Regioselective reactions for programmable resveratrol oligomer synthesis

Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the ‘French paradox’—the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in satur...

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Published inNature (London) Vol. 474; no. 7352; pp. 461 - 466
Main Authors Snyder, Scott A., Gollner, Andreas, Chiriac, Maria I.
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 22.06.2011
Nature Publishing Group
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Abstract Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the ‘French paradox’—the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in saturated fats—the oligomers of resveratrol have been largely ignored despite their high biological activity. Challenges in achieving their isolation in sufficient quantity from natural sources, coupled with an inability to prepare them easily synthetically, are seen as the main obstacles. Here we report a programmable, controlled and potentially scalable synthesis of the resveratrol family via a three-stage design. The synthetic approach requires strategy- and reagent-guided chemical functionalizations to differentiate two distinct cores possessing multiple sites with the same or similar reactivity, ultimately leading to five higher-order natural products. This work demonstrates that challenging, positionally selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, it provides materials and tools with which to unlock the full biochemical potential of this family of natural products, and it affords an intellectual framework within which other oligomeric families could potentially be accessed. Resveratrol oligomers succumb to synthesis The natural plant defence molecule resveratrol has captured the public imagination thanks to its various beneficial effects in mice and its presence in red wine. But it may be the resveratrol oligomers that have more long-term potential as pharmaceuticals. They occur naturally and have a broad range of potent biological activities, but their complexity makes rational synthesis of new drug candidates very challenging. Snyder et al . now present a new three-stage strategy that should improve matters: it is programmable, controlled and potentially scalable. Similar principles should be transferable to other oligomeric families.
AbstractList Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the 'French paradox'-the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in saturated fats-the oligomers of resveratrol have been largely ignored despite their high biological activity. Challenges in achieving their isolation in sufficient quantity from natural sources, coupled with an inability to prepare them easily synthetically, are seen as the main obstacles. Here we report a programmable, controlled and potentially scalable synthesis of the resveratrol family via a three-stage design. The synthetic approach requires strategy- and reagent-guided chemical functionalizations to differentiate two distinct cores possessing multiple sites with the same or similar reactivity, ultimately leading to five higher-order natural products. This work demonstrates that challenging, positionally selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, it provides materials and tools with which to unlock the full biochemical potential of this family of natural products, and it affords an intellectual framework within which other oligomeric families could potentially be accessed.
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants throughout the world and credited as potentially being responsible for the so-called “French paradox” given its broad spectrum activity, the hundreds of oligomeric materials derived from it have been largely ignored despite their similarly high biochemical potential. Challenges in achieving their isolation in quantity from natural sources, coupled with an inability to rationally prepare them in the laboratory, are the main culprits. Here we show that a programmable, controlled, and potentially scaleable synthesis of the resveratrol family is possible through a unique three-stage design. These efforts required novel tactics coupled with strategy- and reagent-guided functionalizations to differentiate two distinct cores possessing multiple sites with the same and/or similar reactivity, ultimately leading to five higher-order natural products. We anticipate that this work 1) demonstrates that challenging, positionally-selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, 2) provides materials and tools to finally unlock the full biochemical potential of the family, particularly from the standpoint of activity and drug-property optimization, and 3) affords an intellectual framework to potentially access other oligomeric families controllably.
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the ‘French paradox’—the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in saturated fats—the oligomers of resveratrol have been largely ignored despite their high biological activity. Challenges in achieving their isolation in sufficient quantity from natural sources, coupled with an inability to prepare them easily synthetically, are seen as the main obstacles. Here we report a programmable, controlled and potentially scalable synthesis of the resveratrol family via a three-stage design. The synthetic approach requires strategy- and reagent-guided chemical functionalizations to differentiate two distinct cores possessing multiple sites with the same or similar reactivity, ultimately leading to five higher-order natural products. This work demonstrates that challenging, positionally selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, it provides materials and tools with which to unlock the full biochemical potential of this family of natural products, and it affords an intellectual framework within which other oligomeric families could potentially be accessed. Resveratrol oligomers succumb to synthesis The natural plant defence molecule resveratrol has captured the public imagination thanks to its various beneficial effects in mice and its presence in red wine. But it may be the resveratrol oligomers that have more long-term potential as pharmaceuticals. They occur naturally and have a broad range of potent biological activities, but their complexity makes rational synthesis of new drug candidates very challenging. Snyder et al . now present a new three-stage strategy that should improve matters: it is programmable, controlled and potentially scalable. Similar principles should be transferable to other oligomeric families.
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the 'French paradox'-the observation that French people have a relatively low incidence of coronary heart disease, even though their diet is high in saturated fats-the oligomers of resveratrol have been largely ignored despite their high biological activity. Challenges in achieving their isolation in sufficient quantity from natural sources, coupled with an inability to prepare them easily synthetically, are seen as the main obstacles. Here we report a programmable, controlled and potentially scalable synthesis of the resveratrol family via a three-stage design. The synthetic approach requires strategy- and reagent-guided chemical functionalizations to differentiate two distinct cores possessing multiple sites with the same or similar reactivity, ultimately leading to five higher-order natural products. This work demonstrates that challenging, positionally selective functionalizations of complex materials are possible where biosynthetic studies have indicated otherwise, it provides materials and tools with which to unlock the full biochemical potential of this family of natural products, and it affords an intellectual framework within which other oligomeric families could potentially be accessed. [PUBLICATION ABSTRACT]
Audience Academic
Author Snyder, Scott A.
Gollner, Andreas
Chiriac, Maria I.
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  surname: Snyder
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  surname: Chiriac
  fullname: Chiriac, Maria I.
  organization: Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA
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2015 INIST-CNRS
COPYRIGHT 2011 Nature Publishing Group
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IsDoiOpenAccess true
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Issue 7352
Keywords Heart
Chemical reagent
Regioselectivity
Biosynthesis
Selectivity
Natural compound
Saturated fat
Oligomer
Biological activity
Stilbene derivatives
Plant
Polyphenol
Functionalization
Phytoalexin
Heart disease
Plant origin
Resveratrol
Phenols
Benzenic compound
Chemical reactivity
Chemical synthesis
Language English
License CC BY 4.0
http://www.springer.com/tdm
Users may view, print, copy, download and text and data- mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms
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Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ObjectType-Article-2
ObjectType-Feature-1
S.A.S. conceived and directed the research, as well as composed the manuscript. A.G. developed the dihydrofuran synthesis approach and completed compounds 16, 17, 30, and 38. M.I.C. completed compound 19 as well as the majority of the route towards compound 18 including the BDSB-based functionalization. Both A.G. and M.I.C. worked to complete 18, and provided commentary and feedback on the manuscript.
Author Contributions
OpenAccessLink https://pubmed.ncbi.nlm.nih.gov/PMC3179663
PMID 21697944
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Snippet Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the ‘French...
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants and credited as potentially being responsible for the 'French...
Although much attention has been devoted to resveratrol, a unique polyphenol produced by plants throughout the world and credited as potentially being...
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springer
SourceType Open Access Repository
Aggregation Database
Index Database
Publisher
StartPage 461
SubjectTerms 639/638/403/934
639/638/549
Biochemistry
Biological Products - biosynthesis
Biological Products - chemical synthesis
Biological Products - chemistry
Bromine - chemistry
Cardiovascular diseases
Chemical properties
Chemical reactions
Chemical reactivity
Chemical research
Chemical synthesis
Chemistry
Chemistry, Pharmaceutical - methods
Diets
Exact sciences and technology
Flavonoids - chemistry
Halogenation
Health aspects
Heart diseases
Humanities and Social Sciences
Indicators and Reagents - chemistry
Isomerism
Mass spectrometry
Materials selection
Methods
multidisciplinary
Natural products
Noncondensed benzenic compounds
Observations
Oligomers
Organic chemistry
Phenols - chemistry
Polycyclic Compounds - chemistry
Polyphenols
Preparations and properties
Production processes
Reactivity and mechanisms
Resveratrol
Science
Science (multidisciplinary)
Stilbenes - chemical synthesis
Stilbenes - chemistry
Stilbenes - metabolism
Structure
Substrate Specificity
Synthesis
Terpenes - chemistry
Title Regioselective reactions for programmable resveratrol oligomer synthesis
URI https://link.springer.com/article/10.1038/nature10197
https://www.ncbi.nlm.nih.gov/pubmed/21697944
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https://search.proquest.com/docview/873704399
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https://pubmed.ncbi.nlm.nih.gov/PMC3179663
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