Cercosporin, a novel photodynamic pigment isolated from Cercospora kikuchii.

Yamazaki, Sunao; Ōkubo, Akira; Akiyama, Yukio; Fuwa, Keiichirō

doi:10.1271/bbb1961.39.287

Cited by 67 publications

(49 citation statements)

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“…consistent with the mode of action for other photosensitizing compounds (Yamazaki et al, 1975;Daub, 1982a;Spikes, 1989). The cellular toxicity of elsinochromes was attenuated considerably when antioxidant compounds were added into the culture, implying the involvement of reactive oxygen species, particularly and/or 1 O 2 .…”

Section: Elsinochromes (Esc) Fromsupporting

confidence: 74%

Cellular toxicity of elsinochrome phytotoxins produced by the pathogenic fungus, Elsinoë fawcettii causing citrus scab

Liao

Chung

2007

New Phytologist

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Summary• Elsinochromes are the red/orange pigments produced by many Elsinoë fungal species and are structurally similar to the phytotoxin, cercosporin. Here, pigments were extracted from cultures of a citrus pathogen, Elsinoë fawcettii and tested for cellular toxicity.• On irradiation with light, elsinochromes rapidly killed suspension cultured citrus and tobacco cells. The toxicity was decreased by adding the singlet oxygen ( 1 O 2 ) quenchers (bixin (carotenoid carboxylic acid), DABCO (1, 4-diazabicyco octane), ascorbate or reduced glutathione). Application of elsinochromes onto rough lemon leaves resulted in necrotic lesions, whereas lesion development was inhibited by the addition of bixin, DABCO or ascorbate, but not α -tocopherol. Incubation of rough lemon leaf discs with elsinochromes in the light induced a steady increase of electrolyte leakage.• Compared with two photosensitizing compounds, hematoporphyrin and cercosporin, the accumulation of 1 O 2 induced by elsinochromes after irradiation was indicated by successful detection of the cholesterol oxidation product, 5 α -hydroperoxide. Addition of a potent quencher, β -carotene prevented 5 α -hydroperoxide production. Elsinochromes generated superoxide ions ( ), whereas accumulation of was blocked by addition of the superoxide dismutase, a scavenger of , but not the 1 O 2 -quencher, DABCO. Our study indicated that elsinochromes are functioning as photosensitizing compounds that produce 1 O 2 and , and exert toxicity to plant cells.

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Section: Elsinochromes (Esc) Fromsupporting

confidence: 74%

Cellular toxicity of elsinochrome phytotoxins produced by the pathogenic fungus, Elsinoë fawcettii causing citrus scab

Liao

Chung

2007

New Phytologist

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“…Its characterization and structure were reported independently by Lousberg and co-workers (12) and Yamazaki and Ogawa (20). Cercosporin is toxic to plants, mice, and bacteria (2,21). It has been shown to cause the peroxidation of plant lipids (3) and to result in major changes in the structure and composition ofplant cell membranes (4).…”

mentioning

confidence: 97%

Light-Induced Production of Singlet Oxygen and Superoxide by the Fungal Toxin, Cercosporin

Daub¹,

Hangarter²

1983

Plant Physiol.

144

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Cercosporin, a toxin produced by members of the fungal genus Cercospora, is a photosensitizing compound which rapidly kills plant cells in the light. We have found that cercosporin, when activated by light in the presence ofoxygen, is able to generate both singlet oxygen and superoxide ions. Cercosporin, when illuminated in the presence of 02, reacted with cholesterol to form the Sa-hydroperoxide of cholesterol which is only produced by reaction with singlet oxygen. Cercosporin, in the presence of light, 02, and a reducing substrate, was also able to reduce p-nitro blue tetrazolium chloride, a compound readily reduced by superoxide. Superoxide dismutase, a scavenger of superoxide, inhibited this reaction. Production of both singlet oxygen and superoxide by cercosporin must be considered when studying the possible mechanisms of resistance to cercosporin.

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“…Cercosporin is a photosensitizing compound (5,26), thus, it is not toxic to cells in the dark. In the presence of light, however, photosensitizers absorb the light energy to form electronically excited states and then transfer this energy to oxygen (8,18).…”

mentioning

confidence: 99%

Peroxidation of Tobacco Membrane Lipids by the Photosensitizing Toxin, Cercosporin

Daub

1982

Plant Physiol.

108

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Cercosporin, a nonspecific toxin from Cercospora species, is a photosensitizing compound which rapidly kills plant cells in the light. Cell death appears to be due to a cercosporin-mediated peroxidation of membrane lipids. Tobacco leaf discs treated with cercosporin showed a large increase in electrolyte leakage I to 2 minutes after irradiation with light. All tobacco protoplasts exposed to cercosporin in the light were damaged within 45 minutes. Chloroform:methanol extracts of toxin-treated suspension cultures gave positive reactions for lipid hydroperoxides in the thiobarbituric acid test. Cercosporin-treated leaf discs emitted high concentrations of ethane 12 to 24 hours after incubation in the light. Cercosporin also oxidized solutions of methyl linolenate as determined by the thiobarbituric acid assay and the emission of ethane. a-Tocopherol had an inhibitory effect on the cercosporin-mediated lipid peroxidation.Cercosporin [1,12-bis(2-hydroxypropyl)-2,1 1-dimethoxy-6,7-methylenedioxy-4,9-dihydroxyperylene-3, 10-quinoneI is a nonspecific phytotoxin produced by members ofthe genus Cercospora. It was first isolated in 1957 (9) from Cercospora kikuchii, a soybean pathogen, and has since been isolated from a large number of Cercospora species (1,2,7,11,14,23) and from Cercosporainfected plants (7,9,23). Its structure was determined independently by Lousberg et al. (10) and Yamazaki and Ogawa (25).Cercosporin is a photosensitizing compound (5, 26), thus, it is not toxic to cells in the dark. In the presence of light, however, photosensitizers absorb the light energy to form electronically excited states and then transfer this energy to oxygen (8,18). This results in the production of toxic oxygen species such as singlet oxygen or superoxide ions, which can damage living cells. Yamazaki et al. (26) showed that mice and bacteria were killed by cercosporin only when they were exposed to light, and that oxygen was involved in the process. Previous work in this laboratory (5) has determined that the action spectrum for the killing of tobacco cells by cercosporin is in close agreement with the absorption spectrum of cercosporin, and that the toxic effect of cercosporin can be inhibited by several quenchers of singlet oxygen.The toxic effects of photosensitizing compounds are well known (8, 18). One of the most common of these effects is damage to cellular membranes. Macri and Vianello (12) MATERIALS AND METHODSCercosporin. Cercosporin was isolated and purified from cultures of Cercospora nicotianae as previously described (5). Stock solutions were prepared in either acetone (for assays that involved cell cultures) or methanol (for assays that utilized leaf tissues). Stock solutions were stored at -20°C in the dark. The final concentration of acetone or methanol in control and cercosporintreated cultures did not exceed 1%.Host Material. Tissue discs for electrolyte leakage and ethane studies were cut from fully expanded leaves of Nicotiana tabacum cv 'Wisconsin 38' grown in the greenhouse. The N. tabacum cv 'W...

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Cercosporin, a novel photodynamic pigment isolated from Cercospora kikuchii.

Cited by 67 publications

References 1 publication

Cellular toxicity of elsinochrome phytotoxins produced by the pathogenic fungus, Elsinoë fawcettii causing citrus scab

Cellular toxicity of elsinochrome phytotoxins produced by the pathogenic fungus, Elsinoë fawcettii causing citrus scab

Light-Induced Production of Singlet Oxygen and Superoxide by the Fungal Toxin, Cercosporin

Peroxidation of Tobacco Membrane Lipids by the Photosensitizing Toxin, Cercosporin

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