Trypacidin
目录号 : GC48711
A fungal metabolite
Cas No.:1900-29-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Trypacidin is a fungal metabolite originally isolated from A. fumigatus.1 It is active against B. subtilis and M. bovis (MICs = 12.5 and 1.25 µg/ml, respectively), as well as T. cruzi and T. gondii (MICs = 5-10 and 10-20 µg/ml, respectively).1,2 It reduces viability and induces lysis of A549 human lung cancer cells (IC50s = 7.4 µM for both).3 Trypacidin increases survival in a mouse model of T. gondii infection when administered in six doses of 12.5 mg/kg each.1
1.Balan, J., Ebringer, L., Nemec, P., et al.Antiprotozoal antibiotics. II. Isolation and characterization of trypacidin, a new antibiotic, active against Trypanosoma cruzi and Toxoplasma gondiiJ. Antibiot. (Tokyo)16157-160(1963) 2.Song, Z., Liu, Y., Gao, J., et al.Antitubercular metabolites from the marine-derived fungus strain Aspergillus fumigatus MF029Nat. Prod. Res.1-8(2019) 3.Gauthier, T., Wang, X., Dos Santos, J.S., et al.Trypacidin, a spore-borne toxin from Aspergillus fumigatus, is cytotoxic to lung cellsPLoS One7(2)e29906(2012)
| Cas No. | 1900-29-4 | SDF | |
| Canonical SMILES | O=C1C2(C(C(OC)=O)=CC(C=C2OC)=O)OC3=CC(C)=CC(OC)=C13 | ||
| 分子式 | C18H16O7 | 分子量 | 344.3 |
| 溶解度 | 储存条件 | -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9044 mL | 14.5222 mL | 29.0444 mL |
| 5 mM | 0.5809 mL | 2.9044 mL | 5.8089 mL |
| 10 mM | 0.2904 mL | 1.4522 mL | 2.9044 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Trypacidin, a spore-borne toxin from Aspergillus fumigatus, is cytotoxic to lung cells
PLoS One 2012;7(2):e29906.PMID:22319557DOI:10.1371/journal.pone.0029906.
Inhalation of Aspergillus fumigatus conidia can cause severe aspergillosis in immunosuppressed people. A. fumigatus produces a large number of secondary metabolites, some of which are airborne by conidia and whose toxicity to the respiratory tract has not been investigated. We found that spores of A. fumigatus contain five main compounds, tryptoquivaline F, fumiquinazoline C, questin, monomethylsulochrin and Trypacidin. Fractionation of culture extracts using RP-HPLC and LC-MS showed that samples containing questin, monomethylsulochrin and Trypacidin were toxic to the human A549 lung cell line. These compounds were purified and their structure verified using NMR in order to compare their toxicity against A549 cells. Trypacidin was the most toxic, decreasing cell viability and triggering cell lysis, both effects occurring at an IC₅₀ close to 7 µM. Trypacidin toxicity was also observed in the same concentration range on human bronchial epithelial cells. In the first hour of exposure, Trypacidin initiates the intracellular formation of nitric oxide (NO) and hydrogen peroxide (H₂O₂). This oxidative stress triggers necrotic cell death in the following 24 h. The apoptosis pathway, moreover, was not involved in the cell death process as Trypacidin did not induce apoptotic bodies or a decrease in mitochondrial membrane potential. This is the first time that the toxicity of Trypacidin to lung cells has been reported.
Antagonistic activity and mode of action of Trypacidin from marine-derived Aspergillus fumigatus against Vibrio parahaemolyticus
3 Biotech 2022 Jun;12(6):131.PMID:PMC9123130DOI:10.1007/s13205-022-03194-3.
This study aimed to investigate the antagonistic activity and mode of action of Trypacidin from marine-derived Aspergillus fumigatus against Vibrio parahaemolyticus. Results indicated that the minimal inhibitory concentration and minimal bactericidal concentration of Trypacidin against V. parahaemolyticus were 31.25 and 62.5 μg/mL, respectively, which was better than that of streptomycin sulfate. Trypacidin remarkably inhibited the growth of V. parahaemolyticus and had a strong destructive effect on cell wall permeability and integrity, cell membrane permeability, and morphological alterations. Its potential as an antibacterial agent for aquatic products must be further explored.
Identification of the antiphagocytic Trypacidin gene cluster in the human-pathogenic fungus Aspergillus fumigatus
Appl Microbiol Biotechnol 2015 Dec;99(23):10151-61.PMID:26278536DOI: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.
Temperature during conidiation affects stress tolerance, pigmentation, and Trypacidin accumulation in the conidia of the airborne pathogen Aspergillus fumigatus
PLoS One 2017 May 9;12(5):e0177050.PMID:28486558DOI: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.
Antitubercular metabolites from the marine-derived fungus strain Aspergillus fumigatus MF029
Nat Prod Res 2021 Aug;35(16):2647-2654.PMID:34414849DOI:10.1080/14786419.2019.1660331.
During the systematic screening of bioactive compounds from our marine natural product library, crude extract of the marine-derived fungus strain Aspergillus fumigatus MF029 exhibited moderate bioactivities against Bacillus subtilis, Staphylococcus aureus, methicillin-resistant S. aureus, and Mycobacterium bovis bacillus Calmette-Guérin (BCG). Further chemical investigation resulted in the identification of two new compounds, chaetominine A (1) and sphingofungin I (2), together with four known compounds, emodin (3), chaetominine (4), sphingofungin D (5) and Trypacidin (6). Trypacidin displayed potential antitubercular activity with MIC value of 1.25 μg/mL.