Alkaline Hydrolysis of Trichothecin

Freeman, G. G.; Gill, J. E.

doi:10.1038/166698b0

Cited by 20 publications

(7 citation statements)

References 3 publications

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“…The title compound is the alcohol of an antifungal antibiotic, crotocin (I), isolated from a Cephalosporium strain (Ghiz, Scheiber, Gyimesi, Horv~ith, Steczek, Szentirmai & Bohus, 1959). Molecular weights of both crotocin and crotocol were corroborated by crystal data (K~ilm~in, 1963)and they were shown later (Gyimesi, 1965) to have been isomers of the antibiotic trichotecin and its alcohol trichotecholone (IIa) (Freeman & Gill, 1950;Godtfredsen & Vangedal, 1964). Chemical and n.m.r, studies (Gyimesi & Melera, 1967) showed crotocol to be a diepoxide alcohol.…”

Section: C(7)--c(6)-c(11)mentioning

confidence: 71%

Crotocol, a sesquiterpenoid alcohol

Czugler¹,

Kàlmán²

1975

Acta Crystallogr Sect B

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Section: C(7)--c(6)-c(11)mentioning

confidence: 71%

Crotocol, a sesquiterpenoid alcohol

Czugler¹,

Kàlmán²

1975

Acta Crystallogr Sect B

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“…The following synthetic esters related to trichotheein were prepared : acetyltrichothecolone, acetyldihydrotrichothecolone, crotonyltrichothecolone and butyryltrichothecolone ( Table 3). Hydrolysis of trichothecin with boiling aqueous sodium hydroxide gave isocrotonic acid and a ketonic alcohol, isotrichothecolone, isomeric with trichothecolone (Freeman & Gill, 1950). The corresponding acetyl ester, acetyl isotrichothecolone, was prepared and its biological properties examined.…”

Section: G G Freemanmentioning

confidence: 99%

“…This toxicity does not appear to be associated with that of trichothecin since the medium upon which the mould was grown was free from the toxin. Trichothecin (C,,H,,O,) is the isocrotonyl ester of the ketonic alcohol trichothecolone ( C,,H,oO, ;Freeman & Gill, 1950). The following synthetic esters related to trichotheein were prepared : acetyltrichothecolone, acetyldihydrotrichothecolone, crotonyltrichothecolone and butyryltrichothecolone ( Table 3).…”

Section: G G Freemanmentioning

confidence: 99%

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Further Biological Properties of Trichothecin, an Antifungal Substance from Trichothecium roseum Link, and its Derivatives

Freeman¹

1955

Journal of General Microbiology

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SUMMARY: Production of trichothecin in submerged aerated cultures of a strain of Trichothecium roseum is described. The antibiotic is active in vitro against certain fungi pathogenic in man, including the causative organisms of some generalized infections and several of the common skin pathogens. I n general, the sensitive pathogens were inhibited a t trichothecin concentrations of 16 p.p.m. or less and the antifungal activity was not influenced by the presence of blood serum (5 yo) in the medium. Trichothecin is toxic to laboratory animals; single doses at the rate of 250 mg./kg. intravenously in mice and subcutaneously in rats resulted in death. The antibiotic also produced a reaction when brought into contact with the skin.The antifungal activity of a series of esters related to trichothecin was of the same order as that of the parent substance. With the exception of esters in which the ethylenic double bond of trichothecolone had been saturated, none of the known derivatives or fission products exhibits more than a very slight activity. The presence of a large excess of p-indolylacetic acid did not affect the antifungal activity of trichothecin. This suggests that the effect of the latter in inhibiting plant growth regulating activity of /3-indolylacetic acid and related substances is not due to molecular combination of the two substances.

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“…The number of lesions was often much decreased in bean leaves which showed little or no injury. In addition t o tests with metabolic products of T. roseum, some were also made with derivatives of trichothecin (Freeman & Gill, 1950). The results of one series of tests are given in Table 1.…”

Section: Inhibition By Substances With Small Molecular Weightsmentioning

confidence: 99%

The Nature and Behaviour of Inhibitors of Plant Viruses produced by Trichothecium roseum Link

Bawden

Freeman

1952

Journal of General Microbiology

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The extent to which infection is inhibited depends on the species of the host plant but not on the identity of the virus. Trichothecin, like ribonuclease, is relatively more effective with beans than with Nicotiana glutinosa, whereas the polysaccharide and two derivatives of trichothecin (trichothecolone and acetyltrichothecolone) affect N. glutinosa more than beans. Trichothecin inhibits infection when sprayed over leaves a day after they have been inoculated with viruses, but is ineffective when applied 2 days before. The polysaccharide inhibits when sprayed over leaves before inoculation but not after. It is suggested that inhibitors act by temporarily altering the metabolism of leaf cells so that introduced virus particles cannot multiply and are inactivated.

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Alkaline Hydrolysis of Trichothecin

Cited by 20 publications

References 3 publications

Crotocol, a sesquiterpenoid alcohol

Crotocol, a sesquiterpenoid alcohol

Further Biological Properties of Trichothecin, an Antifungal Substance from Trichothecium roseum Link, and its Derivatives

The Nature and Behaviour of Inhibitors of Plant Viruses produced by Trichothecium roseum Link

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