Noreudesmane sesquiterpenoids from the leaves of Nicotiana tabacum

Abstract

Six new 14-noreudesmane sesquiterpenoids, nicotabacosides A-F (1-6), along with five known sesquiterpenoids (7-11), were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1-6 were elucidated as isorishitin 3-O-β-D-glucopyranoside (1), rishitin 3-O-β-D-glucopyranoside (2), rishitin 2-O-β-D-glucopyranoside (3), 1, 6-dehydro-rishitin 3-O-β-D-glucopyranoside (4), 2-hydroxyl-ligudentatol 3-O-β-D-glucopyranoside (5) and oxyglutinosone 3-O-β-D-glucopyranoside (6) based on extensive spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR). Their absolute configurations were determined by X-ray single-crystal diffraction and comparison of their electronic circular dichroism (ECD) spectra.

Keywords: 14-Noreudesmane sesquiterpenoids; Nicotabacosides A–F; Nicotiana tabacum.