell homeostasis, inhibiting inflammatory signaling, and anti-fibrosis, and they improve systemic organ function by alleviating intestinal and lung injury. Pharmacokinetic and toxicity studies have revealed the low bioavailability and wide distribution of RRAQs, as well as hepatotoxicity and nephrotoxicity. However, there is insufficient research on the clinical application of RRAQs in pancreatitis. Furthermore, we propose effective strategies for subsequent improvement in terms of balancing effectiveness and safety.
CONCLUSION
RRAQs can be developed as either candidate drugs or novel lead structures for pancreatitis treatment. The comprehensive review of RR and its AQs provides references for optimizing drugs, developing therapies, and conducting future studies on pancreatitis.
Topics: Anthraquinones; Animals; Rheum; Humans; Pancreatitis; Drugs, Chinese Herbal; Rhizome; Pancreas; Structure-Activity Relationship; Rats; Disease Models, Animal
PubMed: 38733906
DOI: 10.1016/j.phymed.2024.155708 -
Chemical Communications (Cambridge,... Aug 2023Herein, a Rhein-mineralized microrod crystal (H-RMM) with an ultra-high drug loading capacity was reported for anti-inflammation. Due to a dense crystal structure, the...
Herein, a Rhein-mineralized microrod crystal (H-RMM) with an ultra-high drug loading capacity was reported for anti-inflammation. Due to a dense crystal structure, the H-RMM achieved improved biocompatibility and sustained controlled release of Rhein. Also, the Rhein nanofibers released from H-RMM were favorable to be internalized by cells, leading to enhanced anti-inflammation effects.
Topics: Anti-Inflammatory Agents; Anthraquinones
PubMed: 37534478
DOI: 10.1039/d3cc02527f -
Natural Product Reports Aug 2021This review on atypical angucyclinones possessing an aromatic cleavage of the C-ring covers literature between 1995 and early 2020.The unusual framework of the middle... (Review)
Review
This review on atypical angucyclinones possessing an aromatic cleavage of the C-ring covers literature between 1995 and early 2020.The unusual framework of the middle C-ring, "broken" as a result of biotransformations and oxidations in vivo and bearing an sp-C connection, is of interest for biosynthetic investigations. The reported 39 natural compounds (55 including stereoisomers) have been analyzed and arranged into three structural groups. The biosynthetic origin of all these compounds has been thoroughly reviewed and revised, based on the found connections with oxidized angucyclinone structures. The data on biological activities has been summarized. Careful consideration of the origin of the structure allowed us to outline a hypothesis on the biological function as well as prospective applications of such atypical angucyclinones.
Topics: Anthraquinones; Biosynthetic Pathways; Molecular Structure; Stereoisomerism; Streptomyces
PubMed: 33480893
DOI: 10.1039/d0np00082e -
Ambio Aug 2023The detection of anthraquinone in tea leaves has raised concerns due to a potential health risk associated with this species. This led the European Union to impose a...
The detection of anthraquinone in tea leaves has raised concerns due to a potential health risk associated with this species. This led the European Union to impose a maximum residue limit (MRL) of 0.02 mg/kg for anthraquinone in dried tea leaves. As atmospheric contamination has been identified as one of the possible sources of anthraquinone residue, this study investigates the contamination resulting from the deposition of atmospheric anthraquinone using a global chemical transport model that accounts for the emission, atmospheric transport, chemical transformation, and deposition of anthraquinone on the surface. The largest contribution to the global atmospheric budget of anthraquinone is from residential combustion followed by the secondary formation from oxidation of anthracene. Simulations suggest that atmospheric anthraquinone deposition could be a substantial source of the anthraquinone found on tea leaves in several tea-producing regions, especially near highly industrialized and populated areas of southern and eastern Asia. The high level of anthraquinone deposition in these areas may result in residues in tea products exceeding the EU MRL. Additional contamination could also result from local tea production operations.
Topics: Anthraquinones; Plant Leaves; Food Contamination; Atmosphere; Tea
PubMed: 37115429
DOI: 10.1007/s13280-023-01858-9 -
Molecules (Basel, Switzerland) Oct 2021L., of the Leguminosae family, is used as a diuretic, laxative, tonic, purgative, and natural remedy for treating headache, dizziness, constipation, tophobia, and... (Review)
Review
L., of the Leguminosae family, is used as a diuretic, laxative, tonic, purgative, and natural remedy for treating headache, dizziness, constipation, tophobia, and lacrimation and for improving eyesight. It is commonly used in tea in Korea. Various anthraquinone derivatives make up its main chemical constituents: emodin, chrysophanol, physcion, obtusifolin, obtusin, au rantio-obtusin, chryso-obtusin, alaternin, questin, aloe-emodin, gluco-aurantio-obtusin, gluco-obtusifolin, naphthopyrone glycosides, toralactone-9-β-gentiobioside, toralactone gentiobioside, and cassiaside. . . possesses a wide range of pharmacological properties (e.g., antidiabetic, antimicrobial, anti-inflammatory, hepatoprotective, and neuroprotective properties) and may be used to treat Alzheimer's disease, Parkinson's disease, and cancer. In addition, . L. contributes to histamine release and antiplatelet aggregation. This review summarizes the botanical, phytochemical, and pharmacological features of . and its therapeutic uses.
Topics: Animals; Anthraquinones; Anti-Infective Agents; Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Cassia; Ethnopharmacology; Humans; Hypoglycemic Agents; Liver; Medicine, Korean Traditional; Mosquito Vectors; Neuroprotective Agents; Phytochemicals; Phytotherapy; Plants, Medicinal; Republic of Korea
PubMed: 34684833
DOI: 10.3390/molecules26206252 -
Journal of Molecular Graphics &... Dec 2022A Laplacian scoring algorithm for gene selection and the Gini coefficient to identify the genes whose expression varied least across a large set of samples were the...
A Laplacian scoring algorithm for gene selection and the Gini coefficient to identify the genes whose expression varied least across a large set of samples were the state-of-the-art methods used here. These methods have not been trialed for their feasibility in cheminformatics. This was a maiden attempt to investigate a complete comparative analysis of an anthraquinone and chalcone derivatives-based virtual combinatorial library. This computational "proof-of-concept" study illustrated the combinatorial approach used to explain how the structure of the selected natural products (NPs) undergoes molecular diversity analysis. A virtual combinatorial library (1.6 M) based on 20 anthraquinones and 24 chalcones was enumerated. The resulting compounds were optimized to the near drug-likeness properties, and the physicochemical descriptors were calculated for all datasets including FDA, Non-FDA, and NPs from ZINC 15. UMAP and PCA were applied to compare and represent the chemical space coverage of each dataset. Subsequently, the Laplacian score and Gini coefficient were applied to delineate feature selection and selectivity among properties, respectively. Finally, we demonstrated the diversity between the datasets by employing Murcko's and the central scaffolds systems, calculating three fingerprint descriptors and analyzing their diversity by PCA and SOM. The optimized enumeration resulted in 1,610,268 compounds with NP-Likeness, and synthetic feasibility mean scores close to FDA, Non-FDA, and NPs datasets. The overlap between the chemical space of the 1.6 M database was more prominent than with the NPs dataset. A Laplacian score prioritized NP-likeness and hydrogen bond acceptor properties (1.0 and 0.923), respectively, while the Gini coefficient showed that all properties have selective effects on datasets (0.81-0.93). Scaffold and fingerprint diversity indicated that the descending order for the tested datasets was FDA, Non-FDA, NPs and 1.6 M. Virtual combinatorial libraries based on NPs can be considered as a source of the combinatorial compound with NP-likeness properties. Furthermore, measuring molecular diversity is supposed to be performed by different methods to allow for comparison and better judgment.
Topics: Anthraquinones; Biological Products; Chalcone; Chalcones; Cheminformatics; Combinatorial Chemistry Techniques; Drug Design; Zinc
PubMed: 36096064
DOI: 10.1016/j.jmgm.2022.108307 -
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 -
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