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Makule, Edna ; Schmidt, Thomas J. ; Heilmann, Jörg ; Kraus, Birgit

Diarylheptanoid glycosides of Myrica salicifolia bark

Makule, Edna, Schmidt, Thomas J., Heilmann, Jörg und Kraus, Birgit (2017) Diarylheptanoid glycosides of Myrica salicifolia bark. Molecules 22, S. 2266.

Veröffentlichungsdatum dieses Volltextes: 12 Feb 2020 11:55
Artikel
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.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftMolecules
Verlag:Molecular Diversity Preservation International (MDPI)
Band:22
Seitenbereich:S. 2266
Datum2017
InstitutionenChemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann)
Identifikationsnummer
WertTyp
10.3390/molecules22122266DOI
Stichwörter / KeywordsMorella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-415626
Dokumenten-ID41562

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