Paraherquamide E
(Synonyms: 对郝喹酰胺E) 目录号 : GC44564
A fungal metabolite
Cas No.:125600-53-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Paraherquamide E is a fungal metabolite originally isolated from P. charlesii with anthelmintic and insecticidal activities. It is lethal to C. elegans (LD50 = 6 μg/ml). Paraherquamide E is also lethal to O. fasciatus (LD50 = 0.089 μg/nymph). Oral administration of paraherquamide E (0.5-4 mg/kg) reduces T. colubriformis fecal egg count in gerbils.
| Cas No. | 125600-53-5 | SDF | |
| 别名 | 对郝喹酰胺E | ||
| Canonical SMILES | CC(C=CO1)(C)OC2=C1C(NC([C@]34C[C@](CN(CC[C@@H]5C)[C@]5(C6=O)C7)(N6C)[C@]7([H])C3(C)C)=O)=C4C=C2 | ||
| 分子式 | C28H35N3O4 | 分子量 | 477.6 |
| 溶解度 | Soluble in DMSO | 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 | 2.0938 mL | 10.469 mL | 20.938 mL |
| 5 mM | 0.4188 mL | 2.0938 mL | 4.1876 mL |
| 10 mM | 0.2094 mL | 1.0469 mL | 2.0938 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。
Paraherquamide E
Acta Crystallogr Sect E Struct Rep Online 2010 Aug 11;66(Pt 9):o2227.PMID:21588597DOI:10.1107/S1600536810030795.
In the title compound, C(28)H(35)N(3)O(4), also known as 14-de-oxy-paraherquamide A,the two pyrrolidine rings adopt envelope conformations. The piperazine ring of the diaza-bicyclo-[2.2.2]octan-3-one unit adopts a boat conformation whereas the two piperidine rings are in distorted boat conformations. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, the mol-ecules are linked into chains along the b axis by inter-molecular N-H⋯O hydrogen bonds.
Studies on Paraherquamide Biosynthesis: Synthesis of Deuterium-Labeled 7-Hydroxy-Pre-Paraherquamide, a Putative Precursor of Paraherquamides A, E & F
Tetrahedron 2009 Apr 18;65(16):3246-3260.PMID:20161298DOI:10.1016/j.tet.2008.08.102.
The stereocontrolled, asymmetric synthesis of triply deuterium-labeled 7-hydroxy-pre-paraherquamide (27) was accomplished, employing a diastereoselective intramolecular S(N)2' cyclization strategy. The deuterium-labeled substrate was interrogated in a precursor incorporation experiment in the paraherquamide-producing organism Penicillium fellutanum. The isolated sample of paraherquamide A revealed incorporation of one of the two geminal deuterons of the CD(2)-group at C-12 exclusively. The lack of signals for the second deuteron of the CD(2)-group at C-12 and for the CH(2)D-group (C-22/C-23) suggests that this substrate suffered an unexpectedly selective catabolic degradation and metabolic re-incorporation of deuterium thus casting doubt on the proposed biosynthetic intermediacy of 27. Consideration of alternative biosynthetic pathways, including oxidation of the indole C-6 position prior to hydroxylation at C-7 or oxidative spiro-contraction of pre-paraherquamide prior to construction of the dioxepin is discussed. The synthesis of 27 also provides for a concise, asymmetric stereocontrolled synthesis of an advanced intermediate that will be potentially useful in the synthesis of Paraherquamide E & F.
Insecticidal activity of Paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae
J Agric Food Chem 2006 Apr 19;54(8):2921-5.PMID:16608209DOI:10.1021/jf0530998.
Paraherquamide H (1) and paraherquamide I (2), two new compounds of the paraherquamide (PHQ) family, together with the already known paraherquamide A (3), paraherquamide B (4), Paraherquamide E (5), VM55596 (N-oxide paraherquamide) (6), paraherquamide VM55597 (7), and five known diketopiperazines (8-12) have been isolated from the culture broth of Penicillium cluniae Quintanilla. The structure of 1 and 2, on the basis of NMR and MS analysis, was established. It is worth noticing that, in both cases, an unusual oxidative substitution in C-16 was found, which had only previously been detected in PHQ 7. Isolated compounds were tested for insecticidal activity against the hemipteran Oncopeltus fasciatus Dallas. Mortality data have allowed preliminary structure activity relationships to be proposed. The most potent product was 5 with a LD(50) of 0.089 microg/nymph.
Identification of Therapeutic Targets in an Emerging Gastrointestinal Pathogen Campylobacter ureolyticus and Possible Intervention through Natural Products
Antibiotics (Basel) 2022 May 18;11(5):680.PMID:35625323DOI:10.3390/antibiotics11050680.
Campylobacter ureolyticus is a Gram-negative, anaerobic, non-spore-forming bacteria that causes gastrointestinal infections. Being the most prevalent cause of bacterial enteritis globally, infection by this bacterium is linked with significant morbidity and mortality in children and immunocompromised patients. No information on pan-therapeutic drug targets for this species is available yet. In the current study, a pan-genome analysis was performed on 13 strains of C. ureolyticus to prioritize potent drug targets from the identified core genome. In total, 26 druggable proteins were identified using subtractive genomics. To the best of the authors' knowledge, this is the first report on the mining of drug targets in C. ureolyticus. UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) was selected as a promiscuous pharmacological target for virtual screening of two bacterial-derived natural product libraries, i.e., postbiotics (n = 78) and streptomycin (n = 737) compounds. LpxC inhibitors from the ZINC database (n = 142 compounds) were also studied with reference to LpxC of C. ureolyticus. The top three docked compounds from each library (including ZINC26844580, ZINC13474902, ZINC13474878, Notoginsenoside St-4, Asiaticoside F, Paraherquamide E, Phytoene, Lycopene, and Sparsomycin) were selected based on their binding energies and validated using molecular dynamics simulations. To help identify potential risks associated with the selected compounds, ADMET profiling was also performed and most of the compounds were considered safe. Our findings may serve as baseline information for laboratory studies leading to the discovery of drugs for use against C. ureolyticus infections.
Itaconic acid derivatives and diketopiperazine from the marine-derived fungus Aspergillus aculeatus CRI322-03
Phytochemistry 2011 Jun;72(8):816-20.PMID:21397285DOI:10.1016/j.phytochem.2011.02.013.
Three metabolites, pre-aurantiamine (1), (-)-9-hydroxyhexylitaconic acid (4) and (-)-9-hydroxyhexylitaconic acid-4-methyl ester (5), together with two known compounds, Paraherquamide E (6) and secalonic acid D (7), were isolated from the marine-derived fungus, Aspergillus aculeatus.