Trypacidin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02723 |
| CAS | 1900-29-4 |
| Molecular Weight | 344.31 |
| Molecular Formula | C18H16O7 |
| Purity | ≥98% by HPLC |
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Description
It is produced by the strain of Aspergillus fumigatus. Trypacidin has anti-protozoal and spirochete effects, but the effect on the latter is weak.
Specification
| Synonyms | BRN 1299866; Methyl 4,6'-dimethoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexa[2,5]diene]-2'-carboxylate |
| Storage | Store at -20°C |
| IUPAC Name | methyl 4,5'-dimethoxy-6-methyl-3,3'-dioxospiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate |
| Canonical SMILES | CC1=CC2=C(C(=C1)OC)C(=O)C3(O2)C(=CC(=O)C=C3OC)C(=O)OC |
| InChI | InChI=1S/C18H16O7/c1-9-5-12(22-2)15-13(6-9)25-18(16(15)20)11(17(21)24-4)7-10(19)8-14(18)23-3/h5-8H,1-4H3 |
| InChI Key | KMZYINVXZDQCKC-UHFFFAOYSA-N |
Properties
| Appearance | Flaky or Ribbed Crystal |
| Boiling Point | 582.2°C at 760 mmHg |
| Melting Point | 228-231°C |
| Density | 1.37 g/cm3 |
Reference Reading
1. Identification of the antiphagocytic trypacidin gene cluster in the human-pathogenic fungus Aspergillus fumigatus
Axel A Brakhage, Silvia Novohradská, Marc Thilo Figge, Kaswara Kraibooj, Hans-Martin Dahse, Falk Hillmann, Hanno Schoeler, Jakob Weber, Vito Valiante, Derek J Mattern Appl Microbiol Biotechnol . 2015 Dec;99(23):10151-61. doi: 10.1007/s00253-015-6898-1.
The opportunistic human pathogen Aspergillus fumigatus produces numerous different natural products. The genetic basis for the biosynthesis of a number of known metabolites has remained unknown. The gene cluster encoding for the biosynthesis of the conidia-bound metabolite trypacidin is of particular interest because of its antiprotozoal activity and possible role in the infection process. Here, we show that the genes encoding the biosynthesis enzymes of trypacidin reside within an orphan gene cluster in A. fumigatus. Genome mining identified tynC as an uncharacterized polyketide synthase with high similarity to known enzymes, whose products are structurally related to trypacidin including endocrocin and fumicycline. Gene deletion of tynC resulted in the complete absence of trypacidin production, which was fully restored when the mutant strain was complemented with the wild-type gene. When confronted with macrophages, the tynC deletion mutant conidia were more frequently phagocytosed than those of the parental wild-type strain. This was also found for phagocytic amoebae of the species Dictyostelium discoideum, which showed increased phagocytosis of ΔtynC conidia. Both macrophages and amoebae were also sensitive to trypacidin. Therefore, our results suggest that the conidium-bound trypacidin could have a protective function against phagocytes both in the environment and during the infection process.
2. Temperature during conidiation affects stress tolerance, pigmentation, and trypacidin accumulation in the conidia of the airborne pathogen Aspergillus fumigatus
Akira Watanabe, Kanae Sakai, Tohru Gonoi, Susumu Kawamoto, Naoki Kato, Toshihiko Nogawa, Hiroyuki Osada, Satoshi Suzuki, Katsuhiko Kamei, Daisuke Hagiwara, Myco Umemura PLoS One . 2017 May 9;12(5):e0177050. doi: 10.1371/journal.pone.0177050.
Asexual spores (conidia) are reproductive structures that play a crucial role in fungal distribution and survival. As fungal conidia are, in most cases, etiological agents of plant diseases and fungal lung disease, their stress resistance and interaction with their hosts have drawn increasing attention. In the present study, we investigated whether environmental temperature during conidiation affects the stress tolerance of the conidia of the human pathogenic fungus Aspergillus fumigatus. Conidia from a 25°C culture showed a lower tolerance to heat (60°C) and oxidative (H2O2) stresses and a marked resistance to ultraviolet radiation exposure, compared with those produced at 37 and 45°C. The accumulation of trehalose was lower in the conidia from the 25°C culture. Furthermore, the conidia from the 25°C culture showed darker pigmentation and increased transcripts of dihydroxynaphthalene (DHN)-melanin biosynthesis-related genes (i.e., pksP, arp1, and arp2). An RNA-sequencing analysis revealed that the transcription level of the trypacidin (tpc) gene cluster, which contains 13 genes, was sharply and coordinately activated in the conidia from the 25°C culture. Accordingly, trypacidin was abundant in the conidia from the 25°C culture, whereas there was little trypacidin in the conidia from the 37°C culture. Taken together, these data show that the environmental temperature during conidiation affects conidial properties such as stress tolerance, pigmentation, and mycotoxin accumulation. To enhance our knowledge, we further explored the temperature-dependent production of DHN-melanin and trypacidin in clinical A. fumigatus isolates. Some of the isolates showed temperature-independent production of DHN-melanin and/or trypacidin, indicating that the conidia-associated secondary metabolisms differed among the isolates.
3. Sulochrins and alkaloids from a fennel endophyte Aspergillus sp. FVL2
Ling Ding, Mohamed Shaaban, Mads Hartvig Clausen, Charlotte H Gotfredsen, Ahmed S Abdel-Razek, Viola Previtali, Hartmut Laatsch Nat Prod Res . 2021 Dec 6;1-11. doi: 10.1080/14786419.2021.2005054.
The fungal endophyteAspergillussp. strain FVL2, isolated from the traditional medicinal fennel plant,Foeniculum vulgare, was investigated for secondary metabolites. Fermentation on rice medium followed by chromatographic separation delivered three new natural products, 7-demethyl-neosulochrin (1), fumigaclavine I (3) andN-benzoyl-tryptophan (6) together with further 14 known metabolites, 1-O-methyl-sulochrin-4'-sulfate, questin, laccaic acid, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumitremorgin C, fumigaquinazoline C, tryptoquivaline J, trypacidin, 3'-O-demethyl-sulochrin, 1-O-methyl-sulochrin, protocatechuic acid, and vermelone. The chemical structures of the new metabolites were determined by NMR spectroscopy and ESI HR mass spectrometry. For fumigaclavine I, we observed the partial deuterium transfer from the solvent to the enol form with a remarkable high stereo selectivity. The discovery of the newseco-anthraquinone 7-demethyl-neosulochrin (1) revealed a second type of ring cleavage by a questin oxygenase. The discovery of diverse secondary metabolites broadens the chemical space ofAspergillus.
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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 ╳
