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Organic Letters Sep 2021Total syntheses of aturanosides A and B, two antiangiogenic anthraquinone glycosides, have been achieved in an expeditious manner, highlighting anthraquinone synthesis,...
Total syntheses of aturanosides A and B, two antiangiogenic anthraquinone glycosides, have been achieved in an expeditious manner, highlighting anthraquinone synthesis, phenol glycosylation, α-d-glucosaminoside installation, and judicious use of protecting groups.
Topics: Angiogenesis Inhibitors; Anthraquinones; Glycosides; Glycosylation; Molecular Structure
PubMed: 34383489
DOI: 10.1021/acs.orglett.1c02244 -
Journal of the American Chemical Society Nov 2022First discovered in 1989, the anthraquinone-fused enediynes are a class of DNA-cleaving bacterial natural products composed of a DNA-intercalating anthraquinone moiety...
First discovered in 1989, the anthraquinone-fused enediynes are a class of DNA-cleaving bacterial natural products composed of a DNA-intercalating anthraquinone moiety and a 10-membered enediyne warhead. However, until recently, there has been a lack of genetically amenable hosts and sequenced biosynthetic gene clusters available for solving the biosynthetic questions surrounding these molecules. Herein, we have identified and biochemically and structurally characterized TnmK1, a member of the α/β-hydrolase fold superfamily responsible for the C-C bond formation linking the anthraquinone moiety and enediyne core together in tiancimycin (TNM) biosynthesis. In doing so, two intermediates, TNM H and TNM I, in anthraquinone-fused enediyne biosynthesis, containing an unprecedented cryptic C16 aldehyde group, were identified. This aldehyde plays a key role in the TnmK1-catalyzed C-C bond formation via a Michael addition, representing the first example of this chemistry for the α/β-hydrolase fold superfamily. Additionally, TNM I shows sub-nanomolar cytotoxicity against selected cancer cell lines, indicating a new mechanism of action compared to previously known anthraquinone-fused enediynes. Together, the findings from this study are expected to impact enzymology, natural product biosynthesis, and future efforts at enediyne discovery and drug development.
Topics: Enediynes; Anthraquinones; Biological Products; Hydrolases; Aldehydes
PubMed: 36279548
DOI: 10.1021/jacs.2c08957 -
Natural Product Research May 2021An unusual, new anthracene natural product named filamentos A (), two new anthraquinone derivatives named filamentos B () and C (), together with sixteen known compounds...
An unusual, new anthracene natural product named filamentos A (), two new anthraquinone derivatives named filamentos B () and C (), together with sixteen known compounds (-), were isolated from the roots of the tree . Their structures were identified by analysis of mass and spectroscopic data (IR, 1D and 2D NMR). Twelve metabolites (-, , -, -) showed moderate antibacterial activities against a wide range of Gram-positive and Gram-negative bacteria such as . , . , . , . , . and . .
Topics: Anthracenes; Anthraquinones; Anti-Bacterial Agents; Bacteria; Carbon-13 Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Plant Roots; Proton Magnetic Resonance Spectroscopy; Rubiaceae
PubMed: 31177846
DOI: 10.1080/14786419.2019.1627352 -
European Journal of Pharmacology May 2021Rhein is one of the anthraquinones components of Rheum. It shows excellent clinical efficacy and is widely used in the management of several disease conditions including... (Review)
Review
Rhein is one of the anthraquinones components of Rheum. It shows excellent clinical efficacy and is widely used in the management of several disease conditions including tumors, inflammation, diabetic nephropathy, and viral infections. In this review, we summarize the recent studies on the pharmacological activities of rhein and its derivatives, as well as their association with different diseases and possible mechanisms based on our previous review. This review serves as an updated and a supplement to our previous report highlighting the use of rhein in nanotechnology. It also serves as a reference study and offers an overall picture of the use of rhein and its derivatives in nanotechnology.
Topics: Animals; Anthraquinones; Drug Carriers; Drug Compounding; Humans; Nanomedicine; Nanoparticles; Polymers
PubMed: 33515540
DOI: 10.1016/j.ejphar.2021.173908 -
Molecules (Basel, Switzerland) Sep 2022We report the use of electrogenerated anthraquinone radical anion (AQ•) to trigger fast catalytic depolymerization of polymers derived from poly(dithiothreitol)...
We report the use of electrogenerated anthraquinone radical anion (AQ•) to trigger fast catalytic depolymerization of polymers derived from poly(dithiothreitol) (pDTT)-a self-immolative polymer (SIP) with a backbone of dithiothreitols connected with disulfide bonds and end-capped via disulfide bonds to pyridyl groups. The pDTT derivatives studied include polymers with simple thiohexyl end-caps or modified with AQ or methyl groups by Steglich esterification. All polymers were shown to be depolymerized using catalytic amounts of electrons delivered by AQ•. For pDTT, as little as 0.2 electrons per polymer chain was needed to achieve complete depolymerization. We hypothesize that the reaction proceeds with AQ• as an electron carrier (either molecularly or as a pendant group), which transfers an electron to a disulfide bond in the polymer in a dissociative manner, generating a thiyl radical and a thiolate. The rapid and catalytic depolymerization is driven by thiyl radicals attacking other disulfide bonds internally or between pDTT chains in a chain reaction. Electrochemical triggering works as a general method for initiating depolymerization of pDTT derivatives and may likely also be used for depolymerization of other disulfide polymers.
Topics: Anions; Anthraquinones; Disulfides; Dithiothreitol; Polymers
PubMed: 36234828
DOI: 10.3390/molecules27196292 -
Structure (London, England : 1993) May 2023In this issue of Structure, Huber et al. identify five O-methyltransferases, and three of them catalyze the sequential methylation of the Gram-negative...
In this issue of Structure, Huber et al. identify five O-methyltransferases, and three of them catalyze the sequential methylation of the Gram-negative bacterium-derived aromatic polyketide anthraquinone AQ-256. They present co-crystal structures with bound AQ-256 and its methylated derivatives, which explains the specificities of these O-methyltransferases.
Topics: Methyltransferases; Methylation; Anthraquinones
PubMed: 37146572
DOI: 10.1016/j.str.2023.04.006 -
Pharmaceutical Biology Dec 2020Acetylshikonin, a naphthoquinone derivative, is mainly extracted from some species of the family Boraginaceae, such as Sieb. et Zucc., (Royle) Johnst., and Bunge. As... (Review)
Review
CONTEXT
Acetylshikonin, a naphthoquinone derivative, is mainly extracted from some species of the family Boraginaceae, such as Sieb. et Zucc., (Royle) Johnst., and Bunge. As a bioactive compound, acetylshikonin has attracted much attention because of its broad pharmacological properties.
OBJECTIVE
This review provides a comprehensive summary of the pharmacology, toxicity, and pharmacokinetics of acetylshikonin focussing on its mechanisms on the basis of currently available literature.
METHODS
The information of acetylshikonin from 1977 to 2020 was collected using major databases including Elsevier, Scholar, PubMed, Springer, Web of Science, and CNKI. Acetylshikonin, pharmacology, toxicity, pharmacokinetics, and naphthoquinone derivative were used as key words.
RESULTS
According to emerging evidence, acetylshikonin exerts a wide spectrum of pharmacological effects such as anticancer, anti-inflammatory, lipid-regulatory, antidiabetic, antibacterial, antifungal, antioxidative, neuroprotective, and antiviral properties. However, only a few studies have reported the adverse effects of acetylshikonin, with respect to reproductive toxicity and genotoxicity. Pharmacokinetic studies demonstrate that acetylshikonin is associated with a wide distribution and poor absorption.
CONCLUSIONS
Although experimental data supports the beneficial effects of this compound, acetylshikonin cannot be considered as a therapy drug without further investigations, especially, on the toxicity and pharmacokinetics.
Topics: Animals; Anthraquinones; Boraginaceae; Drugs, Chinese Herbal; Humans; Mice; Naphthoquinones; Plant Extracts; Rats
PubMed: 32956595
DOI: 10.1080/13880209.2020.1818793 -
Chinese Journal of Natural Medicines Jun 2020Emodin (1, 3, 8-trihydroxy-6-methylanthraquinone) is a derived anthraquinone compound extracted from roots and barks of pharmaceutical plants, including Rheum palmatum,... (Review)
Review
Emodin (1, 3, 8-trihydroxy-6-methylanthraquinone) is a derived anthraquinone compound extracted from roots and barks of pharmaceutical plants, including Rheum palmatum, Aloe vera, Giant knotweed, Polygonum multiflorum and Polygonum cuspidatum. The review aims to provide a scientific summary of emodin in pharmacological activities and toxicity in order to identify the therapeutic potential for its use in human specific organs as a new medicine. Based on the fundamental properties, such as anticancer, anti-inflammatory, antioxidant, antibacterial, antivirs, anti-diabetes, immunosuppressive and osteogenesis promotion, emodin is expected to become an effective preventive and therapeutic drug of cancer, myocardial infarction, atherosclerosis, diabetes, acute pancreatitis, asthma, periodontitis, fatty livers and neurodegenerative diseases. This article intends to provide a novel insight for further development of emodin, hoping to reveal the potential of emodin and necessity of further studies in this field.
Topics: Anthraquinones; Emodin; Humans; Molecular Structure; Plant Bark; Plant Extracts; Plant Roots
PubMed: 32503734
DOI: 10.1016/S1875-5364(20)30050-9 -
Chemosphere Jan 2021The long-term stability of aerobic granules is critical for decolourization of different dyes in textile wastewater. Here, we investigated dye decolourization and the...
The long-term stability of aerobic granules is critical for decolourization of different dyes in textile wastewater. Here, we investigated dye decolourization and the stability of acetate-cultivated granules after exposure to dyes. Results show that granules can maintain excellent structure stability with the presence of azo and triphenylmethane dyes during a 200-day operation period, achieving biomass concentrations as high as 8-12 g L and 90% and 100% decolourization efficiency, respectively. Aerobic granules, however, partially disintegrated after exposure to anthraquinone, resulting in dye decolourization efficiency ranging from 50 to 80% and a biomass concentration as low as around 0.5 g L due to biomass wash-out. The study indicates that long-term granule stability is much dependent on the dye classes. The enrichment of specific species in granules for dye decolourization has not been affected by the granule structure. The specific dye decolourization rate and dye to microorganism ratio for anthraquinone were 5-6.5 and 13.5-16.4 times, respectively, higher than those for azo and triphenylmethane dyes, but the total reactor performance for anthraquinone decolourization is much poorer than azo and triphenylmethane dyes due to low biomass retention in the reactor. The results suggest the importance of stability of aerobic granules for biomass retention to achieve better treatment performance of dye-containing wastewater. For the first time, the long-term stability and decolourization performance of aerobic granules for treating anthraquinone and triphenylmethane dyes are reported here and compared with azo dye, which can be used to guide the treatment of real textile wastewater containing azo, anthraquinone and triphenylmethane dyes by aerobic granules.
Topics: Acclimatization; Anthraquinones; Azo Compounds; Coloring Agents; Trityl Compounds
PubMed: 33297248
DOI: 10.1016/j.chemosphere.2020.128312 -
Chemico-biological Interactions Sep 2019Anthraquinones constitute an important class of natural and synthetic compounds with a broad scope of pharmacological including anti-bacterial, antioxidant, laxative,... (Review)
Review
Anthraquinones constitute an important class of natural and synthetic compounds with a broad scope of pharmacological including anti-bacterial, antioxidant, laxative, anti-tumor and other activities. Physcion and physcion 8-O-β-glucopyranoside (PG) are common anthraquinones existed in various plants. Emerging studies suggested that physcion and PG not only exert anti-tumor, anti-microbial, anti-inflammatory, anti-oxidant, optical-related, enzyme inhibitory, lipid regulation and neuroprotective activities, but also lead to hepatotoxicity, renal toxicity and genetic damage. Besides, a growing number of pharmacokinetics researches of physcion and PG also have been conducted. However, no review of physcion or PG have been published by now, so the aim of present review is to give a comprehensive summary and analysis of the pharmacology, toxicity and pharmacokinetics of physcion and PG by consulting all the currently available literatures published in PubMed then give a future prospects about it.
Topics: Anthraquinones; Emodin; Glucosides; Phytochemicals
PubMed: 31226286
DOI: 10.1016/j.cbi.2019.06.035