Trichothecinols A, B and C, potent anti-tumor promoting sesquiterpenoids from the fungus Trichothecium roseum

Iida, Akira; Konishi, Kenichi; Kubo, Hiromu; Tomioka, Kiyoshi; Tokuda, Harukuni; Nishino, Hoyoku

doi:10.1016/s0040-4039(96)02187-9

Cited by 28 publications

(18 citation statements)

References 9 publications

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“…Five other known compounds, guangomide A (5), 3 roseotoxin S, 18 crotocin, 17,19 trichothecinol B, 20 and trichothecin, 4,19 were isolated and elucidated; in all cases, the structural data were in agreement with the literature. The identification of the cyclodepsipeptide 5 was of particular interest, as it was described initially from an unidentified fungal strain isolated from an Ianthella sponge.…”

supporting

confidence: 78%

Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320)

et al. 2011

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Two new cyclodepsipeptides (1 and 2), two new sesquiterpenoids (3 and 4), and the known compounds guangomide A (5), roseotoxin S, and three simple trichothecenes were isolated from the cytotoxic organic extract of a terrestrial filamentous fungus, Trichothecium sp. The structures were determined using NMR spectroscopy and mass spectrometry. Absolute configurations of the cyclodepsipeptides were established by employing chiral HPLC, while the relative configurations of 3 and 4 were determined via NOESY data. The isolation of guangomide A was of particular interest, since it was reported previously from a marine derived fungus.

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supporting

confidence: 78%

Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320)

et al. 2011

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“…The carbon chemical shift (d C = 19.0) of the allylic methyl (C12 0 ), was used to assign the E-arrangment of the trisubstituted double bond as supported by NOESY. Final assessment of this stereochemistry was made by reference to coupling constant data of trichothecinols A-C (Iida et al, 1996) , namely, the coupling constants to H3b and H3a show a diagnostic pattern (H3b: 3 J 2,3b * 5.0 Hz, 3 J 3b,4 * 3.5 Hz, H3a: 3 J 2,3a *0 Hz, 3 J 3a,4 * 7.8 Hz). Therefore, the chiral centers on the trichothecene ring can be assigned as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Two novel trichothecenes from Myrothecium roridum

2007

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Two new trichothecenes, Roridin P and Isororidin P, and two known trichothecenes, Verrucarin A and Verrucarin J, were isolated from liquid cultures of Myrothecium roridum Tale ex Fr. The stereo-structures of Roridin P and Isororidin P were established on the basis of one-and two-dimensional nuclear magnetic resonance (NMR) spectral analyses. Roridin P and Isororidin P induced morphological changes in Pyricularia oryzae, with a minimum concentration (MMCC) value of 6.2 ± 1.1 mmol/L and 7.9 ± 1.5 mmol/L.

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“…Therefore, applying this trend to the data of 1a and 1b further confirms that the hydroxyl groups in each are in an R orientation. Since the absolute stereochemistry of 10-12 has also been reported, 31 by analogy to their common biosynthetic origin, the seven chiral centers on the trichothecene ring of 1a and 1b can be assigned as 2R, 3S, 4S, 5S, 6R, 11R, 12S.…”

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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Trichothecinols A, B and C, potent anti-tumor promoting sesquiterpenoids from the fungus Trichothecium roseum

Cited by 28 publications

References 9 publications

Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320)

Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320)

Two novel trichothecenes from Myrothecium roridum

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

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