The crystal structures of verrucarin E (4-acetyl-3-hydroxymethylpyrrole) and its 1/3 hydrate

Sheldrick, William S.; Borkenstein, A.; Engel, J.L.

doi:10.1107/s0567740878005282

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…Data were acquired on a Nonius Mach3 (Delft, Holland) single-crystal diffractometer (graphite-monochromated Mo KR radiation); the structure was solved and refined by standard procedures using the Shelx-97 package. The crystal structure found was identical to that previously reported (10).…”

Section: Single-crystal X-ray Analysis Of Verrucarin E (8)supporting

confidence: 86%

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Metabolites Inhibiting Germination of Orobanche ramosa Seeds Produced by Myrothecium verrucaria and Fusarium compactum

Andolfi

Boari

Evidente

et al. 2005

J. Agric. Food Chem.

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Myrothecium verrucaria and Fusarium compactum were isolated from diseased Orobanche ramosa plants collected in southern Italy to find potential biocontrol agents of this parasitic weed. Both fungi grown in liquid culture produced metabolites that inhibited the germination of O. ramosa seeds at 1-10 muM. Eight metabolites were isolated from M. verrucaria culture extracts. The main metabolite was identified as verrucarin E, a disubstituted pyrrole not belonging to the trichothecene group. Seven compounds were identified by spectroscopic methods as macrocyclic trichothecenes, namely, verrucarins A, B, M, and L acetate, roridin A, isotrichoverrin B, and trichoverrol B. The main metabolite produced by F. compactum was neosoloaniol monoacetate, a trichothecene. All the trichothecenes proved to be potent inhibitors of O. ramosa seed germination and possess strong zootoxic activity when assayed on Artemia salina brine shrimps. Verrucarin E is inactive on both seed germination and zootoxic assay.

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Section: Single-crystal X-ray Analysis Of Verrucarin E (8)supporting

confidence: 86%

“…The structure attributed to verrucarin E, which is a 2,4disubstituted pyrrole, was confirmed by X-ray analysis, recording crystal data identical to those previously described (10).…”

Section: Discussionsupporting

confidence: 73%