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 journalArticle

11 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 languageEnglish
Pages (from-to)1100-1113
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number7
DOIs
Publication statusPublished - 2014

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Antrodia
necrosis
metabolites
Metabolites
Anti-Inflammatory Agents
tumors
Tumor Necrosis Factor-alpha
congeners
gene expression
samarium
synthesis
Cytotoxicity
Biological Products
Reporter Genes
Gene expression
chemistry
Gene Expression
products
antrocamphin A

Cite this

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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 {\circledC} The Royal Society of Chemistry.",
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Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression. / Buccini, M.; Punch, K.A.; Kaskow, Belinda; Flematti, Gavin; Skelton, Brian; Abraham, Lawrence; Piggott, Matthew.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 7, 2014, p. 1100-1113.

Research output: Contribution to journalArticle

TY - JOUR

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

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DO - 10.1039/c3ob42333f

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