Diarylheptanoid Glycosides of Morella salicifolia Bark
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Date
2017-12-19
Journal Title
Journal ISSN
Volume Title
Publisher
NM-AIST
Abstract
A methanolic extract of Morella salicifolia bark was fractionated by various chromatographic
techniques yielding six previously unknown cyclic diarylheptanoids, namely, 7-hydroxymyricanol
5-O-β-D-glucopyranoside (1), juglanin B 3-O-β-D-glucopyranoside (2), 16-hydroxyjuglanin B
17-O-β-D-glucopyranoside (3), myricanone 5-O-β-D-gluco-pranosyl-(1→6)-β-D-glucopyranoside (4),
neomyricanone 5-O-β-D-glucopranosyl-(1→6)-β-D-glucopyranoside (5), and myricanone
17-O-α-L-arabino-furanosyl-(1→6)-β-D-glucopyranoside (6), respectively, together with 10 known
cyclic diarylheptanoids. The structural diversity of the diarylheptanoid pattern in M. salicifolia
resulted from varying glycosidation at C-3, C-5, and C-17 as well as from substitution at C-11 with
hydroxy, carbonyl or sulfate groups, respectively. Structure elucidation of the isolated compounds
was achieved on the basis of one- and two-dimensional nuclear magnetic resonance (NMR) as well
as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) analyses. The absolute
configuration of the glycosides was confirmed after hydrolysis and synthesis of O-(S)-methyl
butyrated (SMB) sugar derivatives by comparison of their 1H-NMR data with those of reference
sugars. Additionally, absolute configuration of diarylheptanoid aglycones at C-11 was determined
by electronic circular dichroism (ECD) spectra simulation and comparison with experimental CD
spectra after hydrolysis
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This research article was published by Molecules 2017, 22(12)
Keywords
Morella salicifolia, Myricaceae, diarylheptanoid glycosides, myricanol, juglanin