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(-)-Viriditoxin Sale

目录号 : GC45253

A mycotoxin with antibacterial and antiproliferative activity

(-)-Viriditoxin Chemical Structure

Cas No.:1381782-08-6

规格 价格 库存 购买数量
500μg
¥2,209.00
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产品描述

(-)-Viriditoxin is a mycotoxin originally isolated from A. viridinutans that has antibacterial and antiproliferative activity. It is active against methicillin-sensitive and -resistant S. aureus (MSSA and MRSA, respectively), tetracycline-sensitive and -resistant Staphylococcus, vancomycin-sensitive and -resistant Enterococcus, and penicillin-sensitive and -resistant S. pneumoniae (MICs = 2-32 μg/ml). (-)-Viriditoxin is also active against fish pathogens, including S. iniae and S. parauberis (MICs = 0.16-0.21 μg/ml). It inhibits polymerization and the GTPase activity of E. coli FtsZ, a tubulin-like GTPase involved in bacterial cell division (IC50s = 8.2 and 7 μg/ml, respectively). (-)-Viriditoxin inhibits proliferation of human DU145, LNCaP, and PC3 prostate cancer cells (IC50s = 5.36, 0.63, and 7.6 μM, respectively) . It is also toxic to mice (LD50 = 2.8 mg/kg, i.p.).

Chemical Properties

Cas No. 1381782-08-6 SDF
Canonical SMILES OC1=CC(OC)=[C@]([C@]2=C(OC)C=C(O)C3=C2C=C(C[C@@H](CC(OC)=O)OC4=O)C4=C3O)C5=C1C(O)=C6C(C[C@@H](CC(OC)=O)OC6=O)=C5
分子式 C34H30O14 分子量 662.6
溶解度 DMSO: soluble,Ethanol: soluble 储存条件 Store at -20°C
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1 mM 1.5092 mL 7.546 mL 15.0921 mL
5 mM 0.3018 mL 1.5092 mL 3.0184 mL
10 mM 0.1509 mL 0.7546 mL 1.5092 mL
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Research Update

Second-Generation Synthesis of (-)-Viriditoxin

Synthesis (Stuttg) 2012;2012(3):362-371.PMID:23049144DOI:10.1055/s-0031-1289651.

Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.

The fungal gene cluster for biosynthesis of the antibacterial agent viriditoxin

Fungal Biol Biotechnol 2019 Jul 1;6:2.PMID:31304040DOI:10.1186/s40694-019-0072-y.

Background: Viriditoxin is one of the 'classical' secondary metabolites produced by fungi and that has antibacterial and other activities; however, the mechanism of its biosynthesis has remained unknown. Results: Here, a gene cluster (vdt) responsible for viriditoxin synthesis was identified, via a bioinformatics analysis of the genomes of Paecilomyces variotii and Aspergillus viridinutans that both are viriditoxin producers. The function of the eight-membered gene cluster of P. variotii was characterized by targeted gene disruptions, revealing the roles of each gene in the synthesis of this molecule and establishing its biosynthetic pathway, which includes a Baeyer-Villiger monooxygenase catalyzed reaction. Additionally, a predicted catalytically-inactive hydrolase was identified as being required for the stereoselective biosynthesis of (M)-Viriditoxin. The subcellular localizations of two proteins (VdtA and VdtG) were determined by fusing these proteins to green fluorescent protein, to establish that at least two intracellular structures are involved in the compartmentalization of the synthesis steps of this metabolite. Conclusions: The predicted pathway for the synthesis of viriditoxin was established by a combination of genomics, bioinformatics, gene disruption and chemical analysis processes. Hence, this work reveals the basis for the synthesis of an understudied class of fungal secondary metabolites and provides a new model species for understanding the synthesis of biaryl compounds with a chiral axis.

Fungal Dirigent Protein Controls the Stereoselectivity of Multicopper Oxidase-Catalyzed Phenol Coupling in Viriditoxin Biosynthesis

J Am Chem Soc 2019 May 22;141(20):8068-8072.PMID:31045362DOI:10.1021/jacs.9b03354.

Paecilomyces variotii produces the antibacterial and cytotoxic ( M)-Viriditoxin (1) together with a trace amount of its atropisomer ( P)-Viriditoxin 1'. Elucidation of the biosynthesis by heterologous pathway reconstruction in Aspergillus nidulans identified the multicopper oxidase (MCO) VdtB responsible for the regioselective 6,6'-coupling of semiviriditoxin (10), which yielded 1 and 1' at a ratio of 1:2. We further uncovered that VdtD, an α/β hydrolase-like protein lacking the catalytic serine, directs the axial chirality of the products. Using recombinant VdtB and VdtD as cell-free extracts from A. nidulans, we demonstrated that VdtD acts like a dirigent protein to control the stereoselectivity of the coupling catalyzed by VdtB to yield 1 and 1' at a ratio of 20:1. Furthermore, we uncovered a unique Baeyer-Villiger monooxygenase (BVMO) VdtE that could transform the alkyl methylketone side chain to methyl ester against the migratory aptitude.