A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities

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

doi:10.1002/anie.201409773

Cited by 66 publications

(56 citation statements)

References 53 publications

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“…The discovery that some resveratrol oligomers possess biological properties, including antifungal, antioxidant, antibacterial, antiviral, anti‐inflammatory, and antitumor properties (with some resveratrol oligomers reported to be superior to resveratrol), has continued to generate scientific interest in these derivatives. With the broad range of biological activities of resveratrol oligomers and their pharmacological potential for drug development, several research groups have successfully generated synthetic versions of these compounds with variable molecular complexity, mainly using biomimetic synthesis or de novo synthetic approaches …”

Section: Introductionmentioning

confidence: 99%

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Espinoza

Inaoka

2017

Annals of the New York Academy of Sciences

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Resveratrol has been extensively studied to investigate its biological effects, including its chemopreventive potential against cancer. Over the past decade, various resveratrol oligomers, both naturally occurring and synthetic, have been described. These resveratrol oligomers result from the polymerization of two or more resveratrol units to form dimers, trimers, tetramers, or even more complex derivatives. Some oligomers appear to have antitumor activities that are similar or superior to monomeric resveratrol. In this review, we discuss resveratrol oligomers with anticancer potential, with emphasis on well-characterized compounds, such as the dimer gnetin-C and other oligomers from Gnetum gnemon, whose safety, pharmacokinetic, and biological activities have been studied in humans.

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Section: Introductionmentioning

confidence: 99%

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Espinoza

Inaoka

2017

Annals of the New York Academy of Sciences

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“…Recently, we were able to recapitulate one mode of resveratrol oligomerization for the synthesis and antioxidant evaluation of two dimeric natural products, quadrangularin A ( 2 ) and pallidol ( 3 ) (Fig. 1) (19). The synthesis featured a remarkably persistent bis( p -quinone methide) intermediate 4a , similar to those (e.g.…”

mentioning

confidence: 99%

“…During our studies toward resveratrol dimers (19), we discovered that intermediate 4a , which was isolated as a 4:3 mixture of meso:DL diastereomers, could be quantitatively isomerized to trans,trans -indane 9 (Fig. 2), a product which can only derive from meso - 4a .…”

mentioning

confidence: 99%

Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium

Keylor

Matsuura

Grießer

et al. 2016

Science

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Persistent free radicals have become indispensable in the synthesis of organic materials by living radical polymerization. However, examples of their use in the synthesis of small molecules are rare. Herein, we report the application of persistent radical and quinone methide intermediates to the synthesis of the resveratrol tetramers nepalensinol B and vateriaphenol C. The spontaneous cleavage and reconstitution of exceptionally weak carbon-carbon bonds has enabled a stereoconvergent oxidative dimerization of racemic materials in a transformation that likely coincides with the biogenesis of these natural products. The efficient synthesis of higher-order oligomers of resveratrol will facilitate the biological studies necessary to elucidate their mechanism(s) of action.

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“…Despite a long history of isolation and biological studies of these natural products, relatively little attention has been paid by the synthetic community to chemical synthesis of polyphenolic oligostilbenoids. Most synthetic works on these unique natural products have recently appeared in the literature [4–10]. …”

Section: Introductionmentioning

confidence: 99%

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

Jung

Singh

Kim

2016

Beilstein J. Org. Chem.

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The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

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A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities

Cited by 66 publications

References 53 publications

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium

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

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