Desferritriacetylfusigen
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-05043 |
| CAS | 20186-12-3 |
| Molecular Weight | 852.92 |
| Molecular Formula | C39H60N6O15 |
Online Inquiry
Description
Desferritriacetylfusigen is an antibiotic derived from Aspergillus. It has activity against gram-positive and gram-negative bacteria.
Specification
| Synonyms | Acetamide, N,N',N''-(7,19,31-trihydroxy-10,22,34-trimethyl-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-triene-3,15,27-triyl)tris-, (Z,Z,Z)- (8CI); Acetamide, N,N',N''-(7,19,31-trihydroxy-10,22,34-trimethyl-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-triene-3,15,27-triyl)tris-, [3S-(3R*,9Z,15R*,21Z,27R*,33Z)]-; 1,13,25-Trioxa-7,19,31-triazacyclohexatriacontane, acetamide deriv.; N,N',N''-[(3S,9Z,15S,21Z,27S,33Z)-7,19,31-Trihydroxy-10,22,34-trimethyl-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-triene-3,15,27-triyl]tris[acetamide] |
| IUPAC Name | N-(15,27-diacetamido-7,19,31-trihydroxy-10,22,34-trimethyl-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-trien-3-yl)acetamide |
| Canonical SMILES | CC1=CC(=O)N(CCCC(C(=O)OCCC(=CC(=O)N(CCCC(C(=O)OCCC(=CC(=O)N(CCCC(C(=O)OCC1)NC(=O)C)O)C)NC(=O)C)O)C)NC(=O)C)O |
| InChI | InChI=1S/C39H60N6O15/c1-25-13-19-58-37(52)31(40-28(4)46)11-8-17-44(56)35(50)23-27(3)15-21-60-39(54)33(42-30(6)48)12-9-18-45(57)36(51)24-26(2)14-20-59-38(53)32(41-29(5)47)10-7-16-43(55)34(49)22-25/h22-24,31-33,55-57H,7-21H2,1-6H3,(H,40,46)(H,41,47)(H,42,48) |
| InChI Key | VGXYDZCCQDSGLZ-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 364.5±42.0°C (Predicted) |
| Density | 1.31±0.1 g/cm3 (Predicted) |
Reference Reading
1. Siderophore and indolic acid production by Paenibacillus triticisoli BJ-18 and their plant growth-promoting and antimicrobe abilities
Yunzhi Zhang, Jinwei Ren, Wenzhao Wang, Baosong Chen, Erwei Li, Sanfeng Chen PeerJ. 2020 Jul 14;8:e9403. doi: 10.7717/peerj.9403. eCollection 2020.
Paenibacillus triticisoli BJ-18, a N2-fixing bacterium, is able to promote plant growth, but the secondary metabolites that may play a role in promoting plant growth have never been characterized. In this study, untargeted metabolomics profiling of P. triticisoli BJ-18 indicated the existence of 101 known compounds, including N2-acetyl ornithine, which is the precursor of siderophores, plant growth regulators such as trehalose 6-phosphate, betaine and trigonelline, and other bioactive molecules such as oxymatrine, diosmetin, luotonin A, (-)-caryophyllene oxide and tetrahydrocurcumin. In addition, six compounds were also isolated from P. triticisoli BJ-18 using a combination of silica gel chromatography, sephadex LH-20, octadecyl silane (ODS), and high-performance liquid chromatography (HPLC). The compound structures were further analyzed by Nuclear Magnetic Resonance (NMR), Mass Spectrometry (MS), and Electronic Circular Dichroism (ECD). The six compounds included three classical siderophore fusarinines identified as deshydroxylferritriacetylfusigen, desferritriacetylfusigen, and triacetylfusigen, and three indolic acids identified as paenibacillic acid A, 3-indoleacetic acid (IAA), and 3-indolepropionic acid (IPA). Both deshydroxylferritriacetylfusigen and paenibacillic acid A have new structures. Fusarinines, which normally occur in fungi, were isolated from bacterium for the first time in this study. Both siderophores (compounds 1 and 2) showed antimicrobial activity against Escherichia coli, Staphylococcus aureus and Bacillus subtilis, but did not show obvious inhibitory activity against yeast Candida albicans, whereas triacetylfusigen (compound 3) showed no antibiosis activity against these test microorganisms. Paenibacillic acid A, IAA, and IPA were shown to promote the growth of plant shoots and roots, and paenibacillic acid A also showed antimicrobial activity against S. aureus. Our study demonstrates that siderophores and indolic acids may play an important role in plant growth promotion by P. triticisoli BJ-18.
2. [Secondary Metabolites of Fungi of the Usti Section, Genus Aspergillus and Their Application in Chemosystematics]
A G Kozlovskii, T V Antipova, V P Zhelifonova, B P Baskunov, N E Ivanushkina, G A Kochkina, S M Ozerskaya Mikrobiologiia. 2017 Mar-Apr;86(2):164-71.
Secondary metabolites of 22 fungal strains (genus Aspergillus, section Usti) isolated at diverse geographic regions, including the Arctic permafrost deposits, were studied. The studied strains were found to synthesize a variety of biologically active compounds, structurally identified as drimane sesqueterpenoids, isoquinoline alkaloids (TMC-120 A-C, derivative 1), meroterpenoids (austalides О and J), and anthraquinone pigments (averufin, versicolorin C). Desferritriacetylfusigen production by A. calidoustus isolates is reported for the first time. The individual spectra of secondary metabolites were used for reidentification of 17 strains, of which 15 were identified as A. calidoustus and two, as A. pseudodeflectus.
3. Chemical and physical modulation of antibiotic activity in emericella species
Mercedes de la Cruz, Jesús Martín, Victor González-Menéndez, Ignacio Pérez-Victoria, Catalina Moreno, José Rubén Tormo, Noureddine El Aouad, Josep Guarro, Francisca Vicente, Fernando Reyes, Gerald F Bills Chem Biodivers. 2012 Jun;9(6):1095-113. doi: 10.1002/cbdv.201100362.
The addition of epigenetic modifying agents and ion-exchange resins to culture media and solid-state fermentations have been promoted as ways to stimulate expression of latent biosynthetic gene clusters and to modulate secondary metabolite biosynthesis. We asked how combination of these treatments would affect a population of screening isolates and their patterns of antibiosis relative to fermentation controls. A set of 43 Emericella strains, representing 25 species and varieties, were grown on a nutrient-rich medium comprising glucose, casein hydrolysate, urea, and mineral salts. Each strain was grown in untreated agitated liquid medium, a medium treated with suberoylanilide hydroxamic acid, a histone deacetylase inhibitor, 5-azacytidine, a DNA methylation inhibitor, an Amberlite non-ionic polyacrylate resin, and the same medium incorporated into an inert static vermiculite matrix. Species-inherent metabolic differences more strongly influenced patterns of antibiosis than medium treatments. The antibacterial siderophore, desferritriacetylfusigen, was detected in most species in liquid media, but not in the vermiculite medium. The predominant antifungal component detected was echinocandin B. Some species produced this antifungal regardless of treatment, although higher quantities were often produced in vermiculite. Several species are reported for the first time to produce echinocandin B. A new echinocandin analog, echinocandin E, was identified from E. quadrilineata.
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
