Related Experiment Video
Updated: Apr 27, 2026

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition
Published on: May 17, 2024
Conformational analysis of an anti-androgenic, (E,E)-8-hydroxygermacrene B, using NOESY and dynamic NMR spectroscopy
Jukkarin Srivilai1, Nantaka Khorana2, Neti Waranuch3
1Bioscreening Unit, Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Phitsanulok 65000, Thailand.
Abstract:
(E,E)-8-Hydroxygermacrene B was prepared by ketone reduction of germacrone, a naturally occurring compound from Curcuma aeruginosa Roxb. with NaBH4 at low temperature (4 °C). This compound showed remarkable in vitro anti-androgenic activity (IC50 0.15±0.022 mM) applicable to male baldness treatments. NMR analysis at -50 °C indicated that there were four conformational isomers of (E,E)-8-hydroxygermacrene B in a ratio of 48:40:8:4. The major conformers were assigned by (1)H NMR and 2D-NOESY NMR spectroscopy as having methyl groups at C-10 and C-4 in up-down (UD) orientations (48% predominance) and UU (40%). (1)H NMR spectra implied another two minor conformers with these methyls having DU (8%) and DD (4%) orientations.
More Related Videos
Related Concept Videos
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR
NMR Spectroscopy of Aromatic Compounds
NMR Spectroscopy of Benzene Derivatives
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
2D NMR: Overview of Heteronuclear Correlation Techniques

