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

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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Details

Item typeArticle
Journal or Publication TitleMolecules
PublisherMDPI
Open Access TypeGold (mit APC - nicht UR)
Place of PublicationBASEL
Volume22
Page Rangep. 2266
Date2017
Date of publication29 Aug 2018 11:56
InstitutionsChemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Identification Number
ValueType
10.3390/molecules22122266DOI
KeywordsMYRICA-RUBRA; MEDICINAL-PLANTS; CONSTITUENTS; CONFIGURATION; INHIBITORS; ETHIOPIA; ARBOREA; NMR; Morella salicifolia; Myricaceae; diarylheptanoid glycosides; myricanol; juglanin
Dewey Decimal Classification600 Technology > 615 Pharmacy
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgPartially
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-376214
Item ID37621

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