| Autor: |
Forster LC; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia., Pierens GK; Centre for Advanced Imaging, The University of Queensland, Brisbane, QLD 4072, Australia., Clegg JK; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia., Garson MJ; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia. |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of natural products [J Nat Prod] 2020 Mar 27; Vol. 83 (3), pp. 714-719. Date of Electronic Publication: 2020 Jan 08. |
| DOI: |
10.1021/acs.jnatprod.9b01051 |
| Abstrakt: |
Two new oxygenated terpenes ( 1 and 2 ) have been characterized from the Australian nudibranch Goniobranchus coi . Broadened 1 H NMR signals, together with the absence of individual carbon NMR signals, complicated analysis of 5,9-epoxydendrillolide A ( 1 ); increasing the temperature to 323 K revealed the missing NMR signals. Low-temperature 1 H NMR experiments provided an activation barrier of ∼15 kcal mol -1 and, together with DFT calculations, supported interconversion of a twist chair conformer with two different chair conformers. X-ray crystallographic analysis coupled with biosynthetic reasoning suggested a (5 R , 8 S , 9 R , 13 R , 14 R , 15 R , 16 R ) configuration. Ketone 2 demonstrated similar dynamic conformational processes to 1 . |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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