Streptimidone
(Synonyms: 链米酮) 目录号 : GC46228A bacterial metabolite with diverse biological activities
Cas No.:738-72-7
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
Streptimidone is a bacterial metabolite that has been found in Streptomyces and has diverse biological activities.1,2,3 It inhibits protein synthesis in a cell-free assay when used at a concentration of 50 μg/ml.2 Streptimidone (20 and 100 μg/disc) inhibits the growth of S. cerevisiae and the plant pathogenic fungus C. miyabeanus in a disc diffusion assay.1 It reduces tumor growth in H.S. No. 1 human sarcoma and H.Ep. No. 3 human epidermoid carcinoma rat xenograft models when administered at doses of 12.5 and 25 mg/kg per day.3
|1. Kondo, H., Oritani, T., and Kiyota, H. Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus. Eur. J. Org. Chem. (20), 3459-3462 (2000).|2. Bennett, L.L., Ward, V.L., and Brockman, R.W. Inhibition of protein synthesis in vitro by cycloheximide and related glutarimide antibiotics. Biochim. Biophys. Acta. 103(3), 478-485 (1965).|3. Teller, M.N. Antibiotics in experimental cancer chemotherapy. Trans. N. Y. Acad. Sc. 24, 158-166 (1961).
| Cas No. | 738-72-7 | SDF | |
| 别名 | 链米酮 | ||
| Canonical SMILES | O=C(CC(C[C@@H](O)CC([C@@H](C)/C=C(C)/C=C)=O)C1)NC1=O | ||
| 分子式 | C16H23NO4 | 分子量 | 293.4 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C, protect from light |
| 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 | 3.4083 mL | 17.0416 mL | 34.0832 mL |
| 5 mM | 0.6817 mL | 3.4083 mL | 6.8166 mL |
| 10 mM | 0.3408 mL | 1.7042 mL | 3.4083 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。
Isolation of new Streptimidone derivatives, glutarimide antibiotics from Streptomyces sp. W3002 using LC-MS-guided screening
J Antibiot (Tokyo) 2020 Mar;73(3):184-188.PMID:31853030DOI:10.1038/s41429-019-0264-y.
A LC-MS-guided screening led to the isolation of two new Streptimidone derivatives (2 and 3) containing a glutarimide ring and two glutarimide ring-opened compounds (4 and 5) along with a known glutarimide-containing polyketide, Streptimidone (1) from Streptomyces sp. W3002 strain. Their structures were elucidated by MS and NMR spectroscopic analyses and by comparison with data from the literature. Compound 2 is a non-hydroxylated analog at the C-5 position of Streptimidone. The structure of 3 was determined as a Streptimidone derivative possessing the α, β-unsaturated ketone moiety at positions C-5 and C-6. Compound 4 had similar chemical shifts and splitting patterns with 3, but the glutarimide ring is opened. Compound 5 closely resembles that of 4 with the only difference being the existence of an additional methoxy group instead of an amide group. Streptimidone (1) and 3 showed weak cytotoxic activity against three human cancer cell lines, respectively.
Chemical constituents from the Streptomyces morookaensis strain Sm4-1986
Nat Prod Res 2022 Jul;36(14):3681-3688.PMID:33538196DOI:10.1080/14786419.2021.1881095.
Three new compounds, including 6-methoxy-3,4,5,7-tetramethylisochromane-3,8-diol (1), 3,4,5,7-tetramethylisochromane-3,6,8-triol (2), Streptimidone derivative (3), along with ten known compounds (4-13) were isolated from the Streptomyces morookaensis strain Sm4-1986. Their chemical structures were established based on the information from UV, IR, NMR (1H NMR, 13C NMR, 1H-1H COSY, HSQC, HMBC, NOESY), and mass spectroscopic. Moreover, all the isolated new compounds were evaluated for antibacterial activities (S. aureus, B. cereus, S. epidermids and methicillin-resistant S. aureus) and their cytotoxicities against MCF-7, A549, Hela tumor cell lines and Marc-145 normal cell line.
A novel chresdihydrochalcone from Streptomyces chrestomyceticus exhibiting activity against Gram-positive bacteria
J Antibiot (Tokyo) 2020 Jul;73(7):429-434.PMID:32203125DOI:10.1038/s41429-020-0298-1.
Microbial-derived natural products provide unique bioactivities and serve as a unique source of drug leads. In the present study, we isolated one new chresdihydrochalcone (1), one new chresphenylacetone (2), and one known Streptimidone (3) from Streptomyces chrestomyceticus BCC 24770 using antibacterial activity-guided isolation and purification procedures. We determined their molecular weights using MS and HRMS and elucidated their chemical structures from their 1D and 2D NMR and electronic circular dichroism (ECD) spectra. Compound 1 showed moderate inhibitory activities against the Gram-positive bacteria Methicillin-resistant Staphylococcus aureus, Bacillus subtilis, and Micrococcus luteus. Cytotoxicity and hemolytic activity were not observed at a concentration of up to 100 μg ml-1. The specific antimicrobial activity and low toxicity of compound 1 indicate this compound to be a potential antibiotic candidate, especially as antibiotic resistance has become a significant public health threat.
Isolation, antifungal activity, and structure elucidation of the glutarimide antibiotic, Streptimidone, produced by Micromonospora coerulea
J Agric Food Chem 1999 Aug;47(8):3372-80.PMID:10552660DOI:10.1021/jf981259s.
The antibiotic Ao58A,which showed strong antifungal activity against some plant pathogenic fungi, was purified from the culture broth and mycelial mats of Micromonospora coerulea strain Ao58 using various chromatographic procedures. The molecular formula of the antibiotic Ao58A was deduced to be C(16)H(23)NO(4) (M + H, m/z 294.1707) by high-resolution FAB mass spectroscopy. Analyses of (1)H NMR, (13)C NMR, and 2D NMR spectral data revealed that the antibiotic Ao58A is the glutarimide antibiotic Streptimidone, 4-(2-hydroxy-5, 7-dimethyl-4-oxo-6,8-nonadienyl)-2,6-piperidinedione. The antibiotic Ao58A was very effective in inhibiting growth of Phytophthora capsici,Didymella bryoniae, Magnaporthe grisea, and Botrytis cinerea in the range approximately 3-10 microg mL(-)(1) of MICs. In vivo evaluation of the antibiotic Ao58A under greenhouse condition showed strong control efficacies against the development of P. capsici, B. cinerea, and M. grisea on pepper, cucumber, and rice plants, respectively. The antibiotic Ao58A was equally as effective as metalaxyl, vinclozolin, and tricyclazole in the control of these plant diseases. However, it did not show any phytotoxicity on the plants even when treated with 500 microg mL(-)(1).
Metabolomic variation in wild and cultured cordyceps and mycelia of Isaria cicadae
Biomed Chromatogr 2019 Apr;33(4):e4478.PMID:30578653DOI:10.1002/bmc.4478.
Isaria cicadae is one of the fungi used in traditional Chinese medicine with the longest tradition. It is used not only as a herbal medicine but also as a health food in Asia, together with cultured cordyceps and mycelia of the fungus used as substitute. However, the differences in their metabolite are unknown. Using a high-performance liquid chromatography-mass spectrometry (HPLC-MS)-based metabolomic method, we found that the fungus varies in its metabolism during growth on wild insects, artificially raised insects and artificial medium. There were 109 discriminatory metabolites detected in the samples by orthogonal projection to latent structure discriminant analysis and one-way ANOVA. High level of nonribosomal peptides (NRPs) only existed in the insect portions of the wild cordyceps (WI) and cultured cordyceps (CI), revealing that immunostimulation of the host insects enhanced the synthesis of NRPs in the fungus. The finding of a significantly higher level of sphingolipids in both the insect portions (WI, CI) and the coremia of the wild cordyceps (WC) and cultured cordyceps (CC) but not in cultured mycelia (CM) of I. cicadae implies that the immunostimulation of the live insects can induce the fungus to produce more sphingolipids, and this enhanced ability is probably heritable. Apart from NRPs and sphingolipids, the insect portions also contained higher levels of bioactive compounds such as lateritin, anisomycin, Streptimidone and ustiloxins. In contrast, the coremium groups (WC, CC) and CM contained 10-fold less NRP but much higher levels of sanative metabolites such as tocotrienol, 3'-deoxy-hanasanagin, γ-aminobutyric acid and phospholipids than the insect portions. The significantly higher content of antioxidants in WC, CC and CM than in WI and CI suggests that environmental oxygen has a significant effect on the metabolites. The temperature stress which the wild cordyceps encounters during growth is responsible for the relatively high content of trehalose. These findings indicate that the immunity of the host insect and growth environment have a strong impact on the metabolomic variation in Isaria cicadae. The variation in metabolites suggests differential utilization value for the insect portions, coremia and mycelia of the fungus.