The phytotoxic lichen metabolite, usnic acid, is a potent inhibitor of plant p‐hydroxyphenylpyruvate dioxygenase
Open Access
- 30 August 2000
- journal article
- Published by Wiley in FEBS Letters
- Vol. 480 (2-3) , 301-305
- https://doi.org/10.1016/s0014-5793(00)01907-4
Abstract
The lichen secondary metabolite usnic acid exists as a (−) and a (+) enantiomer, indicating a α or β projection of the methyl group at position 9b, respectively. (−)‐Usnic caused a dose‐dependent bleaching of the cotyledonary tissues associated with a decrease of both chlorophylls and carotenoids in treated plants whereas no bleaching was observed with the (+) enantiomer. (−)‐Usnic acid inhibited protophorphyrinogen oxidase activity (I 50=3 μM), but did not lead to protoporphyrin IX accumulation. Bleaching appears to be caused by irreversible inhibition of the enzyme 4‐hydroxyphenylpyruvate dioxygenase by (−)‐usnic acid (apparent IC50=50 nM).Keywords
This publication has 14 references indexed in Scilit:
- The structure-activity relationships of the triketone class of HPPD herbicides†Pesticide Science, 1998
- The Mode of Action of IsoxaflutolePesticide Biochemistry and Physiology, 1998
- Effects of Isoxazole Herbicides on Protoporphyrinogen Oxidase and Porphyrin PhysiologyJournal of Agricultural and Food Chemistry, 1997
- In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganismsAntimicrobial Agents and Chemotherapy, 1995
- Inhibition of 4-Hydroxyphenylpyruvate Dioxygenase by 2-(2-Nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dioneToxicology and Applied Pharmacology, 1995
- Physiological Basis for Differential Sensitivities of Plant Species to Protoporphyrinogen Oxidase-Inhibiting HerbicidesPlant Physiology, 1991
- Sequence of effects of acifluorfen on physiological and ultrastructural parameters in cucumber cotyledon discsPesticide Biochemistry and Physiology, 1985
- A method for the extraction of chlorophyll from leaf tissue without macerationCanadian Journal of Botany, 1979
- Relationship between inhibitor binding by chloroplasts and inhibition of photosynthetic electron transportBiochimica et Biophysica Acta (BBA) - Bioenergetics, 1977
- COPPER ENZYMES IN ISOLATED CHLOROPLASTS. POLYPHENOLOXIDASE IN BETA VULGARISPlant Physiology, 1949