13C-NMR Study of the Ruthenium(II)-Catalyzed Degradation of Labeled G-Factor Endoperoxides: Proposal of a Likely Biogenetic Pathway and Evidence for CO2 Release
✍ Scribed by Christiane André-Barrès; Michel Baltas; Stéphane Massou
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 361 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1612-1872
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✦ Synopsis
Abstract
G‐factor endoperoxides are natural products acting as phytohormones and contribute to root inhibition and frost resistance in Eucalyptus grandis and other Myrtaceae. Several (Z)‐ and (E)‐configured cyclopentane‐1,3‐dione metabolites of G‐factors have been found in some Eucalyptus extracts. Interestingly, these probable metabolites are identical to the products obtained by Ru^II^‐catalyzed reduction of G‐factors. In the present work, we, thus, studied the mechanism involved in the formation of these compounds by means of in‐depth NMR distribution analysis of two differently ^13^C‐labeled G~3~‐factors. The observed CO~2~ release is underlined, and a comparison with the corresponding Fe^II^‐induced degradation of G‐factor endoperoxides is made. Also, the type of electron transfer proposed in the two processes is discussed and, tentatively, connected to the role of endoperoxides in plants.