InChI=1S/C12H15NO4/c1-6(2)4-8(14)12-16-9-5-7(3)13-11(15)10(9)17-12/h5-6,12H,4H2,1-3H3,(H,13,15) |
VALUPXXLHSBISM-UHFFFAOYSA-N |
C1(OC2=C(O1)C(=O)NC(C)=C2)C(=O)CC(C)C |
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Phoma sp.
(NCBI:txid1707701)
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See:
PubMed
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Calcarisporium arbuscula
(NCBI:txid240499)
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of strain
NRRL 3705
See:
PubMed
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Aspergillus terreus NIH2624
(NCBI:txid341663)
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See:
PubMed
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Aspergillus flavipes
(NCBI:txid41900)
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See:
DOI
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Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
mycotoxin
Poisonous substance produced by fungi.
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antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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View more via ChEBI Ontology
(2R)-6-methyl-2-(3-methylbutanoyl)-5H-[1,3]dioxolo[4,5-c]pyridin-4-one
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(±)-isoflavipucine
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SUBMITTER
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Cheng JT, Cao F, Chen XA, Li YQ, Mao XM (2020) Genomic and transcriptomic survey of an endophytic fungus Calcarisporium arbuscula NRRL 3705 and potential overview of its secondary metabolites. BMC genomics 21, 424 (Source: SUBMITTER) [PubMed:32580753] [show Abstract]
BackgroundSecondary metabolites as natural products from endophytic fungi are important sources of pharmaceuticals. However, there is currently little understanding of endophytic fungi at the omics levels about their potential in secondary metabolites. Calcarisporium arbuscula, an endophytic fungus from the fruit bodies of Russulaceae, produces a variety of secondary metabolites with anti-cancer, anti-nematode and antibiotic activities. A comprehensive survey of the genome and transcriptome of this endophytic fungus will help to understand its capacity to biosynthesize secondary metabolites and will lay the foundation for the development of this precious resource.ResultsIn this study, we reported the high-quality genome sequence of C. arbuscula NRRL 3705 based on Single Molecule Real-Time sequencing technology. The genome of this fungus is over 45 Mb in size, larger than other typical filamentous fungi, and comprises 10,001 predicted genes, encoding at least 762 secretory-proteins, 386 carbohydrate-active enzymes and 177 P450 enzymes. 398 virulence factors and 228 genes related to pathogen-host interactions were also predicted in this fungus. Moreover, 65 secondary metabolite biosynthetic gene clusters were revealed, including the gene cluster for the mycotoxin aurovertins. In addition, several gene clusters were predicted to produce mycotoxins, including aflatoxin, alternariol, destruxin, citrinin and isoflavipucine. Notably, two independent gene clusters were shown that are potentially involved in the biosynthesis of alternariol. Furthermore, RNA-Seq assays showed that only expression of the aurovertin gene cluster is much stronger than expression of the housekeeping genes under laboratory conditions, consistent with the observation that aurovertins are the predominant metabolites. Gene expression of the remaining 64 gene clusters for compound backbone biosynthesis was all lower than expression of the housekeeping genes, which partially explained poor production of other secondary metabolites in this fungus.ConclusionsOur omics data, along with bioinformatics analysis, indicated that C. arbuscula NRRL 3705 contains a large number of biosynthetic gene clusters and has a huge potential to produce a profound number of secondary metabolites. This work also provides the basis for development of endophytic fungi as a new resource of natural products with promising biological activities. | Mizutani S, Komori K, Taniguchi T, Monde K, Kuramochi K, Tsubaki K (2016) A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine. Angewandte Chemie (International ed. in English) 55, 9553-9556 (Source: SUBMITTER) [PubMed:27376480] [show Abstract] A biomimetic synthesis of naturally occurring lactams rubrobramide, flavipucine, and isoflavipucine is described. The key step is a regioselective Darzens reaction between isobutyl glyoxal and an α-bromo-β-ketoamide. The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an α,β-epoxy-γ-lactam. Furthermore, the absolute configuration of naturally occurring (+)-rubrobramide was determined by vibrational circular dichroism. (±)-Flavipucine and (±)-isoflavipucine were synthesized from an epoxyimide, which was prepared by reaction of isobutyl glyoxal with a protected α-bromo-β-ketoamide. Deprotection of the epoxyimide and formation of the pyridone ring gave (±)-flavipucine, which was converted into (±)-isoflavipucine by thermal isomerization. | Gressler M, Zaehle C, Scherlach K, Hertweck C, Brock M (2011) Multifactorial induction of an orphan PKS-NRPS gene cluster in Aspergillus terreus. Chemistry & biology 18, 198-209 (Source: SUBMITTER) [PubMed:21236704] [show Abstract] Mining the genome of the pathogenic fungus Aspergillus terreus revealed the presence of an orphan polyketide-nonribosomal-peptide synthetase (PKS-NRPS) gene cluster. Induced expression of the transcriptional activator gene adjacent to the PKS-NRPS gene was not sufficient for the activation of the silent pathway. Monitoring gene expression, metabolic profiling, and using a lacZ reporter strain allowed for the systematic investigation of physiological conditions that eventually led to the discovery of isoflavipucine and dihydroisoflavipucine. Phytotoxin formation is only activated in the presence of certain amino acids, stimulated at alkaline pH, but strictly repressed in the presence of glucose. Global carbon catabolite repression by CreA cannot be abolished by positive-acting factors such as PacC and overrides the pathway activator. Gene inactivation and stable isotope labeling experiments unveiled the molecular basis for flavipucine/fruit rot toxin biosynthesis. |
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