Anthraquinone Research Articles

Genome-wide analysis of MYB transcription factors in four Rheum L. plants provides new insights into the synthesis of Anthraquinones

R. tanguticum (Rheum tanguticum Maxim. ex Regel) is a herbaceous plant belonging to Polygonaceae family and Rheum L. genus. It holds considerable value in culinary and medicinal realms, primarily due to their rich Anthraquinones (AQs) content. Understanding the molecular mechanisms that regulate AQs biosynthesis is a prerequisite for increasing their yield. MYB transcription factors (TFs) can regulate the synthesis of a variety of plant secondary metabolites. However, only a few research have explored the role of MYB TFs in Rheum L. species. In this study, 1054 MYB genes from four Rheum L. species were identified. The number of MYB genes in each species was similar, distributed across 11 chromosomes. To investigate the phylogeny of identified MYB TFs, they were classified into four subfamilies. Sequence characteristics, phylogenetic relationships, evolutionary trends, and tissue expression of MYB genes in Rheum L. species were further studied. Subsequently, 12 MYB genes were selected, which shown differential expression in different tissues. Further research on these genes indicated a significant correlation with genes in shikimate pathway and polyketide pathway of AQs biosynthesis. Protein-protein interaction simulations in Arabidopsis thaliana and qRT-PCR experiments further confirmed this situation. This research lays the foundation for studying molecular mechanisms by which MYB TFs regulates AQs biosynthesis in four Rheum L. species.

Layer-by-layer coating strategy to functionalize the magnetic nanoparticles for their multi-functionalization

Magnetic nanoparticles (MNPs) hold significant potential for a wide range of applications, however, surface modification or bio-conjugation of MNPs often leads to their aggregation and instability. To address this, we proposed a facile method using a layer-by-layer (LbL) coating technique with polyallylamine hydrochloride (PAH) and poly(styrene sulfonic acid) sodium salt (PSS), so as to maintain the dispersion stability and functionality of MNPs. This method enabled us to develop the powerful MNPs towards to their use in the electrochemical biosensor, by combining both the redox probes (ferrocene (Fc), anthraquinone (AQ), or monocarboxymethylene blue (MB)) and bio-probes (IgG). The redox molecules were effectively anchored to the MNPs under the organic solvents, while such functionalized MNPs surface were subsequently protected by the LbL coating process prior to dispersing in high ionic strength solutions (e.g. Phosphate-buffered saline). And the out-layer of polyelectrolyte shell allowed biomolecules to attach to the MNP surface without chemical cross-linking. Our results demonstrated that the TEM size of MNPs@Fc, MNP@AQ and MNP@MB after LbL coating were characterized as 11.0 ± 2.0 nm, 10.5 ± 2.1 nm and 12.4 ± 2.2 nm and these developed redox MNPs of MNPs@Fc, MNPs@AQ and MNPs@MB were characterized by square wave voltammetry (SWV) with their redox intensity of 0.64 ± 0.10 µA, 23.25 ± 0.73 µA and 0.48 ± 0.13 µA, respectively. In addition, the binding efficiency of adsorption between the MNPs and IgG was up to 78%, evidenced by SDS-PAGE gel analysis. This facile method offered a versatile and effective way to functionalize MNPs, combining redox and biological properties for potential applications in disease diagnosis and point-of-care diagnostics.

Exploration of Basidiomycetes for Anthraquinone Dyes Decolorization in Textile Wastewater.

Anthraquinone (AQ) dyes are utilized extensively in the textile industry due to their ability to fasten fabrics. The intricate and rigid structures of AQ dyes, however, prevent them from biodegradation. They also create nitrate residues, which persist as effluents in textile wastewater and harm aquatic vegetation by obstructing light from entering the water, which affects both flora and fauna. The use of bioremediation technique is most popular because it is environmentally beneficial and economical. The aim of this study was to isolate white rot fungi (WRF) for their ability to decolorize AQ dyes and their mixtures. The current study shows the decolorization of mixture of AQ dyes (MAQD), namely, Acid blue 129 (AB129), Alizarin cyanin green (ACG), and Remazol brilliant blue R (RBBR) (200ppm) under optimized parameters: pH 7, temperature 30°C, and shaking speed 80rpm in 24h by using suspended fungal isolates, VS12 (93.71%) and WF2 (92.76%) isolated from decaying wood. The highest manganese peroxidase (MnP) activity (2391.77U/mL) was found in VS12 followed by WF2 (2318.28U/mL) in 24h. Moreover, the study revealed that MnP is one of the causes for decolorization of MAQD, as decolorization is directly proportional to MnP activity. On the basis of morphological features and a complete sequence analysis of 18S rRNA gene and internal transcribed spacer (ITS) region, the isolates were identified as Trametes cubensis WF2 and Polyporus umbellatus VS12. This is the first report of white rot fungal isolates T. cubensis WF2 and P. umbellatus VS12 used in efficient decolorization of MAQD (AB129, ACG, RBBR).

Analgesic Mechanism of Emodin in Neuropathic Pain Through Inhibiting P2X4 Purinoceptor Signaling.

Neuropathic pain (NeP) is a most intractable health problem due to its unsatisfactory treatment effect. Emodin, a natural anthraquinone derivative extracted from Rheum palmatum and Polygonam cuspidatum, exhibits the analgesic effects in various NeP models. However, the underlying mechanisms remain elusive. This study employed whole transcriptome sequencing and metabolomics to elucidate emodin's analgesic mechanism in the spinal cord of chronic constriction injury (CCI) rats. Fifteen-day emodin treatment reversed hyperalgesia and deficit of sciatic nerve function induced by CCI and significantly decreased the concentrations of TNF-α, IL- 1β, IL- 6, IL- 18, and BDNF in the spinal cord of the CCI rats. Transcriptome sequencing revealed altered expression of 85 mRNAs in the spinal cord of emodin-treated and CCI rats, with 53 mRNAs upregulated and 32 mRNAs downregulated. Notably, seven genes (P2RX4, CXCL10, ALOX5, SCN4 A, AURKB, AQP9) overlapped with established NeP targets. Untargeted metabolomic analyses identified 67 significantly altered metabolites (46 upregulated, 32 downregulated) in the spinal cord upon emodin treatment. Integrative analysis highlighted shared pathways between differentially expressed genes and metabolites, including arachidonic acid metabolism, cAMP signaling pathway, and Fc epsilon RI signaling pathway. Western blot and immunofluorescent staining further proved the decreased expression of IBA1, P2X4R, p38 MAPK, p-p38 MAPK, NF-κB, p-NF-κB, and TNF-α, IL- 1β. In conclusion, this study demonstrated that emodin played the analgesic effect in the CCI rats, possibly through suppression of P2X4 purinoceptor signaling in spinal microglia, suggesting a potential therapeutic target for NeP.

Laccaic Acid A: A Natural Anthraquinone with Potent Anticancer Activity against MDA-MB-231 Cells

Aim: This study aims to isolate and evaluate the anticancer potential of laccaic acids from lac dye by utilizing polarity-based fractionation and high-performance liquid chromatography (HPLC). Methods: In this study, polarity-based fractionation of lac dye was performed to isolate its constituents. A novel HPLC method was developed for the chromatographic separation of lac dye components, utilizing gradient elution with two solvents: 0.1% (v/v) formic acid in LCMS-grade water (A) and 90:10 acetonitrile HPLC-grade (B) at a flow rate of 0.4 mL/min. This method facilitated the isolation of four key constituents: laccaic acid D, laccaic acid B, laccaic acid C, and laccaic acid A. Result: The purity of these compounds was confirmed via LCMS methods. The anticancer activity of the isolated constituents was evaluated against the MDA-MB-231 cell line using the MTT assay. Notably, laccaic acid A demonstrated significant anticancer activity with an IC50 value of less than 100 nM, comparable to that of Adriamycin. Further investigations into the apoptotic activity of laccaic acid A were conducted using flow cytometry, revealing that laccaic acid A is a non-necrotic and apoptotic inducer. Additionally, considering that an effective anticancer agent may also exhibit antioxidant, anti-inflammatory, and anti-angiogenesis properties, the isolated laccaic acids were accessed for these biological activities. Conclusion: The results were promising, indicating that laccaic acids could offer a multifaceted approach to cancer treatment. This study highlights the potential of laccaic acids as valuable candidates for anticancer therapy and warrants further investigation into their mechanisms of action and therapeutic efficacy.

High-Rate Quinone Cathodes and Nafion Conditioning for Improved Stability in Aqueous Zinc-Ion Batteries.

The growing need for fast and reliable energy delivery in various applications ranging from electric vehicles and portable electronics to grid-scale storage demands high-performance energy storage systems capable of operating at high charge/discharge rates (C-rates). Aqueous zinc-ion batteries (AZIBs) offer a promising alternative to conventional lithium-ion batteries primarily due to their inherent safety, environmental friendliness, low cost, and high theoretical capacity. Quinone-based cathodes, with their fast redox kinetics and high theoretical capacities, are particularly suitable for high-rate applications. However, their practical application in AZIBs is limited by their high solubility in aqueous electrolytes, leading to significant capacity fading and poor long-term cycling stability, especially at elevated C-rates. To address these challenges, this study investigates the use of Nafion membranes as ion-selective barriers to stabilize quinone cathodes and prevent the dissolution of active materials. The study evaluates four quinone-based cathodes─2,3,5,6-tetrachloro-1,4-benzoquinone (TCBQ), 1,4-naphthoquinone (NQ), anthraquinone (AQ), and poly(2-chloro-3,5,6-trisulfide-1,4-benzoquinone) (PCTBQ)─in AZIBs, focusing on the effect of Nafion membrane conditioning in 1 M ZnSO4 electrolyte. The results demonstrate that optimized Nafion conditioning significantly enhances the stability and performance of quinone cathodes, reducing dissolution, improving cyclability, and maintaining stable capacity retention under high-rate conditions, i.e., 35C. These findings emphasize the importance of membrane conditioning and demonstrate its potential to advance the development of durable, high-rate AZIBs for rapid energy storage applications.

Artificial α-amino acid based on cysteine grafted natural aloe-emodin for aqueous organic redox flow batteries

Natural redox-active anthraquinone derivatives possess promising attributes for applications in aqueous organic redox flow batteries (AORFBs) due to their environmental friendliness and abundant sources. However, their limited aqueous solubility and electrochemical stability have posed significant challenges to their practical utilization. Herein, inspired by click chemistry, we report the synthesis of an artificial α-amino acid derived from cysteine-functionalized natural aloe-emodin (namely Cys-AE), which exhibits good water-solubility and redox-reversibility, particularly suited for alkaline AORFBs. The bio-inspired Cys-AE molecule exhibits a threefold increase in aqueous solubility compared to pristine aloe-emodin. Furthermore, the AORFB based Cys-AE negolyte with an electron concentration of 1.0 M demonstrates a low capacity fade rate of 0.000948% cycle−1 (equivalent to 0.0438% day−1) during 592 cycles, significantly outperforming the AORFB based on pristine aloe-emodin (0.00446% cycle−1, or 0.908% day−1) during 1564 cycles. Our investigation incorporates time-dependent density functional theory (TDDFT) simulations and detailed spectroscopic analyses reveal the essential role played by the asymmetric distribution of multiple solubilizing groups in enhancing the aqueous solubility and cycling stability of Cys-AE. This study highlights the potential of nature-inspired molecular engineering strategies in creating and crafting redox-reversible organic species poised to revolutionize large-scale and sustainable energy storage applications.

Efficient Photosynthesis of Hydrogen Peroxide from Water and Air Over Water-Dispersible Anthraquinone-Based Porous Aromatic Frameworks.

Photosynthesis of hydrogen peroxide from earth-abundant water and air over organo-based semiconducting materials is a promising alternative to the traditional anthraquinone (AQ) method. However, the generally hydrophobic nature of organic semiconductors has led to their poor dispersibilities in aqueous systems, which built huge barriers for photon capture and reactant contact in water-based photocatalysis. Aiming at this issue, this study reports the facile synthesis of AQ-based porous aromatic frameworks (AQ-PAFs) by coupling AQ fragments with thiophene-derived linkers via robust carbon-carbon bonds. Remarkably, the interfacial hydrogen bonding interactions between water molecules and AQ sites on the surface improve the general hydrophilicity of AQ-PAFs, which can be well-dispersed in water-only systems with uniform particle size distributions. Moreover, the AQ moieties also function as mediators of photoinduced electrons, and the protons produced from water oxidation reaction (WOR), which would kinetically favor the charge separation and subsequent electron transfer reactions. The mono-dispersed AQ-PAF photocatalyst promotes hydrogen peroxide (H2O2) photosynthesis from water and air under visible light achieving a high productivity of 7124µmol g-1h-1 in the absence of any organic alcohol reagents among organic semiconductor photocatalysts. Furthermore, a continuous H2O2 photosynthesis for 190h is also achieved in a flow system.

Efficient Photosynthesis of Hydrogen Peroxide from Water and Air Over Water‐Dispersible Anthraquinone‐Based Porous Aromatic Frameworks

AbstractPhotosynthesis of hydrogen peroxide from earth‐abundant water and air over organo‐based semiconducting materials is a promising alternative to the traditional anthraquinone (AQ) method. However, the generally hydrophobic nature of organic semiconductors has led to their poor dispersibilities in aqueous systems, which built huge barriers for photon capture and reactant contact in water‐based photocatalysis. Aiming at this issue, this study reports the facile synthesis of AQ‐based porous aromatic frameworks (AQ‐PAFs) by coupling AQ fragments with thiophene‐derived linkers via robust carbon–carbon bonds. Remarkably, the interfacial hydrogen bonding interactions between water molecules and AQ sites on the surface improve the general hydrophilicity of AQ‐PAFs, which can be well‐dispersed in water‐only systems with uniform particle size distributions. Moreover, the AQ moieties also function as mediators of photoinduced electrons, and the protons produced from water oxidation reaction (WOR), which would kinetically favor the charge separation and subsequent electron transfer reactions. The mono‐dispersed AQ‐PAF photocatalyst promotes hydrogen peroxide (H2O2) photosynthesis from water and air under visible light achieving a high productivity of 7124 µmol g−1 h−1 in the absence of any organic alcohol reagents among organic semiconductor photocatalysts. Furthermore, a continuous H2O2 photosynthesis for 190 h is also achieved in a flow system.

Emodin and Aloe-Emodin Reduce Cell Growth and Disrupt Metabolic Plasticity in Human Melanoma Cells.

Background/Objectives: Melanoma is an aggressive skin cancer with intratumor metabolic heterogeneity, which drives its progression and therapy resistance. Natural anthraquinones, such as emodin and aloe-emodin, exhibit anti-cancer properties, but their effects on metabolic plasticity remain unclear. This study evaluated their impact on proliferation and metabolic pathways in heterogenous melanoma human cell lines. Methods: COLO 800, COLO 794, and A375 melanoma cell lines representing distinct metabolic phenotypes were analyzed. Targeted and untargeted metabolomics analyses integrated with Seahorse assays were performed to assess the effects of emodin and aloe-emodin on cell proliferation, mitochondrial function, and redox homeostasis. Glucose tracing using [U-13C6] glucose and metabolic flux analysis (MFA) were carried out to evaluate the glycolysis and TCA cycle dynamics. Results: Emodin and aloe-emodin inhibited proliferation by disrupting glycolysis, oxidative phosphorylation, and energy production across all cell lines. Both compounds impaired glucose metabolism, reduced TCA cycle intermediates, and induced mitochondrial ROS accumulation, causing oxidative stress and redox imbalance. Despite intrinsic metabolic differences, COLO 800 and COLO 794 upregulated antioxidant defenses; A375 enhanced one-carbon metabolism and amino acid pathways to maintain redox balance and nucleotide biosynthesis. Conclusions: Emodin and aloe-emodin can disrupt the metabolic plasticity of melanoma cells by impairing glycolysis, mitochondrial function, and redox homeostasis. Their ability to target metabolic vulnerabilities across diverse phenotypes highlights their therapeutic potential for overcoming resistance mechanisms and advancing melanoma treatment strategies.

Effectiveness of hCG and Aromatase Inhibitors Before Micro TESE in Men with Non-Obstructive Azoospermia

Diabetes mellitus, particularly type 2 diabetes, is a growing global health issue, often exacerbated by insulin resistance, metabolic disturbances, and inflammatory responses. Emodin, a natural anthraquinone derivative, has been widely recognized for its

Characterization of Five Natural Anthraquinone Compounds as Potent Inhibitors against CYP1B1: Implications for Cancer Treatment.

Human cytochrome P450 1B1 (CYP1B1) is an extrahepatic enzyme that is overexpressed in many tumors and is associated with tumor development and acquired resistance. Few studies have reported that anthraquinone compounds have inhibitory activity against the CYP1B1 enzyme. Cassiae semen (Leguminosae) is a well-known traditional Chinese medicine containing more than 70 compounds. The crude extracts and pure compounds of Cassiae semen have been widely used in preclinical and clinical practice for their beneficial effects, such as neuroprotective, hepatoprotective, antimicrobial, antioxidant, and hypotensive effects. Aloe-emodin, chrysophanol, obtusifolin, aurantio-obtusin, and rhein are important active natural anthraquinones in Cassiae semen. Aloe-emodin, chrysophanol, obtusifolin, aurantio-obtusin, and rhein have a wide range of pharmacological activities and have been found to have good anti-tumor and antioxidant effects. However, the underlying mechanisms of these pharmacological activities remain poorly understood. This study aimed to investigate the inhibitory effects of five natural anthraquinones on the activity of CYP1B1 and to analyze the structure- activity relationship of these compounds. In this study, 7-ethoxyresorufin O-deethylation (EROD) was used as the fluorescent substrate of CYP1B1 to investigate the inhibition effect, and molecular docking was performed to further determine the structural-activity relationship of the compound molecules. We found that aloe-emodin and chrysophanol had strong inhibitory effects on CYP1B1 with IC50 values of 0.28 and 0.34μM, respectively, while obtusifolin and aurantio-obtusin had IC50 values of 0.77μM and 9.11μM, respectively. The structural activity analysis showed that the inhibition strength was related to the position of the hydroxyl group substitution and the number of methoxy group substitutions. Rhein containing one carboxyl group showed the weakest inhibition of 23.72μM. The inhibition kinetics showed that all five compounds belonged to the non-competitive inhibition model. The inhibition kinetics revealed that all five compounds exhibited the non-competitive inhibition model. The present study provided a comprehensive analysis of the inhibitory effects of five natural anthraquinones, namely aloe-emodin, chrysophanol, obtusifolin, aurantio-obtusin and rhein, on CYP1B1 activity, and elucidated the structure-activity relationship. Molecular docking simulations further revealed the specific amino acid residues within the active site of CYP1B1, where these compounds exerted their actions. These findings offer novel insights into investigating the potential antitumor properties of natural anthraquinones.

Exposure to oxygenated polycyclic aromatic hydrocarbons and endocrine dysfunction: Multi-level study based on hormone receptor responses.

Exposure to oxygenated polycyclic aromatic hydrocarbons and endocrine dysfunction: Multi-level study based on hormone receptor responses.

AElm-XGB: Hybrid Machine Learning Based Automated Classification of Oral Cancer by Effective Segmentation

Medical professionals benefit from early cancer disease detection because it shortens the time between diagnosis and treatment. In small towns and rural areas where people are less aware of the risks associated with tobacco and cigarette use, OC may have a high mortality rate due to its severe effects. The technique is insufficient for detecting OC disease in its early stages. Since people only live for five years on average after being diagnosed with OC disease, its detection may be possible at a later stage. By overcoming certain demerits of existing works, the proposed research work presents a novel machine learning (ML) based methodology for accurate diagnosis of oral cancer. At first, the input images are collected and pre-processed using the Quadruple Clipped Enhanced Histogram equalization (QCeHE) for enhancing the image contrast and Adaptive Prewitt and Laplacian of Gaussian filtering (ApLG) for noise removal. After the pre-processing step, hybrid segmentation is done on the basis of Expanded gate attention U-Net model (ExpG-UNet) method. Here the original images will be trained with that of generated ground truth images to obtain the segmented output. The features are extracted based on Integration of discrete wavelet transform, principle component analysis and gray level co-occurrence matrix (DWT-PCA-GLCM) method and extracted features are fused together. The features are provided to the machine learning method called Advanced Hybrid Extreme Learning Machine and Extreme Gradient Boosting (AElm-XGB) to classify the oral cancer effectively. The losses can be optimized by using African Vulture Optimization (AVO).The proposed model can accurately detect the oral cancer effectively. In the evaluation, the proposed model achieved 98.67 % accuracy. Diabetes mellitus, particularly type 2 diabetes, is a growing global health issue, often exacerbated by insulin resistance, metabolic disturbances, and inflammatory responses. Emodin, a natural anthraquinone derivative, has been widely recognized for its pharmacological properties, including its antidiabetic potential. This study investigates the therapeutic efficacy of emodin in ameliorating Type 2 diabetes in Wistar albino rats induced by streptozotocin (STZ). Male rats were divided into healthy, diabetic, and treatment groups, with diabetic groups receiving emodin (40 mg/kg body weight/day, orally) or metformin for 45 days. Diabetes induction was confirmed by elevated blood glucose levels, altered lipid profiles, and reduced insulin sensitivity. Emodin administration significantly reduced fasting blood glucose levels and improved glucose tolerance, comparable to metformin treatment. Biochemical analyses revealed that emodin restored the lipid profile, enhanced antioxidant enzyme activity, and suppressed oxidative stress markers in diabetic rats. The study revealed that emodin exhibited antidiabetic effects by regulating glucose metabolism, enhancing insulin sensitivity, and reducing oxidative stress. Data expressed as mean ± SEM showed significant differences (p<0.05) among control, diabetic control, emodin-treated, and metformin-treated groups. Emodin treatment notably improved glucose metabolism and outperformed metformin in reducing insulin resistance. These findings highlight emodin's potential as a therapeutic agent for Type 2 diabetes by targeting insulin resistance, inflammation, and metabolic dysregulation. Emodin holds promise for managing diabetes and its complications effectively.

Antidiabetic Potential of Emodin in Streptozotocin-Induced Type-2 Diabetic Rats

Diabetes mellitus, particularly type 2 diabetes, is a growing global health issue, often exacerbated by insulin resistance, metabolic disturbances, and inflammatory responses. Emodin, a natural anthraquinone derivative, has been widely recognized for its pharmacological properties, including its antidiabetic potential. This study investigates the therapeutic efficacy of emodin in ameliorating Type 2 diabetes in Wistar albino rats induced by streptozotocin (STZ). Male rats were divided into healthy, diabetic, and treatment groups, with diabetic groups receiving emodin (40 mg/kg body weight/day, orally) or metformin for 45 days. Diabetes induction was confirmed by elevated blood glucose levels, altered lipid profiles, and reduced insulin sensitivity. Emodin administration significantly reduced fasting blood glucose levels and improved glucose tolerance, comparable to metformin treatment. Biochemical analyses revealed that emodin restored the lipid profile, enhanced antioxidant enzyme activity, and suppressed oxidative stress markers in diabetic rats. The study revealed that emodin exhibited antidiabetic effects by regulating glucose metabolism, enhancing insulin sensitivity, and reducing oxidative stress. Data expressed as mean ± SEM showed significant differences (p<0.05) among control, diabetic control, emodin-treated, and metformin-treated groups. Emodin treatment notably improved glucose metabolism and outperformed metformin in reducing insulin resistance. These findings highlight emodin's potential as a therapeutic agent for Type 2 diabetes by targeting insulin resistance, inflammation, and metabolic dysregulation. Emodin holds promise for managing diabetes and its complications effectively.

Chemical profiling and characterisation of anthraquinone‐based polyphenols as biocolourants from Cortinarius semisanguineus

AbstractAnthraquinone dyes are known for their significant colour (brightness of shade in the red, blue and green areas) and light fastness properties compared with other synthetic dyes (such as azo‐based dyes). However, challenging multi‐step synthesis of anthraquinones and limited access to fewer substituents result in insufficient reactivity, hindering their wider industrial applications. Therefore, seeking highly substituted anthraquinone‐based colourants from natural sources is gaining interest among researchers. Notably, certain species of Dermocybe mushrooms are recognised for their red gills rich in anthraquinone colourants, which have been studied. However, limited knowledge of the chemotaxonomic characteristics of their species and molecular structure hinders wide use of their commercial applications. Our study screened extraction methods for their selectivity towards specific anthraquinone types, such as glycosidic vs non‐glycosidic, or those with carboxylic acid groups vs those without. In our observation, a sequential extraction strategy, starting with aqueous buffer extract followed by acetone extract, selectively yielded carboxylic acid‐containing anthraquinones and non‐carboxylic acid‐containing anthraquinones, respectively. We carried out a detailed analysis of anthraquinone‐based colourants in Cortinarius semisanguineus, comparing MS1‐MS2 profiles with two other species of the Dermocybe fungus group (Cortinarius sanguineus and Cortinarius ominosus), highlighting key interspecies differences in expressing certain anthraquinones or regioisomers. This study led to the structural identification of eleven natural anthraquinones and their glycosidic forms among these species. The carboxylic anthraquinones identified and characterised by their fragmentation pattern using MS1‐MS2 profiles include dermolutein, dermorubin, chlorodermorubin, endocrocin and chlorodermolutein, while the non‐carboxylic anthraquinones, primarily from the acetone extract, were dermoglaucin, emodin and dermocybin.

Characterizing phenotype variants of Cercosporidium personatum, causal agent of peanut late leaf spot disease, their morphology, genetics and metabolites

Cercosporidium personatum (CP) causes peanut late leaf spot (LLS) disease with 70% yield losses unless controlled by fungicides. CP grows slowly in culture, exhibiting variable phenotypes. To explain those variations, we analyzed the morphology, genomes, transcriptomes and chemical composition of three morphotypes, herein called RED, TAN, and BROWN. We characterized, for the first time in CP, anthraquinone (AQ) precursors of dothistromin (DOT), including averantin, averufin, norsolorinic acid, versicolorin B, versicolorin A, nidurufin and averufanin. BROWN had the highest AQ and melanin (15 mg/g DW) contents. RED had the highest ergosterol (855 µM FW) and chitin (beta-glucans, 4% DW) contents. RED and TAN had higher resistance to xenobiotics (p ≤ 1.0E-3), including chlorothalonil, tebuconazole and caffeine, compared to CP NRRL 64463. In RED, TAN, and BROWN, rates of single nucleotide polymorphisms (SNP) (1.4–1.7 nt/kb) and amino acid changes (3k-4k) were higher than in NRRL 64463. Differential gene expression (p ≤ 1.0E-5) was observed in 47 pathogenicity/virulence genes, 41 carbohydrate-active enzymes (CAZymes), and 23 pigment/mycotoxin biosynthesis genes. We describe the MAT1 locus, and a method to evaluate CP-xenobiotic resistance in 5 days. Chemical profiles indicate each CP morphotype could trigger different immune response in plants, probably hindering development of durable LLS resistance.

Kraft Pulp Yields and Paper Properties of Ten-year-old Clonal Acacia hybrid (Acacia mangium × Acacia auriculiformis) Wood

Clonal Acacia hybrid (Acacia mangium × Acacia auriculiformis) breeding in Indonesia aims to improve wood quality for the paper industry. This study investigated the effect of anthraquinone (AQ) addition on the quality of pulp and paper from ten-year-old clonal Acacia hybrid (015D) wood. Pulp making was carried out by kraft process with an active alkali concentration of 17%, sulfidity of 25%, and AQ concentrations of 0%, 0.05%, and 0.10% at a maximum temperature of 170oC for two hours of cooking time. AQ addition increased the yield to 54.70%, 58.23%, and 59.14% and decreased the kappa number to 24.06, 20.30, and 16.87, respectively. In terms of physical and optical properties, the paper had a burst index ranging from 3.31 to 3.66 kPa·m2/g, a tear index ranging from 1.72 to 2.40 mN·m2/g, a tensile index ranging from 49.41 to 50.28 Nm/g, opacity ranging from 87.38% to 88.44%, and brightness degrees ranging from 24.18 to 25.78. Burst and tensile indices met the Indonesian National Standard for broadleaf wood. AQ at 0.05% to 0.10% significantly reduced kappa numbers but did not significantly affect yield, mechanical, or optical properties. Therefore, an AQ concentration of 0.05% is recommended for clonal Acacia hybrid wood

The scavenging mechanism of hydrazone compounds towards HOO˙ and CH3OO˙ radicals: a computational mechanistic and kinetic study.

In this study, a detailed DFT investigation was conducted to systematically analyze the scavenging activity of six hydrazone compounds (1-6) against HOO˙ and CH3OO˙ radicals. Three mechanistic pathways were explored: hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SETPT), and sequential proton loss electron transfer (SPLET). These mechanisms were evaluated based on thermodynamic parameters, including bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE) in the gas phase, water, and pentyl ethanoate. HAT was identified as the most favorable mechanism in the gas phase, while SPLET was preferred in water. Among the studied compounds, compound 2 showed the highest rate constants for HOO˙ scavenging following the HAT mechanism in the gas phase observed at the O2'-H bond with a k Eck value of 6.02 × 104 M-1 s-1. For CH3OO˙ scavenging, the same compound exhibited the highest rate constants at the N8-H (9.03 × 104 M-1 s-1) and O2'-H (7.22 × 104 M-1 s-1) sites. The calculated overall rate constant values of compound 2 are k overall (HOO˙) = 6.86 × 104 M-1 s-1 and k overall (CH3OO˙) = 1.63 × 105 M-1 s-1. These results suggest that compound 2 exhibits antioxidant activities comparable to butylated hydroxyanisole (BHA), consistent with experimental findings, indicating its potential as an effective scavenger of hydroperoxyl and methoxy peroxyl radicals. In aqueous solution, the anionic form of compound 2 showed the greatest HOO˙ and CH3OO˙ radical scavenging activity among all of the studied compounds with rate constants of k app = 1.8 × 107 M-1 s-1 and k app = 3.3 × 106 M-1 s-1, respectively. Compared with some typical antioxidants such as rubiadin, natural fraxin, and natural anthraquinones, compound 2 showed higher HOO˙ and CH3OO˙ radical scavenging activity in water. Thus, compound 2 is a promising antioxidant in aqueous physiological environments.

Natural Anthraquinones as Potential Akt1-Targeted Anticancer Agents

Background: The phosphoinositide 3-kinase/protein kinase B (Akt)/mammalian target of the rapamycin signaling pathway is crucial in cancer progression. Akt1, a vital pathway component, has emerged as a promising therapeutic target. Objectives: This study used molecular docking analysis to investigate the potential of anthraquinones (AQs) as Akt1 inhibitors. Methods: The crystallographic structure of Akt1 was obtained from the Protein Data Bank (PDB ID: 4GV1). Twenty-one AQ compounds were selected for docking analyses using AutoDock 4.0. Binding affinities and interaction modes were compared with two Akt1 reference inhibitors. Results: Eleven AQs demonstrated substantial binding affinity to the Akt1’s catalytic site at nanomolar concentrations. Hypericin and sennidin B exhibited the most potent inhibitory effects, with ΔGbinding values of -11.19 kcal/mol and -10.36 kcal /mol, respectively, surpassing control inhibitors. Hypericin formed three hydrogen bonds and two hydrophobic interactions with the Akt1 catalytic cleft, while sennidin B formed six hydrogen and one hydrophobic interaction. Conclusion: This study identified several AQs, particularly hypericin and sennidin B, as promising Akt1 inhibitors with superior binding affinities compared to reference compounds. These findings provide a foundation for further developing AQ-based Akt1-targeted therapeutics in cancer treatment. Future research should focus on the in vitro and in vivo validation of these compounds’ efficacy and safety profiles.