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Diarylheptanoid Glycosides of Morella salicifolia Bark

Department of Pharmaceutical Biology, Faculty of Chemistry and Pharmacy, Universität Regensburg, Universitätsstraße 31, D-93053 Regensburg, Germany
Department of Food Biotechnology and Nutritional Sciences, Nelson Mandela African Institution of Science and Technology, P.O. Box 447 Arusha, Tanzania
Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Westfälische Wilhelms-Universität Münster, PharmaCampus—Corrensstraße 48, D-48149 Münster, Germany
Authors to whom correspondence should be addressed.
Molecules 2017, 22(12), 2266;
Received: 26 October 2017 / Revised: 2 December 2017 / Accepted: 4 December 2017 / Published: 19 December 2017
(This article belongs to the Section Natural Products Chemistry)
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. View Full-Text
Keywords: Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin
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MDPI and ACS Style

Makule, E.; Schmidt, T.J.; Heilmann, J.; Kraus, B. Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules 2017, 22, 2266.

AMA Style

Makule E, Schmidt TJ, Heilmann J, Kraus B. Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules. 2017; 22(12):2266.

Chicago/Turabian Style

Makule, Edna, Thomas J. Schmidt, Jörg Heilmann, and Birgit Kraus. 2017. "Diarylheptanoid Glycosides of Morella salicifolia Bark" Molecules 22, no. 12: 2266.

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