| Veröffentlichte Version Download ( PDF | 2MB) | Lizenz: Creative Commons Namensnennung 4.0 International |
Diarylheptanoid glycosides of Myrica salicifolia bark
Artikel
Makule, Edna, Schmidt, Thomas J., Heilmann, Jörg und Kraus, Birgit (2017) Diarylheptanoid glycosides of Myrica salicifolia bark. Molecules 22, S. 2266.DOI zum Zitieren dieses Dokuments: 10.5283/epub.41562
Zusammenfassung
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 ...
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.
Alternative Links zum Volltext
Beteiligte Einrichtungen
Details
| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Molecules | ||||
| Verlag | Molecular Diversity Preservation International (MDPI) | ||||
| Band | 22 | ||||
| Seitenbereich | S. 2266 | ||||
| Datum | 2017 | ||||
| Veröffentlichungsdatum | 12 Feb 2020 11:55 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer |
| ||||
| Stichwörter / Keywords | Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin | ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-415626 | ||||
| Dokumenten-ID | 41562 |
Downloadstatistik
Downloadstatistik