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Research in the field of metallodrugs is continually increasing. However, it is often limited by the poor solubility in water of the metal complexes. To try to overcome this problem, the two new ligands bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)thiocarbohydrazone (bis-TCH, Na2H4L1) and bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)carbohydrazone (bis-CH, Na2H4L2) were synthesized and characterized, both achieving high solubility in water. The speciation of the ligands and their coordinating behaviour towards the biologically relevant Cu(II) and Zn(II) ions were studied spectroscopically and potentiometrically, determining the pKas of the ligands and the formation constants of the complex species. The monometallic and bimetallic Cu(II) and Zn(II) complexes were isolated, and the single-crystal X-ray structure of [Cu2(NaHL1)(H2O)7].3.5H2O was discussed. Finally, preliminary studies of the in vitro cytotoxic properties of the new compounds were started on normal (Hs27) and cancer (U937) cell lines. bis-TCH was able to induce a growth inhibition effect between 40% and 45% in both cell lines; bis-CH did not produce a reduction in cell viability in Hs27 cells but revealed mild antiproliferative activity after 72 h of treatment in U937 cancer cells (GI50 = 46.5 ± 4.94 μg/mL). Coordination of the Cu(II) ions increased the toxicity of the compounds, while, in contrast, Zn(II) complexes were not cytotoxic. [ABSTRACT FROM AUTHOR]

Objective: In recent years, significant progress has been achieved in the treatment of patients with colorectal cancer, but in most cases, treatment is accompanied by the development of drug resistance. Recently discovered iron-dependent cell death, ferroptosis, provides promising therapeutic targets that might aid in reducing the recurrence rates. Methods: Derivatives of 3-hydroxyquinazoline were obtained by chemical synthesis and have a purity of at least 95%. In this study 2D cultivation of HCT-116 and DLD-1 cells, phase-contrast, and fluorescence microscopy were used. The ferroptotic cell death was identified by the level of lipid peroxidation using fluorescent indicator C11-BODIPY. Results and Discussion: We have examined the effect of 3-hydoxyquinazoline derivatives on ferroptosis induction in two colorectal cancer cell lines, HCT-116 and DLD-1. The level of lipid peroxidation in HCT-116 cells induced by some compounds approached the activity of the reference drug erastin. This scenario changed significantly when the ferroptosis induction was studied in DLD-1 cells. Fluorescence intensity induced by two 3-hydroxyquinazoline derivatives in DLD-1 cells exceeded those of erastin. Conclusions: The preliminary results suggest that three new compounds can be considered as antitumor agents for the treatment of colorectal cancer, particularly for the tumors with a highly malignant phenotype. The data obtained also indicate the prospects of further searching for ferroptosis inducers among 3-hydroxyquinazoline derivatives. [ABSTRACT FROM AUTHOR]

A large series of previously unknown isoxazole containing difluoroboron β‐diketonate has been designed and synthesized from the available starting compounds. The photophysical properties of obtained compounds were studied, and the effects of the substituents in aromatic and isoxazole cycles of the BF2 complexes on the fluorescence were investigated. The effect of solvatochromism were demonstrated. Cytotoxic activity against MCF‐7 (breast carcinoma), HCT‐116 (colon carcinoma), A549 (pulmonary carcinoma) and WI38 (fibroblasts from lung tissue) cell lines was tested and moderate toxicity in the concentration range of 10–100 μM was found for several compounds. [ABSTRACT FROM AUTHOR]

Phyllostachys heterocycla is well-known for its high diversity of bioactive metabolites, which are the reason for its various potential medical uses for which anticancer activity has been proven. Herein, Phyllostachys heterocycla extract was prepared in two different metallic nanoparticle formulas such as iron oxide nanoparticle-boron, and iron oxide nanoparticle-humic acid (Fe2O3 NP-B and Fe2O3 NP-HA) with average particle sizes of 12.25 nm and 15.80 nm, respectively. Phyllostachys heterocycla extract and the two nano-formulas were investigated to obtain their cytotoxic activity. The crude extract exhibited potent cytotoxic activity against the ovarian (OVCAR-3) cancer cell line, with IC50 values of 16.3 µg/mL. In comparison, the two nano-loaded forms displayed a much more promising cytotoxic activity with IC50 values of 0.9 µg/mL for Fe2O3 NP-HA, and 6.4 µg/mL for Fe2O3 NP-B. Additionally, NP-HA and NP-B showed potent cytotoxic activities against prostate (PC-3) and pancreatic (Panc1) cancer cell lines with IC50 values of 2.31, 6.3 µg/mL for Fe2O3 NP-HA, and 14.9, 16.8 µg/mL for Fe2O3 NP-B. For apoptosis investigation, Fe2O3 NP-HA induced total ovarian apoptotic cell death by a 87.34-fold change, and necrosis by 1.29-fold change. Regarding cell cycle analysis, Fe2O3 NP-HA-PHE arrested the cell proliferation of OVCAR-3 cells in S-phase, with an increased cell population at S-phase of 42.6%. Additionally, it confirmed the apoptosis mechanism by inhibiting the antiapoptotic gene and activating the proapoptotic gene markers. Moreover, upon continuation of our phytochemical investigation of the plant, additional chemical components of the crude extract of Phyllostachys heterocycla were isolated using various chromatographic techniques. As a result, six compounds were isolated. By using different spectroscopic data, the chemical structures of the pure isolated compounds were assigned as stigmasterol (1), glyceryl monobehenate (2), vanillic acid (3), ferulic acid (4), catechin (5), and thymidine (6). These isolated compounds were previously reported for their potent cytotoxic activities against panel of cancer cell lines including pancreatic cancer and prostate cancer cell lines (Ferulic acid), beside the anti-tumor potential against ovarian cell lines (Stigmasterol). In addition to the cytotoxic activity against human larynx carcinoma HepG-2 cell lines (Catechin), human breast cancer MCF7 (Thymidine), and human colon cancer cell line HT-29 (Vanillic acid). Which may explain the significant cytotoxic and anticancer properities of the crude extract of Phyllostachysheterocycla. [ABSTRACT FROM AUTHOR]

A phytochemical investigation on the 80% EtOH extract of the leaves of Paederia scandens (Lour.) Merr. resulted into the isolation of three undescribed iridoid glycosides, 10-O-trans-p-coumaroyl-(4R,6R)-3,4-dihydro-3α-methylthiopaederoside (1), 10-O-trans-feruloyl-(4S,6R)-3,4-dihydro-2′-O-3α-paederoside (2), and 10-O-trans-caffeoyl-paederosidic acid ethyl ester (3). The structures of the new compounds were elucidated by spectral methods such as 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, as well as high resolution mass spectrometry. The isolated compounds were tested in vitro for cytotoxic activity against five endocrine tumor cell lines. As a result, compound 1 exhibited some cytotoxicities against all the tested tumor cell lines with IC50 value less than 20.0 μM. [ABSTRACT FROM AUTHOR]

Triterpenoids of natural origin are of increasing interest due to their broad spectrum of biological activities. Previous studies on dipterocarpaceous plants have reported that they were valuable source of new active natural compounds. As part of an ongoing search for naturally occurring bioactive triterpenoids from Dipterocarpaceae, phytochemical investigation of Dipterocarpus costatus Gaertn. f. heartwood collected in Thailand was conducted. Seventeen triterpenoids (1 - 17) belonging to both 28-norlupane and dammarane series were isolated from the corresponding bioactive n -hexane extract. Among them, norlupane 1 was identified as previously undescribed and norlupane 2 was described for the first time from a natural source. Compound structures were elucidated by 1D/2D-NMR spectroscopy and mass (HRMS) spectrometry. All isolated molecules were tested for their cytotoxicity on two human colorectal carcinoma cell lines (i.e. HT-29 and HCT116), as well as for their antiplasmodial activity against chloroquine-resistant strain FcB1 of Plasmodium falciparum. Norlupanes 2 and 4 were shown to exhibit a good cytotoxic activity against HCT 116 (IC 50 =4.2 µM) and potent antiplasmodial activity (IC 50 =3.74 µM), respectively. [Display omitted] • To date, limited information is available regarding the phytochemistry of Dipterocarpus costatus. • Investigation was conducted on Dipterocarpus costatus heartwood collected in Thailand • Isolated triterpenoids belong to both 28-norlupane and dammarane series • Norlupane 2 has significant cytotoxic activity against HCT116 cell line (IC 50 =4.2 µM) • Norlupane 4 has potent activity against Plasmodium falciparum (IC 50 =3.74 µM). [ABSTRACT FROM AUTHOR]

Metallic nanoparticles created by ecologically friendly synthesis processes are becoming increasingly useful in a variety of applications. Because of their strong bioactive component qualities, biocompatible architectures, high stability, and low toxicity, green-produced selenium nanoparticles are particularly significant materials for various medicinal applications. Plants include a wealth of essential phytochemicals with therapeutic and medical capabilities. Pistachio vera L. (Siirt pistachio) is a seasonal fruit that is frequently consumed for its nutritional worth and health advantages. However, the outer colored skin of the P. vera (Siirt pistachio) fruit, which is not consumed, contains many biologically active compounds. In this study, plant-mediated synthesis of selenium nanoparticles (SeNPs) was successfully accomplished after adding the sodium selenite solution to the aqueous extract of P. vera colored skin waste. The synthesized Se NPs were characterized with UV–Vis, transmission electron microscopy (TEM), dynamic light scattering (DLS), zeta distribution, atomic force microscope (AFM), Fourier transform infrared spectrum (FTIR), thermogravimetric (TGA) and differential thermal analysis, X-ray diffraction (XRD), and energy-dispersive X-ray spectrum (EDX). Biogenic Pistacia vera (PV) PV-SeNPs were also tested for their ability to suppress the development of various pathogenic bacteria and cancerous cell lines. The UV-visible (UV–Vis) spectra revealed an absorption peak at 325 nm, which reflected the surface plasmon band. The significant selenium signal on the EDX spectrum at 1.5 keV confirmed the creation of Se NPs. The presence of several peaks on the FTIR spectrum of the aqueous extract of Pv and the nanoparticles indicated the presence of some important functional groups such as amines, carbonyl compounds, and phenols, which are important in facilitating the process of capping and bioreduction, as well as conferring stability to nanoparticles. The TEM microphotographs revealed that the nanoparticles were highly distributed, had a spherical morphological form, and were monodisperse below 10 nm. Biogenic Pv-SeNPs exhibited similar antimicrobial activity as standard antibiotics. However, it was determined that the cytotoxic activity of Se-NPs against cancer cell lines was quite high depending on the dose and time. As a result, the Pv-SeNPs are likely to be extremely beneficial in the pharmaceutical and cosmetic sectors, as well as in the food and cosmetic industries, in producing antimicrobial and/or anticancer medications. Graphical Abstract Of Green Synthesis, Characterization, And Biomedical Application of Pv-SeNPs [ABSTRACT FROM AUTHOR]

Herein, we report a synthesis and characterization of aziridine‐functionalized 1,3,5‐triazine derivatives. Electronic structure and the most preferable geometry of substances were calculated by DFT method. DNA binding investigations were conducted as part of the biomedicinal research as well as the cytotoxic activity of these compounds was evaluated using in vitro assays toward Huh‐7 and A549 cancer cell lines and HEK‐293 normal cell line. The results demonstrate that some of the synthesized compounds exhibit potent cytotoxic activity ([5‐[[4,6‐bis(aziridin‐1‐yl)‐1,3,5‐triazin‐2‐yl]amino]‐2,2‐dimethyl‐1,3‐dioxan‐5‐yl]methanol (1) and 4,6‐di(aziridine‐1‐yl)‐N‐(2,2,5‐trimethyl‐1,3‐dioxane‐5‐yl)‐1,3,5‐triazine‐2‐amine (9)), making them potential candidates for further development as anticancer agents. [ABSTRACT FROM AUTHOR]

Oleanolic acid, a naturally occurring triterpenoid compound, has garnered significant attention in the scientific community due to its diverse pharmacological properties. Continuing our previous work on the synthesis of oleanolic acid dimers (OADs), a simple, economical, and safe acetylation reaction was performed. The newly obtained derivatives (AcOADs, 3a–3n) were purified using two methods. The structures of all acetylated dimers (3a–3n) were determined based on spectral methods (IR, NMR). For all AcOADs (3a–3n), the relationship between the structure and the expected directions of pharmacological activity was determined using a computational method (QSAR computational analysis). All dimers were also tested for their cytotoxic activity on the SKBR-3, SKOV-3, PC-3, and U-87 cancer cell lines. HDF cell line was applied to evaluate the Selectivity Index of the tested compounds. All cytotoxic tests were performed with the application of the MTT assay. Finally, all dimers of oleanolic acid were subjected to DPPH and CUPRAC tests to evaluate their antioxidant activity. The obtained results indicate a very high level of cytotoxic activity (IC50 for most AcOADs below 5.00 µM) and a fairly high level of antioxidant activity (Trolox equivalent in some cases above 0.04 mg/mL). [ABSTRACT FROM AUTHOR]

AbstractThis paper describes the synthesis and in vitro biological evaluation of new compounds designated as 5(a-h) and 8(a-f). These compounds were synthesized by the reaction of thiazole derivative (3) or thiadiazole derivative (7) with urea and various aromatic aldehydes 4(a-h) in ethanol. The structures of the synthesized compounds were checked by IR,1H,13C NMR, and Mass spectroscopy. The antibacterial and antifungal activities of the compounds were evaluated against Escherichia coli (Gram-negative), Staphylococcus aureus (Gram-positive), and Candida albicans (fungus) using agar well diffusion, minimum inhibitory concentration (MIC), and minimum bactericidal/fungicidal concentration methods. The cytotoxic activities of these compounds against HT-29 and A-549 cancer cell lines were assessed in vitro by the MTT method. Our studies showed compounds 8c and 8f to have the most expressed antibacterial activity against S. aureus, while compounds 8c and 8d were the most potent against E. coli. Compounds 5h and 8e showed the highest antifungal activity against C. albicans, and compound 5f showed the most potent activity against the tested cancer cell lines. [ABSTRACT FROM AUTHOR]

AbstractA new sterol, aspersterol E (1), a newly discovered alkaloid, asperginine A (2), and five known compounds (3–7) were obtained from the endophytic fungus Aspergillus sp. S3 of Hibiscus tiliaceus Linn. The compounds were extracted from their fermentation products using silica gel, ODS C18, and semi-preparative HPLC. The structure of each compound was determined through spectroscopic analysis. All the obtained compounds (1–7) were evaluated for their cytotoxic activity against the mouse pre-gastric cancer cell line MFC by using the MTT assay. The IC50 values of compounds 1, 2, 3, and 5 were found to be 153.43 μM, 61.25 μM, 73.19 μM, and 181.69 μM respectively. [ABSTRACT FROM AUTHOR]

Recently, the growth of consumer demand for functional foods with potential nutritional and health benefits led to rapid growth of analytical tools for profiling of bioactive metabolites and assure quality. Bee propolis is one of the most important bee products owing to its myriad health value. As a gummy exudate produced in beehives after harvesting from different plant species, bee propolis contains bioactive secondary metabolites. The current study aims to profiling the chemical composition of propolis samples from Nigeria using HPLC–UV-ELSD and with the aid of NMR-based analysis for assignment of metabolites classes abundant in Nigerian propolis. Red Nigerian propolis samples were subjected to phytochemical analysis using HPLC–UV-ELSD and NMR. Further chromatographic separation of promising fractions was performed by column chromatography and size exclusion chromatography. Screening of the antitrypanosomal and cytotoxic activities against Trypanosoma brucei and human leukemia cell lines (U937), respectively, was performed. The performance of LC–MS permitted identification of the different components from which 13 compound were identified and allowed combination of fractions to afford 9 fractions from which two isoflavonoids were isolated and identified using 1D and 2D NMR analysis with MS as isosativan and Medicarpin. Red Nigerian propolis crude extract showed the highest inhibitory activity at 6.5 µg/ml compared to moderate activity for the isolated compounds with MIC of 7.6 µg/ml and 12.1 µg/ml for medicarpin and isosativan, respectively. Moreover, the fraction RN-6 from the total extract showed the potent cytotoxic effect with IC50 = 26.5 µg/ml compared to standard diminazen which showed IC50 = 29.5 µg/ml. [ABSTRACT FROM AUTHOR]

Eleven novel clerodane-type diterpenoids, grewiifopenes A–K (1–4 and 12–18), along with nine known compounds (5–11, 19, and 20) were purified from the dichloromethane extract of the twigs and stems of Casearia grewiifolia Vent. (Salicaceae). Their spectroscopic data, including the NMR, HRESIMS, and electronic circular dichroism calculations were employed to completely characterize and elucidate the chemical structures and absolute configurations. The clerodane diterpenoids possessing a 6-OH group and no substitution at C-7 exhibited greater cytotoxic activity than others, with their IC50 values ranging from 0.3 to 2.9 μM. Isocaseamembrin E (7) exhibited antibacterial activity against Staphylococcus aureus, while isocaseamembrin E (7), corymbulosin X (8), caseargrewiin A (9), kurzipene A (10), and balanspene F (11) exhibited antibacterial activity against Bacillus cereus. [ABSTRACT FROM AUTHOR]

Simple Summary: Inula viscosa (synonymous of Dittrichia viscosa) is a plant used in traditional Mediterranean and Middle Eastern medicine to manage various illnesses. While it has shown anticancer effects against various cancer cell lines, its impact on lung cancer has not been under extensive study. This research explored the potential of the methanolic and aqueous extracts and a terpenoid-rich fraction of I. viscosa leaves and stems against human lung cancer cells. We found that the methanolic extract of I. viscosa leaves was particularly effective in reducing the viability of lung cancer cells in vitro, and other cancer cell types, without affecting normal cells. The terpenoid-rich fraction demonstrated anticancer properties by attenuating the levels of proliferation marker proteins, activating the intrinsic apoptosis pathway, and inhibiting cell migration. GC/MS analysis revealed that the terpenoid-rich fraction encompasses several metabolites that can substantiate its biological activities. Inula viscosa is a widely used plant in traditional Mediterranean and Middle Eastern medicine for various illnesses. I. viscosa has been shown to have anticancer effects against various cancers, but its effects against lung cancer have been under limited investigation. At the same time, I. viscosa is rich in terpenoids whose anti-lung cancer effects have been poorly investigated. This study aimed to examine the potential anticancer properties of methanolic and aqueous extracts of stems and leaves of I. viscosa and its terpenoid-rich fraction against human lung cancer A549 cells. Results showed that the methanolic extracts of I. viscosa had significantly higher polyphenol and flavonoid content and radical scavenging capacity than the aqueous extracts. In addition, leaves methanolic extracts (IVLM) caused the highest reduction in viability of A549 cells among all the extracts. IVLM also reduced the viability of human ovarian SK-OV-3, breast MCF-7, liver HepG2, and colorectal HCT116 cancer cells. A terpenoid-rich I. viscosa fraction (IVL DCM), prepared by liquid-liquid separation of IVLM in dichloromethane (DCM), displayed a substantial reduction in the viability of A549 cells (IC50 = 27.8 ± 1.5 µg/mL at 48 h) and the panel of tested cancerous cell lines but was not cytotoxic to normal human embryonic fibroblasts (HDFn). The assessment of IVL DCM phytochemical constituents using GC-MS analysis revealed 21 metabolites, highlighting an enrichment in terpenoids, such as lupeol and its derivatives, caryophyllene oxide, betulin, and isopulegol, known to exhibit proapoptotic and antimetastatic functions. IVL DCM also showed robust antioxidant capacity and decent polyphenol and flavonoid contents. Furthermore, Western blotting analysis indicated that IVL DCM reduced proliferation (reduction of proliferation marker Ki67 and induction of proliferation inhibitor proteins P21 and P27), contaminant with P38 MAP kinase activation, and induced the intrinsic apoptotic pathway (P53/BCL2/BAX/Caspase3/PARP) in A549 cells. IVL DCM also reduced the migration of A549 cells, potentially by reducing FAK activation. Future identification of anticancer metabolites of IVL DCM, especially terpenoids, is recommended. These data place I. viscosa as a new resource of herbal anticancer agents. [ABSTRACT FROM AUTHOR]

Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is a continuous interest in the synthesis of these compounds. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological properties. Three routes are followed for the synthesis of lamellarins. Initially, pyrrole derivatives are the starting or intermediate compounds, and then they are fused to isoquinoline or a coumarin moiety. Second, isoquinoline is the starting compound fused to an indole moiety. In the last route, coumarins are the starting compounds, which are fused to a pyrrole moiety and an isoquinoline scaffold. The synthesis of isolamellarins, azacoumestans, isoazacoumestans, and analogues is also described. The above synthesis is achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, and lactonization reactions. The title compounds exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, and anti-inflammatory activities. [ABSTRACT FROM AUTHOR]

The prevalence of cancer is so high globally that it is imperative to identify effective treatments. The use of bee products in the field of cancer therapeutics has gained significant attention as a promising alternative. Female worker bees (Apis mellifera) produce bee venom, which contains a complex array of biologically active compounds, including enzymes and peptides. Bee venom exhibits a range of biological activities with potential human health benefits, which vary across bee species and geographic locations. The objective of this study was to investigate the cytotoxicity of Turkish bee venom for the first time on some of the selected cancer cell lines. Bee venom was collected and resuspended in water and ethanol. The study analyzed both forms of Turkish bee venom for major peptides and proteins using HPLC-VWD and SDS-PAGE. The major components identified were apamin, melittin, phospholipase A2, and hyaluronidase. Cytotoxic activities were evaluated on eight distinct cell lines (seven cancerous cells and one control) using MTT assays. The Turkish bee venom demonstrated cytotoxicity with 48-hour IC50 values of 14.8 ± 0.6, 5.7 ± 0.2, 8.1 ± 0.1, 7.1 ± 0.1, 8.5 ± 0.2, 7.2 ± 0.1, 7.9 ± 0.1, and 8.0 ± 0.1 µg/mL for Phoenix-AMPHO (CRL-3213), PC-3, Huh-7, Caco-2, HT-29, SW-48, CARM-L12 TG3, and A-673, respectively. The 72-hour IC50 values were 8.2 ± 0.2, 4.5 ± 0.3, 7.1 ± 0.1, 6.4 ± 0.1, 6.0 ± 0.3, 7.2 ± 0.1, 2.1 ± 0.1, and 6.0 ± 0.2 µg/mL, respectively. In conclusion, the study demonstrated that both forms of Turkish bee venom exhibited significant cytotoxic effects on the analyzed cancer cells. The cell lines CARM-L12 TG3, PC-3, and A-673 exhibited the most pronounced responses to the bee venom. [ABSTRACT FROM AUTHOR]

Chemical investigations of the termite-associated Streptomyces tanashiensis BYF-112 resulted in the discovery of four novel alkaloid derivatives: vegfrecines A and B (1 and 2), exfoliazone A (3), and venezueline H (7), in addition to nine known metabolites (4 − 6 , 8 − 13). The structures of these compounds were elucidated through comprehensive spectroscopic analysis and comparison with existing literature data. Antibacterial assays revealed that viridomycin A (11) exhibited potent antibacterial activity against Staphylococcus aureus , with a zone of inhibition (ZOI) of 12.67 mm, in comparison to a ZOI of 17.67 mm for the positive control gentamicin sulfate. Viridomycin A (11) showed moderate activity against Micrococcus tetragenus and Pseudomonas syringae pv. actinidae , with ZOI values of 15.50 and 14.33 mm, respectively, which were inferior to those of gentamicin sulfate (34.67 and 24.00 mm). Viridomycin F (12) also exhibited moderate antibacterial effects against S. aureus , M. tetragenus , and P. syringae pv. actinidae , with ZOI values of 8.33, 16.50, and 10.83 mm, respectively. Cytotoxicity assays demonstrated that viridobruunine A (5), exfoliazone (6), viridomycin A (11), and X-14881E (13) exhibited significant cytotoxicity against human malignant melanoma (A375), ovarian cancer (SKOV-3), and gastric cancer (MGC-803) cell lines, with IC 50 values ranging from 4.61 to 19.28 μmol·L−1. Furthermore, bioinformatic analysis of the complete genome of S. tanashiensis suggested a putative biosynthetic gene cluster (BGC) responsible for the production of compounds 1−12. These findings indicate that the secondary metabolites of insect-associated S. tanashiensis BYF-112 hold promise as potential sources of novel antibacterial and anticancer agents. [ABSTRACT FROM AUTHOR]

Chemical investigations of higher plants, with particular attention paid to their steroidal glycosides, present a promising approach for generating anti-cancer agents from natural products. We conducted a systematic phytochemical investigation of nine higher plants—whole plants and rhizomes of Convallaria majalis, whole plants of Agave utahensis, roots of Adonis amurensis, seeds of Adonis aestivalis, bulbs of Bessera elegans, bulbs of Fritillaria meleagris, seeds of Digitalis purpurea, underground parts of Yucca glauca, and bulbs of Lilium pumilum—which led to the discovery of novel steroidal glycosides. The structures of these new constituents were determined based on spectroscopic data and chemical transformations. The identification of the monosaccharides including their absolute configurations was carried out by direct HPLC analysis of their hydrolysates using an optical rotation detector. Cytotoxicity of the isolated steroidal glycosides was evaluated against various tumor cells (A549, ACHN, HepG-2, HL-60, HSC-2, HSC-3, HSC-4, HSG, and SBC-3) and normal cells (Fa2 N-4, HK-2, and TIG-3 cells). Certain steroidal glycosides exhibit selective cytotoxicity and synergistic effects, making them potential lead compounds for use as anti-cancer agents. We document the isolation of 139 steroidal glycosides from higher plants and assessment their cytotoxic activities. [ABSTRACT FROM AUTHOR]

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Twelve compounds, including four undescribed cytochalasins, xylariachalasins A–D (1–4), four undescribed polyketides (5–8), and four known cytochalasins (9–12), were isolated from the mangrove endophytic fungus Xylaria arbuscula QYF. Their structures and absolute configurations were established by extensive spectroscopic analyses (1D and 2D NMR, HRESIMS), electronic circular dichroism (ECD) calculations, 13C NMR calculation and DP4+ analysis, single-crystal X-ray diffraction, and the modified Mosher ester method. Compounds 1 and 2 are rare cytochalasin hydroperoxides. In bioactivity assays, Compound 2 exhibited moderate antimicrobial activities against Staphylococcus aureus and Candida albicans with MIC values of 12.5 μM for both Compound 10 exhibited significant cytotoxic activity against MDA-MB-435 with an IC50 value of 3.61 ± 1.60 μM. [ABSTRACT FROM AUTHOR]

A range of new fluorinated derivatives of benzophenone analogs were developed and assessed on the human MDA‐MB‐231 triple‐negative breast cancer cell line and human cervical carcinoma cell line KB‐3‐1 for cytotoxic and anti‐proliferative effects. Synthesized derivatives were characterized by 1H NMR, 13C NMR, FTIR, HRMS, and XRD spectroscopy. Compounds 6 a and 7 a had ~2.1 and ~13‐fold more cytotoxic activity against the KB‐3‐1 cell line than the positive control, gemcitabine. Malononitrile‐modified fluorinated benzophenone derivatives 6 b and 7 b exhibited outstanding cytotoxicity against the KB‐3‐1 cell line, outperforming the standard reference by ~3.6 and ~13.5 times, respectively. Similarly, compounds 6 a, and 7 a exhibited ~1.2 and ~2.5 fold accurate cytotoxic activity against the MDA‐MB‐231 breast cancer cell line compared to a standard reference. Whereas, compounds 6 b and 7 b exhibited ~2.2 and ~2.8 fold accurate cytotoxic activity compared to a reference standard. The experimental results demonstrated that out of eight novel compounds, compound 7 b had greater cytotoxic activity than the standard reference against the cervical cancer cell line KB‐3‐1 and the breast cancer MDA‐MB‐231. Molecular docking investigation was used to examine the expected binding affinity and potential binding poses of the produced compounds. [ABSTRACT FROM AUTHOR]

Endophytic fungi from Aglaia argentea have indicated the prospective to produce secondary metabolites with unique activities, making them promising candidates for anticancer drug development. This study aimed to investigate the secondary metabolites produced by Lasiodiplodia theobromae BPPCA144, isolated from A. argentea. L. theobromae BPPCA144 was found to produce seven compounds: 2-phenylethanol (1), tyrosol (2), 2-(4-hydroxyphenyl)acetic acid (3), (-)-mellein (4), colletopeptide B (5), botryorhodine A (6), and (4R*,6R*)-4-hydroxy-6-n-propyl-1-oxacyclohexan-2-one (7). These compounds were isolated using vacuum liquid and radial chromatography, and their chemical structures were elucidated through 1D-NMR, 2D-NMR analysis, compared with previously reported spectral data. Notably, compounds (5) and (7) were identified as original from L. theobromae. Among the tested compounds, compound (2) exhibited the strongest activity against MCF-7 breast cancer cells. However, compounds (1, 3, 5 and 7) showed insufficient activity against CV-1 cell lines (normal kidney fibroblast cells). [ABSTRACT FROM AUTHOR]

Hinterhubera imbricata Cuatrec. et Aristeg belongs to Asteraceae family and it is one of the six endemic species that grows in Venezuela Andean. Present investigation aimed to determine the chemical composition of the essential oil of Hinterhubera imbricata and to evaluate the cytotoxic activity in human tumor cell lines from MCF-7 (breast carcinoma without over-expression of the HER2/cerb-2), PANC-1 (pancreatic adenocarcinoma ductal type) and SKBr3 (breast carcinoma, in which the HER2/cerb-2 gene is overexpressed). Results indicated that essential oil was mainly composed of monoterpenes being α-phellandrene, α-pinene, β-phellandrene and p-cymene as major components. Cytotoxic analysis revealed that this essential oil exhibited antitumor activity in all human tumor lines tested being more cytotoxic for the pancreatic cancer tumor line. To the best of our knowledge there are no published studies regarding either the genus Hinterhubera or the species Hinterhubera imbricata, thus, present investigation is considered as a contribution to the genus Hinterhubera study. [ABSTRACT FROM AUTHOR]

Lapachol (2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione) is a 1,4-naphthoquinone-derived natural product that presents numerous bioactivities and was shown to have cytotoxic effects against several human tumor cells. Indium(III) complexes with a variety of ligands also exhibit antineoplastic activity. Indium(III) complexes [In(lap)Cl2].4H2O (1), [In(lap)2Cl(Et3N)] (2), [In(lap)3]·2H2O (3) [In(lap)(bipy)Cl2] bipy = 2,2′-bipyridine (4) and [In(lap)(phen)Cl2] phen = 1,10-phenanthroline (5) were obtained with 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione (lapachol). Crystal structure determinations for (4) and (5) revealed that the indium(III) center is coordinated to two O atoms from lapachol, two N atoms from 1,10-phenanthroline or 2,2′-bipyridine, and two chloride anions, in a distorted octahedral geometry. Although both complexes (4) and (5) interacted with CT-DNA in vitro by an intercalative mode, only 5 exhibited cytotoxicity against MCF-7 and MDA-MB breast tumor cells. 1,10-phenanthroline and complex (5) presented cytotoxic effects against MCF-7 and MDA-MB cells, with complex (5) being threefold more active than 1,10-phenanthroline on MCF-7 cells. In addition, complex (5) significantly reduced the formation of MDA-MB-231 colonies in a clonogenicity assay. The foregoing results suggest that further studies on the cytotoxic effects and cellular targets of complex (5) are of utmost relevance. [ABSTRACT FROM AUTHOR]

Cancer is the second leading cause of death in the world following cardiovascular disease. Its treatment, including radiation therapy and surgical removal of the tumour, is based on pharmacotherapy, which prompts a constant search for new and more effective drugs. There are high costs associated with designing, synthesising, and marketing new substances. Drug repositioning is an attractive solution. Fluoroquinolones make up a group of synthetic antibiotics with a broad spectrum of activity in bacterial diseases. Moreover, those compounds are of particular interest to researchers as a result of reports of their antiproliferative effects on the cells of the most lethal cancers. This article presents the current progress in the development of new fluoroquinolone derivatives with potential anticancer and cytotoxic activity, as well as structure–activity relationships, along with possible directions for further development. [ABSTRACT FROM AUTHOR]

Cu2XSnS4 (CXTS; X: Zn, Mn or Co) nanorods (NRs) were prepared by a simple hot-injection method and their cytotoxic activities on human breast adenocarcinoma (MCF-7), metastatic melanoma (451Lu) and embryonic kidney (HEK-293) cell lines were investigated for the first time. The antibacterial activities of these nanoparticles on both gram-positive (S. aureus) and gram-negative (E. coli) pathogenic bacteria as well as their DPPH (2,2-diphenyl-1- picrylhydrazyl) scavenging activities were evaluated. The structural characterizations show that the obtained nanoparticles have the same crystal structure and are shaped as nanorods with an average 10–40 nm edge length. The data obtained in cytotoxicity studies revealed that the synthesized CXTS NRs have a significant inhibition effect, especially on cancer cell lines (MCF-7 and 451Lu), in a dose-dependent manner over a period of 24 h, demonstrating their potential for use as anticancer agents. In addition, the findings indicate that the synthesized nanorods possess strong antibacterial properties against the pathogenic microorganisms tested and display a marked antioxidant effect through efficient elimination of DPPH activity. This comprehensive study sheds light on the creation and development of CXTS NRs as promising versatile agents in various biomedical and environmental applications such as cancer therapy, antimicrobial strategies and the neutralization of free radicals. [ABSTRACT FROM AUTHOR]

Two new iridoid glycosides, maytenhoiridosides A (1) and maytenhoiridosides B (2), along with three known compounds (3 – 5), were isolated from the branches of Maytenus hookeri. Their chemical structures were elucidated by HR-ESI-MS, 1D and 2D-NMR spectra, acid hydrolysis analysis, and comparison with literature data. Among the isolated compounds, compound 5 exhibited significant cytotoxic activity against the HCT-116, SKOV3 and SK-Hep-1 cells, with IC 50 values of 9.49±1.40, 34.66±1.48 and 12.66±3.32 µM, respectively, while the others showed weak or no activity at 50 μM. [Display omitted] • Two new iridoid glycosides were isolated from Maytenus hookeri. • The structures were confirmed by extensive spectroscopic analyses. • Compound 5 exhibited significant cytotoxic activities. [ABSTRACT FROM AUTHOR]

Two undescribed polyacetylated 18-norspirostanol saponins, trilliumosides J (1) and 21-deoxyepitrillenoside C (2), a novel resveratrol aneuploid, 3a,3b-dimethoxyhopeachinol B (3) along with four known steroidal saponins (4–7), were isolated from the 70% EtOH extract of the roots and rhizomes of Trillium camschatcense. The structures of isolated compounds were elucidated by spectroscopic analysis and chemical degradation. Compounds 1,3 and 4 had potential cytotoxic activity against MCF-7, with IC50 values 86.38 ± 2.59 μM, 56.20 ± 1.57 μM and 45.70 ± 0.63 μM. [ABSTRACT FROM AUTHOR]

The soil-derived fungus Talaromyces thailandensis PSU-SPSF059 produced one new vermistatin derivative, talarostatin, and seven known compounds including two vermistatins, two chrodrimanins, two diphenyl ethers and one penicillide derivative. Extensive spectroscopic analysis was performed to identify their structures. The absolute configuration of talarostatin was determined by comparing the experimental and calculated electronic circular dichroism data. The antimicrobial and cytotoxic activities of the isolated secondary metabolites were also evaluated. [ABSTRACT FROM AUTHOR]

Tarek A Ahmed,1,2 Ghada A Milibary,1 Alshaimaa M Almehmady,1 Amerh A Alahmadi,1 Ehab MM Ali,3 Khalid M El-Say1 1Department of Pharmaceutics, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia; 2Centre for Artificial Intelligence in Precision Medicine, King Abdulaziz University, Alsulaymanyah, Jeddah, 21589, Saudi Arabia; 3Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi ArabiaCorrespondence: Tarek A Ahmed, Department of Pharmaceutics, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia, Tel +96626400000 ext 22250, Email tabdelnapy@kau.edu.saBackground: This study investigates the influence of various formulation parameters on the characteristics of hinokitiol-loaded phytosomes and evaluates their anticancer potential against breast cancer cells.Materials and Methods: Phytosomal nanoparticles were prepared and characterized for size, zeta potential, and entrapment efficiency. Morphological analysis was conducted using optical microscopy and transmission electron microscopy (TEM). The solubility of hinokitiol at different pH levels was determined, and the in vitro release profile of the optimized phytosomes was assessed. Cytotoxicity assays were performed to evaluate the anticancer efficacy against breast cancer cell lines, and apoptosis induction was examined using Annexin V/propidium iodide staining. Cell cycle analysis was conducted to assess the impact on cell cycle progression.Results: The optimized phytosomes demonstrated a size range of 138.4 ± 7.7 to 763.7 ± 15.4 nm, with zeta potentials ranging from − 10.2 ± 0.28 to − 53.2 ± 1.06 mV and entrapment efficiencies between 29.161 ± 1.163% and 92.77 ± 7.01%. Morphological characterization confirmed uniformity and spherical morphology. Hinokitiol solubility increased with pH, and the release from the optimized phytosomes exhibited sustained patterns. The formulated phytosomes showed superior cytotoxicity, with lower IC50 values compared to pure hinokitiol. Treatment induced significant apoptosis and cell cycle arrest at the G2/M and S phases.Conclusion: Hinokitiol-loaded phytosomes demonstrate promising anticancer efficacy against breast cancer cells, highlighting their potential as targeted therapeutic agents for breast cancer therapy.Keywords: hinokitiol, phytosomes, cytotoxic activity, breast cancer, apoptosis, cell cycle

Abstract Recently, the growth of consumer demand for functional foods with potential nutritional and health benefits led to rapid growth of analytical tools for profiling of bioactive metabolites and assure quality. Bee propolis is one of the most important bee products owing to its myriad health value. As a gummy exudate produced in beehives after harvesting from different plant species, bee propolis contains bioactive secondary metabolites. The current study aims to profiling the chemical composition of propolis samples from Nigeria using HPLC–UV-ELSD and with the aid of NMR-based analysis for assignment of metabolites classes abundant in Nigerian propolis. Red Nigerian propolis samples were subjected to phytochemical analysis using HPLC–UV-ELSD and NMR. Further chromatographic separation of promising fractions was performed by column chromatography and size exclusion chromatography. Screening of the antitrypanosomal and cytotoxic activities against Trypanosoma brucei and human leukemia cell lines (U937), respectively, was performed. The performance of LC–MS permitted identification of the different components from which 13 compound were identified and allowed combination of fractions to afford 9 fractions from which two isoflavonoids were isolated and identified using 1D and 2D NMR analysis with MS as isosativan and Medicarpin. Red Nigerian propolis crude extract showed the highest inhibitory activity at 6.5 µg/ml compared to moderate activity for the isolated compounds with MIC of 7.6 µg/ml and 12.1 µg/ml for medicarpin and isosativan, respectively. Moreover, the fraction RN-6 from the total extract showed the potent cytotoxic effect with IC50 = 26.5 µg/ml compared to standard diminazen which showed IC50 = 29.5 µg/ml.

Abstract Eleven novel clerodane-type diterpenoids, grewiifopenes A–K (1–4 and 12–18), along with nine known compounds (5–11, 19, and 20) were purified from the dichloromethane extract of the twigs and stems of Casearia grewiifolia Vent. (Salicaceae). Their spectroscopic data, including the NMR, HRESIMS, and electronic circular dichroism calculations were employed to completely characterize and elucidate the chemical structures and absolute configurations. The clerodane diterpenoids possessing a 6-OH group and no substitution at C-7 exhibited greater cytotoxic activity than others, with their IC50 values ranging from 0.3 to 2.9 μM. Isocaseamembrin E (7) exhibited antibacterial activity against Staphylococcus aureus, while isocaseamembrin E (7), corymbulosin X (8), caseargrewiin A (9), kurzipene A (10), and balanspene F (11) exhibited antibacterial activity against Bacillus cereus. Graphical Abstract

In order to study the chemical constituents from Chloranthus henryi and their antitumor activities in vitro. The chemical constituents of ethyl acetate fraction, extracted with 95% ethanol from C. henryi were isolated and purified by silica gel column chromatography, reversed phase column chromatography, Sephadex LH-20 column chromatography and preparation liquid chromatography, and their structures were identified by the physicochemical properties, spectral data combined with relevant literatures. The cytotoxic activities of these compounds were evaluated by MTT method. The results were as follows: (1) Twelve compounds were isolated and identified as pipercyclobutanamide C (1), chololactone A (2), sarcanolide B (3), oxacol A (4), chloramultiol D (5), chlorasessilifol B (6), chlorajaponol (7), tianmushanol (8), spicachlorantins B (9), spicachlorantins A (10), serrachlorin A (11), chloramultiols A (12). Among them, Compound 1 was identified as a new compound, and except for Compound 8, all the other compounds were isolated from the C. henryi for the first time. (2) The cytotoxic activity test results showed that only compounds 2 and 7 had good inhibitory effects on HeLa cells in vitro, while the other compounds showed no inhibition effects. The IC50 of the two compounds were (4.50±0.27) μmol·L-1 and (4.25±0.08) μmol·L-1 respectively. In conclusion, the study enriches the chemical constituents of C. henryi, and provides a reference for the further exploration and utilization of this Chloranthus herb plants.

To study the chemical constituents of Ludwigia octovalvis, the 80% ethanol extract from L. octovalvis was isolated by silica gel, Sephadex LH-20, Flash C18 and semi-preparative liquid chromatography, and the structures of obtained compounds were identified by physicochemical properties and spectral data. The cytotoxic activity of the isolates were evaluated by MTS method. The results were as follows: (1) Twenty compounds were isolated from L. octovalvis, and their structures were identified as (-)-lyoniresinol (1), 8,8′-bisdihydrosiringenin (2), 5-methoxy-(-)-isolariciresinol (3), (-)-isolariciresinol (4), 3,4′-di-O-methylellagic acid (5), 3,3′,4′-tri-O-methylellagic acid (6), 1,3,6-tri-O-galloyl-β-glucospyranose (7), corilagin (8), methyl gallate (9), ethyl gallate (10), terminaliate A (11), syringic acid (12), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (13), luteolin (14), kaempferol (15), 5,8-dihydroxy-7-methoxyflavone (16), nobiletin (17), tangeretin (18), α-tocopherolquinone (19), 5-O-(E)-p-coumaroyl quinic acid ethyl ester (20). Compounds 1-5, 7, 8, 11, 13, 16-20 were isolated from Ludwigia for the first time. Compounds 6, 9, 10, 12, 15 were isolated from this plant for the first time. (2) Compound 19 showed inhibitory activity against the leukemia HL-60 with the IC50 value of 10.31 μmol·L-1. Compounds 6-8, 19 showed inhibitory activity against the lung cancer cells A549 with the IC50 values of 25.82, 42.05, 36.94, 17.54 μmol·L-1, respectively. Compounds 6, 7, 11, 14, 19 showed inhibitory activity against the liver cancer SMMC-7721 with the IC50 values of 24.24, 26.35, 26.51, 33.34, 20.44 μmol·L-1, respectively. Compounds 6, 19 showed inhibitory activity against the breast cancer MDA-MB-231 with the IC50 values of 34.91, 21.13 μmol·L-1, respectively. Compounds 6, 7, 19 showed inhibitory activity against the colon cancer SW480 with the IC50 values of 36.03, 39.97, 5.52 μmol·L-1, respectively. The results of this study enrich the chemical constituents of L. octovalvis and provide a basis for the development of anti-tumor activity.

Alkaloid-based urea derivatives were produced with high yield through the reaction of anabasine and cytisine with isoxazolylphenylcarbamates in boiling benzene. Their antitumor activity, in combination with the commonly used five anticancer drugs, namely cyclophosphane, fluorouracil, etoposide, cisplatin, ribomustine with different mechanisms of action, was investigated. Based on the quantum chemical calculations data and molecular docking, hypotheses have been put forward to explain their mutual influence when affecting C6 rat glioma model cells. [ABSTRACT FROM AUTHOR]

AbstractA chemical investigation on the roots of Aconitum nagarum afforded two undescribed C19-diterpenoid alkaloids nagarumines D and E (1 and 2). The structures of the new compounds were elucidated by spectral methods such as 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, as well as HR-ESI-MS. The two isolated alkaloids were tested in vitro for cytotoxic activity against five gastric tumor cell lines. Consequently, compound 2 exhibited some cytotoxicities against several human cancer cell lines with IC50 value less than 20.0 μM. [ABSTRACT FROM AUTHOR]

Cancer represents one of the most significant health challenges currently facing humanity, and plant-derived antitumour drugs represent a prominent class of anticancer medications in clinical practice. Isovaleryl sucrose esters, which are natural constituents, have been identified as having potential antitumour effects. However, the mechanism of action remains unclear. In this study, 12 isovaleryl sucrose ester components, including five new (1–5) and seven known compounds (6–12), were isolated from the roots of Atractylodes japonica. The structures of the compounds were elucidated using 1D and 2D-NMR spectroscopy, complemented by HR-ESI-MS mass spectrometry. The cytotoxic activities of all the compounds against human colon cancer cells (HCT-116) and human lung adenocarcinoma cells (A549) were also evaluated using the CCK8 assay. The results demonstrated that compounds 2, 4, and 6 were moderately inhibitory to HCT-116 cells, with IC50 values of 7.49 ± 0.48, 9.03 ± 0.21, and 13.49 ± 1.45 μM, respectively. Compounds 1 and 6 were moderately inhibitory to A549, with IC50 values of 8.36 ± 0.77 and 7.10 ± 0.52 μM, respectively. Molecular docking revealed that compounds 1–9 exhibited a stronger affinity for FGFR3 and BRAF, with binding energies below −7 kcal/mol. Compound 2 exhibited the lowest binding energy of −10.63 kcal/mol to FGFR3. We screened the compounds with lower binding energies, and the protein-ligand complexes already obtained after molecular docking were subjected to exhaustive molecular dynamics simulation experiments, which simulated the dynamic behaviour of the molecules in close proximity to the actual biological environment, thus providing a deeper understanding of their functions and interaction mechanisms. The present study provides a reference for the development and use of iso-valeryl sucrose esters in the antitumour field. [ABSTRACT FROM AUTHOR]

Metabolic alterations are increasingly recognized as important aspects of colorectal cancer (CRC), offering potential avenues for identifying therapeutic targets. Previous studies have demonstrated the cytotoxic potential of bamboo leaf extract obtained from Guadua incana (BLEGI) against HCT-116 colon cancer cells. However, the altered metabolic pathways in these tumor cells remain unknown. Therefore, this study aimed to employ an untargeted metabolomic approach to reveal the metabolic alterations of the endometabolome and exometabolome of HCT-116 cells upon exposure to BLEGI treatment. First, a chemical characterization of the BLEGI was conducted through liquid chromatography coupled with mass spectrometry (LC-MS). Next, we assessed cell viability via MTT and morphological analysis using an immunofluorescence assay against colon cancer cells, and anti-inflammatory activity using an LPS-stimulated macrophage model. Subsequently, we employed LC-MS and proton nuclear magnetic resonance (1H-NMR) to investigate intra- and extracellular changes. Chemical characterization primarily revealed the presence of compounds with a flavone glycoside scaffold. Immunofluorescence analysis showed condensed chromatin and subsequent formation of apoptotic bodies, suggesting cell death by apoptosis. The results of the metabolomic analysis showed 98 differential metabolites, involved in glutathione, tricarboxylic acid cycle, and lipoic acid metabolism, among others. Additionally, BLEGI demonstrated significant nitric oxide (NO) inhibitory capacity in macrophage cells. This study enhances our understanding of BLEGI’s possible mechanism of action and provides fresh insights into therapeutic targets for treating this disease. [ABSTRACT FROM AUTHOR]

The leaves of Ilex paraguariensis (known as Yerba mate), used as a popular beverage, are a very well-recognized plant material with various biological activities, including analeptic (because of caffeine), anti-obesity (phenolics, saponins), antimicrobial, and antiviral (phenolics, saponins). Here, the chemical compositions of the leaves of two European Ilex species (× meserveae and aquifolium) with three varieties each were investigated. The terpenoid, saponin, and polyphenolic fractions were submitted for LC-MS or GC-MS analysis against a standard Mate leaf. In addition, the aroma profiles of all the species were analysed using HS-SPME-Arrow prior to GC-MS analysis. All fractions were subjected to antiviral and cytotoxic assays. We found 86 compounds in all accessions, with limonene, linalool, and p-cymene being predominant. There were minor similarities between the volatile compositions of the European and South American species. We found ursolic and oleanolic acid to be the main compounds in the terpenoid fraction. Mono-caffeoylquinic acids and di-caffeoylquinic acids were the main constituents of the polar fractions. About 180 compounds from the saponin group were tentatively identified, of which 9 and 3 were selected as distinctive markers for I. meserveae and I. aquifolium, respectively. Based on chemical screening, I. aquifolium Silver Queen was chosen as the source of terpenoid and saponin fractions and polyphenol extracts. The most substantial inhibition of cancer cell growth was observed with saponin in the case of the MCF7 (human breast cancer) cell line, while for LoVo and L929 cell lines (human colorectal cancer and reference mouse fibroblasts), it was slightly weaker. These results should be analysed further as a promising chemoprevention of colorectal and gastrointestinal cancers. Saponin and polyphenolic extracts exhibited similar activities against HSV-1 and HAdV-5, with 4-log reduction in virus titres. This study focuses our attention on a field of potential antiviral formulations derived from European holly. [ABSTRACT FROM AUTHOR]

Soursop leaves (Annona muricata) contain various secondary metabolite compounds with pharmacological benefits. This study foccused on the activity and chemical components cytotoxic active fraction of soursop leaf dichloromethane extract. From maceration of 535.8 g dried sample of A. muricata leaves we obtained extracts of n-hexane (18.4 g; 3.43 %). dichloromethane (11.4 g; 2.23 %). and methanol (48.7 g; 9.95 %). The dichloromethane extract was separated for its chemical components using gravity column chromatography resulting in 9 combined fractions. Toxicity screening test was done based on Bhrine Shrimp Lethality Test (BSLT) and cytotoxic test using MTT method 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide. The highest toxicity and cytotoxic test results were found in DMD 1 dichloromethane extract of A. muricata leaves with LC50 of 19.05 µg/mL and IC50 of 824.09 µg/mL. The results of DMD 1 gravity column re-chromatography produced 6-combined subfractions with the best separation pattern on DMD 1.4 and the results of GC-MS chromatogram analysis showed 29 peaks with the main component of fatty acid compounds namely Carbonic acid. but-2-yn-1-yl octadecyl ester (70.46 %). Potential anticancer compounds found were Phytol; 2-Hydroxy-1.1.10-trimethyl-6.9-epidioxydecalin and 2-Piperidinone. N-(4-bromo-n-butyl). [ABSTRACT FROM AUTHOR]

The objective of this study was to isolate and characterize rutin from the endophytic Nigrospora sphaerica of Euphorbia hirta L. The compound was isolated and purified through thin layer chromatography (TLC) and high-performance liquid chromatography (HPLC). Further, it was identified as rutin (RN) using fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), and high resolution mass spectroscopy (HRMS) analyses. The estimated RN concentration in the culture filtrate of N. sphaerica was 19.54 mg/L. The calculated IC 50 values of RN with respect to antioxidant potential estimated using 2, 2-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), hydrogen peroxide (H 2 O 2), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and nitric oxide (NO) approaches were 29.1, 36.5, 42.2 and 43.4 µg/mL, respectively. Besides, a combined treatment of RN and cisplatin (CP) inhibited the survival of tumor cells (HuT-78) significantly (P<0.05). Interestingly, the RN enhanced the apoptosis-inducing ability of CP considerably. In conclusion, N. sphaerica may be exploited as an alternative source of rutin for various commercial applications. [Display omitted] • This is the first report on isolation of rutin (RN) from N. sphaerica of E. hirta L. • RN identified through TLC, HPLC, FTIR, NMR and HRMS analyses. • Antioxidant activity of the RN is comparable to ascorbic acid, rutin and quercetin. • RN significantly augmented the cytotoxic activity of cisplatin against tumour cells. [ABSTRACT FROM AUTHOR]

Hericium erinaceus is a species of mushroom with high nutritional value that is used mainly as food in tropical countries. Phytochemical study of H. erinaceus led to the isolation of an undescribed compound, named as hericium VN (1), together with nine known compounds, 1-(2-formyl-1-pyrrolyl)butanoic acid (2), herierin III (3), 5′-(methylthio)adenosine (4), adenosine (5), nicotinic acid (6), (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol (7), 5α,8α-peroxycerevisterol (8), (22E,24R)-5α,8α-epidioxy-egosta-6,22-diene 3-O-β-D-glucopyranoside (9), and cerevisterol (10) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configuration of compound 1 was determined by experimental combined with calculated electronic circular dichroism spectra. Compound 7 exhibited cytotoxic effects against brain tumor cell line CCF-STTG1 with the IC50 value of 15.50 µM, compared to that of the positive control compound, doxorubicin, which showed IC50 value of 15.84 µM. [ABSTRACT FROM AUTHOR]

A new seco-A tirucallane triterpenoid named excelxylin A (1), along with two known seco-A triterpenoids (2–3), were isolated from the n-hexane extract of Dysoxylum excelsum (Spreng.) Blume ex G.Don stem bark. The structure and stereochemistry configuration of compounds 1–3 was established by NMR, IR, and HR-ESI-MS spectroscopic data analyses and comparison of their NMR data with literatures. The compounds exhibited the carbon framework for seco-A ring tirucallane triterpenoid, first reported in the Dysoxylum genus. All compounds were tested for their cytotoxicity against human cervical HeLa cells. [ABSTRACT FROM AUTHOR]

Introduction: The work presents the results of the study of new imidazotetrazine derivatives to establish the possibility of using them as anticancer agents, including for chemotherapy of metastatic breast cancer. The relevance of the work is due to the wide spread of oncological diseases and high cancer mortality, which dictates the need to constantly obtain cell lines and improve cultivation protocols for testing new antitumor drugs. The goal of this study is to check the potential of five new imidazotetrazine derivatives to become new antitumor drugs, in the scope of studying their cytotoxic and cytostatic activities on breast cancer cell cultures. Materials and Methods: The culturing MCF-7, MDAMB231, BT474, and MCF-10a cells with determining cytotoxic and cytostatic activities of five new azolotetrazine derivatives are base methods used in this study. Results: For the MCF-7 culture, MCS of comparison drug temozolomide was equal to 2.44 and IC50 was 6.81 mM/L; for other cultures CTA indicators were worse. Imidazotetrazine 2 and imidazotetrazine 3 demonstrated CTA indicators lower than those of temozolomide. IC50 was not achieved, and the MCS value varied between 1.34 and 1.74. These two derivatives were classified as the compounds with an extremely low CTA. Imidazotetrazine 1 and iminothiotriazine 5 showed cytotoxic activity higher than that of the comparison drug and we classified these compounds as the ones with a moderate CTA. Finally, we found imidazotetrazine 4 with IC50 of 0.85 mM/L and CTA of 7.34 as a compound with a potentially strong anticancer effect for further investigation. The cytostatic activity of four of the five azoloazine derivatives studied was in a narrow range corresponding to the survival rate from 0.21 to 0.32, depending on the compound and cell culture. Against this background, imidazotetrazine 4 demonstrated a higher CSA, determined by the survival rate from 0.17 to 0.20. Conclusion: As a result of an in vitro study, we found that five new azolotriazine derivatives can be evaluated in the ascending order of these properties, as a combination of CTA+CSA in order imidazotetrazine 2, imidazotetrazine 3 < temozolomide < imidazotetrazine 1, iminothiotriazine 5 < imidazotetrazine 4, although the CSA of all the studied compounds turned out to be high. Thus, 3-Cyclohexyl-4-oxoimidazo[5,1-d]-[1,2,3,5]tetrazine-8-N-piperidinyl-carboxamide (imidazotetrazine 4) is an unconditional leader in the tested series of new azoloazine derivatives and we recommend it for further preclinical trials. [ABSTRACT FROM AUTHOR]

Ten new decalin polyketides, zosteropenilline M (1), 11-epi-8-hydroxyzosteropenilline M (2), zosteropenilline N (3), 8-hydroxyzosteropenilline G (4), zosteropenilline O (5), zosteropenilline P (6), zosteropenilline Q (7), 13-dehydroxypallidopenilline A (8), zosteropenilline R (9) and zosteropenilline S (10), together with known zosteropenillines G (11) and J (12), pallidopenilline A (13) and 1-acetylpallidopenilline A (14), were isolated from the ethyl acetate extract of the fungus Penicillium yezoense KMM 4679 associated with the seagrass Zostera marina. The structures of isolated compounds were established based on spectroscopic methods. The absolute configurations of zosteropenilline Q (7) and zosteropenilline S (10) were determined using a combination of the modified Mosher's method and ROESY data. The absolute configurations of zosteropenilline M (1) and zosteropenilline N (3) were determined using time-dependent density functional theory (TD-DFT) calculations of the ECD spectra. A biogenetic pathway for compounds 1–14 is proposed. The antimicrobial, cytotoxic and cytoprotective activities of the isolated compounds were also studied. The significant cytoprotective effects of the new zosteropenilline M and zosteropenillines O and R were found in a cobalt chloride (II) mimic in in vitro hypoxia in HEK-293 cells. 1-Acetylpallidopenilline A (14) exhibited high inhibition of human breast cancer MCF-7 cell colony formation with IC50 of 0.66 µM and its anticancer effect was reduced when MCF-7 cells were pretreated with 4-hydroxitamoxifen. Thus, we propose 1-acetylpallidopenilline A as a new xenoestrogen with significant activity against breast cancer. [ABSTRACT FROM AUTHOR]

Eight sulfated triterpene glycosides, peronioside A (1) and psolusosides A (2), B (3), G (4), I (5), L (6), N (7) and P (8), were isolated from the sea cucumber Psolus peronii. Peronioside A (1) is a new glycoside, while compounds 2–8 were found previously in Psolus fabricii, indicating the phylogenetic and systematic closeness of these species of sea cucumbers. The activity of 1–8 against human erythrocytes and their cytotoxicity against the breast cancer cell lines MCF-7, T-47D and triple-negative MDA-MB-231 were tested. The most active against cancer cell compounds, psolusosides A (2) and L (6), which were not cytotoxic to the non-transformed cells of the mammary gland, were chosen to study the inhibition of the migration, formation and growth of colonies of the cancer cell lines. Glycoside 2 effectively inhibited the growth of colonies and the migration of the MDA-MB-231 cell line. Compound 6 blocked the growth of colonies of T-47D cells and showed a pronounced antimigration effect on MDA-MB-231 cells. The quantitative structure–activity relationships (QSAR) indicated the strong impact on the activity of the form and size of the molecules, which is connected to the length and architecture of the carbohydrate chain, the distribution of charge on the molecules' surface and various aspects of hydrogen bond formation, depending on the quantity and positions of the sulfate groups. The QSAR calculations were in good accordance with the observed SAR tendencies. [ABSTRACT FROM AUTHOR]

Limonoid group belongs to triterpenoid that has undergone further oxidation accompanied by the loss of four carbon atoms to form a furan ring in the chain. This limonoid compound is often found in the Chisocheton genus. Limonoid compounds have been known as compounds with high structural variations and this makes limonoids have diverse and interesting activities, including cytotoxic and anticancer. In the course of our continuing study for limonoid constituents that have cytotoxic activity against cancer cell lines, methanol extract of stem bark from the Chisocheton pentandrus plant provides significant activity. The methanol extract was separated using various chromatographic techniques in the normal and reverse stationary phase to produce four azadirone-type limonoid compounds (1-4). The elucidation structure of 1-4 was determined using spectroscopic methods including, UV-Visible, IR, and 1D-NMR as well as optical rotation. All four known compounds were established as trichilenone acetate (1), toonaciliaton C (2), 11α-acetoxiazadiron (3), and 16β- hydroxydisobinine (4). The cytotoxicity of compounds 1-4 was assessed by examination using the resazurin method, which showed that compound 4 was the promising constituent against the MCF-7 cells with an IC50 value of 43.1 µM and was stronger than its positive control. [ABSTRACT FROM AUTHOR]

Sesquiterpenoids are a class of terpenoid compounds with a remarkable diversity of structures and biological activities. Sesquiterpenoids are primarily found in higher plants, such as the Meliaceae family's Aglaia genus. Aglaia cucullata is a species of Aglaia that is still rarely explored and can potentially contain sesquiterpenoid compounds with cytotoxic activity. Hence, the research intended to isolate sesquiterpenoids from the n-hexane extract of A. cucullata stem bark and evaluate their cytotoxic effect against A549 lung cancer cells. Compounds 1 and 2 were isolated and purified from n-hexane extracts utilizing various chromatographic techniques. The structure of compounds 1 and 2 was determined by analyzing various spectroscopic methods (IR, MS, and NMR) and comparing them to previously reported spectral data. Compound 1 was identified as an isodaucane-type sesquiterpenoid, 10-hydroxy-6,10-epoxy-7(14)-isodaucane, and was first reported in Meliaceae family. Compound 2 was confirmed as an eudesmane-type sesquiterpenoid, eudesm-4(15)-ene-1β,6α-dihydroxy, and was first reported in Aglaia cucullata. Cytotoxic activity of 1 and 2 were investigated in vitro against A549 lung cancer cells using the PrestoBlue assay and resulted in inactive and low cytotoxicity with IC50 values of 292.77 and 90.55 μM, respectively. [ABSTRACT FROM AUTHOR]

AbstractThe cytotoxic activities of apolar extract of Lactarius salmonicolor and its fractions and subfractions were screened against colon (CaCo-2), prostate (LNCaP), lung (H1299), and breast (MCF-7) cancerous cell lines. The main extract of Lactarius salmonicolor that was cytotoxic to CaCo-2 (EC50: 137.1 ± 2.7 µg/mL) and LNCap (EC50: 131.2 ± 2.6 µg/mL) mainly contains fatty acids (99.9%). To characterize the cytotoxic activity, it was fractionated by a silica gel column. Two cytotoxic fractions were re-fractionated to obtain subfractions. The extract, four cytotoxic fractions, and all subfractions were analyzed by gas chromatography-mass spectrometry (GC-MS). The GC-MS data and the cytotoxic activity (EC50) results were classified using principal component analyses (PCA). According to PCA, the cytotoxic fractions containing abundant benzoic acid (0.01%–0.35%), cinnamic acid (0.01%–0.36%), azelaic acid (0.01%–0.92%), 2,4-decadienal (0.01%–0.12%), (Z)-9-palmitoleic acid (0.01%–1.09%), 18-hydroxy 2,4-diene oleic acid (0.01%–26.71%), arachidic acid (0.01%–6.70%), desmosterol (0.01%–12.27%), and steroids (0.01%–9.51%) were clustered. LSP.9-10, which causes another cluster, is caused by 8,11,14- eicosatrienoic acid, 11,14,17-eicosatrienoic acid, 9(Z)-decenoic acid compounds, and saturated fatty acids with 10 and 16 carbons. Hence, these compounds may be responsible for the cytotoxic activity. This study demonstrates that GC-MS and chemometric analysis can identify the components responsible for biological activity in combination with biological activity data. [ABSTRACT FROM AUTHOR]

Four new diterpenoids, isodosins A–D (1–4), together with nine known compounds (5–13) were isolated and identified from the aerial parts of Isodon serra (Maxim.) Hara. The structures of the new diterpenoids were elucidated based on the analysis of HR-ESI-MS data, 1D/2D-NMR-spectroscopic data, and electronic circular dichroism (ECD) calculations. Cytotoxicities of compounds 2, 3, 5, 6, and 9 against the HepG2 and H1975 cell lines were evaluated with the MTT assay. As a result, compounds 2, 3, and 6 revealed higher levels of cytotoxicity against HepG2 cells than against H1975 cells. Moreover, compund 6 demonstrated the most efficacy in inhibiting the proliferation of HepG2 cells, with an IC50 value of 41.13 ± 3.49 μM. This effect was achieved by inducing apoptosis in a dose-dependent manner. Furthermore, the relationships between the structures and activities of these compounds are briefly discussed. [ABSTRACT FROM AUTHOR]