A New Isoflavanol from the Fruits of Kotschya strigosa (Fabaceae)

The phytochemical investigation of the MeOH extract from fruits of Kotschya strigosa using repeated normal and reversed‐phase column chromatography and Sephadex LH‐20 chromatography led to the isolation and characterization of a new isoflavanol, named kotstrigoisoflavanol ( 1 ), together with three known compounds, diosmetin ( 2 ), β‐sitosterol ( 3 ), and the 3‐O‐β‐d‐glucopyranoside of β‐sitosterol ( 4 ). The antioxidant activity of crude extract, 1, and 2 was determined using the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH˙) method. The crude extract (IC₅₀ 61.7 ± 0.2 μg/ml) and 2 (IC₅₀ 70.2 ± 0.1 μg/ml) showed moderate antioxidant activities, while 1 was weakly active (IC₅₀ 153.1 ± 0.1 μg/ml), as compared with the standard reference l ‐ascorbic acid (IC₅₀ 21.9 ± 0.0 μg/ml).     

Green synthesis and characterizations of Nickel oxide nanoparticles using leaf extract of Rhamnus virgata and their potential biological applications

In the present report, Nickel oxide nanoparticles (NiONPs) were synthesized using Rhamnus virgata (Roxb.) (Family: Rhamnaceae) as a potential stabilizing, reducing and chelating agent. The formation, morphology, structure and other physicochemical properties of resulting NiONPs were characterized by Ultra violet spectroscopy, X‐ray diffraction (XRD), Fourier Transform Infrared analysis (FTIR), Scanning electron microscopy (SEM), Energy‐dispersive‐spectroscopy (EDS), Transmission electron microscopy (TEM), Raman spectroscopy and dynamic light scattering (DLS). Detailed in vitro biological activities revealed significant therapeutic potential for NiONPs. The antimicrobial efficacy of biogenic NiONPs was demonstrated against five different gram positive and gram negative bacterial strains. Klebsiella pneumoniae and Pseudomonas aeruginosa (MIC: 125 μg/mL) were found to be the least susceptible and Bacillus subtilis (MIC: 31.25 μg/mL) was found to be the most susceptible strain to NiONPs. Biogenic NiONPs were reported to be highly potent against HepG2 cells (IC₅₀: 29.68 μg/ml). Moderate antileishmanial activity against Leishmania tropica (KMH₂₃) promastigotes (IC₅₀: 10.62 μg/ml) and amastigotes (IC₅₀: 27.58 μg/ml) cultures are reported. The cytotoxic activity was studied using brine shrimps and their IC₅₀ value was recorded as 43.73 μg/ml. For toxicological assessment, NiONPs were found compatible towards human RBCs (IC₅₀: > 200 μg/ml) and macrophages (IC₅₀: > 200 μg/ml), deeming particles safe for various applications in nanomedicines. Moderate antioxidant activities: total antioxidant capacity (TAC) (51.43%), 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) activity (70.36%) and total reducing power (TRP) (45%) are reported for NiONPs. In addition, protein kinase and alpha amylase inhibition assays were also performed. Our results concluded that Rhamnus virgata synthesized NiONPs could find important biomedical applications with low cytotoxicity to normal cells.     

N-Hydroxypyridone alkaloids,chromone derivatives,and tetrahydroxanthones from the scale-insect pathogenic fungus Orbiocrella sp. BCC 33248

Six new compounds, an N-hydroxypyridone glucoside, orbiocrellin A (1), its aglycone orbiocrellin B (2), chromone glucosides 3 and 4, a dihydrochromone 5a/5b, and a chromone 6, were isolated from the scale-insect pathogenic fungus Orbiocrella sp. BCC 33248. Orbiocrellin A (1) exhibited antimalarial activity against Plasmodium falciparum K1 (IC₅₀ 3.1 μg/mL) while it was non-cytotoxic. In contrast, orbiocrellin B (2) showed both antimalarial (IC₅₀ 2.1 μg/mL) and cytotoxic (NCI-H187 cells, IC₅₀ 0.70 μg/mL) activities.     

4‐Chlorothiazole‐5‐carbaldehydes as Potent Precursors for Synthesis of Some New Pendant N‐heterocyces Endowed with Anti‐Tumor Activity

In our approach to synthesize bioactive molecules, a series of novel N‐heterocycles were synthesized and evaluated for their in vitro antitumor activity against a panel of three human cancer cell lines, namely, human breast cancer cell line (MCF‐7), human cervical cancer cell line (HeLa), and human prostate cancer PC‐3. The majority of the tested compounds exhibited significant cytotoxic activity toward the tested tumor cell lines. Analogues 33 , 34 , 31 , 38 , 21 , 23 , 22 , and 20 exhibited considerable cytotoxic activities comparable with standard drug 5‐fuorouracil. Compound 33 displayed superior cytotoxicity with IC₅₀ value of 4.12 ± 1.21 μg/mL against HeLa tumor cell line.     

New Cytotoxic Laurene‐, Cuparene‐, and Laurokamurene‐Type Sesquiterpenes from the Red Alga Laurencia obtusa

Three new sesquiterpene alcohols, laur‐2‐ene‐3,12‐diol ( 1 ), cuparene‐3,12‐diol ( 2 ), and 8,11‐dihydro‐1‐methoxylaurokamuren‐12‐ol ( 3 ), along with one known diterpene, kahukuen‐10‐ol ( 4 ) have been isolated from the organic extract of the red alga Laurencia obtusa. The chemical structures were elucidated on the basis of spectroscopic analysis. The cytotoxicity of the isolated compounds were evaluated against three cancer cell lines, i.e., KB, HepG2, and MCF‐7. Compound 4 exhibited a wide range of cytotoxic activity against KB, HepG2, and MCF‐7 cell lines with IC₅₀ of 0.100, 0.057, and 0.054 μm, respectively. In addition, 1 showed moderate activities towards KB and MCF‐7 cell lines with IC₅₀ values of 0.171 and 0.184 μM , respectively and 2 exhibited a moderate activity against KB cell line at a concentration of 0.213 μg/ml. On the other hand, compound 3 exhibited no cytotoxic activity against any of the three cell lines.     

Antiplasmodial and antiviral cyclohexadepsipeptides from the endophytic fungus Pullularia sp. BCC 8613

Four new cyclohexadepsipeptides, pullularins A-D, were isolated from the endophytic fungus Pullularia sp. BCC 8613. Structures of these compounds were elucidated by interpretation of NMR spectroscopic and mass spectrometric data. The absolute configurations of amino acid and hydroxy acid residues were determined by HPLC analysis of depsipeptide acid hydrolyzates using a chiral column and Marfey's method. Pullularin A exhibited activities against the malarial parasite Plasmodium falciparum K1 (IC₅₀ 3.6 μg/mL) and herpes simplex virus type 1 (HSV-1; IC₅₀ 3.3 μg/mL), whereas it showed weak cytotoxicity to Vero cells (IC₅₀ 36 μg/mL).     

Design,Synthesis, and in vitro Anti‐mycobacterial Evaluation of Propylene‐1H‐1,2,3‐triazole‐4‐methylene‐tethered (Thio)semicarbazone‐isatin‐moxifloxacin Hybrids

A new class of propylene‐1H‐1,2,3‐triazole‐4‐methylene‐tethered (thio)semicarbazone‐isatin‐moxifloxacin hybrids 6a – h was designed, synthesized, and screened for their in vitro anti‐mycobacterial activities against Mycobacterium tuberculosis (MTB) H₃₇Rv and MDR‐TB as well as cytotoxicity in VERO cell line. All the synthesized hybrids (MIC: 0.05–2.0 μg/mL) exhibited excellent activities against M. tuberculosis H₃₇Rv and MDR‐TB; in particular, conjugate 6c (MIC: 0.05 and 0.12 μg/mL) was no inferior to the three references MXFX (MIC: 0.10 and 0.12 μg/mL), RIF (MIC: 0.39 and 32 μg/mL), and INH (MIC: 0.05 and >128 μg/mL) against the tested two strains. All hybrids (CC₅₀: 2–8 μg/mL) were much more cytotoxic than the parent MXFX (CC₅₀: 128 μg/mL) should be further optimized.     

Synthesis of Novel 1,2,4‐Triazole‐3‐thione Derivatives as Influenza Neuraminidase Inhibitors

A series of 1,2,4‐triazole‐3‐thione derivatives ( 6a – 6t ) were synthesized and evaluated against influenza viruses (H1N1) neuraminidase (NA) in vitro. Eighteen compounds exhibited inhibitory potency with IC₅₀ values ranging from 14.68 ± 0.49 to 39.85 ± 4.23 μg/mL. Among them, compounds 6e and 6h showed significant inhibitory activity with IC₅₀ values of 14.97 ± 0.70 and 14.68 ± 0.49 μg/mL, respectively. Structure activity relationships were established. Molecular docking studies were performed to understand the binding interaction between active compounds and NA.     

New Compounds from the Roots and Stems of Trigonostemon lii and Their Cytotoxic Activities

A new carboline alkaloid, Trifiline D ( 1 ) and a new degraded diterpenoid, Trigoxyphin X ( 4 ) were isolated from the roots and stems of Trigonostemon lii. Their structures were elucidated by extensive spectroscopic analyses including 1D‐ and 2D‐NMR techniques. Compound 1 exhibited weak inhibitory activity against MCF‐7, A‐549, MGC‐803, and COLO‐205 with IC₅₀ values ranging from 27.4 to 35.4 μm .     

Design,Synthesis and Antifungal Evaluation of N‐Substituted‐1‐(3‐chloropyridin‐2‐yl)‐N‐(pyridin‐4‐yl)‐5‐(trifluoromethyl)‐1H‐pyrazole‐4‐carboxamide Derivatives

A series of 1‐(3‐chloropyridin‐2‐yl)‐5‐(trifluoromethyl)‐1H‐pyrazole‐4‐carboxamide derivatives which have di‐substituents on nitrogen were designed and synthesized. Bioassay results showed that all the synthetic compounds exhibited lower antifungal activities against Gibberella zeae, Cytospora mandshurica, and Fusarium oxysporum than T ₃ (14.7, 21.1, and 32.7 μg/mL), but some of them exhibited better activities against Botrytis cinerea, Phytophthora infestans, and Sclerotinia sclerotiorum than T ₃ (>200, >200, and >200 μg/mL); the EC₅₀ values of 7d and 7c against B. cinerea were 94.9 and 56.2 μg/mL, respectively. The EC₅₀ values of 7a , 7d , and 7c against S. sclerotiorum were 73.5, 78.7, and 68.5 μg/mL, respectively.     

A Facile One‐pot Synthesis and Anticancer Evaluation of Interesting Pyrazole and Pyrimidinthione via Heterocyclic Interconversion

Design and synthesis of new pyrazole, pyrimidinthione, and triazepinthione derivatives via heterocyclic ring opening of azacoumarin were promoted with grinding and ultrasonic reaction conditions. Efficient solventless one‐pot synthesis can be well progressed to afford the good yield of new heterocyclic products that were characterized by IR, ¹H‐NMR, MS, and microanalytical data. Anticancer evaluation for the synthesized compounds exhibited moderate to good cytotoxicity such as pyrazole derivatives 5 , 9 , and 14 that displayed best cytotoxic activities with IC₅₀ 8.16 ± 1.1, 7.02 ± 0.6, and 5.12 ± 0.41 μg/mL and 9.28 ± 0.7, 6.45 ± 0.9, and 5.85 ± 0.26 μg/mL for MCF‐7 and WI cells, respectively. Pyrimidine derivatives 6 , 11 , and 15 exhibited strong cytotoxicity with IC₅₀ 8.9 ± 0.62, 7.16 ± 0.5, and 7.72 ± 0.41 μg/mL against MCF‐7.     

Physiochemical properties and novel biological applications of Callistemon viminalis‐mediated α‐Cr2O3 nanoparticles

We report an eco‐friendly synthesis of α‐Cr₂O₃ nanoparticles (NPs) using Callistemon viminalis (Bottle Brush) flower extracts as an efficient reducing and capping agent. NPs of sizes 15 nm and 17 nm were synthesized by annealing them at 400°C and 500°C, respectively, which were characterized by X‐ray diffraction, UV–Vis, Fourier transform‐infrared, high‐resolution‐transmission electron microscopy/scanning electron microscopy, SAED, energy‐dispersive X‐ray spectroscopy and SQUID. Microplate‐based assay was used for examining antibacterial potential against 12 pathogenic bacterial strains, and their minimum inhibitory concentrations were calculated. MTT cytotoxic assay was accomplished on Leishmania tropica amastigotes and promastigotes, which revealed IC₅₀ values of 44 μg/ml and 10.56 μg/ml, respectively. An IC₅₀ value of 46.32 μg/ml was obtained for HepG2 cancer cells. Enzyme inhibition studies indicated good acetylcholinesterase, moderate butyrylcholinesterase and low alpha‐glucosidase inhibition. Hemolytic assay indicated hemocompatibility at low concentration. In addition, good DPPH radical scavenging and moderate reducing power and total antioxidant potential was revealed by α‐Cr₂O₃ NPs.     

Evaluation of newly synthesized derivatives of bis(hydrazine‐1‐carbothioamide) and their metal complexes synthesized in bulk and nano size as potent anticancer agents

A series of new metal complexes were synthesized in both bulk and nano size using green methods, starting with the reaction of (E)‐N′‐[(E)‐2‐bromobenzylidene]‐4‐oxo‐4‐(piperidin‐1‐yl)but‐2‐enehydrazide with thiosemicarbazide and different metal halides such as CuI·2H₂O, CuCl₂·2H₂O, CoCl₂·2H₂O, and ZnCl₂·2H₂O, and metal nitrate such as Ga(NO₃)₃·2H₂O. Structures of these metal complexes were confirmed using different spectroscopic methods, elemental analysis, electronic spectra, and microanalytical methods (scanning electron microscopy and transmission electron microscopy) for nano complexes. The distorted octahedral geometry for all complexes was suggested based on magnetic moments and electronic spectral studies. The cytotoxic activity of the compounds was investigated against human hepatocellular carcinoma (HepG2) and human colorectal carcinoma (HCT‐116) cell lines. Most tested compounds had higher inhibitory activity than the standard vinblastine drug. Interestingly, the nano‐sized Ga(III) complex 11 was the most potent compound against the two tested cell lines, with 50% inhibitory concentration (IC₅₀) of 2.56 μg/mL for HepG2, compared with the reference drug vinblastine (IC₅₀ 15.6 μg/mL), and IC₅₀ 4.64 μg/mL for HCT‐116, compared with the standard (IC₅₀ 13.9 μg/mL). The bioassay results helped us identify new potent and selective anticancer agents.     

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis,molecular geometry,theoretical studies and biological applications

Two mononuclear ruthenium complexes ( 1 and 2 ) with aroyl/acylthiourea as an ancillary ligand of type, [(η⁶‐p‐cymene)RuCl(L‐N,S)], where [ L1  = 2,4‐dichloro‐N‐(o‐tolylcarbamothioyl)benzamide] and L2  = N‐(phenylcarbamothioyl)cyclohexanecarboxamide] were synthesized and well characterized. The single crystal X‐ray diffraction studies revealed the coordination mode and the geometry of the complexes. The two complexes adopted general piano‐stool (three‐legged) geometry with a novel coordination mode of aroyl/acylthiourea through amide N (anionic) and thiocarbonyl S (neutral). This type of monobasic bidentate coordination of the aroyl/acylthiourea ligand was witnessed the first time around the metal ion. The coordination of the complexes was well explained through geometric parameters and frontier molecular orbital parameter values computed at the B3LYP/SDD level. The synthesized complexes were also screened for their antibacterial, antifungal, antioxidant and in vitro antiproliferative activities. Complexes exhibited good antimicrobial agents against various pathogens. The antioxidant activity of the complex 2 has shown most potent activity with IC₅₀ value of 48.55 ± 1.7 μM compared to the reference drug. In addition, the in vitro antiproliferative activity of the complex 2 showed excellent activity against HepG‐2 cell line with the IC₅₀ value of 24.30 ± 1.20 μM which is close to Doxorubicin standard drug.     

Inhibition of Pro-inflammatory Secreted Phospholipase A2 by Extracts from <Emphasis Type="Italic">Cynara cardunculus L</Emphasis>.

The aim of the present work was to evaluate the anti-inflammatory properties of Cynara cardunculus L. (Asteraceae) during its growth using various solvents such as n-hexane, dichloromethane, acetone, and methanol for air-dried leaves and stems. The anti-inflammatory activities of crude extracts were evaluated by measuring the inhibition potency of mammalian non-pancreatic phospholipases A2 (hG-IIA). The methanol and acetone extracts of leaves harvested in February exhibit potent inhibition of hG-IIA (IC₅₀ = 50 and 70 μg/ml, respectively). However, the acetone extract of stems harvested in December inhibits the hG-IIA with a lower IC₅₀ around 130 μg/ml. Fractionation on silica gel and hydrophobic gel of the methanol extract of leaves harvested in February increases the inhibitory effect, and the IC₅₀ reached 10 μg/ml.     

Trametes versicolor ethanol extract,a promising candidate for health–promoting food supplement

This study aimed to estimate antiradical, antioxidant (AO) and cytotoxic activities of the fungus Trametes versicolor ethanol fruiting body extract. The extract was found to effectively scavenge both O₂^?? and NO^? (29.62 and 52.48 μg/mL, respectively). It also showed a good AO activity in the polarographic HPMC assay (950%/mL). p-Hydroxybenzoic acid may be one of the responsible compounds for the afore-mentioned activities. The same extract also exhibited a concentration-dependent cytotoxicity against MCF-7 and HepG2 tumour cell lines reaching IC₅₀ values of 123.51 and 134.29 μg/mL, respectively with no cytotoxic activity against normal MRC-5 cells. Gentisic, syringic and protocatechuic acids may be among the bioactive principles for the observed cytotoxicity. Taken all together, T. versicolor ethanol extract can be considered as a promising candidate for development of health promoting food supplement.     

Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata

A carbazole-pyranocoumarin conjugate, carbazomarin B (1), and two carbazole alkaloids, 6-methoxymukonidine (2) and 2-hydroxy-3-methoxycarbazole (3), together with 27 known compounds (4–30), were isolated from the stems of Clausena excavata. Their structures have been elucidated by spectroscopic analyses. Compound 2 showed moderate cytotoxicity to HuCCA-1, MOLT-3 and HepG2 cancer cell lines with IC₅₀ values of 15.09–28.50 μg/mL, but none to A549 cell line. Heptaphylline (6) and nordentatin (23) were found to show moderate cytotoxic activity against HepG2 cell line with IC₅₀ values of 12.33 and 11.33, respectively, while clausine K (27) exhibited strong cytotoxicity with IC₅₀ value of 1.05 μg/mL, better than a standard drug (etoposide, IC₅₀ 13.40 μg/mL).     

Two New Flavonoids from Derris eriocarpa How

Two new flavonoids, 1 and 2 , together with two known flavonoids, tephrosin ( 3 ) and 12a‐hydroxy‐α‐toxicarol ( 4 ), were isolated from the whole herb of Derris eriocarpa How . The structures and absolute configurations of the new compounds were elucidated on the basis of their MS, NMR, and ECD data. The structures of the known compounds were established by extensive spectroscopic (MS, 1D‐ and 2D‐NMR) analyses and comparison with the literature data. All compounds were isolated from D. eriocarpa for the first time. Compound 3 showed modest inhibitory activities against the growth of human cancer cells HEL and A549 with the IC₅₀ values of 15.03 ± 0.62 and 13.27 ± 0.39 μm , respectively.     

Synthesis of thiazole clubbed pyrazole derivatives as apoptosis inducers and anti-infective agents

Fourteen N-[{(substituted-phenylthiazol-2-yl)-3-aryl-1H-pyrazol-4-yl}methylene]-5-substituted-thiazol-2-amine (5a-n) analogs were synthesized by the reaction of 3-aryl-1-(thiazol-2-yl)-1H-pyrazole-4-carbaldehyde and substituted thiazole amines. The structures of prepared compounds were delineated by elemental analysis, FT-IR and ¹H NMR spectra. These analogs were scrutinized for in vitro anti-infective and cytotoxic activities. Some thaizole clubbed pyrazole derivatives were assessed for their cytological changes in germ cells of Capra hircus by using histomorphological analysis, fluorescence assay and apoptosis quantification. Compound 5l having 4-NO₂ substituent induced the significant apoptosis in tested cells of Capra hircus. The results revealed that compounds 5c, 5e, 5k, and 5l have commendable antibacterial activity within MIC range of 62.5–250 μg/ml. Compound 5c emerged as a potent antimalarial compound by exhibiting IC₅₀ value of 0.23 μg/ml and compound 5j induced paralysis of Pherentima posthuma at 8.6 ± 1.94 min and death at 20 ± 5.04 min, respectively. Compound 5j revealed an excellent cytotoxicity at IC₅₀ value of 30.7 and < 10 μg/ml against MCF-7 and HeLa cells, respectively. Individually, compounds 5c, 5j and 5l could be considered as promising anti-infective and cytotoxic compounds.     

Synthesis of Substituted Quinolinyl Ether‐based Inhibitors of PI3K as Potential Anticancer Agents

A new strategy for the preparation of 8‐quinolyl ethers 3 ( a – g ), 5 ( a – g ), and 7 ( a – d ) was studied by copper (II)‐catalyzed methodology in the presence of Cs₂CO₃ and acetone–water mixture (1:1). Screening of quinolinyl‐8‐ethers was investigated against anticancer expressive studies to validate new chemical entity in medicinal chemistry. Approaches were evaluated against breast cancer (MCF‐7), skin cancer (G‐361), and colon cancer (HCT 116) cell lines. Inhibitory potentials against phosphoinositide‐3‐kinase (PI3K) enzyme responsible for cancer development have been evaluated by competitive ELISA studies. In PI3K assay, 3a – c were inactive (IC₅₀ > 5 μM), while 3e – g , 5a , 5c – e , 5g , 7a , and 7d showed a moderate activity (IC₅₀ ≥ 0.05 μM). Compounds ( 5b , 5f , 7b , and 7c ) showed significant activity (IC₅₀ < 1.0 μM); thus, their anticancer activities were carried out. Anticancer activity was found to be selective towards breast cancer (MCF‐7); 5b , 5f , 7b , and 7c showed predominant relative percentage activities of 74.12%, 79.04%, 72.56%, and 78.47%, with IC₅₀ values of 5b (2.27 ± 0.88 μM), 5f (1.38 ± 0.60 μM), 7b (2.64 ± 0.86 μM), and 7c (1.87 ± 0.68 μM) compared with the standard doxorubicin 73.14% inhibition (IC₅₀ = 1.98 ± 0.75 μM). Docking study also conducted to find out the binding interactions with p110α (PDB ID: 3T8M) enzyme. Compounds 5b , 5f , 7b , and 7c showed best docking score into the active site of PI3K 12.59, 10.51, 56.52, and 8.61 nM. Structure–activity relationship studies demonstrated that the synthesized compounds are the potential PI3K inhibitors to treat various cancer‐related diseases.