title: Polyphenolic allelochemicals from the aquatic angiosperm Myriophyllum spicatum inhibit photosystem II.
abstract: Myriophyllum spicatum (Haloragaceae) is a highly competitive freshwater macrophyte that produces and releases algicidal and cyanobactericidal polyphenols. Among them, beta-1,2,3-tri-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucose (tellimagrandin II) is the major active substance and is an effective inhibitor of microalgal exoenzymes. However, this mode of action does not fully explain the strong allelopathic activity observed in bioassays. Lipophilic extracts of M. spicatum inhibit photosynthetic oxygen evolution of intact cyanobacteria and other photoautotrophs. Fractionation of the extract provided evidence for tellimagrandin II as the active compound. Separate measurements of photosystem I and II activity with spinach (Spinacia oleracea) thylakoid membranes indicated that the site of inhibition is located at photosystem II (PSII). In thermoluminescence measurements with thylakoid membranes and PSII-enriched membrane fragments M. spicatum extracts shifted the maximum temperature of the B-band (S(2)Q(B)(-) recombination) to higher temperatures. Purified tellimagrandin II in concentrations as low as 3 microM caused a comparable shift of the B-band. This demonstrates that the target site of this inhibitor is different from the Q(B)-binding site, a common target of commercial herbicides like 3-(3,4-dichlorophenyl)-1,1-dimethylurea. Measurements with electron paramagnetic resonance spectroscopy suggest a higher redox midpoint potential for the non-heme iron, located between the primary and the secondary quinone electron acceptors, Q(A) and Q(B). Thus, tellimagrandin II has at least two modes of action, inhibition of exoenzymes and inhibition of PSII. Multiple target sites are a common characteristic of many potent allelochemicals.
authors.affiliation: Limnologiesches Institut, Universität Konstanz, Freiburg, Germany.
authors.forename: Eva
authors.initials: E
authors.lastname: Leu
authors.forename: Anja
authors.initials: A
authors.lastname: Krieger-Liszkay
authors.forename: Charilaos
authors.initials: C
authors.lastname: Goussias
authors.forename: Elisabeth M
authors.initials: EM
authors.lastname: Gross
mesh_terms: D000458:Cyanobacteria / Q000187:drug effects / Q000502:physiology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D005419:Flavonoids; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D010100:Oxygen / Q000378:metabolism; D010636:Phenols / Q000378:metabolism / Q000494:pharmacology*; D010675:Pheromones / Q000378:metabolism / Q000494:pharmacology*; D010788:Photosynthesis / Q000187:drug effects; D045322:Photosynthetic Reaction Center Complex Proteins / Q000037:antagonists & inhibitors*; D045331:Photosystem I Protein Complex; D045332:Photosystem II Protein Complex; D011108:Polymers / Q000378:metabolism / Q000494:pharmacology*; D059808:Polyphenols; D018724:Spinacia oleracea / Q000187:drug effects / Q000502:physiology; D020524:Thylakoids / Q000187:drug effects
chemical_list: D004791:Enzyme Inhibitors; D005419:Flavonoids; D005960:Glucosides; D010636:Phenols; D010675:Pheromones; D045322:Photosynthetic Reaction Center Complex Proteins; D045331:Photosystem I Protein Complex; D045332:Photosystem II Protein Complex; D011108:Polymers; D059808:Polyphenols; C473299:tellimagrandin II; D005707:Gallic Acid; C087926:tellimagrandin I; D010100:Oxygen