Pyrenocine A
目录号 : GC48014
A fungal metabolite with diverse biological activities
Cas No.:76868-97-8
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Pyrenocine A is a fungal metabolite that has been found in P. terrestris and has diverse biological activities.1 It inhibits the asexual spore germination of the plant pathogenic fungi F. oxysporum, F. solani, M. hiemalis, and R. stolonifer (EC50s = 14, 20, 20, and 25 µg/ml, respectively). Pyrenocine A is active against B. subtilis, S. aureus, and E. coli (IC50s = 30, 45, and 200 µg/ml, respectively). It inhibits onion seedling elongation (EC50 = 4 µg/ml). Pyrenocine A is also a phytotoxin that inhibits lettuce seed germination and rice seedling elongation.2,3
1.Sparace, S.A., Reeleder, R.D., and Khanizadeh, S.Antibiotic activity of the pyrenocinesCan. J. Microbiol.33(4)327-330(1987) 2.Sato, H., Konoma, K., and Sakamura, S.Phytotoxins produced by onion pink root fungus, Pyrenochaeta terrestrisAgric. BioI. Chem.43(11)2409-2411(1979) 3.Sato, H., Konoma, K., Sakamura, S., et al.X-Ray crystal structure of pyrenocine A, a phytotoxin from Pyrenochaeta terrestrisAgric. BioI. Chem.45(3)795-797(1981)
| Cas No. | 76868-97-8 | SDF | |
| Canonical SMILES | O=C1OC(C)=C(C(/C=C/C)=O)C(OC)=C1 | ||
| 分子式 | C11H12O4 | 分子量 | 208.2 |
| 溶解度 | Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.8031 mL | 24.0154 mL | 48.0307 mL |
| 5 mM | 0.9606 mL | 4.8031 mL | 9.6061 mL |
| 10 mM | 0.4803 mL | 2.4015 mL | 4.8031 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。
Pyrenocine A induces monopolar spindle formation and suppresses proliferation of cancer cells
Bioorg Med Chem 2019 Dec 1;27(23):115149.PMID:31679979DOI:10.1016/j.bmc.2019.115149.
Pyrenocine A, a phytotoxin, was found to exhibit cytotoxicity against cancer cells with an IC50 value of 2.6-12.9 μM. Live cell imaging analysis revealed that Pyrenocine A arrested HeLa cells at the M phase with characteristic ring-shaped chromosomes. Furthermore, as a result of immunofluorescence staining analysis, we found that Pyrenocine A resulted in the formation of monopolar spindles in HeLa cells. Monopolar spindles are known to be induced by inhibitors of the kinesin motor protein Eg5 such as monastrol and STLC. Monastrol and STLC induce monopolar spindle formation and M phase arrest via inhibition of the ATPase activity of Eg5. Interestingly, our data revealed that Pyrenocine A had no effect on the ATPase activity of Eg5 in vitro, which suggested the compound induces a monopolar spindle by an unknown mechanism. Structure-activity relationship analysis indicates that the enone structure of Pyrenocine A is likely to be important for its cytotoxicity. An alkyne-tagged analog of Pyrenocine A was synthesized and suppressed proliferation of HeLa cells with an IC50 value of 2.3 μM. We concluded that Pyrenocine A induced monopolar spindle formation by a novel mechanism other than direct inhibition of Eg5 motor activity, and the activity of Pyrenocine A may suggest a new anticancer mechanism.
Potent anti-inflammatory activity of Pyrenocine A isolated from the marine-derived fungus Penicillium paxilli Ma(G)K
Mediators Inflamm 2014;2014:767061.PMID:24574582DOI:10.1155/2014/767061.
Very little is known about the immunomodulatory potential of secondary metabolites isolated from marine microorganisms. In the present study, we characterized Pyrenocine A, which is produced by the marine-derived fungus Penicillium paxilli Ma(G)K and possesses anti-inflammatory activity. Pyrenocine A was able to suppress, both pretreatment and posttreatment, the LPS-induced activation of macrophages via the inhibition of nitrite production and the synthesis of inflammatory cytokines and PGE2. Pyrenocine A also exhibited anti-inflammatory effects on the expression of receptors directly related to cell migration (Mac-1) as well as costimulatory molecules involved in lymphocyte activation (B7.1). Nitrite production was inhibited by Pyrenocine A in macrophages stimulated with CpG but not Poly I:C, suggesting that Pyrenocine A acts through the MyD88-dependent intracellular signaling pathway. Moreover, Pyrenocine A is also able to inhibit the expression of genes related to NF κ B-mediated signal transduction on macrophages stimulated by LPS. Our results indicate that Pyrenocine A has promissory anti-inflammatory properties and additional experiments are necessary to confirm this finding in vivo model.
2-Oxaspiro[4.5]decane and α-pyrenocine derivatives from the endophytic fungus Roussoella sp. PSU-H51
Nat Prod Res 2022 Oct;36(19):4911-4920.PMID:33853446DOI:10.1080/14786419.2021.1910692.
One new 2-oxaspiro[4.5]decane, roussoellide, and one new α-pyrenocine, 2',3'-dihydropyrenocine A, together with nine known compounds including known arthropsolide A, and pyrenocines A and E, were obtained from the culture broth of the endophytic fungus Roussoella sp. Their structures were determined using spectroscopic data. The absolute configuration of known arthropsolide A was assigned on the basis of X-ray diffraction data using Cu Kα radiation. Known Pyrenocine A displayed weak cytotoxic activity against breast cancer (MCF-7) cells with an IC50 value of 27.1µM and weak antifungal activity against Microsporum gypseum SH-MU-4 with an MIC value of 615.2µM.[Formula: see text].
Pathogenicity and Pyrenocine Production of Curvularia inaequalis Isolated from Zoysia Grass
Plant Dis 2000 Jun;84(6):684-688.PMID:30841112DOI:10.1094/PDIS.2000.84.6.684.
Five isolates of Curvularia inaequalis were obtained from blighted leaves of zoysia grass. The optimal growth temperature of the pathogen was 30°C and all isolates caused foliar blighting symptoms on zoysia grass, bent grass, and bermuda grass. Phytotoxic substances were associated with pathogenicity. Two phytotoxins were isolated from liquid cultures of C. inaequalis by ethyl acetate extraction and repeated silica gel column chromatography. On the basis of mass and nuclear magnetic resonance spectral analyses, the compounds were identified as pyrenocines A and B, phytotoxins produced by Pyrenochaeta terrestris. Pyrenocine A caused leaf necrosis in a leaf-wounding bioassay and inhibited growth of all plants tested in a whole plant test. Large crab grass and fall panicum were most susceptible to Pyrenocine A. Pyrenocines A and B also caused significant electrolyte leakage from leaf tissues of bermuda grass. Pyrenocine B exhibited much weaker phytotoxic activity than Pyrenocine A in all bioassays performed. Both compounds caused leaf tip dieback symptoms in turf grass plants similar to symptoms observed in the field. Thus, pyrenocines A and B are thought to be involved in the development of Curvularia blight disease of turfgrasses caused by C. inaequalis.
Antibiotic activity of the pyrenocines
Can J Microbiol 1987 Apr;33(4):327-30.PMID:3594310DOI:10.1139/m87-055.
Pyrenocine A, a phytotoxin produced by Pyrenochaeta terrestris (Hansen) Gorenz, Walker and Larson, possesses general antibiotic activity against plants, fungi, and bacteria. Effective doses for 50% inhibition (ED50s) are 4 micrograms/mL for onion seedling elongation; 14, 20, 20, and 25 micrograms/mL for the germination of asexual spores of Fusarium oxysporum f. sp. cepae, Fusarium solani f. sp. pisi, Mucor hiemalis, and Rhizopus stolonifer, respectively. Pyrenocine A also inhibits the linear mycelial growth of both P. terrestris and F. oxysporum with ED50s calculated as 77 and 54 micrograms/mL, respectively. Gram-positive bacteria are more susceptible to Pyrenocine A than Gram-negative bacteria. ED50s are estimated as 30, 45, and 200 micrograms/mL for the inhibition of growth of Bacillus subtilis, Staphylococcus aureus, and Escherichia coli, respectively, with Pseudomonas aeruginosa resistant to those concentrations tested. Pyrenocine A acts primarily as a biostatic rather than a biocidal agent with all organisms tested showing some degree of recovery when released from Pyrenocine A. Pyrenocines B and C show little antibiotic activity in the bioassays performed.