Sesquiterpenyl epoxy-cyclohexenoids (SECs) show impressive biological activities. However, the key pathways for SECs still remain unambiguous. Unexpectedly, 11 new SECs and derivatives with diverse oxidation patterns were isolated after the deletion of gene 274. A high accumulation of toluquinol and its new glycosides in mutant Δ276 and further isolation of the most crucial precursors farnesyl hydroquinone, farnesyl quinone, and three new derivatives from mutant Δ278 confirm that farnesylation at toluquinol is the key step for SECs.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b01846 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
The Multifaceted Gene 275 Embedded in the PKS-PTS Gene Cluster Was Involved in the Regulation of Arthrobotrisin Biosynthesis, TCA Cycle, and Septa Formation in Nematode-Trapping Fungus .
J Fungi (Basel)
November 2022
State Key Laboratory for Conservation and Utilization of Bio-Resources & Key Laboratory for Microbial Resources of the Ministry of Education, School of life Sciences, Yunnan University, Kunming 650091, China.
The predominant nematode-trapping fungus harbors a unique polyketide synthase-prenyltransferase (PKS-PTS) gene cluster responsible for the biosynthesis of sesquiterpenyl epoxy-cyclohexenoids (SECs) that are involved in the regulation of fungal growth, adhesive trap formation, antibacterial activity, and soil colonization. However, the function of one rare gene ( ()) embedded in the cluster has remained cryptic. Here, we constructed two mutants with the disruption of and the overexpression of , respectively, and compared their fungal growth, morphology, resistance to chemical stress, nematicidal activity, transcriptomic and metabolic profiles, and infrastructures, together with binding affinity analysis.
View Article and Find Full Text PDFAcetylation of Sesquiterpenyl Epoxy-Cyclohexenoids Regulates Fungal Growth, Stress Resistance, Endocytosis, and Pathogenicity of Nematode-Trapping Fungus via Metabolism and Transcription.
J Agric Food Chem
May 2022
State Key Laboratory for Conservation and Utilization of Bio-Resources & Key Laboratory for Microbial Resources of the Ministry of Education, School of Life Sciences, Yunnan University, Kunming 650091, People's Republic of China.
Sesquiterpenyl epoxy-cyclohexenoids (SECs) that depend on a polyketide synthase-terpenoid synthase (PKS-TPS) pathway are widely distributed in plant pathogenic fungi. However, the biosynthesis and function of the acetylated SECs still remained cryptic. Here, we identified that 00215 273 (273) was responsible for the acetylation of SECs in via the construction of Δ273, in which the acetylated SECs were absent and major antibacterial nonacetylated SECs accumulated.
View Article and Find Full Text PDFPolyketide Synthase-Terpenoid Synthase Hybrid Pathway Regulation of Trap Formation through Ammonia Metabolism Controls Soil Colonization of Predominant Nematode-Trapping Fungus.
J Agric Food Chem
April 2021
State Key Laboratory for Conservation and Utilization of Bio-Resources & Key Laboratory for Microbial Resources of the Ministry of Education, School of life Sciences, Yunnan University, Kunming, 650091, People's Republic of China.
Polyketide synthase-terpenoid synthase (PKS-TPS) hybrid pathways for biosynthesis of unique sesquiterpenyl epoxy-cyclohexenoids (SECs) have been found to be widely distributed in plant pathogenic fungi. However, the natural and ecological functions of these pathways and their metabolites still remain cryptic. In this study, the whole PKS-TPS hybrid pathway in the predominant nematode-trapping fungus was first proposed according to all the intermediates and their derivatives from all the mutants with a deficiency in each gene involved in SEC biosynthesis.
View Article and Find Full Text PDFNovel Polyketide-Terpenoid Hybrid Metabolites from a Potent Nematicidal Mutant Δ.
J Agric Food Chem
October 2020
State Key Laboratory for Conservation and Utilization of Bio-Resources & Key Laboratory for Microbial Resources of the Ministry of Education, School of Life Science, Yunnan University, Kunming 650091, People's Republic of China.
Here, we reported that detailed investigation on trace targeted metabolites from nematode-trapping fungus mutant with deletion of P450 gene led to isolation of 9 new polyketide-terpenoid hybrid derivatives, including four new glycosides of the key precursor farnesyl hydrotoluquinol () and, surprisingly, four new sesquiterpenyl epoxy-cyclohexenoids (SECs) analogues. Among them, two major target metabolites and displayed moderate nematode inhibitory ability. Moreover, the mutant lacking could form far more nematode-capturing traps within 6 h in contact with nematodes and show rapid potent nematicidal activity with killing 93.
View Article and Find Full Text PDFNovel Polyketide-Terpenoid Hybrid Metabolites and Increased Fungal Nematocidal Ability by Disruption of Genes and in Nematode-Trapping Fungus .
J Agric Food Chem
July 2020
State Key Laboratory for Conservation and Utilization of Bio-Resources and Key Laboratory for Microbial Resources of the Ministry of Education, School of life Sciences, Yunnan University, Kunming 650091, People's Republic of China.
Nematode-trapping fungus can produce a type of sesquiterpenyl epoxy-cyclohexenoid (SEC) metabolites that are regarded as characteristic chemtaxonomic markers. Here, we reported investigation on the functions of a putatively cupin-like family gene and a dehydrogenase gene by gene engineering, chemical metabolite profiling and phenotype analysis. Ten targeted metabolites were isolated from two mutants Δ and Δ and four novel metabolites including three polyketide-terpenoid (PK-TP) hybrid ones were characterized.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!