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J Biol Chem, Vol. 273, Issue 25, 15335-15339, June 19, 1998

The Key Step in Chlorophyll Breakdown in Higher Plants
CLEAVAGE OF PHEOPHORBIDE a MACROCYCLE BY A MONOOXYGENASE

Stefan HörtensteinerDagger , Karin Lynn WüthrichDagger , Philippe MatileDagger , Karl-Hans Onganiaparallel , and Bernhard Kräutlerparallel

From the Dagger  Department of Plant Biology, University of Zürich, Zollikerstrasse 107, CH-8008 Zürich, Switzerland and the parallel  Institute of Organic Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria

Chlorophyll breakdown in green plants is a long-standing biological enigma. Recent work has shown that pheophorbide a (Pheide a) derived from chlorophyll (Chl) is converted oxygenolytically into a primary fluorescent catabolite (pFCC-1) via a red Chl catabolite (RCC) intermediate. RCC, the product of the ring cleavage reaction catalyzed by Pheide a oxygenase, which is suggested to be the key enzyme in Chl breakdown in green plants, is converted into pFCC-1 by a reductase. In the present study, an in vitro assay comprising 18O2 Pheide a oxygenase and RCC reductase yielded labeled pFCC-1. Fast atom bombardment-mass spectrometric analysis of the purified pFCC-1 product revealed that only one of the two oxygen atoms newly introduced into Pheide a in the course of the cleavage reaction is derived from molecular oxygen. Analysis of the fragment ions located the oxygen atom derived from molecular oxygen on the formyl group of pyrrole B. This finding demonstrates that the cleavage of Pheide a in vascular plants is catalyzed by a monooxygenase. Chlorophyll breakdown is therefore indicated to be mechanistically related in higher plants and in the green alga Chlorella protothecoides.

Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.


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