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Updated: Jun 8, 2025

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Biosynthesis of (-)-Vinigrol.

Run Xu1, Yi Zou1

  • 1College of Pharmaceutical Sciences, Southwest University, Chongqing, 400715, P. R. China.

Angewandte Chemie (International Ed. in English)
|November 3, 2024
PubMed
Summary
This summary is machine-generated.

Researchers identified the biosynthetic pathway for (-)-vinigrol, a complex molecule. A minimal gene cluster with a diterpene cyclase (VniA) and cytochrome P450 (VniB) enables its synthesis, revealing new fungal sources.

Keywords:
BiosynthesisCytochrome P450Diterpene CyclaseGenome MiningVinigrol-type skeleton

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Area of Science:

  • Natural Product Biosynthesis
  • Organic Chemistry
  • Mycology

Background:

  • (-)-Vinigrol is a structurally complex diterpenoid with significant synthetic challenges.
  • The natural biosynthetic pathway for (-)-vinigrol remained elusive, hindering its sustainable production.
  • Understanding biosynthesis is key to accessing rare and valuable natural products.

Purpose of the Study:

  • To elucidate the biosynthetic gene cluster responsible for (-)-vinigrol production.
  • To identify the enzymes involved in the key steps of (-)-vinigrol synthesis.
  • To discover novel fungal strains harboring the vinigrol biosynthetic pathway.

Main Methods:

  • Bioinformatic analysis and genome mining to identify candidate genes.
  • Heterologous expression of identified genes (VniA and VniB) in a suitable host.
  • Enzymatic assays to characterize the function of VniA (diterpene cyclase) and VniB (cytochrome P450).

Main Results:

  • A minimal gene cluster containing VniA and VniB was identified.
  • VniA was shown to cyclize geranylgeranyl diphosphate to form the vinigrol skeleton.
  • VniB was confirmed to catalyze iterative allylic C(sp3)-H oxidation, completing the synthesis.
  • Genome mining revealed new fungal species containing the vinigrol-type diterpene skeleton.

Conclusions:

  • The identified gene cluster and enzymes (VniA, VniB) provide a functional explanation for (-)-vinigrol biosynthesis.
  • This discovery enables the potential for biotechnological production of (-)-vinigrol.
  • The identification of new fungal sources expands the availability of vinigrol-type diterpenes.