Makule, Edna and Schmidt, Thomas J. and Heilmann, Joerg and Kraus, Birgit (2017) Diarylheptanoid Glycosides of Morella salicifolia Bark. MOLECULES, 22 (12): 2266. ISSN 1420-3049,
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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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MYRICA-RUBRA; MEDICINAL-PLANTS; CONSTITUENTS; CONFIGURATION; INHIBITORS; ETHIOPIA; ARBOREA; NMR; Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:18 |
| Last Modified: | 28 Feb 2019 11:09 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1723 |
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