scholarly journals Duclauxin Derivatives From Fungi and Their Biological Activities

2021 ◽  
Vol 12 ◽  
Author(s):  
Hamza Shahid ◽  
Teng Cai ◽  
Yuyang Wang ◽  
Caiqing Zheng ◽  
Yuting Yang ◽  
...  
Keyword(s):  
Phylogenetic Analysis ◽  
Tumor Cell ◽  
Absolute Configuration ◽  
Mitochondrial Respiration ◽  
Biological Activities ◽  
Atp Synthesis ◽  
Medical Applications ◽  
Tumor Cell Lines ◽  
Chemical Structures ◽  
Cyclopentane Ring

Duclauxin is a heptacyclic oligophenalenone dimer consisting of an isocoumarin and a dihydroisocoumarin unit. These two tricyclic moieties are joined by a cyclopentane ring to form a unique hinge or castanets-like structure. Duclauxin is effective against numerous tumor cell lines because it prevents adenosine triphosphate (ATP) synthesis by inhibiting mitochondrial respiration. There are about 36 reported natural duclauxin analogs mainly produced by 9 Penicillium and Talaromyces species (T. duclauxii, T. aculeatus, T. stipitatus, T. bacillisporus, T. verruculosus, T. macrosporus, P. herquei, P. manginii, and Talaromyces sp.). These metabolites exhibit remarkable biological activities, including antitumor, enzyme inhibition, and antimicrobial, showing tremendous potential in agricultural and medical applications. This review highlights the chemical structures and biological activities of fungal duclauxins, together with biosynthesis, absolute configuration, and mode of action for important duclauxins. Furthermore, phylogenetic analysis and correct names of Penicillium and Talaromyces species producing duclauxins are presented in this review.

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

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.

scholarly journals Cytotoxic Effects of Plant Sap-Derived Extracellular Vesicles on Various Tumor Cell Types

2020 ◽  
Vol 11 (2) ◽  
pp. 22
Author(s):  
Kimin Kim ◽  
Hye Ju Yoo ◽  
Jik-Han Jung ◽  
Ruri Lee ◽  
Jae-Kyung Hyun ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Tumor Cells ◽  
Extracellular Vesicles ◽  
Biological Activities ◽  
Cell Types ◽  
Skin Tumor ◽  
Cytotoxic Effects ◽  
Chemical Structures ◽  
Dendropanax Morbifera ◽  
Plant Sap

Edible plants have been widely used in traditional therapeutics because of the biological activities of their natural ingredients, including anticancer, antioxidant, and anti-inflammatory properties. Plant sap contains such medicinal substances and their secondary metabolites provide unique chemical structures that contribute to their therapeutic efficacy. Plant extracts are known to contain a variety of extracellular vesicles (EVs) but the effects of such EVs on various cancers have not been investigated. Here, we extracted EVs from four plants—Dendropanax morbifera, Pinus densiflora, Thuja occidentalis, and Chamaecyparis obtusa—that are known to have cytotoxic effects. We evaluated the cytotoxic effects of these EVs by assessing their ability to selectively reduce the viability of various tumor cell types compared with normal cells and low metastatic cells. EVs from D. morbifera and P. densiflora sap showed strong cytotoxic effects on tumor cells, whereas those from T. occidentalis and C. obtusa had no significant effect on any tumor cell types. We also identified synergistic effect of EVs from D. morbifera and P. densiflora saps on breast and skin tumor cells and established optimized treatment concentrations. Our findings suggest these EVs from plant sap as new candidates for cancer treatment.

Synthesis and Biological Evaluation of New Piperazine Substituted 3, 5-Diarylisoxazolines

2019 ◽  
Vol 16 (2) ◽  
pp. 294-302 ◽  
Author(s):  
Hui Gao ◽  
Bei Liu ◽  
Ping Zhu ◽  
Li-Jun Zhang ◽  
Chun-Ping Wan ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Human Tumor ◽  
Biological Evaluation ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines

Aim and Objective: Isoxazolines are an important class of nitrogen and oxygen-containing heterocycles, which have gained much importance as the potential biological agents. In order to study structureactivity relationships of isoxazolines, this work has been conducted. Materials and Methods: A series of new piperazine substituted 3, 5-diarylisoxazoline derivatives (6-31) were designed and synthesized, and in vitro anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and anticancer effect against a panel of human tumor cell lines (Hela, A549 and SGC7901) by MTT assay were evaluated. Results: The substituents of the NH group of piperazine ring had an obvious influence on biological activities. Especially, compounds 5, 7, 8, 10, 11, 13 and 27-showed good inhibitory effect on the generation of NO compared to dexamethasone. Furthermore, derivatives 5, 6, 7, 8, 9, 13 and 26 were found to be potential selectively anticancer activity on human tumor cell lines, which displayed better cytotoxic activity to positive control 5- FU. Conclusion: Piperazine substituted 3, 5-diarylisoxazoline derivatives could be considered as new antiinflammatory and anticancer agents.

scholarly journals Preparation of Sesquiterpene Lactone Derivatives: Cytotoxic Activity and Selectivity of Action

Molecules ◽  
2019 ◽  
Vol 24 (6) ◽  
pp. 1113 ◽  
Author(s):  
María F. Beer ◽  
Augusto E. Bivona ◽  
Andrés Sánchez Alberti ◽  
Natacha Cerny ◽  
Guillermo F. Reta ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Biological Activities ◽  
Sesquiterpene Lactones ◽  
Chemotherapeutic Agents ◽  
Colon Tumor ◽  
Tumor Cell Lines ◽  
Diverse Range ◽  
Colon Tumor Cell

Cancer is one of the most important causes of death worldwide. Solid tumors represent the great majority of cancers (>90%) and the chemotherapeutic agents used for their treatment are still characterized by variable efficacy and toxicity. Sesquiterpene lactones are a group of naturally occurring compounds that have displayed a diverse range of biological activities including cytotoxic activity. A series of oxygenated and oxy-nitrogenated derivatives (4–15) from the sesquiterpene lactones cumanin (1), helenalin (2), and hymenin (3) were synthesized. The silylated derivatives of helenalin, compounds 13 and 14, were found to be the most active against tumor cell lines, with GI50 values ranging from 0.15 to 0.59 μM. The ditriazolyl cumanin derivative (11) proved to be more active and selective than cumanin in the tested breast, cervix, lung, and colon tumor cell lines. This compound was the least toxic against splenocytes (CC50 = 524.1 µM) and exhibited the greatest selectivity on tumor cell lines. This compound showed a GI50 of 2.3 µM and a SI of 227.9 on WiDr human colon tumor cell lines. Thus, compound 11 can be considered for further studies and is a candidate for the development of new antitumor agents.

Novel Resveratrol-chalcone Derivatives: Synthesis and Biological Evaluation

2019 ◽  
Vol 19 (5) ◽  
pp. 424-436 ◽  
Author(s):  
Yulu Ma ◽  
Xi Zheng ◽  
Ping Zhu ◽  
Bei Liu ◽  
Hui Gao ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Biological Activities ◽  
Human Tumor ◽  
Biological Evaluation ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Proliferative Effect ◽  
Anti Inflammatory

Introduction: Resveratrol and chalcones are lead compounds with good biological activities. </P><P> Method: In this study, a series of novel derivatives (6-38) between resveratrol and chalcone possessing piperazine moiety have been synthesized, and in vitro anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and anti-proliferative effect on a panel of human tumor cell lines (Hela, A549 and SGC7901) by MTT assay were evaluated. </P><P> Result: The results demonstrated that the substituents of the NH group of piperazine ring had an obvious influence on biological activities. Especially, compounds 13, 17, 30, 31 and 36 showed good inhibitory effect on the generation of NO compared to dexamethasone. Furthermore, analogs 20, 21, 22 and 25 were found to be the better anti-proliferative effect on 3 human tumor cell lines, which were found to be a better cytotoxic activity to positive control 5-FU. Many compounds displayed low cytotoxic effect on normal cells L02. </P><P> Conclusion: Further FACs analysis showed that compounds 20 and 25 significantly induced apoptosis in A549 cell. These derivatives were considered as the potential anti-inflammatory and anti-tumor agents.

scholarly journals Acid Rearrangment of Epoxy-germacranolides and Absolute Configuration of 1β,10α-Epoxy-salonitenolide

2010 ◽  
Vol 5 (5) ◽  
pp. 1934578X1000500
Author(s):  
Sergio Rosselli ◽  
Antonella Maria Maggio ◽  
Rosa Angela Raccuglia ◽  
Susan L. Morris-Natschke ◽  
Kenneth F. Bastow ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Tumor Cell ◽  
Natural Product ◽  
Absolute Configuration ◽  
Cancer Cell Line ◽  
Cytotoxic Activities ◽  
Tumor Cell Lines ◽  
Spectroscopic Analyses ◽  
Acid Catalyzed ◽  
Mcf 7

The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.

scholarly journals Comparative Analyses of Metabolomic Fingerprints and Cytotoxic Activities of Soft Corals from the Colombian Caribbean

Marine Drugs ◽  
2019 ◽  
Vol 17 (1) ◽  
pp. 37 ◽  
Author(s):  
Liliana Santacruz ◽  
Olivier Thomas ◽  
Carmenza Duque ◽  
Mónica Puyana ◽  
Edisson Tello
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
High Resolution Mass Spectrometry ◽  
Biological Activities ◽  
Analytical Techniques ◽  
Living Organism ◽  
Cytotoxic Agents ◽  
Cytotoxic Activities ◽  
Tumor Cell Lines ◽  
Soft Corals

Soft corals (Cnidaria, Anthozoa, Octocorallia) are a diverse group of marine invertebrates that inhabit various marine environments in tropical and subtropical areas. Several species are recognized as prolific sources of compounds with a wide array of biological activities. Recent advances in analytical techniques, supported by robust statistical analyses, have allowed the analysis and characterization of the metabolome present in a single living organism. In this study, a liquid chromatography-high resolution mass spectrometry metabolomic approach was applied to analyze the metabolite composition of 28 soft corals present in the Caribbean coast of Colombia. Multivariate data analysis was used to correlate the chemical fingerprints of soft corals with their cytotoxic activity against tumor cell lines for anticancer purpose. Some diterpenoids were identified as specific markers to discriminate between cytotoxic and non-cytotoxic crude extracts of soft corals against tumor cell lines. In the models generated from the comparative analysis of PLS-DA for tumor lines, A549 and SiHa, the diterpene 13-keto-1,11-dolabell-3(E),7(E),12(18)-triene yielded a high score in the variable importance in projection. These results highlight the potential of metabolomic approaches towards the identification of cytotoxic agents against cancer of marine origin. This workflow can be useful in several studies, mainly those that are time consuming, such as traditional bioprospecting of marine natural products.

scholarly journals Diligustilide: Enantiomeric Derivatives, Absolute Configuration and Cytotoxic Properties

2017 ◽  
Vol 56 (2) ◽  
Author(s):  
Alejandra León ◽  
Guillermo Delgado
Keyword(s):  
Tumor Cell ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Absolute Configuration ◽  
Human Tumor ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Electronic Circular Dichroism ◽  
Human Tumor Cell Lines ◽  
The Absolute

New enantiomeric amides (-)<strong>-6</strong>, (+)<strong>-7</strong>, (+)<strong>-6</strong>, and (-)<strong>-7</strong> were formed by the reaction of the natural dimeric phthalide <em>rac</em>-diligustilide (<em>rac</em><strong>-1</strong>) with (R)-(+)-α-methylbenzylamine and (S)-(-)- α-methylbenzylamine. The absolute configurations of compounds <strong>6</strong> and <strong>7</strong> were assigned by the analysis of electronic circular dichroism curves by means of the exciton chirality method. Compounds <strong>1</strong>, <strong>4</strong>, <strong>5</strong>, (-)<strong>-6</strong>, (+)<strong>-6</strong>, (+)<strong>-7</strong>, and (-)<strong>-7</strong> exhibited cytotoxic activity towards several human tumor cell lines.

Interaction of Human Tumor Cells with Human Platelets and the Coagulation System

1983 ◽  
Vol 50 (03) ◽  
pp. 726-730 ◽  
Author(s):  
Hamid Al-Mondhiry ◽  
Virginia McGarvey ◽  
Kim Leitzel
Keyword(s):  
Tumor Cell ◽  
Tumor Cells ◽  
Cell Lines ◽  
Human Tumor ◽  
Human Platelets ◽  
Factor Vii ◽  
Coagulation System ◽  
Breast Adenocarcinoma ◽  
Activate Factor ◽  
Tumor Cell Lines

SummaryThis paper reports studies on the interaction between human platelets, the plasma coagulation system, and two human tumor cell lines grown in tissue culture: Melanoma and breast adenocarcinoma. The interaction was monitored through the use of 125I- labelled fibrinogen, which measures both thrombin activity generated by cell-plasma interaction and fibrin/fibrinogen binding to platelets and tumor cells. Each tumor cell line activates both the platelets and the coagulation system simultaneously resulting in the generation of thrombin or thrombin-like activity. The melanoma cells activate the coagulation system through “the extrinsic pathway” with a tissue factor-like effect on factor VII, but the breast tumor seems to activate factor X directly. Both tumor cell lines activate platelets to “make available” a platelet- derived procoagulant material necessary for the conversion of prothrombin to thrombin. The tumor-derived procoagulant activity and the platelet aggregating potential of cells do not seem to be inter-related, and they are not specific to malignant cells.

Sign in / Sign up

Export Citation Format

Share Document