Homozinniol, a New Phytotoxic Metabolite from <i>Alternaria solani</i>

Gamboa‐Angulo, Marcela; Alejos-González, Fátima; Peña‐Rodríguez, Luis M.

doi:10.1021/jf960134p

Cited by 10 publications

(8 citation statements)

References 24 publications

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“…Cultures of A. solani (IMI 129087) were maintained, grown, harvested (total volume: 115 L), extracted, and evaluated for phytotoxic activity on potato leaves (S. tuberosum L), following a procedure reported previously [3]. In this case, 11.5 g of the organic crude extract were suspended in a mixture of water/methanol (9 : 1) and the resulting suspension acidified to pH 2 (HCl 4 N).…”

Section: Methodsmentioning

confidence: 99%

“…Phytopathogenic fungi are well known for their production of toxic metabolites commonly known as phytotoxins; we have previously reported the identification of homozinniol, and 6-(3 0 ,3 0 -dimethylallyloxy)-4-methoxy-5-methyl-phthalide as metabolites from Alternaria solani, one of the most important phytopathogens known to cause early blight disease in potato and tomato [3].…”

Section: Introductionmentioning

confidence: 99%

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Two new zinniol-related phytotoxins fromAlternaria solani

Moreno-Escobar

Puc-Carrillo²,

Cáceres-Farfan³

et al. 2005

Natural Product Research

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Bioassay-guided purification of the organic crude extract of Alternaria solani resulted in the isolation of three metabolites responsible for causing necrosis on potato leaves. These phytotoxins were identified as 2-(2",3"-dimethyl-but-1-enyl)-zinniol (1), 8-zinniol methyl ether (2). and 8-zinniol methyl ether based on their spectroscopic data (IR, MS, 1H and 13CNMR). Metabolites 1 and 2 have been identified as new phytotoxins structurally related to zinniol (4). Additionally, 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methyl-phthalide and 8-zinniol-2-(phenyl)-ethyl ether (3) were also isolated during the purification process.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Two new zinniol-related phytotoxins fromAlternaria solani

Moreno-Escobar

Puc-Carrillo²,

Cáceres-Farfan³

et al. 2005

Natural Product Research

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“…16 Compound 4 has also been reported previously as a natural compound from A. porri and A. solani, which exhibited no particular inhibitory activity toward lettuce and stone-leek seedlings. [16][17][18] Compounds 6 and 8 displayed no significant phytotoxic activities using leaf-spot assay on marigold leaves. 16 Compound 5 was firstly isolated from A. cichorii which was inactive toward Russian knapweed and the lettuce shoot.…”

Section: Antifungal Activitiesmentioning

confidence: 98%

Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae

Yang

Zhang

et al. 2011

J Antibiot

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Three new phthalide derivatives (1-3) named 5-(3¢-methyl-2¢-butenyl)-2-hydroxy-3-methoxy-4-methylbenzoic acid (1), 5-(3¢-carboxyl-3¢-methyl-2E-allyloxy)-3-methoxy-4-methylphthalide (2) and 5-(3¢,3¢-dimethylallyloxy)-2-methoxycarbonyl-3-methoxy-4-methylbenzoic acid (3) together with six known phthalide derivatives named 5-(3¢,3¢-dimethylallyloxy)-3-methoxy-4-methylphthalide (4), zinnimidine (5), 5-(3¢,3¢-dimethylallyloxy)-3-methoxy-4-methylphthalide (6), 5-(3¢,3¢-dimethylallyloxy)-3-methoxy-4-methylphthalic acid (7), zinniol anhydride (8) and porriolide (9) were isolated from the liquid culture of the plant endophytic fungus Pestalotiopsis photiniae isolated from the Chinese Podocarpaceae plant Podocarpus macrophyllus. Their structures were elucidated by extensive spectroscopic analysis. Compounds 1-9 displayed significant antifungal activities against three plant pathogens.

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“…For example, Brian et al first reported that Alternaric acid is a biologically active product of the fungus Alternaria solani [ 2 , 3 ]. In addition, A. solani is capable of producing extracellular polysaccharides, carbohydrases, proteases, the new zinniol-related phytotoxins [ 4 , 5 ], and other secondary metabolites during infection [ 6 , 7 ]. It has been documented that sporulation of A. solani depends upon many factors such as mycelial wounding, temperature, visible light, water treatment, ozone and ultraviolet [ 8 – 11 ].…”

Section: Introductionmentioning

confidence: 99%

Genome sequence of the potato pathogenic fungus Alternaria solani HWC-168 reveals clues for its conidiation and virulence

Zhang

Haddadi

et al. 2018

BMC Microbiol

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BackgroundAlternaria solani is a known air-born deuteromycete fungus with a polycyclic life cycle and is the causal agent of early blight that causes significant yield losses of potato worldwide. However, the molecular mechanisms underlying the conidiation and pathogenicity remain largely unknown.ResultsWe produced a high-quality genome assembly of A. solani HWC-168 that was isolated from a major potato-producing region of Northern China, which facilitated a comprehensive gene annotation, the accurate prediction of genes encoding secreted proteins and identification of conidiation-related genes. The assembled genome of A. solani HWC-168 has a genome size 32.8 Mb and encodes 10,358 predicted genes that are highly similar with related Alternaria species including Alternaria arborescens and Alternaria brassicicola. We identified conidiation-related genes in the genome of A. solani HWC-168 by searching for sporulation-related homologues identified from Aspergillus nidulans. A total of 975 secreted protein-encoding genes, which might act as virulence factors, were identified in the genome of A. solani HWC-168. The predicted secretome of A. solani HWC-168 possesses 261 carbohydrate-active enzymes (CAZy), 119 proteins containing RxLx[EDQ] motif and 27 secreted proteins unique to A. solani.ConclusionsOur findings will facilitate the identification of conidiation- and virulence-related genes in the genome of A. solani. This will permit new insights into understanding the molecular mechanisms underlying the A. solani-potato pathosystem and will add value to the global fungal genome database.Electronic supplementary materialThe online version of this article (10.1186/s12866-018-1324-3) contains supplementary material, which is available to authorized users.

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Homozinniol, a New Phytotoxic Metabolite from Alternaria solani

Cited by 10 publications

References 24 publications

Two new zinniol-related phytotoxins fromAlternaria solani

Two new zinniol-related phytotoxins fromAlternaria solani

Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae

Genome sequence of the potato pathogenic fungus Alternaria solani HWC-168 reveals clues for its conidiation and virulence

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