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The present study aimed to investigate the influence of different growing conditions on the amount of leaf pigments (chlorophylls, carotenoids), bioactive metabolites, such as polyphenols, flavonoids, lawsone and volatile organic compounds (VOCs) of Lawsonia inermis L. (henna) plants. Young henna plants were cultivated for two months in a growth chamber (GC) and in open-air conditions during summer under the Mediterranean climate (OF), and leaves were analysed to evaluate their adaptive responses. The different growth conditions modified the carbon allocation priorities, increasing antioxidant metabolites (e.g. phenolic and flavonoid compounds) while decreasing lawsone in GC conditions. Quali-quantitative changes were observed for VOCs. This study revealed that GC conditions permit an alternative use of Lawsonia cultivation, because of the increase in the endogenous content of bioactive secondary metabolites with many potential biological activities. [ABSTRACT FROM AUTHOR]

Lawsone, an active phytoconstituent of Lawsonia inermis sp., is proposed as a safer alternative for the current skin anti-inflammatory treatments that are mainly steroidal with unwanted side effects which does not conform to the concept of halalan toyyiban in medicine. This study aims to investigate the inhibitory mechanism of lawsone on pro-inflammatory cytokine, TNF (tumour necrosis factor)-α through in silico and in vitro methods. The inhibitory mechanism of lawsone were investigated via molecular docking and molecular dynamics which were performed via AutoDock Vina and GROMACS softwares, respectively. The results were then analysed via PyMol, Proteins Plus, RMSD and RMSF graphs. Subsequently, cytotoxicity of lawsone towards A431 skin epidermoid and 3T3 fibroblast cells, was determined via MTT assay. Lawsone was further tested on A431 cells stimulated with ethanol (200 mM) or hydrogen peroxide (250 JM) for 24 hours (acute) and 48 hours (chronic) to induce pro-inflammatory cytokine (TNF-α) release. Cell viabilities were determined via MTT assay and expression of TNF-α were measured via ELISA. In silico works predicted lawsone's ability to bind to TNF-α with good binding affinity without disruption to the protein's structure stability. Lawsone is proven to be safe towards non-pathological cells. Lawsone exhibited significant anti-inflammatory effect on inflammation induced A431 epidermoid cells. ELISA results were not as expected as compared to previous in silico study, but an anti-inflammatory pattern can be observed in the chronic ethanol-induced treatment groups. In conclusion, lawsone is shown to have potential to be developed as a halalan-toyyiban alternative for skin anti-inflammatory treatment. [ABSTRACT FROM AUTHOR]

Aathira Sujathan Nair,1 Mahendran Sekar,1 Siew Hua Gan,1 Vinoth Kumarasamy,2 Vetriselvan Subramaniyan,3 Yuan Seng Wu,4 Nur Najihah Izzati Mat Rani,5 Subban Ravi,6 Ling Shing Wong7 1School of Pharmacy, Monash University Malaysia, Bandar Sunway, Subang Jaya, Selangor, 47500, Malaysia; 2Department of Parasitology & Medical Entomology, Faculty of Medicine, Universiti Kebangsaan Malaysia, Cheras, Kuala Lumpur, 56000, Malaysia; 3Department of Medical Sciences, School of Medical and Life Sciences, Sunway University, Bandar Sunway, Selangor, 47500, Malaysia; 4Sunway Microbiome Centre & Department of Biological Sciences, School of Medical and Life Sciences, Sunway University, Bandar Sunway, Selangor, 47500, Malaysia; 5Faculty of Pharmacy and Health Sciences, Royal College of Medicine Perak, Universiti Kuala Lumpur, Ipoh, Perak, 30450, Malaysia; 6Department of Chemistry, Karpagam Academy of Higher Education, Coimbatore, Tamil Nadu, India; 7Faculty of Health and Life Sciences, INTI International University, Nilai, 71800, MalaysiaCorrespondence: Mahendran Sekar, School of Pharmacy, Monash University Malaysia, Bandar Sunway, Subang Jaya, Selangor, 47500, Malaysia, Email mahendran.sekar@monash.edu Vinoth Kumarasamy, Department of Parasitology & Medical Entomology, Faculty of Medicine, Universiti Kebangsaan Malaysia, Jalan Yaacob Latif, Cheras, Kuala Lumpur, 56000, Malaysia, Email vinoth@ukm.edu.myAbstract: 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. Keywords: lawsone, Lawsonia inermis, henna, antitumor, antioxidant, anti-inflammatory, antimicrobial

A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2H benzo [f] indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4-hydroxy-7-methoxy-2-oxo-1,2 dihydroquinolin-3-yl) naphthalene-1,4-dione (7) and naphtha [2,3-b] furan-3,4,9 (2H)-trione (6) based on Lawsone 'that plays as important precursor' was synthesized by reaction with 1,3-diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2-chloro-acetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. [ABSTRACT FROM AUTHOR]

A simple, convenient, efficient and environmentally benign method has been developed for the synthesis of benzo[3,4-a]phenazin-5-ol as well as benzo[f]pyrido[2,3-b]quinoxalin-5-ol derivatives via the condensation of lawsoneand o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of trisodium citrate as an efficient, commercially available and low cost organo-catalyst in aqueous ethanol at room temperature. Mild reaction conditions, use of metal-free organocatalyst, nontoxic solvent, energy efficiency, no column chromatographic separation, gram scale production and reusability of the catalyst containing solvent media are some of the notable advantages of our developed protocol. [ABSTRACT FROM AUTHOR]

Lawsone, a naphthoquinone phytochemical compound present in the plants such as henna, was found to increase the healing process. However, clinical applications are impeded owing to the poor water solubility, low bioavailability, and dyeing property to the hair and skin. Nanostructured lipid carriers (NLCs) are appropriate carriers that cover undesirable effects of drugs, afford sustained release over a prolonged period of time, reduce systematic effects, decrease irritation, and increase tolerance. In this research, a formulation of lawsone incorporated NLC was prepared, and characterized for pharmaceutical application. The synthesized formulation was characterized using electron microscopy, polydispersity index, and zeta potential, and entrapment efficiency and malondialdehyde (MDA) level were evaluated. In order to assess wound healing potential, the wound area was measured at different times post-treatment, showing a structured tissue with better healing signs in NLC- Lw- Lv group in comparison with alpha ointment. NLC- Lw- Lv (NLC containing lawsone and lavender) formulation with mean size of 165.3 ± 4.2 nm, polydispersity index of 0.211, zeta potential of − 24.3 mV, and entrapment efficiency of 79.3 ± 2.9 was subjected to further experiments as optimized formulation. The ex vivo evaluation of formulation in mouse skin indicated better retention, less residue, and permeation in comparison with alpha ointment as standard. MDA level, as the indicator of lipid peroxidation, was lower in the NLC- Lw- Lv treated group. Histological score of microscopic wound healing parameters, such as swelling, re-epithelialization, formation of fibrotic tissue, and granulation, presented significantly better wound contraction in NLC- Lw- Lv treated group. In conclusion, our results propose the effective wound healing ability of lawsone, proved by more effective and an earlier stimulation of wound contraction. [ABSTRACT FROM AUTHOR]

Photosynthesis system Ⅱ (PS Ⅱ) inhibitors can block electron transport and disrupt plant photosynthesis and are used as herbicides. In order to develop new and effective PS II inhibitors, the lead structure lawsone was first found with remarkable herbicidal activity based on a virtual screening strategy, and its derivatives were designed and synthesized. The results of herbicidal activity evaluation showed that most of the compounds could achieve more than 80 % inhibitory effect on roots and stems of Portulaca oleracea at a dose of 100 μg/mL. Meanwhile, compound 4d showed more than 90 % inhibition on the stem of P. oleracea and on the root of Echinochloa crusgalli, which were superior to lawsone (64.9 and 67.6 %) and atrazine (63.6 and 65.9 %), respectively. Interestingly, 4d exhibited 100 % post-emergence herbicidal activity to Amaranthus retroflexus and Abutilon theophrasti at a dosage of 300 g a.i./ha, which was similar to atrazine but superior to lawsone. In addition, compound 4d can affect the efficiency of the photochemical process and strong bind PS II D1 protein. It revealed that compound 4d can be used as a promising PS II D1 inhibitor. This study provides a promising lead compound for developing new PS II inhibitors.

Background: A proficient hydroponic system for the cultivation of Rhinacanthus nasutus has been implemented with the aim of augmenting rhinacanthin production. Elicitation stands out as a viable technique for bolstering the yield of rhinacanthin. Materials and Methods: A hydroponics system of R. nasutus was treated with six elicitors, namely chitosan, Trichoderma harzianum extract, sodium alginate, lawsone, methyl jasmonate, and salicylic acid at three concentrations. A suitable elicitation period for the selected elicitor was also determined. The contents of rhinacanthin-C, -D, and -N accumulated were determined using an HPLC method. Results: Amongst these, chitosan (0.15 mg/mL) and T. harzianum extract (1.0 mg/mL) significantly enhanced rhinacanthin production and gave the highest total rhinacanthin content, up to 6.0-6.1% w/w, which was 2.2-fold higher than the untreated roots (2.7% w/w). In addition, lawsone (3.0 µM) and salicylic acid (100 µM) significantly increased rhinacanthin production up to 4.6% and 3.4% w/w, respectively, while neither methyl jasmonate nor sodium alginate increased rhinacanthin production. The suitable elicitor-contact periods for chitosan, T. harzianum extract, and lawsone were 48, 24, and 72 h, respectively. Moreover, the leaves harvested from these optimized conditions also contained markedly high contents of rhinacanthins, up to 5.4%, 6.7%, and 5.1% w/w, respectively. Conclusion: The present study established the optimized elicitation methods for the R. nasutus hydroponics system using chitosan, T. harzianum extract, and lawsone as elicitors to obtain the high-rhinacanthin-producing roots and leaves. These hydroponics and elicitation systems might be alternative sources of the high-quality R. nasutus roots and leaves. [ABSTRACT FROM AUTHOR]

Antifungal therapy is causing an alarming drug resistance problem during the treatment of Vaginal Candidiasis and also many of the antifungal vaginal marketed formulations have reported major side-effect of the irritation. Hence the quest for natural therapy is currently booming. Lawsone is having poor aqueous solubility and its antifungal activity is therefore hindered. Therefore, the present research work aimed to formulate the liquisolid compact based vaginal tablet of Lawsone to improve its solubility and dissolution rate. The tablet was optimized by 32 full factorial design. The independent factors selected were carrier (Neusilin US2): coating material (Aerosil 200) ratio (R) and concentration of the mucoadhesive polymer (HPMC K4M) while the dependent factors studied were in vitro release (6 h and 12 h) and mucoadhesive strength. The drug was dispersed in nonvolatile solvent (polyethylene glycol 400) to prepare the liquid medicament that was further used for liquisolid compact. The FTIR, DSC and XRD studies revealed no incompatibility between Lawsone and the excipients of the tablet and suggested that the drug was dispersed completely into the liquid medication and therefore transformed from crystalline to amorphous state. In vitro release study suggested sustained release with enhanced dissolution of optimized liquisolid compact tablet LT7 (94.92%) than the plain tablet (61.16%). The in vitro antifungal activity against C. albicans, C. glabrata and C. krusei for liquisolid tablet and the marketed tablet formulation showed insignificant difference. [ABSTRACT FROM AUTHOR]

Standard treatment for acute skin inflammatory conditions comes with unwanted side effects. Traditionally, Lawsonia inermis has been used to treat skin-related ailments, with lawsone as the main active phytochemical is predicted to inhibit a skin pro inflammatory cytokine, IL-1α. This study is aimed to evaluate the anti- inflammatory effect of lawsone in acute ethanol-induced skin inflammatory condition in vitro, by targeting IL-1α in silico. Basically, the IC50 of lawsone on human epidermoid carcinoma cell line (A431) was obtained by using MTT proliferation assay, followed by acute low dose ethanol-induced inflammatory skin condition on A431 cells to determine cell viability. Next, molecular docking study was done by utilizing Autodock Vina software, and further analyzed by ProteinsPlus and PyMol softwares. Meaningful interaction that exist in the binding of lawsone to IL-1α was determined by molecular docking results comparison with two other compounds (kirenol and curcumin diglucoside). In vitro study showed the IC50 of lawsone in low cytotoxicity level at 150 µM. Skin anti-inflammatory assay indicated that lawsone has highly significant (p

Background and purpose: Bacterial infections are treated with antibiotics, but the development of multi-drug resistant strains, which are growing at an increasing rate, is a phenomenon that threatens human societies. Therefore, alternative strategies are needed to combat infectious diseases. Today, compounds that reduce the pathogenicity of bacteria and do not interfere with their survival or growth are introduced as the next generation of antibiotics. Pseudomonas aeruginosa is one of the important and hazardous pathogens that employs its quorum-sensing network to regulate pathogenicity and virulence factors production. Here, we investigated the effect of a natural naphthoquinone compound, Lawsone (isolated from Henna), and its synthetic derivatives on the quorum-sensing system of P. aeruginosa PAO1. Materials and methods: First, the MIC of each compound was evaluated. Then, the effect of the selected compounds on biofilm formation and survival rate of biofilm sessile cells was investigated by colorimetric method. Finally, the virulence factors secretion of P. aeruginosa, including pyocyanin, pyoverdine, and protease was studied in the presence of the selected compounds. Results: The results indicated that Lawsone and NO2-481 reduced the production of P. aeruginosa biofilm by about 79% and 92%, respectively. Moreover, Lawsone and NO2-481 (at both concentrations, 250 and 125 µg/mL) decreased the viability of biofilm cells by about 70%. Furthermore, NO2-481 reduced the production of virulence factors including pyocyanin and pyoverdine by about 55% and 81%, respectively; however, it did not affect the protease production. Conclusion: NO2-481 derivative has the ability to reduce the pathogenicity of P. aeruginosa, and if it is proven to be non-cytotoxic, it can be assessed through animal and clinical studies, to be applied as an alternative compound along with antibiotics or disinfectants

In this survey, lawsone as natural bioactive compound encapsulate liposomal nanoparticle coated with chitosan–folate (L-LNPs-CF) has been developed as novel delivery system. The dynamic light scattering (DLS), zeta potential (ZP), field emission scanning electron microscope (FESEM) and Fourier transform infrared spectroscopy (FTIR) analysis were applied to assess the physiochemical characteristic. Furthermore, the potent antioxidant, anticancer and proapoptotic activities were uncovered by cell viability, acridine orange/propidium iodide (AO/PI) staining and flow cytometry. Meanwhile, the real-time PCR technique has been carried out to determine the gene profiling involved in cancer including caspase 3, 9 and Bax. The obtained results exhibited that L-LNPs-CF had 111.98 ± 2.15 nm in size with spherical structure and surface charge of 20.89 mV. The lawsone encapsulation efficiency was 83.8% in nanostructure. Apart from that, the cellular and molecular experiment revealed that L-LNPs-CF had strong free radical scavenging using DPPH and ABTS with respective values of 40.9%, 84.14% and significantly (p < 0.05) inhibited the cell proliferation of pancreatic cell (IC50: 171.94 µg/mL). Intriguingly, L-LNPs-CF notably up-regulated the caspase 3, 9 and bax genes as the key apoptotic genes. Outcome demonstrated that L-LNPs-CF enhances cellular uptake and could be an impressive therapeutic system for pancreatic cancer. [ABSTRACT FROM AUTHOR]

In this article, a Schiff base derivative has been prepared using 2‐hydroxy‐1,4‐naphthoquinone and 3‐amino‐1,2,4‐triazole, and consecutively, four metal complexes (Co(II), Ni(II), Cu(II) and Zn(II)) have been synthesized using this Schiff base derivative as precursor ligand. Characterization of the synthesized compounds are done by employing spectral techniques such as UV–vis, infrared (IR), nuclear magnetic resonance (NMR), mass and electron paramagnetic resonance (EPR). All these methods establish the existence of imine group and the octahedral geometry of the complexes. The synthesized complexes are evaluated for their DNA binding properties that confirm that the binding mode is intercalation. The bioactive ligand and its complexes also exhibit pronounced pharmacological activities such as antioxidant and antimicrobial activities against bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Salmonella typhi; fungi, namely, Aspergillus niger, Aspergillus flavus, Candida albicans and Rhizoctonia bataticola. Moreover, the compounds are examined for their density functional theory (DFT) studies using Gaussian 09 programme. Various reactivity descriptors are calculated based on the highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO‐LUMO) energies. Molecular docking is conducted with two different receptors 1BNA and 1HD2 proteins to get a wide knowledge on the in vitro biological examination and also the interaction of the compounds with different proteins. [ABSTRACT FROM AUTHOR]

A one-pot, two-step, four-component synthesis of novel benzo[a]phenazin-5-ol derivatives was carried out by the condensation-Michael addition reactions of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes, and 4-hydroxycoumarine in glacial acetic acid under reflux conditions. The notable features of this domino protocol are simple experimental procedure, readily available starting materials, metal-free reaction condition, clean reaction profile, good to high yields of the products, absence of any tedious workup and easy isolation of pure products without chromatography. [ABSTRACT FROM AUTHOR]

Background and purpose: Bacterial infections are treated with antibiotics, but the development of multi-drug resistant strains, which are growing at an increasing rate, is a phenomenon that threatens human societies. Therefore, alternative strategies are needed to combat infectious diseases. Today, compounds that reduce the pathogenicity of bacteria and do not interfere with their survival or growth are introduced as the next generation of antibiotics. Pseudomonas aeruginosa is one of the important and hazardous pathogens that employs its quorum-sensing network to regulate pathogenicity and virulence factors production. Here, we investigated the effect of a natural naphthoquinone compound, Lawsone (isolated from Henna), and its synthetic derivatives on the quorum-sensing system of P. aeruginosa PAO1. Materials and methods: First, the MIC of each compound was evaluated. Then, the effect of the selected compounds on biofilm formation and survival rate of biofilm sessile cells was investigated by colorimetric method. Finally, the virulence factors secretion of P. aeruginosa, including pyocyanin, pyoverdine, and protease was studied in the presence of the selected compounds. Results: The results indicated that Lawsone and NO2-481 reduced the production of P. aeruginosa biofilm by about 79% and 92%, respectively. Moreover, Lawsone and NO2-481 (at both concentrations, 250 and 125 µg/mL) decreased the viability of biofilm cells by about 70%. Furthermore, NO2-481 reduced the production of virulence factors including pyocyanin and pyoverdine by about 55% and 81%, respectively; however, it did not affect the protease production. Conclusion: NO2-481 derivative has the ability to reduce the pathogenicity of P. aeruginosa, and if it is proven to be non-cytotoxic, it can be assessed through animal and clinical studies, to be applied as an alternative compound along with antibiotics or disinfectants. [ABSTRACT FROM AUTHOR]

Abstract In pursuit of potential agents to treat Chagas disease and leishmaniasis, we report the design, synthesis, and identification novel naphthoquinone hydrazide-based molecular hybrids. The compounds were subjected to in vitro trypanocide and leishmanicidal activities. N’-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)-3,5-dimethoxybenzohydrazide (13) showed the best performance against Trypanosoma cruzi (IC50 1.83 µM) and Leishmania amazonensis (IC50 9.65 µM). 4-Bromo-N’-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzohydrazide (16) exhibited leishmanicidal activity (IC50 12.16 µM). Regarding trypanocide activity, compound 13 was low cytotoxic to LLC-MK2 cells (SI = 95.28). Furthermore, through molecular modeling studies, the cysteine proteases cruzain, rhodesain and CPB2.8 were identified as the potential biological targets.

Abstract Background Lung cancer is the deadliest type of cancer in the world and the search for compounds that can treat this disease is highly important. Lawsone (2-hydroxy-1,4-naphtoquinone) is a naphthoquinone found in plants from the Lawsone genus that show a high cytotoxic effect in cancer cell lines and its derivatives show an even higher cytotoxic effect. Methods Sulforhodamine B was used to evaluate the cytotoxic activity of compounds on tumor cells. Clonogenic assay was used to analyze the reduction of colonies and wound healing assay to the migratory capacity of A549 cells. Apoptosis and necrosis were analyzed by flow cytometer and Giemsa staining. Hemolysis assay to determine toxicity in human erythrocytes. Results Lawsone derivatives were evaluated and compound 1 (O-propargyllawsone) was the one with the highest cytotoxic effect, with IC50 below 2.5 µM in A549 cells. The compound was able to reduce colony formation and inhibit cell migration. Morphological changes and cytometry analysis show that the compound induces apoptosis and necrosis in A549 cells. Conclusions These results show that O-propargyllawsone show a cytotoxic effect and may induce apoptosis in A549 cells.

In this work, a two-step hydrothermal/solvothermal process was developed to generate highly fluorescent lawsone polymer dots (LPDs) utilizing an inexpensive and abundant starting material, 2-hydroxy-1,4-napththoquinone (lawsone). This hydrothermal/solvothermal process produces LPDs that have excitation independent emission with well-defined electronic transitions. This two-step protocol provides a straightforward approach to remove unwanted small molecular fluorescence, which has plagued carbon dot systems, without the need for advanced chromatographic purification methods or steps. A series of spectroscopic, electrochemical, and theoretical experiments suggest that this process proceeds via a sequential dehydration and dehydrogenation pathway to cross-link the lawsone into a carbon dot structure. This polymerization process helps to stabilize and favor certain electronic transitions inherently present in the lawsone monomer. The generation of the LPDs results in a 2 order of magnitude increase in the emission intensity and a quantum yield of 37%. This behavior is likely the result of the cross-linked structure shielding these electronic states from deactivation caused by nonradiative processes such as vibrational coupling and excited state quenching from thermal deactivation and solvent collisions. This finding is consistent with a cross-linked enhanced emission (CEE) mechanism, as previously observed for other similar systems. The LPDs were then incorporated into a TiO2 photoanode and utilized as a photosensitizer in a dye-sensitized solar cell (DSSC) which showed an enhancement in photocurrent density over pure TiO2. We also prepared a derivative of the LPDs utilizing a diethylene triamine additive (nitrogen-doped lawsone polymer dots (N-LPDs)) using the same two-step protocol and demonstrated its potential as a fluorescence microscopy dye for imaging MDA-MB-231 cancer cells. [ABSTRACT FROM AUTHOR]

The vanadium (IV) complex has been synthesized from naturally occurring lawsone and characterized by FT‐IR, UV‐Visible, ESI‐MS, powder XRD, and EPR spectroscopy. DFT calculation was performed for the optimization of complex geometry. The selective oxidation of diphenylmethane to benzophenone with tert‐butylhydrogenperoxide (TBHP) as an oxidant, was evaluated using the vanadium (IV) complex. The effect of several reaction parameters, such as temperature, catalyst quantity, and solvent type, was investigated. Under the optimal reaction conditions, diphenylmethane was transformed to benzophenone with a 96 % conversion with complete selectivity confirmed by GC‐MS. Further, the scope of the catalyst could be extended for the oxidation of other substrate having benzylic sp3 C−H bond. [ABSTRACT FROM AUTHOR]

A green and operationally simple approach for the library synthesis of novel bis-heteroarylaminomethylnaphthoquinone derivatives by a one-pot pseudo five-component domino condensation reaction of 5,5′-methylenebis(thiazol-2-amine), 2-hydroxy-1,4-naphthoquinone and various aromatic aldehydes in the presence of formic acid as the catalyst was developed. All reactions were performed in ethanol at room temperature and the products were isolated by simple filtration. The protocol proves to be an efficient and an environmentally benign in terms of good to high yields, readily available starting materials, easy workup, clean reaction profile, mild reaction conditions, green solvent and easy purification of products without chromatography. Some of the newly synthesized compounds were explored for their antimicrobial activities against two gram-positive and two gram-negative bacterial species. [ABSTRACT FROM AUTHOR]

Purpose: Targeted Graphene Oxide (GO) nanoparticles can play an important role in the treatment of cancer by increasing cancer cell targeting. This study was conducted to synthesize GO nanoparticles functionalized with chitosan-folate (CS-FA) to deliver a natural product Lawsone (LA) for cancer treatment. Methods: After characterization of the LA-GO-CS-FA, antioxidant activities of the nanoparticles were investigated by ABTS, DPPH, and FRAP tests. CAM assay was used to study the effect of nanoparticles on angiogenesis. The expression level of inflammatory and angiogenic genes in cells treated with nanoparticles was evaluated by real-time PCR. Results: The findings demonstrated the formation of nanoparticles with a size of 113.3 nm, a PDI of 0.31, and a surface charge of + 11.07 mV. The percentages of encapsulation efficiency were reported at 93%. Gastric cancer cells were reported as the most sensitive to treatment compared to the control, and the gastric cancer cells were used to study gene expression changes. The anti-angiogenic effects of nanoparticles were confirmed by reducing the average number and length of blood vessels and reducing the height and weight of embryos in the CAM assay. The reducing the expression of genes involved in angiogenesis in real-time PCR was demonstrated. Nanoparticles displayed high antioxidant properties by inhibiting DPPH and ABTS radicals and reducing iron ions in the FRAP method. The reduction of pro-inflammatory genes in AGS cells which were treated with nanoparticles indicates the anti-inflammatory properties of nanoparticles. Conclusion: This study showed the efficacy of nanoparticles in inhibiting gastric cancer cells by relying on inhibiting angiogenesis. [ABSTRACT FROM AUTHOR]

Diabetes is one of the major health issues globally. Type 1 diabetes mellitus develops due to the destruction of pancreatic β cells. Mesenchymal stem cells (MSCs) having remarkable self‐renewal and differentiation potential, can regenerate β cells. MSCs preconditioned with bioactive small molecules possess enhanced biological features and therapeutic potential under in vivo environment. Interestingly, compounds of naphthoquinone class possess antidiabetic and anti‐inflammatory properties, and can be explored as potential candidates for preconditioning MSCs. This study analyzed the effect of lawsone‐preconditioned human umbilical cord MSCs (hUMSCs) on the regeneration of β cells in the streptozotocin (STZ)‐induced Type 1 diabetes (T1D) rats. hUMSCs were isolated and characterized for the presence of surface markers. MSCs were preconditioned with optimized concentration of lawsone. T1D rat model was established by injecting 50 mg/kg of STZ intraperitoneally. Untreated and lawsone‐preconditioned hUMSCs were transplanted into the diabetic rats via tail vein. Fasting blood sugar and body weight were monitored regularly for 4 weeks. Pancreas was harvested and β cell regeneration was evaluated by hematoxylin and eosin staining, and gene expression analysis. Immunohistochemistry was also done to assess the insulin expression. Lawsone‐preconditioned hUMSCs showed better anti‐hyperglycemic effect in comparison with untreated hUMSCs. Histological analysis presented the regeneration of islets of Langerhans with upregulated expression of βcell genes and reduced expression of inflammatory markers. Immunohistochemistry revealed strong insulin expression in the preconditioned hUMSCs compared with the untreated hUMSCs. It is concluded from the present study that lawsone‐preconditioned hMSCs were able to exhibit pronounced anti‐hyperglycemic effect in vivo compared with hUMSCs alone. Significance statement: The study reports the therapeutic role of lawsone‐preconditioned mesenchymal stem cells (MSCs) for the treatment of streptozotocin‐induced Type 1 diabetes in rats. The preconditioned MSCs exhibited tremendous potential to regenerate β cells, increased insulin expression, and decreased inflammatory mediators. Altogether, this study offers a promising cell‐based therapeutic approach for the treatment of Type 1 diabetes mellitus in future. [ABSTRACT FROM AUTHOR]

Background: Our previous research highlighted remarkable hypoglycemic and hypolipidemic potentials of lawsone methyl ether (LME or 2-methoxy-1,4-naphthoquinone) and lawsone (2-hydroxy-1,4-naphthoquinone) in diabetic rats via β-cell regeneration. This insighted us to explore their additional antidiabetic mechanisms against α-glucosidase using in silico and in vitro approaches. Materials and Methods: In silico molecular docking was performed via Autodock Vina, SwissADME, and Datawarrior software. However, an in vitro inhibitory assay was conducted against α-glucosidase. Results: In silico studies revealed promising binding conformations and interactions of LME and lawsone with the functional residues of the α-glucosidase protein, involving hydrogen bonding, Van der Waals, and pi-pi interactions, showing comparable binding energies of -5.4 and -5.6 kcal/mol, respectively. Additionally, LME and lawsone displayed favorable pharmacokinetic profiles, revealing no evident toxicity. In vitro α-glucosidase inhibitory assay indicated that LME (IC50 of 37.4 µg/mL) and lawsone (IC50 of 42.2 µg/mL) exhibited comparable inhibitory activities, while both of them possessed markedly higher activities than acarbose (IC50 of 440.6 µg/mL). Furthermore, study on synergistic effects among these naphthoquinones and acarbose illustrated that at ½IC50 of LME (18.7 µg/mL) and acarbose (220.3 µg/mL) exhibited a satisfactory synergistic effect against α-glucosidase, with a percentage inhibition of 88.7% and a fractional percentage inhibition index (FPI) of 2.0, while at ½IC50 of lawsone (21.1 µg/mL) and acarbose (220.3 µg/mL) produced an additive effect, with a percentage inhibition of 76.4% and a FPI of 1.7. Conclusion: Promising α-glucosidase inhibitory potentials of LME and lawsone underscore their additional mechanism alongside β-cell regeneration further supporting their outstanding antidiabetic capabilities. [ABSTRACT FROM AUTHOR]

Background: Lung cancer is the deadliest type of cancer in the world and the search for compounds that can treat this disease is highly important. Lawsone (2-hydroxy-1,4-naphtoquinone) is a naphthoquinone found in plants from the Lawsone genus that show a high cytotoxic effect in cancer cell lines and its derivatives show an even higher cytotoxic effect. Methods: Sulforhodamine B was used to evaluate the cytotoxic activity of compounds on tumor cells. Clonogenic assay was used to analyze the reduction of colonies and wound healing assay to the migratory capacity of A549 cells. Apoptosis and necrosis were analyzed by flow cytometer and Giemsa staining. Hemolysis assay to determine toxicity in human erythrocytes. Results: Lawsone derivatives were evaluated and compound 1 (O-propargyllawsone) was the one with the highest cytotoxic effect, with IC50 below 2.5 µM in A549 cells. The compound was able to reduce colony formation and inhibit cell migration. Morphological changes and cytometry analysis show that the compound induces apoptosis and necrosis in A549 cells. Conclusions: These results show that O-propargyllawsone show a cytotoxic effect and may induce apoptosis in A549 cells. [ABSTRACT FROM AUTHOR]

Theoretical studies have been carried out using DFT, ab initio MP2 and Monte Carlo (MC) simulations of corrosion inhibitors from lawsone derivatives against carbon steel. The research focuses on studying the effect of substituent groups in the lawsone structure on the efficiency of corrosion inhibition in mild steel. Quantum chemical parameters of lawstone inhibitors in neutral and protonated conditions have been calculated. Fukui's function analysis predicts that the active side of the inhibitor will be adsorbed on the mild steel surface. MC simulation is used to understand the adsorption patterns of lawsone compounds on metal surfaces. The organic inhibitor L-NH2 has better performance as a corrosion inhibitor for mild steel in neutral or protonated conditions. [ABSTRACT FROM AUTHOR]

Due to the antimicrobial capabilities of henna leaf extract (Lawsonia inermis L.), this study intends to identify environmentally friendly ideal conditions for extracting bioactive compounds from henna leaf powder. For this purpose, the maceration method with a 100% aqueous solvent was selected for further analysis. Optimization of the extraction method was carried out by central composite design (CCD) protocol as a subset of Response Surface Methodology (RSM). The temperature of 40–90 °C, extraction time of 2–24 h, and the solvent-plant weight ratio ranging from 10 to 100 mL/mg were all considered independent variables. Also, the amount of lawsone, as an active component, and the total phenolic content were tracked as responses. Finally, a yield of 30.59% was achieved under the best extraction condition at 40 °C, 2 h, and a solvent-plant weight ratio of 1:100. The biological activity of an aqueous extract was evaluated using an HPLC-based activity profiling and TLC bioautography method. Peaks collected as fractions between 3 and 30 min were tested for antibacterial activity against Staphylococcus aureus ATCC 25923, and micro fractions from 5, 6, 7.5, 9, 10.5, 12, 13.5, 15, 19, and 30 min exhibited significant inhibitory effects. All spotted fractions on the TLC plate inhibited the growth of Escherichia coli ATCC 25922, except for micro fractions from 3, 18, and 21 min. Moreover, molecular docking analysis of quinones in the extract identified 3a, 4a-Dihydroxy-a-tetralone (C-2) as the most potent compound in interacting with bacteria sterol 14-demethylase protein, with docking scores of − 6.715 and − 7.196 kcal/mol, respectively. [Display omitted] • Effect of different variables on Lawson's extraction from henna was studied using RSM. • The biological activity of the extract is assessed using the HPLC-based profiling method. • The antimicrobial activity of micro fractions was also investigated. • The molecular docking study was employed to determine the potent compounds. [ABSTRACT FROM AUTHOR]

Our previous study uncovered potent inhibitory effects of two naphthoquinones from Impatiens balsamina, namely lawsone methyl ether (2-methoxy-1,4-naphthoquinone, LME) and lawsone (2-hydroxy-1,4-naphthoquinone), against α-glucosidase. This gave us the insight to compare the hypoglycemic and hypolipidemic effects of LME and lawsone in high-fat/high-fructose-diet- and nicotinamide-streptozotocin-induced diabetic rats for 28 days. LME and lawsone at the doses of 15, 30, and 45 mg/kg, respectively, produced a substantial and dose-dependent reduction in the levels of fasting blood glucose (FBG), HbA1c, and food/water intake while boosting the insulin levels and body weights of diabetic rats. Additionally, the levels of total cholesterol (TC), triglycerides (TGs), high-density lipoproteins (HDLs), low-density lipoproteins (LDLs), aspartate transaminase (AST), alanine transaminase (ALT), creatinine, and blood urea nitrogen (BUN) in diabetic rats were significantly normalized by LME and lawsone, without affecting the normal rats. LME at a dose of 45 mg/kg exhibited the most potent antihyperglycemic and antihyperlipidemic effects, which were significantly comparable to glibenclamide but higher than those of lawsone. Furthermore, the toxicity evaluation indicated that both naphthoquinones were entirely safe for use in rodent models at doses ≤ 50 mg/kg. Therefore, the remarkable antihyperglycemic and antihyperlipidemic potentials of LME make it a promising option for future drug development. [ABSTRACT FROM AUTHOR]

Naphthoquinones are a valuable source of secondary metabolites that are well known for their dye properties since ancient times. A wide range of biological activities have been described highlighting their cytotoxic activity, gaining the attention of researchers in recent years. In addition, it is also worth mentioning that many anticancer drugs possess a naphthoquinone backbone in their structure. Considering this background, the work described herein reports the evaluation of the cytotoxicity of different acyl and alkyl derivatives from juglone and lawsone that showed the best activity results from a etiolated wheat coleoptile bioassay. This bioassay is rapid, highly sensitive to a wide spectrum of activities, and is a powerful tool for detecting biologically active natural products. A preliminary cell viability bioassay was performed on cervix carcinoma (HeLa) cells for 24 h. The most promising compounds were further tested for apoptosis on different tumoral (IGROV-1 and SK-MEL-28) and non-tumoral (HEK-293) cell lines by flow cytometry. Results reveal that derivatives from lawsone (particularly derivative 4) were more cytotoxic on tumoral than in non-tumoral cells, showing similar results to those obtained with of etoposide, which is used as a positive control for apoptotic cell death. These findings encourage further studies on the development of new anticancer drugs for more directed therapies and reduced side effects with naphthoquinone skeleton. [ABSTRACT FROM AUTHOR]

"Herbal electronics" is a very new term tossed for the area where optical and electrical properties of herbal materials are being studied for possible application in electronics. The optical properties of extract solutions obtained from two raw materials namely turmeric, and henna has been studied here using absorption and luminescence spectroscopies. The as‐prepared solutions appear luminescent under UV light and generate two complementary colors, red and green which when mixed together exhibits yellow emission. A careful analysis has been carried out to understand how the two solutions can be mixed to obtain a yellow emission by using a simple Blue/UV LED as excitation source. Obtained emission colors has been qualified using CIE color chart and PL quantum yield have also been calculated. The yellow emission has been demonstrated using a simple set up where a blue led (400 nm) is used as excitation and the mixture solution is used as active luminescent material which emits yellow light with a quantum yield of ∼5 %. [ABSTRACT FROM AUTHOR]

We discuss here the preparation, characterization and antimicrobial properties of polyvinyl alcohol (PVA) based polymer films containing medicinally important plant extracts of Lawsonia inermis (henna) and Tamarindus indica (tamarind). The polymer films are prepared using a simple solution casting technique with concomitant heating at 42 °C. The ultraviolet-visible absorption spectrum and Fourier transform infrared spectroscopy (FTIR) of plant extracts confirm the presence of bioactive compounds, such as, 2-hydroxy, 1,4-naphthoquinone (lawsone) in henna extract and tannins, tartaric acid and reducing sugars in tamarind extract, respectively. FTIR analysis of the films confirms the presence of hydrogen bonding between PVA and tamarind phytochemicals in PVA-tamarind films. The surface topography and the average surface roughness analysis using an atomic force microscopy show that tamarind based polymer films have a lower surface roughness, due to a better interaction between PVA and tamarind phytochemicals, than that in henna based polymer films. Phase contrast microscopy images confirm the absence of polymer aggregation or pull-out in PVA-tamarind films, whereas, phase contrast microscopy images confirming the presence of such aggregation in PVA-henna films. Further, the thermal stability of the polymer films containing plant extract is studied in the temperature range of 30-250 °C. The antimicrobial activity of the films was studied using Kirby-Bauer Disc Diffusion method and the polymer films containing tamarind extract are found to exhibit antimicrobial activity against both E. coli and S. aureus. Quantitative analysis of the antimicrobial property of polymer films containing tamarind extract was carried-out using turbidimetry which further corroborates the antimicrobial property of these films. Thus, PVA-tamarind based films are promising candidates for antimicrobial applications, such as, in wound dressing as a ready to use bandage. [ABSTRACT FROM AUTHOR]

A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2H-benzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3-diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2-chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here. [ABSTRACT FROM AUTHOR]

The treatment of textile industrial wastewater is an important concern owing to its negative impact on the biosphere. The present study highlighted dye decolorization potential of bacterial consortium EDPA containing Enterobacter dissolvens AGYP1 and Pseudomonas aeruginosa AGYP2 in the presence of redox mediators. Rapid decolorization of Acid Maroon V (100 mg l−1) was achieved in the presence of lawsone compared to other redox mediators. The dye decolorization was best fitted with first order kinetics with higher reaction kinetics (k1 = 0.328 h−1) and regression coefficient (R2 = 0.979). The removal of dye by the consortium was 1.47 times faster in 8 h with 0.01 mM lawsone. The consortium EDPA was able to decolorize 1200 mg l−1 concentration of dye with apparent Rmax, Km and Rmax/Km values 1000 mg l−1 h−1, 5000 mg l−1 and 0.2 h−1, respectively. The lawsone-mediated system could decolorize the dye 80.44% in 10 h at the end of 11 dye spiking cycle. The superior biodecolorization of 14 different textile dyes was obtained in the presence of lawsone-mediated system. The intracellular enzyme activities of azoreductase, NADH-DCIP reductase, laccase, manganese peroxidase and lignin peroxidase increased significantly. The sequential microaerophilic-aerobic incubation resulted into 89.31% reduction of total aromatic amines. The microbial toxicity, phytotoxicity and genotoxicity measurements revealed biotransformation of toxic nature of dye Acid Maroon V into non-toxic metabolites by the action of consortium EDPA, and thus its suitability for biotreatment of dye containing industrial effluents. [ABSTRACT FROM AUTHOR]

Oral squamous cell carcinoma (OSCC) is a worldwide public health problem, accounting for approximately 90% of all oral cancers, and is the eighth most common cancer in men. Cisplatin and carboplatin are the main chemotherapy drugs used in the clinic. However, in addition to their serious side effects, such as damage to the nervous system and kidneys, there is also drug resistance. Thus, the development of new drugs becomes of great importance. Naphthoquinones have been described with antitumor activity. Some of them are found in nature, but semi synthesis has been used as strategy to find new chemical entities for the treatment of cancer. In the present study, we promote a multiple component reaction (MCR) among lawsone, arylaldehydes, and benzylamine to produce sixteen chemoselectively derivated Mannich adducts of 1,4-naphthoquinones in good yield (up to 97%). The antitumor activities and molecular mechanisms of action of these compounds were investigated in OSCC models and the compound 6a induced cytotoxicity in three different tumor cell lines (OSCC4, OSCC9, and OSCC25) and was more selective (IS > 2) for tumor cells than the chemotropic drug carboplatin and the controls lapachol and shikonin, which are chemically similar compounds with cytotoxic effects. The 6a selectively and significantly reduced the amount of cell colony growth, was not hemolytic, and tolerable in mice with no serious side effects at a concentration of 100 mg/kg with a LD50 of 150 mg/kg. The new compound is biologically stable with a profile similar to carboplatin. Morphologically, 6a does not induce cell retraction or membrane blebs, but it does induce intense vesicle formation and late emergence of membrane bubbles. Exploring the mechanism of cell death induction, compound 6a does not induce ROS formation, and cell viability was not affected by inhibitors of apoptosis (ZVAD) and necroptosis (necrostatin 1). Autophagy followed by a late apoptosis process appears to be the death-inducing pathway of 6a, as observed by increased viability by the autophagy inhibitor (3-MA) and by the appearance of autophagosomes, later triggering a process of late apoptosis with the presence of caspase 3/7 and DNA fragmentation. Molecular modeling suggests the ability of the compound to bind to topoisomerase I and II and with greater affinity to hPKM2 enzyme than controls, which could explain the mechanism of cell death by autophagy. Finally, the in-silico prediction of drug-relevant properties showed that compound 6a has a good pharmacokinetic profile when compared to carboplatin and doxorubicin. Among the sixteen naphthoquinones tested, compound 6a was the most effective and is highly selective and well tolerated in animals. The induction of cell death in OSCC through autophagy followed by late apoptosis possibly via inhibition of the PKM2 enzyme points to a promising potential of 6a as a new preclinical anticancer candidate. [ABSTRACT FROM AUTHOR]

[Display omitted] Photosynthesis system Ⅱ (PS Ⅱ) inhibitors can block electron transport and disrupt plant photosynthesis and are used as herbicides. In order to develop new and effective PS II inhibitors, the lead structure lawsone was first found with remarkable herbicidal activity based on a virtual screening strategy, and its derivatives were designed and synthesized. The results of herbicidal activity evaluation showed that most of the compounds could achieve more than 80 % inhibitory effect on roots and stems of Portulaca oleracea at a dose of 100 μg/mL. Meanwhile, compound 4d showed more than 90 % inhibition on the stem of P. oleracea and on the root of Echinochloa crusgalli, which were superior to lawsone (64.9 and 67.6 %) and atrazine (63.6 and 65.9 %), respectively. Interestingly, 4d exhibited 100 % post-emergence herbicidal activity to Amaranthus retroflexus and Abutilon theophrasti at a dosage of 300 g a.i./ha, which was similar to atrazine but superior to lawsone. In addition, compound 4d can affect the efficiency of the photochemical process and strong bind PS II D1 protein. It revealed that compound 4d can be used as a promising PS II D1 inhibitor. This study provides a promising lead compound for developing new PS II inhibitors. [ABSTRACT FROM AUTHOR]

In this reported work, an anodically pretreated boron-doped diamond (BDD) electrode was used for the inexpensive, simple and quick detection of a natural dye, lawsone. Lawsone had a well-defined, irreversible and diffusion-controlled oxidation peak at approximately +0.19 V in phosphate buffer solution (PBS, 0.1 M, pH 2.5) using cyclic voltammetry (CV). The oxidation peak heights of lawsone were significantly increased in PBS using the cationic surfactant cetyltrimethylammonium bromide (CTAB). Under optimized experimental conditions, the calibration curve was linear over a concentration range of 0.1–5.0 μM with detection limit of 0.029 μM in 0.1 M PBS (pH 2.5) containing 0.1 mM CTAB by using square-wave voltammetry (SWV). To evaluate the practical applicability of the BDD electrode, it was used for the quantification of lawsone in commercial henna, a natural dye made from the leaves of the henna plant.

The fast development of multi-drug resistant (MDR) organisms increasingly threatens global health and well-being. Plant natural products have been known for centuries as alternative medicines that can possess pharmacological characteristics, including antimicrobial activities. The antimicrobial activities of essential oil (Calli oil) extracted from the Calligonum comosum plant by hydro-steam distillation was tested either alone or when combined with lawsone, a henna plant naphthoquinone, against MDR microbes. Lawsone showed significant antimicrobial activities against MDR pathogens in the range of 200-300 µg/mL. Furthermore, Calli oil showed significant antimicrobial activities against MDR bacteria in the range of 180-200 µg/mL, Candida at 220-240 µg/mL and spore-forming Rhizopus fungus at 250 µg/mL. Calli oil's inhibition effect on Rhizopus, the major cause of the lethal infection mucormycosis, stands for 72 h, followed by an extended irreversible white sporulation effect. The combination of Calli oil with lawsone enhanced the antimicrobial activities of each individual alone by at least three-fold, while incorporation of both natural products in a liposome reduced their toxicity by four- to eight-fold, while maintaining the augmented efficacy of the combination treatment. We map the antimicrobial activity of Calli oil to its major component, a benzaldehyde derivative. The findings from this study demonstrate that formulations containing essential oils have the potential in the future to overcome antimicrobial resistance.

Efficient synthesis of dispiro[indoline-3,4'-pyrrolidine-3',2''-naphthalene]-1'',2,3'',4''-tetraone (3) and spiro[imidazole-4,2'-naphthalene]-1',3',4'-trione derivatives 4 that derived from lawsone moiety as high reactive building block are confirmed via 1,3-dipolar cycloaddition of azomethine ylides generate in situ from benzyl amine and isatin occurred at the double bond of arylidene of lawsone upon heating and or via addition α,β-unsaturated ketone 2 with oxidizing agent hydrogen peroxide (H2O2) (30%) and guanidine.HCl in one portion. [ABSTRACT FROM AUTHOR]

Researchers have renewed interest in naturally occurring compounds and their applications particularly in the pharmacological field with the goal of fewer side effects; lawsone is one among them. It is easily available and cost-efficient among the naphthoquinone family. Lawsone and its metal complexes are compounds with a wide variety of applications; especially it has promising biological activity. This review focuses on synthesis and applications, particularly in the biological field of a few transition metal complexes incorporating lawsone and its derivatives over the last two decades. [ABSTRACT FROM AUTHOR]

Our previous study uncovered potent inhibitory effects of two naphthoquinones from Impatiens balsamina, namely lawsone methyl ether (2-methoxy-1,4-naphthoquinone, LME) and lawsone (2-hydroxy-1,4-naphthoquinone), against α-glucosidase. This gave us the insight to compare the hypoglycemic and hypolipidemic effects of LME and lawsone in high-fat/high-fructose-diet- and nicotinamide-streptozotocin-induced diabetic rats for 28 days. LME and lawsone at the doses of 15, 30, and 45 mg/kg, respectively, produced a substantial and dose-dependent reduction in the levels of fasting blood glucose (FBG), HbA1c, and food/water intake while boosting the insulin levels and body weights of diabetic rats. Additionally, the levels of total cholesterol (TC), triglycerides (TGs), high-density lipoproteins (HDLs), low-density lipoproteins (LDLs), aspartate transaminase (AST), alanine transaminase (ALT), creatinine, and blood urea nitrogen (BUN) in diabetic rats were significantly normalized by LME and lawsone, without affecting the normal rats. LME at a dose of 45 mg/kg exhibited the most potent antihyperglycemic and antihyperlipidemic effects, which were significantly comparable to glibenclamide but higher than those of lawsone. Furthermore, the toxicity evaluation indicated that both naphthoquinones were entirely safe for use in rodent models at doses ≤ 50 mg/kg. Therefore, the remarkable antihyperglycemic and antihyperlipidemic potentials of LME make it a promising option for future drug development.

Lawsone is a biomolecule that belongs to the naphthoquinone class found in henna leaves. This quinone is widely used in cosmetic products being considered the oldest coloring agent applied for dyeing hair. Moreover, biological activities have been attributed to lawsone such as antibacterial, antifungal, and anticancer. However, these activities are mostly limited due to its low aqueous solubility and chemical instability. In this context, this study aimed to develop nanoemulsion containing lawsone (NE-law) and assess its in vitro cytotoxicity against cervical carcinoma cells. Emulsion phase inversion method was used to prepare nanoemulsion formulations (NE1, NE2, NE3, NE4, and NE-law). Following the formulation development, NE1 formulation was chosen to incorporate lawsone, presenting average droplet size about 45 nm with narrow size distribution (PdI < 0.1) and negative zeta potential (≈ − 13 mV). In TEM analyses, droplets were visualized with irregular spherical shapes, high homogeneity, and without aggregation. The incorporation efficiency of lawsone into NE was higher than 90%, and in vitro release profile of this naphthoquinone from formulation was gradual and regular throughout the experiment. Nanoemulsified lawsone improved in vitro cytotoxicity on cervical carcinoma cells compared to free lawsone. Therefore, we prepared a stable lawsone-loaded NE using a reproducible emulsification method. [ABSTRACT FROM AUTHOR]

Phenazine derivative compounds are of concern because of their extraordinary activities in medicine. The aim of this study is to synthesize the derivative of benzo[a]pyrano[2,3-c] phenazine compound based on lawsone with caffeine catalyst using the one-pot multicomponent reaction method and test its antioxidant activity. The formation of the target compound was evaluated for functional group vibration, maximum wavelength, and molecular weight by FTIR, UV-Vis Spectrophotometer, and LCMS, which showed the characteristics of the benzo[a]pyrano[2,3-c] phenazine compound. The synthesized compound was 3-amino-2-cyano-1-(2-hydroxyl-phenyl)-1H-benzo[a]pyrano[2,3-c] phenazine with the molecular formula C26H16N4O2. At the optimum condition of the reaction, the use of caffeine catalyst was able to give a product yield of 67.2%. The potential of the synthesized compound as an antioxidant could be classified as a good antioxidant with an IC50 value of 14.26 ppm. [ABSTRACT FROM AUTHOR]

Plant based therapeutics have been extensively used for wound healing due to their faster healing rate and lesser side effects. The combinatorial approach of traditional concept with modern hydrogel-based drug delivery system can able to heal the wound in an accelerated manner. The present study aimed to formulate and evaluate the wound healing potential of hydrogel containing standardized ethanolic extract of Lawsonia inermis Linn. Ethanolic extract of leaves was prepared, standardized with respect to lawsone by validated high-performance thin-layer chromatographic method. The hydrogel formulations were prepared using Carbopol 934 in different concentrations (0.5, 1.0 and 2.0 % w/w), assessed for cosmetic persona, pH, viscosity, spreadability, occlusion, syneresis, drug content, drug-excipient compatibility, skin irritation and for its wound healing activity. The hydrogel formulations (F1, F2 and F3) were found to be clear, homogeneous, compatible, nonirritant in nature, with pH (6.73±0.047 to 6.8±0.082), spreadability (6.81±0.09 to 8.13±0.08 cm), viscosities (39840±500.07 to 87538±389.87 cp), occlusion factor values (57.43±1.24 to 73.82±2.48 %), percent syneresis (2.696±0.368 to 5.5±0.226), and percent drug content (94.271±0.292 to 96.587±0.402) were found to be optimal for topical application. Hydrogel (F2) exhibited a significant healing response in the excision wound rat model. Wound healing was significantly improved among the test groups on the 4th, 8th and 12th d (p<0.001) in comparison to standard lawsone hydrogel and control group. The result showed that the studied hydrogel has the potential for wound dressing. [ABSTRACT FROM AUTHOR]

Introduction: Lawsone is a phyto-constituent obtained from the leaves of the Lawsonia inermis. It has antibacterial, antifungal, antiviral, wound healing, antiparasitic, tuberculostatic, anti-fertility, analgesic, anti-inflammatory, enzyme inhibitory, nematicidal, anticoagulant, and protein glycation inhibitory activities. It has poor water solubility (hydrophobic), poor bioavailability, and poor dissolution characteristics. Aim: The purpose of this research is to improve the aqueous solubility of Lawsone by preparing the inclusion complexes of Lawsone with beta-cyclodextrin. Materials and Methods: Inclusion complexes of Lawsone were prepared by different methods such as physical mixture, kneading method and co-precipitation method. Characterization of the complexes were done by Fourier Transform Infrared (FTIR) spectroscopy and in vitro dissolution study. Differential scanning calorimetry (DSC), Nuclear Magnetic Resonance spectroscopy (NMR), and Powder X-Ray Diffraction (PXRD). were used to evaluate the co-precipitation technique inclusion complexes. Antimicrobial studies of complexes against Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Bacillus subtilis (B. subtilis), and Pseudomonas aeruginosa (P. aeruginosa ) were done by colony counting method. Results: Phase solubility study revealed the molar ratio of Lawsone to betacyclodextrin in the complex is 1:1. At the third hour, the drug release was 64%, 78%, 93%, and 97% for pure drug, physical mixture, inclusion complexes formed by kneading technique and co-precipitation technique respectively. DSC, NMR, and PXRD confirmed the formation of complexes of Lawsone. The order of antibacterial activity of inclusion complexes was E. coli > B. subtilis > P. aeruginosa > S. aureus. [ABSTRACT FROM AUTHOR]

A new series of bis‐heteroarylaminomethylnaphthoquinone Mannich bases have been synthesized through facial and efficient one‐pot pseudo five‐component reactions of lawsone, different heteroaryl amines and terephthaldehyde using p‐TSA as catalyst in CH3CN under reflux conditions. The high yields of products, very simple operation, readily available starting materials, high atom‐economy, easy workup procedure and isolation/purification of target products without chromatography are the main benefits of this synthetic strategy. [ABSTRACT FROM AUTHOR]

A stereoselective, base‐free Heck coupling between 1,4‐naphthoquinone and 1H‐1,2,3‐triazole derivatives was reported for the first time. This study shows that depending on the 1,4‐naphthoquinone, the use of an additional base is unnecessary to produce the naphthoquinone‐triazole conjugates. This is also the first example of a Heck coupling of these two cores without using a base as an additive. In this work, sixteen new naphthoquinone‐triazole hybrids were stereoselectively synthetized in good to excellent yields. The reaction mechanism was discussed based on DFT CAM−B3LYP calculations. The first step is the coordination of the arene to the palladium catalyst to form a palladacycle intermediate. After reorganization in this intermediate, the double bond in the arene is restored to proceed with the coupling step and formation of the C−C bond in the rate determining step. The Kozuchi‐Shaik span model was employed to rationalize substituent effects. [ABSTRACT FROM AUTHOR]

The solvent effect on the molecular properties of lawsone and purpurin molecules has been investigated using DFT and TD-DFT. The calculations have been performed using CAM-B3LYP functional and 6-311++G(d,p) basis set. Molecular properties including solute energy, electronic spatial extent, HOMO–LUMO energy gap, thermodynamic properties, the free energy of solvation, electronic properties and UV–visible spectra have been studied. These properties have been analysed in 12 solvents, i.e. benzene, chloroform, aniline, dichloromethane, dichloroethane, benzyl alcohol, 3-pentanone, acetone, ethanol, methanol, acetonitrile and DMSO, and the variation of molecular properties has been studied as a function of the dielectric constant of solvents. We also studied the light-harvesting efficiency (LHE) and the lifetime of excitation of dye molecules in the presence of selected solvents to identify its use as a sensitizer in dye-sensitised solar cells. It has been found that purpurin molecule exhibits a higher LHE and lower excited state lifetime than lawsone molecule. We also observed that the LHE of lawsone molecule has a maximum value for aniline and benzyl alcohol solvents, whereas for purpurin molecule, aniline shows greater LHE values due to the auxochrome effect. [ABSTRACT FROM AUTHOR]