Synthetic Studies of Salicylaldehyde-type Phytotoxins Isolated from Rice Blast Fungus

Kiyota, Hiromasa

doi:10.5059/yukigoseikyokaishi.77.173

Cited by 2 publications

(1 citation statement)

References 27 publications

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“…[30][31][32][33][34][35] Through synthetic studies, it was clarified that the blast fungus produces optically active toxins such as pyriculol and pyricuol under shaking culture conditions, while pyriculariol and dihydropyriculariol resulting from aeration and agitation culture are racemic. 36) Pseudomonas syringae pv. tabaci, the causative fungus of tobacco wildfire disease, produces tabtoxin which is converted into tabtoxinine-β-lactam by a plant peptidase, leading to inhibition of glutamine synthetase and the non-selective death of plants ( Fig.…”

Section: Organic Compounds Derived From Microorganismsmentioning

confidence: 99%

Synthetic studies of biologically active natural products contributing to pesticide development

Kiyota

2020

J. Pestic. Sci.

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Natural product research, including total synthesis, is becoming increasingly important for the discovery of pesticide seeds and leads. Synthetic studies of biologically active compounds such as antibiotics (enacyloxins, polynactin, pamamycins, spirofungin A and B, glutarimides and antimycins), phytopathogenic toxins (pyricuol, pyriculariol, tabtoxinine-β-lactam, gigantenone, phomenone and phaseolinone), marine derived products (pteroenone, β-D-Asp-Gly, didemniselinolipid B, cortistatin A, sanctolide A and gizzerosine), POPs (dieldrin, endosulfan, HCB), plant hormones (abscisic acid and jasmonic acid), insect pheromones (endo-brevicomin etc.), especially using a variety of biotransformation are described.

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Section: Organic Compounds Derived From Microorganismsmentioning

confidence: 99%

Synthetic studies of biologically active natural products contributing to pesticide development

Kiyota

2020

J. Pestic. Sci.

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Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates

Nagashima

Sasaki

Hiraoka

et al. 2021

Bioscience, Biotechnology, and Biochemistry

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Synthesis of assumed natural (12R,13S)-enantiomers of pyriculariol (1) and dihydropyriculariol (2), phytotoxins isolated from rice blast disease fungus, Pyricularia oryzae, was achieved using Wittig reaction or microwave-assisted Stille coupling reaction as the key step. The synthesis revealed that the natural 1 and 2 are racemates. Foliar application test on a rice leaf indicated that both the salicylaldehyde core and side chain were necessary for phytotoxic activity. The fungus is found to produce optically active phytotoxins when incubated with rotary shaker, but racemic ones when cultured using an aerated jar fermenter.

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Synthetic Studies of Salicylaldehyde-type Phytotoxins Isolated from Rice Blast Fungus

Cited by 2 publications

References 27 publications

Synthetic studies of biologically active natural products contributing to pesticide development

Synthetic studies of biologically active natural products contributing to pesticide development

Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates

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