Die Konstitution von Diacetoxyscirpenol

Sigg, H. P.; Mauli, R.; Flury, E.; Hauser, Daniel

doi:10.1002/hlca.19650480434

Cited by 81 publications

(41 citation statements)

References 20 publications

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“…Also, the three trichoverroids (type II compounds) were all weak in their relative activity and the same was true for the epoxide containing roridoid 4, a roridoid possessing both the 12,13-epoxide and a 1,3-dioxalane ring embedded in the macrocycle. Although anguidine (17) 38 was intermediate in its relative activity, it was unselective against both murine and human tumors. Alternatively, compounds in the most active group [7b > 7a, ≈ 6, 1b > 1a > 8] were all 12,13-epoxy containing macrocyclic trichothecenes as either roridiods (III) or verrucaroids (IV).…”

Section: Resultsmentioning

confidence: 99%

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

et al. 2003

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Saltwater culture of Myrothecium verrucaria, separated from a Spongia sp. collected in Hawaii, was a source of three new trichothecenes, 3-hydroxyroridin E (1a), 13′-acetyltrichoverrin B (2), and miophytocen C (3) and nine known related compounds (1b, 4, 5, 6, 7a, 7b, 8, 9a, and 9b). The stereostructures of the new compounds were established on the basis of 1D and 2D NMR spectral analyses and a chemical transformation. At the same time, the stereostructures of known compounds, 1b, 4, and 5 reported previously were also elucidated. All the compounds except 3 showed significant cytotoxicity against murine and human tumor cell lines. Moreover, the structure-activity relationships (SARs) were established from the results of the bioassay data.

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Section: Resultsmentioning

confidence: 99%

Structures and Cytotoxic Properties of Trichoverroids and Their Macrolide Analogues Produced by Saltwater Culture of Myrothecium verrucaria

et al. 2003

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“…The TAS and STO were prepared according to the procedures given by Richardson and Hamilton (1987a), the 4,15-DAS according to Richardson and Hamilton (1987b), the 4-MAS and 15-MAS according to Sigg et al (1965). The 3,4-DAS, 3,15-DAS, and 3-MAS were produced by the respective acetylation of 4-MAS, 15-MAS, and STO (100 mg in 2 mL of pyridine plus .2 mL of acetylchloride at 60 C for 3 min; details to be published elsewhere).…”

Section: Chemicalsmentioning

confidence: 99%

Comparative Toxicity of Scirpentriol and Its Acetylated Derivatives ,

Richardson

Hamilton

1990

Poultry Science

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Scirpentriol (STO) and its seven acetylated derivatives, 3-, 4- and 15-monoacetoxyscirpenol (MAS), 3,4-, 3,15-, and 4,15-diacetoxyscirpenol (DAS), and 3,4,15-triacetoxyscirpenol (TAS) were compared for their acute oral lethality in broiler chicks, lethality in brine shrimp, and dermal toxicity in guinea pigs. Of the eight toxins, 4,15-DAS was the most toxic in the three assays, 3-MAS was the least toxic in brine shrimp and dermal assays, and 3,4-DAS was the least toxic in the chick assay. There was a difference of about a 100-fold and 20-fold, respectively, between 4,15-DAS and 3-MAS in dermal toxicity and brine-shrimp toxicity, as well as a difference of more than 16-fold between 4,15-DAS and 3,4-DAS in chick toxicity. In general, a free hydroxy group at the 3-position was a primary determinant of toxicity. Toxicity in the scirpenol family did not follow precisely the pattern reported earlier for the T-2 toxin family of trichothecene toxins, in which a decrease in the number of acyl groups was accompanied by a decrease in toxicity. At necropsy, the predominant sign in chicks was petechial hemorrhaging, primarily in the gastrointestinal tract and in the vascular beds of the beaks and the toe nails. The 4,15-DAS and 15-MAS were about 3 times more toxic in chicks than aflatoxin. All members of the scirpenol family of trichothecene mycotoxins appeared sufficiently toxic to warrant attention whenever field outbreaks occur. Apparently, brine shrimp and dermal assays are successful predictors of chick lethality by the more toxic trichothecenes and are less suitable for predicting the activity of the less toxic trichothecenes.

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“…5 The in vivo mouse tumor inhibition test was conducted according to the protocols established by the National Cancer Institute.6) The tissue culture tests were performed following published procedures.7)…”

Section: Sirmentioning

confidence: 99%