DOCSLIB.ORG

The Phytochemical Piceatannol Induces the Loss of CBL and CBL-Associated Proteins

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
The Phytochemical Piceatannol Induces the Loss of CBL and CBL-Associated Proteins Published OnlineFirst March 3, 2009; DOI: 10.1158/1535-7163.MCT-08-0891 602 The phytochemical piceatannol induces the loss of CBL and CBL-associated proteins Alexander C. Klimowicz,1 Sabine A. Bisson,1 signaling pathways commonly associated with cancer. Karm Hans,2 Elizabeth M. Long,1 This work uncovers a new, piceatannol-dependent effect Henrik C. Hansen,2 and Stephen M. Robbins1 and shows a novel way in which this phenomenon can be exploited to inhibit disease-associated signaling pathways. 1Southern Alberta Cancer Research Institute, Departments of [Mol Cancer Ther 2009;8(3):602–14] Oncology and Biochemistry and Molecular Biology, and 2Department of Chemistry, The University of Calgary, Calgary, Alberta, Canada Introduction Piceatannol is a small molecule that was initially isolated as Abstract the antileukemic agent from the domesticated oilseed Piceatannol is a naturally occurring bioactive stilbene with Euphorbia lagascae (1). In mammals and mammalian cell documented antileukemic properties. It has been exten- culture, piceatannol has also been shown to have beneficial sively used as a Syk-selective protein tyrosine kinase effects as an anti-inflammatory agent (2, 3), an anti- inhibitor for the study of various signaling pathways. histamine (4, 5), and a general anticancer agent (1, 6–8). Herein, we show that the hydroxystilbene, piceatannol, Piceatannol is thought to accomplish these varied effects and related catechol ring-containing compounds are able through its inhibition of specific tyrosine and serine/ to induce the loss of the Cbl family of proteins. Normal threonine protein kinases. Piceatannol was initially shown cellular Cbl-regulatory mechanisms were not involved in to be, and is still commonly used as, a Syk-selective this process. Screening of a small library of piceatannol- protein tyrosine kinase (PTK) inhibitor (9). It can also like compounds indicated that aromaticity and a catechol inhibit other tyrosine kinases including Src, Lck, and FAK, ring were required for the induction of Cbl loss. Further albeit with lower efficiency (9–11). More recently, picea- examination of these two chemical properties showed that tannol has been shown to inhibit several serine/threonine the oxidative conversion of the catechol ring of piceatan- kinases (12, 13). The cellular effects of piceatannol are not nol into a highly reactive O-benzoquinone was the cause limited to kinase inhibition; it has been shown to induce of piceatannol-induced Cbl loss. Characterization of the apoptosis, which may be related to its inhibition of Cbl selectivity of piceatannol-induced protein loss revealed mitochondrial F0F1-ATPase activity (14, 15), and to induce that this compound was also able to induce the functional DNA damage (16–18). Piceatannol has also been shown to loss of specific Cbl-associated proteins involved in have antioxidant properties (19, 20). Despite the extensive characterization of its properties and cellular effects, piceatannol has never been associated with the loss of specific proteins. Herein, we show that piceatannol induces the loss of the Cbl family of proteins Received 9/12/08; revised 12/18/08; accepted 12/31/08; and specific Cbl-associated PTKs in a reactive oxygen published OnlineFirst 3/3/09. species (ROS)-dependent manner. Grant support: Canadian Institutes of Health Research and Alberta Cancer Board; Alberta Heritage Foundation for Medical Research, Province of The c-Cbl proto-oncogene is an adaptor protein and a Alberta, and R&D Health Research Foundation graduate fellowships (A.C. RING finger E3ubiquitin ligase; as such, it acts as both Klimowicz); and Alberta Heritage Foundation for Medical Research and Killam positive and negative regulators of many PTKs. On Scholarship at the University of Calgary graduate fellowship (S.A. Bisson). activation of receptor tyrosine kinases (RTK), c-Cbl is The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked recruited from the cytosol to the activated receptor complex advertisement in accordance with 18 U.S.C. Section 1734 solely to where it recruits signaling effector proteins and positively indicate this fact. regulates signaling by acting as an adaptor protein. Cbl Note: S.M. Robbins currently holds a Canada Research Chair in Cancer then ubiquitinates these receptors as well as many of their Biology and is a Scientist of the Alberta Heritage Foundation for Medical Research. associated signaling proteins (21), causing them to be Current address for S.A. Bisson: Howard Hughes Medical Institute, degraded by the proteasome and/or lysosome (21). Cbl Department of Microbiology and Immunology, University of California at itself is also regulated by ubiquitin-mediated proteolysis San Francisco, 513 Parnassus Avenue, HSW 1501, San Francisco, CA 94143-0552. Current address for H.C. Hansen: Resverlogix, 279 Midpark (21–24). Thus, through its E3ubiquitin ligase activity, Cbl Way Southeast, Suite 202, Calgary, Alberta, Canada T2X 1M2. also functions as a potent negative regulator of PTK Requests for reprints: Stephen M. Robbins, Southern Alberta Cancer signaling. Research Institute, Departments of Oncology and Biochemistry and We have found that piceatannol dramatically reduces Molecular Biology, The University of Calgary, 3330 Hospital Drive Northwest, Calgary, Alberta, Canada T2N-4N1. Phone: 403-220-4304; cellular Cbl protein levels independently of the protea- Fax: 403-283-8727; [email protected] some, the lysosome, and caspase activation. By screening a Copyright C 2009 American Association for Cancer Research. small library of piceatannol-like compounds, we deter- doi:10.1158/1535-7163.MCT-08-0891 mined that compound-induced Cbl protein loss was Mol Cancer Ther 2009;8(3). March 2009 Downloaded from mct.aacrjournals.org on September 28, 2021. © 2009 American Association for Cancer Research. Published OnlineFirst March 3, 2009; DOI: 10.1158/1535-7163.MCT-08-0891 Molecular Cancer Therapeutics 603 mediated directly by aromatic compounds that contain Cell Stimulations and Transfections catechol rings through their oxidative conversion into a Murine 3T3 fibroblasts ectopically expressing Cbl, mouse highly reactive O-benzoquinone. We further characterized embryonic fibroblasts, and A431 cells were plated in six- the protein selectivity of this process and established the well plates with 5 Â 105 per well in 2 mL supplemented applicability of these observations to cancer treatment. This DMEM and grown overnight before their use in experi- work characterizes a previously unrecognized piceatannol- ments. K562 and 70Z/3cells were resuspended at 8 Â dependent effect and shows a novel way in which this 105/mL in complete RPMI in a total volume of 4 mL in effect can be exploited as a therapeutic to inhibit disease- 5 mL round-bottomed polystyrene tubes the day they associated signaling pathways. were used in experiments. Six-well plates with 5 Â 105 Cbl- expressing 3T3 cells per well were grown in 2 mL supplemented DMEM overnight before transfection. Trans- Materials and Methods fection with pMT/HA-ubiquitin, a kind gift of Dr. Jane Cell Lines McGlade (Hospital for Sick Children, Toronto, Ontario, Murine 3T3 fibroblasts overexpressing wild-type c-Cbl Canada), was accomplished using Fugene 6 (Roche) accord- (wtCbl), 70ZCbl, and p95Cbl were generated and main- ing to the manufacturer’s protocol. Twenty-four hours after tained as described previously (25). The NH2-terminal transfection, cells were treated with MG132 and/or picea- HA-tagged v-Cbl allele was generously provided by tannol. The specific details regarding each experiment are Dr. Wallace Langdon and cloned into pBabepuro3as included in the figure legends. At the indicated times, cells described previously for p95Cbl (25). The Cbl deletion were lysed in NP-40 lysis buffer as described previously (25). Â mutant D1-355Cbl, a c-Cbl NH2-terminal truncation mutant Alternatively, cells were lysed in hot 2 SDS Laemmli’s that begins at codon 356, was generated by PCR using sample buffer after being washed in PBS. pBabe/wtCbl(N) and a NH2-terminal primer introducing a Immunoprecipitations and Western Blotting XhoI site in front of c-Cbl codon 356 [primer XhoCbl356(s) Immunoprecipitations and Western blots were done as 5¶-CCTCGAGACTCCCCAAGACCATATC-3¶ and primer described previously (25) using the following antibodies: Cbl6(a) 5¶-TCTCTGGAGGGACAGTCGC-3¶]. This PCR 7G10 monoclonal antibody (mAb) against c-Cbl (Upstate), product was digested with XhoI and BglII and ligated rabbit anti-Cbl polyclonal antibody (Santa Cruz Biotech- into XhoI/BglII-digested pBabe/wtCbl(N). The resultant nology), 12CA5 mAb against HA, anti-actin mAb1501 plasmid, pBabe/D1-355Cbl, was stably expressed in mu- (Chemicon), C2-10 mAb against poly(ADP-ribose) poly- rine 3T3 fibroblasts as above (25). The mouse embryonic merase (Trevigen), rabbit anti-platelet-derived growth fibroblasts were kindly provided by Dr. Hamid Band (26). factor receptor (PDGFR) polyclonal antibody (Santa Cruz The mouse embryonic fibroblasts and the A431 cells were Biotechnology), rabbit anti-Syk (Santa Cruz Biotechnology), maintained similar to the 3T3 fibroblasts in the absence of rabbit anti-p56Lyn polyclonal antibody (kind gift from Dr. any selection. The 70Z/3murine pre-B-cell line and the Anthony L. DeFranco, University of California at San K562 human erythroleukemia cell line were maintained as Francisco), rabbit anti-Abl (Cell Signaling Technology), described previously (25). Src327 mAb against
Load more

Recommended publications
  • Anti-Inflammatory Effects of Resveratrol and Related Polyphenols Contribute to Their Potential Beneficial Effects in Aging
    Tavener SK, et al., J Food Sci Nutr 2020, 6: 079 DOI: 10.24966/FSN-1076/100079 HSOA Journal of Food Science and Nutrition Review Article Abbreviations Anti-Inflammatory Effects BDNF: Brain-derived neurotrophic factor C5: Complement 5 of Resveratrol and Related CCL2: Chemokine (C-C motif) ligand 2 (aka MCP-1) Polyphenols Contribute to their CD: Cluster of differentiation COX-2: Cyclooxygenase-2 Potential Beneficial Effects in CRP: C-reactive protein CXCL10: C-X-C motif chemokine 10 Aging FOXO: Forkhead transcription factor GM-CSF: Granulocyte-macrophage colony-stimulating factor Selena K Tavener and Kiran S Panickar* HSP70: Heat shock protein 70 Science & Technology Center, Hill’s Pet Nutrition Center, Topeka, Kansas, ICAM-1: Intercellular adhesion molecule 1 USA IFN-γ: Interferon-gamma iNOS: Inducible nitric oxide synthase IL-6: Interleukin-6 Abstract JAK/STAT: Janus kinase/Signal transducer and activator of Resveratrol is a polyphenol found in grapes, blueberries, mulberry transcription and raspberry. Due to its antioxidant, anti-inflammatory, anti-microbial JNK: c-Jun N-terminal kinase and anti-proliferative properties resveratrol has been reported to LPS: Lipopolysaccharide have health benefits in aging and age-related health disorders. While MAPK: Mitogen-activated protein kinase the actions of resveratrol and related polyphenols are likely multi- MCP-1: Monocyte chemoattractant protein -1 factorial, the anti-inflammatory of polyphenols are reasonably well documented. Most studies demonstrating efficacy with resveratrol MIP-α: Macrophage inflammatory protein-1 alpha have been conducted in animal models or in vitro models. In human miR: microRNA trials some promising effects of resveratrol have been reported for NAD: Nicotinamide adenine dinucleotide several health conditions including cancer, dementia, inflammatory NFκB: Nuclear factor kappa B bowel syndrome, arthritis, ulcer and dermatological disorders.
    [Show full text]
  • Plant Phenolics: Bioavailability As a Key Determinant of Their Potential Health-Promoting Applications
    antioxidants Review Plant Phenolics: Bioavailability as a Key Determinant of Their Potential Health-Promoting Applications Patricia Cosme , Ana B. Rodríguez, Javier Espino * and María Garrido * Neuroimmunophysiology and Chrononutrition Research Group, Department of Physiology, Faculty of Science, University of Extremadura, 06006 Badajoz, Spain; [email protected] (P.C.); [email protected] (A.B.R.) * Correspondence: [email protected] (J.E.); [email protected] (M.G.); Tel.: +34-92-428-9796 (J.E. & M.G.) Received: 22 October 2020; Accepted: 7 December 2020; Published: 12 December 2020 Abstract: Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom that can be categorized as flavonoids and non-flavonoids. Interest in phenolic compounds has dramatically increased during the last decade due to their biological effects and promising therapeutic applications. In this review, we discuss the importance of phenolic compounds’ bioavailability to accomplish their physiological functions, and highlight main factors affecting such parameter throughout metabolism of phenolics, from absorption to excretion. Besides, we give an updated overview of the health benefits of phenolic compounds, which are mainly linked to both their direct (e.g., free-radical scavenging ability) and indirect (e.g., by stimulating activity of antioxidant enzymes) antioxidant properties. Such antioxidant actions reportedly help them to prevent chronic and oxidative stress-related disorders such as cancer, cardiovascular and neurodegenerative diseases, among others. Last, we comment on development of cutting-edge delivery systems intended to improve bioavailability and enhance stability of phenolic compounds in the human body. Keywords: antioxidant activity; bioavailability; flavonoids; health benefits; phenolic compounds 1. Introduction Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom with around 8000 different phenolic structures [1].
    [Show full text]
  • Bioconversion of Stilbenes in Genetically Engineered Root and Cell
    www.nature.com/scientificreports OPEN Bioconversion of stilbenes in genetically engineered root and cell cultures of tobacco Received: 04 November 2016 Diego Hidalgo1, Ascensión Martínez-Márquez2, Elisabeth Moyano3, Roque Bru-Martínez2, Accepted: 20 February 2017 Purificación Corchete4 & Javier Palazon1 Published: 27 March 2017 It is currently possible to transfer a biosynthetic pathway from a plant to another organism. This system has been exploited to transfer the metabolic richness of certain plant species to other plants or even to more simple metabolic organisms such as yeast or bacteria for the production of high added value plant compounds. Another application is to bioconvert substrates into scarcer or biologically more interesting compounds, such as piceatannol and pterostilbene. These two resveratrol-derived stilbenes, which have very promising pharmacological activities, are found in plants only in small amounts. By transferring the human cytochrome P450 hydroxylase 1B1 (HsCYP1B1) gene to tobacco hairy roots and cell cultures, we developed a system able to bioconvert exogenous t-resveratrol into piceatannol in quantities near to mg L−1. Similarly, after heterologous expression of resveratrol O-methyltransferase from Vitis vinifera (VvROMT) in tobacco hairy roots, the exogenous t-resveratrol was bioconverted into pterostilbene. We also observed that both bioconversions can take place in tobacco wild type hairy roots (pRiA4, without any transgene), showing that unspecific tobacco P450 hydroxylases and methyltransferases can perform the bioconversion of t-resveratrol to give the target compounds, albeit at a lower rate than transgenic roots. Trans-resveratrol (t-R) (3,4′ ,5-trihydroxystilbene) is a phytoalexin available from a wide range of dietary sources, including mulberries, peanuts, grapes and wine.
    [Show full text]
  • Design, Synthesis, and Evaluation of Novel Gram-Positive Antibiotics Part 2
    University of Wisconsin Milwaukee UWM Digital Commons Theses and Dissertations 12-1-2016 Part 1: Design, Synthesis, and Evaluation of Novel Gram-positive Antibiotics Part 2: Synthesis of Dihydrobenzofurans Via a New Transition Metal Catalyzed Reaction Part 3: Design, Synthesis, and Evaluation of Bz/gabaa Α6 Positive Allosteric Modulators Christopher Michael Witzigmann University of Wisconsin-Milwaukee Follow this and additional works at: https://dc.uwm.edu/etd Part of the Organic Chemistry Commons Recommended Citation Witzigmann, Christopher Michael, "Part 1: Design, Synthesis, and Evaluation of Novel Gram-positive Antibiotics Part 2: Synthesis of Dihydrobenzofurans Via a New Transition Metal Catalyzed Reaction Part 3: Design, Synthesis, and Evaluation of Bz/gabaa Α6 Positive Allosteric Modulators" (2016). Theses and Dissertations. 1429. https://dc.uwm.edu/etd/1429 This Dissertation is brought to you for free and open access by UWM Digital Commons. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of UWM Digital Commons. For more information, please contact [email protected]. PART 1: DESIGN, SYNTHESIS, AND EVALUATION OF NOVEL GRAM-POSITIVE ANTIBIOTICS PART 2: SYNTHESIS OF DIHYDROBENZOFURANS VIA A NEW TRANSITION METAL CATALYZED REACTION PART 3: DESIGN, SYNTHESIS, AND EVALUATION OF BZ/GABAA α6 POSITIVE ALLOSTERIC MODULATORS by Christopher Michael Witzigmann A Dissertation Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Chemistry at The University of Wisconsin-Milwaukee December 2016 ABSTRACT PART 1: DESIGN, SYNTHESIS, AND EVALUATION OF NOVEL GRAM-POSITIVE ANTIBIOTICS PART 2: SYNTHESIS OF DIHYDROBENZOFURANS VIA A NEW TRANSITION METAL CATALYZED REACTION PART 3: DESIGN, SYNTHESIS, AND EVALUATION OF BZ/GABAA α6 POSITIVE ALLOSTERIC MODULATORS by Christopher Michael Witzigmann The University of Wisconsin-Milwaukee, 2016 Under the Supervision of Distinguished Professor James M.
    [Show full text]
  • Piceatannol Induced Apoptosis Through Up-Regulation of Microrna
    Du et al. Biol Res (2017) 50:36 DOI 10.1186/s40659-017-0141-8 Biological Research RESEARCH ARTICLE Open Access Piceatannol induced apoptosis through up‑regulation of microRNA‑181a in melanoma cells Maotao Du1*, Zhong Zhang2 and Tao Gao2 Abstract Background: Melanoma took top position among the lethal cancers and, despite there have been some great attempts made to increase the natural life of patients with metastatic disease, long-lasting and complete remis- sions are few. Piceatannol, owns the similar function as resveratrol, has been defned as an anti-cancer agent playing important role in inhibition of proliferation, migration and metastasis in various cancer. Thus, we aim to investigate the anti-cancer efect and mechanisms of piceatannol in melanoma cells. Methods: Melanoma cell lines WM266-4 and A2058 were treated either with or without piceatannol. Cell viability and cell apoptosis were assessed by using MTT and Annexin V/PI assay, respectively. Cells were transfected with spe- cifc miRNA using Lipfectamine 2000. miRNA bingding ability to 3’-UTR region within specifc gene was assed by frefy luciferase analysis. Gene and protein expression was eveluated by qRT-PCR and western blot analysis, respectively. Results: Our study showed that piceatannol inhibited WM266-4 and A2058 cells growth and induced apoptosis. Totally, 16 diferentially expressed miRNAs were screened out including 8 up-regulated and 8 down-regulated miR- NAs. Expression level of miR-181a is signifcantly higher in piceatannol-treated cells than normal control and is lower in melanoma cancer tissues than its adjacent normal tissues. Bcl-2 is a target gene of miR-181a.
    [Show full text]
  • Literature Review Zero Alcohol Red Wine
    A 1876 LI A A U R S T T S R U A L A I A FLAVOURS, FRAGRANCES AND INGREDIENTS 6 1 7 8 7 8 1 6 A I B A L U A S R T B Essential Oils, Botanical Extracts, Cold Pressed Oils, BOTANICAL Infused Oils, Powders, Flours, Fermentations INNOVATIONS LITERATURE REVIEW HEALTH BENEFITS RED WINE ZERO ALCOHOL RED WINE RED WINE EXTRACT POWDER www.botanicalinnovations.com.au EXECUTIVE SUMMARY The term FRENCH PARADOX is used to describe the relatively low incidence of cardiovascular disease in the French population despite the high consumption of red wine. Over the past 27 years numerous clinical studies have found a linkages with the ANTIOXIDANTS in particular, the POLYPHENOLS, RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS in red wine and reduced incidences of cardiovascular disease. However, the alcohol in wine limits the benefits of wine. Studies have shown that zero alcohol red wine and red wine extract which contain the same ANTIOXIDANTS including POLYPHENOLS, RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS has the same is not more positive health benefits. The following literature review details some of the most recent positive health benefits derived from the ANTIOXIDANTS found in red wine POLYPHENOLS: RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS. The positive polyphenolic antioxidant effects of the polyphenols in red wine include: • Cardio Vascular Health Benefits • Increase antioxidants in the cardiovascular system • Assisting blood glucose control • Skin health • Bone Health • Memory • Liking blood and brain health • Benefits
    [Show full text]
  • European Patent Office
    (19) *EP003643305A1* (11) EP 3 643 305 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 29.04.2020 Bulletin 2020/18 A61K 31/196 (2006.01) A61K 31/403 (2006.01) A61K 31/405 (2006.01) A61K 31/616 (2006.01) (2006.01) (21) Application number: 18202657.5 A61P 35/00 (22) Date of filing: 25.10.2018 (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • LAEMMERMANN, Ingo GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO 1170 Wien (AT) PL PT RO RS SE SI SK SM TR • GRILLARI, Johannes Designated Extension States: 2102 Bisamberg (AT) BA ME • PILS, Vera Designated Validation States: 1160 Wien (AT) KH MA MD TN • GRUBER, Florian 1050 Wien (AT) (71) Applicants: • NARZT, Marie-Sophie • Universität für Bodenkultur Wien 1140 Wien (AT) 1180 Wien (AT) • Medizinische Universität Wien (74) Representative: Loidl, Manuela Bettina et al 1090 Wien (AT) REDL Life Science Patent Attorneys Donau-City-Straße 11 1220 Wien (AT) (54) COMPOSITIONS FOR THE ELIMINATION OF SENESCENT CELLS (57) The invention relates to a composition compris- ing senescent cells. The invention further relates to an ing one or more inhibitors capable of inhibiting at least in vitro method of identifying senescent cells in a subject two of cyclooxygenase-1 (COX-1), cyclooxygenase-2 and to a method of identifying candidate compounds for (COX-2) and lipoxygenase for use in selectively eliminat- the selective elimination of senescent cells. EP 3 643 305 A1 Printed by Jouve, 75001 PARIS (FR) 1 EP 3 643 305 A1 2 Description al.
    [Show full text]
  • Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines
    H OH metabolites OH Article Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines Andrey R. Suprun, Alexandra S. Dubrovina , Alexey P. Tyunin and Konstantin V. Kiselev * Laboratory of Biotechnology, Federal Scientific Center of the East Asia Terrestrial Biodiversity, FEB RAS, 690022 Vladivostok, Russia; [email protected] (A.R.S.); [email protected] (A.S.D.); [email protected] (A.P.T.) * Correspondence: [email protected]; Fax: +7-4232-310193 Abstract: Grapes and wines represent the most important source of edible stilbenes and other phenolic metabolites, which demonstrate a wide range of valuable biological activities. However, there is no information about the profile and content of phenolic compounds in Russian wines. We firstly analyzed phenolics (stilbenes, phenolic acids, and flavonols) in some representatives of Russian wines, including eleven red and seven white Russian wines from Fanagoria, Krasnodarsky Territory. The Russian red wines contained six stilbenes (trans-resveratrol, cis-resveratrol, trans-, cis-piceid, trans-piceatannol, d-viniferin), while the white wines contained only five stilbenes (cis- resveratrol, trans-, cis-piceid, trans-piceatannol, trans-resveratrol). More than a half of the total stilbenes in the wines (65% of all stilbenes) were presented by trans-piceid and cis-piceid, while trans-resveratrol reached 16% of all the stilbenes. The red wines also contained six phenolic acids and six flavonols, while the white wines contained six phenolic acids and only three flavonols. Myrecitin- Citation: Suprun, A.R.; Dubrovina, 3-O-glucoside, quercetin-3-O-glucoside, and myricetin were the major flavonols in the red wines, A.S.; Tyunin, A.P.; Kiselev, K.V.
    [Show full text]
  • Potential Regulators of Neutrophil Activity
    Interdiscip Toxicol. 2012; Vol. 5(2): 65–70. interdisciplinary doi: 10.2478/v10102-012-0011-8 Published online in: www.intertox.sav.sk & www.versita.com/science/medicine/it/ Copyright © 2012 SETOX & IEPT, SASc. This is an Open Access article distributed under the terms of the Creative Commons Attribu- tion License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. REVIEW ARTICLE Polyphenol derivatives – potential regulators of neutrophil activity Katarína DRÁBIKOVÁ 1, Tomáš PEREČKO 1, Radomír NOSÁĽ 1, Juraj HARMATHA 2, Jan ŠMIDRKAL 3, Viera JANČINOVÁ 1 1 Institute of Experimental Pharmacology & Toxicology, Slovak Academy of Sciences, SK-84104 Bratislava, Slovakia 2 Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo namesti 2, 166 10, Praha, Czech Republic 3 Institute of Chemical Technology Prague, Technická 5, 166 28 Praha 6-Dejvice, Czech Republic ITX050212R03 • Received: 06 May 2012 • Revised: 21 May 2012 • Accepted: 23 May 2012 ABSTRACT The study provides new information on the effect of natural polyphenols (derivatives of stilbene – resveratrol, pterostilbene, pinosyl- vin and piceatannol and derivatives of ferulic acid – curcumin, N-feruloylserotonin) on the activity of human neutrophils in influencing oxidative burst. All the polyphenols tested were found to reduce markedly the production of reactive oxygen species released by human neutrophils on extra-and intracellular levels as well as in cell free system. Moreover, pinosylvin, curcumin, N-feruloylserotonin and resveratrol decreased protein kinase C activity involved in neutrophil signalling and reactive oxygen species production.
    [Show full text]
  • Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots
    molecules Article Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots Harri Latva-Mäenpää 1,2,* , Riziwanguli Wufu 1 , Daniel Mulat 1, Tytti Sarjala 3, Pekka Saranpää 3,* and Kristiina Wähälä 1,4,* 1 Department of Chemistry, University of Helsinki, P.O. Box 55, FI-00014 Helsinki, Finland; riziwanguli.wufu@helsinki.fi (R.W.); [email protected] (D.M.) 2 Foodwest, Kärryväylä 4, FI-60100 Seinäjoki, Finland 3 Natural Resources Institute Finland, Tietotie 2, FI-02150 Espoo, Finland; tytti.sarjala@luke.fi 4 Department of Biochemistry and Developmental Biology, University of Helsinki, P.O. Box 63, FI-00014 Helsinki, Finland * Correspondence: harri.latva-maenpaa@foodwest.fi (H.L.-M.); pekka.saranpaa@luke.fi (P.S.); kristiina.wahala@helsinki.fi (K.W.); Tel.: +358-50-4487502 (H.L.-M. & P.S. & K.W.) Abstract: 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 photosen- sitive 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 Citation: Latva-Mäenpää, H.; Wufu, of biologically interesting and readily available stilbenes such as astringin and isorhapontin and R.; Mulat, D.; Sarjala, T.; Saranpää, P.; their aglucones piceatannol and isorhapontigenin, which have not been studied previously.
    [Show full text]
  • Therapeutic Role of Resveratrol and Piceatannol in Disease Prevention
    isord D ers od & lo T r B f a n o s l f a u n s r Journal of i o u n o Kukreja et al., J Blood Disorders Transf 2014, 5:9 J ISSN: 2155-9864 Blood Disorders & Transfusion DOI: 10.4172/2155-9864.1000240 Review Article OpenOpen Access Access Therapeutic Role of Resveratrol and Piceatannol in Disease Prevention Aayush Kukreja1*, Neha Wadhwa2 and Archana Tiwari1 1School of Biotechnology, Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal, India 2Department of Biotechnology, College of Professional Studies, SR Group of Institutions, Bhopal, India Abstract Resveratrol, (3,4’,5-trihydroxystilbene) has long been suspected to show a broad range of biological activities of medicinal interest such as anticancer, anti-oxidative, anti-diabetic, anti-aging and anti-inflammatory activities. Piceatannol (3,3’,4’,5-tetrahydroxystilbene) is a hydroxylated analogue of resveratrol and it confirms a lot of similar biological activities as shown by resveratrol. Both resveratrol and piceatannol are very important naturally occurring polyphenolic stilbenes, produced by plants in response to fungal infection, mechanical damage, or ultra-violet irradiation. They can be consumed on a daily basis as they show no harmful effects on human body. They play a significant role in improving human health. Compared with resveratrol, piceatannol is a more potent anticancer agent and preferable agent with other biological activities like antioxidant activity. This article reports biological activities of the two important stilbenes: resveratrol and piceatannol and their possible role in disease prevention. Keywords: Resveratrol; Piceatannol; Polyphenols; Biological naturally by 72 different plant species, especially pine trees, jackfruit, activities mulberry, blueberry, cranberry, grape vines and legumes (Figure 2).
    [Show full text]
  • The Phytochemical Potential of Gnetaceae with Peculiar Reference to Gnetum Ula and Traditional Uses of Gnetaceae Species
    Plant Archives Volume 20 No. 1, 2020 pp. 2979-2986 e-ISSN:2581-6063 (online), ISSN:0972-5210 THE PHYTOCHEMICAL POTENTIAL OF GNETACEAE WITH PECULIAR REFERENCE TO GNETUM ULA AND TRADITIONAL USES OF GNETACEAE SPECIES Mohammad Irfan Ali1, Shabina Shabir1, Lokesh Kumar Soni2, Mahabeer Prasad Dobhal1 and Sarmad Moin1* 1*School of Applied Sciences, Suresh Gyan Vihar University, Jaipur-302017 (Rajasthan) India. 2Natural Products Laboratory, Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur-302004 (Rajasthan) India. Abstract India is the home of numerous medicinally significant plants. These plants are used by people from over centuries. Among these plants, we have Gnetum ula (G. ula) which is found in India (Western Ghats). It belongs to the Gnetaceae family with one genus (Gnetum) and approximately 40 species. It is valued for its taxonomic distinctiveness and outstanding biological interest. Conventionally, it is extensively used to treat several ailments such as arthritis, jaundice, rheumatism, inflammation, etc. Initial phytochemicals analysis of Gnetum ula (G. ula) displayed the existence of saponins, tannins, resin and alkaloids, etc. Although, the plant has less economic significance. It has no official monograph and less scientific reports. These backdrops lead to lacking the attention for the plant during policy framing for conservation. Hence, the present article is an effort to compile and review the morphology, uses and importance in Gnetum ula and also explores the phytochemicals present in various species of Gnetum. Key words: Gnetum ula, Gnetaceae, Phytochemicals, Western Ghats. Introduction practitioners (Wealth of India, 1956). Leaf and Stem Gnetum ula Brongn (2n=44) constitutes a precious extracts are useful in treating both liver enlargement and group of plants where the plants have got unparalleled jaundice (Pushpangadan and Atal, 1986), while leaf paste assembly of characters which are prevalent in both which can be applied externally can be used to angiosperms as well as gymnosperms.
    [Show full text]