Heronapyrrole B
(Synonyms: (+)-Heronapyrrole B) 目录号 : GC47426
A bacterial metabolite
Cas No.:1255704-24-5
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
Heronapyrrole B is a farnesylated 2-nitropyrrole bacterial metabolite that has been found in Streptomyces and has antibacterial activity.1,2 It is active against the Gram-positive bacteria S. aureus and B. subtilis (MICs = 1.8 and 7.5 µM, respectively) but not Gram-negative P. aeruginosa or E. coli.1
1.Raju, R., Piggott, A.M., Diaz, L.X.B., et al.Heronapyrroles A-C: farnesylated 2-nitropyrroles from an Australian marine-derived Streptomyces spOrg. Lett.12(22)5158-5161(2010) 2.Matsuo, T., Hashimoto, S., Nishikawa, K., et al.Total synthesis and complete stereochemical assignment of heronapyrroles A and BTetrahedron Letters565345-5348(2015)
| Cas No. | 1255704-24-5 | SDF | |
| 别名 | (+)-Heronapyrrole B | ||
| Canonical SMILES | CC(C)(O)[C@@H](O)CC/C(C)=C/CC[C@](C)(O)[C@H](O)CC1=CNC([N+]([O-])=O)=C1 | ||
| 分子式 | C19H32N2O6 | 分子量 | 384.5 |
| 溶解度 | 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 | 2.6008 mL | 13.0039 mL | 26.0078 mL |
| 5 mM | 0.5202 mL | 2.6008 mL | 5.2016 mL |
| 10 mM | 0.2601 mL | 1.3004 mL | 2.6008 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。
Inter-Kingdom beach warfare: Microbial chemical communication activates natural chemical defences
ISME J 2019 Jan;13(1):147-158.PMID:30116041DOI:10.1038/s41396-018-0265-z.
An inter-kingdom beach warfare between a Streptomyces sp. and Aspergillus sp. co-isolated from shallow water beach sand, collected off Heron Island, Queensland, Australia, saw the bacteriostatic Aspergillus metabolite cyclo-(L-Phe-trans-4-hydroxy-L-Pro) (3) stimulate the Streptomyces to produce nitric oxide (NO), which in turn mediated transcriptional activation of a silent biosynthetic gene cluster (BGC) for fungistatic Heronapyrrole B (1). Structure activity relationship studies, coupled with the use of NO synthase inhibitors, donors and scavangers, and both genomic and transcriptomic analyses, confirmed the extraordinary chemical cue specificity of 3, and its NO-mediated mechanism of transcriptional action. Our findings reveal the importance of inter-kingdom (fungal-bacterial) chemical communication in the regulation of silent BGCs coding for chemical defenses. We propose that the detection and characterisation of NO mediated transcriptional activation (NOMETA) of silent chemical defences in the environment, may inspire broader application in the field of microbial biodiscovery.
Reactivity of 2-Nitropyrrole Systems: Development of Improved Synthetic Approaches to Nitropyrrole Natural Products
J Org Chem 2018 Oct 19;83(20):12460-12470.PMID:30270625DOI:10.1021/acs.joc.8b01692.
Fundamental study of the reactivity of 2-nitropyrrole systems has enabled the identification of effective methods for incorporation of this unusual motif into advanced natural product frameworks. The presence of electron-rich pyrrole N-protecting groups (BOM, Boz) was demonstrated to enable a variety of previously unsuccessful palladium-mediated cross-couplings to be carried out in high yield. Based on this foundation, a series of regio- and stereoselective synthetic routes toward the nitropyrrolin and heronapyrrole families of natural products was developed by our group (G1-3). A full account of the strategic evolution of these approaches is reported here, highlighting the details of the setbacks encountered and eventual successes achieved en route, including the total synthesis of Heronapyrrole B. The fundamental studies and completed total syntheses provide general access to the bioactive 2-nitropyrrole natural product manifold and also establish practical and efficient methods for preparation and elaboration of the medicinally relevant 2-nitropyrrole motif.