Protective effects of (1-(4-hydroxy-phenyl)-3-m-tolyl-propenone chalcone in indomethacin-induced gastric erosive damage in rats.

BACKGROUND: Non-steroidal anti-inflammatory drugs (NSAIDs) can result in peptic ulcer disease (PUD) which is a common condition worldwide. The aim of this study was to evaluate the antiulcer properties of (1-(4-hydroxy-phenyl)-3-m-tolyl-propenone) (HPTP) chalcone in rats using indomethacin as ulcerogenic agent. RESULTS: None of the rats showed symptoms of kidney and liver toxicity during the term of the study. Administration of HPTP had decreased the acidity, increased gastric wall mucus and flattening of gastric mucosa and reducing erosive gastric damage area. HPTP also showed dose dependent increase in SOD, GPx activity and PGE2 level and decrease MDA. H & E stain showed decreased infiltration of leucocytes with edema of submucosal layer. PAS staining showed intense uptake of magenta color of gastric wall mucus in rats fed with HPTP, and immunohistochemical staining of gastric mucosa revealed over-expression of HSP70 protein, down-expression of Bax protein and over expression of TGF-ß in rats administered with HPTP. CONCLUSION: This study has revealed that chalcone1-(4-hydroxy-phenyl)-3-m-tolyl-propenone can serve as a safe and effective antiulcer agent as it has been proved to increase pH and gastric wall mucus, increase GPx, SOD, PGE2, and decrease MDA level, ultimately, it has also contributes towards the over-expression of HSP protein andTGF-ß, and down-expression of Bax protein.

Effect of oral administration of ethanolic extract of Vitex negundo on thioacetamide-induced nephrotoxicity in rats.

BACKGROUND: Oxidative stress due to abnormal induction of reactive oxygen species (ROS) molecules is believed to be involved in the etiology of many diseases. Evidences suggest that ROS is involved in nephrotoxicity through frequent exposure to industrial toxic agents such as thioacetamide (TAA). The current investigation was designed to explore the possible protective effects of the leaves of Vitex negundo(VN) extract against TAA-induced nephrotoxicity in rats. METHODS: Twenty four Sprague Dawleyrats were divided into four groups: (A) Normal control, (B) TAA (0.03% w/v in drinking water), (C) VN100 (VN 100 mg/kg + TAA) and (D) VN300 (VN 300 mg/kg + TAA). Blood urea and serum creatinine levels were measured,supraoxide dismutase (SOD), catalase (CAT) and malondialdehyde (MDA) levels of renal tissue were assayed. Histopathological analysis together with the oxidative stress nicotinamide adenine dinucleotide phosphate (NADPH) oxidase p22phox in kidney sections were examined in all experimental groups. RESULTS: Blood urea and serum creatinine levels were increased in TAA group as a result of the nephrotoxicity compared to the VN100 and VN300 groups where, the levels were significantly decreased (p < 0.05). Renal MDA level was significantly decreased (p < 0.05) in the VN-treated groups with increased CAT and SOD activities compared to the TAA group. Light microscopic examination of renal tissues stained by H&E stain and Masson's Trichrome for TAA-treated groups revealed severe histopathological changes, whereas specimens obtained from VN-treated groups showed only mild changes. These findings were supported by immunohistochemical results. CONCLUSIONS: VN extract acts as a natural potent antioxidant to prevent ongoing TAA-induced nephrotoxicity in rats, both biochemically and morphologically.

PASS-predicted Vitex negundo activity: antioxidant and antiproliferative properties on human hepatoma cells--an in vitro study.

BACKGROUND: Hepatocellular carcinoma is a common type of tumour worldwide with a high mortality rate and with low response to current cytotoxic and chemotherapeutic drugs. The prediction of activity spectra for the substances (PASS) software, which predicted that more than 300 pharmacological effects, biological and biochemical mechanisms based on the structural formula of the substance was efficiently used in this study to reveal new multitalented actions for Vitex negundo (VN) constituents. METHODS: Experimental studies based on antioxidant and antiproliferative assays verified the predictions obtained by the PASS-predicted design strategy. Antioxidant activity of VN extract was studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Ferric reducing or antioxidant power (FRAP) assays. The antiproliferative activity of VN extract against WRL68 and HepG2 was investigated based on methylthiazol tetrazolium (MTT) spectrophotometric assay. RESULTS: VN extract showed 79.43% inhibition of DPPH stable radical with IC50 13.31 ± 0.18 µg/ml. This inhibition was too closed to butylated hydroxyl toluene (BHT) 82.53% (IC5013.8 ± 0.14) and gallic acid 89.51% (IC50 3.1 ± 0.08). VN extract exhibited the strongest free radical scavenging power compared with two commercial antioxidants, BHT and ascorbic acid. VN increased the activities of antioxidant enzymes in normal embryonic liver cells (WRL68) including, superoxide dismutase (SOD) and glutathione peroxidase (GPX) compared with to H2O2 group. The ethanolic extract of VN showed cytotoxicity to HepG2 cells in a dose and time-dependent manner with IC50 66.46 µg/ml, 57.36 µg/ml and 65.12 µg/ml at 24, 48, and 72-hours incubation respectively, with no sensitivity in WRL68 cells. This was associated with significant elevation in lactate dehydrogenase (LDH) release in HepG2 cells. In addition, the activation of caspase-3 enzyme suggesting that the observed cytotoxicity was mediated via an intrinsic apoptosis pathway. CONCLUSIONS: PASS-predicted plant activity could efficiently help in selecting a promising pharmaceutical leads with high accuracy and required antioxidant and antiproliferative properties. This is the first report on PASS-predicted VN activity.

Gene expression profiling reveals underlying molecular mechanism of hepatoprotective effect of Phyllanthus niruri on thioacetamide-induced hepatotoxicity in Sprague Dawley rats.

BACKGROUND: The liver plays an essential role in the body by regulating several important metabolic functions. Liver injury is associated with the distortion of these functions causing many health problems. Pharmaceutical drugs treat liver disorders but cause further damage to it. Hence, herbal drugs are used worldwide and are becoming increasingly popular. METHODS: The hepatoprotective activity of Phyllanthus niruri (PN) was evaluated against liver cirrhosis induced by thioacetamide (TAA) in male Sprague Dawley rats. Rats received intraperitoneal injections of thioacetamide (TAA, 200 mg/kg, b.w. three times weekly) for eight weeks. Daily treatments with plant extract (200 mg/kg) were administered orally for eight weeks. At the end of the study, hepatic damage was evaluated by monitoring transforming growth factor (TGFß), collagen α1 (Collα1), matrix metalloproteinase-2 (MMP2) and tissue inhibitor of matrix metalloproteinase-1 (TIMP1) gene expression by real-time PCR. Moreover, different chromatographic techniques including column chromatography, thin layer chromatography, and Ultra Performance Liquid Chromatography (UPLC) with Liquid Chromatography/Mass Spectrometry (LC/MS) were used to isolate the active constituents of the plant. RESULTS: The results revealed that treatment with PN significantly reduced the effect of thioacetamide toxicity and exhibited effective hepatoprotective activity. The mechanism of the hepatoprotective effect of PN is proposed to be by normalizing ROSs. Additionally, PN treatment regulated the expression of TGFß, Collα1, MMP2, and TIMP1 genes. In the active fraction of P. niruri, the isolated chemical constituents were 4-O-caffeoylquinic acid and quercetin 3-O-rhamnoside. CONCLUSIONS: The results of the present study indicate that PN ethanol extracts possess hepatoprotective activity that is most likely because of the isolated chemical constituents.

Protective activity of Panduratin A against thioacetamide-induced oxidative damage: demonstration with in vitro experiments using WRL-68 liver cell line.

BACKGROUND: Chalcone Panduratin A (PA) has been known for its antioxidant property, but its merits against oxidative damage in liver cells has yet to be investigated. Hence, the paper aimed at accomplishing this task with normal embryonic cell line WRL-68. METHODS: PA was isolated from Boesenbergia rotunda rhizomes and its 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging and ferric reducing power (FRAP) activities were measured in comparison with that of the standard reference drug Silymarin (SI). Oxidative damage was induced by treating the cells with 0.04 g/ml of toxic thioacetamide for 60 minutes followed by treatment with 1, 10 and 100 µg/ml concentrations of either PA or SI. The severities of oxidative stress in the control and experimental groups of cells were measured by Malondialdehyde (MDA) levels, superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx) activities. RESULTS: PA exhibited an acceptable DPPH scavenging and FRAP activities close to that of Silymarin. Treating the injured cells with PA significantly reduced the MDA level and increased the cell viability, comparable to SI. The activities of SOD, CAT and GPx were significantly elevated in the PA-treated cells in a dose dependent manner and again similar to SI. CONCLUSION: Collectively, data suggested that PA has capacity to protect normal liver cells from oxidative damage, most likely via its antioxidant scavenging ability.

Hepatoprotective effect of pinostrobin against thioacetamide-induced liver cirrhosis in rats.

The study in vivo assessed the effect of pinostrobin on the histology, immunohistochemistry, and biochemical parameters of thioacetamide (TAA) induced liver cirrhosis in Sprague Dawley rats. The rats were noticeably gavaged with two doses of pinostrobin (30 mg/kg and 60 mg/kg) with TAA and exhibited a substantial decrease in the liver index and hepatocyte propagation with much minor cell injury. These groups meaningfully down-regulated the proliferation of cellular nucleus antigen (PCNA) and alpha-smooth muscle actin (α-SMA). The liver homogenate displayed augmented antioxidant enzymes, superoxide dismutase (SOD) and catalase (CAT) activities escorted with reducing in malondialdehyde (MDA) level. The serum level of bilirubin, total protein, albumin, and liver enzymes (ALP, ALT, and AST) returned to normal and was similar to that of normal control and silymarin with TAA-treated groups. pinostrobin-fed groups also decreased the level of Tumor necrosis factor-alpha (TNF-α), Interleukin-6 (IL-6), and increased the level of Interleukin-10 (IL-10). Acute toxicity with a higher dose of 500 mg/kg of pinostrobin did not manifest any toxicological signs in rats. The hepatoprotective effect of pinostrobin could be due to potentially inhibited the progression of liver cirrhosis, down-regulation of PCNA and α-SMA proliferation, prevented oxidation of hepatocytes, improved SOD and CAT enzymes, condensed MDA, repairs of liver biomarkers, reduced cellular inflammation and modulation of inflammatory cytokines.

Efficacy of Boesenbergia rotunda Treatment against Thioacetamide-Induced Liver Cirrhosis in a Rat Model.

Background. Experimental research in hepatology has focused on developing traditional medicines into potential pharmacological solutions aimed at protecting liver from cirrhosis. Along the same line, this study investigated the effects of ethanol-based extract from a traditional medicine plant Boesenbergia rotunda (BR) on liver cirrhosis. Methodology/Results. The BR extract was tested for toxicity on 3 groups of rats subjected to vehicle (10% Tween 20, 5 mL/kg) and 2g/kg and 5g/kg doses of the extract, respectively. Next, experiments were conducted on a rat model of cirrhosis induced by thioacetamide injection. The rats were divided into five groups and, respectively, administered orally with 10% Tween-20 (5 mL/kg) (normal control group), 10% Tween-20 (5 mL/kg) (cirrhosis control group), 50 mg/kg of silymarin (reference control group), and 250 mg/kg and 500 mg/kg of BR extract (experimental groups) daily for 8 weeks. The rats in normal group were intraperitoneally injected with sterile distilled water (1 mL/kg) 3 times/week, and those in the remaining groups were injected intraperitoneally with thioacetamide (200 mg/kg) thrice weekly. At the end of the 8 weeks, the animals were sacrificed and samples were collected for comprehensive histopathological, coagulation profile and biochemical evaluations. Also, the antioxidant activity of the BR extract was determined and compared with that of silymarin. Data from the acute toxicity tests showed that the extract was safe to use. Histological analysis of the livers of the rats in cirrhosis control group revealed uniform coarse granules on their surfaces, hepatocytic necrosis, and lymphocytes infiltration. But, the surfaces morphologically looked much smoother and the cell damage was much lesser in those livers from the normal control, silymarin and BR-treated groups. In the high-dose BR treatment group, the livers of the rats exhibited nearly normal looking lobular architecture, minimal inflammation, and minimal hepatocyte damage, the levels of the serum biomarkers and liver enzymes read nearly normal, and these results were all comparable to those observed or quantified from the normal and silymarin-treated groups. The BR extract had the antioxidant activity about half of what was recorded for silymarin. Conclusion. The progression of the liver cirrhosis can be intervened using the ethanol-based BR extract, and the liver's status quo of property, structure, and function can be preserved. This capability of the extract warrants further studies exploring the significance of its pharmacologic potential in successfully treating the liver cirrhosis in humans.

Protective Role of Phyllanthus niruri Extract against Thioacetamide-Induced Liver Cirrhosis in Rat Model.

A preclinical study was performed to determine if the extract from Phyllanthus niruri (PN) plays a protective role against liver cirrhosis induced by thioacetamide (TAA) in rats. Initially, acute toxicity was tested and the results showed that the extract was benign when applied to healthy rats. Next, the therapeutic effect of the extract was investigated using five groups of rats: control, TAA, silymarin, and PN high dose and low dose groups. Significant differences were observed between the TAA group and the other groups regarding body and liver weights, liver biochemical parameters, total antioxidant capacity, lipid peroxidation, and oxidative stress enzyme levels. Gross visualization indicated coarse granules on the surface of the hepatotoxic rats' livers, in contrast to the smoother surface in the livers of the silymarin and PN-treated rats. Histopathological analysis revealed necrosis, lymphocytes infiltration in the centrilobular region, and fibrous connective tissue proliferation in the livers of the hepatotoxic rats. But, the livers of the treated rats had comparatively minimal inflammation and normal lobular architecture. Silymarin and PN treatments effectively restored these measurements closer to their normal levels. Progression of liver cirrhosis induced by TAA in rats can be intervened using the PN extract and these effects are comparable to those of silymarin.

Mechanisms of Gastroprotective Effects of Ethanolic Leaf Extract of Jasminum sambac against HCl/Ethanol-Induced Gastric Mucosal Injury in Rats.

Jasminum sambac is used in folk medicine as the treatment of many diseases. The aim of the present investigation is to evaluate the gastroprotective effects of ethanolic extracts of J. sambac leaves against acidified ethanol-induced gastric ulcers in rats. Seven groups of rats were orally pre-treated with carboxymethylcellulose (CMC) as normal group, CMC as ulcer group, 20 mg/kg of omeprazole as positive group, 62.5, 125, 250, and 500 mg/kg of extract as the experimental groups, respectively. An hour later, CMC was given orally to normal group and acidified ethanol solution was given orally to the ulcer control, positive control, and the experimental groups. The rats were sacrificed after an hour later. Acidity of gastric content, the gastric wall mucus, ulcer areas, and histology and immunohistochemistry of the gastric wall were assessed. Gastric homogenates were determined for prostaglandin E(2) (PGE(2)), superoxide dismutase (SOD), andmalondialdehyde (MDA) content. Ulcer group exhibited significantly severe mucosal injury as compared with omeprazole or extract which shows significant protection towards gastric mucosal injury the plant promotes ulcer protection as it shows significant reduction of ulcer area grossly, and histology showed marked reduction of edema and leucocytes infiltration of submucosal layer compared with ulcer group. Immunohistochemistry showed overexpression of Hsp70 protein and downexpression of Bax protein in rats pretreated with extract. Significant increased in the pH, mucus of gastric content and high levels of PGE(2), SOD and reduced amount of MDA was observed.

Acute toxicity evaluation, antibacterial, antioxidant and immunomodulatory effects of Melastoma malabathricum.

Melastoma malabathricum (MM) is a well-known plant in Malaysian traditional medicine, locally known as senduduk. Its ethanol and aqueous extracts have been used in the present investigation to study the immunomodulatory role on human peripheral blood mononuclear cell (PBMC), and the DPPH, ABTS and FRAP free radical scavenging activities were also measured. Total flavonoids and total phenolic contents were assayed and the antibacterial effect was tested against four species of bacteria; two Gram-positive (Staphylococcus aureus and Streptococcus agalactiae) and two Gram-negative (Escherichia coli and Klebsilla pneumonia). The tests were carried out using the disc diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. Moreover, the acute toxicity was evaluated in vivo on the ethanol extract of MM to establish its safety when administered orally. In our results, both extracts of MM showed abilities to scavenge DPPH and ABTS free radicals, IC(50) values: (11.599 ± 0.84, 10.573 ± 0.58 µmol/L) and (62.657 ± 0.78, 63.939 ± 0.48 µmol/L) for ethanol and aqueous extracts respectively. Indeed the ethanol extract evidenced high phenolic content (384.33 ± 0.005 mg/g), flavonoids contents (85.8 ± 0.009 mg/g) and ferric reducing antioxidant power (33,590 ± 0.038 mmol/g), with high activity against S. aureus and S. agalactiae (11 ± 0.3 and 12 ± 0.6 mm inhibition zones). Likewise, the percentage of peripheral blood mononuclear cells (PBMC) viability was increased in response to MM, IC(50) values (1.781 ± 1.2 and 6.545 ± 0.93 µg/mL) for ethanol and aqueous extracts, respectively. In addition, our results showed that the MM extract is safe even at a high dose of 5,000 mg/kg and has no oral toxicity. These findings suggest the excellent medicinal bioactivity of MM and explain the popularity of this plant in the folk medicine as a remedy for different illnesses.

Free radical scavenging, antimicrobial and immunomodulatory activities of Orthosiphon stamineus.

Orthosiphon stamineus is considered an important traditional folk medicine. In this study ethanol and aqueous extracts of O. stamineus were evaluated in vitro for their antioxidant, antimicrobial as well as for their immunomodulatory properties on human peripheral blood mononuclear cells (PBMCs). The DPPH radical scavenging method was used for the determination of antioxidant activity, while the antibacterial efficacy was investigated by both disc diffusion method and Minimum Inhibitory Concentration (MIC) against four bacterial strains (Gram-positive and Gram-negative). Furthermore, the immunomodulatory potential of the extracts was investigated through the MTT assay. Aqueous extract of O. stamineus exhibited significant free radical scavenging activity with IC50 50 9.6 µg/mL, whereas the IC50 for the ethanol extract was 21.4 µg/mL. The best antimicrobial activity was shown by the aqueous extract of O. stamineus against Staphylococcus aureus, with inhibition zone of 10.5 mm and MIC value 1.56 mg/mL. Moreover, the results observed from the MTT assay showed that both plant extracts stimulated the PBMCs proliferation in vitro in a concentration-dependent manner, but the aqueous extract has remarkable activity against PBMCs. These findings indicate that O. stamineus showed high antioxidant activity and may be considered as an immunomodulatory agent.

Assessment of in vitro antioxidant, antibacterial and immune activation potentials of aqueous and ethanol extracts of Phyllanthus niruri.

BACKGROUND: Recently much attention has been paid to biologically active plants because of their low production cost and fewer adverse effects compared with chemical drugs. In the present investigation the bioactivity of Phyllanthus niruri ethanol and aqueous extracts was evaluated in vitro. RESULTS: The ethanol extract of P. niruri showed a high level of flavonoid content (123.9 ± 0.002 mg g⁻¹), while the aqueous extract showed the highest 2,2-diphenyl-1-picrylhydrazyl (DPPH; IC50 6.85 ± 1.80 µmol L⁻¹) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS; 46.44 ± 0.53 µmol L⁻¹) free radical scavenging activities with high phenol content (376 ± 0.02 mg g⁻¹) and elevated levels of ferric reducing antioxidant power (FRAP; 23 883 ± 0.019 mmol g⁻¹) with excellent antibacterial activity against Staphylococcus aureus (20 mm inhibition zone) and Streptococcus agalactiae (12 mm inhibition zone), respectively, in addition to the best immune activation potential of human peripheral blood mononuclear cells (450.5%). CONCLUSIONS: It is clear from our results that both extracts of P. niruri has excellent bioactivity roles via elevated levels of antibacterial, antioxidant and percentage of peripheral blood mononuclear cell proliferation, which could lead to the development of medications for clinical use.

Antioxidant, cytotoxic activities, and structure-activity relationship of gallic acid-based indole derivatives.

A new series of gallic hydrazones containing an indole moiety was synthesized through the reaction of gallic hydrazide and different indole carboxaldehydes. Their antioxidant activities were determined on DPPH radical scavenging and inhibition of lipid peroxidation. The in-vitro cytotoxic activities of the compounds were evaluated against HCT-116 (human colon cancer cell line) and MCF-7 (estrogen-dependent human breast cancer cell line) by the MTT method. An attempt to correlate the biological results with their structural characteristics has been done. A limited positive structure activity relationship was found between cytotoxic and antioxidant activities.

Bis(acetato-κO,O')diphen-yl(pyridine-κN)tin(IV).

The asymmetric unit of the title compound, [Sn(C(6)H(5))(2)(C(2)H(3)O(2))(2)(C(5)H(5)N)], contains two crystallography independent mol-ecules. In both mol-ecules, the Sn(IV) atom is seven-coordinated in a distorted penta-gonal-bipyramidal geometry with the two phenyl groups in axial positions. The two mol-ecules differ mainly in the torsion of the phenyl and pyridine rings. The dihredral angles between the phenyl rings are 89.54 (15) and 60.11 (14)° in the two mol-ecules while the dihedral angles between the pyridine rings and the acetate groups are 12.6 (2) and 41.77 (13)° in the two mol-ecules.

Bis(pyridine-κN){N,N-[1,1'-(pyridine-2,6-di-yl)diethyl-idyne]benzene-sulfono-hydrazonato-κO,N,N',N'',O'}nickel(II).

In the crystal structure of the title compound, [Ni(C(21)H(19)N(5)O(4)S(2))(C(5)H(5)N)(2)], the metal center is seven-coordinate, with an approximate penta-gonal-bipyramidal configuration. The Ni atom is chelated by a dianionic penta-dentate Schiff base via the pyridine N atom, the two azomethine N atoms and the two sulfonyl O atoms. The latter coordinate to Ni at different distances, viz. 2.3337 (12) and 2.7988 (12) Å. Two apically coordinated pyridine mol-ecules complete the seven-coordin-ate geometry. The dihedral angle between the two pyridine ring planes is 68.25 (6)°.

N'-[1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]-3,4,5-trihydroxy-benzohydrazide dimethyl sulfoxide solvate trihydrate.

The benzohydrazide mol-ecule in the title compound, C(15)H(13)BrN(2)O(5)·C(2)H(6)OS·3H(2)O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.078 Å. The organic mol-ecules, water and dimethyl sulfoxide solvent mol-ecules are linked by N-H⋯O, O-H⋯O and O-H⋯S inter-molecular hydrogen bonds, forming zigzag chains along the a axis. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds also occur.

A second monoclinic polymorph of 2-(diformyl-methyl-idene)-3,3-dimethyl-2,3-dihydro-1H-indole.

The crystal structure of the title compound, C(13)H(13)NO(2), is a polymorph of the structure first reported by Helliwell et al. [Acta Cryst. (2006), E62, o737-o738]. It is also monoclinic (space group P2(1)/c), but with completely different cell constants. The mol-ecular conformations of these polymorphs differ by a 180° rotation of one formyl group. The present mol-ecule is planar [maximum deviation 0.089 (2) Å] with the exception of the two methyl groups which lie on either side of the plane. There are strong intra- and inter-molecular N-H⋯O hydrogen bonds. The latter link pairs of mol-ecules across crystallographic centers of symmetry. Two aldehyde O atoms are brought close together [2.896 (4) Šin this arrangement but are not hydrogen bonded. In the earlier polymorph, one formyl group is rotated by 180° to yield inter-molecular hydrogen bonding and an infinite polymeric chain. The other formyl group is involved in the same intra-molecular hydrogen bonding as has been found here.

3,4,5-Trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide-1H-indole-2-carbaldehyde azine-methanol (2/1/2).

The title compound, 2C(16)H(13)N(3)O(4)·C(18)H(14)N(4)·2CH(4)O, was crystallized from the reaction between 3,4,5-trihydroxy-benzoyl-hydrazine and indole-2-carbaldehyde in a mixture of ethanol and methanol. The compound is a stoichiometric 2:1 cocrystal of the methanol-solvated reaction product, 3,4,5-trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide and 1H-indole-2-carbaldehyde azine that arose unexpectedly during the synthesis. The former mol-ecules are linked by O-H⋯O hydrogen bonds and also by π-π stacking inter-actions between benzoyl-hydrazide rings into a two-dimensional network. The methanol solvent mol-ecules are hydrogen bonded to this network. The centrosymmetric azine mol-ecules are not engaged in hydrogen bonding.

3,4,5-Trihydr-oxy-N'-[(1-methyl-1H-indol-2-yl)methyl-idene]benzohydrazide.

The structure of the title compound, C(17)H(15)N(3)O(4), displays inter-molecular O-H⋯N and O-H⋯O hydrogen bonding between adjacent mol-ecules. Intra-molecular O-H⋯O hydrogen bonds also occur. The molecule is essentially planar with a deviation of 0.090 (1) Šfrom the best plane running through the connected ring systems.

N'-(2,4-Dimethoxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide ethanol solvate.

The title compound, C(16)H(16)N(2)O(6)·C(2)H(5)OH, was synthesized from 3,4,5-trihydroxy-benzoyl-hydrazide and 2,4-dimethoxy-benzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydr-oxy groups are involved in both intra-molecular O-H⋯O and inter-molecular O-H⋯N and O-H⋯O hydrogen bonds and a C-H⋯O interaction also occurs.