Immunosuppressive polyketides from mantis-associated Daldinia eschscholzii

Ying L. Zhang, Jie Zhang, Nan Jiang, Yan H. Lu, Lu Wang, Su H. Xu, Wei Wang, Gao F. Zhang, Qiang Xu, Hui M. Ge, Jing Ma, Yong C. Song, Ren X. Tan

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

Polyketides with unknown architectures are highly desired for the discovery of new drugs and agrochemicals. Here, the mantis-associated Daldinia eschscholzii, a fungus known to produce immunosuppressants dalesconols A and B, was found to simultaneously generate four novel skeletons capable of shaping the unusual chemistry of the fungal polyketides, of which seven were structurally unique and substantially immunosuppressive. In particular, the scaled-up fermentation of the microbe enabled the structural characterization of minor or "transitional" intermediate polyketides that allowed the reasonable recognition of the four biosynthetic pathways initiated by condensations of four, five, six and eight acetate units, respectively. Furthermore, the decarbonylation reaction of triketone, as in the case of daeschol A, was described for the first time, in addition to the structural correction of sporothrin C and nodulone. The work provided a set of novel immunosuppressive molecules that are of significance to drug discovery.

Original languageEnglish (US)
Pages (from-to)5931-5940
Number of pages10
JournalJournal of the American Chemical Society
Volume133
Issue number15
DOIs
StatePublished - Apr 20 2011
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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