文献类型：期刊文献

英文题名：Yellow Dioxobilin-Type Tetrapyrroles from Chlorophyll Breakdown in Higher Plants-A New Class of Colored Phyllobilins

作者：Li, Chengjie[1,2,3,4];Erhart, Theresia[1,2];Liu, Xiujun[1,2,5];Kraeutler, Bernhard[1,2]

机构：[1]Univ Innsbruck, Inst Organ Chem, Innrain 80-82, A-6020 Innsbruck, Austria;[2]Univ Innsbruck, CMBI, Innrain 80-82, A-6020 Innsbruck, Austria;[3]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China;[4]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China;[5]East China Univ Sci & Technol, Res Ctr Anal & Test, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2019

卷号：25

期号：16

起止页码：4052

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20190906544017);WOS:【SCI-EXPANDED(收录号:WOS:000461868900011)】；

基金：We thank Thomas Muller, Christoph Kieninger, Christoph Kreutz, and Gerhard Scherzer (Innsbruck) for help with mass spectrometry, NMR spectroscopy and HPLC analyses. We also thank Michael Oberhuber and Peter Robatscher and their team (Research Center Laimburg, Italy) for a generous supply with senescent Chardonnay leaves. This work was supported by the Austrian Science Fund (FWF, I-563 and P-28522).

语种：英文

外文关键词：green chemistry; heterocycles; photoisomerization; phyllobilin; porphyrinoids

摘要：In senescent leaves chlorophyll (Chl) catabolites typically accumulate as colorless tetrapyrroles, classified as formyloxobilin-type (or type-I) or dioxobilin-type (type-II) phyllobilins (PBs). Yellow type-I Chl catabolites (YCCs) also occur in some senescent leaves, in which they are generated by oxidation of colorless type-I PBs. A yellow type-II PB was recently proposed to occur in extracts of fall leaves of grapevine (Vitis vinifera), tentatively identified by its mass and UV/Vis absorption characteristics. Here, the first synthesis of a yellow type-II Chl catabolite (DYCC) from its presumed natural colorless type-II precursor is reported. A homogenate of a Spatiphyllum wallisii leaf was used as "green" means of effective and selective oxidation. The synthetic DYCC was fully characterized and identified with the yellow grapevine leaf pigment. As related yellow type-I PBs do, the DYCC functions as a reversible photoswitch by undergoing selective photo-induced Z/E isomerization of its C15=C16 bond.