scholarly journals Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 385 ◽  
Author(s):  
Kevin A. Martínez ◽  
Chiara Lauritano ◽  
Dana Druka ◽  
Giovanna Romano ◽  
Teresa Grohmann ◽  
...  
Keyword(s):  
Biological Activities ◽  
Chemical Properties ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Pancreas ◽  
Marine Microorganisms ◽  
Pancreas Carcinoma ◽  
Amphidinium Carterae

Due to the unique biodiversity and the physical-chemical properties of their environment, marine microorganisms have evolved defense and signaling compounds that often have no equivalent in terrestrial habitats. The aim of this study was to screen extracts of the dinoflagellate Amphidinium carterae for possible bioactivities (i.e., anticancer, anti-inflammatory, anti-diabetes, antibacterial and antifungal properties) and identify bioactive compounds. Anticancer activity was evaluated on human lung adenocarcinoma (A549), human skin melanoma (A2058), human hepatocellular carcinoma (HepG2), human breast adenocarcinoma (MCF7) and human pancreas carcinoma (MiaPaca-2) cell lines. Antimicrobial activities were evaluated against Gram-positive bacteria (Staphylococcus aureus MRSA and MSSA), Gram-negative bacteria (i.e., Escherichia coli and Klebsiella pneumoniae), Mycobacterium tuberculosis and the fungus Aspergillus fumigatus. The results indicated moderate biological activities against all the cancer cells lines and microorganisms tested. Bioassay-guided fractionation assisted by HRMS analysis allowed the detection of one new and two known amphidinols that are potentially responsible for the antifungal and cytotoxic activities observed. Further isolation, purification and structural elucidation led to a new amphidinol, named amphidinol 22. The planar structure of the new compound was determined by analysis of its HRMS and 1D and 2D NMR spectra. Its biological activity was evaluated, and it displayed both anticancer and antifungal activities.

scholarly journals ANTIMICROBIAL, CYTOTOXIC AND HEMOLYTIC ACTIVITIES OF MARINE ALGAE-ASSOCIATED FUNGAL ISOLATES IN VIETNAM

2019 ◽  
Vol 18 (4) ◽  
pp. 406-412
Author(s):  
Hoang Kim Chi ◽  
Tran Thi Hong Ha ◽  
Le Huu Cuong ◽  
Tran Thi Nhu Hang ◽  
Nguyen Dinh Tuan ◽  
...  
Keyword(s):  
Natural Products ◽  
Human Cancer ◽  
Biological Activities ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Marine Microorganisms ◽  
Fungal Strains ◽  
Fungal Isolates ◽  
Fungal Extracts

In the context of sources for natural products discovery are going scarcer, exploiting biotechnologically potential compounds from marine microbial symbionts is considered a relatively new trend. In our study a total of fifteen fungal strains were isolated from marine algal samples belonging to species Kappaphycus cottonii, K. striatus, Gracilaria eucheumatoides and Betaphycus gelatinus collected in Nha Trang in 2017. The in vitro biological activities, including antimicrobial, cytotoxic and hemolytic activities of ethyl acetate extracts of the fungal strains were determined. From fifteen fungal extracts, six displayed antimicrobial activity against at least one test strain. At 20 μg.ml-1, four fungal extracts were found to express cytotoxic activity on two human cancer cell lines hepatocellular carcinoma (Hep-G2) and breast adenocarcinoma (MCF-7), with G. eucheumatoides being the source of the highest number of producer strains. Hemolytic activity was observed in rabbit erythrocytes under almost all fungal extracts’ effect. No apparent relationship was observed between the biological activities of fungal isolates. The biological assessments uncovered several fungal candidates, such as Bge-1.1, Kco-2.1 and Geu-1.1 with relatively potent antimicrobial and cytotoxic activities while expressing less hemolytic effect at concentrations from 20 μg.ml-1 to 200 μg.ml-1. The results evidenced the potential of exploiting natural products from associated marine microorganisms, especially those for the purpose of pharmaceutical applications.

scholarly journals Chemical Composition and Biological Activities of Metabolites from the Marine Fungi Penicillium sp. Isolated from Sediments of Co To Island, Vietnam

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3830
Author(s):  
Hong Le ◽  
Quynh Do ◽  
Mai Doan ◽  
Quyen Vu ◽  
Mai Nguyen ◽  
...  
Keyword(s):  
Minimum Inhibitory Concentration ◽  
Secondary Metabolites ◽  
Inhibitory Concentration ◽  
Biological Activities ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Marine Microorganisms ◽  
Penicillium Species ◽  
E Coli ◽  
Strong Inhibitory Effect

Marine microorganisms are an invaluable source of novel active secondary metabolites possessing various biological activities. In this study, the extraction and isolation of the marine sediment Penicillium species collected in Vietnam yielded ten secondary metabolites, including sporogen AO-1 (1), 3-indolecarbaldehyde (2), 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3), 2-[(2R-hydroxypropanoyl)amino]benzamide (4), 4-hydroxybenzandehyde (5), chrysogine (6), 3-acetyl-4-hydroxycinnoline (7), acid 1H-indole-3-acetic (8), cyclo (Tyr-Trp) (9), and 2’,3’-dihydrosorbicillin (10). Their structures were identified by the analysis of 1D and 2D NMR data. Among the isolated compounds, 2-[(5-methyl-1,4-dioxan-2-yl)methoxy]ethanol (3) showed a strong inhibitory effect against Enterococcus faecalis with a minimum inhibitory concentration value of 32 µg/mL. Both 2-[(2R-hydroxypropanoyl)amino]benzamide (4) and 4-hydroxybenzandehyde (5) selectively inhibited E. coli with minimum inhibitory concentration values of 16 and 8 µg/mL, respectively. 2’,3’-Dihydrosorbicillin (10) potentially inhibited α-glucosidase activity at a concentration of 2.0 mM (66.31%).

scholarly journals LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

Metabolites ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 75
Author(s):  
Samah O. Alshehri ◽  
Rania T. Malatani ◽  
Hanin A. Bogari ◽  
Ahmad O. Noor ◽  
Amany K. Ibrahim ◽  
...  
Keyword(s):  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Carcinoma ◽  
Sulforhodamine B ◽  
Ic50 Values ◽  
Hepg2 Cell Lines

Chemical investigation of the ethyl acetate extract of Penicillium chrysogenum strain S003, a fungus isolated from Red Sea deep sediment, led to the isolation of a cerebroside molecular species LAMA (1) along with three other known compounds, ergosterol (2), epidioxyergosterol (3), and kojic acid (4). The structures of the isolated compounds were elucidated by interpretation of spectral data, including detailed 1D and 2D NMR (One and two dimensional Nuclear Magnetic Resonance) and mass spectrometry. The cytotoxic activities of isolated compounds 1–4 against five human carcinoma cells were evaluated using sulforhodamine B (SRB) assay. Compounds 2 and 3 displayed promising cytotoxic profiles against lung cancer (A-549), prostate (DU-145), breast adenocarcinoma (MCF-7), and hepatocellular (HepG2) cell lines, with IC50 values of 21.26, 19.3; 1.50, 6.10; 16.95, 13.6; and 2.89, 3.07 µM, respectively, while they were inactive against HeLa cells. Compounds 1 and 4 showed weak cytotoxic profiles against all cell lines under investigation.

scholarly journals Anthranoyl-substituted Norditerpene Alkaloids from Aconitum vulparia Rchb. and Their Cytotoxic Activities

2007 ◽  
Vol 62 (1) ◽  
pp. 135-141 ◽  
Author(s):  
Dezső Csupor ◽  
Peter Forgo ◽  
István Zupkóc ◽  
Pál Szabód ◽  
Judit Hohmann
Keyword(s):  
2D Nmr ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Nmr Studies ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Alkaloid Fraction ◽  
Norditerpene Alkaloids ◽  
Aconitum Vulparia

Extensive chromatographic purification of the alkaloid fraction of Aconitum vulparia Rchb. led to the isolation of a new norditerpene alkaloid, vulparine (1), besides the known compounds septentriodine (2), finetiadine (3), anthranoyllycoctonine (4), N-methyl-N-deethyllycoctonine (5) and delectinine (6). The structure of the new compound was determined by means of HRMS, 1D and 2D NMR spectroscopy. Detailed NMR studies, including 1H-1H COSY, NOESY, HSQC and HMBC experiments, resulted in complete and unambiguous 1H chemical shift assignments for 2 and 6, and revision of some 13C NMR data. Compounds 1 - 4 were evaluated for their cytotoxic activities, and 1, 3 and 4 were found to exhibit marginal cell growth inhibitory activity against breast adenocarcinoma (MCF-7) and cervix adenocarcinoma (HeLa) cells.

Two new glycosidal metabolites of endophytic fungus Penicillium sp. (NO.4) from Tapiscia sinensis

2016 ◽  
Vol 71 (4) ◽  
pp. 283-286 ◽  
Author(s):  
Qiao Wan ◽  
Ziwei Feng ◽  
Xueshuang Li ◽  
Mengmeng Lv ◽  
Zhiyong Guo ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Cancer Cell ◽  
Endophytic Fungus ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Antimicrobial Activities ◽  
Cytotoxic Activities ◽  
A549 Cancer Cell Line

AbstractTwo new glycosides, 8-O-β-d-glucopyranosyl-6-methyl-1-carboxylate methyl ester xanthone (1) and 4′-O-β-d-galactopyranosyl djalonensone (2), together with four known compounds, 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate methyl ester (3), cassionllin (4), djalonensone (5) and alternariol (6), were isolated from the endophytic fungus Penicillium sp. (NO.4) of Tapiscia sinensis Oliv. The structures of compounds 1–6 were elucidated by the analysis of 1D and 2D NMR and HRMS. The cytotoxic activities of these compounds were evaluated against four cancer cell lines, as well as antimicrobial activities against two plant-pathogenic microbes. Compounds 1–6 showed moderate cytotoxicity against the A549 cancer cell line with IC50 values ranging from 6.8 to 35.8 μg mL−1 and were found to be inactive against three other cancer cell lines MCF-7, Caski and Hep G-2.

scholarly journals Cytotoxic Activity-Guided Isolation from Achillea monocephala, and Biological Activities of its Different Extracts

2020 ◽  
Vol 8 (1) ◽  
pp. 7-14
Author(s):  
Turgut Taşkın ◽  
Eray M. Güler ◽  
Şeyda Şentürk ◽  
Damla D. Çelik ◽  
Turan Arabacı ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Cytotoxic Activity ◽  
Antimicrobial Agents ◽  
Biological Activities ◽  
Antimicrobial Activities ◽  
Cytotoxic Activities ◽  
Active Compounds ◽  
Antioxidant Power ◽  
Biological Potential

Background: The genus Achillea is one of the most important genus of the Asteraceae family and many species of Achillea are used in traditional medicine to treat several ailments. Aim: The aim of the current research was to evaluate in vitro cytotoxic activities of n-hexan, chloroform, ethyl acetate and methanol extracts and to isolate the active compounds from the extract showing the strongest cytotoxic activity. In addition to this, it was aimed to evaluate the biological activities (cytotoxic, antioxidant, anti-urease, anticholinesterase, antimicrobial) of different extracts and active compounds from Achillea monocephala. Methods and Materials: The in vitro antioxidant, cytotoxic, anti-urease, anticholinesterase and antimicrobial activities of different extracts from A. monocephala aerial parts were examined. The structures of the active compounds were determined by NMR techniques, UV, IR and LC-MS/MS analysis and their biological potential was examined. Results: The chloroform extract showed strong and selective cytotoxic activity on the cancer cell lines (MDA-MB-231, MCF-7). Besides, this extract exhibited stronger antimicrobial activity than other extracts. Therefore, through activity-guided procedures, luteolin, naringenin and 8-hydroxy-salvigenin compounds were isolated from this extract. The methanol extract showed stronger antioxidant (DPPH, ABTS, CUPRAC) and anticholinesterase activity than other extracts. The n-hexan extract exhibited the highest anti-urease activity. In this study, it was determined that the isolated compounds had a strong biological activity. Naringenin compound had stronger ABTS radical cation scavenging and ferric reducing/antioxidant power, cytotoxic and antimicrobial activity than other compounds. 8-hydroxy-salvigenin compound showed the highest urease and acetylcholinestease enzyme inhibition. Conclusion: The results of this study suggest that the extracts and isolated compounds from the A. monocephala may be used as antioxidant, cytotoxic, anti-urease, anticholinesterase and antimicrobial agents in the future.

scholarly journals Acorenone C: A New Spiro-Sesquiterpene from a Mangrove-Associated Fungus, Pseudofusicoccum sp. J003

2021 ◽  
Vol 9 ◽  
Author(s):  
Shujie Jia ◽  
Xiangdong Su ◽  
Wensi Yan ◽  
Meifang Wu ◽  
Yichuang Wu ◽  
...  
Keyword(s):  
Biological Activities ◽  
Human Tumor ◽  
Antimicrobial Activities ◽  
Culture Broth ◽  
Cytotoxic Activities ◽  
No Production ◽  
Inhibition Rate ◽  
2D Nmr Spectroscopy ◽  
Mangrove Species

Mangrove-derived endophytes are rich in bioactive secondary metabolites with a variety of biological activities. Recently, a fungus Pseudofusicoccum sp. J003 was first isolated by our research group from mangrove species Sonneratia apetala Buch.-Ham. The subsequent chemical investigation of the methanol extract of the culture broth of this strain has led to the isolation of a new sesquiterpenoid named acorenone C (1), two alkaloids (2–3), four phenolic compounds (4–7), and four steroid derivatives (8–11). The new structure of 1 was established by extensive spectroscopic analysis, including 1D, 2D NMR spectroscopy, and HRESIMS. Its absolute configuration was elucidated by experimental ECD and ECD calculation. The in vitro AChE inhibitory, anti-inflammatory, and cytotoxic activities of the selected compounds were evaluated. The results showed that compound 1 showed mild AChE inhibitory activity, with an inhibition rate of 23.34% at the concentration of 50 μM. Compound 9 exerted a significant inhibitory effect against nitric oxide (NO) production in LPS-stimulated RAW 264.7 mouse macrophages, with an inhibition rate of 72.89% at the concentration of 25 μM, better than that of positive control L-NMMA. Compound 9 also displayed obvious inhibition effects on the growth of two human tumor cell lines, HL-60 and SW480 (inhibition rates 98.68 ± 0.97% and 60.40 ± 4.51%, respectively). The antimicrobial activities of the compounds (1–11) against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Pseudomonas aeruginosa were also tested; however, none of them showed antimicrobial activities.

Thiazole: A Privileged Motif in Marine Natural Products

2018 ◽  
Vol 16 (1) ◽  
pp. 26-34 ◽  
Author(s):  
Sunil Kumar ◽  
Ranjana Aggarwal
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Secondary Metabolites ◽  
Marine Natural Products ◽  
Biological Activities ◽  
Thiazole Ring ◽  
Cytotoxic Activities ◽  
Marine Microorganisms ◽  
Thiazole Derivatives ◽  
Drug Leads

Marine natural products have proven to be a rich source of drugs and drug leads. These natural products are secondary metabolites and show biological activity against bacteria, fungi and viruses. Natural products containing thiazole ring occur often in marine sources. They exhibit diverse and remarkable biological activities, including antitumor, antibacterial, anti-inflammatory and cytotoxic activities, to name a few. This review surveys the natural thiazole derivatives that have been isolated from marine microorganisms, with emphasis on biological implications in last three decades.

scholarly journals Different Biological Activities of Histidine-Rich Peptides Are Favored by Variations in Their Design

Toxins ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 363
Author(s):  
Morane Lointier ◽  
Candice Dussouillez ◽  
Elise Glattard ◽  
Antoine Kichler ◽  
Burkhard Bechinger
Keyword(s):  
Biological Activities ◽  
Gene Transfection ◽  
Chemical Properties ◽  
Inverse Correlation ◽  
Antimicrobial Activities ◽  
Limiting Factor ◽  
Endosomal Membrane ◽  
Helical Wheel ◽  
Lentivirus Transduction ◽  
Calcein Release

The protein transduction and antimicrobial activities of histidine-rich designer peptides were investigated as a function of their sequence and compared to gene transfection, lentivirus transduction and calcein release activities. In membrane environments, the peptides adopt helical conformations where the positioning of the histidine side chains defines a hydrophilic angle when viewed as helical wheel. The transfection of DNA correlates with calcein release in biophysical experiments, being best for small hydrophilic angles supporting a model where lysis of the endosomal membrane is the limiting factor. In contrast, antimicrobial activities show an inverse correlation suggesting that other interactions and mechanisms dominate within the bacterial system. Furthermore, other derivatives control the lentiviral transduction enhancement or the transport of proteins into the cells. Here, we tested the transport into human cell lines of luciferase (63 kDa) and the ribosome-inactivating toxin saporin (30 kDa). Notably, depending on the protein, different peptide sequences are required for the best results, suggesting that the interactions are manifold and complex. As such, designed LAH4 peptides assure a large panel of biological and biophysical activities whereby the optimal result can be tuned by the physico-chemical properties of the sequences.

scholarly journals Structural study of new cytotoxic heteroleptic Copper (II) complexes

2014 ◽  
Vol 70 (a1) ◽  
pp. C1229-C1229
Author(s):  
Natalia Alvarez ◽  
Sebastián Iglesias ◽  
Diana Viñas ◽  
María Torre ◽  
Eduardo Kremer ◽  
...  
Keyword(s):  
Cell Lines ◽  
Copper Complexes ◽  
Biological Activities ◽  
Copper Ion ◽  
Chemical Properties ◽  
Metastatic Breast ◽  
Breast Adenocarcinoma ◽  
Phen Ligand ◽  
X Ray Diffraction ◽  
X Ray

The widespread success of Cisplatin in the treatment of several neoplasias has arisen the interest in coordination compounds as drugs for the treatment of cancer. In the search for new compounds with antitumor activity, copper coordination complexes are being studied by our group. This work presents the synthesis and structural characterization of four new copper complexes with general stoichiometry [Cu(L-dipeptide)(phen)]·nH2O and their cytotoxicity against tumor cell lines. Single crystal X-ray diffraction experiments show that the copper ion is situated in a distorted squared pyramidal environment. The phen ligand is perpendicular to the plane defined by the coordinated dipeptide, therefore exposed and potentially available for interaction with biological molecules, e.g. DNA. The availability of the phen ligand and the physico-chemical properties of the complexes are modulated by the dipeptide. Complementary techniques (elemental analysis, infrared and UV-vis spectroscopies) were used to further characterize the complexes in solid state and aqueous solution, confirming that the coordination is maintained in solution. Lipophilicity and DNA binding constants were also measured, being able to discriminate between the behavior of even the complexes containing the ala-phe and phe-ala dipeptide. All the complexes induce cell death in the cell lines of human cervical adenocarcinoma, human metastatic breast adenocarcinoma and human lung epithelial carcinoma. Among the six complexes studied, [Cu(ala-phe)(phen)] presents the lowest half maximal inhibitory concentration (IC50) values. In an attempt to increase the activity, studies are presently being carried out using 2,9-dimethyl-10-phenanthroline. X-ray diffraction studies on the latter show slight deviations in the coordination geometries and different results are expected in their biological activities. Acknoledgements: CSIC, CAPES-UdelaR, PEDECIBA.

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