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Open AccessArticle

Diarylheptanoid Glycosides of Morella salicifolia Bark

1
Department of Pharmaceutical Biology, Faculty of Chemistry and Pharmacy, Universität Regensburg, Universitätsstraße 31, D-93053 Regensburg, Germany
2
Department of Food Biotechnology and Nutritional Sciences, Nelson Mandela African Institution of Science and Technology, P.O. Box 447 Arusha, Tanzania
3
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; https://doi.org/10.3390/molecules22122266
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.

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