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Journal articles on the topic 'Stilbene derive'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Sharp, Hazel, Jackie Hollinshead, Barbara B. Bartholomew, Julius Oben, Alison Watson, and Robert J. Nash. "Inhibitory Effects of Cissus quadrangularis L. Derived Components on Lipase, Amylase and α-Glucosidase Activity in vitro." Natural Product Communications 2, no. 8 (August 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200806.

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The stems of Cissus quadrangularis L (Vitaceae) have been consumed for centuries throughout Asia and Africa as a culinary vegetable. The aqueous extract of C. quadrangularis stems and leaves contains flavonoids and stilbenes, which inhibit lipase, amylase and α-glucosidase and, therefore, might be, at least in part, related to the claimed anti-obesity activity of the plant. The enzyme inhibition activity is outlined of a novel flavonoid (3- O-α-L-rhamnopyranosylkaempferol) (2) and stilbene (3-(4-hydroxybenzylidene)-2-(2,5-dihydroxyphenyl)-1-(4-hydroxyphenyl)indane-4,6-diol) (7), four known structurally related flavonoids, and one stilbene isolated from the extract.

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2

McAndrew, Ryan P., Noppadon Sathitsuksanoh, Michael M. Mbughuni, Richard A. Heins, Jose H. Pereira, Anthe George, Kenneth L. Sale, Brian G. Fox, Blake A. Simmons, and Paul D. Adams. "Structure and mechanism of NOV1, a resveratrol-cleaving dioxygenase." Proceedings of the National Academy of Sciences 113, no. 50 (November 30, 2016): 14324–29. http://dx.doi.org/10.1073/pnas.1608917113.

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Stilbenes are diphenyl ethene compounds produced naturally in a wide variety of plant species and some bacteria. Stilbenes are also derived from lignin during kraft pulping. Stilbene cleavage oxygenases (SCOs) cleave the central double bond of stilbenes, forming two phenolic aldehydes. Here, we report the structure of an SCO. The X-ray structure of NOV1 from Novosphingobium aromaticivorans was determined in complex with its substrate resveratrol (1.89 Å), its product vanillin (1.75 Å), and without any bound ligand (1.61 Å). The enzyme is a seven-bladed β-propeller with an iron cofactor coordinated by four histidines. In all three structures, dioxygen is observed bound to the iron in a side-on fashion. These structures, along with EPR analysis, allow us to propose a mechanism in which a ferric-superoxide reacts with substrate activated by deprotonation of a phenol group at position 4 of the substrate, which allows movement of electron density toward the central double bond and thus facilitates reaction with the ferric superoxide electrophile. Correspondingly, NOV1 cleaves a wide range of other stilbene-like compounds with a 4′-OH group, offering potential in processing some solubilized fragments of lignin into monomer aromatic compounds.

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3

More, Paresh S., and Santosh G. Singh. "Synthesis and Characterization of some Novel Stilbene Derivatives Derived from Substituted (Phenyl Acetic Acid, Benzaldehyde, Amines) Triethyl Amine and Thionyl Chloride." International Letters of Chemistry, Physics and Astronomy 43 (January 2015): 71–80. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.43.71.

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Stilbene derivatives are widely distributed in the nature and they possess various bioactivities that includes antimicrobial, antifungal, antioxidant, hepato protective, anti-HIV, cytotoxic, anti-inflammatory and antiplatelet. We have synthesized novel derivatives of stilbenes by reacting various substituted phenyl acetic acid with aldehydes in presence of acetic anhydride and triethyl amine. These derivatives were characterised by various spectral techniques and were evaluated for their antimicrobial activities.

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4

Xue, You-Qiu, Jin-Ming Di, Yun Luo, Ke-Jun Cheng, Xing Wei, and Zhi Shi. "Resveratrol Oligomers for the Prevention and Treatment of Cancers." Oxidative Medicine and Cellular Longevity 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/765832.

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Resveratrol (3,4′,5-trihydroxystilbene) is a naturally derived phytoalexin stilbene isolated from grapes and other plants, playing an important role in human health and is well known for its extensive bioactivities, such as antioxidation, anti-inflammatory, anticancer. In addition to resveratrol, scientists also pay attention to resveratrol oligomers, derivatives of resveratrol, which are characterized by the polymerization of two to eight, or even more resveratrol units, and are the largest group of oligomeric stilbenes. Resveratrol oligomers have multiple beneficial properties, of which some are superior in activity, stability, and selectivity compared with resveratrol. The complicated structures and diverse biological activities are of significant interest for drug research and development and may provide promising prospects as cancer preventive and therapeutical agents. This review presents an overview on preventive or anticancer properties of resveratrol oligomers.

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5

Cheruku, Pradeep, Jen-Huang Huang, Hung-Ju Yen, Rashi S. Iyer, Kirk D. Rector, Jennifer S. Martinez, and Hsing-Lin Wang. "Tyrosine-derived stimuli responsive, fluorescent amino acids." Chemical Science 6, no. 2 (2015): 1150–58. http://dx.doi.org/10.1039/c4sc02753a.

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6

Chalal, Malik, Dominique Delmas, Philippe Meunier, Norbert Latruffe, and Dominique Vervandier-Fasseur. "Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol." Molecules 19, no. 6 (June 11, 2014): 7850–68. http://dx.doi.org/10.3390/molecules19067850.

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7

Li, Xing-Cong, and Daneel Ferreira. "Stereoselective cyclization of stilbene derived carbocations." Tetrahedron 59, no. 9 (February 2003): 1501–7. http://dx.doi.org/10.1016/s0040-4020(03)00050-4.

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8

Baillet, Julie, Alexandra Gaubert, Dario M. Bassani, Julien Verget, Laurent Latxague, and Philippe Barthélémy. "Supramolecular gels derived from nucleoside based bolaamphiphiles as a light-sensitive soft material." Chemical Communications 56, no. 23 (2020): 3397–400. http://dx.doi.org/10.1039/d0cc00336k.

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9

Jiang, Xuliang, Jian Wu, and Yuanyuan Lu. "A facile synthesis of stilbene-linked porphyrin dimers via the Wittig reaction." Journal of Porphyrins and Phthalocyanines 10, no. 08 (August 2006): 1017–21. http://dx.doi.org/10.1142/s1088424606000363.

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A facile synthesis of free-base and metalated stilbene-linked porphyrin dimers via the Wittig reaction is reported. 5-(4-chloromethylphenyl)-10,15,20-triphenyl porphyrin was prepared by direct chloromethylation of meso-tetraphenylporphyrin as the useful precursor for both the porphyrin-derived Wittig reagent and the monoformylporphyrin. It was found that the stilbene-linked porphyrin dimers were formed with a remarkable sterochemical preference in the cis-form. Their absorption and emission spectra were measured.

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10

More, Paresh S., and Santosh G. Singh. "Synthesis and Characterization of Ester Derivatives of Stilbene Derived from Acid Derivative (of P-Chloro Phenyl Acetic Acid, Substitute Benzaldehyde, Triethyl Amine) with Methanol and Sulphuric Acid." International Letters of Chemistry, Physics and Astronomy 47 (February 2015): 49–55. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.47.49.

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Two stilbene derivatives have been synthesized in two step process. First step involved synthesis of acid derivative from p-chloro phenyl acetic acid, substituted benzaldehyde and triethyl amine, where as the second step involved synthesis of substituted stilbene derivatives (enoate or esters) through very simple route. These derivatives were characterized by various spectral techniques and were screened for their antimicrobial activities.

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11

Aguiar, M., B. Hu, F. E. Karasz, and L. Akcelrud. "Fluorescent dimer formation in stilbene-derived chromophoric polymers." Macromolecular Chemistry and Physics 199, no. 7 (July 1, 1998): 1255–61. http://dx.doi.org/10.1002/(sici)1521-3935(19980701)199:7<1255::aid-macp1255>3.0.co;2-7.

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12

Fletcher, Kristin A., Mary E. R. McHale, Karen S. Coym, and William E. Acree Jr. "Solubility of trans-stilbene in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory." Canadian Journal of Chemistry 75, no. 3 (March 1, 1997): 258–61. http://dx.doi.org/10.1139/v97-029.

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Experimental solubilities are reported at 25.0 °C for trans-stilbene dissolved in 28 different organic nonelectrolyte solvents containing methyl, ether, hydroxy, and tert-butyl functional groups. Results of these measurements are used to test the applications and limitations of expressions derived from Mobile Order theory. For the 20 solvents for which predictions could be made, computations show that Mobile Order theory does provide fairly reasonable (although by no means perfect) estimates of the saturation mole fraction solubilities. Average absolute deviation between predicted and observed values is ca. 24%. In comparison, the average absolute deviation increases significantly to 935% when ideal solution behavior is assumed. KeyWords: trans-stilbene solubilities, organic nonelectrolyte solvents, solubility predictions.

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13

Latva-Mäenpää, Harri, Riziwanguli Wufu, Daniel Mulat, Tytti Sarjala, Pekka Saranpää, and Kristiina Wähälä. "Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots." Molecules 26, no. 4 (February 16, 2021): 1036. http://dx.doi.org/10.3390/molecules26041036.

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Stilbenes or stilbenoids, major polyphenolic compounds of the bark of Norway spruce (Picea abies L. Karst), have potential future applications as drugs, preservatives and other functional ingredients due to their antioxidative, antibacterial and antifungal properties. Stilbenes are photosensitive and UV and fluorescent light induce trans to cis isomerisation via intramolecular cyclization. So far, the characterizations of possible new compounds derived from trans-stilbenes under UV light exposure have been mainly tentative based only on UV or MS spectra without utilizing more detailed structural spectroscopy techniques such as NMR. The objective of this work was to study the stability of biologically interesting and readily available stilbenes such as astringin and isorhapontin and their aglucones piceatannol and isorhapontigenin, which have not been studied previously. The effects of fluorescent and UV light and storage on the stability of trans stilbenes were assessed and the identification and characterisation of new compounds formed during our experiments were carried out by chromatographic (HPLC, GC) and spectroscopic techniques (UV, MS, NMR). The stilbenes undergo a trans to cis isomerisation under extended UV irradiation by intramolecular cyclisation (by the formation of a new C-C bond and the loss of two hydrogens) to phenanthrene structures. The characterised compounds are novel and not described previously.

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14

Feldman, Ken S. "Cyclization Pathways of a (Z)-Stilbene-Derived Bis(orthoquinone monoketal)." Journal of Organic Chemistry 62, no. 15 (July 1997): 4983–90. http://dx.doi.org/10.1021/jo9704220.

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15

Jung, J., H. Park, H. Jung, Y. Eun, J. Kim, Y. Chae, J. Yang, et al. "HMPS (2-hydroxy-4-methoxyphenylstilbene), a stilbene derivative of rhapontigenin, and cell death by mitochondrial apoptotic pathway in breast cancer cells." Journal of Clinical Oncology 27, no. 15_suppl (May 20, 2009): e22130-e22130. http://dx.doi.org/10.1200/jco.2009.27.15_suppl.e22130.

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e22130 Background: Breast cancer with resistance to clinical therapy is a significant threat to live of recurrent breast cancer patients, and chemo-resistant breast cancer is increasing rapidly. During last several decades, natural stilbenoids have been studied on anticancer effects in vitro and in vivo, and resveratrol is the most famous stilbene as a leading compound in the studies of anticancer compounds derived from plants. HMPS (2-hydroxy-4-methoxyphenylstilbene) is an analogue derived from rhapontigenin (3,5,3'-trihydroxy-4'-methoxy-trans-stilbene), which is a stilbene of herbal plant Rheum undulatum. TMS (2,3',4,5'-tetramethoxystilbene), an another stilbene analogue from rhapontigenin, was reported potent anticancer effect on tamoxifen-resistant MCF-7 cells. In this study we investigated inhibitory effect of HMPS on proliferation of breast cancer and a potential for a new therapeutic candidate. Methods: We examined cell viability of MCF-7 and MDA-MB-231 by MTT assay after exposure to various concentrations of HMPS. Apoptotic cell death induced by HMPS was investigated by florescence microscopy, cell cycle analysis and western blotting. Results: Cell viability of breast cancer cells after 24 h exposure to HMPS decreased significantly, and both ER-positive and ER-negative breast cancer cells responded to HMPS. HMPS induced nucleus fragmentation and G2/M arrest followed by sub-G1 accumulation of apoptotic cells in time- and dose-dependent manner. During the process of cell death induced by HMPS, mitochondrial membrane potential was disturbed and caspase-3 and PARP cleavage were observed. Moreover, HMPS decreased cell number of LTED MCF-7 cells(Long term estradiol deprived cell) effectively. Conclusions: Our results demonstrates that proliferation inhibitory effect of HMPS is about 50-fold more potent than those of rhapontigenin and furthermore HMPS also inhibits cell growth of LTED cells which are difficult to treat therapeutic agents. Therefore, HMPS may be a potential therapeutic candidate to treat the recurrent breast cancer by alone or combination with other conventional anticancer agents. No significant financial relationships to disclose.

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16

Banwell, Martin G., and Magne O. Sydnes. "Utilization of 1-Aryl-2,2-dibromocyclopropanes in Synthetic Approaches to Phenanthroquinolizidine and Phenanthroindolizidine Alkaloids." Australian Journal of Chemistry 57, no. 6 (2004): 537. http://dx.doi.org/10.1071/ch03292.

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The 1-aryl-2,2-dibromocyclopropane 8 was treated with silver acetate in acetic acid to give the allylic acetate 19. Exposure of the derived chloride 26 to racemic 2-piperidinemethanol (7) then afforded the allylic amine 6, which engaged in a Pd(0)-catalyzed cross-coupling reaction with arylboronate 29 to provide the cis-stilbene 25. The chloride 4 (X = Cl) derived from compound 25 failed to cyclize in the presence of base to give the desired phenanthroquinolizidine alkaloid julandine 1. This outcome resulted in a re-examination of the closing stages of a previously reported synthesis of the phenanthroindolizidine alkaloid ent-septicine (ent-3). Towards this end, chloride 26 was reacted with (S)-2-pyrrolidinemethanol (32) to give the allylic amine 33, which was cross-coupled with boronate ester 34 to afford cis-stilbene 35. Contrary to literature reports, compound 35 was converted into the corresponding chloride 37, rather than the expected mesylate, upon reaction with methanesulfonyl chloride in the presence of pyridine. Moreover, chloride 37 was not converted into ent-septicine (ent-3) on exposure to sodium hydride, thus calling into question a previously reported synthesis of this natural product.

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17

Arslaner, Ayla, and Zehra Türkoğlu. "A potential antiviral and food-derived healthy ingredient: Resveratrol." Food and Health 7, no. 1 (2021): 54–63. http://dx.doi.org/10.3153/fh21007.

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Polyphenols are the secondary metabolites of plants and has an important role in human nutrition as the leading antioxidants. According to the carbon number-based classification of polyphenols, resveratrol is a natural polyphenol in the stilbene group with antioxidant and anticarcinogenic effects. Its beneficial effects on cardiovascular diseases have also been reported. It was first identified in 1940 and has recently gained importance especially in medicine and pharmacy. Researchers have carried out various studies on resveratrol and its time-honored use in traditional eastern medicine has been reported. Resveratrol is a food ingredient that has the potential to be used in the treatment of various diseases, but also has antiviral effects. The study focuses on resveratrol’s physical and chemical properties, effects on health, antiviral effects and use in foods as a functional component.

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18

Halton, Brian, and Mark J. Cooney. "π-Extended Alkylidenecycloproparenes." Australian Journal of Chemistry 59, no. 2 (2006): 118. http://dx.doi.org/10.1071/ch05330.

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Reaction of benzene-1,4-dicarboxaldehyde with anion 6 derived from 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene 1 gives 4-(methylidene-1H-cyclopropanaphthalenyl)benzaldehyde 7 as a minor product and 1,4-bis(methylidene-1H-cyclopropanaphthalenyl)benzene 8 as the major product of the reaction. With 4-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}benzaldehyde 14, this same anion affords the stilbene-substituted π-extended (1-arylmethylidene)cyclopropanaphthalene 15 as a sparingly soluble orange-red powder.

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19

Mannila, Erkki, Antti Talvitie, and Erkki Kolehmainen. "Anti-leukaemic compounds derived from stilbenes in Picea abies bark." Phytochemistry 33, no. 4 (July 1993): 813–16. http://dx.doi.org/10.1016/0031-9422(93)85280-5.

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20

Avraamides, J. "Elimination-Reactions of Stilbene Dibromides. Debromination by Cyanide, Chloride, Iodide or 4-Nitrothiophenoxide Ions in Dimethylformamide." Australian Journal of Chemistry 39, no. 4 (1986): 677. http://dx.doi.org/10.1071/ch9860677.

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Transition state structures for debromination reactions of a series of para-substituted stilbene dibromides were evaluated from kinetic and product distribution data for the nucleophiles chloride, cyanide, iodide and 4-nitrothiophenoxide in dimethylformamide . The debrominations appear to utilize transition states in which nucleophilic attack is at bromine despite the strong carbon- nucleophilicity of some of the bases. Products are largely those derived from anti- debromination with all nucleophiles and reactivity is in the order 4-nitrothiophenoxide > cyanide > iodide > chloride.

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21

Schröder, Gudrun, and Gudrun Schröder. "Stilbene and Chalcone Synthases: Related Enzymes with Key Functions in Plant-Specific Pathways." Zeitschrift für Naturforschung C 45, no. 1-2 (February 1, 1990): 1–8. http://dx.doi.org/10.1515/znc-1990-1-202.

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Several years of extensive research using the new powerful techniques of molecular biology have enabled the direct comparison of functionally or evolutionarily related genes and their products at the nucleotide and aminoacid sequence levels. Two types of synthase with similar functions are discussed as an interesting example. Stilbene synthases, e.g. resveratrol synthase, produce the stilbene backbone as a key reaction in the biosynthesis of stilbene-type phytoalexins. Chalcone synthase is a key enzyme in the biosynthesis of flavonoids, including certain phytoalexins derived from a 6′-deoxychalcone which is synthesized by cooperation of chalcone synthase with a reductase. Resveratrol and chalcone synthases utilize the same substrates (4-coumaroyl-CoA and 3 molecules of malonyl-CoA ) and catalyze the same condensing type of enzyme reaction (resulting in sequential addition of acetate units via malonyl-CoA ), but the products differ in the newly formed ring systems (resveratrol and naringenin chalcone). A comparative analysis of cloned DNA sequences and of the reaction mechanisms indicates that the two enzymes are closely related. It seems likely that the proteins possess a common scaffold for substrate recognition and for the condensing reaction, and that the different folding of an enzyme-bound intermediate prior to closure of the new aromatic ring is responsible for the formation of the different products. The same type of condensing reaction is utilized by the 2-ketoacyl-ACP synthases of fatty-acid biosynthesis. How ever, the available data indicate that these enzymes share little overall homology with either resveratrol or chalcone synthase. One exception maybe a short aminoacid sequence which corresponds to the active center of the condensing reaction in 2-ketoacyl-ACP synthases.

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22

Fuhrer, Cyril A, Eric Grüter, Stephan Ruetz, and Robert Häner. "Cis-Stilbene Derived Furopyranones Show Potent Antiproliferative Activity by Inducing G2/M Arrest." ChemMedChem 2, no. 4 (April 16, 2007): 441–44. http://dx.doi.org/10.1002/cmdc.200600284.

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23

Wezenberg, Sander J., and Ben L. Feringa. "Photocontrol of Anion Binding Affinity to a Bis-urea Receptor Derived from Stiff-Stilbene." Organic Letters 19, no. 2 (January 11, 2017): 324–27. http://dx.doi.org/10.1021/acs.orglett.6b03423.

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24

Breau, L., W. W. Ogilvie, and T. Durst. "Preparation of optically active stilbene oxides via sulfonium salts derived from C2 symmetric thiolanes." Tetrahedron Letters 31, no. 1 (January 1990): 35–38. http://dx.doi.org/10.1016/s0040-4039(00)94327-2.

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25

Linciano, Pasquale, Barbara De Filippis, Alessandra Ammazzalorso, Pasquale Amoia, Felisa Cilurzo, Marialuigia Fantacuzzi, Letizia Giampietro, Cristina Maccallini, Charlotte Petit, and Rosa Amoroso. "Druggability profile of stilbene-derived PPAR agonists: determination of physicochemical properties and PAMPA study." MedChemComm 10, no. 11 (2019): 1892–99. http://dx.doi.org/10.1039/c9md00286c.

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PPAR agonists represent a new therapeutic opportunity for the prevention and treatment of neurodegenerative disorders, but their pharmacological success depends on favourable pharmacokinetic properties and capability to cross the BBB.

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26

Shevelev, A. B., E. P. Isakova, E. V. Trubnikova, N. La Porta, S. Martens, O. A. Medvedeva, D. V. Trubnikov, et al. "A study of antimicrobial activity of polyphenols derived from wood." Bulletin of Russian State Medical University, no. (4)2018 (September 19, 2018): 46–49. http://dx.doi.org/10.24075/brsmu.2018.043.

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Due to the spreading and increasing drug resistance of pathogens, the search for novel antibiotics is becoming ever more important. Plant-derived polyphenols are a vast and promising class of compounds with a potential to fight infectious diseases. Still, they are not routinely used in clinical practice. No reports on the in vivo studies of these compounds have been presented. The aim of our work was to compare the antimicrobial activity of resveratrol (stilbene), dihydroquercetin and dihydromyricetin (flavonols) extracted from the bark and wood of conifers against the dermatophytes Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans. Using the radial diffusion assay, we established that dihydroquercetin, resveratrol and dihydromyricetin exhibit high activity against S. aureus even at the smallest possible concentrations of 0.22, 0.15, and 0.15 mM, respectively. In contrast, the highest achievable concentrations of these compounds in the solutions (21.5, 15.5 and 15.0 mM for dihydroquercetin, resveratrol and dihydromyricetin, respectively) have no effect on the growth of P. aeruginosa and C. albicans. These findings suggest that polyphenols derived from conifers could have a potential to be used as a medicine for topical application to treat bacterial infections of the skin caused by S. aureus.

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27

Courtneidge, John L., Alwyn G. Davies, and Peter S. Gregory. "Electron spin resonance spectra of radical cations derived from stilbenes and phenanthrenes." Journal of the Chemical Society, Perkin Transactions 2, no. 10 (1987): 1527. http://dx.doi.org/10.1039/p29870001527.

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28

Okuno, Shohei, Jun Takatsuka, Madoka Nakai, Satoshi Ototake, Akio Masui, and Yasuhisa Kunimi. "Viral-enhancing activity of various stilbene-derived brighteners for a Spodoptera litura (Lepidoptera: Noctuidae) nucleopolyhedrovirus." Biological Control 26, no. 2 (February 2003): 146–52. http://dx.doi.org/10.1016/s1049-9644(02)00122-6.

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29

Suresh, Cherumuttathu H., Danaboyina Ramaiah, and Manapurathu V. George. "Rearrangement of 1,3-Dipolar Cycloadducts Derived from Bis(phenylazo)stilbene: A DFT Level Mechanistic Investigation#." Journal of Organic Chemistry 72, no. 2 (January 2007): 367–75. http://dx.doi.org/10.1021/jo061707s.

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30

Achalkumar, Ammathnadu S., B. N. Veerabhadraswamy, Uma S. Hiremath, Doddamane S. Shankar Rao, Subbarao Krishna Prasad, and Channabasaveshwar V. Yelamaggad. "Photoluminescent discotic liquid crystals derived from tris( N -salicylideneaniline) and stilbene conjugates: Structure–property correlations." Dyes and Pigments 132 (September 2016): 291–305. http://dx.doi.org/10.1016/j.dyepig.2016.05.010.

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31

Azadian, Zahra, Masoomeh Shafiei, Saadi Hosseini, Javad Kazemi, Atefeh Alipour, and Hosein Shahsavarani. "Efficient In Vitro Differentiation of Adipose Tissue-Derived Mesenchymal Stem Cells Into the Cardiomyocyte Using Plant-Derived Natural Compounds." Proceedings of the Singapore National Academy of Science 13, no. 01 (December 2019): 47–63. http://dx.doi.org/10.1142/s2591722619400064.

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Various degenerative diseases, traumatic injuries and cancers are almost hard to treat with conventional therapies, causing death or at least permanent disability. The use of multipotent adipose-derived mesenchymal stem cells (ADMSCs) for cell-based therapeutic applications has lately drawn elevated attention primarily due to their potential for differentiation into mesodermal lineages, which can finally be converted into cardiomyocytes to replace present invasive methods used to treat cardiac diseases. However, some reports hindered their clinical implementation due to concerns about efficacy scalability and reproducibility. In this research, we tested the impacts of using multiple natural small molecules and plant extract on the effectiveness of differentiating human ADMSCs into the definitive mesoderm lineage and cardiac progenitors. First, mesenchymal stem cells separated from human adult fat tissue, are propagated and characterized using flow cytometry and appropriate markers for this purpose. Second, passage cells are transferred to 24 well plates and treated with various plant-derived small molecules — primarily one of the most preserved intracellular signals, WNT/[Formula: see text]-catenin stimulators including resveratrol, stilbene, and multiple plant extracts — and assessed their impacts on differentiation into the definitive mesoderm and cardiac lineages. Obtained results revealed that our suggested strategy to differentiation is more viable and safer than present approaches. Taken together, data presented here showed that in vitro differentiation using plant-derived small molecules could be a potential way to improve the effectiveness of their final differentiation into definitive cardiomyocytes for in vivo applications.

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32

Singh, A. K., G. B. Afink, C. J. Venglarik, R. P. Wang, and R. J. Bridges. "Colonic Cl channel blockade by three classes of compounds." American Journal of Physiology-Cell Physiology 261, no. 1 (July 1, 1991): C51—C63. http://dx.doi.org/10.1152/ajpcell.1991.261.1.c51.

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We compared the potency and inhibitory actions of three different classes of organic acids on a Cl channel derived from colonic enterocyte plasma membrane vesicles. Chloride channels were incorporated into planar lipid bilayer membranes to examine the effects of the anthranilic acids, diphenylamine 2-carboxylic acid (DPC) and 5-nitro-2-(3-phenylpropylamino)benzoic acid (NPPB), the indanyl alkanoic acids, 2-[(2-cyclopentyl-6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-1H-inden -5-yl)oxy] acetic acid (IAA-94) and its stereoenantiomer IAA-95, and the disulfonic stilbene, 4,4'-dinitro-stilbene-2,2'-disulfonic acid (DNDS). Except for DNDS, each of the blockers was equipotent from both the outer membrane and the cytoplasmic side of the channel protein. The potency order from the outmembrane side was DNDS greater than IAA-94 = IAA-95 greater than NPPB much greater than DPC. In contrast, the potency order from the cytoplasmic side was IAA-94 = IAA-95 greater than NPPB greater than DNDS much greater than DPC. DPC and NPPB caused a concentration-dependent decrease in the single-channel conductance (fast block). DNDS, IAA-94, and IAA-95 caused a flickery-type block and a concentration-dependent decrease in open-channel probability. Kinetic analysis revealed that blockade could be explained by a linear closed-opened-blocked kinetic scheme. Similarities in the electrostatic potential maps of these open-channel blockers suggest they may bind to a single shared binding site within the channel protein.

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Mahmood, Yazan Abdulmuttaleb, and Bahaa T. Chiad. "Synthesis and spectroscopic study of highly fluorescent carbon dots derived from orange juice with Stilbene 420 dye." Iraqi Journal of Physics (IJP) 18, no. 44 (February 27, 2020): 62–68. http://dx.doi.org/10.30723/ijp.v18i44.510.

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Highly-fluorescent Carbon Quantum Dots (CQDs) are synthesized in simple step by hydrothermal carbonization method of natural precursor such as orange juice as a carbon source. Hydrothermal method for synthesized CQDs requires simple and inexpensive equipment and raw materials, thus this method are now common synthesis method. The prepared CQDs have ultrafine size up to few nanometers and several features such as high solubility in water, low toxicity, high biocompatibility, photo-bleaching resistant, Chemical inertness and ease of functionalization which qualifies it for use in many applications such as bio-imaging, photo-labeling and photo-catalysis. This research demonstrates the method of prepared highly fluorescence CQDs and also briefly introduce the most commonly used techniques for characterizing CQDs and the results obtained and studying their optical properties by adding Stilbene 420 dye in a method that changes the input power of used laser and prove that the output power intensity depends on the input power.

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Faustino, Célia, Ana P. Francisco, Vera M. S. Isca, and Noélia Duarte. "Cytotoxic Stilbenes and Derivatives as Promising Antimitotic Leads for Cancer Therapy." Current Pharmaceutical Design 24, no. 36 (February 15, 2019): 4270–311. http://dx.doi.org/10.2174/1381612825666190111123959.

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The growing incidence of cancer, the toxic side-effects associated with conventional chemotherapeutic agents and the development of multidrug resistance (MDR) drive the search for novel and more effective drugs with multi-target activity and selectivity towards cancer cells. Stilbenes are a group of naturally occurring phenolic compounds of plant origin derived from the phenylpropanoid pathway that may exist as cis- or trans-isomers. Although the trans-isomer is the more common and stable configuration, resveratrol being a representative compound, cis-stilbenes are potent cytotoxic agents that bind to and inhibit tubulin polymerization, destabilizing microtubules. This review summarizes the chemistry and biological evaluation of cytotoxic stilbenes and their synthetic derivatives as promising antimitotic leads for cancer therapy, focusing on the most potent compounds, the combretastatins. Combretastatins isolated from the South African bushwillow Combretum caffrum are among the most potent antimitotic and vascular disrupting agents (VDAs) of natural origin. Preclinical studies have demonstrated their potent antitumor effects in a wide variety of tumors, both in vitro and in vivo, being currently under evaluation in phase 2 and phase 3 clinical trials for several types of solid tumors. Topics covered herein include synthetic medicinal chemistry, modes of action, structure-activity relationships (SAR), preclinical and clinical studies as VDAs in cancer therapy, either as single agents or in combination with cytotoxic anticancer drugs, antiangiogenic agents, or radiation therapy, and development of appropriate formulations based on nanocarriers (e.g., liposomes, nanoemulsions, polymeric, lipid and ceramic nanoparticles, carbon nanotubes) for improved bioavailability and targeted delivery of combretastatins to the tumor vasculature.

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Zakova, Tereza, Johana Rondevaldova, Andrea Bernardos, Premysl Landa, and Ladislav Kokoska. "The relationship between structure and in vitro antistaphylococcal effect of plant-derived stilbenes." Acta Microbiologica et Immunologica Hungarica 65, no. 4 (December 2018): 467–76. http://dx.doi.org/10.1556/030.65.2018.040.

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Tomaskova, Zuzana, Jana Gaburjakova, Anna Brezova, and Marta Gaburjakova. "Inhibition of anion channels derived from mitochondrial membranes of the rat heart by stilbene disulfonate—DIDS." Journal of Bioenergetics and Biomembranes 39, no. 4 (September 25, 2007): 301–11. http://dx.doi.org/10.1007/s10863-007-9090-1.

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Baker, Jon, and Krzysztof Wolinski. "Kinetically stable high-energy isomers of C14H12 and C12H10N2 derived from cis-stilbene and cis-azobenzene." Journal of Molecular Modeling 17, no. 6 (September 14, 2010): 1335–42. http://dx.doi.org/10.1007/s00894-010-0835-0.

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Bonello, Mariella, Uroš Gašić, Živoslav Tešić, and Everaldo Attard. "Production of Stilbenes in Callus Cultures of the Maltese Indigenous Grapevine Variety, Ġellewża." Molecules 24, no. 11 (June 4, 2019): 2112. http://dx.doi.org/10.3390/molecules24112112.

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The production of secondary metabolites in tissue culture has been considered as an alternative to the cultivation and harvesting of crops intended for this purpose. The present study was aimed at the growth of callus and production of polyphenolic compound of callus derived from a Maltese indigenous grapevine variety, Ġellewża. Callus was inoculated onto plant growth regulators-enriched Murashige Skoog media (MSm) to determine whether polyphenols are produced in vitro as well as to determine the best combination of plant growth regulators needed for the production of these metabolites. From results obtained, it was observed that the best callus production was obtained by auxin-enriched MSm. In fact, indole acetic acid and indole acetic acid /6-benzyl aminopurine enhanced biomass accumulation (3.04 g and 3.39 g) as opposed to the others (<1.97 g). On the other hand, parameters showing the presence of flavonoids (tonality, 3.80), particularly anthocyanins (24.09 mg/kg) and total polyphenols (1.42 mg/g), were optimum in the presence of cytokinins, particularly 6-benzyl aminopurine. Analysis for single polyphenols revealed a high amount a particular stilbene: polydatin (glucoside of resveratrol). Resveratrol and other typical polyphenols, found in mature berries, were also found in significant quantities, while the other polyphenolic compounds were found in minimal quantities. This is the first study to describe the production and composition of polyphenols in Ġellewża callus cultures. From the results obtained, it can be seen that this grape tissue is an excellent alternative for the production of polyphenols from the stilbene group, which can be upscaled and exploited commercially.

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Park, In Sil, Youngjin Han, HyunA Jo, Ki Won Lee, and Yong Sang Song. "Piceatannol Is Superior to Resveratrol at Suppressing Adipogenesis in Human Visceral Adipose-Derived Stem Cells." Plants 10, no. 2 (February 14, 2021): 366. http://dx.doi.org/10.3390/plants10020366.

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Resveratrol (3,4′,5-trans-trihydroxystilbene) and piceatannol (3,3′,4′,5-trans-tetraphydroxystilbene) are major stilbene compounds that are predominantly present in various natural foods, such as berries and fruits. Both phytochemical compounds are consumed as dietary supplements to prevent various metabolic diseases and for their anti-aging properties. Adipose-derived stem cells from human visceral adipose tissue (vASCs) are a useful in vitro model for evaluating their adipogenic effect. Treatment with resveratrol and piceatannol significantly inhibited lipid accumulation in vASCs. Their effective concentrations were 5, 10, and 20 μM for inhibiting adipogenesis of vASCs. Interestingly, despite the similar chemical structures of the two compounds, piceatannol showed a higher anti-adipogenic effect at 20 μM than resveratrol in vASCs. Moreover, the inhibitory capacity of lipid droplet generation was higher for piceatannol at 20 μM than that of resveratrol. Piceatannol significantly attenuated the expression level of adipogenic markers (e.g., CCAAT/enhanced binding protein α (C/EBPα), peroxisome proliferator-activated receptor γ (PPARγ), and adipocyte fatty acid binding protein (aP2)) compared to resveratrol at the mRNA and protein levels. These results suggest that piceatannol is a superior anti-adipogenic compound compared to resveratrol in the vASC model of visceral obesity.

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Liu, Wei-Guo, Jun-Yi Zhao, Hao Zhang, Xin-Yong Liu, and Xiu-Li Guo. "MSTMP, a Stilbene Derivative, Protects SH-SY5Y Cells Against Oxidative Stress." Canadian Journal of Neurological Sciences / Journal Canadien des Sciences Neurologiques 41, no. 3 (May 2014): 382–88. http://dx.doi.org/10.1017/s0317167100017340.

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Objective:The protective effects of a novel stilbene derivative, (E)-2-(3,4,5-trimethoxystyryl)-3,5,6-trimethylpyrazine (MSTMP), on hydrogen peroxide (H2O2)-induced human derived neuroblastoma cell (SH-SY5Y) damage and its molecular mechanisms were investigated.Methods:SH-SY5Y cells were exposed to 200 μmol·L−1 H2O2 for 12 h. The effect of MSTMP on cell viability and apoptosis was assessed by 3-(4,5-dimethyl- thiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay and flow cytometry method. The activities of lactate dehydrogenase (LDH), superoxide dismutase (SOD) and nitric oxide synthetase (NOS) and the content of malondialdehyde (MDA), reduced glutathione (GSH) and nitric oxide (NO) in cells were determined by commercial kits. The expressions of pro-apoptotic factor caspase-3, caspase-9 and inducible NOS (iNOS) were detected by Western blotting. Intracellular formation of reactive oxygen species (ROS) was assessed using 6-carboxy-2',7'-dichlorofluorescin diacetate (DCFH-DA) fluorescent probe.Results:MSTMP increased the SH-SY5Y cell viability by inhibition of cell apoptosis induced by H2O2. These effects were accompanied by an increase of SOD activity, GSH level, and a decrease of MDA content. Moreover, MSTMP showed stronger effects on inhibition of LDH leakage, apoptotic cells, intracellular ROS level and the expression of caspase-3 and caspase-9 than TMP. Furthermore, MSTMP induced a decrease of NO level and the activity of iNOS, tNOS in a time-dependent manner.Conclusions:MSTMP prevents H2O2-induced cell injury through anti-oxidation and anti-apoptosis via ROS-NO pathway.

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DANTSKER, D. "PHOTOINDUCED NONLINEAR EFFECTS IN ORGANIC PHOTOCHROMICS." Journal of Nonlinear Optical Physics & Materials 05, no. 04 (October 1996): 775–88. http://dx.doi.org/10.1142/s0218863596000556.

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An analytic expression describing two-wavelength light propagation through an organic photoreversible photochromic Azo and Stilbene-like molecular media characterized by a strong nonoverlapping absorption by the two chromophore isomers has been derived. An analysis of the transmission coefficients for the Trans and Cis modulation modes has shown linear dependence on the pump intensity accompanied by self modulation slope dependence. In addition, the wavelength dependence of the modulation strength and the resulting inverse relationship of the pump intensity as a function of the absorption cross-section has been presented. Large constrast ratios have been obtained for rather low pump and read-out intensities of the order of a hundred microwatts per centimeter square and less. Such optimal working conditions provide a very attractive characteristic for an OASLM based on photoreversible photochromic organic molecular systems.

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Rezaei-Seresht, Esmail, Aboulfazl Salimi, and Behnam Mahdavi. "Synthesis, antioxidant and antibacterial activity of azo dye-stilbene hybrid compounds." Pigment & Resin Technology 48, no. 1 (January 7, 2019): 84–88. http://dx.doi.org/10.1108/prt-01-2018-0005.

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Purpose The purpose of this paper is synthesis and evaluation of antioxidant and antibacterial activities of a series of new azo dyes derived from 4-aminostilbene. Design/methodology/approach First, the starting material 4-aminostilbene was prepared via two successive Wittig and reduction reactions from 4-nitrobenzyl bromide. The obtained 4-aminostilbene was then reacted with some phenols under the normal azo coupling reaction conditions to give five new azo products. Antioxidant activity of the azo compounds was determined by radical scavenging assay using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Also, the antimicrobial activity of the compounds against one gram-positive and eight gram-negative strains was evaluated based on the inhibition zone using disc diffusion assay. Findings The structures of the azo dyes were identified and characterized by fourier-transform Infrared, 1H nuclear magnetic resonance (NMR) and ultraviolet-visible (UV-V) is spectroscopic methods. All the compounds showed higher antioxidant activity than ascorbic acid (Asc) and butylated hydroxytoluene (BHT) as positive controls. Moreover, the compounds showed lower antibacterial activity than the standard antibiotic vancomycin. Research limitations/implications Excellent antioxidant activity, along with antibacterial activity against Streptococcus pneumoniae and Pseudomonas aeruginosa, was observed for the two synthesized azo dyes. Originality/value Five novel azo dyes based on 4-aminostilbene were synthesized. The dyes have a highly p-extended conjugated structure comprising the phenolic and stilbenic segments, and they indicated good antioxidant activity, so that the two dyes (2c and 2d) even showed much more scavenging activity compared to BHT which is used as an antioxidant agent in food industries. These compounds with highest antioxidant activity also inhibited the growth of S. pneumoniae and P. aeruginosa.

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Guyot, Erwan, Xavier Coumoul, Jean-François Chassé, Farid Khallouki, Jean François Savouret, Marc Poirot, and Robert Barouki. "Identification of a new stilbene-derived inducer of paraoxonase 1 and ligand of the Aryl hydrocarbon Receptor." Biochemical Pharmacology 83, no. 5 (March 2012): 627–32. http://dx.doi.org/10.1016/j.bcp.2011.12.013.

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Sák, Martin, Ivana Dokupilová, Šarlota Kaňuková, Michaela Mrkvová, Daniel Mihálik, Pavol Hauptvogel, and Ján Kraic. "Biotic and Abiotic Elicitors of Stilbenes Production in Vitis vinifera L. Cell Culture." Plants 10, no. 3 (March 5, 2021): 490. http://dx.doi.org/10.3390/plants10030490.

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The in vitro cell cultures derived from the grapevine (Vitis vinifera L.) have been used for the production of stilbenes treated with different biotic and abiotic elicitors. The red-grape cultivar Váh has been elicited by natural cellulose from Trichoderma viride, the cell wall homogenate from Fusarium oxysporum and synthetic jasmonates. The sodium-orthovanadate, known as an inhibitor of hypersensitive necrotic response in treated plant cells able to enhance production and release of secondary metabolite into the cultivation medium, was used as an abiotic elicitor. Growth of cells and the content of phenolic compounds trans-resveratrol, trans-piceid, δ-viniferin, and ɛ-viniferin, were analyzed in grapevine cells treated by individual elicitors. The highest accumulation of analyzed individual stilbenes, except of trans-piceid has been observed after treatment with the cell wall homogenate from F. oxysporum. Maximum production of trans-resveratrol, δ- and ɛ-viniferins was triggered by treatment with cellulase from T. viride. The accumulation of trans-piceid in cell cultures elicited by this cellulase revealed exactly the opposite effect, with almost three times higher production of trans-resveratrol than that of trans-piceid. This study suggested that both used fungal elicitors can enhance production more effectively than commonly used jasmonates.

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Velic, Denis, Alexandre Demeyer, Thibaut Peterlini, Houda Benhelli-Mokrani, Monique Mathé-Allainmat, Jean-Yves Masson, and Fabrice Fleury. "Molecular Determinant of DIDS Analogs Targeting RAD51 Activity." Molecules 26, no. 18 (September 8, 2021): 5460. http://dx.doi.org/10.3390/molecules26185460.

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RAD51 is the central protein in DNA repair by homologous recombination (HR), involved in several steps of this process. It is shown that overexpression of the RAD51 protein is correlated with increased survival of cancer cells to cancer treatments. For the past decade, RAD51 overexpression-mediated resistance has justified the development of targeted inhibitors. One of the first molecules described to inhibit RAD51 was the 4,4′-diisothiocyanato-stilbene-2,2′-disulfonic acid (DIDS) molecule. This small molecule is effective in inhibiting different functions of RAD51, however its mode of action and the chemical functions involved in this inhibition have not been identified. In this work, we used several commercial molecules derived from DIDS to characterize the structural determinants involved in modulating the activity of RAD51. By combining biochemical and biophysical approaches, we have shown that DIDS and two analogs were able to inhibit the binding of RAD51 to ssDNA and prevent the formation of D-loop by RAD51. Both isothiocyanate substituents of DIDS appear to be essential in the inhibition of RAD51. These results open the way to the synthesis of new molecules derived from DIDS that should be greater modulators of RAD51 and more efficient for HR inhibition.

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Adhikari, Kamal, I.-Wen Lo, Chun-Liang Chen, Yung-Lin Wang, Kuan-Hung Lin, Saeid Malek Zadeh, Rajesh Rattinam, Yi-Shan Li, Chang-Jer Wu, and Tsung-Lin Li. "Chemoenzymatic Synthesis and Biological Evaluation for Bioactive Molecules Derived from Bacterial Benzoyl Coenzyme A Ligase and Plant Type III Polyketide Synthase." Biomolecules 10, no. 5 (May 9, 2020): 738. http://dx.doi.org/10.3390/biom10050738.

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Plant type III polyketide synthases produce diverse bioactive molecules with a great medicinal significance to human diseases. Here, we demonstrated versatility of a stilbene synthase (STS) from Pinus Sylvestris, which can accept various non-physiological substrates to form unnatural polyketide products. Three enzymes (4-coumarate CoA ligase, malonyl-CoA synthetase and engineered benzoate CoA ligase) along with synthetic chemistry was practiced to synthesize starter and extender substrates for STS. Of these, the crystal structures of benzoate CoA ligase (BadA) from Rhodopseudomonas palustris in an apo form or in complex with a 2-chloro-1,3-thiazole-5-carboxyl-AMP or 2-methylthiazole-5-carboxyl-AMP intermediate were determined at resolutions of 1.57 Å, 1.7 Å, and 2.13 Å, respectively, which reinforces its capacity in production of unusual CoA starters. STS exhibits broad substrate promiscuity effectively affording structurally diverse polyketide products. Seven novel products showed desired cytotoxicity against a panel of cancer cell lines (A549, HCT116, Cal27). With the treatment of two selected compounds, the cancer cells underwent cell apoptosis in a dose-dependent manner. The precursor-directed biosynthesis alongside structure-guided enzyme engineering greatly expands the pharmaceutical repertoire of lead compounds with promising/enhanced biological activities.

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Ardid-Ruiz, Andrea, Maria Ibars, Pedro Mena, Daniele Del Rio, Begoña Muguerza, Cinta Bladé, Lluís Arola, Gerard Aragonès, and Manuel Suárez. "Potential Involvement of Peripheral Leptin/STAT3 Signaling in the Effects of Resveratrol and Its Metabolites on Reducing Body Fat Accumulation." Nutrients 10, no. 11 (November 14, 2018): 1757. http://dx.doi.org/10.3390/nu10111757.

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Bioactive compounds such as polyphenols have increased in importance in recent years, and among them, resveratrol (3,5,4′-trihydroxy-trans-stilbene) has generated great interest as an anti-obesity agent. Recent investigations have highlighted the importance of leptin signaling in lipid metabolism in peripheral organs. The aims of this study were (1) to investigate whether resveratrol can reduce fat accumulation in peripheral tissues by increasing their leptin sensitivity and (2) to identify which resveratrol-derived circulating metabolites are potentially involved in these metabolic effects. Serum leptin levels and the leptin signaling pathway were assessed in diet-induced obese rats. Moreover, serum metabolites of resveratrol were studied by ultra-high performance liquid chromatography–mass spectrometry (UHPLC-MSn). The daily consumption of 200 mg/kg of resveratrol, but not doses of 50 and 100 mg/kg, reduced body weight and fat accumulation in obese rats and restored leptin sensitivity in the periphery. These effects were due to increases in sirtuin 1 activity in the liver, leptin receptors in muscle and protection against endoplasmic reticulum (ER)-stress in adipose tissue. In general, the resveratrol metabolites associated with these beneficial effects were derived from both phase II and microbiota metabolism, although only those derived from microbiota increased proportionally with the administered dose of resveratrol. In conclusion, resveratrol reversed leptin resistance caused by diet-induced obesity in peripheral organs using tissue-specific mechanisms.

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Huang, Chibao, Anxiang Ren, Chenghao Feng, and Nianfa Yang. "Two-photon fluorescent probe for silver ion derived from twin-cyano-stilbene with large two-photon absorption cross section." Sensors and Actuators B: Chemical 151, no. 1 (November 2010): 236–42. http://dx.doi.org/10.1016/j.snb.2010.09.013.

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Chao, Y. C., and S. S. Yang. "Disazo direct dyes derived from 4,4′-diamino derivatives of benzanilide, diphenylamine-2-sulfonic acid and stilbene-2,2′-disulfonic acid." Dyes and Pigments 29, no. 2 (January 1995): 131–38. http://dx.doi.org/10.1016/0143-7208(95)00038-h.

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Pettit, George R., Collin R. Anderson, Eric J. Gapud, M. Katherine Jung, John C. Knight, Ernest Hamel, and Robin K. Pettit. "Antineoplastic Agents. 515. Synthesis of Human Cancer Cell Growth Inhibitors Derived from 3,4-Methylenedioxy-5,4‘-dimethoxy-3‘-amino-Z-stilbene." Journal of Natural Products 68, no. 8 (August 2005): 1191–97. http://dx.doi.org/10.1021/np058033l.

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