Biosynthetic Gene-Based Secondary Metabolite Screening: A New Diterpene, Methyl Phomopsenonate, from the Fungus Phomopsis amygdali

The presence of the geranylgeranyl diphosphate synthase (GGS) gene is a common feature of gene clusters for diterpene biosynthesis. We demonstrated identification of a diterpene gene cluster using homology-based PCR of GGS genes and the subsequent genome walking in the fungus Phomopsis amygdali N2....

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2009-02, Vol.74 (4), p.1541-1548
Main Authors: Toyomasu, Tomonobu, Kaneko, Akane, Tokiwano, Tetsuo, Kanno, Yuya, Kanno, Yuri, Niida, Rie, Miura, Shigeyoshi, Nishioka, Taiki, Ikeda, Chiho, Mitsuhashi, Wataru, Dairi, Tohru, Kawano, Tomikazu, Oikawa, Hideaki, Kato, Nobuo, Sassa, Takeshi
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkyl and Aryl Transferases - chemistry
Alkyl and Aryl Transferases - metabolism
Ascomycota - enzymology
Ascomycota - genetics
Ascomycota - metabolism
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chemistry
Cloning, Molecular
Dimethylallyltranstransferase - metabolism
Diterpenes - analysis
Diterpenes - chemistry
Diterpenes - metabolism
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Genes, Fungal
Genome, Fungal - genetics
Magnetic Resonance Spectroscopy
Methods. Procedures. Technologies
Multigene Family
Organic chemistry
Preparations and properties
Protein Structure, Tertiary
Sequence Analysis, DNA
Terpenoids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The presence of the geranylgeranyl diphosphate synthase (GGS) gene is a common feature of gene clusters for diterpene biosynthesis. We demonstrated identification of a diterpene gene cluster using homology-based PCR of GGS genes and the subsequent genome walking in the fungus Phomopsis amygdali N2. Structure determination of a novel diterpene hydrocarbon phomopsene provided by enzymatic synthesis with the recombinant terpene synthase PaPS and screening of fungal broth extracts with reference to characteristic NMR signals of phomopsene allowed us to isolate a new diterpene, methyl phomopsenonate. The versatility of the gene-based screening of unidentified diterpenes is discussed in regard to fungal genomic data.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802319e