2. Academic Validation
  3. Stereoisomeric Composition of Natural Myrtucommulone A

Stereoisomeric Composition of Natural Myrtucommulone A

  • J Nat Prod. 2015 Oct 23;78(10):2381-9. doi: 10.1021/acs.jnatprod.5b00358.
Marcus Hans 1,  Maël Charpentier 1,  Volker Huch 2,  Johann Jauch 1,  Torsten Bruhn 3,  Gerhard Bringmann 3,  Dietmar Quandt 4
Affiliations

Affiliations

  • 1 Institute of Organic Chemistry, Saarland University , Campus C 4.2, 66123 Saarbrücken, Germany.
  • 2 Institute of Inorganic Chemistry, Saarland University , Campus C 4.1, 66123 Saarbrücken, Germany.
  • 3 Institute of Organic Chemistry, University of Würzburg , Am Hubland, 97074 Würzburg, Germany.
  • 4 Nees-Institute for Biodiversity of Plants, University of Bonn , Meckenheimer Allee 170, 53115 Bonn, Germany.
PMID: 26457652 DOI: 10.1021/acs.jnatprod.5b00358
Abstract

Myrtucommulone A (MC A) (1), isolated from Myrtus communis (myrtle), shows the same pharmacological activity for inhibition of inflammation and induction of Apoptosis as synthetic MC A, which consists of three stereoisomers, i.e., two enantiomers and one meso form. This led to the question of whether the natural MC A is a pure stereoisomer or a mixture of stereoisomers. The specific rotation and electronic circular dichroism (ECD) data of natural MC A (1) as well as of a pentacyclic derivative 4 revealed that naturally occurring MC A (1) consists of the racemate and the meso form in a 1:1 ratio. A probable precursor of MC A (1), nor-semimyrtucommulone (5), was also isolated from myrtle as a racemate. The absolute configurations of the enantiomers of 1 and 5 were determined using a combination of experimental and quantum-chemical calculated ECD spectra.

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