Schultriene and nigtetraene: two sesterterpenes characterized from pathogenetic fungi via genome mining approach.
Bifunctional terpene synthases
Cyclization mechanisms
Genome mining
Heterologous expression
Sesterterpene
Journal
Applied microbiology and biotechnology
ISSN: 1432-0614
Titre abrégé: Appl Microbiol Biotechnol
Pays: Germany
ID NLM: 8406612
Informations de publication
Date de publication:
Sep 2022
Sep 2022
Historique:
received:
19
05
2022
accepted:
06
08
2022
revised:
03
08
2022
pubmed:
31
8
2022
medline:
15
9
2022
entrez:
30
8
2022
Statut:
ppublish
Résumé
Fungal bifunctional terpene synthases (BFTSs) have been reported to contribute to the biosynthesis of a variety of di/sesterterpenes via different carbocation transportation pathways. Genome mining of new BFTSs from unique fungal resources will, theoretically, allow for the identification of new terpenes. In this study, we surveyed the distribution of BFTSs in our in-house collection of 430 pathogenetic fungi and preferred two BFTSs (CsSS and NnNS), long distance from previously characterized BFTSs and located in relatively independent branches, based on the established phylogenetic tree. The heterologous expression of the two BFTSs in Aspergillus oryzae and Saccharomyces cerevisiae led to the identification of two new sesterterpenes separately, 5/12/5 tricyclic type-A sesterterpene (schultriene, 1) for CsSS and 5/11 bicyclic type-B sesterterpene (nigtetraene, 2) for NnNS. In addition, to the best of our knowledge, 2 is the first 5/11 bicyclic type-B characterized sesterterpene to date. On the basis of this, the plausible cyclization mechanisms of 1 and 2 were proposed based on density functional theory calculations. These new enzymes and their corresponding terpenes suggest that the chemical spaces produced by BFTSs remain large and also provide important evidences for further protein engineering for new terpenes and for understanding of cyclization mechanism catalyzed by BFTSs. KEY POINTS: • Genome mining of two BFTSs yields two new sesterterpenoids correspondingly. • Identification of the first 5/11 ring system type-B product. • Parse out the rational cyclization mechanism of isolated sesterterpenoids.
Identifiants
pubmed: 36040489
doi: 10.1007/s00253-022-12125-4
pii: 10.1007/s00253-022-12125-4
doi:
Substances chimiques
Sesterterpenes
0
Terpenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6047-6057Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
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