Design, Synthesis, and Herbicidal Activity of Natural Naphthoquinone Derivatives Containing Diaryl Ether Structures.

Photosynthesis system II (PS II) is an important target for the development of bioherbicides. In this study, a series of natural naphthoquinone derivatives containing diaryl ether were designed and synthesized based on the binding model of lawsone and PS II D1. Bioassays exhibited that most compounds had more than 80% inhibition of Portulaca oleracea and Echinochloa crusgalli roots at a dose of 100 µg/mL and compounds B4, B5, and C3 exhibited superior herbicidal activities against dicotyledonous and monocotyledon weeds to commercial atrazine. In particular, compound B5 exhibited excellent herbicidal activity at a dosage of 150 g a.i./ha. In addition, compared with atrazine, compound B5 causes less damage to crops. Molecular docking studies revealed that compound B5 effectively interacted with Pisum sativum PS II D1 via diverse interaction models, such as π-π stacking and hydrogen bonds. Molecular dynamics simulation studies and chlorophyll fluorescence measurements revealed that compound B5 acted on PS II. This is the first report of natural naphthoquinone derivatives targeting PS II and compound B5 may be a candidate molecule for the development of new herbicides targeting PS II.

Lawsone Unleashed: A Comprehensive Review on Chemistry, Biosynthesis, and Therapeutic Potentials.

Lawsone, a naturally occurring organic compound also called hennotannic acid, obtained mainly from Lawsonia inermis (Henna). It is a potential drug-like molecule with unique chemical and biological characteristics. Traditionally, henna is used in hair and skin coloring and is also a medicinal herb for various diseases. It is also widely used as a starting material for the synthesis of various drug molecules. In this review, we investigate on the chemistry, biosynthesis, physical and biological properties of lawsone. The results showed that lawsone has potential antioxidant, anti-inflammatory, antimicrobial and antitumor properties. It also induces cell cycle inhibition and programmed cell death in cancer, making it a potential chemotherapeutic agent. Additionally, inhibition of pro-inflammatory cytokine production makes it an essential treatment for inflammatory diseases. Exploration of its biosynthetic pathway can pave the way for its development into targets for new drug development. In future, well-thought-out clinical studies should be made to verify its safety and efficacy.

Exploring the Therapeutic Potential of Lawsone and Nanoparticles in Cancer and Infectious Disease Management.

Lawsone, a naturally occurring compound found in henna, has been used in traditional medicine for centuries due to its diverse biological activities. In recent years, its nanoparticle-based structure has gained attention in cancer and infectious disease research. This review explores the therapeutic potential of lawsone and its nanoparticles in the context of cancer and infectious diseases. Lawsone exhibits promising anticancer properties by inducing apoptosis and inhibiting cell proliferation, while its nanoparticle formulations enhance targeted delivery and efficacy. Moreover, lawsone demonstrates significant antimicrobial effects against various pathogens. The unique physicochemical properties of lawsone nanoparticles enable efficient cellular uptake and targeted delivery. Potential applications in combination therapy and personalized medicine open new avenues for cancer and infectious disease treatment. While clinical trials are needed to validate their safety and efficacy, lawsone-based nanoparticles offer hope in addressing unmet medical needs and revolutionizing therapeutic approaches.

Functionalization of bamboo fibers with lawsone dye (Lawsonia inermis) to produce bioinspired hybrid color composite with antibacterial activity.

There is great interest in using eco-friendly functional colorants with antibacterial activity to produce colorful textile and plastic products. In this study, we designed, produced, and analyzed a novel multifunctional hybrid color composite colorant with antimicrobial properties, prepared from plant-based products. The new functional color composite was prepared by stabilizing lawsone dye onto amino-silanized cellulose from bamboo fibers. X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared (FTIR) spectroscopy were performed to examine the possible interactions between the lawsone dye and silanized bamboo fibers. The color performance, morphology, chemical stability, and thermal stability of the prepared color composite were evaluated using scanning electron microscopy (SEM), UV-Vis spectrophotometry, and thermogravimetric analysis (TGA). The results were compared to those for pure lawsone dye. Modification of amino-silanized bamboo fibers with lawsone dye led to the formation of a light brown colorant that is more resistant to organic solvents (e.g. acetone, ethanol) and elevated temperatures than raw natural dye. Importantly, the designed bamboo fiber/lawsone system (BF-APTES-L) benefits from the synergistic combination of lawsone and bamboo fibers, showing strong antibacterial activity compared to the control sample of bamboo-as evidenced by noticeably inhibited growth of E. coli, S. aureus, and B. subtilis.

Functionalization of cotton nonwoven with cyclodextrin/lawsone inclusion complex nanofibrous coating for antibacterial wound dressing.

Functionalizing cotton to induce biological activity is a viable approach for developing wound dressing. This study explores the development of cotton-based wound dressing through coating with biologically active nanofibers. Bioactive compounds like lawsone offer dual benefits of wound healing and infection prevention, however, their limited solubility and viability hinder their applications. To address this, Hydroxypropyl-beta-cyclodextrin (HP-ß-CD) and Hydroxypropyl-gamma-cyclodextrin (HP-γ-CD) were employed. Inclusion complexations of CD/lawsone were achieved at 2:1 and 4:1 M ratios, followed by the fabrication of CD/lawsone nanofibrous systems via electrospinning. Phase solubility studies indicated a twofold increase in lawsone water-solubility with HP-ß-CD. Electrospinning yielded smooth and uniform nanofibers with an average diameter of ∼300-700 nm. The results showed that while specific crystalline peaks of lawsone are apparent in the samples with a 2:1 M ratio, they disappeared in 4:1, indicating complete complexation. The nanofibers exhibited ∼100 % loading efficiency of lawsone and its rapid release upon dissolution. Notably, antibacterial assays demonstrated the complete elimination of Escherichia coli and Staphylococcus aureus colonies. The CD/lawsone nanofibers also showed suitable antioxidant activity ranging from 50 % to 70 %. This integrated approach effectively enhances lawsone's solubility through CD complexation and offers promise for bilayer cotton-based wound dressings.

Antibiofilm activity of lawsone against polymicrobial enterohemorrhagic Escherichia coli O157:H7 and Candida albicans by suppression of curli production and hyphal growth.

BACKGROUND: Most bacteria and fungi form biofilms that attach to living or abiotic surfaces. These biofilms diminish the efficacy of antimicrobial agents and contribute to chronic infections. Furthermore, multispecies biofilms composed of bacteria and fungi are often found at chronic infection sites. PURPOSE: In this study, lawsone (2­hydroxy-1,4-naphthoquinone) and its parent 1,4-naphthoquinone were studied for antimicrobial and antibiofilm activities against single-species and multispecies biofilms of enterohemorrhagic Escherichia coli O157:H7 (EHEC) and Candida albicans. METHODS: Biofilm formation assays, biofilm eradication assays, antimicrobial assays, live cell imaging microscopy, confocal laser scanning microscopy (CLSM), scanning electron microscopy (SEM), extracellular polymeric substances and indole production, cell surface hydrophilicity assay, cell motility, cell aggregation, hyphal growth, dual species biofilm formation, quantitative real-time reverse transcription polymerase chain reaction (qRT-PCR), and toxicity assays on plant seed germination and nematode model were utilized to investigate how lawsone affect biofilm development. RESULTS: Sub-inhibitory concentrations of lawsone (35 µg/ml) significantly inhibited single-and multispecies biofilm development. Lawsone reduced the production of curli and indole, and the swarming motility of EHEC, efficiently inhibited C. albicans cell aggregation and hyphal formation, and increased the cell surface hydrophilicity of C. albicans. Transcriptomic analysis showed that lawsone suppressed the expression of the curli-related genes csgA and csgB in EHEC, and the expression of several hypha- and biofilm-related genes (ALS3, ECE1, HWP1, and UME6) in C. albicans. In addition, lawsone up to 100 µg/ml was nontoxic to the nematode Caenorhabditis elegans and to the seed growth of Brassica rapa and Triticum aestivum. CONCLUSION: These results show that lawsone inhibits dual biofilm development and suggest that it might be useful for controlling bacterial or fungal infections and multispecies biofilms.

Synergistic activity of lawsone methyl ether in combination with some antibiotics and artocarpin against methicillin-resistant Staphylococcus aureus, Candida albicans, and Trychophyton rubrum / 中草药·英文版

Objective: One appealing strategy to overcome and prevent resistant problem is the use of combined two or more antibacterial substances. Lawsone methyl ether (LME) is the naphthoquinone found in the leaves of Impatiens balsamina. The objective of this study is to determine the interaction of LME with some antibiotics (ampicillin, tetracycline, norfloxacin, and clotrimazole) and a natural compound, artocarpin against methicillin-resistant Staphylococcus aureus (MRSA), Candida albicans, and Trychophyton rubrum. Methods: A broth microdilution method was used to determine the minimum inhibition concentration (MIC). Synergistic effects were evaluated at their own MIC using the checkerboard method and time-kill assay. Results: LME showed moderate antibacterial activity against MRSA with MIC value of 15.6 µg/mL, and exhibited strong antifungal activities against T. rubrum and C. albicans with MIC values of 7.8 and 3.9 µg/mL, respectively. The interaction of LME with the natural compound artocarpin against MRSA produced a synergy with fractional inhibitory concentration index (FICI) value of 0.31, while the combination of LME and clotrimazole exhibited synergy against C. albicans and T. rubrum with FICI values of 0.38 and 0.24, respectively. The time-kill assays confirmed that the compounds in combination enhanced their antimicrobial activities against the resistant microorganisms with different degrees. Conclusion: LME in combination with clotrimazole exhibited synergy effect against C. albicans and T. rubrum. In combination with artocarpin, it showed synergy effect against MRSA.

Saprolegnia parasitica Isolated from Rainbow Trout in Korea: Characterization, Anti-Saprolegnia Activity and Host Pathogen Interaction in Zebrafish Disease Model

Saprolegniasis is one of the most devastating oomycete diseases in freshwater fish which is caused by species in the genus Saprolegnia including Saprolegnia parasitica. In this study, we isolated the strain of S. parasitica from diseased rainbow trout in Korea. Morphological and molecular based identification confirmed that isolated oomycete belongs to the member of S. parasitica, supported by its typical features including cotton-like mycelium, zoospores and phylogenetic analysis with internal transcribed spacer region. Pathogenicity of isolated S. parasitica was developed in embryo, juvenile, and adult zebrafish as a disease model. Host-pathogen interaction in adult zebrafish was investigated at transcriptional level. Upon infection with S. parasitica, pathogen/antigen recognition and signaling (TLR2, TLR4b, TLR5b, NOD1, and major histocompatibility complex class I), pro/anti-inflammatory cytokines (interleukin [IL]-1β, tumor necrosis factor α, IL-6, IL-8, interferon γ, IL-12, and IL-10), matrix metalloproteinase (MMP9 and MMP13), cell surface molecules (CD8⁺ and CD4⁺) and antioxidant enzymes (superoxide dismutase, catalase) related genes were differentially modulated at 3- and 12-hr post infection. As an anti-Saprolegnia agent, plant based lawsone was applied to investigate on the susceptibility of S. parasitica showing the minimum inhibitory concentration and percentage inhibition of radial growth as 200 μg/mL and 31.8%, respectively. Moreover, natural lawsone changed the membrane permeability of S. parasitica mycelium and caused irreversible damage and disintegration to the cellular membranes of S. parasitica. Transcriptional responses of the genes of S. parasitica mycelium exposed to lawsone were altered, indicating that lawsone could be a potential anti-S. parasitica agent for controlling S. parasitica infection.

Naphthoquinones: biological properties and synthesis of lawsone and derivatives- a structured review / Naftoquinonas: propiedades biológicas y síntesis de lawsona y derivados ­ una revisión estructurada

Background: Naphthoquinones are natural pigments that are widely distributed in nature and have important biological activities. Lawsone (2-hydroxy-1,4-naphthoquinone) and its synthetic derivatives, and especially those containing nitrogen, have promising potential for the treatment of different diseases due to their antibacterial, antifungal, antiviral, antitumor and antiparasitic effects, and for pest control via their molluscicidal and insecticidal activities. Their pharmacological activities and mechanisms of action are related to their oxide/reduction and acid/base properties, and can be modulated by directly adding a substituted to the 1,4-naphthoquinone ring. Due to this, naphthoquinones and their derivatives are at the center of multiple areas of research. In this manuscript, we present a structured review of lawsone, a hydroxyl derivative of naphthoquinone, and discuss relevant reports about the chemistry and synthesis of derivatives. Finally, we present the pharmacological activities and mechanism of action reported. Objective: The purpose of this review is to present recent reports from the literature about the chemistry, synthesis and pharmacological properties of lawsone and its amine derivatives. Methods: This structured review presents a discussion about lawsone literature over the last ten years. The most representative studies including those about the chemistry of lawsone, the synthesis of its derivatives, and pharmacological properties were identified and selected. The information has been compiled, organized and presented into logical topics in order to provide a current review for the field of lawsone chemistry. Results: A general overview of the principal aspects of lawsone chemistry, the synthesis of its derivatives and their pharmacological activities and mechanism of action has been obtained. This provides researchers in the area with a framework from which to investigate further. Conclusions: Lawsone and its derivatives have promising potential for treating several diseases due to their antibacterial, antifungal, antiviral, antitumor and antiparasitic effects and have the potential to control pests via their molluscicidal and insecticidal properties. For this reason, it would be of interest to evaluate the synthetic derivatives of this compound for their pharmacologic actions; in the future, synthetic derivatives of lawsone could potentially be used to treat disease and be used as pesticides.

Molluscicidal activity of 2-hydroxy-[1, 4]naphthoquinone and derivatives

The toxic profile of lawsone (2-hydroxy-[1,4]naphthoquinone) and a series of [1,4]naphthoquinone derivatives was evaluated against the brine shrimp Artemia salina and against the mollusk Biomphalaria glabrata, the main transmitting vector of schistosomiasis in Brazil. Of the seventeen compounds tested nine fell below the threshold of 100 µg/mL set for potential molluscicidal activity by the World Health Organization. As a general rule derivatives with non-polar substituents presented the highest molluscicidal activities. These substances showed significant toxicity in A. salina lethality bioassay.

A toxicidade da lausona (2-hidroxi-1,4)-naftoquinona e de diversos derivados foi avaliada frente à Artemia salina e ao molusco Biomphalaria glabrata, o principal vetor de transmissão da esquistossomose no Brasil. Entre os dezessete compostos testados, nove apresentaram um perfil de toxicidade menor que 100 µg/mL, sendo potenciais agentes moluscicidas de acordo com as designações da Organização Mundial da Saúde. No presente estudo, os compostos contendo substituintes apolares exibiram as maiores atividades. Estes compostos também se mostraram significantemente tóxicos frente à A. salina.