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Diarylheptanoid Glycosides of Morella salicifolia Bark
Article
Makule, Edna, Schmidt, Thomas J.
, Heilmann, Jörg and Kraus, Birgit
(2017)
Diarylheptanoid Glycosides of Morella salicifolia Bark.
Molecules 22, p. 2266.
DOI to cite this document: 10.5283/epub.37621
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--d-glucopyranoside (1), juglanin B 3-O--d-glucopyranoside (2), 16-hydroxyjuglanin B 17-O--d-glucopyranoside (3), myricanone 5-O--d-gluco-pranosyl-(16)--d-glucopyranoside (4), neomyricanone ...
A methanolic extract of Morella salicifolia bark was fractionated by various chromatographic techniques yielding six previously unknown cyclic diarylheptanoids, namely, 7-hydroxymyricanol 5-O--d-glucopyranoside (1), juglanin B 3-O--d-glucopyranoside (2), 16-hydroxyjuglanin B 17-O--d-glucopyranoside (3), myricanone 5-O--d-gluco-pranosyl-(16)--d-glucopyranoside (4), neomyricanone 5-O--d-glucopranosyl-(16)--d-glucopyranoside (5), and myricanone 17-O--l-arabino-furanosyl-(16)--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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| Item type | Article | ||||
| Journal or Publication Title | Molecules | ||||
| Publisher | MDPI | ||||
| Open Access Type | Gold (mit APC - nicht UR) | ||||
| Place of Publication | BASEL | ||||
| Volume | 22 | ||||
| Page Range | p. 2266 | ||||
| Date | 2017 | ||||
| Date of publication | 29 Aug 2018 11:56 | ||||
| Institutions | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) | ||||
| Identification Number |
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| Keywords | MYRICA-RUBRA; MEDICINAL-PLANTS; CONSTITUENTS; CONFIGURATION; INHIBITORS; ETHIOPIA; ARBOREA; NMR; Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin | ||||
| Dewey Decimal Classification | 600 Technology > 615 Pharmacy | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-376214 | ||||
| Item ID | 37621 |
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