About this Biochemistry, Genetics and Molecular Biology article
Geraniol-Derived Monoterpenoid Glucosides from Rhodiola rosea : Resolving Structures by QM-HifSA Methodology by Yu Tang; J. Brent Friesen; David C. Lankin; James B. McAlpine; Dejan Nikolić; Shao-Nong Chen; Guido F. Pauli is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
Monoterpenoids are integral to the chemical composition of the widely used adaptogenic dietary supplement Rhodiola rosea. The present study expands the chemical space and stereochemical information about these taxonspecific constituents from the isolation and characterization of five geraniol-derived glucosides, 1-5. While 1 and 2 exhibited almost identical NMR spectra and shared the same 2D structure ascribed to the 4-hydroxygeraniolglucoside previously described as rosiridin, the NMR-based Mosher ester method revealed the enantiomeric nature of their aglycone moieties. This marks the first report of enantiomeric aglycones among geraniol derivatives. These findings also resolve the long-standing dispute regarding the absolute configuration of rosiridin and congeneric C-4 hydroxylated geraniols and may help explain incongruent bioactivity reports of R. rosea extract. Moreover, the three previously undescribed geranioloids 3-5 were fully characterized by extensive spectroscopic analysis. Quantum mechanicsdriven 1 H iterative functionalized spin analysis (QM-HifSA) was performed for all isolates and provides detailed NMR spin parameters, with adequate decimal place precision, which e
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- Author
- Yu Tang; J. Brent Friesen; David C. Lankin; James B. McAlpine; Dejan Nikolić; Shao-Nong Chen; Guido F. Pauli
- Publisher
- American Chemical Society (ACS)
- Published
- 2023
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)