Photoprotolytic Processes of Umbelliferone and Proposed Function in Resistance to Fungal Infection

Ron Simkovitch, Dan Huppert

Research output: Contribution to journalArticlepeer-review

Abstract

The photoprotolytic processes of 7-hydroxy-coumarin (Umb) were investigated by steady-state and time-resolved-fluorescence techniques. We found that the Umb compound is a photoacid with pKa∗ ≈0.4 and a rate constant of the excited-state proton transfer (ESPT) to water of 2 × 1010 s-1. Umb is also a photobase and accepts an excess proton in solution and also directly from weak acids like acetic acid. When Umb is adsorbed on cellulose it also functions as a photoacid and a photobase. Hydroxycoumarins are known to accumulate next to fungal-, bacterial-, and viral-infected regions in the leaves and stems of plants in general and also in trees. We propose that these compounds when irradiated by sunlight UV, combat the fungi or bacteria by excited-state proton-transfer reactions. These photoprotolytic reactions provide a universal resistance mechanism to infections in plants.

Original languageEnglish
Pages (from-to)14683-14696
Number of pages14
JournalJournal of Physical Chemistry B
Volume119
Issue number46
DOIs
StatePublished - 19 Nov 2015

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