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

Diarylheptanoid Glycosides of Morella salicifolia Bark

Makule, Edna, Schmidt, Thomas J. , Heilmann, Jörg und Kraus, Birgit (2017) Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules 22, S. 2266.

Veröffentlichungsdatum dieses Volltextes: 29 Aug 2018 11:56
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.37621


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--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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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftMolecules
Verlag:MDPI
Ort der Veröffentlichung:BASEL
Band:22
Seitenbereich:S. 2266
Datum2017
InstitutionenChemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann)
Identifikationsnummer
WertTyp
10.3390/molecules22122266DOI
Stichwörter / KeywordsMYRICA-RUBRA; MEDICINAL-PLANTS; CONSTITUENTS; CONFIGURATION; INHIBITORS; ETHIOPIA; ARBOREA; NMR; Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin
Dewey-Dezimal-Klassifikation600 Technik, Medizin, angewandte Wissenschaften > 615 Pharmazie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenZum Teil
URN der UB Regensburgurn:nbn:de:bvb:355-epub-376214
Dokumenten-ID37621

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