Pellitorine
(Synonyms: 墙草碱) 目录号 : GC44590
An amide alkaloid with diverse biological activities
Cas No.:18836-52-7
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
| Cas No. | 18836-52-7 | SDF | |
| 别名 | 墙草碱 | ||
| Canonical SMILES | O=C(/C=C/C=C/CCCCC)NCC(C)C | ||
| 分子式 | C14H25NO | 分子量 | 223.4 |
| 溶解度 | 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 | 4.4763 mL | 22.3814 mL | 44.7628 mL |
| 5 mM | 0.8953 mL | 4.4763 mL | 8.9526 mL |
| 10 mM | 0.4476 mL | 2.2381 mL | 4.4763 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。
Pellitorine, an extract of Tetradium daniellii, is an antagonist of the ion channel TRPV1
Phytomedicine 2017 Oct 15;34:44-49.PMID:28899508DOI:10.1016/j.phymed.2017.06.006.
Background: Transient Receptor Potential Vanilloid 1 (TRPV1) confers noxious heat and inflammatory pain signals in the peripheral nervous system. Clinical trial of resiniferatoxin from Euphorbia species is successfully aimed at TRPV1 in cancer pain management and heading toward new selective painkiller status that further validates this target for drug discovery efforts. Evodia species, used in traditional medicine for hundreds of years, are a recognised source of different TRPV1 agonists, but no antagonist has yet been reported. Hypothesis/purpose: In a search for painkiller leads, we noted for the first time a TRPV1 antagonist activity in the fresh fruits of Tetradium daniellii (Benn.) T.G. Hartley (syn. Evodia hupehensis Dode). Methods: Through a combination of extraction and purification methods with functional TRPV1-specific Ca2+ uptake assays (bioactivity-guided fractionation/isolation/purification); we isolated a new painkiller candidate that is a distant structural homologue of capsiate exovanilloids and endovanilloids such as anandamide, but a putative competitive inhibitor of the TRPV1. Four additional inactive compounds (N-isobutyl-4,5-epoxy-2E-decadienamide, geranylpsoralen, 8-(7',8'-epoxygeranyloxy)psoralen, and xanthotoxol) were also co-purified with Pellitorine. Their structures were established by extensive 1D- and 2D-NMR spectroscopic analysis. Results: 1H- and 13C NMR determination of the chemical structure revealed it to be Pellitorine, (2E,4E)-N-(2-methylpropyl)deca-2,4-dienamide, which can compete structurally with algesics released in inflammation. In contrast to previous isolates from Evodia species, Pellitorine blocked capsaicin-evoked Ca2+ uptake with an IC50 of 154 µg/ml (0.69 mM/l). N-Isobutyl-4,5-epoxy-2E-decadienamide and geranylpsoralen, 8-(7',8'-epoxygeranyloxy)psoralen, and xanthotoxol did not affect the TRPV1. Conclusion: This is the first evidence that Pellitorine, an aliphatic alkylamide analogue of capsaicin, can serve as an antagonist of the TRPV1 and may inhibit exovanilloid-induced pain.
Quantitative transdermal behavior of Pellitorine from Anacyclus pyrethrum extract
Phytomedicine 2014 Dec 15;21(14):1801-7.PMID:25481393DOI:10.1016/j.phymed.2014.08.015.
The plant Anacyclus pyrethrum (AP) consists of several N-alkylamides with Pellitorine as main constituent. AP extracts are known to be biologically active and some products for topical administration containing AP plant extracts are already commercially available with functional cosmeceutical claims. However, no transdermal data for Pellitorine are currently available. Therefore, our general goal was to investigate the local skin pharmacokinetics of the plant N-alkylamide Pellitorine using a Franz diffusion cell set-up. Two different forms were applied on human skin: purified Pellitorine and the AP extract. Our study demonstrated that Pellitorine is able to cross the stratum corneum and the subsequent skin layers. A significantly higher permeability coefficient was observed when the AP extract (Kp=2.3 × 10(-4)cm/h) was administered, compared to purified Pellitorine (Kp=1.1 × 10(-4)cm/h). With the obtained Pellitorine concentrations in the skin layers and the receptor fluid, it is concluded that local and systemic effects can be expected after topical application. Due to these findings and as a regulatory consequence, products containing reasonable concentrations of Pellitorine are recommended to be classified as a medicinal product.
A systematic review on black pepper (Piper nigrum L.): from folk uses to pharmacological applications
Crit Rev Food Sci Nutr 2019;59(sup1):S210-S243.PMID:30740986DOI:10.1080/10408398.2019.1565489.
Considered as the "King of spices", black pepper (Piper nigrum L.) is a widely used spice which adds flavor of its own to dishes, and also enhances the taste of other ingredients. Piper nigrum has also been extensively explored for its biological properties and its bioactive phyto-compounds. There is, however, no updated compilation of these available data to provide a complete profile of the medicinal aspects of P. nigrum. This study endeavors to systematically review scientific data on the traditional uses, phytochemical composition, and pharmacological properties of P. nigrum. Information was obtained using a combination of keywords via recognized electronic databases (e.g., Science Direct and Google Scholar). Google search was also used. Books and online materials were also considered, and the literature search was restricted to the English language. The country with the highest number of traditional reports of P. nigrum for both human and veterinary medicine was India, mostly for menstrual and ear-nose-throat disorders in human and gastrointestinal disorders in livestock. The seeds and fruits were mostly used, and the preferred mode of preparation was in powdered form, pills or tablets, and paste. Piper nigrum and its bioactive compounds were also found to possess important pharmacological properties. Antimicrobial activity was recorded against a wide range of pathogens via inhibition of biofilm, bacterial efflux pumps, bacterial swarming, and swimming motilities. Studies also reported its antioxidant effects against a series of reactive oxygen and nitrogen species including the scavenging of superoxide anion, hydrogen peroxide, nitric oxide, DPPH, ABTS, and reducing effect against ferric and molybdenum (VI). Improvement of antioxidant enzymes in vivo has also been reported. Piper nigrum also exhibited anticancer effect against a number of cell lines from breast, colon, cervical, and prostate through different mechanisms including cytotoxicity, apoptosis, autophagy, and interference with signaling pathways. Its antidiabetic property has also been confirmed in vivo as well as hypolipidemic activity as evidenced by decrease in the level of cholesterol, triglycerides, and low-density lipoprotein and increase in high-density lipoprotein. Piper nigrum also has anti-inflammatory, analgesic, anticonvulsant, and neuroprotective effects. The major bioactive compound identified in P. nigrum is piperine although other compounds are also present including piperic acid, piperlonguminine, Pellitorine, piperolein B, piperamide, piperettine, and (-)-kusunokinin, which also showed biological potency. Most pharmacological studies were conducted in vitro (n = 60) while only 21 in vivo and 1 clinical trial were performed. Hence, more in vivo experiments using a pharmacokinetic and pharmacokinetic approach would be beneficial. As a conclusive remark, P. nigrum should not only be regarded as "King of spices" but can also be considered as part of the kingdom of medicinal agents, comprising a panoply of bioactive compounds with potential nutraceutical and pharmaceutical applications.
Pellitorine, a potential anti-cancer lead compound against HL6 and MCT-7 cell lines and microbial transformation of piperine from Piper Nigrum
Molecules 2010 Apr 5;15(4):2398-404.PMID:20428051DOI:10.3390/molecules15042398.
Pellitorine (1), which was isolated from the roots of Piper nigrum, showed strong cytotoxic activities against HL60 and MCT-7 cell lines. Microbial transformation of piperine (2) gave a new compound 5-[3,4-(methylenedioxy)phenyl]-pent-2-ene piperidine (3). Two other alkaloids were also found from Piper nigrum. They are (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (4) and 2,4-tetradecadienoic acid isobutyl amide (5). These compounds were isolated using chromatographic methods and their structures were elucidated using MS, IR and NMR techniques.
Antithrombotic activities of Pellitorine in vitro and in vivo
Fitoterapia 2013 Dec;91:1-8.PMID:23973654DOI:10.1016/j.fitote.2013.08.004.
Pellitorine (PLT), an active amide compound, is well known to possess insecticidal, antibacterial and anticancer properties. However, the anti-coagulant functions of PLT are not studied yet. Here, the anticoagulant activities of PLT were examined by monitoring activated partial thromboplastin time (aPTT), prothrombin time (PT), and the activities of cell-based thrombin and activated factor X (FXa). Furthermore, the effects of PLT on the expressions of plasminogen activator inhibitor type 1 (PAI-1) and tissue-type plasminogen activator (t-PA) were tested in tumor necrosis factor (TNF)-α activated human umbilical vein endothelial cells (HUVECs). Treatment with PLT resulted in prolonged aPTT and PT and inhibition of the activities of thrombin and FXa, and PLT inhibited production of thrombin and FXa in HUVECs. And PLT inhibited thrombin-catalyzed fibrin polymerization and platelet aggregation. In accordance with these anticoagulant activities, PLT elicited anticoagulant effects in mouse. In addition, treatment with PLT resulted in the inhibition of TNF-α-induced production of PAI-1 and in the significant reduction of the PAI-1 to t-PA ratio. Collectively, PLT possesses antithrombotic activities and offers bases for development of a novel anticoagulant.