Echinosporin
(Synonyms: (-)-棘孢链菌素) 目录号 : GC47279
A bacterial metabolite with antibacterial and anticancer activities
Cas No.:79127-35-8
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
Echinosporin is a bacterial metabolite originally isolated from Streptomyces echinosporus that has antibacterial and anticancer activities.1,2,3 It is active against P. vulgaris, S. typhosa, S. sonnei, E. coli, and B. subtilis (MICs = 100, 100, 100, 200, and 400 µg/ml, respectively).1 Echinosporin induces cell cycle arrest at the G2/M phase and apoptosis in, as well as inhibits proliferation of, HCT-15 human colorectal cancer cells (IC50s = 1.7, 1.75, and 247 µM, respectively).2 It inhibits tumor growth in murine P388 leukemia and Meth 1 fibrosarcoma models when administered at doses ranging from 10 to 80 mg/kg.3
1.Sato, T., Kawamoto, I., Oka, T., et al.A new antibiotic echinosporin (XK-213) - producing organism, isolation and characterizationJ. Antibiot. (Tokyo)35(3)266-271(1982) 2.Cui, C.B., Liu, H.B., Gu, J.Y., et al.Echinosporins as new cell cycle inhibitors and apoptosis inducers from marine-derived Streptomyces albogriseolusFitoterapia78(3)238-240(2007) 3.Morimoto, M., and Imai, R.Antitumor activity of echinosporinJ. Antibiot. (Tokyo)38(4)490-495(1985)
| Cas No. | 79127-35-8 | SDF | |
| 别名 | (-)-棘孢链菌素 | ||
| Canonical SMILES | O[C@@]12[C@]3([H])[C@@](C=C2)([H])[C@H](OC1=O)OC(C(N)=O)=C3 | ||
| 分子式 | C10H9NO5 | 分子量 | 223.2 |
| 溶解度 | DMF: soluble,Methanol: soluble,Water: 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 | 4.4803 mL | 22.4014 mL | 44.8029 mL |
| 5 mM | 0.8961 mL | 4.4803 mL | 8.9606 mL |
| 10 mM | 0.448 mL | 2.2401 mL | 4.4803 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。
Antitumor activity of Echinosporin
J Antibiot (Tokyo) 1985 Apr;38(4):490-5.PMID:4008342DOI:10.7164/antibiotics.38.490.
Echinosporin isolated from a Streptomyces culture showed antitumor activity against rodent tumor models such as leukemia P388, P388/VCR, and fibrosarcoma Meth 1. It was marginally active against melanoma B16 and sarcoma 180. It was not active against Lewis lung carcinoma and xenograft MX-1. It inhibited the colony formation of HeLa S3 cells with a wide shoulder at low dose ranges. DNA, RNA, and protein synthesis were inhibited by Echinosporin. It depressed WBC with nadir on day 3, but the recovery to the normal level after Echinosporin injection was more rapid than that after mitomycin C.
Echinosporin antibiotics isolated from Amycolatopsis strain and their antifungal activity against root-rot pathogens of the Panax notoginseng
Folia Microbiol (Praha) 2019 Mar;64(2):171-175.PMID:30117099DOI:10.1007/s12223-018-0642-z.
Actinomycete strain YIM PH20520, isolated from the rhizosphere soil sample of Panax notoginseng collected in Wenshang, Yunnan Province, China, exhibited antifungal activity against root-rot pathogens of the Panax notoginseng. The structures of bioactive molecules, isolated from the ethyl acetate extract of the fermentation broth of the strain, were identified as Echinosporin (1) and 7-deoxyechinosporin (2) based on extensive spectroscopic analyses. 1 exhibited antifungal activity against four tested root-rot pathogens of Panax notoginseng include Fusarium oxysporum, Fusarium solani, Alternaria panax, and Phoma herbarum with the MIC value at 64, 64, 32, and 64 μg/mL, respectively. 2 exhibited antifungal activities against F. oxysporum, F. solani, A. panax, and P. herbarum with the MIC value at 128, 128, 64, and 128 μg/mL, respectively. Based on the phylogenetic analyses, the closest phylogenetic relative of strain YIM PH20520 is Amycolatopsis speibonae JS72T (97.69%), so strain YIM PH20520 was identified as Amycolatopsis strain. To the best of our knowledge, this is the first report of Echinosporin antibiotics isolated from Amycolatopsis strain besides Streptomyces strain and their antifungal activity against four tested root-rot pathogens of the Panax notoginseng. The results provide a reliable evidence for the following related biosynthetic investigations on Amycolatopsis strain YIM PH20520 due to echinosporins antibiotics' unique tricyclic acetal-lactone structures.
A new antibiotic Echinosporin (XK-213) - producing organism, isolation and characterization
J Antibiot (Tokyo) 1982 Mar;35(3):266-71.PMID:7076574DOI:10.7164/antibiotics.35.266.
Streptomyces echinosporus MK-213 produces a noval antibiotic Echinosporin (XK-213). Isolation of Echinosporin was performed by absorption on activated carbon under acidic conditions and then eluted by aqueous acetone. The compound crystallized from methanol is a water soluble white solid composed of C10H9NO5. Echinosporin exhibits weak antibacterial activities against Gram-positive and -negative microorganisms and its shows antitumor activity.
Oligomycins and pamamycin homologs impair motility and induce lysis of zoospores of the grapevine downy mildew pathogen, Plasmopara viticola
FEMS Microbiol Lett 2016 Aug;363(16):fnw167.PMID:27354061DOI:10.1093/femsle/fnw167.
Four antibiotics (pamamycin, oligomycin A, oligomycin B and Echinosporin) were isolated and characterized from the fermentation broth of the marine Streptomyces strains B8496 and B8739. Bioassays revealed that each of these compounds impaired motility and caused subsequent lysis of P. viticola zoospores in a dose- and time-dependent manner. Pamamycin displayed the strongest motility inhibitory and lytic activities (IC50 0.1 μg mL(-1)) followed by oligomycin B (IC50 0.15 and 0.2 μg mL(-1)) and oligomycin F (IC50 0.3 and 0.5 μg mL(-1)). Oligomycin A and Echinosporin also showed motility inhibitory activities against the zoospores with IC50 values of 3.0 and 10.0 μg mL(-1), respectively. This is the first report of motility inhibitory and lytic activities of these antibiotics against zoospores of a phytopathogenic peronosporomycete. Structures of all the isolated compounds were determined based on detailed spectroscopic analysis.
Echinosporins as new cell cycle inhibitors and apoptosis inducers from marine-derived Streptomyces albogriseolus
Fitoterapia 2007 Apr;78(3):238-40.PMID:17376609DOI:10.1016/j.fitote.2006.11.017.
Bioassay-guided fractionation of the ethyl acetate extract from the fermentation broth of marine-derived Streptomyces albogriseolus A2002 led to the isolation of Echinosporin (1) and 7-deoxyechinosporin (2). Compound 1 inhibited the proliferation of tsFT210, K562 and HCT-15 cancer cells (IC(50) 91.5 microM, 25.1 microM and 247 microM respectively) and 2 showed the same effect on K562 cells (IC(50) 143 microM). Flow cytometric analysis suggested that 1 and 2 exert their anti-proliferative effects on those cells through inhibiting cell cycle at the G(2)/M phase and inducing apoptosis.