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.

• Authors: Marco Buccini, Kathryn A Punch, Belinda Kaskow, Gavin R Flematti, Brian W Skelton, Lawrence J Abraham, Matthew J Piggott
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 12 Issue 7 Pg. 1100-13 (Feb 21 2014) ISSN: 1477-0539 [Electronic] England
• PMID: 24385001 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkynes
• Anisoles
• Biological Products
• Receptors, Tumor Necrosis Factor
• antrocamphin A

Topics

• Alkynes (chemistry, metabolism, pharmacology)
• Anisoles (chemistry, metabolism, pharmacology)
• Antrodia (chemistry, metabolism)
• Biological Products (chemistry, metabolism, pharmacology)
• Cell Death (drug effects)
• Cell Line
• Dose-Response Relationship, Drug
• Humans
• Molecular Structure
• Receptors, Tumor Necrosis Factor (antagonists & inhibitors, genetics)
• Structure-Activity Relationship