Abstract
Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer [corrected] seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adipocytes / cytology
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Adipocytes / drug effects
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Animals
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Borates / chemistry
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Cannabinoids / chemical synthesis*
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Cannabinoids / isolation & purification
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Cannabinoids / pharmacology
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Cell Differentiation / drug effects
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Cell Line
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Humans
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Hypoglycemic Agents / chemical synthesis*
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Hypoglycemic Agents / isolation & purification
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Hypoglycemic Agents / pharmacology
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Lipid Metabolism / drug effects
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Mice
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PPAR alpha / agonists*
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PPAR alpha / metabolism
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PPAR gamma / agonists*
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PPAR gamma / metabolism
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Plant Extracts / chemistry
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Robinia / chemistry*
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Seeds / chemistry
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Stilbenes / chemical synthesis*
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Stilbenes / isolation & purification
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Stilbenes / pharmacology
Substances
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Borates
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Cannabinoids
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Hypoglycemic Agents
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PPAR alpha
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PPAR gamma
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Plant Extracts
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Stilbenes
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amorphastilbol