Biosynthetic Machinery of 6-Hydroxymellein Derivatives Leading to Cyclohelminthols and Palmaenones

Takahiro Ugai, Atsushi Minami, Shizuya Tanaka, Taro Ozaki, Chengwei Liu, Hideyuki Shigemori, Masaru Hashimoto, Hideaki Oikawa

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)


Oxygenated cyclopentene systems are unique structural motifs found in fungal polyketides such as terrein, cyclohelminthols, and palmaenones. Here we report the identification of the biosynthetic gene clusters for cyclohelminthols and palmaenones and the functional characterization of the polyketide synthases and halogenases involved in the construction of 6-hydroxymellein derivatives. Heterologous expression in Aspergillus oryzae demonstrated that 6-hydroxymellein is a common biosynthetic intermediate and that chlorination occurs in the early stages of its products’ biosynthesis. This was further confirmed by in vitro enzymatic reactions conducted in the presence of recombinant proteins. Plausible means of biogenesis of fungal polyketides from 6-hydroxymellein derivatives, additionally supported by the reported labeling patterns of terrein and structurally related fungal polyketides, are also discussed. This study sets the stage for elucidation of the biosynthetic machinery of fungal polyketides of this type.

Original languageEnglish
Pages (from-to)360-367
Number of pages8
Issue number3
Publication statusPublished - 2020 Feb 3
Externally publishedYes


  • 6-hydroxymellein
  • Aspergillus oryzae
  • biosynthesis
  • cyclohelminthols
  • halogenases
  • polyketides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry


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