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Literature DB >> 25650836

A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

Bryan S Matsuura¹, Mitchell H Keylor, Bo Li, YuXuan Lin, Shelby Allison, Derek A Pratt, Corey R J Stephenson.

Abstract

An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical-trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity.

Entities: Chemical Disease Gene Species

Keywords: antioxidants; biomimetic synthesis; quinone methides; resveratrol; total synthesis

Mesh：

Substances：

Year: 2015 PMID： 25650836 PMCID： PMC4457443 DOI： 10.1002/anie.201409773

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

31 in total

1. C11-BODIPY(581/591), an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology.

Authors: Gregor P C Drummen; Lydia C M van Liebergen; Jos A F Op den Kamp; Jan A Post
Journal: Free Radic Biol Med Date: 2002-08-15 Impact factor: 7.376

2. Total synthesis of resveratrol-based natural products: a chemoselective solution.

Authors: Scott A Snyder; Alexandros L Zografos; Yunqing Lin
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Total synthesis of hopeahainol A and hopeanol.

Authors: K C Nicolaou; T Robert Wu; Qiang Kang; David Y-K Chen
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

Authors: Scott A Snyder; Steven P Breazzano; Audrey G Ross; Yunqing Lin; Alexandros L Zografos
Journal: J Am Chem Soc Date: 2009-02-11 Impact factor: 15.419

Review 5. Free radical lipid peroxidation: mechanisms and analysis.

Authors: Huiyong Yin; Libin Xu; Ned A Porter
Journal: Chem Rev Date: 2011-08-23 Impact factor: 60.622

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

7. Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement.

Authors: Scott A Snyder; Stephen B Thomas; Agathe C Mayer; Steven P Breazzano
Journal: Angew Chem Int Ed Engl Date: 2012-03-16 Impact factor: 15.336

8. Besting vitamin E: sidechain substitution is key to the reactivity of naphthyridinol antioxidants in lipid bilayers.

Authors: Bo Li; Jitendra R Harjani; Nicholas S Cormier; Hasam Madarati; Jeffrey Atkinson; Gonzalo Cosa; Derek A Pratt
Journal: J Am Chem Soc Date: 2013-01-18 Impact factor: 15.419

9. 9-Membered carbocycle formation: development of distinct Friedel-Crafts cyclizations and application to a scalable total synthesis of (±)-caraphenol A.

Authors: Nathan E Wright; Scott A Snyder
Journal: Angew Chem Int Ed Engl Date: 2014-03-24 Impact factor: 15.336

10. Phytochemicals perturb membranes and promiscuously alter protein function.

Authors: Helgi I Ingólfsson; Pratima Thakur; Karl F Herold; E Ashley Hobart; Nicole B Ramsey; Xavier Periole; Djurre H de Jong; Martijn Zwama; Duygu Yilmaz; Katherine Hall; Thorsten Maretzky; Hugh C Hemmings; Carl Blobel; Siewert J Marrink; Armağan Koçer; Jon T Sack; Olaf S Andersen
Journal: ACS Chem Biol Date: 2014-06-17 Impact factor: 5.100

13 in total

Review 1. Chemistry and Biology of Resveratrol-Derived Natural Products.

Authors: Mitchell H Keylor; Bryan S Matsuura; Corey R J Stephenson
Journal: Chem Rev Date: 2015-04-02 Impact factor: 60.622

2. Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers.

Authors: Kevin J Romero; Matthew S Galliher; Mark A R Raycroft; Jean-Philippe R Chauvin; Irene Bosque; Derek A Pratt; Corey R J Stephenson
Journal: Angew Chem Int Ed Engl Date: 2018-11-26 Impact factor: 15.336

10. Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G.

Authors: Youngeun Jung; Dileep Kumar Singh; Ikyon Kim
Journal: Beilstein J Org Chem Date: 2016-12-12 Impact factor: 2.883

A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

1. C11-BODIPY(581/591), an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology.

2. Total synthesis of resveratrol-based natural products: a chemoselective solution.

3. Total synthesis of hopeahainol A and hopeanol.

4. Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

Review 5. Free radical lipid peroxidation: mechanisms and analysis.

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

7. Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement.

8. Besting vitamin E: sidechain substitution is key to the reactivity of naphthyridinol antioxidants in lipid bilayers.

9. 9-Membered carbocycle formation: development of distinct Friedel-Crafts cyclizations and application to a scalable total synthesis of (±)-caraphenol A.

10. Phytochemicals perturb membranes and promiscuously alter protein function.

Review 1. Chemistry and Biology of Resveratrol-Derived Natural Products.

2. Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers.

3. Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade.

4. Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium.

5. Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.

6. Radicals in natural product synthesis.

7. Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.

Review 8. Evolution towards green radical generation in total synthesis.

Review 9. Oxidative dehydrogenative couplings of alkenyl phenols.

10. Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G.