Chemical constituents of Mallotus macrostachyus growing in Vietnam and cytotoxic activity of some cycloartane derivatives

Two new cycloartane derivatives, macrostachyosides A (1) and B (2), and seventeen known compounds were isolated from the methanol extract of Mallotus macrostachyus leaves. Their structures were elucidated by NMR and MS data. Macrostachyosides A (1) and B (2) showed significant cytotoxic activities on KB (epidermoid carcinoma) and LU-1 (lung adenocarcinoma) human cancer cell lines with IC₅₀ values ranging from 4.31 ± 0.09 to 7.12 ± 0.07 μg/mL.     

Phytochemical profile and antioxidant activity of extracts of the peruvian peppertree Schinus areira L. from Chile

The Andean tree Schinus areira L. has multiple traditional uses, from the treatment of bronchitis and rheumatic diseases to menstrual cycle regulation and wound healing. With reported hypotensive, analgesic, antitumoral and anti-inflammatory properties, it acts predominantly against diseases related to oxidative stress. This study focuses on the antioxidant activity and phytochemical profile of the extracts of Schinus areira L.Serial extraction of the fruits was performed both by maceration and by Soxhlet. Total phenols and flavonoids were measured using the Folin-Ciocalteu method and AlCl₃, respectively. In vitro antioxidant activity was determined by FRAP and DPPH.Results were similar for both extraction methods. Primary metabolites detected included carbohydrates, proteins and amino acids; secondary metabolites included tannins, flavonoids, saponins, steroids and triterpenes. Antioxidant activity was confirmed for ethyl acetate, methanolic and aqueous extracts. The methanolic extract had both the highest polyphenol content (>195 mg GAE/ g dry weight) and the highest antioxidant activity [EC₅₀ > 476 μg/mL; >273 mg AA/g dry weight (DPPH); >301 mg AA/ g dry weight (FRAP)]. The extract does not produce macrophage cytotoxicity in RAW 264.7, which is indicated by an average cytotoxicity of 2% over 24 h.Our study serves as a starting point for future research on the pharmacological properties of Schinus areira L.     

Synthesis of new morpholine-connected pyrazolidine derivatives and their antimicrobial,antioxidant, and cytotoxic activities

A simple and convenient one-pot four-component synthesis of morpholine-connected pyrazolidine derivatives 2a–f and 4a–f was developed using direct metal-free catalysis, with the identities of the synthesized compounds confirmed by IR, NMR (¹H and ¹³C), mass spectrometry, and elemental analysis. The prepared compounds were inspected for antimicrobial, antioxidant, and cytotoxic activities.Antimicrobial and antifungal activities against five bacterial and four fungal pathogens, respectively, were investigated using the disc diffusion technique. In antibacterial activity, compounds 2d and 2f (MIC = 2 μg/mL) exhibited significantly higher activity than the standard ciprofloxacin. The results of antifungal assay showed that the activity of compound 4a (MIC = 0.5 μg/mL) was significantly higher than the standard clotrimazole. Antioxidant activity was screened based on ABTS⁺ radical scavenging and linoleic acid peroxidation performance. Compound 4a showed substantial antioxidant (91.3%) activities, as compared with the Trolox standard. Cytotoxicity was evaluated using HepG2 (liver), HeLa (cervical), and MCF-7 (breast) cancer cell lines, with high toxicities observed for 2b (GI₅₀ = 12.2 μm) and 4a (GI₅₀ = 07.8 μm).     

Synthetic analogues of durantoside I from Citharexylum spinosum L. and their cytotoxic activity

New iridoid glycoside derivatives from durantoside I, the latter from the dried flowers and leaves of Citharexylum spinosum, were synthesized by variously modifying a sugar moiety by silylation or acetylation and/or removal of cinnamate group at C-7 position and subsequent screening for comparative cytotoxicity against several cancer cell lines. Addition of alkylsilane to durantoside I and removal of cinnamate group were most effective in improving cytotoxicity.     

Characterization,antibacterial, antioxidant,and cytotoxic activities of ZnO nanoparticles using Coptidis Rhizoma

Here, we report a simple, eco-friendly and inexpensive approach for the synthesis of zinc oxide nanoparticles (ZnO NPs) using Coptidis Rhizoma. The ZnO NPs were characterized by UV–visible absorption spectroscopy, FTIR, SEM-EDX, TGA, TEM, SAED and XRD. TEM images confirmed the presence of spherical and rod shaped ZnO NPs in the range of 2.90–25.20 nm. Green synthesized ZnO NP_S exhibited moderate antibacterial activity against Gram-positive and Gram-negative bacteria and excellent DPPH free radical scavenging activity. Synthesized ZnO NPs had no toxic effects on the RAW 264.7 cell line.     

Nephroprotective,cytotoxic and antioxidant activities of Euphorbia paralias

ObjectiveTo investigate the effect of the ethyl acetate fraction of the aerial parts of E. paralias L. F. Euphorbiaceae on nephroprotective, cytotoxic, and antioxidant.Methodsdifferent spectroscopic and spectrophotometric methods were applied to identify phytoconstituents. The nephroprotective potential of E. paralias ethyl acetate fraction (Ep EtOAc) was evaluated in male rats with thioacetamide-induced kidney injury, as wll as cytotoxic activity was evaluated using a viability assay, and the antioxidant activity was evaluated using the DPPH method. Results: quantitative estimation of total phenolics and flavonoids of E. paralias was performed using unique spectrophotometric methods. The polyphenolic compounds gallic acid (1), ellagic acid (2), kaempferol-3-O-(6″-O-galloyl-β-D-glucopyranoside) (3), quercetin-3-O-β-D-glucopyranoside (4) and quercetin-3-O-β-D-arabinoside (5) were isolated from the ethyl acetate fraction of the aerial parts of E. paralias. The thioacetamide administration resulted in marked nephrotoxicity, but pretreatment with Ep EtOAc significantly attenuated the nephrotoxicity through alteration of kidney biomarkers, thereby improving the redox status of the tissue and restoring serum biochemical parameters nearly to normal levels. This study revealed a significant cytotoxic and strong antioxidant effect. Conclusion: we conclude that the Ep EtOAc may be used in the future as nephroprotective, cytotoxic, and antioxidant agent derived from a natural source.     

Two new unusual monoterpene acid glycosides from Acacia cyclops with potential cytotoxic activity

A phytochemical investigation of the Tunisian plant Acacia cyclops pods led to the isolation of two new monoterpenoid glycosides, which have been designated Cyclopside 1 and Cyclopside 2. Their structures were elucidated on the basis of extensive spectroscopic procedures including IR, MS and 2D-NMR. The cytotoxic effect of the isolates was also evaluated in vitro against the human breast cancer (MCF-7) and ovarian cancer (OVAR) cell lines. Results showed that the highest cytotoxic activity (90.88%) was against MCF-7 cell line and was exhibited by the Cyclopside 1 at the concentration of 50 μg/mL.     

Steroidal saponins with cytotoxic activities from the rhizomes of Anemarrhena asphodeloids Bge.

Two new steroidal saponins, named timosaponin R (1) and S (2), together with seven known compounds (3-9) were isolated from the rhizomes of Anemarrhena asphodeloides Bge. Their structures were elucidated on the basis of NMR spectroscopy and mass spectrometry. All the compounds were evaluated for cytotoxic activities against the four human cancer cell lines MCF7, SW480, HepG2 and SGC7901 in vitro. Compounds 7-9 showed moderate activities against all the cell lines.     

Deciphering chemical profiling,pharmacological responses and potential bioactive constituents of Saussurea lappa Decne. Extracts through in vitro approaches

Despite advancement in modern medicines, plant derived medicines have still wide range utilities as they have less side effects and are cheap and biocompitable. Sassurea lappa is an extensively used plant in traditional medicinal formulations. Plant roots are used to cure various diseases including cancer, rheumatic pain, abdominal and nervous disorders. The present study was aimed for the evalution of biological potentials of methanolic and chloroform extracts of Saussurea lappa root, leaf, seed and flower. The methanolic and chloroform extracts were subjected to qualitative and quantitative phytochemical analyses. Identification of functional groups was performed using Fourier Transform infrared (FT-IR) spectroscopy. Antioxidant potential was determined via diphenyl-1-picrylhydrazyl (DPPH), total reducing power (TRP) and total antioxidant capacity (TAC) method, anti-hemolytic potential was conducted on human RBCs, antibacterial activity was evaluated against six American type culture collection (ATCC) and three multi drug resistance (MDR) strains, cytotoxic and phytotoxic potentials were evaluated through brine shrimp lethality assay and raddish seed assay respectively. Experiments were performed in triplicates and analysis of variance (ANOVA) was applied using statistics version-8.1. Phytochemical analysis revealed the presence of sixteen secondary metabolites. Fourteen functional groups were identified through FTIR. S. lappa root methanolic (SLRM) showed maximum antioxidant activity index (AAI-79.42%) whereas chloroform extract of leaves (SLLC) gave highest antibacterial activity with maximum zone of inhibition (ZOI) against Pseudomonas aeruginosa (21.4 mm). Maximum cytotoxicity was observed for SLRM with lethal dose concentration (LC₅₀) of 58.8 µg/mL. However, root extracts showed significant phytotoxicity (15% germination). The current study investigated that bioactive compounds present in S. lappa leaves, seed, flower and roots were responsible for enhanced biological potentials. Further studies on isolation and characterization of these bioactive compounds may help in drug development. In future, we recommend different in-vitro and in-vivo studies to further confirm it biopharmacological potencies.     

Flavonoid constituents,cytotoxic and antioxidant activities of Gleditsia triacanthos L. leaves

Gleditsia triacanthos L. is a deciduous tree belonging to the family Fabaceae. It possesses important biological activities as anti-mutagenic, anticancer, cytotoxic and treating rheumatoid arthritis. The total ethanol extract (EtOHE) and successive extracts (petroleum ether, chloroform, ethyl acetate, and aqueous ethanol) were prepared from the leaves. Eight flavone glycosides and two flavone aglycones named vicenin-I (1), vitexin (2), isovitexin (3), orientin (4), isoorientin (5), luteolin-7-O-ß-glucopyranoside (6), luteolin-7-O-ß-galactopyranoside (7), apigenin-7-O-ß-glucopyranoside (8), luteolin (9) and apigenin (10) were isolated from the aqueous ethanol extract of G. triacanthos L. leaves. Potent cytotoxic activity of the EtOHE extract was observed against the liver (IC₅₀ = 1.68 μg), breast (IC₅₀ = 0.74 μg), cervix (IC₅₀ = 1.28 μg), larynx (IC₅₀ = 0.67 μg) and colon (IC₅₀ = 2.50 μg) cancer cell lines. Cytotoxic activity of compounds 2, 4, 6 and 8 against, the liver, breast and colon cancer cell lines was also proved. Evaluation of the in-vivo antioxidant activity of the EtOHE and successive extracts revealed that the highest activity was exhibited by 100 mg of EtOHE (97.89% potency) as compared with vitamin E (100% potency). Compound 6 showed 91.8% free radical scavenging activity.     

Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma

A series of 14-deoxy-11,12-didehydroandrographolide analogues were synthesized from naturally occurring andrographolide and their cytotoxicity evaluated against nine cancer cell lines including cholangiocarcinoma. Analogues 5a and 5b exhibited the most potent cytotoxicity with ED₅₀s of 3.37 and 3.08?μM on KKU-M213 cell lines and 2.93 and 3.27?μM on KKU-100 cell lines, respectively. Selective cytotoxicity on cholangiocarcinoma cell lines identified in this study highlight the importance of structural modification in the development of drugs for this cancer.     

Gerronemins A-F, cytotoxic biscatechols from a Gerronema species

The gerronemins A-F (1-6) were isolated as the cytotoxic components of an extract of a Gerronema species detected in a screening for new cytotoxic metabolites from basidiomycetes. Their structures were elucidated by spectroscopic techniques, and they are composed of a C12-C16 alkane or alkene substituted at both ends by 2,3-dihydroxyphenyl groups. The gerronemins blocked the inducible expression of a hCOX-2 and iNOS promoter driven reporter gene with IC50-values of 1-5 microg/ml. In addition, cytotoxic activities were observed which were due the inhibition of cellular macromolecular syntheses.     

Pregnane alkaloids from Sarcococca ruscifolia and their cytotoxic activity

Six pregnane alkaloids were isolated from the root of Sarcococca ruscifolia. The structures of three new alkaloids, namely, sarcorucinine E–G (1–3), were elucidated using spectroscopic methods, while three known alkaloids, namely, epipachysamine D, pachysamine M, and sarcovagine D, were identified by comparing their spectral data with those of the compounds reported earlier. All compounds were evaluated for their inhibitory activities against multiple types of cancer cells.     

New phenanthrene glycosides from Dendrobium denneanum and their cytotoxic activity

Five new phenanthrene glycosides, denneanosides A–E (1–5), and one new 9,10-dihydrophenanthrene glycoside, denneanoside F (6) were isolated from the stem of Dendrobium denneanum. The chemical structures of the new compounds were established on the basis of extensive spectroscopic data. The isolated compounds were evaluated for their in vitro cytotoxic activity against SNU387 hepatocellular carcinoma cell line. Compounds 1–3 showed moderate cytotoxic activities while compounds 4–6 showed weak activities.     

Comparative study of Cyperus rotundus essential oil by a modified GC/MS analysis method. Evaluation of its antioxidant, cytotoxic, and apoptotic effects

Gas chromatography coupled with mass spectrometry (GC/MS), using both electron impact (EI) and chemical ionization (CI) detection modes on apolar and polar stationary phases, led to the determination of the volatile composition of the essential oil obtained from tubers of Cyperus rotundus (Cyperaceae). In this study, more than 33 compounds were identified and then compared with the results obtained in our previous work. Cyperene, alpha-cyperone, isolongifolen-5-one, rotundene, and cyperorotundene were the principal compounds comprising 62% of the oil. An in vitro cytotoxicity assay with MTT indicated that this oil was very effective against L1210 leukaemia cells line. This result correlates with significantly increased apoptotic DNA fragmentation. The oxidative effects of the essential oil were evaluated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH), xanthine/xanthine oxidase assays, and the scavenging of superoxide radical assay generated by photo-reduction of riboflavin. The antimutagenic activity of essential oil has been examined by following the inhibition of H(2)O(2) UV photolysis which induced strand-break formation in pBS plasmid DNA scission assay. Based on all these results, it is concluded that C. rotundus essential-oil composition established by GC/MS analysis, in EI- and CI-MS modes, presents a variety of a chemical composition we were not able to detect with only GC/MS analysis in our previous work. This essential oil exhibited antioxidant, cytotoxic, and apoptotic properties.     

Antioxidative bioavailability of artepillin C in Brazilian propolis

Propolis has strong antioxidative activity. We investigated here whether this activity was available in intestinal Caco-2 and hepatic HepG2 cells. Phenolics in Brazilian propolis, extracted with ethyl acetate after the removal of resin and wax with 90% methanol, included artepillin C at 21 mmol/100 g, p-coumaric acid and cinnamic acid relatives 24mmol, kaempferol and its derivatives 9.4 mmol, naringenin 2.8 mmol, isosakuranetin 0.9 mmol, chrysin at 0.8 mmol/100 g, and several minor components. When the extract was added to the apical side of Caco-2 monolayers, artepillin C was specifically incorporated into the cells and released to the basolateral side mostly without conjugation. Then, artepillin C was added to HepG2 cells and exposed to reactive oxygens. Artepillin C prevented oxidative damage dose-dependently, and suppressed lipid peroxidation evaluated with thiobarbituric acid reactive substances by 16% and the formation of 8-hydroxy-2'-deoxyguanosine in DNA by 36% at a concentration of 20microM. Artepillin C is a bioavailable antioxidant.     

Iridoids and lignans from Valeriana officinalis L. and their cytotoxic activities

Two new iridoids (1 and 2), one new lignan (3) together with one known iridoid (4) and twelve known lignans (5－16) were obtained from the roots of Valeriana officinalis L. (V. officinalis). The structures were determined using IR, MS, ¹D and ²D NMR spectroscopy and the absolute configurations of the new structures were deduced by ECD experiments. All of the isolated compounds were assayed for their cytotoxic activities against three tumour cell lines (A549, HCT116 and SW620) and the results showed that compounds 9 and 10 showed cytotoxicities against A549 cells, compounds 9 and 11 showed cytotoxicities against SW620 cells and compound 10 showed cytotoxicities against HCT116 cells.     

Biological Evaluation of Secondary Metabolites from the Root of Machilus obovatifolia

Bioassay‐guided fractionation of the root of Machilus obovatifolia led to the isolation of four new lignans, epihenricine B ( 1 ), threo‐(7′R,8′R) and threo‐(7′S,8′S)‐methylmachilusol D ( 2 and 3 ), and isofragransol A ( 4 ), along with 23 known compounds. The compounds were obtained as isomeric mixtures (i.e., 2 / 3 and 4 / 20 , resp.). The structures were elucidated by spectral analyses. Among the isolates, 1 , licarin A ( 12 ), guaiacin ( 14 ), (±)‐syringaresinol ( 21 ), and (?)‐epicatechin ( 23 ) showed ABTS (=2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) cation radical‐scavenging activity, with SC₅₀ values of 11.7±0.5, 12.3±1.1, 11.0±0.1, 10.6±0.3, and 9.5±0.2 μM in 20 min, respectively. In addition, kachirachirol B ( 17 ) showed cytotoxicity against the NCI‐H460 cell line with an IC₅₀ value of 3.1 μg/ml.     

Chemical Composition and in vitro Biological Activities of the Essential Oil of Vepris macrophylla (Baker) I.Verd. Endemic to Madagascar

Vepris macrophylla is an evergreen tree occurring in sub‐humid forest of Madagascar and traditionally used in the Island to treat several complaints as well as to prepare aromatic teas and alcoholic drinks. In the present work, the essential oil distilled from the leaves was analyzed for the first time by gas chromatography (GC‐FID) and gas chromatography/mass spectrometry (GC/MS). The major compounds were citral (56.3%), i.e., mixture of neral (23.1%) and geranial (33.2%), citronellol (14.5%), and myrcene (8.3%). The essential oil exhibited antimicrobial activity against S. aureus, P. aeruginosa, and C. albicans as determined by vapor‐diffusion assay, supporting the traditional use of the plant for preparing steam bath for the treatment of infectious diseases. The essential oil was evaluated for cytotoxic activity on human tumor cell lines by MTT (=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) assay, showing inhibitory effects comparable to those of cisplatin, notably on MDA‐MB 231 (human breast adenocarcinoma) and HCT116 (human colon carcinoma) cell lines. Finally, the essential oil was also subjected to screening for its antioxidant activity and the free radical scavenging capacity.     

Antioxidant,antimicrobial and cytotoxicity potential of n-hexane extract of Cayratia trifolia L

It is of interest to analyze the antioxidant, antimicrobial and cytotoxicity activity of n-hexane extract of Cayratia trifolia L. (C. trifolia). The antimicrobial activity of n-hexane extract of C. trifolia was determined using disc diffusion method against six selected pathogenic microorganisms. The cytotoxicity potential of n-hexane plant extract was also studied against A2780 cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Results, n-hexane extract of C. trifolia possess significant antioxidant activity with significant IC50 values in radical scavenging assays. In antimicrobial studies, the maximum zone of inhibition was found in the range of 19.0 ± 0.1 to 22.0 ± 0.1 mm. In MTT assay, inhibition of cell growth with minimal IC50 values of 46.25±0.42μg/mL against A2780 cell lines was observed. Thus, n-hexane extract of C. trifolia is a possible antioxidant, antimicrobial and cytotoxicity agent.