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Neosartoricin Sale

目录号 : GC48484

A prenylated tricyclic polyketide

Neosartoricin Chemical Structure

Cas No.:1421941-29-8

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1mg
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产品描述

Neosartoricin is a prenylated tricyclic polyketide produced in A. fumigatus and N. fischeri overexpressing the N. fischeri polycyclic prenyltransferase (pcPTase) nsc gene cluster.1 It inhibits the proliferation of anti-CD3 and anti-CD28-stimulated mouse spleen T cells (IC50 = 2.99 μM).

1.Chooi, Y.-H., Fang, J., Liu, H., et al.Genome mining of a prenylated and immunosuppressive polyketide from pathogenic fungiOrg. Lett.15(4)780-783(2013)

Chemical Properties

Cas No. 1421941-29-8 SDF
Canonical SMILES OC1=C2C(C[C@](O)([C@@H](C2=O)OC(C)=O)CC(/C=C(O)/C)=O)=C(C3=CC(O)=CC(O)=C31)C/C=C(C)\C
分子式 C26H28O9 分子量 484.5
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10 mM 0.2064 mL 1.032 mL 2.064 mL
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Research Update

Genome mining of a prenylated and immunosuppressive polyketide from pathogenic fungi

Org Lett 2013 Feb 15;15(4):780-3.PMID:23368997DOI:10.1021/ol303435y.

Activation of the polycyclic polyketide prenyltransferase (pcPTase)-containing silent clusters in Aspergillus fumigatus and Neosartorya fischeri led to isolation of a new metabolite Neosartoricin (3). The structure of 3 was solved by X-ray crystallography and NMR to be a prenylated anthracenone. 3 exhibits T-cell antiproliferative activity with an IC(50) of 3 μM, suggestive of a physiological role as an immunosuppressive agent.

Generation and comprehensive analysis of Synechococcus elongatus-Aspergillus nidulans co-culture system for polyketide production

Biotechnol Biofuels Bioprod 2023 Mar 1;16(1):32.PMID:36859469DOI:10.1186/s13068-023-02283-6.

Background: Artificial microbial consortia composed of heterotrophic and photoautotrophic organisms represent a unique strategy for converting light energy and carbon dioxide into high-value bioproducts. Currently, the types of desired bioproducts are still limited, and microbial fitness benefit rendered by paired partner generally needs to be intensified. Exploring novel artificial microbial consortia at a laboratory scale is an essential step towards addressing this unmet need. This study aimed to conduct and analyze an artificial consortium composed of cyanobacterium Synechococcus elongatus FL130 with the filamentous fungus Aspergillus nidulans TWY1.1 for producing fungi-derived secondary metabolite of polyketide Neosartoricin B. Results: Polyketide-producing A. nidulans TWY1.1 substantially ameliorated the growth and the survival of sucrose-secreting cyanobacterium S. elongatus FL130 in salt-stressed environments. Besides sucrose, comparable amounts of other carbohydrates were released from axenically cultured FL130 cells, which could be efficiently consumed by TWY1.1. Relative to axenically cultured FL130, less glycogen was accumulated in FL130 cells co-cultured with TWY1.1, and the glycogen phosphorylase gene catalyzing the first step for glycogen degradation had two-fold expression. Different from axenically cultured filamentous fungi, abundant vacuoles were observed in fungal hyphae of TWY1.1 co-cultured with cyanobacterium FL130. Meanwhile, FL130 cells displayed a characteristic pattern of interacting with its heterotrophic partner, densely dispersing along certain hyphae of TWY1.1. Finally, polyketide Neosartoricin B was produced from TWY1.1 in FL130-TWY1.1 co-cultures, which was tightly adjusted by nitrogen level. Conclusion: Overall, the results thoroughly proved the concept of pairing cyanobacteria with filamentous fungi to build artificial consortia for producing fungi-derived biomolecules.

Genome Mining of Aspergillus hancockii Unearths Cryptic Polyketide Hancockinone A Featuring a Prenylated 6/6/6/5 Carbocyclic Skeleton

Org Lett 2021 Nov 19;23(22):8789-8793.PMID:34747627DOI:10.1021/acs.orglett.1c03283.

Activation of a cryptic polyketide synthase gene cluster hkn from Aspergillus hancockii via overexpression of the gene-cluster-specific transcription factor HknR led to the discovery of a novel polycyclic metabolite, which we named hancockinone A. The compound features an unprecedented prenylated 6/6/6/5 tetracarbocyclic skeleton and shows moderate antibacterial activity. Heterologous expression, substrate feeding, and in vitro assays confirmed the role of cytochrome P450 HknE in constructing the five-membered ring in hancockinone A from the precursor Neosartoricin B.

Discovery of cryptic polyketide metabolites from dermatophytes using heterologous expression in Aspergillus nidulans

ACS Synth Biol 2013 Nov 15;2(11):629-34.PMID:23758576DOI:10.1021/sb400048b.

Dermatophytes belonging to the Trichophyton and Arthroderma genera cause skin infections in humans and animals. From genome sequencing data, we mined a conserved gene cluster among dermatophytes that are homologous to one that produces an immunosuppressive polyketide in Aspergillus fumigatus. Using a recombination-based cloning strategy in yeast, we constructed fungal heterologous expression vectors that encode the cryptic clusters. When integrated into the model Aspergillus nidulans host, a structurally related compound Neosartoricin B was formed, suggesting a possible role of this compound in the pathogenesis of these strains.