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. 1972 Dec;69(12):3713–3717. doi: 10.1073/pnas.69.12.3713

Synthesis of Plastoquinone Analogs and Inhibition of Photosynthetic and Mammalian Enzyme Systems*

Jan Bøler †, Ronald Pardini †, Hanna T Mustafa †, Karl Folkers †, Richard A Dilley ‡, Frederick L Crane ‡
PMCID: PMC389855  PMID: 4405029

Abstract

New 5-hydroxy- and 5-chloro-6-alkyl-1,4-benzoquinones with one or two methyl groups on the nucleus were synthesized as potential antimetabolites of plastoquinones for biological research on photosynthetic and mammalian enzyme systems; the primary emphasis was on photosynthesis.

2,3-Dimethyl-5-hydroxy-6-phytyl-1,4-benzoquinone completely inhibited in chloroplasts the water-dependent electron transport, but photosystem I was insensitive to this analog. The data are consistent with the interpretation that this analog inhibits electron transport in the chain prior to the site of electron donation from the ascorbate-dichlorophenolindophenol couple. Concentrations of 70 μM and 120 μM of this analog caused about 50 and 100% inhibition, respectively, of cyclic photophosphorylation.

2,3-Dimethyl-5-hydroxy-6-phytyl-1,4-benzoquinone is a new type of inhibitor of photosynthetic electron transport that specifically inhibits the rate-limiting step between photosystems I and II. Structurally related analogs caused inhibitions in the range of 50-100% in chloroplasts.

These analogs showed marginal inhibition in mitochondrial coenzyme Q10-oxidase systems from beef heart.

Keywords: chloroplasts, beef heart, coenzyme Q, electron transport

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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