Oosporein
(Synonyms: 卵孢霉素) 目录号 : GC47828
A mycotoxin with diverse biological activities
Cas No.:475-54-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oosporein is a mycotoxin that has been found in Beauveria and has diverse biological activities.1,2 It is cytotoxic to Sf9 and Sf21 insect cells with 50% cytotoxic concentration (CC50) values of 4.23 and 10.43 µM, respectively.3 Oosporin induces lethality in day-old cockerels (LD50 = 6.12 mg/kg).4 It inhibits Na+/K+-, Ca2+-, and Mg2+-ATPase activities by 27, 52, and 100%, respectively, in equine erythrocyte ghosts when used at a concentration of 200 µg/ml.2 Oosporein inhibits herpes simplex 1 (HSV-1), but not HeLa cell or E. coli, DNA polymerase (IC50s = 75, 610, and >700 µM, respectively).5 It is active against the bacterium S. pneumoniae (MIC = 32 µg/ml) and the plant pathogenic fungus P. infestans (MIC = 16 µM).1,6
1.Wainwright, M., Betts, R.P., and Teale, D.M.Antibiotic activity of oosporein from Verticillium psalliotaeTrans. Br. Mycol. Soc.86(1)168-170(1986) 2.Jeffs, L.B., and Khachatourians, G.G.Toxic properties of Beauveria pigments on erythrocyte membranesToxicon. 35(8)1351-1356(1997) 3.Arboleda Valencia, J.W., GaitÁn Bustamante, A.L., JimÉnez, A.V., et al.Cytotoxic activity of fungal metabolites from the pathogenic fungus Beauveria bassiana: An intraspecific evaluation of beauvericin productionCurr. Microbiol.63(3)306-312(2011) 4.Cole, R.J., Kirksey, J.W., Cutler, H.G., et al.Toxic effects of oosporein from Chaetomium trilateraleJ. Agric. Food Chem.22(3)517-520(1974) 5.Terry, B.J., Liu, W.C., Cianci, C.W., et al.Inhibition of herpes simplex virus type 1 DNA polymerase by the natural product oosporeinJ. Antibiot. (Tokyo)45(2)286-288(1992) 6.Nagaoka, T., Nakata, K., Kouno, K., et al.Antifungal activity of oosporein from an antagonistic fungus against Phytophthora infestansZ. Naturforsch. C. J. Biosci.59(3-4)302-304(2004)
| Cas No. | 475-54-7 | SDF | |
| 别名 | 卵孢霉素 | ||
| Canonical SMILES | CC1=C(O)C(C(C2=C(O)C(C(C)=C(O)C2=O)=O)=C(O)C1=O)=O | ||
| 分子式 | C14H10O8 | 分子量 | 306.2 |
| 溶解度 | DMSO : ≥ 50 mg/mL (163.28 mM) | 储存条件 | Store at -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 | 3.2658 mL | 16.3292 mL | 32.6584 mL |
| 5 mM | 0.6532 mL | 3.2658 mL | 6.5317 mL |
| 10 mM | 0.3266 mL | 1.6329 mL | 3.2658 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。
Oosporein Produced by Root Endophytic Chaetomium cupreum Promotes the Growth of Host Plant, Miscanthus sinensis, under Aluminum Stress at the Appropriate Concentration
Plants (Basel) 2022 Dec 21;12(1):36.PMID:36616165DOI:10.3390/plants12010036.
Chaetomium cupreum, a root endophyte in Miscanthus sinensis, enhances Al tolerance in M. sinensis by changing aluminum (Al) localization and the production of a siderophore, Oosporein, which chelates Al for detoxification. Oosporein has various functions, including insecticidal activity, phytotoxicity, antifungal activity, and a siderophore. In our study, we focused on the detoxification effect of Oosporein as a siderophore and on the growth of M. sinensis under Al exposure. In addition, the phytotoxicity of Oosporein to M. sinensis was confirmed to compare with those in Lactuca sativa and Oryza sativa as control plants. Under Al stress, Oosporein promoted plant growth in M. sinensis seedlings at 10 ppm, which was the same concentration as that detected in M. sinensis roots infected with C. cupreum in our previous study. Oosporein also showed low phytotoxicity to M. sinensis compared with L. sativa at even high concentrations of Oosporein. These results suggest that the concentration of Oosporein in M. sinensis roots would be maintained at the appropriate concentration to detoxify Al and would promote M. sinensis growth under Al stress, although Oosporein would show low phytotoxicity to the natural host plant, M. sinensis, compared with the non-host plant, L. sativa.
Transcription Factors BbPacC and Bbmsn2 Jointly Regulate Oosporein Production in Beauveria bassiana
Microbiol Spectr 2022 Dec 21;10(6):e0311822.PMID:36416546DOI:10.1128/spectrum.03118-22.
The entomopathogenic fungus Beauveria bassiana can produce the secondary metabolite Oosporein under alkaline conditions or in fungus-killed cadavers. However, the regulatory mechanism of Oosporein synthesis is not fully understood. In thisstudy, we found that the pH signaling transcription factor BbPacC is involved in the regulation of Oosporein production. Overexpression of BbPacC promotes Oosporein production in B. bassiana at pH 6.0 or under alkaline conditions (pH 8.0), but deletion of this gene abolished Oosporein production. Under acidic conditions (pH 4.0), no Oosporein production was observed in the wild-type and BbPacC overexpression strains. Yeast one-hybrid assays and electrophoretic mobility shift assay (EMSA) confirmed the binding ability of BbPacC with 4 putative PacC-binding sites in the promoter region of BbOpS3, a transcription factor located in the Oosporein synthetic gene cluster regulating the expression of Oosporein synthetic genes. Overexpression of Bbmsn2, a previously reported negative regulator of Oosporein synthesis, in OEPacC or wild-type strains abolished Oosporein production in all tested conditions. However, deletion of Bbmsn2 in the BbPacC overexpression strain significantly improved Oosporein production even at pH 4.0. These results indicated that BbPacC is a positive regulator of Oosporein production and functions jointly with Bbmsn2 to regulate Oosporein production in different environments and particularly under alkaline conditions. IMPORTANCE B. bassiana produces the red dibenzoquinone pigment Oosporein under certain specific conditions, such as alkaline conditions and fungus-killed cadavers. Ooporein possesses antibiotic and insect immune inhibition activities and plays multiple roles during the infection process of B. bassiana against insect hosts. Several negative regulators involved in Oosporein synthesis have been reported; however, we know little about the positive regulators outside the biosynthetic gene cluster. Here, we found that the pH signaling transcription factor BbPacC positively regulates Oosporein production by binding to several PacC-binding sites. In addition, our results also indicate that BbPacC jointly acts with the negative regulator Bbmsn2 to regulate Oosporein synthesis. Our results provide insight into understanding the regulatory mechanism of Oosporein production as well as targets to engineer B. bassiana strains producing high levels of Oosporein.
Oosporein, an abundant metabolite in Beauveria caledonica, with a feedback induction mechanism and a role in insect virulence
Fungal Biol 2019 Aug;123(8):601-610.PMID:31345414DOI:10.1016/j.funbio.2019.01.004.
Oosporein was first identified from the insect pathogen Beauveria bassiana >50 y ago. Here, we investigate the insecticidal, anti-feedant and immunomodulation effects of Oosporein produced by Beauveria caledonica on the forestry pest Hylobius abietis and model insect Galleria mellonella. We report a novel feedback induction mechanism regulating Oosporein production in B. caledonica; exogenous Oosporein induces the expression of the Oosporein cluster, leading to increased abundance of Oosporein biosynthetic enzymes, as shown by label-free quantitative proteomics. Oosporein did not have an anti-feedant effect on H. abietis adults - on the contrary, insects exposed to oosporein-treated food fed more than those exposed to untreated food only. Injected Oosporein did not kill insect larvae but increased susceptibility of H. abietis to a subsequent infection. Oosporein did not act as a contact toxin on H. abietis adults and G. mellonella larvae at the concentrations tested. Therefore, it appears that Oosporein promotes infection rather than directly killing insects; this could be mediated both by a reduction in haemocyte numbers and by alterations to the humoral immune system. This work makes a case for future research into the potential use of B. caledonica as a biocontrol agent through combinations with Oosporein or with enhanced production of Oosporein.
Oosporein from Tremella fuciformis
Acta Crystallogr Sect E Struct Rep Online 2012 Apr 1;68(Pt 4):o1231.PMID:22606165DOI:10.1107/S1600536812012950.
THE TITLE COMPOUND [SYSTEMATIC NAME: 3,3',6,6'-tetra-hydroxy-4,4'-dimethyl-1,1'-bi(cyclo-hexa-3,6-diene)-2,2',5,5'-tetra-one], C(14)H(10)O(8), was isolated from Tremella fuciformis. The mol-ecule has 2 symmetry, with the mid-point of the C-C bond linking the cyclo-hexa-dienedione rings located on a twofold rotation axis. In the mol-ecule, the ring is approximately planar, with an r.m.s. deviation of 0.0093 Å, and the two rings make a dihedral angle of 67.89 (5)°. Inter-molecular O-H⋯O hydrogen bonding occurs in the crystal structure.
Cytotoxic effects of Oosporein isolated from endophytic fungus Cochliobolus kusanoi
Front Microbiol 2015 Sep 1;6:870.PMID:26388840DOI:10.3389/fmicb.2015.00870.
In the present study, Oosporein, a fungal toxic secondary metabolite known to be a toxic agent causing chronic disorders in animals, was isolated from fungus Cochliobolus kusanoi of Nerium oleander L. Toxic effects of Oosporein and the possible mechanisms of cytotoxicity as well as the role of oxidative stress in cytotoxicity to Madin-Darby canine kidney kidney cells and RAW 264.7 splene cells were evaluated in vitro. Also to know the possible in vivo toxic effects of Oosporein on kidney and spleen, Balb/C mouse were treated with different concentrations of Oosporein ranging from 20 to 200 μM). After 24 h of exposure histopathological observations were made to know the effects of Oosporein on target organs. Oosporein induced elevated levels of reactive oxygen species (ROS) generation and high levels of malondialdehyde, loss of mitochondrial membrane potential, induced glutathione hydroxylase (GSH) production was observed in a dose depended manner. Effects Oosporein on chromosomal DNA damage was assessed by Comet assay, and increase in DNA damage were observed in both the studied cell lines by increasing the Oosporein concentration. Further, Oosporein treatment to studied cell lines indicated significant suppression of oxidative stress related gene (Superoxide dismutase1 and Catalase ) expression, and increased levels of mRNA expression in apoptosis or oxidative stress inducing genes HSP70, Caspase3, Caspase6, and Caspase9 as measured by quantitative real time-PCR assay. Histopathological examination of Oosporein treated mouse kidney and splenocytes further revealed that, Oosporein treated target mouse tissues were significantly damaged with that of untreated sam control mice and these effects were in directly proportional to the the toxin dose. Results of the present study reveals that, ROS is the principle event prompting increased Oosporein toxicity in studied in vivio and in vitro animal models. The high previlance of these fungi in temperate climates further warrants the need of safe food grain storage and processing practices to control the toxic effects of Oosporein to humans and live stock.