Title |
Conformational analysis of an anti-androgenic, (E,E)-8-hydroxygermacrene B, using NOESY and dynamic NMR spectroscopy
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Published in |
Bioorganic & Medicinal Chemistry Letters, May 2014
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DOI | 10.1016/j.bmcl.2014.05.057 |
Pubmed ID | |
Authors |
Jukkarin Srivilai, Nantaka Khorana, Neti Waranuch, Nungruthai Suphrom, Kornkanok Ingkaninan |
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. |
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