Elsevier

Tetrahedron Letters

Volume 34, Issue 47, 19 November 1993, Pages 7537-7540
Tetrahedron Letters

Two novel diketopiperazines isolated from the fungus Tolypocladium sp.

https://doi.org/10.1016/S0040-4039(00)60393-3Get rights and content

Abstract

Diketopiperazines, Sch 54794 and Sch 54796, have been isolated from a fungal fermentation. The structures of these compounds have been established based on spectroscopic data analysis. Sch 54794 exhibited inhibitory activity in the platelet activating factor (PAF) assay.

Two novel diketopiperazines, Sch 54794 and Sch 54796, have been isolated from a fungal fermentation and identified by spectral methods.

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Cited by (44)

  • Molecular Genetics of Secondary Chemistry in Metarhizium Fungi

    2016, Advances in Genetics
    Citation Excerpt :

    This NRPS is nested in a more conserved gene cluster found around M-NRPS27/M-PKS4 couple (Fig. 1-Y). Examples of fungal diketopiperazines among entomopathogenic species include SCH 54794, SCH 54796, and SCH 56396 from a Tolypocladium sp. (Chu et al., 1993; Chu, Truumees, Mierzwa, Patel, & Puar, 1997), bisdethiodi (methylthio)-1-demethylhyalodendrin and 1-demethylhyalodendrin tetrasulfide and the dimer vertihemiptellide from T. hemipterigena (Isaka, Palasarn, Rachtawee, Vimuttipong, & Kongsaeree, 2005; Nilanonta et al., 2003), and terezine D from Paecilomyces cinnamomeus and its teleomorph, T. luteorostrata (Isaka, Palasarn, Kocharin, & Hywel-Jones, 2007). Inasmuch as depsipeptides incorporating hydroxy acids by ester linkages can be biosynthesized by canonical NRPSs, it seems possible that the combination of an α-hydroxy acid and an amino acid to form a diketomorpholine ring as in metacytofilin (see Section 2.2.2) could be produced by genes that are predicted to produce diketopiperazines.

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