RRC ID 60889
Author Nakashima T, Nambu Y, Inoue Y, Masimbula R, Matsuura H.
Title Pennelliisides A-C, 2,3,4-Trisubstituted Acyl Glucoses Isolated from Solanum pennellii.
Journal J Nat Prod
Abstract Solanum 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 α and β 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.
Volume 83(8)
Pages 2337-2346
Published 2020-8-28
DOI 10.1021/acs.jnatprod.9b01234
PMID 32803973
MeSH Acylation Glucose / analogs & derivatives* Glucose / isolation & purification Herbicides / chemistry Herbicides / pharmacology Molecular Structure Solanum / chemistry* Spectrum Analysis / methods
IF 3.782
Tomato TOMJPF00008