Aszonapyrone A
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| Category | Antibiotics |
| Catalog number | BBF-00127 |
| CAS | 83103-08-6 |
| Molecular Weight | 456.61 |
| Molecular Formula | C28H40O5 |
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Description
Aszonapyrone A is a lactone antibiotic produced by Aspergillus zonatus, which has anti-Staphylococcus aureus activity.
Specification
| IUPAC Name | [(2S,4aR,4bS,8R,8aS,10aR)-8-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-1,1,4a,8a-tetramethyl-7-methylidene-2,3,4,4b,5,6,8,9,10,10a-decahydrophenanthren-2-yl] acetate |
| Canonical SMILES | CC1=CC(=C(C(=O)O1)CC2C(=C)CCC3C2(CCC4C3(CCC(C4(C)C)OC(=O)C)C)C)O |
| InChI | InChI=1S/C28H40O5/c1-16-8-9-23-27(6,20(16)15-19-21(30)14-17(2)32-25(19)31)12-10-22-26(4,5)24(33-18(3)29)11-13-28(22,23)7/h14,20,22-24,30H,1,8-13,15H2,2-7H3/t20-,22+,23+,24+,27+,28+/m1/s1 |
| InChI Key | QZWJQNIIRYNONX-NEKODSHDSA-N |
Properties
| Appearance | Colorless needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 242-244°C |
Reference Reading
1. Bioactive Secondary Metabolites from a Thai Collection of Soil and Marine-Derived Fungi of the Genera Neosartorya and Aspergillus
War War May Zin, Chadaporn Prompanya, Suradet Buttachon, Anake Kijjoa Curr Drug Deliv. 2016;13(3):378-88. doi: 10.2174/1567201813666160303104641.
Background: Fungi are microorganisms which can produce interesting secondary metabolites with structural diversity. Although terrestrial fungi have been extensively investigated for their bioactive secondary metabolites such as antibiotics, marine-derived fungi have only recently attracted attention of Natural Products chemists. Methods: Our group has been working on the secondary metabolites produced by the cultures of the fungi of the genera Neosartorya and Aspergillus, collected from soil and marine environments from the tropical region for the purpose of finding new leads for anticancer and antibacterial drugs. Results: This review covers only the secondary metabolites of four soil and six marine-derived species of Neosarorya as well as a new species of marine-derived Aspergillus, investigated by our group. In total, we have isolated fifty three secondary metabolites which can be categorized as polyketides (two), isocoumarins (six), terpenoids (two), meroterpenes (fourteen), alkaloids (twenty eight) and cyclic peptide (one). The anticancer and antibacterial activities of these fungal metabolites are also discussed. Conclusion: Among fifty three secondary metabolites isolated, only the alkaloid eurochevalierine and the cadinene sesquiterpene, isolated from the soil fungus N. pseudofisheri, showed relevant in vitro cytostatic activity against glioblastoma (U373) and non-small cell lung cancer (A549) cell lines while the meroditerpene aszonapyrone A exhibited strong antibacterial activity against multidrug-resistant Gram-positive bacteria and also strong antibiofilm activity in these isolates.
2. Thermal shift assays of marine-derived fungal metabolites from Aspergillus fischeri MMERU 23 against Leishmania major pteridine reductase 1 and molecular dynamics studies
Harol R Arias Cardona, Thamires Q Froes, Bruno C De Souza, Franco H A Leite, Hugo Neves Brandão, Jamrearn Buaruang, Anake Kijjoa, Clayton Q Alves J Biomol Struct Dyn. 2022;40(22):11968-11976. doi: 10.1080/07391102.2021.1966510. Epub 2021 Aug 20.
Marine-derived fungi are a promising source of bioactive molecules, especially species from extreme habitats. Although several secondary metabolites such as meroterpenoids and alkaloids have been isolated from cultures of Aspergillus fischeri, obtained from terrestrial habitats, there is no report on compounds isolated from marine-derived strains. Many metabolites isolated from marine-derived fungi exhibited a myriad of biological activities. Marine natural products have shown to be an important source of bioactive compounds and can assist in the discovery of molecules with affinity against validated targets from exclusive strains of parasites of medical importance such as pteridine reductase 1 (PTR1), from Leishmania major, which is essential for cell growth. Leishmaniasis is responsible for approximately 65,000 annual deaths. Despite the mortality data, drugs available for the treatment of patients are insufficient and have moderate therapeutic efficacy in addition to serious adverse effects, which make the development of new drugs urgent. The previously described aszonalenin (ASL), aszonapyrone A (ASP), acetylaszonalenin (ACZ), and helvolic acid (HAC) were isolated from the ethyl acetate extract of the culture of a marine sponge-associated A. fischeri MMERU 23 and their affinities against PTR1 were determined by ThermoFluor®. Among the tested compounds, only ACZ showed dose-dependent affinity against PTR1. Moreover, complementary molecular dynamics studies (t = 100 000 ps) have showed that this molecule performs hydrogen bonds with key residues at the active site for more than 60% of the productive trajectory time. The results indicate that ACZ could be a promising PTR1 inhibitor and a potential candidate for development of antileishmanial drug.Communicated by Ramaswamy H. Sarma.
3. A New Meroditerpene and a New Tryptoquivaline Analog from the Algicolous Fungus Neosartorya takakii KUFC 7898
War War May Zin, Suradet Buttachon, Jamrearn Buaruang, Luís Gales, José A Pereira, Madalena M M Pinto, Artur M S Silva, Anake Kijjoa Mar Drugs. 2015 Jun 15;13(6):3776-90. doi: 10.3390/md13063776.
A new meroditerpene sartorenol (1), a new natural product takakiamide (2) and a new tryptoquivaline analog (3) were isolated, together with nine known compounds, including aszonapyrone A, chevalone B, aszonalenin, acetylaszonalenin, 3'-(4-oxoquinazolin-3-yl) spiro[1H-indole-3,5'-oxolane]-2,2'-dione, tryptoquivalines L, F and H, and the isocoumarin derivative, 6-hydroxymellein, from the ethyl acetate extract of the culture of the algicolous fungus Neosartorya takakii KUFC 7898. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and, in the case of sartorenol (1) and tryptoquivaline U (3), X-ray analysis was used to confirm their structures and to determine the absolute configuration of their stereogenic carbons. Compounds 1, 2 and 3 were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria, and multidrug-resistant isolates from the environment; however, none exhibited antibacterial activity (MIC ˃ 256 mg/mL). The three new compounds did not show any quorum sensing inhibition in the screening protocol based on the pigment production by Chromobacterium violaceum (ATCC 31532).
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
