Dimeric 1,4-benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus Penicillium sp. L129

Two new dimeric 1,4-benzoquinone derivatives, peniquinone A (1) and peniquinone B (2), a new dibenzofuran penizofuran A (3), and a new pyrazinoquinazoline derivative quinadoline D (4), together with 13 known compounds (5–17), were isolated from a marine-derived fungus Penicillium sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound 1 exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC50 values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound 2 displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC50 values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound 2 showed weak quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with an MIC value of 20 μg/well.

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Cytotoxic Sterols from Philippine Mushrooms

Asian Journal of Chemistry ◽

10.14233/ajchem.2020.22591 ◽

2020 ◽

Vol 32 (5) ◽

pp. 1197-1202

Author(s):

Consolacion Y. Ragasa ◽

Glenn G. Oyong ◽

Maria Carmen S. Tan ◽

Mariquit M. De Los Reyes ◽

Maria Ellenita G. De Castro

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Human Cancer ◽

Dermal Fibroblast ◽

Cancer Cell Lines ◽

Cytotoxic Activities ◽

Cell Viability Assay ◽

Ic50 Values ◽

Ht 29 ◽

Mcf 7

Ergosterol peroxide (1) and ergosterol (2) were commonly isolated as the major compounds of Philippine mushrooms. Sterols 1 and 2 from the dichloromethane extract of Geastrum triplex and Termitomyces clypeatus, respectively, were evaluated for their cytotoxic activities against four human cancer cell lines, viz., breast cancer (MCF-7), colon cancer (HT-29), leukemia (THP-1), and small lung cell carcinoma (H69PR), and a human normal cell line, human dermal fibroblast-neonatal (HDFn), using the PrestoBlue® cell viability assay. Compounds 1 and 2 exhibited the strongest activities against HT-29 with IC50 values of 1.79 and 2.98 μg/mL, respectively, while Zeocin gave an IC50 of 4.89 μg/mL. These compounds also exhibited strong antiproliferative effects against MCF-7 with IC50 values of 4.13 for 1 and 4.20 μg/mL for compound 2, comparable to Zeocin with IC50 = 3.68 μg/mL. Only moderate cytotoxicity resulted when compounds 1 and 2 were tested against H69PR with IC50 values of 7.78 and 6.83 μg/mL, respectively, while Zeocin exhibited an IC50 of 9.81 μg/mL. Furthermore, compounds 1 and 2 showed no effects against THP-1 (IC50 > 100 μg/mL), while Zeocin showed an IC50 of 4.73 μg/mL. Although compounds 1 and 2 have been reported to exhibit different bioactivities in previous studies, the cancer cell lines tested and/or the polarities of the solvents for extraction varied. Therefore, comparisons of the cytotoxic activities of compounds 1 and 2 with earlier studies could not be made extensively.

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Design, Synthesis, and Biological Evaluation of Pyridineamide Derivatives Containing a 1,2,3-Triazole Fragment as Type II c-Met Inhibitors

Molecules ◽

10.3390/molecules25010010 ◽

2019 ◽

Vol 25 (1) ◽

pp. 10 ◽

Cited By ~ 1

Author(s):

Hehua Xiong ◽

Jianxin Cheng ◽

Jianqing Zhang ◽

Qian Zhang ◽

Zhen Xiao ◽

...

Keyword(s):

Antitumor Activity ◽

Cell Lines ◽

Inhibitory Activity ◽

Docking Simulation ◽

Binding Mode ◽

Biological Evaluation ◽

Design Synthesis ◽

Ic50 Values ◽

Mcf 7

A series of 4-(pyridin-4-yloxy)benzamide derivatives containing a 1,2,3-triazole fragment were designed, synthesized, and their inhibitory activity against A549, HeLa, and MCF-7 cancer cell lines was evaluated. Most compounds exhibited moderate to potent antitumor activity against the three cell lines. Among them, the promising compound B26 showed stronger inhibitory activity than Golvatinib, with IC50 values of 3.22, 4.33, and 5.82 μM against A549, HeLa, and MCF-7 cell lines, respectively. The structure–activity relationships (SARs) demonstrated that the modification of the terminal benzene ring with a single electron-withdrawing substituent (fluorine atom) and the introduction of a pyridine amide chain with a strong hydrophilic group (morpholine) to the hinge region greatly improved the antitumor activity. Meanwhile, the optimal compound B26 showed potent biological activity in some pharmacological experiments in vitro, such as cell morphology study, dose-dependent test, kinase activity assay, and cell cycle experiment. Finally, the molecular docking simulation was performed to further explore the binding mode of compound B26 with c-Met.

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Evaluating Cytotoxic Potential of the Fruit and the Leaf Extracts of Sambucus ebulus (L.) on MCF7 and AGs Cell Lines

Research in Molecular Medicine ◽

10.32598/rmm.9.1.2 ◽

2021 ◽

Vol 9 (1) ◽

pp. 11-20

Author(s):

Farzaneh Rasouli Asl ◽

◽

Ali Barzegar ◽

Mohammad Ali Ebrahimzadeh ◽

◽

...

Keyword(s):

Cell Lines ◽

Cytotoxic Activities ◽

Cancer Therapies ◽

Leaf Extracts ◽

Ags Cells ◽

Sambucus Ebulus ◽

Ic50 Values ◽

Low Cytotoxicity ◽

Inhibitory Potential ◽

Mcf 7

Background: Breast and stomach cancers are the most common malignancies in Iranian females and males, respectively. Enriching with phytochemicals that have antioxidant and cytotoxic activities, extracts from dwarf elder (Sambucus ebulus L.) holds promises to be used for alternative medication. Materials and Methods: We investigated the cytotoxic and antiproliferative activities of the leaf and the fruit ethyl-acetate (EA), as well as the methanolic (MeOH) extracts of dwarf elder upon treatment of the MCF-7 and AGS cells. Twenty-seven concentration series ranging from 10 to 2000 μg/mL were administered to the cells, and their growth inhibitory potential was assessed using MTT assay. The potential anticancer compounds of the extracts were quantified applying an improved highperformance liquid chromatography (HPLC). Results: All extracts showed positive dose-dependent cytotoxic activities on both cell lines. The EA extracts demonstrated more cytotoxicity compared to those of the MeOH ones (P<0.0001). The leaf EA extract showed IC50 values of 65 and 50 μg/mL, while those of the fruit were estimated as 58 and 50 μg/mL on the MCF-7 and AGS cells, respectively. The AGS cell line showed more susceptibility to all extracts tested compared to the MCF-7. MeOH extracts caused only a maximum of ~20% reduction in cell viability at 2000 μg/mL concentration. According to the HPLC analysis, leaf extracts contained phenolic compounds, including p- coumaric acid (0.10 mg per g powder), rutin (0.07 mg per g powder), and quercetin (0.02 mg per g powder). Conclusion: EA extract of the fruit shows the highest cytotoxicity: reducing 35.3% viability of the AGS cells with 10 μg/mL concentration. It can be considered a potential chemopreventive agent for cancer therapies. However, MeOH extracts with far low cytotoxicity or non-cytotoxic at some concentrations would be an appropriate candidate for preventing tumor growth without affecting neighboring normal cells.

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Sixteen New Prenylated Flavonoids from the Fruit of Sinopodophyllum hexandrum

Molecules ◽

10.3390/molecules24173196 ◽

2019 ◽

Vol 24 (17) ◽

pp. 3196 ◽

Cited By ~ 2

Author(s):

Yanjun Sun ◽

Haojie Chen ◽

Junmin Wang ◽

Meiling Gao ◽

Chen Zhao ◽

...

Keyword(s):

Hepg2 Cell ◽

Mtt Assay ◽

13C Nmr ◽

Spectroscopic Data ◽

Cytotoxic Activities ◽

Prenylated Flavonoids ◽

Ic50 Values ◽

Sinopodophyllum Hexandrum ◽

Hepg2 Cell Lines ◽

Mcf 7

Sixteen new prenylated flavonoids, sinoflavonoids P–Z (1–11) and sinoflavonoids NA–NE (12–16), were isolated from the fruit of Sinopodophyllum hexandrum, along with eight known analogues (17–24). Their structures were elucidated on the basis of extensive spectroscopic data (HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC). The cytotoxic activities of compounds 1–18, 20, and 22 were evaluated by MTT assay. Compound 6 showed the most potent cytotoxicity in MCF-7, and HepG2 cell lines, with IC50 values of 6.25 and 3.83 μM, respectively.

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Two New Cytotoxic Steroidal Alkaloids from Sarcococca Hookeriana

Molecules ◽

10.3390/molecules24010011 ◽

2018 ◽

Vol 24 (1) ◽

pp. 11 ◽

Cited By ~ 1

Author(s):

Shaojie Huo ◽

Jichun Wu ◽

Xicheng He ◽

Lutai Pan ◽

Jiang Du

Keyword(s):

Cell Lines ◽

Human Cancer ◽

Cytotoxic Activities ◽

Steroidal Alkaloids ◽

X Ray ◽

Human Cancer Cell Lines ◽

X Ray Crystallography ◽

Ic50 Values ◽

Mcf 7

Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). On the basis of spectroscopic methods and by comparison with literature data, their structures were determined. As well as X-ray crystallography was performed to confirm compound 4. To identify novel antitumor inhibitors, all compounds were performed a CCK-8 assay against five human cancer cell lines SW480, SMMC-7721, PC3, MCF-7 and K562 in vitro. Compound 2 exhibited moderate cytotoxic activities to all cell lines with IC50 values in the range of 5.97–19.44 μM. Compound 3 was the most effective one against SW480 and K562 cell lines with IC50 values of 5.77 and 6.29 μM, respectively.

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Ethiopian Medicinal Plants Traditionally Used for the Treatment of Cancer; Part 3: Selective Cytotoxic Activity of 22 Plants against Human Cancer Cell Lines

Molecules ◽

10.3390/molecules26123658 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3658

Author(s):

Solomon Tesfaye ◽

Hannah Braun ◽

Kaleab Asres ◽

Ephrem Engidawork ◽

Anteneh Belete ◽

...

Keyword(s):

Medicinal Plants ◽

Cell Lines ◽

Cancer Cell ◽

Mononuclear Cells ◽

Cancer Cell Lines ◽

Cytotoxic Activities ◽

Cell Lung Carcinoma ◽

Carcinoma Of The Esophagus ◽

Ic50 Values ◽

Mcf 7

Medicinal plants have been traditionally used to treat cancer in Ethiopia. However, very few studies have reported the in vitro anticancer activities of medicinal plants that are collected from different agro-ecological zones of Ethiopia. Hence, the main aim of this study was to screen the cytotoxic activities of 80% methanol extracts of 22 plants against human peripheral blood mononuclear cells (PBMCs), as well as human breast (MCF-7), lung (A427), bladder (RT-4), and cervical (SiSo) cancer cell lines. Active extracts were further screened against human large cell lung carcinoma (LCLC-103H), pancreatic cancer (DAN-G), ovarian cancer (A2780), and squamous cell carcinoma of the esophagus (KYSE-70) by using the crystal violet cell proliferation assay, while the vitality of the acute myeloid leukemia (HL-60) and histiocytic lymphoma (U-937) cell lines was monitored in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) microtiter assay. Euphorbia schimperiana, Acokanthera schimperi, Kniphofia foliosa, and Kalanchoe petitiana exhibited potent antiproliferative activity against A427, RT-4, MCF-7, and SiSo cell lines, with IC50 values ranging from 1.85 ± 0.44 to 17.8 ± 2.31µg/mL. Furthermore, these four extracts also showed potent antiproliferative activities against LCLC-103H, DAN-G, A2780, KYSE-70, HL-60, and U-937 cell lines, with IC50 values ranging from 0.086 to 27.06 ± 10.8 µg/mL. Hence, further studies focusing on bio-assay-guided isolation and structural elucidation of active cytotoxic compounds from these plants are warranted.

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Microbial Transformation of Galangin Derivatives and Cytotoxicity Evaluation of Their Metabolites

Catalysts ◽

10.3390/catal11091020 ◽

2021 ◽

Vol 11 (9) ◽

pp. 1020

Author(s):

Fubo Han ◽

Yina Xiao ◽

Ik-Soo Lee

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Microbial Transformation ◽

Cancer Cell Lines ◽

Resonance Spectroscopy ◽

Cytotoxic Activities ◽

Alpinia Officinarum ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Mcf 7

Galangin (1), 3-O-methylgalangin (2), and galangin flavanone (3), the major bioactive flavonoids isolated from Alpinia officinarum, were biotransformed into one novel and four known metabolites (4–8) by application of the fungal strains Mucor hiemalis and Absidia coerulea as biocatalysts. Their structures were characterized by extensive spectroscopic analyses including one- and two-dimensional nuclear magnetic resonance spectroscopy and mass spectrometry. Compounds 1–7 were evaluated for their cytotoxic activities against cancer cell lines using the MTT assay. The new compound 3-O-methylgalangin-7-O-β-D-glucopyranoside (6) exhibited the most potent cytotoxic activity against MCF-7, A375P, B16F10, B16F1, and A549 cancer cell lines with the IC50 values at 3.55–6.23 μM.

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One New C21 Steroidal Glycosides from the Leaves of Cynanchum hancockianum

Letters in Organic Chemistry ◽

10.2174/1570178615666181016113531 ◽

2019 ◽

Vol 16 (7) ◽

pp. 556-559

Author(s):

Shubei Yu ◽

Xixi Lin ◽

Yi Zheng ◽

Zheng Wu ◽

Wei Zheng ◽

...

Keyword(s):

Cell Lines ◽

Chemical Investigation ◽

Cytotoxic Activities ◽

First Report ◽

Steroidal Glycosides ◽

Ic50 Values ◽

Mcf 7

C21 steroids glycosides of various deoxysugars have been emerging from genus of Cynanchum. Besides classical C21 glycosides, many C21 glycosides with seco-ring aglycones attracted the extensive attention of many researchers. We conducted a systematic chemical investigation on Cynanchum hancockianum, which led to the isolation of one new seco-ring C21 steroidal glycosides. The new compound was identified as cynaascyriogenin 3-O-β-D-glucopyranosyl-(1-4)-α-L-cymaropyranosy-(1-4)- β-D-cymaropyranosyl-(1-4)-β-D-cymaropyranoside. The cytotoxic activities of the compound were evaluated using the A549 and MCF-7 cell lines, respectively. The IC50 values of the compound were 41.3 and 67.1µM, respectively. This is the first report on the isolation of seco-ring C21 steroidal glycosides from Cynanchum hancockianum.

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Two New Flavonoids from the Nuts of Areca catechu

Molecules ◽

10.3390/molecules24162862 ◽

2019 ◽

Vol 24 (16) ◽

pp. 2862 ◽

Cited By ~ 1

Author(s):

Mengfei Yuan ◽

Yunlin Ao ◽

Nan Yao ◽

Jing Xie ◽

Dongmei Zhang ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

Spectroscopic Data ◽

Human Cancer ◽

Human Cancer Cell ◽

Human Cancer Cell Lines ◽

Areca Catechu ◽

Ic50 Values ◽

Cytotoxicity Activities ◽

Hepg2 Cell Lines

Two new flavonoids, calquiquelignan M (1), calquiquelignan N (2), along with nine known compounds (3–11), were isolated from the nuts of Areca catechu (Palmae). The new structures, including absolute configurations, were established by a combination of spectroscopic data and electronic circular dichroism (ECD) calculation. The known compounds were identified by comparing their spectroscopic data with reported in the literature. The flavonoids compounds (1–8) were evaluated for their cytotoxicity activities against three human cancer cell lines. Compounds 1 and 2 exhibited a moderate cytotoxic activity against HepG2 cell lines with IC50 values of 49.8 and 53.6 μM, respectively.

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Triterpenoid Saponin and Lignan Glycosides from the Traditional Medicine Elaeagnus angustifolia Flowers and Their Cytotoxic Activities

Molecules ◽

10.3390/molecules25030462 ◽

2020 ◽

Vol 25 (3) ◽

pp. 462 ◽

Cited By ~ 1

Author(s):

Jianxin Han ◽

Xiaoyu Chen ◽

Wei Liu ◽

Hao Cui ◽

Tao Yuan

Keyword(s):

Traditional Medicine ◽

Cell Lines ◽

Spectroscopic Data ◽

Cytotoxic Activities ◽

Triterpenoid Saponin ◽

Elaeagnus Angustifolia ◽

A375 Cell ◽

Extensive Analysis ◽

Ic50 Values ◽

Lignan Glycosides

A new triterpenoid saponin, named terpengustifol A (1), and two new lignan glucosides, phengustifols A and B (2 and 3), were isolated from the flowers of Elaeagnus angustifolia. Their structures were determined by the extensive analysis of the spectroscopic data (including NMR and HRMS) and ECD calculations. Compound 1 possesses an unusual monoterpene (Z)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl unit at C-21. Compounds 2 and 3 are a pair of diastereoisomers, while their aglycones are a pair of enantiomers. Compounds 1 and 2 exhibited moderate cytotoxic activities against A375 cell lines with IC50 values at 12.1 and 15.6 μM, respectively. This is firstly reported the triterpenoid saponin and lignans isolated from the Elaeagnus angustifolia flowers.

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