1988
DOI: 10.1016/0014-5793(88)80743-9
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Anthraquinone inhibitors of photosystem II electron transport

Abstract: Various substituted 9,10-anthraquinones were tested for their inhibitory activity on photosystem II electron transport. Maximal inhibitory activity was achieved if the positions adjacent to one of the quinone carbonyl groups were unsubstituted or substituted by hydroxyl groups only. The best anthraquinone type inhibitor found so far was 2,3,4-trichloro-lhydroxy-anthraquinone with a pl,, value of 7.75. This is well comparable to the most powerful known photosystem II

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Cited by 33 publications
(13 citation statements)
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“…Juglone's mode of toxic action could involve mixed mechanisms including electrophilic reactivity of its quinoidal and phenolic functionalities (Table 1) toward cellular nucleophiles (e.g., alcohol, thiol, and amino groups) and an ability to undergo oxidation–reduction cycles between oxidized quinones, partially reduced semiquinones, and fully reduced phenols (O'Brien, 1991; Rath et al, 1996). The redox‐active nature of juglone's functional groups provides properties known to disrupt physiologically important electron transfer chains in plants (Oettmeier et al, 1988).…”
Section: Molecular Properties Of Juglone (5‐hydroxy‐14‐naphthoquinone)mentioning
confidence: 99%
“…Juglone's mode of toxic action could involve mixed mechanisms including electrophilic reactivity of its quinoidal and phenolic functionalities (Table 1) toward cellular nucleophiles (e.g., alcohol, thiol, and amino groups) and an ability to undergo oxidation–reduction cycles between oxidized quinones, partially reduced semiquinones, and fully reduced phenols (O'Brien, 1991; Rath et al, 1996). The redox‐active nature of juglone's functional groups provides properties known to disrupt physiologically important electron transfer chains in plants (Oettmeier et al, 1988).…”
Section: Molecular Properties Of Juglone (5‐hydroxy‐14‐naphthoquinone)mentioning
confidence: 99%
“…Polycyclic aromatic hydrocarbons (PAHs) are a class of ubiquitous environmental contaminants for which toxicity is substantially enhanced by absorption of light, especially ultraviolet (UV) radiation (Oris and Giesy, 1985;Huang et al, 1993;Ankley et al, 1994;Arfsten et al, 1996;McConkey et al, 1997). The acute toxic mode of action of PAHs has generally been attributed to light-mediated production of destructive singlet oxygen, peroxides, and hydroxyl radicals in the membranes of the organism following uptake into the tissue.…”
Section: Introductionmentioning
confidence: 99%
“…For instance, 2,5-dibromo-3-methyl-6-isopropyl-p-benzoquinone (DBMIB), a plastoquinone analog, is a classical inhibitor of the cytochrome b 6 /f complex in the photosynthetic electron transport chain (Izawa, 1977;Trebst, 1980). But also herbicide-like actions on the Q B site of PSII by 1,4 benzoquinones, -naphthoquinones and anthraquinones have been described (Oettmeier et al, 1987(Oettmeier et al, , 1988. However, at relatively high-concentrations (10-20 lM), DBMIB acts as a PSII electron acceptor (Izawa et al, 1973).…”
Section: Discussionmentioning
confidence: 98%