Ergosta-4,6,8(14), 22-tetraenon-(3) als inhaltsstoff des lärchenschwammes

Schulte, K. E.; Rüċker, G.; Fachmann, Hans-Jürgen

doi:10.1016/s0040-4039(00)75951-x

Cited by 26 publications

(16 citation statements)

References 2 publications

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“…As shown in Tables 1 and 2, the NMR data showed six characteristic ergosterol methyls. Actually, the data were similar to those of (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one, 12 with the only difference at the group of C-15. The HMBC correlations from H-15 (δ H 5.78) to C-1' (δ C 170.6) and from Me-2' (δ H 2.03) to C-1' (δ C 170.6) demonstrated the existence of acetoxy group at C-15 in 5.…”

Section: Resultssupporting

confidence: 71%

Six novel steroids from culture of basidiomycete Polyporus ellisii

Wang

Zhang

Liu

et al. 2012

Nat. Prod. Bioprospect.

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Investigation of the culture of basidiomycete Polyporus ellisii led to the isolation of a novel compound 3β,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (1) with a new 5/7/6/5 ring system of ergosterol skeleton. In addition, five new steroids, 5β,6β-epoxy-3β,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5β,6β-epoxy-3β,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 5α,6α-epoxy-3β,9α,15α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (4), 15α-acetoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), 15β-methoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), along with four known ergosterols (7-10), were obtained. All structures were elucidated based on 1D and 2D NMR spectral data. New compounds were evaluated for cytotoxicity against five human cancer cell lines, only compound 4 was found to exhibit a favorable cytotoxicity profile toward all tested tumor cell lines.

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Section: Resultssupporting

confidence: 71%

Six novel steroids from culture of basidiomycete Polyporus ellisii

Wang

Zhang

Liu

et al. 2012

Nat. Prod. Bioprospect.

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“…Pure 8 was prepared by column chromatography on aluminum oxide. Its ~H-NMR-spectrum proved to be identical with a sample isolated from Laricifomes officinatis ('Fungus laricis') according to Fachmann et al 23. Compound 8 is in fact responsible for the intense blue UVfluorescence of extracts of both fungi.…”

Section: Results and Discussion Isolation And Identification Of Fluorsupporting

confidence: 54%

Cortinarins inCortinarius speciosissimus? A critical revision

Matthies

Laatsch

1991

Experientia

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Fluorescent cyclic decapeptides, the so-called cortinarins, have been claimed to cause the toxicity of the deadly poisonous mushroom Cortinarius speciosissimus. As the structure elucidation described in the literature is doubtful in decisive parts, the proposed structures must be disputed. The present study demonstrates that the fluorescence is mainly due to ergosta-4,6,8(14),22-tetraen-3-one (8) and to photodecomposition products of the nephrotoxin orellanine (1). Moreover, we were not able to reproduce the isolation of fluorescent or any other cyclic peptides related to cortinarins from C. speciosissimus, by various methods.

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“…In comparison of the 1 H-and 13 C-NMR spectral data, the melting point, and the specific rotation of ZL-5 with those of ergosta-4,6,8(14),22-tetraen-3-one, which was isolated from some Basidiomycetes, Fomes officinalis, 20) Scleroderma polyrhizum, 21) Astraeus hygrometricus, 22) Ganoderma applanatum, and G. neo-japonicum, 23) ZL-5 was finally identified with ergosta-4,6,8(14),22-tetraen-3-one (5), as shown in Fig. 1 Table 2), indicating that ZL-6 is a 25-hydroxylated derivative of 1006 Vol.…”

mentioning

confidence: 99%

Six Immunosuppressive Features from an Ascomycete, Zopfiella ion gicaudata, Found in a Screening Study Monitored by Immunomodulatory Activity

Fujimoto

Nakamura

Okuyama

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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In a screening study on immunomodulatory fungal metabolites, three known anthraquinones, carviolin (roseo-purpurin) (1), 1-O-methylemodin (2), w w-hydroxyemodin (citreorosein) (4), and a new anthraquinone, w w- together with a known steroid, ergosta-4,6,8(14),22-tetraen-3-one (5) and a new steroid, 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one (6) were isolated from an Ascomycete, Zopfiella longicaudata, and found to have moderate immunosuppressive activities. The structure-activity relationships of these metabolites are discussed.

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Ergosta-4,6,8(14), 22-tetraenon-(3) als inhaltsstoff des lärchenschwammes

Cited by 26 publications

References 2 publications

Six novel steroids from culture of basidiomycete Polyporus ellisii

Six novel steroids from culture of basidiomycete Polyporus ellisii

Cortinarins inCortinarius speciosissimus? A critical revision

Six Immunosuppressive Features from an Ascomycete, Zopfiella ion gicaudata, Found in a Screening Study Monitored by Immunomodulatory Activity

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