Holospiniferoside: A New Antitumor Cerebroside from The Red Sea Cucumber Holothuria spinifera: In Vitro and In Silico Studies

Chemical investigation of the methanolic extract of the Red Sea cucumber Holothuria spinifera led to the isolation of a new cerebroside, holospiniferoside (1), together with thymidine (2), methyl-α-d-glucopyranoside (3), a new triacylglycerol (4), and cholesterol (5). Their chemical structures were established by NMR and mass spectrometric analysis, including gas chromatography–mass spectrometry (GC–MS) and high-resolution mass spectrometry (HRMS). All the isolated compounds are reported in this species for the first time. Moreover, compound 1 exhibited promising in vitro antiproliferative effect on the human breast cancer cell line (MCF-7) with IC50 of 20.6 µM compared to the IC50 of 15.3 µM for the drug cisplatin. To predict the possible mechanism underlying the cytotoxicity of compound 1, a docking study was performed to elucidate its binding interactions with the active site of the protein Mdm2–p53. Compound 1 displayed an apoptotic activity via strong interaction with the active site of the target protein. This study highlights the importance of marine natural products in the design of new anticancer agents.

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New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies

Marine Drugs ◽

10.3390/md18080405 ◽

2020 ◽

Vol 18 (8) ◽

pp. 405

Author(s):

Reda F. A. Abdelhameed ◽

Enas E. Eltamany ◽

Dina M. Hal ◽

Amany K. Ibrahim ◽

Asmaa M. AboulMagd ◽

...

Keyword(s):

Red Sea ◽

Sea Cucumber ◽

Breast Adenocarcinoma ◽

Cytotoxic Activities ◽

Cholesterol Sulfate ◽

Standard Drug ◽

Chemical Structures ◽

In Silico Studies ◽

Red Sea Cucumber ◽

Mcf 7

Bioactivity-guided fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera extract indicated the presence of diverse secondary metabolites, mostly hydroxy fatty acids, diterpenes, triterpenes, and cerebrosides. The isolated compounds were tested for their in vitro cytotoxicities against the breast adenocarcinoma MCF-7 cell line. Compounds 1, 2, 3, and 4 displayed promising cytotoxic activities against MCF-7 cells, with IC50 values of 13.83, 8.13, 8.27, and 35.56 µM, respectively, compared to that of the standard drug doxorubicin (IC50 8.64 µM). Additionally, docking studies were performed for compounds 1, 2, 3, and 4 to elucidate their binding interactions with the active site of the SET protein, an inhibitor of protein phosphatase 2A (PP2A), which could explain their cytotoxic activity. This study highlights the important role of these metabolites in the defense mechanism of the sea cucumber against fouling organisms and the potential uses of these active molecules in the design of new anticancer agents.

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Characterization of drug interferences caused by coelution of substances in gas chromatography/mass spectrometry confirmation of targeted drugs in full-scan and selected-ion monitoring modes

Clinical Chemistry ◽

10.1093/clinchem/40.2.216 ◽

1994 ◽

Vol 40 (2) ◽

pp. 216-220 ◽

Cited By ~ 16

Author(s):

A H Wu ◽

D Ostheimer ◽

M Cremese ◽

E Forte ◽

D Hill

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography Mass Spectrometry ◽

Spectrometric Analysis ◽

Targeted Drugs ◽

Selected Ion Monitoring ◽

Internal Standards ◽

Target Drug ◽

Full Scan ◽

Chromatographic Mass

Abstract Interference by substances coeluting with targeted drugs is a general problem for gas chromatographic/mass spectrometric analysis of urine. To characterize these interferences, we examined human urine samples containing benzoylecgonine and fluconazole, and other drug combinations including deuterated internal standards that coelute (ISd,c) with target drugs, by selected-ion monitoring (SIM) and full-scan mass spectrometry. We show that, by SIM analysis, detecting the presence of an interferent is dependent on the specific IS used for the assay. When an ISd,c is used, the presence of another coeluting substance (interferent) suggests that the intensity of IS ions is substantially diminished, because the interferent affects both the ISd,c and target drug. When a noncoeluting IS (ISnc) is used, the interferent cannot be discerned unless it coincidently contains one or more of the ions monitored for either the target drug or ISnc. Under full-scan analysis, a coeluting interferent is directly discernable by examining the total ion gas chromatogram.

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Therapeutic Potentials of Syzygium fruticosum Fruit (Seed) Reflected into an Array of Pharmacological Assays and Prospective Receptors-Mediated Pathways

Life ◽

10.3390/life11020155 ◽

2021 ◽

Vol 11 (2) ◽

pp. 155

Author(s):

Jannatul Nasma Rupa Moni ◽

Md. Adnan ◽

Abu Montakim Tareq ◽

Md. Imtiazul Kabir ◽

A.S.M. Ali Reza ◽

...

Keyword(s):

Bioactive Compounds ◽

Integrated Approach ◽

Gas Chromatography Mass Spectrometry ◽

Clot Lysis ◽

Lipinski’S Rule ◽

Lysis Activity ◽

In Silico Studies ◽

Immobility Time

Syzygium fruticosum (SF), a valuable Bangladeshi fruit, is considered an alternative therapeutic agent. Mainly, seeds are used as nutritional phytotherapy to ease physical and mental status by preventing chronic diseases. Here, we scrutinized the S. fruticosum seed’s fundamental importance in traditional medicine by following an integrated approach combining in vivo, in vitro, and in silico studies. The SF was fractionated with different solvents, and the ethyl acetate fraction of SF (EaF-SF) was further studied. Mice treated with EaF-SF (200 and 400 mg/kg) manifested anxiolysis evidenced by higher exploration in elevated plus maze and hole board tests. Similarly, a dose-dependent drop of immobility time in a forced swimming test ensured significant anti-depressant activity. Moreover, higher dose treatment exposed reduced exploratory behaviour resembling decreased movement and prolonged sleeping latency with a quick onset of sleep during the open field and thiopental-induced sleeping tests, respectively. In parallel, EaF-SF significantly (p < 0.001) and dose-dependently suppressed acetic acid and formalin-induced pain in mice. Also, a noteworthy anti-inflammatory activity and a substantial (p < 0.01) clot lysis activity (thrombolytic) was observed. Gas chromatography-mass spectrometry (GC–MS) analysis resulted in 49 bioactive compounds. Among them, 12 bioactive compounds with Lipinski’s rule and safety confirmation showed strong binding affinity (molecular docking) against the receptors of each model used. To conclude, the S. fruticosum seed is a prospective source of health-promoting effects that can be an excellent candidate for preventing degenerative diseases.

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Identifying volatile in vitro biomarkers for oral bacteria with proton-transfer-reaction mass spectrometry and gas chromatography–mass spectrometry

Scientific Reports ◽

10.1038/s41598-021-96287-7 ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Kajsa Roslund ◽

Markku Lehto ◽

Pirkko Pussinen ◽

Kari Hartonen ◽

Per-Henrik Groop ◽

...

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Proton Transfer ◽

Transfer Reaction ◽

Proton Transfer Reaction ◽

Oral Bacteria ◽

Gas Chromatography Mass Spectrometry ◽

Volatile Analysis ◽

Bacterial Volatiles

AbstractWe have measured the volatile fingerprints of four pathogenic oral bacteria connected to periodontal disease and dental abscess: Porphyromonas gingivalis (three separate strains), Prevotella intermedia, Prevotella nigrescens and Tannerella forsythia. Volatile fingerprints were measured in vitro from the headspace gas of the bacteria cultured on agar. Concrete identification of new and previously reported bacterial volatiles were performed by a combination of solid phase microextraction (SPME) and offline gas chromatography–mass spectrometry (GC–MS). We also studied the effect of the reduced electric field strength (E/N) on the fragmentation patterns of bacterial volatiles in online proton-transfer-reaction time-of-flight mass spectrometry (PTR-ToF-MS). We aimed to discover possible new biomarkers for the studied oral bacteria, as well as to validate the combination of GC–MS and PTR-MS for volatile analysis. Some of the most promising compounds produced include: 1-Methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ), indole, and a cascade of sulphur compounds, such as methanethiol, dimethyl disulphide (DMDS) and dimethyl trisulphide (DMTS). We also found that several compounds, especially alcohols, aldehydes and esters, fragment significantly with the PTR-MS method, when high E/N values are used. We conclude that the studied oral bacteria can be separated by their volatile fingerprints in vitro, which could have importance in clinical and laboratory environments. In addition, using softer ionization conditions can improve the performance of the PTR-MS method in the volatile analysis of certain compounds.

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Gas chromatography-mass spectrometry fingerprint and in vitro cytotoxic studies of Rubus steudneri leaf fractions against michigan cancer foundation-7 breast cancer cell line

Pharmacognosy Magazine ◽

10.4103/pm.pm_324_20 ◽

2021 ◽

Vol 17 (5) ◽

pp. 54

Author(s):

RaghavendraLakshmana Shetty Hallur ◽

ChaitanyaV. N L. Motamarri ◽

PrashithKekuda T. Ramamoorthy ◽

ChetanD Murthy ◽

RavikumarPatil H. Siddappa ◽

...

Keyword(s):

Breast Cancer ◽

Mass Spectrometry ◽

Gas Chromatography ◽

Cell Line ◽

Breast Cancer Cell ◽

Breast Cancer Cell Line ◽

Cancer Cell Line ◽

Gas Chromatography Mass Spectrometry ◽

Cytotoxic Studies

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Evaluation of Costus afer Ker Gawl. in vitro anti-inflammatory activity and its chemical constituents identified using gas chromatography-mass spectrometry analysis

Journal of Coastal Life Medicine ◽

10.12980/jclm.3.2015apjtb-2014-0186 ◽

2015 ◽

Cited By ~ 1

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Chemical Constituents ◽

Inflammatory Activity ◽

Mass Spectrometry Analysis ◽

Gas Chromatography Mass Spectrometry ◽

Spectrometry Analysis ◽

Chromatography Mass Spectrometry ◽

Costus Afer

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Pharmacological perspectives from Brazilian Salvia officinalis (Lamiaceae): antioxidant, and antitumor in mammalian cells

Anais da Academia Brasileira de Ciências ◽

10.1590/0001-3765201520150344 ◽

2016 ◽

Vol 88 (1) ◽

pp. 281-292 ◽

Cited By ~ 26

Author(s):

CHARLENE S.C. GARCIA ◽

CAROLINE MENTI ◽

ANA PAULA F. LAMBERT ◽

THIAGO BARCELLOS ◽

SIDNEI MOURA ◽

...

Keyword(s):

Mass Spectrometry ◽

Mammalian Cells ◽

Annexin V ◽

The Body ◽

Salvia Officinalis ◽

Gas Chromatography Mass Spectrometry ◽

Ionization Mass ◽

Hek 293 ◽

Salvia Officinalis L

ABSTRACT Salvia officinalis (Lamiaceae) has been used in south of Brazil as a diary homemade, in food condiment and tea-beverage used for the treatment of several disorders. The objective of this study was to characterize chemical compounds in the hydroalcoholic (ExtHS) and aqueous (ExtAS) extract from Salvia officinalis (L.) by gas chromatography-mass spectrometry (GC-MS) and by high-resolution electrospray ionization mass spectrometry (ESI-QTOF MS/MS), evaluate in vitro ability to scavenge the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+), catalase (CAT-like) and superoxide dismutase (SOD-like) activity, moreover cytotoxic by MTT assay, alterations on cell morphology by giemsa and apoptotic-induced mechanism for annexin V/propidium iodide. Chemical identification sage extracts revealed the presence of acids and phenolic compounds. In vitro antioxidant analysis for both extracts indicated promising activities. The cytotoxic assays using tumor (Hep-2, HeLa, A-549, HT-29 and A-375) and in non-tumor (HEK-293 and MRC-5), showed selectivity for tumor cell lines. Immunocytochemistry presenting a majority of tumor cells at late stages of the apoptotic process and necrosis. Given the results presented here, Brazilian Salvia officinalis (L.) used as condiment and tea, may protect the body against some disease, in particularly those where oxidative stress is involved, like neurodegenerative disorders, inflammation and cancer.

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