scholarly journals Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 581
Author(s):  
Vangelis Smyrniotopoulos ◽  
Christian Merten ◽  
Daria Firsova ◽  
Howard Fearnhead ◽  
Deniz Tasdemir
Keyword(s):  
Cell Line ◽  
Brown Seaweed ◽  
Cancer Cell Line ◽  
Structural Diversity ◽  
Chemical Study ◽  
2D Nmr ◽  
Chemical Structures ◽  
Bifurcaria Bifurcata ◽  
Ic50 Values ◽  
Ft Ir

Brown alga Bifurcaria bifurcata is a prolific source of bioactive acyclic (linear) diterpenes with high structural diversity. In the continuation of our investigations on Irish brown algae, we undertook an in-depth chemical study on the n-hexanes and chloroform subextracts of B. bifurcata that led to isolation of six new (1–6) and two known (7–8) acyclic diterpenes. Chemical structures of the compounds were elucidated by a combination of 1D and 2D NMR, HRMS, FT-IR, [α]D and vibrational circular dichroism (VCD) spectroscopy. Compounds 1–8, as well as three additional linear diterpenes (9–11), which we isolated from the same seaweed before, were tested against the human breast cancer cell line (MDA-MB-231). Several compounds moderately inhibited the growth of the MDA-MB-231 cell line with IC50 values ranging from 11.6 to 32.0 μg/mL. The present study carried out on the lipophilic extracts of the Irish B. bifurcata shows the enormous capacity of this seaweed to produce a large palette of acyclic diterpenes with diverse oxygenation and substitution patterns and promising bioactivities.

scholarly journals Density Functional Theory (DFT)-Aided Structure Elucidation of Linear Diterpenes from the Irish Brown Seaweed Bifurcaria bifurcata

Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 42
Author(s):  
Vangelis Smyrniotopoulos ◽  
Daria Firsova ◽  
Howard Fearnhead ◽  
Laura Grauso ◽  
Alfonso Mangoni ◽  
...  
Keyword(s):  
Density Functional ◽  
Chemical Shifts ◽  
Optical Rotation ◽  
Brown Seaweed ◽  
Cancer Cell Line ◽  
Structural Diversity ◽  
2D Nmr ◽  
Bifurcaria Bifurcata ◽  
Chcl3 Extract ◽  
Ic50 Values

Brown alga Bifurcaria bifurcata is an extraordinarily rich source of linear (acylic) diterpenes with enormous structural diversity. As part of our interest into secondary metabolites of the Irish seaweeds, here we report four new acyclic diterpenes (1–4) and seven known terpenoids (5–11) from the CHCl3 extract of B. bifurcata. The planar structures of the new metabolites were elucidated by means of 1D and 2D NMR, HRMS, and FT-IR spectroscopy. Since linear diterpenes are highly flexible compounds, the assignment of their stereochemistry by conventional methods, e.g., NOESY NMR, is difficult. Therefore, we employed extensive quantum-mechanical prediction of NMR chemical shifts and optical rotation analyses to identify the relative and absolute configurations of the new compounds 1–4. Several compounds moderately inhibited the human breast cancer cell line (MDA-MB-231) with IC50 values ranging from 10.0 to 33.5 μg/mL. This study not only demonstrates the vast capacity of the Irish B. bifurcata to produce highly oxygenated linear diterpenoids, but also highlights the potential of new methodologies for assignment of their stereogenic centers.

scholarly journals Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087

Marine Drugs ◽  
2020 ◽  
Vol 18 (6) ◽  
pp. 281
Author(s):  
Bicheng Fan ◽  
Pradeep Dewapriya ◽  
Fengjie Li ◽  
Laura Grauso ◽  
Martina Blümel ◽  
...  
Keyword(s):  
Cell Line ◽  
Acid Derivative ◽  
Optical Rotation ◽  
Chemical Study ◽  
2D Nmr ◽  
Human Malignant Melanoma ◽  
Chemical Structures ◽  
Isolation And Characterization ◽  
Ic50 Values ◽  
Fungal Genus

The fungal genus Pyrenochaetopsis is commonly found in soil, terrestrial, and marine environments, however, has received little attention as a source of bioactive secondary metabolites so far. In a recent work, we reported the isolation and characterization of three new anticancer decalinoyltetramic acid derivatives, pyrenosetins A–C, from the Baltic Fucus vesiculosus-derived endophytic fungus Pyrenochaetopsis sp. FVE-001. Herein we report a new pentacyclic decalinoylspirotetramic acid derivative, pyrenosetin D (1), along with two known decalin derivatives wakodecalines A (2) and B (3) from another endophytic strain Pyrenochaetopsis FVE-087 isolated from the same seaweed and showed anticancer activity in initial screenings. The chemical structures of the purified compounds were elucidated by comprehensive analysis of HR-ESIMS, FT-IR, [α]D, 1D and 2D NMR data coupled with DFT calculations of NMR parameters and optical rotation. Compounds 1–3 were evaluated for their anticancer and toxic potentials against the human malignant melanoma cell line (A-375) and the non-cancerous keratinocyte cell line (HaCaT). Pyrenosetin D (1) showed toxicity towards both A-375 and HaCaT cells with IC50 values of 77.5 and 39.3 μM, respectively, while 2 and 3 were inactive. This is the third chemical study performed on the fungal genus Pyrenochaetopsis and the first report of a pentacyclic decalin ring system from the fungal genus Pyrenochaetopsis.

Antidiabetic and Anticholinesterase Properties of Extracts and Pure Metabolites of Fruit Stems of Pistachio (Pistacia vera L.)

2020 ◽  
Vol 24 (7) ◽  
pp. 785-797
Author(s):  
Yabo Dambagi Lawali ◽  
Akyuz Mehmet ◽  
Aydin Tuba ◽  
Cakir Ahmet
Keyword(s):  
Shikimic Acid ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Ft Ir ◽  
High Concentrations ◽  
Ethanol Extracts ◽  
Anticholinesterase Properties

: Five metabolites were isolated by chromatographic methods from the fruit stems of P. vera and their chemical structures were characterized as masticadienonic acid (1), tirucallol (2), masticadienolic acid (3), pistachionic acid (4) and inulobiose (5) via FT-IR, 1H-NMR, 13C-NMR, 1D-NMR and 2D-NMR. Pistachionic acid (4), a new shikimic acid derivative, was isolated from the ethanol extract for the first time. The hexane, chloroform, ethanol extracts and pure metabolites exhibited antidiabetic properties by inhibiting α- glycosidase and α-amylase enzymes at different rates. Their inhibitory effects against the α- glycosidase enzyme were also higher than that of the acarbose (IC50=10.30 mg/mL). Masticadienolic acid (3) (IC50=0.03 mg/mL), masticadienonic acid (1) (IC50=0.13 mg/mL) and hexane extract (IC50=0.09 mg/mL) with the lowest IC50 values were found to be most active substances. Nevertheless, the inhibitory effect of acarbose against the α-amylase enzyme was determined to be higher than the inhibition effects of the extracts and pure metabolites. According to the IC50 values, the best inhibitors against the α-amylase were ethanol extract (IC50=5.17 mg/mL), pistachionic acid (4) (IC50=7.35 mg/mL), tirucallol (2) (IC50=7.58 mg/mL) and masticadienolic acid (3) (IC50=8.22 mg/mL), respectively among the applications. In addition, anticholinesterase properties of the extracts and pure metabolites were investigated by testing the inhibitory properties against acetylcholine esterase (AChE) and butrylcholine esterase (BChE) enzymes activities. The results showed that the anticholinesterase properties of all extracts and pure metabolites were weaker than those of the commercial cholinesterase inhibitors, neostigmine and galantamine, and all applications reduced the activity of these enzymes at very high concentrations.

scholarly journals New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 167 ◽  
Author(s):  
Pierre-Eric Campos ◽  
Emmanuel Pichon ◽  
Céline Moriou ◽  
Patricia Clerc ◽  
Rozenn Trépos ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Minimum Inhibitory Concentration ◽  
Marine Sponge ◽  
Nmr Spectra ◽  
Inhibitory Concentration ◽  
Chemical Study ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
2D Nmr Spectra ◽  
Ic50 Values

Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.

scholarly journals Investigation of the key chemical structures involved in the anticancer activity of disulfiram in A549 non-small cell lung cancer cell line

BMC Cancer ◽  
2018 ◽  
Vol 18 (1) ◽  
Author(s):  
Kate Butcher ◽  
Vinodh Kannappan ◽  
Rajagopal Sharada Kilari ◽  
Mark R. Morris ◽  
Christopher McConville ◽  
...  
Keyword(s):  
Lung Cancer ◽  
Small Cell Lung Cancer ◽  
Anticancer Activity ◽  
Cell Line ◽  
Cancer Cell Line ◽  
Lung Cancer Cell Line ◽  
Small Cell ◽  
Lung Cancer Cell ◽  
Small Cell Lung ◽  
Chemical Structures

IN-SILICO AND IN VITRO ASSESSMENT OF SYNTHESIZED DIAZENYLSULFONAMIDES AS APOPTOSIS INDUCERS AND RADICAL SCAVENGERS

INDIAN DRUGS ◽  
2020 ◽  
Vol 57 (06) ◽  
pp. 49-59
Author(s):  
Priyambada Kshiroda Nandini Sarangi ◽  
Jyotirmaya Sahoo ◽  
Chita Ranjan Sahoo ◽  
Sudhir Kumar Paidesetty ◽  
Guru Prasad Mohanta
Keyword(s):  
Cell Line ◽  
Cancer Cell ◽  
Radical Scavenging ◽  
Cancer Cell Line ◽  
Scavenging Effect ◽  
Ic50 Values ◽  
Radical Scavenging Effect ◽  
The Individual ◽  
Mcf 7

A series of eight quinoline-thiazole hybrid-bearing diazenylsulfonamides, 4a-4h, were synthesized and characterized by UV-Vis, FT/IR, 1H NMR and lC-MS. These compounds were formed when two prepared intermediate precursors of Schiff-base compounds, (E)-N-((2-chloroquinolin-3-yl)methylene)-4phenylthiazol-2-amine (3a) and (E)-N-((2-chloroquinolin-3-yl)methylene)-4-chlorophenylthiazol-2-amine (3b) were converted to the corresponding diazenyl compounds 4a-4h by treating and coupling with the individual diazonium salts of sulfa-drugs. The results of in vitro cytotoxic activity of the synthesized compounds in two cancer cell lines MCF 7 (human breast cancer cell line) and K562 (myelogenousleukemia cell line) have shown the IC50 values as given: 4b against MCF 7 19.52 and against K562 20.55µM; 4d against MCF 7 15.96 and against K562 13.05µM. Moreover, the compound 4-(((Z)-(2-chloroquinolin-3yl)(4-phenylthiazol-2-ylimino)methyl)diazenyl)benzenesulfonic acid (4d) induced maximum percentage of apoptosis. Furthermore, the in vitro antioxidant activity study revealed that among all the synthesized compounds, compound 4d has an excellent radical scavenging effect. Molecular docking was additionally performed to investigate the binding affinity of H-bonding interaction of synthesized compounds with a targeted enzyme and to compare it with the anticancer drugs, dasatinib, bosutinib and dacarbazine.

scholarly journals New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 439 ◽  
Author(s):  
Li ◽  
Peifer ◽  
Janussen ◽  
Tasdemir
Keyword(s):  
Anticancer Activity ◽  
Deep Sea ◽  
Topoisomerase I ◽  
Active Sites ◽  
Binding Potential ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Ft Ir ◽  
The Antarctic

The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (−)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (−)-2-bromo-discorhabdin D (4), (−)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1–6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1–6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids.

scholarly journals Anticancer Activities of Chemical Constituents from Leaves and Twigs of Mitrephora winitii

2021 ◽  
Vol 21 (3) ◽  
pp. 699
Author(s):  
Sukee Sukdee ◽  
Puttinan Meepowpan ◽  
Narong Nantasaen ◽  
Siriporn Jungsuttiwong ◽  
Sarinya Hadsadee ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Chemical Constituents ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Anticancer Activities ◽  
Chromatographic Separations ◽  
Chemical Structures ◽  
Anti Cancer ◽  
First Time ◽  
Mcf 7

The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.

scholarly journals Green synthesis of silver nanoparticles by Aspergillus consortium and evaluating its anticancer activity against Human breast adenocarcinoma cell line (MCF7)

2017 ◽  
Vol 4 (1) ◽  
pp. 28 ◽  
Author(s):  
Rajeswari P. ◽  
Samuel P. ◽  
Vijayakumar J. ◽  
Selvarathinam T. ◽  
Sudarmani D.N.P. ◽  
...  
Keyword(s):  
Silver Nanoparticles ◽  
Anticancer Activity ◽  
Cell Line ◽  
Tamil Nadu ◽  
Breast Adenocarcinoma ◽  
Metallic Silver ◽  
Ic50 Values ◽  
Mcf7 Cell Line ◽  
Ft Ir ◽  
Cell Inhibition

Objective: The objective of the present study is to produce silver nanoparticles from marine fungi from south west coastal areas of Tamil Nadu and evaluating their potentials with special reference to anticancer activity.Methods: Hand core pushing technique is adapted to collect marine sediment samples along the coastal environs. Distinguished Aspergillus colonies were isolated and identified by wet mount procedure. The characterized Aspergillus consortium was subjected to produce silver nanoparticles. The extracellularly synthesized nanoparticles were characterized. Silver nanoparticles were evaluated for anticancer activity against MCF7 cell line by MTT assay. The IC50 values were determined.Results: Aspergillus consortium consist of A. niger, A. michelle and A. japonicus. Silver nanoparticles were extracellularly synthesized by the reduction of silver nitrate (AgNO3) to metallic silver (Ag+) ions results in the transformation of pale yellow to dark red colour. Constant shift was observed at 420 nm while monitoring the solution by UV-Vis spectrophotometer. The presence of important functional groups like –NH3 was confirmed by FT-IR Spectroscopy. Anticancer activity of the silver nanoparticles was evaluated against MCF7. There was 100% cell inhibition when concentration of the AgNPs reached 25 µg, 50 µg and 100 µg respectively in the test solution. Notably the IC50 value was found to be very lowest for the nanoparticles produced by A. japonicus and the value was found to be 1.47 µg/ml.Conclusions: Aspergillus consortium was found to be an ideal mycobiosystem for the production of silver nanoparticles with potential anticancer activity.

scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

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