Aspyrone
(Synonyms: (5S,6R)-5,6-二氢-5-羟基-6-甲基-3-[(2S,3S)-3-甲基环氧乙烷基]-2H-吡喃-2-酮) 目录号 : GC46886
A fungal metabolite with diverse biological activities
Cas No.:17398-00-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Aspyrone is a polyketide fungal metabolite that has been found in Aspergillus and has diverse biological activities.1,2 It is active against a panel of 13 fungi when used at a concentration of 20 µg/ml and a panel of 21 bacteria in a disc assay when used at a concentration of 100 µg per disc.1 Aspyrone (10-1,000 mg/L) is nematocidal against P. penetrans.2
1.Torres, M., Balcells, M., Sala, N., et al.Bactericidal and fungicidal activity of Aspergillus ochraceus metabolites and some derivativesPestic. Sci.53(1)9-14(1999) 2.Kimura, Y., Nakahara, S., and Fujioka, S.Aspyrone, a nematicidal compound isolated from the fungus, Aspergillus melleusBiosci. Biotech. Biochem.60(8)1375-1376(1996)
| Cas No. | 17398-00-4 | SDF | |
| 别名 | (5S,6R)-5,6-二氢-5-羟基-6-甲基-3-[(2S,3S)-3-甲基环氧乙烷基]-2H-吡喃-2-酮 | ||
| Canonical SMILES | C[C@H]([C@H](C=C1[C@H]2[C@H](C)O2)O)OC1=O | ||
| 分子式 | C9H12O4 | 分子量 | 184.2 |
| 溶解度 | Acetone: soluble,DMSO: 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 | 5.4289 mL | 27.1444 mL | 54.2888 mL |
| 5 mM | 1.0858 mL | 5.4289 mL | 10.8578 mL |
| 10 mM | 0.5429 mL | 2.7144 mL | 5.4289 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。
Circumdatin-Aspyrone Conjugates from the Coral-Associated Aspergillus ochraceus LCJ11-102
Mar Drugs 2019 Jul 6;17(7):400.PMID:31284571DOI:10.3390/md17070400.
Ochrazepines A-D (1-4), four new conjugates dimerized from 2-hydroxycircumdatin C (5) and Aspyrone (6) by a nucleophilic addition to epoxide, were isolated from the fermentation broth of the coral-associated Aspergillus ochraceus strain LCJ11-102. Their structures including absolute configurations were determined based on spectroscopic analysis and chemical methods. Compounds 1-4 were also obtained by the semisynthesis from a nucleophilic addition of 2-hydroxycircumdatin C (5) to Aspyrone (6). New compound 1 exhibited cytotoxic activity against 10 human cancer cell lines while new compounds 2 and 4 selectively inhibited U251 (human glioblastoma cell line) and compound 3 was active against A673 (human rhabdomyoma cell line), U87 (human glioblastoma cell line), and Hep3B (human liver cancer cell line) with IC50 (half maximal inhibitory concentration) values of 2.5-11.3 μM among 26 tested human cancer cell lines.
Chlorohydroaspyrones A and B, antibacterial Aspyrone derivatives from the marine-derived fungus Exophiala sp
J Nat Prod 2008 Aug;71(8):1458-60.PMID:18661951DOI:10.1021/np800107c.
Chlorohydroaspyrones A (1) and B (2), antibacterial Aspyrone derivatives, and the previously described Aspyrone (3), asperlactone (4), and penicillic acid (5) have been isolated from the broth of a marine isolate of the fungus Exophiala. The structure and absolute stereochemistry of the compounds were determined on the basis of the physicochemical data analysis and chemical reactions. Compounds 1 and 2 exhibited a mild antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The MIC values of each strain are as follows: compound 1 showed 62.5 microg/mL for S. aureus and 125 microg/mL for methicillin-resistant S. aureus and multidrug-resistant S. aureus, and compound 2, 62.5 microg/mL for S. aureus and methicillin-resistant S. aureus and 125 microg/mL for multidrug-resistant S. aureus.
Asperochratides A-J, Ten new polyketides from the deep-sea-derived Aspergillus ochraceus
Bioorg Chem 2020 Dec;105:104349.PMID:33074115DOI:10.1016/j.bioorg.2020.104349.
Ten new C9 polyketides (asperochratides A-J, 1-10) and 14 known miscellaneous compounds (11-24) were isolated from the deep-sea-derived fungus Aspergillus ochraceus. Structures of the new compounds were elucidated by extensive spectroscopic analyses, modified Mosher's method, Mo2(OAc)4 induced circular dichroism (ICD) experiments, and ECD calculations. Structurally, compounds 1-11 and 16-18 share the same polyketide origin of the skeleton and belong to Aspyrone co-metabolites. All isolates were tested for cytotoxic, anti-food allergic, anti-H1N1 virus, anti-microbe, and anti-inflammatory activities in vitro. Results showed that compounds 5-8 and 13-17 exerted significant cytotoxic effects on BV-2 cell line, and compound 16 showed the potential of anti-inflammatory activities.
Secondary Metabolites and Bioactivities of Aspergillus ochraceopetaliformis Isolated from Anthurium brownii
ACS Omega 2020 Aug 14;5(33):20991-20999.PMID:32875235DOI:10.1021/acsomega.0c02489.
Five new polyketides, asperochrapyran (1) and asperochralactones A-D (2-5), along with 12 known polyketides (6-17), were obtained from the fungal strain Aspergillus ochraceopetaliformis. Structures of all isolates were elucidated by their spectroscopic parameters. The relative configurations of the new compounds were deduced by the data of coupling constants and NOESY spectra. The absolute configurations were determined by the comparison of experimental and calculated ECD spectra. Moreover, the plausible biosynthesis pathway of major isolates was proposed as well. Anti-inflammatory activity of compounds 5 and 7-17 were evaluated with human neutrophils in response to the stimulation of formyl-methionyl-leucyl phenylalanine (fMLP). Asperlactone (9), Aspyrone (13), and (-)-(3R)-mellein (14) exerted superoxide anion inhibition at 30 ± 9%, 29 ± 9%, and 26 ± 12%, respectively, at 10 μM. The capacities of asperlactone (9), aspilactonol B (10), penicillic acid (12), and (-)-(3R)-mellein (14) in elastase release inhibition were revealed as 25 ± 4%, 38 ± 8%, 25 ± 5%, and 34 ± 9%, respectively, at 10 μM.
Development of an analytical method for identification of Aspergillus flavus based on chemical markers using HPLC-MS
Food Chem 2018 Feb 15;241:113-121.PMID:28958507DOI:10.1016/j.foodchem.2017.08.065.
Aspergillus flavus is a filamentous fungus found in nature and characterized by the production of bright and colourful colonies. It grows on different substrates, producing secondary metabolites and, if present in foodstuffs, can be a source of health problems for humans and animals, as well as causing economic losses. Traditional methods for fungal identification are based on morphological characteristics, requiring specialists and being very time-consuming. The development of analytical alternatives might have advantages such as greater efficiency, more reproducibility and be less time-consuming. Thus, a qualitative analytical method to detect Aspergillus flavus in food samples, based on the identification of fungal chemical markers by HPLC-MS, was developed. The method comprises methanol extraction followed by HPLC-MS analysis, and was able to identify 14 fungus secondary metabolites, namely aflatoxin B1, aflatoxin G1, aspergillic acid, Aspyrone, betaine, chrysogine, deacetyl parasiticolide A, flufuran, gregatin B, hydroxysydonic acid, nicotinic acid, phomaligin A, spinulosin and terrein.