ArticleMolecular biotechnology2019
The Biogenetic Origin of the Biologically Active Naematolin of Hypholoma Species Involves an Unusual Sesquiterpene Synthase.
Article in Molecular biotechnology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Systematic study ofIMA fungus · 2026Article
- Clade III Synthases Add Cyclic and Linear Terpenoids to the Psilocybe Metabolome.Chembiochem : a European journal of chemical biology · 2025Article
- Genome Mining of Fungal Unique Trichodiene Synthase-like Sesquiterpene Synthases.Journal of fungi (Basel, Switzerland) · 2024Article
- Molecular and Functional Analyses of Characterized Sesquiterpene Synthases in Mushroom-Forming Fungi.Journal of fungi (Basel, Switzerland) · 2023Article
- Genomic Based Analysis of the Biocontrol SpeciesJournal of fungi (Basel, Switzerland) · 2023Article
- Structural Understanding of Fungal Terpene Synthases for the Formation of Linear or Cyclic Terpene Products.ACS catalysis · 2023Article
- Biosynthesis of Sesquiterpenes in Basidiomycetes: A Review.Journal of fungi (Basel, Switzerland) · 2022Review
- In Vitro Assessment of Organic and Residual Fractions of Nematicidal Culture Filtrates from Thirteen TropicalJournal of fungi (Basel, Switzerland) · 2022Article
- Further Biochemical Profiling ofFrontiers in bioengineering and biotechnology · 2021Article
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Authors and funding
5 authors.
Funding
Abstract
Naematolin is a biologically active sesquiterpene produced by Hypholoma species. Low titres and complex structure constrain the exploitation of this secondary metabolite. Here, we de novo sequenced the H. fasciculare genome to identify a candidate biosynthetic gene cluster for production of naematolin. Using Aspergillus oryzae as a heterologous host for gene expression, the activity of several sesquiterpene synthases were investigated, highlighting one atypical sesquiterpene synthase apparently capable of catalysing the 1,11 and subsequent 2,10 ring closures, which primes the synthesis of the distinctive structure of caryophyllene derivatives. Co-expression of the cyclase with an FAD oxidase adjacent within the gene cluster generated four oxidised caryophyllene-based sesquiterpenes: 5β,6α,8β-trihydroxycariolan, 5β,8β-dihydroxycariolan along with two previously unknown caryophyllene derivatives 2 and 3. This represents the first steps towards heterologous production of such basidiomycete-derived caryophyllene-based sesquiterpenes, opening a venue for potential novel antimicrobials via combinatorial biosynthesis.
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