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Pennelliisides A-C, 2,3,4-Trisubstituted Acyl Glucoses Isolated from Solanum pennellii

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Title: Pennelliisides A-C, 2,3,4-Trisubstituted Acyl Glucoses Isolated from Solanum pennellii
Authors: Nakashima, Tenki Browse this author
Nambu, Yurika Browse this author
Inoue, Yutaka Browse this author
Masimbula, Rishni Browse this author
Matsuura, Hideyuki Browse this author →KAKEN DB
Issue Date: 28-Aug-2020
Publisher: American Chemical Society
Journal Title: Journal of Natural Products
Volume: 83
Issue: 8
Start Page: 2337
End Page: 2346
Publisher DOI: 10.1021/acs.jnatprod.9b01234
Abstract: Solarium species accumulate a variety of secondary metabolites in their trichomes, and it is well known that acyl sugars are specialized metabolites secreted by the trichomes. However, very few reports provide detailed information on the chemical structure of polyacylated glucose derivatives, due to the alpha and beta isomerization that can occur at the C-1 position. In this study, a strategy was established to isolate polyacylated glucose derivatives. According to the developed strategy, hydroxy groups were derivatized to a benzyloxy group using TriBOT. After isolation of the compounds in pure form and deprotection of the benzyloxy group, the chemical structures of pennelliisides A-C were determined as 2,3,4-O-triisobutyryl-D-glucose, 3-O-(8-methylnonanoyl)-2,4-O-diisobutyryl-D-glucose, and 3-O-decanoyl-2,4-O-diisobutyryl-D-glucose, respectively. Structural elucidation was performed using spectroscopic techniques, including 1D and 2D NMR, FD-MS, and GC-MS. It was also found that the fatty acid moiety contributes to the allelopathic properties of the isolated compounds.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Type: article (author version)
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 松浦 英幸

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