Next Article in Journal
Quinoline-Based Hybrid Compounds with Antimalarial Activity
Previous Article in Journal
Domain IV of Annexin A5 Is Critical for Binding Calcium and Guarantees Its Maximum Binding to the Phosphatidylserine Membrane
Article Menu
Issue 12 (December) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(12), 2266;

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.
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)
Full-Text   |   PDF [2336 KB, uploaded 19 December 2017]   |  


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

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top