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Andrastin A Sale

(Synonyms: NSC 697452) 目录号 : GC42806

A meroterpenoid farnesyltransferase inhibitor

Andrastin A Chemical Structure

Cas No.:174232-42-9

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500μg
¥2,827.00
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产品描述

Andrastin A is a meroterpenoid farnesyltransferase inhibitor. It increases the accumulation and effect of the chemotheraputic agent vincristine (sulfate) , most likely by binding to plasma membrane phosphoglycoprotein to prevent drug efflux. Andrastin A inhibits survival of Caco-2 cells with an IC50 of >50 μg/ml.

Chemical Properties

Cas No. 174232-42-9 SDF
别名 NSC 697452
Canonical SMILES CC1=C[C@]2([H])[C@]([C@@](C(C3C)=O)(C(OC)=O)[C@]1(C)C3=O)(C)CC[C@]4([H])C(C)(C)[C@@H](OC(C)=O)CC[C@]42C=O
分子式 C28H38O7 分子量 486.6
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Research Update

The Biosynthetic Gene Cluster for Andrastin A in Penicillium roqueforti

Front Microbiol 2017 May 5;8:813.PMID:28529508DOI:10.3389/fmicb.2017.00813.

Penicillium roqueforti is a filamentous fungus involved in the ripening of several kinds of blue cheeses. In addition, this fungus produces several secondary metabolites, including the meroterpenoid compound Andrastin A, a promising antitumoral compound. However, to date the genomic cluster responsible for the biosynthesis of this compound in P. roqueforti has not been described. In this work, we have sequenced and annotated a genomic region of approximately 29.4 kbp (named the adr gene cluster) that is involved in the biosynthesis of Andrastin A in P. roqueforti. This region contains ten genes, named adrA, adrC, adrD, adrE, adrF, adrG, adrH, adrI, adrJ and adrK. Interestingly, the adrB gene previously found in the adr cluster from P. chrysogenum, was found as a residual pseudogene in the adr cluster from P. roqueforti. RNA-mediated gene silencing of each of the ten genes resulted in significant reductions in Andrastin A production, confirming that all of them are involved in the biosynthesis of this compound. Of particular interest was the adrC gene, encoding for a major facilitator superfamily transporter. According to our results, this gene is required for the production of Andrastin A but does not have any role in its secretion to the extracellular medium. The identification of the adr cluster in P. roqueforti will be important to understand the molecular basis of the production of Andrastin A, and for the obtainment of strains of P. roqueforti overproducing Andrastin A that might be of interest for the cheese industry.

Andrastin A and barceloneic acid metabolites, protein farnesyl transferase inhibitors from Penicillium albocoremium: chemotaxonomic significance and pathological implications

Mycol Res 2005 Nov;109(Pt 11):1243-9.PMID:16279417DOI:10.1017/s0953756205003734.

A survey of Penicillium albocoremium was undertaken to identify potential taxonomic metabolite markers. One major and four minor metabolites were consistently produced by the 19 strains surveyed on three different media. Following purification and spectral studies, the metabolites were identified as the known protein farnesyl transferase inhibitors Andrastin A (1) and barceloneic acid A (2) along with barceloneic acid B (3), barceloneic lactone (4), and methyl barceloneate (5). These compounds are significant taxonomic markers for P. albocoremium; moreover this is the first report of a methyl ester of a barceloneic acid being produced as a secondary metabolite. Tissue extracts created following pathogenicity trials involving P. albocoremium and Allium cepa confirmed the production of these five metabolites in planta. Barceloneic acid B was found to be biologically active against a P388 murine leukemia cell line.

Proteolytic activity, mycotoxins and Andrastin A in Penicillium roqueforti strains isolated from Cabrales, Valdeón and Bejes-Tresviso local varieties of blue-veined cheeses

Int J Food Microbiol 2009 Nov 30;136(1):18-25.PMID:19837474DOI:10.1016/j.ijfoodmicro.2009.09.014.

High quality local varieties of blue-veined cheese are made in the villages of the valleys of Cabrales, Valdeón and Bejes-Tresviso in North Spain. Penicillium roqueforti strains have been isolated from each of those blue cheeses and compared with the collection strain P. roqueforti CECT 2905 (ATCC 10110) and a strain 'Valdeón-industrial' used for large scale production of Valdeón cheese. Using molecular genetics techniques and 5.8S and 18S rRNAs and the D1-D2 regions of 28S rRNA all strains were identified as authentic P. roqueforti. These strains from local varieties of blue cheese could be distinguished from the Valdeón-industrial strain and the control strain CECT 2905 by the mitochondrial DNA restriction pattern. The industrial strain showed high levels of aspartylprotease AspA, whereas the culture collection strain showed barely detectable levels of this enzyme, as shown by proteolysis tests and by immunodetection with anti-AspA antibodies. The lipolytic activity was similar in the strains isolated from the three types of local blue cheeses. The strains isolated from the local varieties of the blue cheese produced moderate levels of PR toxin, whereas the Valdeón-industrial strains showed a higher content of this mycotoxin. All strains (except the control strain CECT 2905) showed similar levels of roquefortine C. The antitumoral compound Andrastin A was produced by all strains at different levels. P. roqueforti CECT 2905 showed high ability to synthesize this compound. Andrastin A was present in all industrial and local varieties of blue cheese. The content of Andrastin A was similar to that of other well-known blue cheeses from France and Denmark.

Enhancement of drug accumulation by Andrastin A produced by Penicillium sp. FO-3929 in vincristine-resistant KB cells

J Antibiot (Tokyo) 1998 Jan;51(1):68-72.PMID:9531989DOI:10.7164/antibiotics.51.68.

In the course of our screening for compounds that reverse multidrug resistance, we found that the cytotoxicity of vincristine was enhanced 1.5-20-fold depending on the concentration of Andrastin A in vincristine-resistant KB cells (VJ-300). Andrastin A alone had no effect on the growth of drug sensitive KB cells and VJ-300 cells. On the other hand, Andrastin A (25 and 50 micrograms/ml) significantly enhanced accumulation of [3H]vincristine in VJ-300 cells. Andrastin A (50 micrograms/ml) completely inhibited the binding of [3H]azidopine to the P-glycoprotein in VJ-300 cells. The result suggests that Andrastin A directly interacts with P-glycoprotein and inhibits the efflux of antitumor agents in drug resistant cells.

Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. II. Structure elucidation and biosynthesis

J Antibiot (Tokyo) 1996 May;49(5):418-24.PMID:8682717DOI:10.7164/antibiotics.49.418.

The structures of new protein farnesyltransferase inhibitors, andrastins A-C, were elucidated. The cyclopentane ring of andrastins exhibited keto-enol tautomerism, which made the structure hard to elucidate. Therefore, the structure of Andrastin A was elucidated by INADEQUATE and 13C-13C couplings using 13C-labeled Andrastin A. The absolute configuration of the p-bromobenzoyl derivative of Andrastin A was elucidated by X-ray crystallographic analysis and its skeleton was shown to be ent-5 alpha,14 beta-androstane. The biosynthesis of Andrastin A was also studied by the incorporation of 13C-labeled acetates. Though the andrastins had a common androstane skeleton, they were biosynthesized from a sesquiterpene and a tetraketide.