Diarylheptanoid Glycosides of Morella salicifolia Bark
AbstractA 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. View Full-Text
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Makule, E.; Schmidt, T.J.; Heilmann, J.; Kraus, B. Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules 2017, 22, 2266.
Makule E, Schmidt TJ, Heilmann J, Kraus B. Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules. 2017; 22(12):2266.Chicago/Turabian Style
Makule, Edna; Schmidt, Thomas J.; Heilmann, Jörg; Kraus, Birgit. 2017. "Diarylheptanoid Glycosides of Morella salicifolia Bark." Molecules 22, no. 12: 2266.
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