Anticancer Activities of Chemical Constituents from Leaves and Twigs of <i>Mitrephora winitii</i>

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.

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Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x21993345 ◽

2021 ◽

Vol 16 (2) ◽

pp. 1934578X2199334

Author(s):

Do Thi Trang ◽

Bui Huu Tai ◽

Dan Thuy Hang ◽

Pham Hai Yen ◽

Phan Thi Thanh Huong ◽

...

Keyword(s):

Cytotoxic Activity ◽

Spectral Data ◽

Absolute Configuration ◽

Marine Sponge ◽

Chemical Constituents ◽

2D Nmr ◽

Extensive Analysis ◽

First Time ◽

Tddft Method ◽

Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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Synthesis, Antibacterial and Anticancer Activities Evaluation of New 4-Thiazolidinone-Indolin-2-One Analogs

Biointerface Research in Applied Chemistry ◽

10.33263/briac126.80948104 ◽

2021 ◽

Vol 12 (6) ◽

pp. 8094-8104

Keyword(s):

Cancer Cells ◽

Cancer Cell ◽

A549 Cells ◽

Cancer Cell Line ◽

Mitochondrial Pathway ◽

Knoevenagel Reaction ◽

Anticancer Activities ◽

Dapi Staining ◽

Mcf 7

A series of novel thiazolidinone-isatin hybrids have been synthesized through the Knoevenagel reaction of isatin derivatives with synthesized thiazolidinone scaffolds and then evaluated for their in vitro antibacterial effects on Escherichia coli (E.coli) and Staphylococcus aureus (S.aureus). Cytotoxic effects of the compounds on non-small-cell lung cancer cells (A549 cells), breast epithelial cancer cell line (MCF-7), and prostate cancer cells (PC3 cells) were investigated. Among compounds tested for antibacterial activity, S. aureus was susceptible to compound 7d. The most potent compounds against A549, MCF-7, and PC3 tumor cells were found to be 7g. DAPI staining of all cancer cell lines treated with compound 7g, associated with cell death. We finally confirmed that apoptosis occurred in A549 cells by up-regulated Bax expression and down-regulated Bcl-2 expression from the mitochondrial pathway of apoptosis by using the quantitative reverse transcription-polymerase chain reaction (qRT-PCR) method. Our findings suggested that compound 7g may be a good target in designing cancer therapy strategies.

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CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

Vietnam Journal of Science and Technology ◽

10.15625/2525-2518/57/2/13019 ◽

2019 ◽

Vol 57 (2) ◽

pp. 162

Author(s):

Quan Minh Pham ◽

Hoai Van Thi Tran ◽

Lam Tien Do ◽

Phuong Lan Doan ◽

Inh Thi Cam ◽

...

Keyword(s):

Mental Disorders ◽

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Chemical Constituents ◽

2D Nmr ◽

Spectroscopic Methods ◽

Tree Roots ◽

Chemical Structures ◽

Phytochemical Investigation ◽

First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

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N-Containing Metabolites from the Marine Sponge Agelas clathrodes

Natural Product Communications ◽

10.1177/1934578x1300801213 ◽

2013 ◽

Vol 8 (12) ◽

pp. 1934578X1300801

Author(s):

Fan Yang ◽

Rui-Hua Ji ◽

Jiang Li ◽

Jian-Hong Gan ◽

Hou-Wen Lin

Keyword(s):

South China Sea ◽

Cell Line ◽

Cancer Cell ◽

South China ◽

Marine Sponge ◽

Cancer Cell Line ◽

Spectrometric Analysis ◽

Chemical Structures ◽

Naturally Occurring ◽

First Time

A new bisuracil analogue, 3,3-bis(uracil-1-yl)-propan-1-aminium (1), together with four known N-containing metabolites (2–5), were isolated from the South China Sea sponge Agelas clathrodes. Their chemical structures were established on the basis of spectroscopic and spectrometric analysis and comparison with known compounds. Compound 1 is an unusual naturally occurring bisuracil analogue, and compound 2 was isolated from a natural source for the first time. Compounds 2 and 4 exhibit moderate cytotoxicity against cancer cell line SGC7901.

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Anti-Cancer Effect of Angelica Sinensis on Women’s Reproductive Cancer

Functional Foods in Health and Disease ◽

10.31989/ffhd.v2i6.86 ◽

2012 ◽

Vol 2 (6) ◽

pp. 242 ◽

Cited By ~ 2

Author(s):

Hong-Hong Zhu ◽

Guo-Hui Huang ◽

Patricia L. Tate ◽

Lyndon L. Larcom

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Uv Light ◽

Cancer Cell Line ◽

Cancer Cell Lines ◽

Dose Effect ◽

Angelica Sinensis ◽

Reproductive Disorders ◽

Anti Cancer ◽

Mcf 7

Objective: Danggui, the root of Angelica Sinensis, has traditionally been used for the treatment of women’s reproductive disorders in China for thousands of years. This study was to determine whether Danggui have potential anti-cancer effect on women’s cancer and its potential mechanism. Methods: Danggui was extracted by ethanol. The Cell Titer 96® Aqueous Non-Radioactive Cell Proliferation Assay was used to compare the effects of Danggui on human breast (MCF-7 and 7368) and cervical (CaSki and SiHa) cancer cells with its effects on normal fibroblasts (HTB-125). A revised Ames test was used to test for antimutagenicity. The standard strains of Salmonella typhimarium (TA) 100 and 102 were used in the test. Methyl methane sulfonate (MMS) and UV light were used as positive mutagen controls and ethanol and double distilled water (DDW) as controls. The SAS statistical software was used to analyze the data. Results: Danggui was found to be much more toxic to all cancer cell lines tested than to normal fibroblasts. There was a significant negative dose-effect relationship between Danggui and cancer cell viability. Average viability of MCF-7 was 69.5%, 18.4%, 5.7%, 5.7%, and 5.0% of control for Danggui doses 0.07, 0.14, 0.21, 0.32, and 0.64 ug/ul, respectively, with a Ptrend < 0.0001. Half maximal inhibitory dose (ID50) of Danggui for cancer cell lines MCF-7, CaSki, SiHa and CRL-7368 was 0.10, 0.09, 0.10 and 0.07 ug/ul, respectively. For the normal fibroblasts, ID50 was 0.58 ug/ul. At a dose of 0.32 ug/ul, Danggui killed over 90% of the cells in each cancer cell line, but at the same dose, only 12.3 % of the normal HTB-125 cells were killed. Revertants per plate of TA 100 decreased with the introduction of increasing doses of Danggui extracts with a Ptrend < 0.0001 when UV light was used as a mutagen. There was no difference in revertants per plate between ethanol and DDW control groups. Conclusions: Danggui could be used as a safe and effective adjuvant therapy to prevent and treat breast and cervical cancers. Anti-cancer effects may be due to its anti-mutagenicity. Danggui should be investigated as a potential adjuvant anti-cancer therapy for women’s cancer treatment and prevention of recurrence. Key words: Angelica Sinensis, Danggui, cancer, women’s reproductive disorders

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Cytotoxic and Pro-apoptotic Activities of Diterpenoids from Zhumeria Majdae

Letters in Organic Chemistry ◽

10.2174/1570178617999201111203150 ◽

2020 ◽

Vol 17 ◽

Author(s):

Abolfazl Shakeri ◽

Samira Navabi Nejad ◽

Javad Asili ◽

Milena Masullo ◽

Mansoor Saeidi ◽

...

Keyword(s):

Cell Lines ◽

Cytotoxic Effect ◽

Therapeutic Agent ◽

2D Nmr ◽

Etoac Extract ◽

Chemical Structures ◽

Ic50 Value ◽

Cytotoxic Compounds ◽

First Time ◽

Mcf 7

Abstract:: Since the ethylacetate (EtOAc) extract of the roots of Zhumeria majdae had the potent cytotoxic effect (IC50 < 50 μg/ml) on three cancer cell lines; MCF-7, PC3 and MDA-MB-231, therefore the purpous of this study is to isolation of the responcible cytotoxic compounds from the plant. Isolation of the extract led to the identification of four diterpenoids named as lanugon Q (1), 12,16-dideoxy aegyptinone B (2), 12-deoxy-salvipisone (3) and manool (4). The chemical structures have been determined on the basis of 1D and 2D NMR experiments. Compound 1 is reported for the first time in the plants of Zhumeria genus. The results of cytotoxic and apoptotic evaluation revealed that compound 2 had the strong cytotoxic effect with the IC50 value of 15.90 μg/ml against MCF-7 cell lines. Sub-G1 peak in flow cytometry histogram of cells treated with EtOAc axtract and compound 2 showed the induction of apoptosis. Changes in the Bax/Bcl-2 ratio and cleavage of PARP were observed. It is to be noted that owing to strong cytotoxic effect, Z. majdae extract could be represented as therapeutic agent against cancer.

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Cytotoxic and Apoptotic Effects of Novel Pyrrolo[2,3-d]Pyrimidine Derivatives Containing Urea Moieties on Cancer Cell Lines

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520618666180605082026 ◽

2019 ◽

Vol 18 (9) ◽

pp. 1303-1312 ◽

Cited By ~ 3

Author(s):

Zühal Kilic-Kurt ◽

Filiz Bakar-Ates ◽

Bahriye Karakas ◽

Özgür Kütük

Keyword(s):

Cell Cycle ◽

Cytotoxic Activity ◽

Cell Line ◽

Cancer Cell ◽

A549 Cells ◽

Cancer Cell Line ◽

Anticancer Activities ◽

Cycle Arrest ◽

Apoptotic Protein ◽

Mcf 7

Background: Pyrrolo[2,3-d]pyrimidines have been recently reported to have anticancer activities through inhibition of different targets such as, Epidermal Growth Factor Receptor (EGFR) tyrosine kinase, Janus Kinase (JAK), mitotic checkpoint protein kinase (Mps1), carbonic anhydrase, MDM-2. On the other hand, aryl urea moieties which are found in some tyrosine kinase inhibitors such as Sorafenib and Linifanib have aroused recent attention as responsible for anticancer activities. The aims of this paper are to synthesize pyrrolo[ 2,3-d]pyrimidine derivatives containing urea moiety and evaluate their anti-cancer activity against human lung cancer cell line (A549), prostate cancer cell line (PC3), human colon cancer cell line (SW480) and human breast cancer cell line (MCF-7). Methods: A series of new pyrrolo[2,3-d]pyrimidines containing urea moieties have been synthesized as Scheme 1. In vitro cytotoxicity of target compounds were evaluated against, SW480, PC3, A549 and MCF-7 human cancer cell lines using a MTT assay. In order to evaluate the mechanism of cytotoxic activity of compounds 9e, 10a and 10b, having the best cytotoxic activity, Annexin V binding assay, cell cycle analysis and western blot analysis were performed. Results: Among the target compounds, 10a (IC50 = 0.19 µM) was found to be the most potent derivative against PC3 cells. Compound 10b and 9e showed the strong cytotoxic activity against MCF-7 and A549 cells with IC50 value of 1.66 µM and 4.55 µM, respectively. Flow cytometry data suggest that the cytotoxic activity of the compounds on cancer cells might be mediated by apoptosis revealing a significant increase in the percentage of late apoptotic cells and causing a cell cycle arrest at different stages. Western blot analysis of apoptosis marker demonstrated that these compounds induce apoptosis through the intrinsic pathway. Conclusion: Compound 9e displayed the strongest cytotoxicity against A549 cancer cell line, and induced late apoptosis in A549, as confirmed by cell cycle arrest in G0/G1 phase. In addition, compound 9e reduced expression of the anti-apoptotic protein Bcl-2 and enhanced expression of the pro-apoptotic protein Bax, besides increased caspase-9 and caspase-3, as well as cleavage of PARP levels. These results suggest that compound 9e showed a cytotoxic effect in A549 cells through activation of the mitochondrial apoptotic pathway. Further studies will be undertaken in our laboratory to improve cytotoxic activity of compound 9e and to identify the biological targets of 9e which are responsible for anticancer activity.

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Niclosamide loaded biodegradable chitosan nanocargoes: an in vitro study for potential application in cancer therapy

Royal Society Open Science ◽

10.1098/rsos.170611 ◽

2017 ◽

Vol 4 (11) ◽

pp. 170611 ◽

Cited By ~ 13

Author(s):

Saba Naqvi ◽

Shanid Mohiyuddin ◽

P. Gopinath

Keyword(s):

Breast Cancer ◽

Cancer Therapy ◽

Cell Line ◽

Cancer Cell ◽

Breast Cancer Cell ◽

Chitosan Nanoparticles ◽

Cancer Cell Line ◽

Human Lung Cancer ◽

Anti Cancer ◽

Mcf 7

Chitosan nanoparticles can advance the pharmacological and therapeutic properties of chemotherapeutic agents by controlling release rates and targeted delivery process, which eliminates the limitations of conventional anti-cancer therapies and they are also safe as well as cost-effective. The aim of present study is to explore the anti-tumour effect of niclosamide in lung and breast cancer cell lines using biocompatible and biodegradable carrier where nanoparticles loaded with hydrophobic drug (niclosamide) were synthesized, characterized and applied as a stable anti-cancer agent. Niclosamide loaded chitosan nanoparticles (Nic-Chi Np's) of size approximately 100–120 nm in diameter containing hydrophobic anti-cancer drug, i.e. niclosamide, were prepared. Physico-chemical characterization confirms that the prepared nanoparticles are spherical, monodispersed and stable in aqueous systems. The therapeutic efficacy of Nic-Chi Np's was evaluated against breast cancer cell line (MCF-7) and human lung cancer cell line (A549). MTT assay reveals the cell viability of the prepared Nic-Chi Np's against A549 and MCF-7 cells and obtained an IC 50 value of 8.75 µM and 7.5 µM, respectively. Acridine orange/ethidium bromide dual staining results verified the loss of the majority of the cells by apoptosis. Flow cytometer analysis quantified the generation of intracellular reactive oxygen species (ROS) and signified that exposure to a higher concentration (2 × IC 50 ) of Nic-Chi Np's resulted in elevated ROS generation. Notably, Nic-Chi Np treatment showed more apoptosis and cell death in MCF-7 as compared to A549. Further, the remarkable induction of apoptosis by Nic-Chi Np's was confirmed by semi-quantitative reverse transcription polymerase chain reaction, scanning electron microscopy and cell-cycle analysis. Thus, Nic-Chi Np's may have a great potential even at low concentration for anti-cancer therapy and may replace or substitute more toxic anti-mitotic drugs in the near future.

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Novel Efficient Bioprocessing of Marine Chitins into Active Anticancer Prodigiosin

Marine Drugs ◽

10.3390/md18010015 ◽

2019 ◽

Vol 18 (1) ◽

pp. 15 ◽

Cited By ~ 9

Author(s):

Van Bon Nguyen ◽

Shan-Ping Chen ◽

Thi Hanh Nguyen ◽

Minh Trung Nguyen ◽

Thi Thanh Thao Tran ◽

...

Keyword(s):

Serratia Marcescens ◽

Bioactive Compound ◽

Potential Candidate ◽

Hep G2 ◽

Anticancer Activities ◽

Anti Cancer ◽

Initial Ph ◽

Ic50 Values ◽

First Time ◽

Mcf 7

Marine chitins (MC) have been utilized for the production of vast array of bioactive products, including chitooligomers, chitinase, chitosanase, antioxidants, anti-NO, and antidiabetic compounds. The aim of this study is the bioprocessing of MC into a potent anticancer compound, prodigiosin (PG), via microbial fermentation. This bioactive compound was produced by Serratia marcescens TKU011 with the highest yield of 4.62 mg/mL at the optimal conditions of liquid medium with initial pH of 5.65–6.15 containing 1% α-chitin, 0.6% casein, 0.05% K2HPO4, and 0.1% CaSO4. Fermentation was kept at 25 °C for 2 d. Notably, α-chitin was newly investigated as the major potential material for PG production via fermentation; the salt CaSO4 was also found to play the key role in the enhancement of PG yield of Serratia marcescens fermentation for the first time. PG was qualified and identified based on specific UV, MALDI-TOF MS analysis. In the biological activity tests, purified PG demonstrated potent anticancer activities against A549, Hep G2, MCF-7, and WiDr with the IC50 values of 0.06, 0.04, 0.04, and 0.2 µg/mL, respectively. Mytomycin C, a commercial anti-cancer compound was also tested for comparison purpose, showing weaker activity with the IC50 values of 0.11, 0.1, 0.14, and 0.15 µg/mL, respectively. As such, purified PG displayed higher 2.75-fold, 1.67-fold, and 3.25-fold efficacy than Mytomycin C against MCF-7, A549, and Hep G2, respectively. The results suggest that marine chitins are valuable sources for production of prodigiosin, a potential candidate for cancer drugs.

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New Antiproliferative Cembrane Diterpenes from the Red Sea Sarcophyton Species

Marine Drugs ◽

10.3390/md17070411 ◽

2019 ◽

Vol 17 (7) ◽

pp. 411 ◽

Cited By ~ 9

Author(s):

Hossam M. Hassan ◽

Mostafa E. Rateb ◽

Marwa H. Hassan ◽

Ahmed M. Sayed ◽

Samah Shabana ◽

...

Keyword(s):

Red Sea ◽

Antiproliferative Activity ◽

High Resolution Mass Spectrometry ◽

Cancer Cell Line ◽

2D Nmr ◽

Future Design ◽

Chemical Structures ◽

New Compounds ◽

Mcf 7

The combination of liquid chromatography coupled to high resolution mass spectrometry (LC-HRESMS)-based dereplication and antiproliferative activity-guided fractionation was applied on the Red Sea-derived soft coral Sarcophyton sp. This approach facilitated the isolation of five new cembrane-type diterpenoids (1–5), along with two known analogs (6 and 7), as well as the identification of 19 further, known compounds. The chemical structures of the new compounds were elucidated while using comprehensive spectroscopic analyses, including one-dimensional (1D) and two-dimensional (2D) NMR and HRMS. All of the isolated cembranoids (1–7) showed moderate in vitro antiproliferative activity against a human breast cancer cell line (MCF-7), with IC50 ranging from 22.39–27.12 µg/mL. This class of compounds could thus serve as scaffold for the future design of anticancer leads.

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