文献类型：期刊文献

英文题名：Novel Types of Hypermodified Fluorescent Phyllobilins from Breakdown of Chlorophyll in Senescent Leaves of Grapevine (Vitis vinifera)

作者：Erhart, Theresia[1,2];Mittelberger, Cecilia[3];Liu, Xiujun[1,2,4];Podewitz, Maren[5];Li, Chengjie[1,2,6,7];Scherzer, Gerhard[1,2];Stoll, Gertrud[3];Valls, Josep[3,8];Robatscher, Peter[3];Liedl, Klaus R.[5];Oberhuber, Michael[3];Kraeutler, Bernhard[1,2]

机构：[1]Univ Innsbruck, Inst Organ Chem, Innrain 80-82, A-6020 Innsbruck, Austria;[2]Univ Innsbruck, Ctr Mol Biosci, Innrain 80-82, A-6020 Innsbruck, Austria;[3]Laimburg Res Ctr, Laimburg 6 Pfatten Vadena, I-39040 Auer Ora, BZ, Italy;[4]East China Univ Sci & Technol, Res Ctr Anal & Test, Meilong Rd 130, Shanghai 200237, Peoples R China;[5]Univ Innsbruck, Inst Gen Inorgan & Theoret Chem, Innrain 80-82, A-6020 Innsbruck, Austria;[6]East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China;[7]East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China;[8]Univ Bordeaux, Fac Pharmaceut Sci, Unite Rech Enol EA 4577, F-33882 Villenave Dornon, France

年份：2018

卷号：24

期号：65

起止页码：17268

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20184506039690);WOS:【SCI-EXPANDED(收录号:WOS:000451233400016)】；

基金：We are grateful to Thomas Muller, Hacer Yalcinkaya, Iris Sussenbacher, Clemens Vergeiner and Stefan Vergeiner for their help with HPLC-analytical and mass spectrometric tasks. We are grateful to Sandra Schumacher for collecting leaf samples. We are also grateful for generous financial support by the Interreg IV Italy-Austria program (ERDF; project "Biophytirol" Nr. 5345 CUP: B25E11000300007), by the Austrian Science Fund (FWF, projects No. L-472 and P-28522; to B.K.) and by the Autonomous Province of Bozen (Bolzano; to M.O.). M.P. would like to thank the Austrian Science FWF for a Lise Meitner Fellowship (M-2005). The computational results presented were obtained using the HPC infrastructure LEO of the University of Innsbruck.

语种：英文

外文关键词：fluorescence; glycosides; phyllobilin; porphyrinoid; senescence

摘要：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 (bcPBs), suggests the activity of an unknown enzyme that forges the 20-membered macroring at the tetrapyrrolic core of a fluorescent PB. bcPBs 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.