Illudin

The illudins are a family of sesquiterpenes with antitumor antibiotic properties produced by some mushrooms. In their isolated form, illudins show selective toxicity for myelocytic leukemia and other carcinoma cells.[1]

Skeletal formulae of isolated illudins

Illudins are highly toxic, with little apparent therapeutic value in their natural form. Illudins are thought to be responsible for the toxicity of various Omphalotus species such as O. olearius and O. illudens (Jack o' Lantern mushrooms), and O. nidiformis (Australian ghost fungus).

Active metabolites of illudins damage DNA via an unknown mechanism. In addition, genetic analysis suggests that the illudin-mediated DNA damage is ignored by global excision repair systems unless the lesions occur within stalled replication or transcription complexes.[2]

References

McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. (1992). "Structure-Activity Relationship of Illudins : Analogs with Improved Therapeutic Index". Journal of Organic Chemistry. 57 (25): 6876–6883. doi:10.1021/jo00051a037.
Jaspers, Nicolaas G.J; Raams, Anja; Kelner, Michael J; Ng, Jessica M.Y; Yamashita, Yukiko M; Takeda, Shiunichi; McMorris, Trevor C; Hoeijmakers, Jan H.J (2002). "Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways". DNA Repair. 1 (12): 1027–1038. doi:10.1016/S1568-7864(02)00166-0. hdl:1765/3203. ISSN 1568-7864. PMID 12531012.

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[1] McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. (1992). "Structure-Activity Relationship of Illudins : Analogs with Improved Therapeutic Index". Journal of Organic Chemistry. 57 (25): 6876–6883. doi:10.1021/jo00051a037.

[JaspersRaams2002-2] Jaspers, Nicolaas G.J; Raams, Anja; Kelner, Michael J; Ng, Jessica M.Y; Yamashita, Yukiko M; Takeda, Shiunichi; McMorris, Trevor C; Hoeijmakers, Jan H.J (2002). "Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways". DNA Repair. 1 (12): 1027–1038. doi:10.1016/S1568-7864(02)00166-0. hdl:1765/3203. ISSN 1568-7864. PMID 12531012.