Disposition of the naturally occurring antimutagenic plant phenol, ellagic acid, and its synthetic derivatives, 3-O-decylellagic acid and 3, 3'-di-O-methylellagic acid in mice

1986 ◽  
Vol 7 (10) ◽  
pp. 1663-1667 ◽  
Author(s):  
Robert C. Smart ◽  
Mou-Tuan Huang ◽  
Richard L. Chang ◽  
Jane M. Sayer ◽  
Donald M. Jerina ◽  
...  
Keyword(s):  
Ellagic Acid ◽  
Naturally Occurring ◽  
Synthetic Derivatives

scholarly journals Podophyllotoxin: History, Recent Advances and Future Prospects

Biomolecules ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 603
Author(s):  
Zinnia Shah ◽  
Umar Farooq Gohar ◽  
Iffat Jamshed ◽  
Aamir Mushtaq ◽  
Hamid Mukhtar ◽  
...  
Keyword(s):  
Structure Optimization ◽  
Cytokine Storm ◽  
Chemotherapeutic Drug ◽  
Future Prospects ◽  
Naturally Occurring ◽  
Pharmacologically Active ◽  
Almost All ◽  
Pharmacologically Active Compounds ◽  
Synthetic Derivatives ◽  
Related Compounds

Podophyllotoxin, along with its various derivatives and congeners are widely recognized as broad-spectrum pharmacologically active compounds. Etoposide, for instance, is the frontline chemotherapeutic drug used against various cancers due to its superior anticancer activity. It has recently been redeveloped for the purpose of treating cytokine storm in COVID-19 patients. Podophyllotoxin and its naturally occurring congeners have low bioavailability and almost all these initially discovered compounds cause systemic toxicity and development of drug resistance. Moreover, the production of synthetic derivatives that could suffice for the clinical limitations of these naturally occurring compounds is not economically feasible. These challenges demanded continuous devotions towards improving the druggability of these drugs and continue to seek structure-optimization strategies. The discovery of renewable sources including microbial origin for podophyllotoxin is another possible approach. This review focuses on the exigency of innovation and research required in the global R&D and pharmaceutical industry for podophyllotoxin and related compounds based on recent scientific findings and market predictions.

Conformation and Absolute Configuration of Naturally Occurring Parvifoline and Several Synthetic Derivatives

1988 ◽  
Vol 51 (4) ◽  
pp. 675-689 ◽  
Author(s):  
Pedro Joseph-Nathan ◽  
María del R. Hernández-Medel ◽  
Elsa Martínez ◽  
Mirna Rojas-Gardida ◽  
Carlos M. Cerda
Keyword(s):  
Absolute Configuration ◽  
Naturally Occurring ◽  
Synthetic Derivatives

scholarly journals Rapid Loss of Factor XII- and XI-Activity in Ellagic Acid Activated Normal Plasma: Role of Plasma Inhibitors and Implications for Automated Aptt-Recording

1977 ◽  
Author(s):  
J. H. Joist ◽  
J. F. Cowan ◽  
M. Khan
Keyword(s):  
Ellagic Acid ◽  
Clinical Laboratory ◽  
Coagulation Factors ◽  
Activation Process ◽  
Factor Xii ◽  
Naturally Occurring ◽  
Normal Plasma ◽  
Factor Xiia ◽  
Loss Of Contact

Rapid prolongation of the activated partial thromboplastin time (aPTT) of normal plasma upon incubation with ellagic acid containing aPTT reagents was observed. The aPTT prolongation was not due to time dependent changes in pH in the incubation mixtures or loss of activity of the labile coagulation factors VIII and V, but occurred as a result of rapid progressive inactivation of ellagic acid activated factors XII and XI. Prolongation of the aPTT and loss of contact factor activities was not observed in plasma incubated with particulate activator reagents. This finding seemed to indicate that adsorption of factors XII and XI to larger particles during the activation process may protect these factors from inactivation by naturally occurring plasma inhibitors. Evidence is presented which supports previous observations that Ci-inhibitor, α1-antitrypsin and antithrombin III (in the presence of heparin contribute to factor XIIa- and XIa-inactivation in ellagic acid activated plasma and that plasma albumin may compete with factor XII for ellagic acid binding. The findings indicate that ellagic acid containing aPTT reagents have unfavorable properties which seriously limit their usefulness in the clinical laboratory, particularly in respect to recording of the aPTT with certain fully automated clot timers.

scholarly journals Evaluation of Antibacterial and Anti-biofilm Activities of Cinchona Alkaloid Derivatives against Staphylococcus aureus

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Malena E. Skogman ◽  
Janni Kujala ◽  
Igor Busygin ◽  
Reko Leino ◽  
Pia M. Vuorela ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Biofilm Formation ◽  
Cinchona Alkaloids ◽  
Cinchona Alkaloid ◽  
Bacterial Biofilms ◽  
Planktonic Bacteria ◽  
Naturally Occurring ◽  
Resazurin Assay ◽  
Synthetic Derivative ◽  
Synthetic Derivatives

Bacterial biofilms are resistant to most of the commonly available antibacterial chemotherapies. Thus, an enormous need exists to meet the demands of effective anti-biofilm therapy. In this study, a small library of cinchona alkaloids, including the naturally occurring compounds cinchonidine and cinchonine, as well as various synthetic derivatives and analogues was screened for antibacterial and anti-biofilm activity against the Staphylococcus aureus biofilm producing strain ATCC 25923. Two methods were used to evaluate activity against biofilms, namely crystal violet staining to measure biomass and resazurin assay to measure biofilms viability. Cinchonidine was found to be inactive, whereas a synthetic derivative, 11-triphenylsilyl-10,11-dihydrocinchonidine (11-TPSCD), was effective against planktonic bacteria as well as in preventing biofilm formation at low micromolar concentrations. Higher concentrations were required to eradicate mature biofilms.

scholarly journals Effect of Wasabi Component 6-(Methylsulfinyl)hexyl Isothiocyanate and Derivatives on Human Pancreatic Cancer Cells

2014 ◽  
Vol 2014 ◽  
pp. 1-6 ◽  
Author(s):  
Yu-Jen Chen ◽  
Yu-Chuen Huang ◽  
Tung-Hu Tsai ◽  
Hui-Fen Liao
Keyword(s):  
Pancreatic Cancer ◽  
Cancer Cells ◽  
Sonic Hedgehog ◽  
Human Pancreatic Cancer ◽  
Morphological Observation ◽  
Pancreatic Cancer Cells ◽  
Naturally Occurring ◽  
Wasabia Japonica ◽  
M Phase ◽  
Synthetic Derivatives

The naturally occurring compound 6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) was isolated fromWasabia japonica(Wasabi), a pungent spice used in Japanese food worldwide. The synthetic derivatives 6-(methylsulfenyl)hexyl isothiocyanate (I7447) and 6-(methylsulfonyl)hexyl isothiocyanate (I7557) are small molecule compounds derived from 6-MITC. This study aimed to evaluate the effect of these compounds on human pancreatic cancer cells. Human pancreatic cancer cell lines PANC-1 and BxPC-3 were used to perform an MTT assay for cell viability and Liu’s stain for morphological observation. The cell cycle was analyzed by DNA histogram. Aldehyde dehydrogenase (ALDH) activity was used as a marker for cancer stem cells (CSC). Western blotting was performed for the expression of proteins related to CSC signaling. The results showed that compounds 6-MITC and I7557, but not I7447, inhibited viability of both PANC-1 and BxPC-3 cells. Morphological observation showed mitotic arrest and apoptosis in 6-MITC- and I7557-treated cells. These two compounds induced G2/M phase arrest and hypoploid population. Percentages of ALDH-positive PANC-1 cells were markedly reduced by 6-MITC and I7557 treatment. The expression of CSC signaling molecule SOX2, but not NOTCH1, ABCG2, Sonic hedgehog, or OCT4, was inhibited by 6-MITC and I7557. In conclusion, wasabi compounds 6-MITC and I7557 may possess activity against the growth and CSC phenotypes of human pancreatic cancer cells.

scholarly journals IMPROVED HPLC RESOLUTION AND QUANTIFICATION OF ELLAGIC ACID FROM STRAWBERRY, BLACKBERRY, AND CRANBERRY

HortScience ◽  
1990 ◽  
Vol 25 (9) ◽  
pp. 1078c-1078 ◽  
Author(s):  
S. Y. Wang ◽  
J. L. Maas ◽  
E. M. Daniel ◽  
G. J. Galletta
Keyword(s):  
Ellagic Acid ◽  
Accurate Determination ◽  
Ammonium Phosphate ◽  
Solvent System ◽  
Animal Nutrition ◽  
Genetic Studies ◽  
Naturally Occurring ◽  
Chemically Induced ◽  
Improved Methods

Ellagic acid (EA) a naturally occurring polyphenol in many fruit and nut crops, is a putative inhibitor of certain chemically-induced cancers. Improved methods of extraction, detection and quantification are essential for accurate determination of EA for plant physiological and genetic studies and animal nutrition and chemopreventative studies. Column (C18) preconditioning significantly reduced column retention of EA. An ammonium phosphate/methanol solvent system was used in preference to sodium phosphate/methanol. Fruit sample determinations were 10-100 times higher than previously reported, due to the improvements in efficiency of these methods. EA levels (mg/g dry wt) were: strawberry pulp (1.55), achene (8.46), root (1.55), crown (3.32) and leaf (14.27); blackberry pulp (,2.43) and seed (3.37); and cranberry skin (1.06), pulp (0.31), seed (0.69), leaf (4.10).

scholarly journals Naturally occurring sesquiterpene lactones and their semi-synthetic derivatives modulate PGE2 levels by decreasing COX2 activity and expression

Heliyon ◽  
2019 ◽  
Vol 5 (3) ◽  
pp. e01366 ◽  
Author(s):  
Filomena Perri ◽  
Luca Frattaruolo ◽  
Ian Haworth ◽  
Matteo Brindisi ◽  
Asma El-magboub ◽  
...  
Keyword(s):  
Sesquiterpene Lactones ◽  
Naturally Occurring ◽  
Synthetic Derivatives

scholarly journals BIOLOGICAL ACTIVITIES AND NOVEL APPLICATIONS OF CHALCONES

2016 ◽  
Vol 34 (3) ◽  
pp. 607-616 ◽  
Author(s):  
C. DÍAZ-TIELAS ◽  
E. GRAÑA ◽  
M.J. REIGOSA ◽  
A.M. SÁNCHEZ-MOREIRAS
Keyword(s):  
Secondary Metabolites ◽  
Broad Spectrum ◽  
Biological Activities ◽  
Crop Protection ◽  
Plant Secondary Metabolites ◽  
Naturally Occurring ◽  
Molecular Events ◽  
Novel Applications ◽  
New Applications ◽  
Synthetic Derivatives

ABSTRACT This review provides information on the biological activities of chalcones (whether natural or synthetic derivatives) on different organisms, as well as an overview of the functions and possible new applications of these plant secondary metabolites on crop protection, as eco-friendly pesticides and weed control agents. Naturally occurring chalcones have been used in traditional medicine for many years; however, recent scientific advances have shown that these molecules have a broad range of biological activities in a variety of organisms. A review on the major sources of chalcones and the main molecular events involved in the modes of action of these natural products is achieved. Chalcones are molecules with a broad spectrum of biological activities, which are of great interest in agriculture to control weeds and unwanted pests.

scholarly journals Differential Pharmacological Activities of Oxygen Numbers on the Sulfoxide Moiety of Wasabi Compound 6-(Methylsulfinyl) Hexyl Isothiocyanate in Human Oral Cancer Cells

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2427 ◽  
Author(s):  
Min-Ju Lee ◽  
Wen-Ser Tseng ◽  
Jerry Lai ◽  
Hui-Ru Shieh ◽  
Chih-Wen Chi ◽  
...  
Keyword(s):  
Oral Cancer ◽  
Cancer Cells ◽  
Pharmacological Activities ◽  
Chemical Derivatives ◽  
Naturally Occurring ◽  
Phosphorylated Form ◽  
Wasabia Japonica ◽  
Regulated Expression ◽  
Oral Cancer Cells ◽  
Synthetic Derivatives

6-(methylsulfinyl) hexyl isothiocyanate (6-MITC) is a naturally occurring compound isolated from Wasabia japonica (wasabi). The synthetic derivatives, 6-(methylsulfenyl) hexyl isothiocyanate (I7447) and 6-(methylsulfonyl) hexyl isothiocyanate (I7557), were derived from 6-MITC with the deletion and addition of oxygen, respectively. We aimed to evaluate the effect of these synthetic compounds on human oral cancer cells, SAS and OECM-1. All three compounds (I7447, 6-MITC, and I7557) inhibited the viability of SAS and OECM-1 cells using MTT assay. Morphological observations showed various proportions of mitotic arrest and apoptosis in cells treated with these compounds. Cell cycle analysis revealed relatively abundant G2/M arrest in 6-MITC and I7557-treated cells, whereas sub-G1 accumulation was found in I7447-treated cells. In using phosphorylated histone H3 as a marker for mitosis, the addition of 6-MITC and I7557 (excluding I7447) could be shown to arrest cells during mitosis. In contrast, I7447 induced more prominent apoptosis than the 6-MITC or I7557 compounds. The down-regulated expression of the phosphorylated form of CHK1 and Cdc25c was noted in 6-MITC and I7557-treated cells. I7557 could sensitize SAS cells to death by radiation. The wasabi compound, 6-MITC, and its chemical derivatives with different numbers of oxygen may have differential pharmacological effects on human oral cancer cells.

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