Avenaciolide
(Synonyms: (±)-Avenaciolide) 目录号 : GC40677
A fungal metabolite
Cas No.:26057-70-5
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
Avenaciolide is a water-insoluble fungal metabolite originally isolated from A. avenaceus. It inhibits glutamate transport in isolated rat liver mitochondria (Ki = 8 μM).
| Cas No. | 26057-70-5 | SDF | |
| 别名 | (±)-Avenaciolide | ||
| Canonical SMILES | O=C(C1=C)O[C@@]2([H])[C@]1([H])[C@H](CCCCCCCC)OC2=O | ||
| 分子式 | C15H22O4 | 分子量 | 266.3 |
| 溶解度 | Soluble in DMSO | 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 | 3.7552 mL | 18.7758 mL | 37.5516 mL |
| 5 mM | 0.751 mL | 3.7552 mL | 7.5103 mL |
| 10 mM | 0.3755 mL | 1.8776 mL | 3.7552 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。
Avenaciolide Induces Apoptosis in Human Malignant Meningioma Cells through the Production of Reactive Oxygen Species
Biol Pharm Bull 2022;45(4):517-521.PMID:35370277DOI:10.1248/bpb.b21-01039.
Malignant meningioma has a poor prognosis and there are currently no effective therapies. Avenaciolide is water-insoluble natural organic product produced by Aspergillus avenaceus G. Smith that can inhibit mitochondrial function. In the present study, we investigated the anti-cancer effects of Avenaciolide in an isolated human malignant meningioma cell line, HKBMM. In addition, to assess the specificity of Avenaciolide, its effects on normal human neonatal dermal fibroblast HDFn cells were also examined. Avenaciolide showed effective anti-cancer activity, and its cytotoxicity in HKBMM cells was greater than that in HDFn cells. The anti-cancer effects of Avenaciolide were mediated by reactive oxygen species (ROS)-induced apoptosis, which may have been caused by mitochondrial disfunction. These results suggest that Avenaciolide has potential as a therapeutic drug for malignant meningioma.
The actions of Avenaciolide and ethanol on glucose metabolism and on related enzyme activities in the isolated perfused rat liver
Biochim Biophys Acta 1976 Jun 23;437(1):51-61.PMID:949510DOI:10.1016/0304-4165(76)90346-9.
1. The metabolic response of livers to perfusion with ethanol with and without Avenaciolide, has been followed by measuring the perfusate levels of glucose, lactate, pyruvate, beta-hydroxybutyrate, ethanol, amino acids, urea and lipid. 2. Analysis of the perfused livers showed changes in the activities of some of the key enzymes of glycolysis, gluconeogenesis and lipogenesis. Ethanol perfusion decreased the levels of phosphofructokinase, glucokinase and cytosolic isocitrate dehydrogenase, while Avenaciolide lowered pyruvate carboxylase and phosphoenolpyruvate carboxykinase as well as glucokinase. Isocitrate dehydrogenase and phosphofructokinase were unchanged, but the ionophore increased the level of fructose-1,6-diphosphatase. Ethanol plus Avenaciolide showed the same pattern as ethanol alone, together with the decrease in phosphoenolpyruvate carboxykinase found with Avenaciolide. 3. Neither ethanol nor Avenaciolide had any effect on kexokinase, pyruvate kinase or acetyl-CoA carboxylase. There were small changes in glucose-6-phosphatase and malic enzyme, and a tendency for citrate lyase levels to decline in Avenaciolide perfusions.
Isolation of (-)-avenaciolide as the antifungal and antimycobacterial constituent of a Seimatosporium sp. Endophyte from the medicinal plant Hypericum perforatum
Nat Prod Commun 2014 Oct;9(10):1495-6.PMID:25522544doi
An extract of Seimatosporium sp., an endophyte from the Canadian medicinal plant Hypericum perforatum, exhibited significant antifungal and antimycobacterial activity against Candida albicans and Mycobacterium tuberculosis H37Ra. Bioassay guided fractionation led to the isolation of (-)-avenaciolide as the only bioactive constituent of the extract. This is the first report of both the antimycobacterial activity of Avenaciolide and its isolation from a Seimatosporium sp. fungus.
Synthesis and antifungal activity of aromatic bis-gamma-lactones analogous to Avenaciolide
Chem Biodivers 2007 Dec;4(12):2745-54.PMID:18081084DOI:10.1002/cbdv.200790223.
Avenaciolide is a bis-gamma-lactone isolated from Aspergillus avenaceus and possesses antifungal activity. Here, we describe the total syntheses and characterization by elemental analyses, and IR and NMR spectroscopy of three new bis-gamma-lactones analogous to Avenaciolide, where the octyl group of the natural product was replaced by aromatic groups. The effects of the Avenaciolide, the novel compounds, and their synthetic precursors on the mycelia development and conidia germination of Colletotrichum gloeosporioides were evaluated in vitro. The new compounds were as active as Avenaciolide in the tested conditions, while the synthetic precursors were inactive. The preparation and characterization of 15 new synthetic intermediates are also described.
Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic Avenaciolide analogue
Pest Manag Sci 2009 Jan;65(1):34-40.PMID:18785221DOI:10.1002/ps.1640.
Background: Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antifungal activity, a bis-gamma-lactone analogous to Avenaciolide was prepared and characterized by elemental analysis, mass spectrometry, and infrared and NMR spectroscopy. Results: The absolute structures of this compound and of the synthetic precursor (also a bis-gamma-lactone) were determined by X-ray diffraction analysis. The bis-gamma-lactones synthesized crystallize in the orthorhombic space group P2(1)2(1)2(1), and the crystal packings are supported by C--H...O hydrogen bonds. The compound showed antifungal activity against Colletotrichum gloeosporioides (Penz.) Penz. & Sacc., while the synthetic precursor was inactive under the in vitro test conditions employed. Conclusion: The results indicate that it is not only the bis-gamma-lactone skeleton that is important to antifungal activity. The latter also depends on the presence of the exocyclic double bond possibly due to a Michael addition type reaction with the fungal enzymes.