Evaluation of the cytotoxicity on breast cancer cell of extracts and compounds isolated from Hyptis pectinata (L.) poit

Abstract

Hyptis pectinata is a herb popularly used in Brazil for the treatment of inflammations, pain, bacterial infections and cancer. In the present study, inflorescences (MPIn), leaves (MPL), branches (MPB), root (MPR) extracts and three compounds isolated from MPIn were assayed against breast tumor cell lines. The structures of the three compounds (pectinolide J, hyptolide and pectinolide E) were determined by means of spectroscopic analysis. Pectinolide J was isolated for the first time. The MPIn, MPL and MPR exhibited specific antiproliferative activity on tumor cell lines when compared to normal cell lines with IC₅₀ of 52.01?±?0.64, 45.91?±?0.02?μg/mL and 82.84?±?0.03?μg/mL, respectively. Although the isolated substances did not present good antiproliferative activity, when the three were associated, a greater biological effect was observed, suggesting a synergistic effect. Hyptolide (5.6?±?0.4?μg/mL) showed IC₅₀ sufficiently low to be considered as a drug prototype.     

Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety

Abstract

A series of novel 1,2,4-triazole derivatives containing a pyrimidine moiety were synthesized and their fungicidal activities were evaluated. The preliminary biological test indicated that some of the target compounds exhibited moderate to good fungicidal activities against the tested plant pathogenic fungi compared with the commercial agent. Among them, compounds 9n and 9o exhibited excellent antifungal activity against Phompsis sp., with the half-maximal effective concentration (EC₅₀) values of 25.4 and 31.6?μg/mL, which were even better than the commercial agent of Pyrimethanil (32.1?μg/mL). Meanwhile, compound 9o showed better fungicidal activities against B. dothidea and B. cinerea with 40.1 and 55.1?μg/mL, respectively, in comparison with that of commercial Pyrimethanil (57.6 and 62.8?μg/mL).     

Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720

Abstract

Two new compounds, 5-[2-hydroxypropane-1-yl]-2,6-dimethlbenzene-1,3-diol (1) and coniochaetone L (2), together with 19 known compounds (3–21), were isolated from a deep-sea fungus, Penicillium sp. SCSIO 06720. Their structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism spectra. All the isolated compounds (1–21) were tested for their antibacterial and HIV latency-reversal activities. Among these compounds, compound 16 showed moderate antibacterial activities against Staphylococcus aureus ATCC 29213 and Methicillin-Resistant Staphylococcus Aureus-shh-1 with MIC values of 10.4?±?3.7?μg/mL and 46.9?±?29.7?μg/mL, respectively, which were comparable to that of the positive control ampicillin with MIC values of 0.5?±?0.4?μg/mL and 2.7?±?0.9?μg/mL, respectively.     

Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties

Abstract

Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC₅₀ = 2.8?μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC₅₀ values ranged between 4.96 and 7.44?μg/mL in comparison to doxorubicin (IC₅₀ = 0.426–0.493?μg/mL).     

Cytotoxicity of syringin and 4-methoxycinnamyl alcohol isolated from Foeniculum vulgare on selected human cell lines

This study was carried out to determine the cytotoxic effect of seven plant extracts and the isolated compounds – syringin and 4-methoxycinnamyl alcohol – on cancerous and non-cancerous cells. The ethanol extract of Foeniculum vulgare was found to exhibit the most significant toxicity with an IC₅₀ value of 19.97 μg/mL on HeLa cells. Bioassay-guided fractionation led to the isolation of two compounds, syringin (1) and 4-methoxycinnamyl alcohol (2). Both compounds showed toxicity against MCF-7, HeLa and DU145 cancer cell line. The results showed that compound 2 showed high toxicity against all the cancer cell lines with IC₅₀ values of 14.24, 7.82 and 22.10 μg/mL, respectively. 4-Methoxycinnamyl alcohol also showed no apoptotic effect in cell cycle analysis after 48 h at a concentration of 10 μg/mL. However, DNA fragmentation study revealed that necrosis took place at a concentration of 10 μg/mL after 48 h exposure.     

GC-EIMS analysis,antifungal and anti-aflatoxigenic activity of Capsicum chinense and Piper nigrum fruits and their bioactive compounds capsaicin and piperine upon Aspergillus parasiticus

Abstract

GC-EIMS analysis, antifungal- and anti-aflatoxigenic activities of the ethanolic extract of Capsicum chinense and Piper nigrum fruits and their main bioactive compounds were evaluated upon Aspergillus parasiticus. The GC-EIMS analysis showed capsaicin (50.49%) and piperine (95.94%) as the major constituents in C. chinense and P. nigrum, respectively. MIC₅₀ values revealed that capsaicin (39?μg/mL) and piperine (67?μg/mL) were lower than those from fruit extracts of C. chinense (381?μg/mL) and P. nigrum (68?μg/mL). Extracts and bioactive compounds showed anti-aflatoxigenic activity. Maximum aflatoxin inhibition occurred at 150?µg/mL of extracts and compounds. The present study showed satisfactory results concerning the effects of ethanolic extract of C. chinense and P. nigrum fruits upon A. parasiticus, showing the capabilities of inhibiting fungal growth development and altering aflatoxins production.     

Ligand fishing and identification of acetylcholinesterase inhibitors in Mahonia bealei (Fort.) Carr. using high performance liquid chromatography-mass spectrometry

Abstract

A fishing platform was developed using immobilized capillary enzyme reactors in combination with liquid chromatography-mass spectrometry (LC-MS) to fish acetylcholinesterase inhibitor (AChEI) from Mahonia bealei (Fort.) Carr. (M. bealei) extract. Four potential AChEIs (columbamine, jatrorrhizine, berberine, and palmatine) were successfully screened out and identified. Their AChE inhibitory activities were further verified by an in vitro assay with IC₅₀ values of 0.93?±?0.12?μg/mL (columbamine), 3.50?±?0.15?μg/mL (jatrorrhizine), 2.51?±?0.12?μg/mL (berberine), and 1.52?±?0.13?μg/mL (palmatine). A synergy study of these AChEIs was subsequently investigated. In comparison with the IC₅₀ value of M. bealei extract (IC₅₀=0.83?±?0.21?μg/mL), it can be stated that M. bealei extract is much more active than any single AChEI. Thereafter, the determination of these four alkaloids were investigated and AChE inhibitory effect were compared in terms of the extract and corresponding contents of these four alkaloids. The inhibitory effects of extract at each concentration were stronger than four alkaloids mixture. The results demonstrated that not the four AChEI mixture cause the synergistic effect but rather than the concentrations or ratios of these AChEIs play a vital role in their synergy study.     

Phytochemical constituents and antioxidant activity of Echinops albicaulis

Two thiophenes; 5-(3-buten-1-ynyl)-2,2′-bithiophene (2) and α-tertthienyl (9), two alkaloids; echinopsine (10) and echinorine (11), three flavonoids; genkwanin (5), apigenin (6), and rutin (7), two triterpenoids; lupeol acetate (1) and lupeol linoleate (4), together with 2,6,10-trimethyldodeca-2,6,10-triene (4) and β-sitosterol glucoside (8) were isolated from the aerial parts of Echinops albicaulis. Antioxidant, antimicrobial and antiprotozoal activities were evaluated. E. albicaulis aqueous methanolic extract (50, 10, and 1 mg/mL) showed significant antioxidant activity comparable to the potent antioxidant, N-acetyl cysteine, moreover, the aqueous methanolic extract (1 mg/mL) significantly reduced intracellular reactive oxygen species in active cell cultures of human peripheral blood mononuclear cells under oxidative stress more than the reference antioxidant N-acetyl cysteine. None of the isolated compounds showed antimicrobial or antiprotozoal activities at concentration up to 20 μg/mL.     

A novel cyclic dipeptide from deep marine-derived fungus Aspergillus sp. SCSIOW2

A novel cyclic dipeptide, 14-hydroxy-cyclopeptine (1), was purified from a deep sea derived fungal isolate identified as an Aspergillus sp. The structure was elucidated by detailed spectroscopic analyses using 1D and 2D NMR experiments and high resolution mass spectrometry. The absolute configuration of the amino acid was determined by Marfey's method. Two conformational isomers of 1 were established by ROE analyses. 1 inhibited nitric oxide production with IC₅₀ values at 40.3 μg/mL in a lipopolysaccharide and recombinant mouse interferon-γ -activated macrophage-like cell line, RAW 264.7 and showed no cytotoxic effect in the tested dose range up to 100 μg/mL.     

Antifungal,anti-inflamatory and neuritogenic activity of newly-isolated compounds from Disporopsis aspersa

Abstract

A new ester (1) and a terpenoid (2) were isolated from the dried whole plant of Disporopsis aspersa (H_UA) E_NGL. ex D_IELS for the first time and their structures were elucidated, as well as their biological activities are described. The two compounds all showed good antifungal activities, especially furanone (2) exhibited better antifungal activity against Pseudoperonospora cubensis and Phytophthora infestans with EC₅₀ value of 22.82, 18.90?μg/mL, respectively. Compound 1 exhibited a significant promotion on the neurite outgrowth in NGF-induced PC-12 cells, and moderate inhibition on the NO production induced by lipopolysaccharide (LPS) in BV-2 microglial cells.     

Atalantums H-K from the peels of Atalantia monophylla and their cytotoxicity

Abstract

Four new benzoyltyramines, atalantums H-K (1–4) and seven known compounds were isolated from the peels of Atalantia monophylla. All compounds were tested for cytotoxicity against HeLa, HCT116 and MCF-7 cell lines, as well as normal cells (Vero cells). Compound 5 showed cytotoxicity against HeLa, HCT116 and MCF-7 cell lines with IC₅₀ values ranging from 16-25?μg/mL but was inactive against Vero cells. Compound 6 also showed interesting results as compound 5 with IC₅₀ values ranging from 15-18?μg/mL and an IC₅₀ value of 80.20?μg/mL against Vero cells. This means compounds 5 and 6 can be used as lead compounds for anticancer agents.     

Insecticidal,cytotoxic and anti-phytopathogenic fungal activities of chemical constituents from the aerial parts of Ferula sinkiangensis

Abstract

A new rare monoterpene coumarin (1) and its two known analogues (2–3), together with two sesquiterpenes (6–7) and ferulic acid (8) were isolated from the aerial parts of Ferula sinkiangensis. The structure of new compound was established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. Insecticidal, cytotoxic and anti-phytopathogenic fungal activities of isolated compounds were evaluated against third-instar larvae of Spodoptera exigua and its cell line, and three plant pathogenic fungi respectively. Compounds 1–3 and 6–7 were found to be more effective contact toxicity to S. exigua with the corrected mortality values of 38.89%-58.89% at 10?μg/larva doses for 24?h. Further studies showed that compounds 3 and 6 exhibited cell growth inhibitory activity against S. exigua cell line with the EC₅₀ values of 22.78 and 14.64?µM for 72?h. In addition, compound 6 exhibited potent antifungal activity with MICs?=?16–32?µg/mL.     

Terretonin D1, a new meroterpenoid from marine-derived Aspergillus terreus ML-44

A new meroterpenoid, named terretonin D1 (1), and three known ones, terretonin (2), terretonin A (3), and terretonin D (4), were isolated from marine-derived fungus Aspergillus terreus ML-44. The structure of 1 was elucidated by extensive spectroscopic methods, including 1D and 2D NMR, HR-ESI-MS, and the absolute configuration was determined by X-ray crystallographic analysis. The anti-inflammation activity of 1–4 was preliminarily tested, and all of them weakly inhibited the nitric oxide (NO) production of RAW264.7 macrophages stimulated by lipopolysaccharide (LPS), with inhibitory rates of 22–34% at 50?μg/mL.     

Xanthones from a lignicolous freshwater fungus (BCC 28210)

Abstract

Four xanthones (1?4) and a known compound, mansonone D (5), were isolated from the lignicolous freshwater fungus BCC 28210 (family, Chaetosphaeriaceae). The structures of these compounds were elucidated by extensive spectroscopic analysis. Among the isolated metabolites, compound 2 and the known mansonone D (5) displayed antimalarial activity against Plasmodium falciparum K1 with IC₅₀ values of 7.75 and 0.55?μg/mL, respectively. Compound 4 displayed antibacterial activity against Bacillus cereus with an MIC value of 6.25?μg/mL.     

New chemical constituents from the Piper betle Linn. (Piperaceae)

The phytochemical investigation of chloroform extract from Piper betle var. haldia, Piperaceae, leaves has resulted in the isolation of two new chemical constituents which were identified as 1-n-dodecanyloxy resorcinol (H1) and desmethylenesqualenyl deoxy-cepharadione-A (H4), on the basis of spectroscopic data 1D NMR (¹H and ¹³C) and 2D NMR (¹H-¹H COSY and HMBC) as well as ESI-MS, FT-IR and HR-ESI-MS analyses. Compounds H1 and H4 showed excellent antioxidant DPPH free radical scavenging activity with IC₅₀ values of 7.14 μg/mL and 8.08 μg/mL compared to ascorbic acid as a standard antioxidant drug with IC₅₀ value of 2.52 μg/mL, respectively. Evaluation of cytotoxic activity against human hepatoma cell line (PLC-PRF-5) showed moderate effect with the GI₅₀ values of 35.12 μg/mL for H1, 31.01 μg/mL for H4, compared to Doxorubicin^® as a standard cytotoxic drug with GI₅₀ value of 18.80 μg/mL.     

Chemical constituents of the fermentative extracts of marine fungi Phoma sp. CZD-F11 and Aspergillus sp. CZD-F18 from Zhoushan Archipelago,China

A new diphenyl ether (1) as well as 20 other compounds were identified from the fermentative extracts of marine-derived fungi Phoma sp. CZD-F11 (Compounds 1–8) and Aspergillus sp. CZD-F18(Compounds 9–21). Their structures were elucidated on the basis of extensive spectroscopic analysis. The broth extracts of the fungi exhibited very good anticancer activity against H1975 cells with 5.62 and 25.8% viability at concentration of 10 μg/mL for Phoma sp. CZD-F11 and Aspergillus sp. CZD-F18, respectively. The inhibitory activity of all compounds against PC-3 cell lines, BRD4 and aromatase were evaluated. The results showed compound 7 exhibited moderate anticancer activity with 66.1% inhibition against PC-3 cell lines at the concentration of 10 μg/mL. Compound 7 and 8 exhibited favourable BRD4 inhibitory activity with 78.5 and 76.4% inhibition at the concentration of 10 μg/mL.     

GC-MS analysis of metabolites from soxhlet extraction,ultrasound-assisted extraction and supercritical fluid extraction of Salacca zalacca flesh and its alpha-glucosidase inhibitory activity

Abstract

Different extraction processes were employed to extract bioactive metabolites from Salacca zalacca flesh by a range of aqueous and organic solvents. The highest extraction yield was obtained by 50% ethanol extract of SE (73.18?±?4.35%), whereas SFE_1 showed the lowest yield (0.42?±?0.08%). All extracts were evaluated for in vitro α-glucosidase inhibitory activity, measured by their IC₅₀ values in comparison to that of quercetin, the positive control (IC₅₀ = 2.7?±?0.7?μg/mL). The lowest α-glucosidase inhibitory activity was indicated by water extract of SE (IC₅₀ = 724.3?±?42.9?μg/mL) and the highest activity was demonstrated by 60% ethanol extract by UAE (IC₅₀ = 16.2?±?2.4?μg/mL). All extracts were analysed by GC-MS and identified metabolites like carbohydrates, fatty acids, organic acids, phenolic acids, sterols and alkane-based compounds etcetera that may possess the potential as α-glucosidase inhibitor and may attribute to the α-glucosidase inhibitory activity.     

β-secretase 1 inhibitory activity and AMP-activated protein kinase activation of Callyspongia samarensis extracts

Abstract

The methanolic extract of Callyspongia samarensis (MCS) significantly inhibited β-secretase 1 (IC₅₀ 99.82?µg/mL) in a dose-dependent manner and demonstrated a noncompetitive type of inhibition. Furthermore, it exhibited the highest AMPK activation (EC₅₀ 14.47?μg/mL) as compared with the standard, Aspirin (EC₅₀ >100?μg/mL). HPLC/ESI-MS analysis of MCS extract revealed 15 peaks, in which nine peaks demonstrated similar fragmentation pattern with the known compounds in literature and in database library: 5-aminopentanoic acid (1), 4-aminobutanoic acid (3), Luotonin A (4), (E)-3-(1H-imidazol-5-yl) prop-2-enoic acid (8), Galactosphingosine (10), D-sphingosine (11), 5,7,4′-trihydroxy-3′,5′-dimethoxyflavone (12), hydroxydihydrovolide (13), and 3,5-dibromo-4-methoxyphenylpyruvic acid (14); and 6 peaks are not identified (2, 5–7, 9, and 15). Acute oral toxicity test of MCS extract revealed that it is nontoxic, with an LD₅₀ of >2000?mg/kg. Assessment of BBB permeability of MCS extract showed that compound 15 was able to cross the BBB making it a suitable candidate for developing CNS drugs.     

Inula viscosa (L.) Aiton leaves and flower buds: Effect of extraction solvent/technique on their antioxidant ability,antimicrobial properties and phenolic profile

Abstract

This study was designed to establish the most effective solvent/technique for extracting antioxidant phytoconstituents from leaves and flower buds of Inula viscosa (L.) Aiton (Asteraceae) grown wild in Morocco. Maceration and hot extraction with methanol or water and Soxhlet ethanol extraction were utilized. The antioxidant potential was evaluated in vitro by DPPH, reducing power, and ferrous ions chelating activity assays. I. viscosa leaf and flower bud extracts displayed the strongest effect in the DPPH test, being the Soxhlet ethanol the most active ones (IC₅₀ = 54.24?±?0.21?μg/mL and 39.77?±?0.23?μg/mL); thus, they were selected for further investigations. The antimicrobial efficacy of the Soxhlet ethanol extracts against ATCC and food isolates strains was assayed; the leaf extract showed the best activity, and Candida albicans was the most sensitive strain (MIC = 125?µg/mL). The extracts resulted non-toxic against Artemia salina. Among the phenolics characterised by HPLC-PDA-ESI-MS, hispidulin hexoside, patuletin and spinacetin were identified for the first time.     

Antiglycation,antioxidant, and cytotoxic activities of Uvaria chamae root and essential oil composition

Abstract

Uvaria chamae (Annonaceae), is an essential oil bearing plant; the root is acclaimed as an effective remedy for folkloric diabetic therapy. The root extracts were evaluated for composition, antiglycation, antioxidant, and cytotoxicity. Flavonoids, cardiac glycosides, and tannins were relatively high in the alcohol extract; benzyl benzoate (23.3%), dimethoxy-p-cymene (14.2%), τ-cadinol (12.1%), and methyl thymol (8.7%) predominated the constituents identified by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The ethanol extract demonstrated significant antiglycation activity (IC₅₀, 1.12?mg/mL), and cytotoxicity to brine shrimp (LC₅₀, 25.01?µg/mL). The extract (IC₅₀, 8.0?µg/mL; absorbance 0.531, 100?µg/mL) also exhibited better antioxidant effects compared with the essential oil (IC₅₀, 50.0?µg/mL; absorbance 0.292, 100?µg/mL) using 2,2-diphenyl-1-picrylhydrazyl radical and ferric reducing power assays respectively. U. chamae root possess antiglycation effect, and may also reduce oxidative stress in patients with diabetes; its antiglycation effect, oil composition, and cytotoxicity are reported for the first time.