Papyracillic Acid
目录号 : GC47871
A fungal metabolite
Cas No.:179308-49-7
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
Papyracillic acid is a fungal metabolite and a derivative of penicillic acid originally isolated from L. papyraceum and has antibiotic, antifungal, and phytotoxic activities.1,2 It is active against the bacteria X. campestris and B. subtilis and the fungus C. tropicalis in a disc assay when used at a concentration of 5 µg/disc.2 Papyracillic acid (1 mg/ml) induces necrotic lesion formation in a panel of 10 plants.
1.Shan, R., Anke, H., Stadler, M., et al.Papyracillic acid, a new penicillic acid analogue from the Ascomycete Lachnum papyraceumTetrahedron52(30)10249-10254(1996) 2.Evidente, A., Berestetskiy, A., Cimmino, A., et al.Papyracillic acid, a phytotoxic 1,6-dioxaspiro[4,4]nonene produced by Ascochyta agropyrina Var. nana, a potential mycoherbicide for Elytrigia repens biocontrolJ. Agric. Food Chem.57(23)11168-11173(2009)
| Cas No. | 179308-49-7 | SDF | |
| Canonical SMILES | C=C1C2(OC(C=C2OC)=O)OC(O)(C)C1C | ||
| 分子式 | C11H14O5 | 分子量 | 226.2 |
| 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。 |
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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 | 4.4209 mL | 22.1043 mL | 44.2087 mL |
| 5 mM | 0.8842 mL | 4.4209 mL | 8.8417 mL |
| 10 mM | 0.4421 mL | 2.2104 mL | 4.4209 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。
Papyracillic Acid, a phytotoxic 1,6-dioxaspiro[4,4]nonene produced by Ascochyta agropyrina Var. nana, a potential mycoherbicide for Elytrigia repens biocontrol
J Agric Food Chem 2009 Dec 9;57(23):11168-73.PMID:19891481DOI:10.1021/jf903499y.
A strain of Ascochyta agropyrina var. nana was isolated from Elytrigia repens (quack grass), a noxious perennial weed widespread through the cold regions of the northen and southern hemispheres. Papyracillic Acid was isolated for the first time from the fungal solid culture and identified using spectroscopic methods, including X-ray diffractometric and CD analysis for the assignment of the relative and absolute stereochemistries. Some key derivatives were prepared and used in a structure-activity relationship study. Tested by leaf disk-puncture assay, Papyracillic Acid at the concentration of 1 mg/mL was shown to be phytotoxic both for the host plant and a number of nonhost plants of the fungus. Papyracillic Acid was active against bacteria (Xanthomonas campestris and Bacillus subtilis) and the fungus Candida tropicalis at 6 microg/disk. Derivatives of Papyracillic Acid were significantly less active than original toxin. However, the monoacetyl derivative of the toxin did not possess antimicrobial activity but remained highly phytotoxic to quack grass. Hence, Papyracillic Acid and its analogues have potential as nonselective herbicides of natural origin. Some structure-activity relationship observations for Papyracillic Acid and its derivatives were also made.
Cyclopaldic acid, seiridin, and sphaeropsidin A as fungal phytotoxins, and larvicidal and biting deterrents against Aedes aegypti (Diptera: Culicidae): structure-activity relationships
Chem Biodivers 2013 Jul;10(7):1239-51.PMID:23847068DOI:10.1002/cbdv.201200358.
Aedes aegypti L. is the major vector of the arboviruses responsible for dengue fever, one of the most devastating human diseases. From a preliminary screening of fungal phytotoxins, cyclopaldic acid (1), seiridin (2), sphaeropsidin A (4), and Papyracillic Acid (5) were evaluated for their biting deterrent and larvicidal activities against Ae. aegypti L. Because compounds 1, 2, 4, and 5 exhibited mosquito biting deterrent activities and 1 and 4 demonstrated larvicidal activities, further structureactivity relationship studies were initiated on these toxins. In biting-deterrence bioassays, 1, 2, 4, and 5, 3,8-didansylhydrazone of cyclopaldic acid, 1F, 5-azidopentanoate of cyclopaldic acid A, 1G, the reduced derivative of cyclopaldic acid, 1 H, isoseiridin (3), 2'-O-acetylseiridin (2A), 2'-oxoseiridin (2C), 6-O-acetylsphaeropsidin A (4A), 8,14-methylensphaeropsidin A methyl ester (4B), and sphaeropsidin B (4C) showed activities higher than the solvent control. Sphaeropsidin B (4C) was the most active compound followed by 2A, while the other compounds were less active. Biting-deterrence activity of compound 4C was statistically similar to DEET. In the larvicidal screening bioassays, only compounds 1 and 4 demonstrated larvicidal activities. Based on LD50 values, compound 4 (LD50 36.8 ppm) was significantly more active than compound 1 (LD50 58.2 ppm). However, the activity of these compounds was significantly lower than permethrin.
Human pancreatic cancer cells under nutrient deprivation are vulnerable to redox system inhibition
J Biol Chem 2020 Dec 4;295(49):16678-16690.PMID:32978257DOI:10.1074/jbc.RA120.013893.
Large regions in tumor tissues, particularly pancreatic cancer, are hypoxic and nutrient-deprived because of unregulated cell growth and insufficient vascular supply. Certain cancer cells, such as those inside a tumor, can tolerate these severe conditions and survive for prolonged periods. We hypothesized that small molecular agents, which can preferentially reduce cancer cell survival under nutrient-deprived conditions, could function as anticancer drugs. In this study, we constructed a high-throughput screening system to identify such small molecules and screened chemical libraries and microbial culture extracts. We were able to determine that some small molecular compounds, such as penicillic acid, Papyracillic Acid, and auranofin, exhibit preferential cytotoxicity to human pancreatic cancer cells under nutrient-deprived compared with nutrient-sufficient conditions. Further analysis revealed that these compounds target to redox systems such as GSH and thioredoxin and induce accumulation of reactive oxygen species in nutrient-deprived cancer cells, potentially contributing to apoptosis under nutrient-deprived conditions. Nutrient-deficient cancer cells are often deficient in GSH; thus, they are susceptible to redox system inhibitors. Targeting redox systems might be an attractive therapeutic strategy under nutrient-deprived conditions of the tumor microenvironment.
Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction
J Org Chem 2012 Oct 19;77(20):9171-8.PMID:23013246DOI:10.1021/jo3017617.
A synthetic approach to the Papyracillic Acid family of natural products has been developed. The spiroacetal core is rapidly assembled through an unprecedented zinc carbenoid-mediated tandem chain extension-acylation reaction. Subsequent functional group manipulation provided access to Papyracillic Acid B and 4-epi-papyracillic acid C. The successful preparation of these molecules resulted in the clarification of structural assignments of members of this family of natural products.
In Vitro and In Vivo Toxicity Evaluation of Natural Products with Potential Applications as Biopesticides
Toxins (Basel) 2021 Nov 15;13(11):805.PMID:34822589DOI:10.3390/toxins13110805.
The use of natural products in agriculture as pesticides has been strongly advocated. However, it is necessary to assess their toxicity to ensure their safe use. In the present study, mammalian cell lines and fish models of the zebrafish (Danio rerio) and medaka (Oryzias latipes) have been used to investigate the toxic effects of ten natural products which have potential applications as biopesticides. The fungal metabolites cavoxin, epi-epoformin, Papyracillic Acid, seiridin and sphaeropsidone, together with the plant compounds inuloxins A and C and ungeremine, showed no toxic effects in mammalian cells and zebrafish embryos. Conversely, cyclopaldic and α-costic acids, produced by Seiridium cupressi and Dittrichia viscosa, respectively, caused significant mortality in zebrafish and medaka embryos as a result of yolk coagulation. However, both compounds showed little effect in zebrafish or mammalian cell lines in culture, thus highlighting the importance of the fish embryotoxicity test in the assessment of environmental impact. Given the embryotoxicity of α-costic acid and cyclopaldic acid, their use as biopesticides is not recommended. Further ecotoxicological studies are needed to evaluate the potential applications of the other compounds.