A Simple BF3•Et2O-mediated Cycloaddition Reaction to the Formation of Cyclic Monoterpenoid Pyrano[3,2-a]carbazole Alkaloids

2020 ◽  
Vol 17 ◽  
Author(s):  
Siow-Ping Tan ◽  
Mohd Azlan Nafiah
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Lewis Acid ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Cytotoxic Effects ◽  
New Approach ◽  
Intramolecular Cycloaddition ◽  
Ic50 Values ◽  
Carbazole Alkaloids

Abstract: A Lewis acid BF3•Et2O-mediated intramolecular cycloaddition reaction of mahanimbine (1) is described. Three cycloadducts, bicyclomahanimbine (2), cyclomahanimbine (3) and murrayazolinine (4) were obtained. The structural char-acterization of these compounds were determined by 1D and 2D NMR experiments. These compounds showed no cytotoxic activity against human MRC-5 cells (IC50 > 60 μg/mL). Compound 3 showed the highest inhibition cytotoxic effects against HeLa and HL-60 cancer cells with IC50 values of 10.0 and 28.7 μg/mL, respectively. This strategy opens a new approach for the synthesis of biologically significant cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids

scholarly journals Cytotoxic Activity of Essential Oils of Aerial Parts and Ripe Fruits of Echinophora spinosa (Apiaceae)

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Daniele Fraternale ◽  
Donata Ricci ◽  
Cinzia Calcabrini ◽  
Michele Guescini ◽  
Chiara Martinelli ◽  
...  
Keyword(s):  
Linear Regression ◽  
Essential Oils ◽  
Cytotoxic Activity ◽  
Central Italy ◽  
U937 Cells ◽  
Cytotoxic Effects ◽  
Regression Curves ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Per Se

The cytotoxic effects of the essential oils obtained from the flowering aerial parts (APO) and ripe fruits (RFO) of Echinophora spinosa L. (Apiaceae) from central Italy toward human U937 promonocytoid cells were studied; the contribution of each of the major constituents to the whole cytotoxic activity of either APO or RFO was also characterized. The major components of APO were β-phellandrene (34.7%), myristicin (16.5%), p-cymene (16.3%), δ3-carene (12.6%), α-pinene (6.7%) and α-phellandrene (6.2%); those of RFO p-cymene (50.2%), myristicin (15.3%), α-pinene (15.1%) and α-phellandrene (8.1%). Both oils tested were toxic to U937 cells, but RFO was much more cytotoxic: indeed, the IC50 values calculated from the linear regression curves of RFO and APO were 14.5 ± 0.85 and 43.4 ± 2.81 μg/mL, respectively. α-Pinene and α-phellandrene were identified as the most toxically relevant constituents: however, they did not completely account for the toxic effects of genuine APO and RFO. Interestingly, we found that p-cymene, although per se devoid of toxicity within the tested range of concentrations, was capable of significantly sensitizing U937 cells to the cytotoxic activity of α-pinene and α-phellandrene, and that specific mixtures of these three terpenes were as toxic as genuine APO and RFO.

scholarly journals Angucycline Glycosides from an Intertidal Sediments Strain Streptomyces sp. and Their Cytotoxic Activity against Hepatoma Carcinoma Cells

Marine Drugs ◽  
2018 ◽  
Vol 16 (12) ◽  
pp. 470 ◽  
Author(s):  
Aihong Peng ◽  
Xinying Qu ◽  
Fangyuan Liu ◽  
Xia Li ◽  
Erwei Li ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Fermentation Broth ◽  
Morphological Characteristics ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Intertidal Sediments ◽  
Dapi Staining ◽  
Streptomyces Sp ◽  
Ic50 Values ◽  
Induced Apoptosis

Four angucycline glycosides including three new compounds landomycin N (1), galtamycin C (2) and vineomycin D (3), and a known homologue saquayamycin B (4), along with two alkaloids 1-acetyl-β-carboline (5) and indole-3-acetic acid (6), were isolated from the fermentation broth of an intertidal sediments-derived Streptomyces sp. Their structures were established by IR, HR-ESI-MS, 1D and 2D NMR techniques. Among the isolated angucyclines, saquayamycin B (4) displayed potent cytotoxic activity against hepatoma carcinoma cells HepG-2, SMMC-7721 and plc-prf-5, with IC50 values 0.135, 0.033 and 0.244 μM respectively, superior to doxorubicin. Saquayamycin B (4) also induced apoptosis in SMMC-7721 cells as detected by its morphological characteristics in 4′,6-diamidino-2-phenylindole (DAPI) staining experiment.

scholarly journals Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea (Meliaceae)

2018 ◽  
Vol 4 (1) ◽  
pp. 7-13
Author(s):  
Ace Tatang Hidayat ◽  
Kindi Farabi ◽  
Ida Nur Farida ◽  
Kansy Haikal ◽  
Nurlelasari Nurlelasari ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Chemical Structure ◽  
2D Nmr ◽  
Leukemia Cells ◽  
Ic50 Values ◽  
First Time ◽  
Murine Leukemia

Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia cells with IC50 values of 23.96 and 8.14 mM, respectively.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7065

Antibacterial and Cytotoxic Activity of Prenylated Bicyclic Acylphloroglucinol Derivatives from Hypericum amblycalyx

2003 ◽  
Vol 58 (7-8) ◽  
pp. 527-532 ◽  
Author(s):  
Karin Winkelmann ◽  
Metin San ◽  
Zacharias Kypriotakis ◽  
Helen Skaltsa ◽  
Blazenka Bosilij ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antibacterial Activity ◽  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Structure Elucidation ◽  
Petroleum Ether Extract ◽  
2D Nmr ◽  
Ether Extract ◽  
Nmr Studies ◽  
Aerial Parts

Abstract Two new bicyclic acylphloroglucinol derivatives, hypercalyxone A (1-[5,7-dihydroxy-2-methyl- 3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-propan-1-one, 1) and B (1-[5,7-dihydroxy-2-methyl-3-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-chroman- 8-yl]-2-methyl-butan-1-one, 2), have been isolated from the petroleum ether extract of the aerial parts of Hypericum amblycalyx, together with two further compounds (1-[5,7- dihydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-propan-1-one, 3 and 1-[5,7-dihydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-chroman-8-yl]-2-methyl-butan-1-one, 4), which have been described only as semi-synthetic products. In addition, the known triterpene lup-20(29)-en-3-one was obtained. Structure elucidation was based on 1D and 2D NMR studies, as well as on data derived from mass spectrometry. The four acylphloroglucinol derivatives were evaluated for their cytotoxic and antibacterial activity. All compounds showed moderate cytotoxic activity against KB and Jurkat T cancer cells. Especially compounds 3 and 4 exhibited a strong antibacterial activity against different Gram-positive strains.

scholarly journals Preparation, COX-2 Inhibition and Anticancer Activity of Sclerotiorin Derivatives

Marine Drugs ◽  
2020 ◽  
Vol 19 (1) ◽  
pp. 12
Author(s):  
Tao Chen ◽  
Yun Huang ◽  
Junxian Hong ◽  
Xikang Wei ◽  
Fang Zeng ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Human Lung Cancer ◽  
Binding Modes ◽  
Ic50 Values ◽  
Cox 2 ◽  
Inhibitory Agents

The latest research has indicated that anti-tumor agents with COX-2 inhibitory activity may benefit their anti-tumor efficiency. A series of sclerotiorin derivatives have been synthesized and screened for their cytotoxic activity against human lung cancer cells A549, breast cancer cells MDA-MB-435 using the MTT method. Among them, compounds 3, 7, 12, 13, 15, 17 showed good cytotoxic activity with IC50 values of 6.39, 9.20, 9.76, 7.75, 9.08, and 8.18 μM, respectively. In addition, all compounds were tested in vitro the COX-2 inhibitory activity. The results disclosed compounds 7, 13, 25 and sclerotiorin showed moderate to good COX-2 inhibition with the inhibitory ratios of 58.7%, 51.1%, 66.1% and 56.1%, respectively. Notably, compound 3 displayed a comparable inhibition ratio (70.6%) to the positive control indomethacin (78.9%). Furthermore, molecular docking was used to rationalize the potential of the sclerotiorin derivatives as COX2 inhibitory agents by predicting their binding energy, binding modes and optimal orientation at the active site of the COX-2. Additionally, the structure-activity relationships (SARS) have been addressed.

scholarly journals Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3714
Author(s):  
Emmanoel V. Costa ◽  
Liviane do N. Soares ◽  
Jamal da Silva Chaar ◽  
Valdenizia R. Silva ◽  
Luciano de S. Santos ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Cancerous Cell ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Low Cytotoxicity ◽  
First Time

Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL−1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL−1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL−1 (33.70 µmol·L−1) and 18.99 µg·mL−1 (40.56 µmol·L−1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL−1, and HCT116, with an IC50 value of 17.31 µg·mL−1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.

scholarly journals Resveratrol, Curcumin and Piperine Alter Human Glyoxalase 1 in MCF-7 Breast Cancer Cells

2020 ◽  
Vol 21 (15) ◽  
pp. 5244
Author(s):  
Betina Schmidt ◽  
Christian Ferreira ◽  
Carlos Luan Alves Passos ◽  
Jerson Lima Silva ◽  
Eliane Fialho
Keyword(s):  
Breast Cancer ◽  
Cancer Cells ◽  
Bioactive Compounds ◽  
Breast Cancer Cells ◽  
Cytotoxic Effects ◽  
Glyoxalase 1 ◽  
Ic50 Values ◽  
Lactate Levels ◽  
Dietary Bioactive Compounds ◽  
Mcf 7

Breast cancer is the leading cause of cancer mortality in women worldwide. Conventional cancer treatment is costly and results in many side effects. Dietary bioactive compounds may be a potential source for breast cancer prevention and treatment. In this scenario, the aim of this study was to investigate the effects of the bioactive compounds resveratrol, curcumin and piperine (R-C-P) on MCF-7 breast cancer cells and to associate them to Glyoxalase 1 (GLO1) activity. The findings indicate that R-C-P exhibits cytotoxicity towards MCF-7 cells. R-C-P decreased mitochondrial membrane potential (ΔΨm) by 1.93-, 2.04- and 1.17-fold, respectively. Glutathione and N-acetylcysteine were able to reverse the cytotoxicity of the assessed bioactive compounds in MCF-7 cells. R-C-P reduced GLO1 activity by 1.36-, 1.92- and 1.31-fold, respectively. R-C-P in the presence of antimycin A led to 1.98-, 1.65- and 2.16-fold decreases in D-lactate levels after 2 h of treatment, respectively. Glyoxal and methylglyoxal presented cytotoxic effects on MCF-7 cells, with IC50 values of 2.8 and 2.7 mM and of 1.5 and 1.4 mM after 24 and 48 h of treatment, respectively. In conclusion, this study demonstrated that R-C-P results in cytotoxic effects in MCF-7 cells and that this outcome is associated with decreasing GLO1 activity and mitochondrial dysfunction.

scholarly journals Efek Sitotoksik Formula Jamu Daun Sirsak, Buah Takokak, dan Umbi Bidara Upas terhadap Sel Kanker Payudara MCF-7

2019 ◽  
pp. 140-149
Author(s):  
Yuli Widiyastuti ◽  
Ika Yanti Marfuatush Sholikhah ◽  
Sari Haryanti
Keyword(s):  
Medicinal Plants ◽  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Assay Method ◽  
Herbal Formula ◽  
Solanum Torvum ◽  
Medicinal Plant Extracts ◽  
Ic50 Values ◽  
Apoptosis Process ◽  
Mcf 7

Cancer is one of the leading cause of death in the world. Complicated and high cost treatments of cancer encourages people to look for alternative treatments among others using medicinal plants. Some medicinal plants that are empirically claimed to have anticancer effect are soursop (Annona muricata), takokak (Solanum torvum), and bidara upas (Merremia mammosa). However, these medicinal herbs have not been tested for cytotoxic activity against MCF-7 cancer cells. The purpose of this study was to determine the cytotoxic activity of the anticancer herbal formula consisting those three plants. The effect of each single extract and the combination formula were tested for their activity on cell viability of MCF-7 with MTT assay method. The herbal formula with the most active combination of medicinal plant extracts was further tested for its activity on the expression of Bcl-2 protein by immunocytochemistry methods. The results showed that each single extract and the combination formula gave cytotoxic effect on MCF-7 breast cancer cells. Formula A, consisted of a mixture of soursop leaves, takokak fruit, and bidas upas bulb with a ratio of 1:1:1, results in highest inhibition of the viability of MCF-7 cells with IC50 values of 48 µg/ml. The formula also enhances the apoptosis process in MCF-7 cells which is shown by decreasing the expression of antiapoptotic Bcl-2 proteins.

scholarly journals Cytotoxic Steroids From The Stembak of Chisocheton celebicus KOORD

2019 ◽  
Vol 5 (2) ◽  
pp. 143-148
Author(s):  
Dewa Gede Katja ◽  
Desi Harneti ◽  
Tri Mayanti ◽  
Nurlelasari Nurlelasari ◽  
Rani Maharani ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Leukemia Cells ◽  
Anticancer Compounds ◽  
Cytotoxic Effects ◽  
Cytotoxicity Activity ◽  
Ic50 Values ◽  
Cytotoxic Steroids ◽  
Murine Leukemia ◽  
Tof Ms

In the course of our continuing search for anticancer compounds from Chisocheton species, three steroids, stigmast-5-en-3β-ol (1), stigmast-5-en-3β-ol-3-O-β-D-glucopyranoside (2) and stigmast-5,22-dien-3β-ol-3-O-β-D-glucopyranoside (3), were obtained from the stembark of Chisocheton celebicus. The structures of compound 1-3 were identified with spectroscopic data including IR, 1D-NMR, 2D-NMR and TOF-MS, as well as by comparing with those spectral data previously. Compounds 1-3, were evaluated for their cytotoxic effects against P-388 murine leukemia cells and displayed the cytotoxicity activity with IC50 values of 12.45 ± 0.050, 52.27 ± 0.031 and 62.52 ± 0.076 µg/mL, respectively.

scholarly journals SYNTHESIS, CHARACTERIZATION AND CYTOTOXIC ACTIVITY OF Pt(II)COMPLEX OF CAMPHOR 4-METHYL THIOSEMICARBAZONE

2018 ◽  
Vol 56 (2A) ◽  
pp. 75-80
Author(s):  
Phan Thi Hong Tuyet
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cells ◽  
1H Nmr ◽  
Biomedical Application ◽  
Molecular Formula ◽  
Hep G2 ◽  
Anti Cancer ◽  
Ic50 Values ◽  
Cancer Activity

The new complex of Pt(II) with camphor 4-methyl thiosemicarbazone was synthesized and characterized by means of MS, 1H-NMR and IR spectroscopes. Results show that, the molecular formula of new Pt(II) complex is [Pt(C12H20N3S))2]. The Pt(II) complex is of four coordinate. The result of in vitro anti-cancer activity of the complex has shown that the complex of Pt(II) with camphor 4-methyl thiosemicarbazone exhibit inhibitor on Hep-G2 and RD cancer cells with IC50 values of 7.74 and 7.61 µg.mL-1. These results indicated a potential of new Pt(II)complex in biomedical application.

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