Phomalactone
(Synonyms: (+)-Phomalactone) 目录号 : GC45810
A fungal metabolite
Cas No.:28921-94-0
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
Phomalactone is a fungal metabolite that has been found in N. sphaerica and has fungicidal activity.1,2 It is active against strains of the plant pathogenic fungi C. sasaki, P. graminicola, M. griesea, P. capsica, and P. infestans (IC50s = 200, 120, 83, 120, and 0.83 mg/L, respectively), but not F. oxysporum, A. alternate, B. cinerea, or C. gloeosporioides (IC50s = >200 mg/L for all).1 Phomalactone is also active against the plant pathogenic fungi A. niger and O. minus (MICs = 62.5 and 125 μg/ml, respectively).2
|1. Kim, J.-C., Choi, G.J., Park, J.-H., et al. Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Manag. Sci. 57(6), 554-559 (2001).|2. Wu, S.-H., Chen, Y.-W., Shao, S.-C., et al. Two new solanapyrone analogues from the endophytic fungus Nigrospora sp. YB-141 of Azadirachta indica. Chem. Biodivers. 6(1), 79-85 (2009).
| Cas No. | 28921-94-0 | SDF | |
| 别名 | (+)-Phomalactone | ||
| Canonical SMILES | O=C1C=C[C@H](O)[C@H](/C=C/C)O1 | ||
| 分子式 | C8H10O3 | 分子量 | 154.2 |
| 溶解度 | Dichloromethane: soluble,DMSO: soluble,Ethanol: 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 | 6.4851 mL | 32.4254 mL | 64.8508 mL |
| 5 mM | 1.297 mL | 6.4851 mL | 12.9702 mL |
| 10 mM | 0.6485 mL | 3.2425 mL | 6.4851 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。
Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves
J Chem Ecol 2015 Jul;41(7):602-12.PMID:26133676DOI:10.1007/s10886-015-0602-x.
Zinnia elegans Jacq. plants are infected by a fungus that causes dark red spots with necrosis on leaves, particularly in late spring to the middle of summer in the Mid-South of the United States. This fungal disease causes the leaves to wilt and eventually kills the plant. The fungus was isolated, cultured in potato dextrose broth, and identified as Nigrospora sphaerica by molecular techniques. Two major lactone metabolites (Phomalactone and catenioblin A) were isolated from liquid culture of N. sphaerica isolated from Z. elegans. When injected into leaves of Z. elegans, Phomalactone caused lesions similar to those of the fungus. The lesion sizes were proportional to the concentration of the Phomalactone. Phomalactone, but not catenioblin A, was phytotoxic to Z. elegans and other plant species by inhibition of seedling growth and by causing electrolyte leakage from photosynthetic tissues of both Z. elegans leaves and cucumber cotyledons. This latter effect may be related to the wilting caused by the fungus in mature Z. elegans plants. Phomalactone was moderately fungicidal to Coletotrichum fragariae and two Phomopsis species, indicating that the compound may keep certain other fungi from encroaching into plant tissue that N. sphaerica has infected. Production of large amounts of Phomalactone by N. sphaerica contributes to the pathogenic behavior of this fungus, and may have other ecological functions in the interaction of N. sphaerica with other fungi. This is the first report of isolation of catenioblin A from a plant pathogenic fungus. The function of catenioblin A is unclear, as it was neither significantly phyto- nor fungitoxic.
Phomalactone optimization and production of entomopathogenic fungi by Ophiocordyceps communis BCC 1842 and BCC 2763
Prep Biochem Biotechnol 2016;46(1):44-8.PMID:25285781DOI:10.1080/10826068.2014.970691.
Phomalactone, an antibacterial, insecticidal, and herbicidal compound, was produced by insect pathogenic fungi, Ophiocordyceps communis BCC 1842 and BCC 2763, in bioreactors using different carbon and nitrogen sources. Glucose and fructose were preferable for growth and Phomalactone production. The highest specific growth rate (μ) of 0.012 hr(-1), the highest biomass yield (Ysx) of 0.38 g DW g(-1) sugar, the highest volumetric sugar consumption rate (qs) of 0.036 g (L hr)(-1), the maximum Phomalactone concentration ([Formula: see text]) of 93.30 mg L(-1) at 127 hr, and the highest volumetric production rate of Phomalactone (qp) of 0.46 ± 0.12 mg (L d)(-1) were obtained on glucose and sodium nitrate as the sole carbon and nitrogen sources, respectively, by O. communis BCC 1842. In contrast, O. communis BCC 2763 gave lower Phomalactone production. This mass Phomalactone production is useful for the biological synthesis of a precursor for more broad-range potent analogs such as antitumor, antifungal, and others and for its further biological studies.
Antimicrobial metabolite profiling of Nigrospora sphaerica from Adiantum philippense L
J Genet Eng Biotechnol 2020 Oct 22;18(1):66.PMID:33094373DOI:10.1186/s43141-020-00080-4.
Background: Endophyte bestows beneficial aspects to its inhabiting host, along with a contribution to diverse structural attributes with biological potential. In this regard, antimicrobial profiling of fungal endophytes from medicinal plant Adiantum philippense revealed bioactive Nigrospora sphaerica from the leaf segment. Chemical and biological profiling through TLC-bioautography and hyphenated spectroscopic techniques confirmed the presence of Phomalactone as an antimicrobial metabolite. Results: The chemical investigation of the broth extract by bioassay-guided fractionation confirmed Phomalactone as a bioactive antimicrobial secondary metabolite. The antimicrobial activity of Phomalactone was found to be highest against Escherichia coli by disc diffusion assay. The MIC was found to be significant against both Escherichia coli and Xanthomonas campestris in the case of bacteria and dermatophyte Candida albicans at 150 μg/ml, respectively. Conclusions: Overall, the results highlighted the antimicrobial potential of Phomalactone from the endophyte Nigrospora sphaerica exhibiting a broad spectrum of antimicrobial activity against human and phytopathogenic bacteria and fungi. This work is the first report regarding the antibacterial activity of Phomalactone.
Identification of the antibiotic Phomalactone from the entomopathogenic fungusHirsutella thompsonii var.synnematosa
J Chem Ecol 1994 Feb;20(2):293-302.PMID:24242054DOI:10.1007/BF02064437.
Dichloromethane extracts of culture broth from three strains of the entomopathogenic fungusHirsutella thompsonii var.synnematosa were toxic to two species of tephritid fruit fly and inhibited conidial germination in vitro in several other entomopathogenic fungi includingBeauveria bassiana, Tolypocladium spp., andMetarhizium anisopliae. A major metabolite, toxic to apple maggot,Rhagoletis pomonella, and inhibitory to conidial germination inB. bassiana, was isolated and identified as the antibiotic (+)-phomalactone, 6-(1-propenyl)-5,-6-dihydro-5-hydroxypyran-2-one. This is the first biologically active compound of low molecular weight isolated from the genusHirsutella.
Activity against plant pathogenic fungi of Phomalactone isolated from Nigrospora sphaerica
Pest Manag Sci 2001 Jun;57(6):554-9.PMID:11407033DOI:10.1002/ps.318.
Phomalactone, 5,6-dihydro-5-hydroxy-6-prop-2-enyl-2H-pyran-2-one, produced by the fungus Nigrospora sphaerica, was tested in vitro against nine plant pathogenic fungi, and specifically inhibited the mycelial growth of Phytophthora infestans, with an MIC value of 2.5 mg litre-1. Its inhibitory activities against sporangium and zoospore germination of P infestans were similar to those against Phytophthora capsici. In vivo, at 100 and 500 mg litre-1, it reduced the development of tomato late blight caused by P infestans.