Chemical investigation of the methanolic extract from the twigs of Sclerocroton cornutus (Pax) led to the isolation of one new rosane diterpene-type derivative named Sapirosanic acid (1) along with nine known compounds including: xylopic acid (2), 3,3'-di-O-methylellagic acid (3), 3-3'-di-O-methyl ellagic acid-4'-O-α-L-rhamnose (4), ursolic acid (5), (20 R)-cholest-4-en-3-one (6), a mixture of stigmasterol (7) and ß-sitosterol (8) and a mixture of ß-sitosterol-3-O-ß-glucopyranoside (9) and stigmasterol-3-O-ß-glucopyranoside (10). The structures of these compounds were elucidated by the interpretation of 1D and 2D NMR spectroscopy, electrospray ionisation mass spectrometry (ESI-MS), and comparison with literature data. Using microdilution methods, the crude extract, fractions and isolated compounds were evaluated in vitro for their antibacterial activities against three multidrug-resistant Staphylococcus aureus strains and one clinical isolate. Additionally, fractions were assayed for their antioxidant properties using 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS), 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Ferric reducing antioxidant power (FRAP) methods. The results of all these assays will also be discussed.

Lenzites acuta Berk. is a wood-decaying polypore mushroom from tropical forests that remains chemotaxonomically unexplored. In this study, the chemical constituents from the methanolic extract of its fruiting bodies yielded a new ceramide, polyporamide (1), together with three sterols: stellasterol (2), ergosterol (3), and ergosterol peroxide (4). Acetylation of the new ceramide (1) afforded a new hemi-synthetic derivative, polyporamide tetraacetate (1a). Structural elucidation was achieved by 1D and 2D NMR, ESI-MS, and comparison with literature data. The antibacterial activity of the extract and isolated compounds was assessed against Pseudomonas aeruginosa and Staphylococcus aureus. Compound 1a displayed the strongest antibacterial effect, with MIC values of 128 mu g/mL (P. aeruginosa) and 64 mu g/mL (S. aureus). Antibiofilm activity was evaluated using a microtiter plate assay with safranine staining at sub-MIC concentrations. Compound 4 exhibited the highest inhibition of biofilm formation, with 69.35 % inhibition against P. aeruginosa and 51.59 % against S. aureus at 128 mu g/mL. Although less active than the reference drug gentamicin, compounds 1a and 4 appear as potential scaffolds for the development of antibacterial and antibiofilm agents. This study constitutes the first report on the chemical constituents of L. acuta and highlights its potential as a source of bioactive natural products.

This study aimed to investigate the chemical constituents of the trunk bark of Xylopia quintasii and evaluate the antibacterial potential of its isolated terpenoids, with a focus on the structural characterisation and polymorphism of (−)-rhinocerotinoic acid (1). The petroleum ether fraction of the methanol extract was subjected to chromatographic separation, leading to the isolation of eight terpenoids, including six diterpenoids and two lupane-type triterpenoids. Single-crystal X-ray diffraction was employed to determine the molecular framework and relative stereochemistry of (−)-rhinocerotinoic acid (1). Optical rotation, Flack parameter analysis, and complementary spectroscopic techniques (CD, VCD, or chiral HPLC) were considered to assess stereochemistry. Antibacterial activity was evaluated against Gram-negative enterobacteria, and molecular docking was performed on the MurA enzyme to explore potential mechanisms. Among the diterpenoids, (−)-rhinocerotinoic acid (1) was identified as a labdane-type compound, crystallising in a triclinic P1 system representing a new polymorph. Optical rotation ( [ ]_D^24 −2.04, c = 0.2, MeOH) and Flack parameter (0.20) indicated that the absolute configuration could not be unambiguously assigned. Several diterpenoids exhibited higher antibacterial activity than the crude extract, with 3β-hydroxy-copalic acid (3) showing the most potent effect (MIC = 50 µg/mL against E. coli). Docking studies suggested potential interactions with the MurA catalytic site, although predictions for compound 1 were less reliable (RMSD = 4.48 Å). Xylopia quintasii trunk bark contains chemically diverse labdane- and kaurane-type diterpenoids. The identification of a new polymorphic form of (−)-rhinocerotinoic acid (1), together with the selective antibacterial activity of certain diterpenoids, highlights their chemotaxonomic significance and potential as scaffolds for further pharmacological studies.

Since the last decades, Detarium microcarpum have been used and studied due to the significant properties to threat various ailments. It is therefore crucial to ascertain the safety properties of is phytoconstituents. The present study was taken up to investigate the oral acute toxicity, 28 days repeated oral sub-acute toxicity study of D. microcarpum root bark extract in Albino Wistar rats, molecular docking, and molecular dynamic simulation. Based on acute oral toxicity, the LD50 value of the extract was considered "non-toxic" up to a 5000 mg/kg b.w. The regular administration of the extract post 28-day treatment was also qualified as safe based on the body and organ weight, hematological, biochemical, and histopathological results in the sub-acute toxicity assay. The majority of the previous identified and isolated compounds passed the ADMET analysis, and the molecular docking identified 1,7-dihydroxy-6-methylxanthone (15) as the top one candidate with an effective binding affinity of -8.1, and - 7.5 (kcal/mol), for P450 and UGT2B7 proteins respectively. This compound was then further assessed using MD simulation, which verified the molecules' stability and binding to the targeted protein. Collectively these data build the foundation of support demonstrating that D. microcarpum root bark extract could be considered as a promising medicinal drug and concluded its suitable used for pharmacological purposes.

AimThe reactions of various heterocyclic primary amines with sulfonyl chloride derivatives or with sulfosalicylic acid results in the first case to the formation of sulfonamide derivatives and in the second case to the formation of sulfonate organic salts which are both hybrid molecule that integrate multiple pharmacophores into a single scaffold.Materials and methodsThe novel sulfonamide derivatives 3 were obtained through mono-nucleophilic addition reactions of the corresponding primary amines to the appropriate sulfonyl derivative. In contrast, the sulfonate organic salts 5, 7 and 8 were formed as the result of an acid-base neutralization reaction, during which a molecule of amine captures the acid proton from the sulfosalicylic acid molecule. The antioxidant activity of the synthesized compounds is evaluated by determining their DPPH (2,2-Diphenyl-1-picrylhydrazyl) free radical scavenging activity as well as gallic acid equivalent antioxidant capacity (GEAC).Results and conclusionThe structures of compounds 3, 5, 7 and 8 were confirmed through elemental analysis, IR (Infrared), UV-Vis (ultraviolet-visible), 1H-NMR (Proton nuclear magnetic resonance), 13C-NMR (Carbon-13 nuclear magnetic resonance) and HRMS (High-Resolution Mass Spectrometry) spectroscopic data. Organic salt 7a was characterized by single-crystal and X-ray diffraction. Organic sulfonate salts were found to be more active than covalent sulfonamide derivatives.

The presence of pathogenic micro-organisms in drinking water is responsible for certain public health diseases. The use of plant extracts is an alternative to commonly used chemical and physical treatments. The aim of this study is to evaluate the hydroethanolic extracts of Lantana camara stems and leaves on the cultivability of planktonic bacteria Escherichia coli and Staphylococcus aureus in an aquatic microcosm, to determine the effect of extract concentration (0,5 g/L, 1 g/L, 1,5 g/L and 2 g /L), incubation temperature (7 and 37 degrees C) and incubation time (3, 6 and 9 hours) on the cultivability of bacterial cells and also to evaluate the effect of some bioactive compounds isolated from these bacteria. The bioactive compounds identified are Stigmasterol (sterol), lantanilic acid and lantic acid (triterpenes) isolated in the leaf extract of L. camara and beta-sistosterol (sterol) and oleanolic acid (triterpenes) isolated in the stem extract of L. camara. The cultivability of two bacterial strains studied is influenced by the presence of Lantana camara extract solution. A reduction in cell density was observed in the presence of the plant extract in question. With Lantana camara leaf extract, at an incubation temperature of 37 degrees C, the percentage of inhibition ranged from 3-100% for E. coli with the highest value observed after 6 hours at extract concentrations of 1.5 g/L and 2 g/L. In general, the extract has both a bactericidal and bacteriostatic effect on each bacterium, depending on the type of organ, whereas the effect of the bleach is specific to each bacterium. It should be noted that in the presence of E. coli, the MICs were 0.00048 mg/mL with the leaf extract and 0.0078 mg/mL with the stem extract. For this bacterium, the MBCs were 0.0039 mg/mL and 0.0312 mg/mL with the leaf and stem extracts respectively. For S. aureus, the MICs were 0.0156 mg/mL with the leaf extract and 0.0078 mg/mL with the stem extract and the MBCs were 0.0019 mg/mL and 0.0156 mg/mL (leaf and stem, respectively). The CMB/MIC ratio shows a bactericidal effect at the level of beta-sistosterol in E. coli. On the other hand, in S. aureus, this report shows a bacteriostatic effect and tolerance with the two isolated chemical compounds. The Kruskal-Wallis test shows that the abundance of cultivable cells of each bacterial species differed significantly from one incubation temperature to another at each extract concentration and at each incubation temperature for each part of the plant (P<0.05). The data obtained from this exploratory study makes it possible to consider the use of Lantana camara hydroethanolic extract as an alternative method in water disinfection.

Phytochemical investigation of the methanol extract from the fruits of Macaranga monandra (Euphorbiaceae Muell. et Arg.) afforded one new geranylated 1',2'-dihydrophenanthrene and two new flavonoid derivatives, named macamondrin (1), macamondrione A (2) and B (3) respectively. The structures of these compounds were elucidated mainly by NMR, mass spectral data and in comparison with data from the literature. Along with compounds 1-3, nine known compounds among which oleanolic acid (4); daucosterol (5); 3β-acetoxy-11α,12α-epoxytaraxerol (6); 3,3',4-tri-O-methylellagic acid (7); 3,3',4,4'-tetra-O-methylellagic acid (8); 4'-O-methyl-6-isoprenylapigenin (9); 4'-O-methyl-8 isoprenylkaempférol (10); 4'-O-methyl-6-isoprénylkaempférol (11); 6-isoprénylkaempférol (12), were also isolated. Crude extracts as well as isolated compounds were evaluated for their antioxidant activity using the ABTS, DPPH and FRAP methods. It appears that the 50 % radical scavenging concentrations ranging from 6.26 to 11.7 μg/ml on the ABTS radical, from 1.77 to 48.22 μg/ml on the DPPH radical, and from 1.54 to 67.97 μg/ml with the FRAP method. For the compounds tested, very good antioxidant activities were observed, which clearly shows that these molecules can have an anti oxidative stress potentiel.

The coupling reaction of diazonium ion of 2-amino-6-nitrobenzothiazole at 0-5 °C with distinctly substituted 2-aminobenzothiazole derivatives produced new 1,2,3,5-tetrazine derivatives. It was found that diazotized 2-amino-6-nitrobenzo[d]thiazol reacts with the ring nitrogen atom of varyingly substituted 2-aminobenzothiazole derivatives to yield tetrazine nucleus. The benzene ring of benzothiazole bearing electron donor group and annelated to the tetrazine was further substituted in situ by other 6-nitrobenzo[d]thiazol-2-yl) diazinyl to yield the final product. The structure of the prepared compounds was elucidated using their physical, elemental, and spectroscopic data. The synthesized compounds were tested for their antimicrobial and antibiofilm activities against Staphylococcus aureus and Escherichia coli bacteria. Two of the synthesis tetrazine derivatives exhibited interesting antibiofilm potential.

An estimated 57 million deaths are recorded worldwide every year out of which infectious diseases are responsible for 17 million; one-third of the overall mortality rate.To face this crucial issue, the search for new anti-infective agents that could be used by needy populations appeared primordial.The present study focused on Ochthocosmus africanus (Ixonanthaceae) known to be traditionally used in disease caretaking.The phytochemical screening of the hydroalcoholic extract from the plant trunk bark was followed by the determination of its antibacterial potential by macro-dilution in a liquid medium.The minimal inhibitory and bactericidal concentrations (MIC and MBC, respectively) were assessed on six Gram-negative rods (Klebsiella pneumoniae, Enterobacter aerogenes, Moraxella spp., Escherichia coli, Serratia odorifera, and Shigella sonnei) and three Gram-positive rods (Lactobacillus bulgaricus, Clostridium spp., and Bacillus spp.).The Phytochemical screening revealed the presence of secondary metabolites like flavonoids, anthocyanins, tannins, saponosides, triterpenes, cardiotonic heterosides, and reducing sugars.The antibacterial tests further revealed inhibitory and bactericidal features of the extract with MIC values ranging from 25 through 100 mg/mL; while the MBCs were recorded between 50 and 200 mg/mL.Bactericidal activity was observed on Escherichia coli, Enterobacter aerogenes, Shigella sonnei, Clostridium spp, and Lactobacillus bulgaricus (CMB/CMI=2) and bacteriostatic activity on the others.These findings could justify, at least partially, the use of this plant in infectious; but additional efforts on toxicity are needed for safer healthcare.

Ethnopharmacological relevance: Detarium microcarpum is used to treat typhoid fever, a major public health problem, by indigenous population in Africa. Though its preventive activities have been documented, the curative effect is still to be confirmed.Aim of the study: This study aimed at evaluating the curative effects of the hydroethanolic extract of Detarium microcarpum root bark on Salmonella typhimurium-induced typhoid in rat and exploring the in-silico inhibition of some bacterial key enzymes.Study design: In vitro antioxydant, in vivo antisalmonella of the extract and in silico molecular docking assay on the isolated compounds were carried out to explore the anti-salmonella effects of Detarium microcarpum.Material and methods: The in vitro antioxidant properties of the extract were evaluated using DPPH, ABTS and FRAP tests. The anti-salmonella activity of the extract was assessed through feacal sample from Salmonella typhimurium-infected rat cultured in Salmonella-Shigella agar (SS agar) medium. The affinity of isolated com-pounds (Rhinocerotinoic acid and Microcarposide) from the extract were performed on four key enzymes (Adenylosuccinate lyase, Acetyl coenzyme A synthetase, Thymidine phosphorylase and LuxS-Quorum sensor) using molecular docking simulation to elucidate the molecular level inhibition mechanism.Results: Crude extract of D. microcarpum root bark showed variable activities on DPPH (RSa50: 6.09 +/- 1.04 mu g/ mL), ABTS (RSa50: 24.46 +/- 0.27), and FRAP (RSa50: 23.30 +/- 0.23). The extract at all the doses exhibited significant healing effect of infected rats, with the complete clearance. The extract restored hematological, biochemical and histological parameters closed to the normal control. The molecular docking results indicates that rhinocerotinoic acid and microcarposide present more affinity to the LuxS-Quorum sensor and Acetyl co-enzyme A synthetase protein as compared to the others.Conclusion: These results demonstrate potent anti-typhoid activities of the hydroethanolic of Detarium micro-carpum root bark extract through antioxidant properties and high inhibitory affinity of its compounds on some bacterial key enzymes that justify its use as traditional medicine to typhoid fever.

The chemical investigation of the leaf extract of a Cameroonian medicinal plant, Lippia rugosa A Chev (Verbenaceae) led to the isolation of a new flavonoid derivative flavolippia (1), alongside eleven known compounds: 2,4-dimethylpyridin-3,5-diol (2), 5-hydroxy-6,7,4'-trimethoxylflavone (3), 5-hydroxy-3,7,4'-trimethoxyflavone (4), 7-hydroxy-5,6,4'-trimethoxyflavone (5), 3 beta-hydroxy-urs-12-en-3-ol (alpha-amyrin) (6), lupeol acetate (7), lup-20(29)-en-3 beta-ol (lupeol) (8), lup-20(29)-en-3 beta,28-diol (betulin) (9), fridelan-3-one (fridelan) (10), saccharose (11), cosanol (12). In addition, a new semi-synthetic alkaloid derivative named lippiamicin (13) was prepared from 2,4-dimethylpyridin-3,5-diol (2). Their structures were established on the basis of their spectroscopic data, as well as 1 D and 2 D NMR. Compounds 1-13 were evaluated for their antioxidant activities. The results obtained showed that compounds 2 and 12 were the most active with IC50 values of 0.145 +/- 0.011 and 0.195 +/- 0.017 mu M/mL respectively (for DPPH center dot) and 0.241 +/- 0.027 and 0.223 +/- 0.024 mu M/mL respectively (for FRAP) compared to butylated hydroxyltoluene used as positive control.

Microbial resistance is facilitated by biofilm formation and quorum-sensing mediated processes. In this work, the stem bark (ZM) and fruit extracts (ZMFT) of Zanthoxylum gilletii were subjected to column chromatography and afforded lupeol (1), 2,3-epoxy-6,7-methylenedioxyconiferyl alcohol (3), nitidine chloride (4), nitidine (7), sucrose (6) and sitosterol-β-D-glucopyranoside (2). The compounds were characterized using MS and NMR spectral data. The samples were evaluated for antimicrobial, antibiofilm and anti-quorum sensing activities. Highest antimicrobial activity was exhibited by compounds 3, 4 and 7 against Staphylococcus aureus (MIC 200 µg/mL), compounds 3 and 4 against Escherichia coli (MIC = 100 µg/mL) and compounds 4 and 7 against Candida albicans (MIC = 50 µg/mL). At MIC and sub-MIC concentrations, all samples inhibited biofilm formation by pathogens and violacein production in C. violaceum CV12472 except compound 6. Good disruption of QS-sensing in C. violaceum revealed by inhibition zone diameters were exhibited by compounds 3 (11.5 ± 0.5 mm), 4 (12.5 ± 1.5 mm), 5 (15.0 ± 0.8 mm), 7 (12.0 ± 1.5 mm) as well as the crude extracts from stem barks (16.5 ± 1.2 mm) and seeds (13.0 ± 1.4 mm). The profound inhibition of quorum sensing mediated processes in test pathogens by compounds 3, 4, 5 and 7 suggests the methylenedioxy- group that these compounds possess as the possible pharmacophore.

Abstract From Rinorea oblongifolia fruits, 3-Nor-4β-friedelan-24-ol (1) and 3-decyl-6,7,8-trimethoxy-2H,5H-furo[4,3,2-de]isochromene-2,5-dione (4), new derivatives alongside, 28-hydroxyfriedelan-3-one (2), friedelin (3), 3,3’,4,4’,5’-pentamethylcoruleoellagic acid (5), hexamethylcoruleoellagic acid (6), 3’,4,4’,5,5’-pentamethylcoruleoellagic acid (7), and fatty compounds 8-11 were isolated and characterized using HRESIMS, EIMS, 1D and 2D NMR. In vitro enzyme inhibition of compounds 1, 2, 4, 5, 6 and 7 were evaluated on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), α-glucosidase, urease and tyrosinase. Against AChE and BChE, the phenolic compounds 4, 5, 6, and 7 had good activity probably due to the phenolic nature and methoxy substituents. Compounds 4, 5, 6 and 7 exhibited good α-glucosidase inhibition especially compound 4 whose IC50 = 42.45 ± 0.46 µg/mL was close that of acarbose (IC50 = 20.52 ± 0.84 µg/mL) standard drug. Urease and tyrosinase were appreciably inhibited by the compounds. Overall results of enzyme inhibitory assays indicate Rinorea oblongifolia, fruits and its constituents as potential remedy for enzymatic disorders. Graphical Abstract

A series of novel tetrazine derivatives, containing benzothiazole framework, were prepared during the coupling reactions of some diazotized 2-aminobenzo[d]thiazole derivatives with p-acetaminophen.Their structures were elucidated based on NMR and MS spectrometry.The anticancer activity and the safety of the synthesized compounds along with the entire precursors were assessed against three human cancer cell lines and a normal cell line.All the synthesized compounds showed selective cytotoxic activity against the cancer cell lines used in comparison to the normal Vero cell line.Their IC50 values varied from 2.02 to 171.67 µM.

Phytochemical study of the aquatic plant Dicraeanthus zehnderi H. Hess., led to the isolation of eleven compounds, including one alkaloid [2′-acetamido-3′-phenylpropyl-2-benzamido-3-phenylpropionate (1)], one fatty alcohol [Tridecanol (2)] and nine known xanthones [Caloxanthone A (3), Caloxanthone C (4), Trapezifoliaxanthone (5), 1,7-dihydroxyxanthone (6), Norathyriol (7), 1,5,8-trihydroxy-3-methoxyxanthone (8), 6-deoxyisojacareubin (9), Linixanthone C (10) and Tovoxanthone (11)]. The compounds (1) and (2) were isolated from this family for the first time while the isolated xanthones (3–11) were reported from the Dicraeanthus genus for the first time. The structures of these compounds were identified by spectroscopic methods and compared with the published data with given references. The chemotaxonomic significance of the isolates was also discussed.

A new naphtalenone derivative named fragranone, alongside seventeen known compounds: ten triterpenoids, one monoglycerol, one polyterpenoid, one carotenoid, two steroids and two polyols were isolated from the leaves and roots of Diospyros fragrans. Four semi-synthetic derivatives obtained from the acetylation and allylation of betulinic acid, allylation of ursolic acid and acetylation of vismiaefolic acid are also reported. The structures of the compounds were established using their MS and NMR spectral data. The chemotaxonomic relevance of the compounds is also discussed in this paper. The extracts, as well as the isolates and the semi-synthetic compounds were evaluated for their antibacterial and cytotoxic activities. The obtained results showed a moderate anti-bacterial activity for myrtifolic acid and the semi-synthetic compound betulinic acid acetate against Bacillus subtilis DSMZ 704 with a diameter zone of inhibition of 9 and 10 mm, respectively. Ursolic acid and corosolic acid exhibited a moderate cytotoxicity against human colorectal adenocarcinoma cells HT-29 and the cervix carci-noma cells KB-3-1 with inhibitory concentration 50 values of 34.4 and 50.9 mu M for ursolic acid, and 16.5 and 14.6 mu M for corosolic acid, respectively.

The bio guided fractionation of the dichloromethane/methanol (1:1) crude extract of the air-dried whole plant of C. aegyptiaca led to the isolation of one new flavone derivative designated conyflavone (1) and one new clerodane diterpene type designated conyclerodane (2) along with five known compounds including two flavonoids Gardenin C (3), chrysosplenetin (4) and two steroids glucoside of β-sitosterol (5), the mixture of stigmasterol (6) and β-sitosterol (6') and ent-2b,18,19trihydroxycleroda-3,13-dien-16,15-olide (7). The structures were established by spectroscopic methods including IR, 1D and 2D NMR in conjunction with mass spectroscopy and by comparison to data of related compounds described in literature. The stereocentres in compound 2 were determined by SC-XRD analysis. Crude extract as well as fractions and pure compounds were evaluated in vitro for their antibacterial activities against four pathogenic and two clinical isolate strains using microdilution methods. Extracts and compounds displayed a moderate antibacterial activity with MIC values ranging from 125 to 500 µg/mL.

As part of our search for new secondary metabolites from Macaranga hurifolia Beille, a phytochemical investigation was carried out on the fruits that led to the isolation and characterization of two new prenylated flavonol derivatives named macafolias A (1) and B (2), along with five known compounds. Their chemical structures were established on the basis of extensive analysis of their 1-D and 2-D NMR (H-1, C-13, APT, COSY, HSQC and HMBC) in conjunction with mass spectroscopy and by comparison with data from the literature. The in vitro assay of the antibacterial potency of the crude extract, fractions and some pure compounds were evaluated against a wide range of bacteria strains.

Abstract The chemical investigation of the ethanol/water (7:3) extract of the roots of Detarium microcarpum (Fabaceae) led to the isolation of one new labdane diterpenoid, microcarpin (1) and one new ceramide derivative, microcarpamide (2), along with eight known secondary metabolites (3–10) including, 5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid (3), microcarposide (4), rhinocerotinoic acid (5), 1,7-dihydroxy-6-methylxanthone (6), ursolic acid (7), 3β,23-dihydroxylup-20(29)-en-28-oic acid (8), alphitolic acid (9), and stigmasterol glucoside (10). The structures of these compounds were elucidated based on their spectroscopic data. Although compounds 3 and 4 are known, their crystalline structures are reported here for the first time. These compounds were evaluated in vitro for their antisalmonella activity. The results obtained showed that, microcarpamide (2), microcarposide (4), and rhinocerotinoic acid (5) were moderately active against three salmonella strains: Salmonella typhi, Salmonella enteritidis and Salmonella typhimirium, with minimum inhibition concentration values of 76.7 and 153.5 μM.