Lateropyrone
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| Category | Others |
| Catalog number | BBF-03997 |
| CAS | 93752-78-4 |
| Molecular Weight | 318.23 |
| Molecular Formula | C15H10O8 |
| Purity | >99% by HPLC |
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Description
An unusual heterocyclic metabolite isolated from fusarium avenaceum with antibacterial and antifungal activity.
Specification
| Synonyms | Avenacein Y |
| Storage | Store at -20°C |
| IUPAC Name | methyl 5,9-dihydroxy-2-methyl-4,6-dioxopyrano[3,4-g]chromene-8-carboxylate |
| Canonical SMILES | CC1=CC(=O)C2=C(O1)C=C3C(=C2O)C(=O)OC(=C3O)C(=O)OC |
| InChI | InChI=1S/C15H10O8/c1-5-3-7(16)10-8(22-5)4-6-9(12(10)18)14(19)23-13(11(6)17)15(20)21-2/h3-4,17-18H,1-2H3 |
| InChI Key | JSQAILNRMPHAGO-UHFFFAOYSA-N |
| Source | Fusarium sp. |
Properties
| Appearance | Tan Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 598°C at 760 mmHg |
| Density | 1.643 g/cm3 |
| Solubility | Soluble in DMF, DMSO |
Reference Reading
1. Co-culture of the fungus Fusarium tricinctum with Streptomyces lividans induces production of cryptic naphthoquinone dimers
Peter Proksch, Zhen Liu, Holger Gohlke, Rainer Kalscheuer, Attila Mándi, Mariam Moussa, Wenhan Lin, Michele Bonus, Tibor Kurtán, Rudolf Hartmann, Weaam Ebrahim RSC Adv . 2019 Jan 11;9(3):1491-1500. doi: 10.1039/c8ra09067j.
Co-cultivation of the endophytic fungusFusarium tricinctumwithStreptomyces lividanson solid rice medium led to the production of four new naphthoquinone dimers, fusatricinones A-D (1-4), and a new lateropyrone derivative, dihydrolateropyrone (5), that were not detected in axenic fungal controls. In addition, four known cryptic compounds, zearalenone (7), (-)-citreoisocoumarin (8), macrocarpon C (9) and 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (10), that were likewise undetectable in extracts from fungal controls, were obtained from the co-culture extracts. The known antibiotically active compound lateropyrone (6), the depsipeptides enniatins B (11), B1 (12) and A1 (13), and the lipopeptide fusaristatin A (14), that were present in axenic fungal controls and in co-culture extracts, were upregulated in the latter. The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The relative and absolute configuration of dihydrolateropyrone (5) was elucidated by TDDFT-ECD calculations.
2. Inducing secondary metabolite production by the endophytic fungus Fusarium tricinctum through coculture with Bacillus subtilis
Peter Proksch, Antonius R B Ola, Dhana Thomy, Daowan Lai, Heike Brötz-Oesterhelt J Nat Prod . 2013 Nov 22;76(11):2094-9. doi: 10.1021/np400589h.
Coculturing the fungal endophyte Fusarium tricinctum with the bacterium Bacillus subtilis 168 trpC2 on solid rice medium resulted in an up to 78-fold increase in the accumulation in constitutively present secondary metabolites that included lateropyrone (5), cyclic depsipeptides of the enniatin type (6-8), and the lipopeptide fusaristatin A (9). In addition, four compounds (1-4) including (-)-citreoisocoumarin (2) as well as three new natural products (1, 3, and 4) were not present in discrete fungal and bacterial controls and only detected in the cocultures. The new compounds were identified as macrocarpon C (1), 2-(carboxymethylamino)benzoic acid (3), and (-)-citreoisocoumarinol (4) by analysis of the 1D and 2D NMR and HRMS data. Enniatins B1 (7) and A1 (8), whose production was particularly enhanced, inhibited the growth of the cocultivated B. subtilis strain with minimal inhibitory concentrations (MICs) of 16 and 8 μg/mL, respectively, and were also active against Staphylococcus aureus, Streptococcus pneumoniae, and Enterococcus faecalis with MIC values in the range 2-8 μg/mL. In addition, lateropyrone (5), which was constitutively present in F. tricinctum, displayed good antibacterial activity against B. subtilis, S. aureus, S. pneumoniae, and E. faecalis, with MIC values ranging from 2 to 8 μg/mL. All active compounds were equally effective against a multiresistant clinical isolate of S. aureus and a susceptible reference strain of the same species.
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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 ╳
