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Identifying sesterterpenoids via feature-based molecular networking and small-scale fermentation.

Kangjie Lv1, Yuyang Duan1, Xiaoying Li1

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Feature-based molecular networking (FBMN) enabled the discovery of four new sesterterpenoids from low-yield fungal cultures. This approach accelerates natural product identification, showcasing FBMN

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Area of Science:

  • Natural Product Chemistry
  • Metabolomics
  • Synthetic Biology

Background:

  • Terpenoids possess diverse bioactivities valuable for pharmaceuticals.
  • Low-yield natural products are often overlooked in traditional analyses.
  • Feature-based molecular networking (FBMN) aids in identifying compounds with similar structures, including trace amounts.

Purpose of the Study:

  • To establish an efficient FBMN-based strategy for discovering and characterizing low-abundance natural products.
  • To identify new sesterterpenoids from Fusarium oxysporum.
  • To elucidate the biosynthetic pathway of novel sesterterpenoids.

Main Methods:

  • Identification of the FoFS-containing biosynthetic gene cluster in Fusarium oxysporum FO14005.
  • Application of a small-scale fermentation strategy combined with FBMN for compound discovery.
  • Characterization of new sesterterpenoids using tandem expression and substrate feeding experiments.

Main Results:

  • Four new sesterterpenoids, fusoxyordienoids A-D, with a unique 5/6/7/3/5 ring system were identified.
  • The cytochrome P450 monooxygenase FusB was found to be crucial for the functionalization of fusoxypene A and hydroxylation of fusoxyordienoid A.
  • The biosynthetic pathway involving FusB was elucidated.

Conclusions:

  • FBMN is a powerful tool for the rapid discovery and characterization of low-abundance natural products.
  • This study successfully identified novel sesterterpenoids and elucidated key steps in their biosynthesis.
  • The findings pave the way for exploring other complex natural products using similar strategies.