Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 28, Pages 9498-9503Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601739
Keywords
chlorophyll; glycoside; natural products; plant senescence; tetrapyrrole
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Funding
- Austrian National Science Foundation (FWF) [I-563, P-28522]
- Bundesministerium fur Wissenschaft, Forschung und Wirtschaft (BMWFW) [SPA/02-88]
- Austrian Science Fund (FWF) [P28522] Funding Source: Austrian Science Fund (FWF)
- Austrian Science Fund (FWF) [I 563, P 28522] Funding Source: researchfish
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Fall leaves of the common wych elm tree (Ulmus glabra) were studied with respect to chlorophyll catabolites. Over a dozen colorless, non-fluorescent chlorophyll catabolites (NCCs) and several yellow chlorophyll catabolites (YCCs) were identified tentatively. Three NCC fractions were isolated and their structures were characterized by spectroscopic means. Two of these, Ug-NCC-27 and Ug-NCC-43, carried a glucopyranosyl appendage. Ug-NCC-53, the least polar of these NCCs, was identified as the formal product of an intramolecular esterification of the propionate and primary glucopyranosyl hydroxyl groups of Ug-NCC-43. Thus, the glucopyranose moiety and three of the pyrrole units of Ug-NCC-53 span a 20-membered ring, installing a bicyclo[17.3.1] glycoside moiety. This structural motif is unprecedented in heterocyclic natural products, according to a thorough literature search. The remarkable, three-dimensional bicyclo[17.3.1]-glycoside architecture reduces the flexibility of the linear tetrapyrrole. This feature of Ug-NCC-53 is intriguing, considering the diverse biological effects of known bicyclo[n.3.1]glycosidic natural products.
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