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Novel Types of Hypermodified Fluorescent Phyllobilins from Breakdown of Chlorophyll in Senescent Leaves of Grapevine ( Vitis vinifera )
Author(s) -
Erhart Theresia,
Mittelberger Cecilia,
Liu Xiujun,
Podewitz Maren,
Li Chengjie,
Scherzer Gerhard,
Stoll Gertrud,
Valls Josep,
Robatscher Peter,
Liedl Klaus R.,
Oberhuber Michael,
Kräutler Bernhard
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803128
Subject(s) - vitis vinifera , catabolite repression , fluorescence , botany , chlorophyll , viticulture , chemistry , wine , biology , biochemistry , food science , mutant , physics , quantum mechanics , gene
The tetrapyrrolic chlorophyll catabolites (or phyllobilins, PBs) were analyzed in yellow fall leaves of the grape Chardonnay, a common Vitis vinifera white wine cultivar. The major fractions in leaf extracts of V. vinifera , tentatively assigned to PBs, were isolated and their structures elucidated. The dominant fraction is a dioxobilin‐type non‐fluorescent Chl‐catabolite of a previously observed type. Two less polar fluorescent PBs were characterized as a novel dioxobilin‐type fluorescent Chl‐catabolite with a bicyclo‐1′,6′‐glycosyl architecture, and its new fluorescent formyloxobilin‐type analogue. The discovery of persistent hypermodified fluorescent PBs with the architecture of bicyclo‐[17.3.1]‐PBs ( bc PBs), suggests the activity of an unknown enzyme that forges the 20‐membered macroring at the tetrapyrrolic core of a fluorescent PB. bc PBs may play specific physiological roles in grapevine plants and represent endogenous anti‐infective agents, as found similarly for other organic bicyclo‐[ n .3.1]‐1′,6′‐glycosyl derivatives.