Sporothriolide
目录号 : GC48097A fungal metabolite with fungicidal and plant growth regulatory activities
Cas No.:154799-92-5
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
Sporothriolide is a fungal metabolite that has been found in Sporothrix.1 It is active against the plant pathogenic fungi U. violacea, M. microspore, and E. repens, and the alga C. fusca, but not the bacteria B. megaterium and E. coli, when used at a concentration of 10 mg/ml. Sporothriolide inhibits mycelial growth of the plant pathogenic fungus R. solani (EC50 = 3.04 µg/ml) and protects against R. solani-induced rice sheath blight on rice plants when used at a concentration of 200 µg/ml.2 It also prevents necrosis induced by the plant pathogenic fungus B. cinerea in pepper seedlings at 500 ppm.1 Sporothriolide (4 mg/ml) prevents germination of L. sativum and M. sativa seedlings.
1.Krohn, K., Ludewig, K., Aust, H.-J., et al.Biologically active metabolites from fungi. 3. sporothriolide, discosiolide, and 4-epi-ethisolide--new furofurandiones from Sporothrix sp., Discosia sp., and Pezicula lividaJ. Antibiot. (Tokyo)47(1)113-118(1994) 2.Cao, L.-L., Zhang, Y.-Y., Liu, Y.-J., et al.Anti-phytopathogenic activity of sporothriolide, a metabolite from endophyte Nodulisporium sp. A21 in Ginkgo bilobaPestic. Biochem. Physiol.1297-13(2016)
| Cas No. | 154799-92-5 | SDF | |
| Canonical SMILES | CCCCCC[C@H]([C@@](OC1=O)([H])[C@]2([H])C1=C)OC2=O | ||
| 分子式 | C13H18O4 | 分子量 | 238.3 |
| 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 | 4.1964 mL | 20.982 mL | 41.9639 mL |
| 5 mM | 0.8393 mL | 4.1964 mL | 8.3928 mL |
| 10 mM | 0.4196 mL | 2.0982 mL | 4.1964 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。
Seven-Step Total Synthesis of Sporothriolide
J Org Chem 2021 Sep 3;86(17):12475-12479.PMID:34423986DOI:10.1021/acs.joc.1c01663.
An enantioselective total synthesis of Sporothriolide, a bioactive furofurandione-type fungal metabolite, has been achieved in a 21% overall yield from a commercially available β,γ-unsaturated carboxylic acid via seven steps. The key steps of this synthesis include a highly diastereoselective Michael addition of a chiral oxazolidinone derivative to a nitro olefin, the exploitation of an aromatic ring as a masked carboxylic acid functionality, and the base-promoted elimination of nitrous acid to install the α-methylene lactone unit of Sporothriolide in the final step.
Sporothriolide derivatives as chemotaxonomic markers for Hypoxylon monticulosum
Mycology 2014 Jul 3;5(3):110-119.PMID:25379335DOI:10.1080/21501203.2014.929600.
During the course of a screening for novel anti-infective agents from cultures of tropical Xylariaceae originating from French Guiana and Thailand, pronounced antifungal activity was noted in extracts of cultures of Hypoxylon monticulosum. A bioassay-guided fractionation led to the known metabolite Sporothriolide as active principle. In addition, three new derivatives of Sporothriolide were isolated, for which we propose the trivial names sporothric acid, isosporothric acid and dihydroisosporothric acid. Their chemical structures were elucidated by high-resolution electrospray mass spectrometry in conjunction with two-dimensional nuclear magnetic resonance (2D-NMR) spectroscopy. From earlier studies on the biogenesis of the chemically similar canadensolides, we postulate that the new compounds were shunt products, rather than biogenetic precursors of Sporothriolide. Interestingly, this compound class, as well as strong antifungal activities, was only observed in multiple cultures of H. monticulosum, but not in several hundreds of Hypoxylon cultures studied previously or concurrently. Therefore, Sporothriolide production may constitute a species-specific feature with respect to Hypoxylon and the Xylariaceae, although the compound was previously reported from non-related fungal taxa.
Sporothriolide-Related Compounds from the Fungus Hypoxylon monticulosum CLL-205 Isolated from a Sphaerocladina Sponge from the Tahiti Coast
J Nat Prod 2017 Oct 27;80(10):2850-2854.PMID:29043802DOI:10.1021/acs.jnatprod.7b00714.
Two sporothriolide-related compounds were obtained from an extract of the fungus Hypoxylon monticulosum CLL-205, isolated from a Sphaerocladina sponge collected from the Tahiti coast. Compound 2 is a deoxy analogue of sporothric acid (4). Compound 3 is a newly reported unusual scaffold combining Sporothriolide (1) and trienylfuranol A (5) moieties, through a Diels-Alderase-type reaction. Various experimental and analytical arguments supported the biocatalytic origin of compound 3. The structures of the isolated compounds were elucidated using 1D and 2D NMR, HRMS, and IR data. The structure and the absolute configuration of 3 were unambiguously confirmed by a single-crystal X-ray diffraction analysis.
Anti-phytopathogenic activity of Sporothriolide, a metabolite from endophyte Nodulisporium sp. A21 in Ginkgo biloba
Pestic Biochem Physiol 2016 May;129:7-13.PMID:27017876DOI:10.1016/j.pestbp.2015.10.002.
Phytopathogenic fungi such as Rhizoctonia solani and Sclerotinia sclerotiorum caused multiple plant diseases resulting in severe loss of crop production. Increasing documents endorsed that endophytes are a striking resource pool for numerous metabolites with various bioactivities such as anti-fungal. Here we reported the characterization and anti-phytopathogenic activity of Sporothriolide, a metabolite produced by Nodulisporium sp. A21-an endophytic fungus in the leaves of Ginkgo biloba. Among the total twenty-five endophytic fungi isolated from the healthy leaves of G. biloba, the fermentation broth (FB) of the strain A21 was found potently inhibitory activity against R. solani and S. sclerotiorum using mycelia growth inhibition method. A21 was then identified as Nodulisporium sp., the asexual stage of Hypoxylon sp., by microscopic examination and ITS rDNA sequence data comparison. Under the bioassay-guided fractionation, Sporothriolide was isolated from the petroleum ether extract of the FB of A21, whose structure was established by integrated interpretation of HR-ESI-MS and (1)H- and (13)C-NMR. Furthermore, the crystal structure of Sporothriolide was first reported. In addition, Sporothriolide was validated to be potently antifungal against R. solani, S. sclerotiorum and inhibit conidium germination of Magnaporthe oryzae in vitro and in vivo, indicating that it could be used as a lead compound for new fungicide development.
The sporothriolides. A new biosynthetic family of fungal secondary metabolites
Chem Sci 2020 Oct 21;11(46):12477-12484.PMID:34123230DOI:10.1039/d0sc04886k.
The biosynthetic gene cluster of the antifungal metabolite Sporothriolide 1 was identified from three producing ascomycetes: Hypomontagnella monticulosa MUCL 54604, H. spongiphila CLL 205 and H. submonticulosa DAOMC 242471. A transformation protocol was established, and genes encoding a fatty acid synthase subunit and a citrate synthase were simultaneously knocked out which led to loss of Sporothriolide and sporochartine production. In vitro reactions showed that the sporochartines are derived from non-enzymatic Diels-Alder cycloaddition of 1 and trienylfuranol A 7 during the fermentation and extraction process. Heterologous expression of the spo genes in Aspergillus oryzae then led to the production of intermediates and shunts and delineation of a new fungal biosynthetic pathway originating in fatty acid biosynthesis. Finally, a hydrolase was revealed by in vitro studies likely contributing towards self-resistance of the producer organism.