Densazalin, a New Cytotoxic Diazatricyclic Alkaloid from the Marine Sponge Haliclona densaspicula

Densazalin, a polycyclic alkaloid, was isolated from the marine sponge Haliclona densaspicula collected in Korea. The complete structure of the compound was determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance techniques, high-resolution mass spectrometry, and comparison of the calculated and measured electronic circular dichroism spectra. Densazalin possesses a unique 5,11-diazatricyclo[7.3.1.02,7]tridecan-2,4,6-triene moiety, which is connected by two linear carbon chains. This compound was derived from the biogenetic precursor bis-1,3-dialkylpyridnium. Densazalin exhibited cytotoxic activity on two human tumor cell lines (AGS and HepG2) in the Cell Counting Kit-8 (CCK-8) bioassay, with IC50 values ranging from 15.5 to 18.4 μM.

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Unique Polyhalogenated Peptides from the Marine Sponge Ircinia sp.

Marine Drugs ◽

10.3390/md18080396 ◽

2020 ◽

Vol 18 (8) ◽

pp. 396

Author(s):

Rogelio Fernández ◽

Asep Bayu ◽

Tri Aryono Hadi ◽

Santiago Bueno ◽

Marta Pérez ◽

...

Keyword(s):

Marine Sponge ◽

Topoisomerase I ◽

Human Tumor ◽

2D Nmr ◽

Amino Acid Residues ◽

Human Tumor Cell ◽

2D Nmr Spectroscopy ◽

Human Tumor Cell Lines ◽

Thousand Islands ◽

Cell Death Protein

Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), have been isolated from an Indonesian marine sponge of the genus Ircinia collected in the Thousand Islands (Indonesia). The planar structure of both compounds was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of Marfey’s method. Compound 1 is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound 2 is a rare peptide possessing a tribromopyrrole ring. Both compounds failed to show significant cytotoxicity against four human tumor cell lines, and neither compound was able to inhibit the enzyme topoisomerase I or impair the interaction between programmed cell death protein PD1 and its ligand, PDL1.

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Synthesis and Antitumor Activity of (3-Hydroxyacrylato-O,O′) Diammineplatinum(II)

Pharmaceutical Fronts ◽

10.1055/s-0041-1730956 ◽

2021 ◽

Vol 03 (01) ◽

pp. e13-e17

Author(s):

Yong-Zhi Shu ◽

Jun Lin ◽

Bao-Quan Zhu ◽

Quan-Hai Liu ◽

Bin Zhou ◽

...

Keyword(s):

Antitumor Activity ◽

Cancer Treatment ◽

High Resolution Mass Spectrometry ◽

Human Tumor ◽

Human Tumor Cell Lines ◽

Control Drug ◽

S180 Sarcoma ◽

Ic50 Values ◽

Hct 116

AbstractAs an indispensable part of cancer chemotherapy, platinum drugs still play an important role in cancer treatment. In this study, two platinum(II) complexes with Michael acceptor 3-hydroxyacrylic acid as the leaving group were synthesized from cis-diamminediiodo platinum(II) and 3-ethoxyacrylic acid. The structures of complexes 1 and 2 were confirmed by elemental analysis, infrared, 1H NMR, 13C NMR, and HRMS (high-resolution mass spectrometry). Results from MTT assay showed that complexes 1 and 2 significantly inhibited the growth of the four human tumor cell lines (HCT-116, A549, CFPAC-1, and BxPC-3) with the IC50 values of the two compounds similar to that of the control drug (oxaliplatin) on HCT-116 and A549. Besides, results from an in vivo study in a mouse S180 sarcoma model showed that complex 1 had a higher antitumor activity in comparison to oxaliplatin. In conclusion, our article indicated that complex 1 deserved further research and development in cancer treatment.

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Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

Rodriguésia ◽

10.1590/2175-7860202071050 ◽

2020 ◽

Vol 71 ◽

Author(s):

Fernando Duarte Cabral ◽

Cassia Cristina Fernandes ◽

Arthur Barcelos Ribeiro ◽

Iara Squarisi Squarisi ◽

Denise Crispim Tavares ◽

...

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Normal Cell ◽

Human Tumor ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Ic50 Values ◽

Mcf 7

Abstract This paper aims to investigate, for the first time, in vitro antitubercular, antileishmanial and antiproliferative activities of essential oils (EOs) from S. odoratissima leaves and flowers - grown in midwestern Brazil - against Mycobacterium tuberculosis, promastigote forms of Leishmania amazonensis and human tumor cell lines. Antimycobacterial activity of EOs was evaluated in terms of the minimal inhibitory concentration (MIC). EOs from leaves and flowers showed to be active antimicrobials against M. tuberculosis, since MIC values were 150 µg/mL and 162.5 µg/mL, respectively. Both EOs exhibited significant activity against promastigote forms of L. amazonensis; IC50 values (50% growth inhibition) were 14.36 ± 2.02 (EOs from leaves) and 19.89 ± 2.66 µg/mL (EOs from flowers). Antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumor (MCF-7, HeLa and M059J) cell lines was performed by the XTT assay; results were expressed as IC50 (50% cell growth inhibition) and the selective index was calculated. IC50 values of EOs from leaves and flowers obtained in normal cell lines for were 502.97 ± 40.33 µg/mL and 370.60 ± 2.01 µg/mL, respectively. Antiproliferative activity was observed against human tumor cell lines, whose IC50 values were significantly lower than those obtained in normal cell lines of MCF-7 cells (367.57 ± 4.46 µg/mL-EOs from leaves and 357.70 ± 1.85 µg/mL-EOs from flowers) and M059J cells (492.53 ± 56.67 µg/mL-EOs from leaves and 324.90 ± 6.72 µg/mL-EOs from flowers), thus, indicating selectivity. These in vitro results showed that EOs from S. odoratissima may be an antimycobacterial, antiparasitic and antitumor agent.

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Five New Meroterpenoids from the Fruiting Bodies of the Basidiomycete Clitocybe clavipes with Cytotoxic Activity

Molecules ◽

10.3390/molecules24224015 ◽

2019 ◽

Vol 24 (22) ◽

pp. 4015 ◽

Cited By ~ 3

Author(s):

Zhaocui ◽

Xudong ◽

Hanqiao ◽

Xinyi ◽

Guoxu ◽

...

Keyword(s):

Tumor Cell ◽

Cytotoxic Activity ◽

Cell Lines ◽

Human Tumor ◽

Tumor Cell Lines ◽

Fruiting Bodies ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Ic50 Values

Five new meroterpenoids, clavipols A–B (1–2) with a 12-membered ether ring and clavilactones G–I (3–5) having a 10-membered carbocycle connected to a hydroquinone and an α,β-epoxy/unsaturated lactone, were obtained from the fruiting bodies of the basidiomycete Clitocybe clavipes. Their structures were determined by comprehensive analysis of their spectroscopic data, and the absolute configuration of 1 was established by quantum chemical calculations of electronic circular dichroism (ECD). All the isolated compounds (1–5) were tested for their cytotoxic activity against three human tumor cell lines (Hela, SGC-7901, and SHG-44) in vitro after treatment for 48 h. Compound 4 exhibited moderate cytotoxic activity against Hela and SGC-7901 tumor cell lines, with IC50 values of 23.5 and 14.5 µM, respectively.

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New Cytotoxic Cycloartane Triterpenes from the Aerial Parts of Actaea heracleifolia (syn. Cimicifuga heracleifolia)

Planta Medica ◽

10.1055/a-0733-7229 ◽

2018 ◽

Vol 85 (02) ◽

pp. 154-159

Author(s):

Qiang-Qiang Shi ◽

Wei-Hua Wang ◽

Jing Lu ◽

Da-Shan Li ◽

Lin Zhou ◽

...

Keyword(s):

Cell Lines ◽

Human Tumor ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Chemical Structures ◽

Aerial Parts ◽

Ic50 Values ◽

Weak Activity ◽

Mcf 7

AbstractOne new 15,16-seco-cycloartane triterpene (1), three new cycloartane triterpene glycosides (2–4), and five known compounds (5–9) were isolated from the aerial parts of Actaea heracleifolia. The chemical structures of these compounds were determined on the basis of NMR analysis, HRTOF-ESIMS data, and other spectroscopic methods. Selected compounds were evaluated for their cytotoxicity against human tumor cell lines (HL-60, SMMC-7721, A549, MCF-7, and SW480) in vitro. Compounds 3 and 4 showed weak activity against the HL-60, A-549, and MCF-7 cell lines with IC50 values ranging from 21.34 to 36.98 µM.

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Two New Cytotoxic Maytansinoids Targeting Tubulin from Trewia nudiflora

Planta Medica ◽

10.1055/a-1530-1128 ◽

2021 ◽

Author(s):

Chun Lei ◽

Ya-Nan Li ◽

Jia-Nan Li ◽

Yu-Bo Zhou ◽

Ming-Jun Cui ◽

...

Keyword(s):

Human Tumor ◽

Crystallographic Analysis ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

X Ray ◽

Trewia Nudiflora ◽

Ic50 Values ◽

Mcf 7

AbstractTwo new maytansinoids, N-methyltreflorine (1) and methyltrewiasine (2), were isolated from the dried fruits of Trewia nudiflora, together with three known congeners (3 – 5). Their structures were elucidated by spectroscopic methods, and the absolute configuration of 1 and 2 was determined by X-ray crystallographic analysis. Compounds 1 – 5 exhibited strong cytotoxicity against human tumor cell lines, including HeLa, MV-4 – 11, and MCF-7, with IC50 values ranging from 0.12 to 11 nM. Compounds 1 and 4 also showed inhibitory activity against the MCF-7/ADR cell line with IC50 values of 13 and 28 nM, respectively. Compounds 1 and 2 significantly inhibited tubulin polymerization in vitro with IC50 values of 3.6 and 3.2 µM, respectively.

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Differential Increases in Glutathione S-Transferase Activities in a Range of Multidrug-Resistant Human Tumor Cell Lines

Cancer Communications ◽

10.3727/095535489820875057 ◽

1989 ◽

Vol 1 (6) ◽

pp. 359-365 ◽

Cited By ~ 36

Author(s):

Richard D. H. Whelan ◽

Louise K. Hosking ◽

Alan J. Townsend ◽

Kenneth H. Cowan ◽

Bridget T. Hill

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Human Tumor ◽

Multidrug Resistant ◽

Tumor Cell Lines ◽

Glutathione S Transferase ◽

Human Tumor Cell ◽

Human Tumor Cell Lines

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Synthesis and Cytotoxicity of New Mannich Bases of 6-[3-(3,4,5-Trimetoxyphenyl)-2- propenoyl]-2(3H)-Benzoxazolone

Letters in Drug Design & Discovery ◽

10.2174/1570180816666190730164952 ◽

2020 ◽

Vol 17 (4) ◽

pp. 512-517

Author(s):

Ognyan Ivanov Petrov ◽

Yordanka Borisova Ivanova ◽

Mariana Stefanova Gerova ◽

Georgi Tsvetanov Momekov

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Biological Activities ◽

Human Tumor ◽

Mannich Bases ◽

In Vitro Cytotoxicity ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Human Tumor Cell Lines

Background: Chemotherapy is one of the mainstays of cancer treatment, despite the serious side effects of the clinically available anticancer drugs. In recent years increasing attention has been directed towards novel agents with improved efficacy and selectivity. Compounds with chalcone backbone have been reported to possess various biological activities such as anticancer, antimicrobial, anti-inflammatory, analgesic, antioxidant, etc. It was reported that aminomethylation of hydroxy chalcones to the corresponding Mannich bases increased their cytotoxicity. In this context, our interest has been focused on the design and synthesis of the so-called multi-target molecules, containing two or more pharmacophore fragments. Methods: A series of Mannich bases were synthesized by the reaction between 6-[3-(3,4,5- trimethoxyphenyl)-2-propenoyl]-2(3Н)-benzoxazolone, formaldehyde, and a secondary amine. The structures of the compounds were confirmed by elemental analysis, IR and NMR spectra. The new Mannich bases were evaluated for their in vitro cytotoxicity against a panel of human tumor cell lines, including BV-173, SKW-3, K-562, HL-60, HD-MY-Z and MDA-MB-231. The effects of selected compounds on the cellular levels of glutathione (GSH) were determined. Results: The new compounds 4a-e exhibited concentration-dependent cytotoxic effects at micromolar concentrations in MTT-dye reduction assay against a panel of human tumor cell lines, similar to those of starting chalcone 3. The tested agents led to concentration - dependent depletion of cellular GSH levels, whereby the effects of the chalcone prototype 3 and its Mannich base-derivatives were comparable. Conclusion: The highest chemosensitivity to the tested compounds was observed in BV- 173followed by SKW-3 and HL-60 cell lines.

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Setosphlides A–D, New Isocoumarin Derivatives from the Entomogenous Fungus Setosphaeria rostrate LGWB-10

Natural Products and Bioprospecting ◽

10.1007/s13659-020-00292-8 ◽

2021 ◽

Author(s):

Wenbin Gao ◽

Xiaoxia Wang ◽

Fengli Chen ◽

Chunqing Li ◽

Fei Cao ◽

...

Keyword(s):

Harmonia Axyridis ◽

Chemical Shifts ◽

Human Tumor ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Entomogenous Fungus ◽

Planar Structures ◽

Mcf 7 ◽

C Nmr

Abstract Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives, setosphlides A–D (1–4), and four known analogues (5–8). Their planar structures and the relative configurations were elucidated by comprehensive spectroscopic methods. The absolute configurations of isocoumarin nucleus for 1–4 were elucidated by their ECD spectra. The C-10 relative configurations for the pair of C-10 epimers (1 and 2) were established by comparing the magnitude of the computed 13C NMR chemical shifts (Δδcalcd.) with the experimental 13C NMR values (Δδexp.) for the epimers. All of the isolated compounds (1–8) were evaluated for their cytotoxicities against four human tumor cell lines MCF-7, MGC-803, HeLa, and Huh-7. Graphic Abstract

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