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Pyranonigrin A Sale

(Synonyms: 7-hydroxy Pyranonigrin S) 目录号 : GC40006

A fungal metabolite with antioxidant activity

Pyranonigrin A Chemical Structure

Cas No.:773855-65-5

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500μg
¥1,696.00
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1mg
¥3,221.00
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产品描述

Pyranonigrin A is a fungal metabolite originally isolated from Aspergillus that has antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH;) free radicals in a cell-free assay (IC50 = 132.9 μM). Pyranonigrin A (10 μM) suppresses TNF-α-induced expression of vascular cell adhesion molecule 1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs).

Chemical Properties

Cas No. 773855-65-5 SDF
别名 7-hydroxy Pyranonigrin S
Canonical SMILES C/C=C/C1=C(O)C(C(C(N[C@@H]2O)=O)=C2O1)=O
分子式 C10H9NO5 分子量 223.2
溶解度 DMSO: Soluble,Methanol: Heated 储存条件 Store at -20°C
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1 mM 4.4803 mL 22.4014 mL 44.8029 mL
5 mM 0.8961 mL 4.4803 mL 8.9606 mL
10 mM 0.448 mL 2.2401 mL 4.4803 mL
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Research Update

Reckoning a fungal metabolite, Pyranonigrin A as a potential Main protease (Mpro) inhibitor of novel SARS-CoV-2 virus identified using docking and molecular dynamics simulation

Biophys Chem 2020 Sep;264:106425.PMID:32663708DOI:10.1016/j.bpc.2020.106425.

The novel SARS-CoV-2 is the etiological agent causing the Coronavirus disease 2019 (COVID-19), which continues to become an inevitable pandemic outbreak. Over a short span of time, the structures of therapeutic target proteins for SARS-CoV-2 were identified based on the homology modelled structure of similar SARS-CoV transmission of 2003. Since the onset of the disease, the research community has been looking for a potential drug lead. Out of all the known resolved structures related to SARS-CoV, Main protease (Mpro) is considered an attractive anti-viral drug target on the grounds of its role in viral replication and probable non-interactive competency to bind to any viral host protein. To the best of our knowledge, till date only one compound has been identified and tested in-vivo as a potent inhibitor of Mpro protein, addressed as N3 (PubChem Compound CID: 6323191) and is known to bind irreversibly to Mpro suppressing its activity. Using computational approach, we intend to identify a probable natural fungal metabolite to interact and inhibit Mpro. After screening various small molecules for molecular docking and dynamics simulation, we propose Pyranonigrin A, a secondary fungal metabolite to possess potent inhibitory potential against the Main protease (Mpro) expressed in SARS-CoV-2 virus.

Metabolomic Analysis of Aspergillus niger Isolated From the International Space Station Reveals Enhanced Production Levels of the Antioxidant Pyranonigrin A

Front Microbiol 2020 May 21;11:931.PMID:32670208DOI:10.3389/fmicb.2020.00931.

Secondary metabolite (SM) production in Aspergillus niger JSC-093350089, isolated from the International Space Station (ISS), is reported, along with a comparison to the experimentally established strain ATCC 1015. The analysis revealed enhanced production levels of naphtho-γ-pyrones and therapeutically relevant SMs, including bicoumanigrin A, aurasperones A and B, and the antioxidant Pyranonigrin A. Genetic variants that may be responsible for increased SM production levels in JSC-093350089 were identified. These findings include INDELs within the predicted promoter region of flbA, which encodes a developmental regulator that modulates Pyranonigrin A production via regulation of Fum21. The Pyranonigrin A biosynthetic gene cluster was confirmed in A. niger, which revealed the involvement of a previously undescribed gene, pyrE, in its biosynthesis. UVC sensitivity assays enabled characterization of Pyranonigrin A as a UV resistance agent in the ISS isolate.

Secondary metabolites from a peanut-associated fungus Aspergillus niger IMBC-NMTP01 with cytotoxic, anti-inflammatory, and antimicrobial activities

Nat Prod Res 2022 Mar;36(5):1215-1223.PMID:33375869DOI:10.1080/14786419.2020.1868462.

Chemical investigation of a peanut-associated fungal strain Aspergillus niger IMBC-NMTP01 resulted in isolation and identification of 14 secondary metabolites, including two new, epi-aspergillusol (1) and aspernigin (3), and 12 known compounds: pyrophen (2), 2-(hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid (4), aspergillusol A (5), rubrofusarin B (6), nigerasperone A (7), fonsecin (8), TMC-256C1 (9), Pyranonigrin A (10), orlandin (11), nigerasperone C (12), asperpyrone A (13), and 5-(hydroxymethyl)-2-furancarboxylic acid (14). Compounds 9, 12-14 showed cytotoxicity toward all six human cancer cell lines, including HepG2, KB, HL-60, MCF-7, SK-Mel2, and LNCaP, with IC50 values ranging from 8.4 to 84.5 ?M, compounds 3-5 were cytotoxic against five cancer cell lines except HepG2, whereas 1 exhibited cytotoxicity toward HepG2, KB, and MCF-7 cells. All of the compounds, except 2 and 13, inhibited NO overproduction in LPS-induced RAW264.7 cells. In addition, all of the compounds displayed antimicrobial effects against Enterococcus faecalis, whereas 13 compounds, except 10, significantly inhibited the growth of the yeast Candida albicans.

Reassessing the structure of pyranonigrin

J Nat Prod 2007 Jul;70(7):1180-7.PMID:17604395DOI:10.1021/np070175n.

Fermentation extracts of the marine fungus Aspergillus niger LL-LV3020 were found to have relevant activity in a number of assays. Chemical screening of the extracts revealed that this organism produced numerous secondary metabolites in addition to its principal metabolite, citric acid. The compound with the most significant UV peak was isolated and its structure elucidated. Physical data suggested that this compound is identical with Pyranonigrin A (1); however, our structure elucidation led to a different assignment than previously reported. On the basis of analysis of all data, we propose a correction to the structure of Pyranonigrin A. Its absolute configuration was determined by electronic circular dichroism measurements in comparison with theoretical values calculated via ab initio time-dependent density functional theory and assigned as (7R)-3,7-dihydroxy-2-[(1E)-prop-1-enyl]-6,7-dihydropyrano[2,3-c]pyrrole-4,5-dione.

Medical Application of Substances Derived from Non-Pathogenic Fungi Aspergillus oryzae and A. luchuensis-Containing Koji

J Fungi (Basel) 2021 Mar 24;7(4):243.PMID:33804991DOI:10.3390/jof7040243.

Although most fungi cause pathogenicity toward human beings, dynasties of the East Asian region have domesticated and utilized specific fungi for medical applications. The Japanese dynasty and nation have domesticated and utilized koji fermented with non-pathogenic fungus Aspergillus oryzae for more than 1300 years. Recent research has elucidated that koji contains medicinal substances such as Taka-diastase, acid protease, koji glycosylceramide, kojic acid, oligosaccharides, ethyl-α-d-glucoside, ferulic acid, ergothioneine, pyroglutamyl leucine, Pyranonigrin A, resistant proteins, deferriferrichrysin, polyamines, Bifidobacterium-stimulating peptides, angiotensin I-converting enzyme inhibitor peptides, 14-dehydroergosterol, beta-glucan, biotin, and citric acid. This review introduces potential medical applications of such medicinal substances to hyperlipidemia, diabetes, hypertension, cardiovascular and cognitive diseases, chronic inflammation, epidermal permeability barrier disruption, coronavirus disease 2019 (COVID-19), and anti-cancer therapy.