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Function-oriented synthesis applied to the anti-botulinum natural product toosendanin

Academic Article
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Overview

authors

  • Dickerson, Tobin
  • Janda, Kim
  • Tepp, W. H.
  • Nakai, Y.
  • Johnson, E. A.

publication date

  • February 2009

journal

  • Bioorganic & Medicinal Chemistry  Journal

abstract

  • Botulinum neurotoxins (BoNTs) are the etiological agents responsible for botulism, a disease characterized by peripheral neuromuscular blockade and a characteristic flaccid paralysis of humans. The natural product toosendanin is a traditional Chinese medicine which has been reported to have anti-botulinum properties in animal models. To establish what chemical functionalities are necessary for the anti-botulinum properties found within toosendanin, a study was initiated with the goal of using function-oriented synthesis (FOS) as a strategy to begin to unravel toosendanin's powerful anti-botulinum properties. From these studies a new synthetic strategy is put forth allowing access to a 4-acetoxy CD fragment analogue (14) of toosendanin, which was achieved from mesityl oxide and acetylacetone in 14 steps. Animal studies on this fragment are also reported.

subject areas

  • Animals
  • Botulinum Toxins
  • Botulism
  • Clostridium botulinum
  • Drugs, Chinese Herbal
  • Limonins
  • Medicine, Chinese Traditional
  • Mice
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Research

keywords

  • 4-Acetoxy CD fragment
  • Botulinum neurotoxins
  • Function-oriented synthesis (FOS)
  • Toosendanin
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Identity

PubMed Central ID

  • PMC2661763

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/j.bmc.2008.12.042

PubMed ID

  • 19131252
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Additional Document Info

start page

  • 1152

end page

  • 1157

volume

  • 17

issue

  • 3

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