A New Flavonoside from the Invasive Plant Macfadyena unguis-cati

Four new triterpene saponins, namely speciosides A-D (1–4) along with six known saponins were isolated from the n-butanol extract of Cephalaria speciosa. In addition to these, three new prosapogenins (2a–4a) were obtained after alkaline hydrolysis. Elucidation of the structures of the isolated compounds was carried out by 1D, 2D NMR, HR-ESI/MS and GC–MS analyses. Cytotoxic activity was investigated on A549, CCD34-Lu, MDA-MB-231, PC-3, U-87MG, HeLa, HepG-2 cells by MTT method. Additionally, the immunomodulatory effect of compounds was evaluated for macrophage polarization with/without inactivated IBV D274 antigen treatment on THP-1 cells originated macrophage cells in terms of M1 or M2. According to the cytotoxicity results, compound 1 and prosapogenin 2a exhibit significant cytotoxicity than doxorubicin by comparison. The results demonstrated that saponin molecules treated THP-1 originated macrophages were induced M1 and/or M2 polarization. Additionally, macrophage cells treated with/without IBV D274 antigen contained saponin compounds were triggered significantly M2 polarization relative to M1. Notably, monodesmosidic saponins (1 and 2a–4a) in comparison with bisdesmosidic ones (2–4) demonstrated the most effect on M2 polarization. In conclusion, the results showed that all the isolated new saponins and their prosapogenins have immunomodulatory potential on macrophage cells increasing immune response without significant cytotoxic effect on THP-1 originated macrophages.

Three new phenanthrenone constituents, trigoxyphins U–W (1, 7 and 9), together with eight known ones, trigoxyphin M (2), 6,9-O-dimethyltrigonostemone (3), trigonstemone (4), thrigonosomone B (5), trigonochinene E (6), actephiiol A (8), epiactephilol A (10) and neoboutomannin (11), were obtained from the methanol extract of the leaves and stems of Trigonostemonlii. The structures of the new metabolites were elucidated by analysing the spectroscopic data (1D NMR, 2D NMR, HR-ESI-MS and IR). Compounds 1–6 were evaluated for their cytotoxic activities on five human tumour cell lines by using the MTT method, and compound 1 exhibited inhibitory activity against HL-60, SMMC-7721, A-549, MCF-7 and SW480 with IC50 values ranging from 3.77 to 14.51 μM.

Two new sesquiterpenoids, named 2α-hydroxyxylaranolB(1) and 4β-hydroxyxylaranolB(2), together with a known diterpenoid 3,4-seco-sonderianol (3) were isolated from the fermentation of endophytic fungus J3 of Ceriops tagal. Their structures were elucidated based on spectroscopic methods including 1D and 2D NMR (HMQC, (1)H-(1)H COSY and HMBC). All compounds were evaluated for their cytotoxic activities by MTT method, and compound 3 exhibited cytotoxic activities against K562, SGC-7901, and BEL-7402 cell lines.

Benzofuwran derivatives found in several natural compounds and synthesized for various purposes. Due to their molecular structure’s electron behaviors they have several biological activities such as antitumor, cytotoxic, anticancer, antimicrobial, antifungal, ant proliferative etc. We synthesized (3-methyl-benzofuran-2-yl) ketoxime derivatives (one of them are new compound) and structure elucidation of the compounds was performed using IR, 1H-NMR, MASS spectroscopy and elemental analysis. X-Ray analysis of H2 compound was elucidated for the first time with this study in the literature. Cytotoxic activity against F2408 and HepG2 cell lines was also evaluated for the first time by MTT and NR uptake methods. Anti-microbial activity of H1, H2 and H3 was also investigated with broth micro dilution test. The results show that these ketoximes have cytotoxic and anti-microbial activity on different higher doses.

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded five new meroterpenoid metabolites, austalides M–Q (1–5), together with nine known compounds (6–13). The structures of the new compounds were unambiguously elucidated on the basis of extensive 1D and 2D NMR methods and by mass spectral analysis. Furthermore, the absolute configurations of 1 and 4 were determined by time‐dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configuration of analogous compounds 2, 3, and 5. The calculations revealed that the conformation of the benzene‐fused phthalide chromophore, which is sensitive to even minor changes in its proximity, is decisive for the ECD parameters, rendering a simple ECD comparison of related homochiral austalides difficult. All compounds were evaluated for their cytotoxic activity against murine cancer cell line L5178Y by using the MTT method. Compounds 8 and 11 exhibited moderate to pronounced cytotoxicity, with IC50 values of 39.4 and 0.2 μM, respectively, whereas the remaining investigated compounds showed either weak or no activity in this assay.

Cytotoxic constituents from the leaves of Broussonetia papyrifera

Seven new alkaloids including tryptoquivaline K (1) and fumiquinazolines K–P (2–7), bearing a rare 1‐aminocyclopropane‐1‐carboxylic acid residue, together with six known compounds (8–13), were isolated from the fungus Aspergillus sp. obtained from the Mediterranean sponge Tethya aurantium. The structures of the new compounds were determined by extensive analysis by 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configurations of tryptoquivaline K (1) and fumiquinazolines K and L (2, 3) were determined by TDDFT ECD calculations of their solution conformers, and the configurational assignment of the related fumiquinazolines M–P (4–7) was achieved by comparison of their ECD spectra with those of compounds 2 and 3. All compounds were evaluated for their cytotoxic activity by the MTT method. Compound 8 exhibited pronounced cytotoxicity against the mouse lymphoma cell line (L5178Y) with an IC50 value of 3.6 μM, but only moderate activity was observed against human ovarian cancer (A2780) and human Philadelphia chromosome‐positive chronic myelogenous leukemia (K562) cell lines with IC50 values of 18.5 and 15.0 μM, respectively.

Sesquiterpenoids from Carpesium divaricatum and their cytotoxic activity

In the Flora of Turkey, the genus Digitalis is represented by nine species [1]. Digitalis species contain biologically active compounds such as cardenolides, phenylethanoid glycosides, flavonoids, and anthraquinones. In this research three Digitalis species [Plantaginaceae]; D. davisiana Heywood, D. grandiflora Miller and D. viridiflora Lindley were studied in the point of cytotoxicity. To determine the bioactive part of the plant, root and aerial parts were extracted with methanol separately. Cytotoxic activity was performed by MTT method through 2 cancer cell lines HEp-2 (Human larynx epidermoid carcinoma), HepG2 (Human hepatocelular carcinoma) and a non-cancerous cell line 3Y1 (rat fibroblast cell) [2]. Methanol extracts of the aerial parts and the roots of three plants were used for cytotoxic activity tests. It was found that these three plants have different potentials for cytotoxicity. Aerial parts were found to be more active than the roots on tested cancer cell lines. In addition to this, D. davisiana aerial parts extract (DD-APE) was found to be the most active among all. IC50 values of DD-APE were 50.8, 211.4 and 94.7 µg/mL respectively for HEp-2, HepG2 and 3Y1 cell lines. The tested extracts are more cytotoxic on HEp-2 cell line than HepG2 and 3Y1 cell lines. This selectivity is important for the discovery of new anticancer agents. After evaluating the bioactivity test results, isolation studies started from active, phenylethanoid glycosides rich fractions. Repeated column chromatography studies resulted in the isolation of five phenylethanoid glycosides. Deacyllugrandoside (1), lugrandoside (2), isolugrandoside (3), maxoside (4) and 3,4-dihydroxy-β-phenylethoxy-O-[β-glucopyranosyl-(1→3)]-O-[α-rhamnopyranosyl-(1→6)]-4-O-(E)-feruloyl-β-glucopyranoside (5) were identified by extensive NMR techniques. Isolation and cytotoxic activity studies on isolated compounds are still in progress.

The search for bioactive compounds for the treatment of several diseases has led to the study of endophytic fungi. Neoplastic diseases are among the most significant health concerns due to their high mortality rate, and there is a dearth of efficacious pharmaceutical agents for the treatment of cancer. Gastric cancer is one of the most aggressive forms of cancer and is among those with the highest mortality rates in Brazil. Accordingly, the objective of this study was to identify compounds with cytotoxic activity from the mangrove-derived endophytic fungus Trichoderma sp. Isolation of the chemical compounds was conducted using chromatographic methods, while structural elucidation was achieved through the application of spectroscopic (NMR and UV) and spectrometric (MS) techniques. The fungus Trichoderma sp. was found to produce five distinct koninginins (A, B, C, E, and J). The organic phases of the extracts and isolated compounds were evaluated for their antimicrobial and cytotoxic potentials, respectively, through microdilution testing and the MTT method. In the cytotoxicity assay, both the AF extract and koninginin A demonstrated favorable outcomes, indicating their potential as promising anticancer therapeutic agents.

Avocado plants are widely used as traditional medicine in Indonesia. This research aimed to determine the cytotoxic and antiproliferation activity of avocado seed extract and fractions on the T47D breast cancer cell line. Extraction was done by maceration method using 96% ethanol, then fractionation was done by liquid-liquid partition using n-hexane, chloroform, and ethyl acetate. Cytotoxic and antiproliferation tests were done by the MTT method. Apoptosis activity was investigated by the double staining method, using acridine orange-propidium iodide as a staining reagent. Results showed that the n-hexane fraction of avocado seed had a cytotoxic activity with IC50 27.9 µg/mL. N-hexane fraction of avocado seed inhibited proliferation and induced apoptosis of T47D cell line.

Objective:The purpose of this research was to evaluate the cytotoxic, cell cycle arrest, and apoptotic induction activities of the fruit of S. nigrum L. ethanolic-70% extract against MCF-7 human breast cancer cell. Methods:S. nigrum L. ripe fruit was blended and macerated with ethanol 70% and the filtrate was evaporated. The semisolid extract was then analyzed phytochemically. Cytotoxic analysis was performed using MCF-7 cancer and Vero normal cell by MTT method and followed by apoptotic and cell cycle arrest analysis using flow cytometry. Results:The phytochemical analysis resulted that extract contained total phenolic and flavonoid compounds with the level of 1.545±0.080% and 0.212±0.002%, respectively. Glycitin was the highest level of isoflavone compound, namely, 375.0844 mg/100 g extract. The cytotoxic evaluation revealed that the extract exhibited a selectively toxic effect between cancer and normal cell. The extract inhibited MCF-7 proliferation with IC50 value about 40.77±4.86 μg/mL and conversely toward Vero cell at lower cytotoxic activity with an IC50 value of 298.96±27.28 μg/mL. Evaluation of MCF-7 cell cycles demonstrated that the extract arrested the cell cycle in the S phase and continued to the G2/M phase at the half of the IC50 value. The extract induced apoptotic of MCF-7 cell about 43.31% in which this activity was nearly the same with doxorubicin as a positive control (59.14%). However, solamargine was predicted as the most active anticancer compounds by a molecular docking study so that it was suggested to measure the level of this compound. Conclusion: It can be concluded that the fruit of S. nigrum L. ethanolic-70% extract demonstrated cytotoxic activity toward MCF-7 breast cancer cell and nontoxic on Vero normal cell. Solamargine was predicted as the most active anticancer compound. This extract had an opportunity to be developed as a potential anticancer agent to overcome breast cancer diseases.

Chemical composition and biological activities of propolis samples from different geographical regions of Turkey

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

Blumea lacera (B. lacera) (Asteraceae) is a well-known Bangladeshi medicinal plant. This study aimed to identify and characterize constituents associated with the significant cytotoxic activity of this plant that we reported previously. Here, we describe the isolation and characterization of a new steroidal glycoalkaloid (SGA) 1, the evaluation of its cytotoxic activity, apoptotic potential, and effect on cell cycle in comparison to analogous steroidal glycoalkaloids (SGAs). SGA 1 was isolated using C18 SPE and HPLC, and subsequently structurally characterized using 1D and 2D NMR, MS and other spectroscopic methods, along with a comparative inspection of the literature. Cytotoxic activity of 1 and seven SGA analogues and steroidal alkaloids (SAs), (β-solamarine, α-solanine, β-solamargine, α-solasonine, khasianine, solasodine, tomatidine HCl) were evaluated for their cytotoxicity against two healthy (NIH3T3 and VERO) and four human cancer (AGS, HT-29, MCF-7 and MDA-MB-231) cell lines using the MTT assay. Cytotoxic SGAs were further evaluated for apoptosis-inducing potential and cell cycle arresting ability against breast cancer cells (MCF-7) using the FITC Annexin V and propidium iodide (PI) assay. Bioactivity guided fractionation of the methanol extract of B. lacera led to isolation of compound 1: (25R)-3β-{O-β-D-glucopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 4)-[O-α-L-rhamnopyranosyl-(1 → 2)]-α-L-rhamnopyranosyl}-22αN-spirosol-5-ene. SGA 1 was the most cytotoxic compound against a number of human cancer cell lines with an IC50 of 2.62 µM against MCF-7 cells. It displayed the highest apoptotic potential (32% AV+/PI-) on MCF-7 cells compared to other cytotoxic SGA analogues and a slight, but significant cell cycle arresting effect. A new SGA 1 was isolated from B. lacera and its cytotoxic activity, as well as that of other SAGs, was evaluated. SAR investigations on SGA 1, in relation to SGA analogues, show that the number and nature of sugar moieties along with the linkages of the sugar to the aglycone are crucial for cytotoxic and apoptotic activity. This article is open to POST-PUBLICATION REVIEW. Registered readers (see "For Readers") may comment by clicking on ABSTRACT on the issue's contents page.