Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression

M. Buccini; K.A. Punch; Belinda Kaskow; Gavin Flematti; Brian Skelton; Lawrence Abraham; Matthew Piggott

doi:10.1039/c3ob42333f

Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression

M. Buccini, K.A. Punch, Belinda Kaskow, Gavin Flematti, Brian Skelton, Lawrence Abraham, Matthew Piggott

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity. This journal is © The Royal Society of Chemistry.

Original language	English
Pages (from-to)	1100-1113
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	7
DOIs	https://doi.org/10.1039/c3ob42333f
Publication status	Published - 2014

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title = "Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression",

abstract = "An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity. This journal is {\textcopyright} The Royal Society of Chemistry.",

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T1 - Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression

AU - Buccini, M.

AU - Punch, K.A.

AU - Kaskow, Belinda

AU - Flematti, Gavin

AU - Skelton, Brian

AU - Abraham, Lawrence

AU - Piggott, Matthew

PY - 2014

Y1 - 2014

N2 - An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity. This journal is © The Royal Society of Chemistry.

AB - An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity. This journal is © The Royal Society of Chemistry.

U2 - 10.1039/c3ob42333f

DO - 10.1039/c3ob42333f

M3 - Article

C2 - 24385001

VL - 12

SP - 1100

EP - 1113

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 7

ER -