Anhydrofulvic acid
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05663 |
| CAS | 95730-85-1 |
| Molecular Weight | 290.23 |
| Molecular Formula | C14H10O7 |
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Description
In acidic condition, Anhydrofulvic acid inhibits mitochondrial respiration of Candida utilis using both succinate and cytochrome C as respiratory substrates, but not using NADH. Anhydrofulvic acid has antifungal activity.
Specification
| Synonyms | 1H,10H-Pyrano[4,3-b][1]benzopyran-9-carboxylic acid, 7,8-dihydroxy-3-methyl-10-oxo-; 7,8-dihydroxy-3-methyl-10-oxo-1H-pyrano[4,3-b]chromene-9-carboxylic acid |
| IUPAC Name | 7,8-dihydroxy-3-methyl-10-oxo-1H,10H-pyrano[4,3-b]chromene-9-carboxylic acid |
| Canonical SMILES | CC1=CC2=C(CO1)C(=O)C3=C(O2)C=C(C(=C3C(=O)O)O)O |
| InChI | InChI=1S/C14H10O7/c1-5-2-8-6(4-20-5)12(16)10-9(21-8)3-7(15)13(17)11(10)14(18)19/h2-3,15,17H,4H2,1H3,(H,18,19) |
| InChI Key | QECRRBWJXIZNNN-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 616.5±55.0°C at 760 mmHg |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1. Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity
Decha Kumla, José A Pereira, Tida Dethoup, Luis Gales, Joana Freitas-Silva, Paulo M Costa, Michael Lee, Artur M S Silva, Nazim Sekeroglu, Madalena M M Pinto, Anake Kijjoa Mar Drugs. 2018 Aug 20;16(8):289. doi: 10.3390/md16080289.
A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone (3b), spirofuranochromone (4), 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (5), a pyranochromone dimer (6) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin (1a), 12-methoxycitromycin (1b), myxotrichin D (1d), 12-methoxycitromycetin (1e), anhydrofulvic acid (2a), myxotrichin C (2b), penialidin D (2c), penialidin F (3a), SPF-3059-30 (7), GKK1032B (8) and secalonic acid A (9), from cultures of the marine sponge- associated fungus Penicillium erubescens KUFA0220. Compounds 1a⁻e, 2a, 3a, 4, 7⁻9, were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 8 exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas 9 showed growth inhibition of methicillin-resistant Staphyllococus aureus (MRSA). None of the compounds were active against Gram-negative bacteria tested.
2. A Secondary Metabolite of Cercospora sp., Associated with Rosa damascena Mill., Inhibits Proliferation, Biofilm Production, Ergosterol Synthesis and Other Virulence Factors in Candida albicans
Abid Bashir, Tanveer Ahmad, Sadaqat Farooq, Waseem I Lone, Malik M Manzoor, Yedukondalu Nalli, Phalisteen Sultan, Asha Chaubey, Asif Ali, Syed Riyaz-Ul-Hassan Microb Ecol. 2022 Apr 2. doi: 10.1007/s00248-022-02003-x. Online ahead of print.
Here we describe the antimicrobial potential of secondary metabolites, fulvic acid (F.A.) and anhydrofulvic acid (AFA), produced by RDE147, an endophyte of Rosa damascena Mill. The endophyte was identified as Cercospora piaropi by ITS and β-tubulin-based phylogenetic analyses, while chemoprofiling of the endophyte by column chromatography and spectroscopy yielded two pure compounds, F.A. and AFA. The compounds demonstrated different antimicrobial profiles, with AFA suppressing the growth of C. albicans at 7.3 µg ml-1 IC50. Further studies revealed that AFA strongly restricted the biofilm production and hyphae formation in C. albicans by down-regulating several biofilm and morphogenesis-related genes. The time-kill assays confirmed the fungicidal activity of AFA against C. albicans, killing 83.6% of the pathogen cells in 24 h at the MIC concentration, and the post-antibiotic effect (PAE) experiments established the suppression of C. albicans growth for extended time periods. The compound acted synergistically with amphotericin B and nystatin and reduced ergosterol biosynthesis by the pathogen, confirmed by ergosterol estimation and comparative expression profiling of selected genes and molecular docking of AFA with C. albicans squalene epoxidase. AFA also suppressed the expression of several other virulence genes of the fungal pathogen. The study determines the anti-C. albicans potential of AFA and its impact on the biology of the pathogen. It also indicates that Cercospora species may yield potential bioactive molecules, especially fulvic acid derivatives. However, it is imperative to conduct in vivo studies to explore this molecule's therapeutic potential further.
3. PTP1B inhibitory and anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungus Penicillium sp. JF-55
Dong-Sung Lee, Jae-Hyuk Jang, Wonmin Ko, Kyoung-Su Kim, Jae Hak Sohn, Myeong-Suk Kang, Jong Seog Ahn, Youn-Chul Kim, Hyuncheol Oh Mar Drugs. 2013 Apr 23;11(4):1409-26. doi: 10.3390/md11041409.
Protein tyrosine phosphatase 1B (PTP1B) plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 cultures afforded a new PTP1B inhibitory styrylpyrone-type metabolite named penstyrylpyrone (1), and two known metabolites, anhydrofulvic acid (2) and citromycetin (3). Compounds 1 and 2 inhibited PTP1B activity in a dose-dependent manner, and kinetic analyses of PTP1B inhibition suggested that these compounds inhibited PTP1B activity in a competitive manner. In an effort to gain more biological potential of the isolated compounds, the anti-inflammatory effects of compounds 1-3 were also evaluated. Among the tested compounds, only compound 1 inhibited the production of NO and PGE2, due to the inhibition of the expression of iNOS and COX-2. Penstyrylpyrone (1) also reduced TNF-α and IL-1β production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), an inhibitor of HO-1, it was verified that the inhibitory effects of penstyrylpyrone (1) on the pro-inflammatory mediators and NF-κB DNA binding activity were associated with the HO-1 expression. Therefore, these results suggest that penstyrylpyrone (1) suppresses PTP1B activity, as well as the production of pro-inflammatory mediators via NF-κB pathway, through expression of anti-inflammatory HO-1.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
