Hordenine
(Synonyms: 大麦芽碱; Ordenina; Peyocactine) 目录号 : GC38434
An Analytical Reference Standard
Cas No.:539-15-1
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
Hordenine is a naturally occurring alkaloid found in a variety of plants, most commonly germinated barley (Hordeum species) from which the name is derived, and is structurally classified as a phenethylamine.1,2 It is biosynthesized by the step-wise double methylation of tyramine .3 Hordenine binds to and activates the dopamine D2 receptor (Ki = 13 ?M) but antagonizes D2 receptor β-arrestin recruitment.4 It inhibits tyrosinase activity and expression at concentrations ≥ 50 ?M resulting in reduced melanin accumulation in human melanocytes.2 Hordenine is present in significant amounts in beer and can be measured in serum in the free form, for up to 2 hours, and the glucuronidated form, for up to 6 hours, after beer consumption.5 This product is intended for research and forensic applications.
1.Liu, D.L., and Lovett, J.V.Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicalsJ. Chem. Ecol.19(10)2231-2244(1993) 2.Kim, S.-C., Lee, J.-H., Kim, M.-H., et al.Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytesFood Chem.141(1)174-181(2013) 3.Meyer, E.Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgarePlant Cell Rep.1(6)236-239(1982) 4.Sommer, T., Hübner, H., El Kerdawy, A., et al.Identification of the beer component hordenine as food-derived dopamine D2 receptor agonist by virtual screening a 3D compound databaseSci. Rep.744201(2017) 5.Steiner, I., Brauers, G., Temme, O., et al.A sensitive method for the determination of hordenine in human serum by ESI? UPLC-MS/MS for forensic toxicological applicationsAnal. Bioanal. Chem.408(9)2285-2292(2016)
| Cas No. | 539-15-1 | SDF | |
| 别名 | 大麦芽碱; Ordenina; Peyocactine | ||
| Canonical SMILES | OC1=CC=C(CCN(C)C)C=C1 | ||
| 分子式 | C10H15NO | 分子量 | 165.23 |
| 溶解度 | DMSO: 250 mg/mL (1513.04 mM) | 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 | 6.0522 mL | 30.2608 mL | 60.5217 mL |
| 5 mM | 1.2104 mL | 6.0522 mL | 12.1043 mL |
| 10 mM | 0.6052 mL | 3.0261 mL | 6.0522 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。
Quorum sensing inhibition of Hordenine analogs on Pseudomonas aeruginosa and Serratia marcescens
Synth Syst Biotechnol 2021 Nov 1;6(4):360-368.PMID:34786511DOI:10.1016/j.synbio.2021.09.010.
Quorum sensing (QS) plays an essential role in virulence factor production, biofilm formation, and antimicrobial resistance. As a potent QS inhibitor, Hordenine can inhibit both QS and biofilm formation in Pseudomonas aeruginosa and Serratia marcescens. In this work, we tested the QS inhibitory potential of 27 Hordenine analogs against QS and biofilm formation in P. aeruginosa and S. marcescens. Among the tested analogs, seven (12, 28, 27, 26, 2, 23, and 7) exhibited strong QS inhibitory activity against P. aeruginosa, five of which (12, 28, 27, 26, and 2) showed better inhibitory activity than Hordenine. In addition, seven analogs (28, 12, 23, 7, 26, 2, and 27) exhibited better biofilm inhibition against P. aeruginosa than Hordenine. Four analogs (7, 28, 2, and 12) showed QS inhibitory activity against S. marcescens, two of which (7 and 28) demonstrated better inhibitory activity than Hordenine. Furthermore, analog 7 showed similar biofilm inhibition against S. marcescens as Hordenine. Structure-activity relationship (SAR) analysis indicated that the inhibitory activities of the analogs were related to four factors, i.e., carbon chain length, presence or absence of an α,β-C[bond, double bond]C bond, amino group with/without lipophilic group, such as methyl group, and hydroxyl group in benzene ring.
Beneficial Effects of Hordenine on a Model of Ulcerative Colitis
Molecules 2023 Mar 21;28(6):2834.PMID:36985809DOI:10.3390/molecules28062834.
Hordenine, a phenethylamine alkaloid, is found in a variety of plants and exhibits a broad array of biological activities and pharmacological properties, including anti-inflammatory and anti-fibrotic effects. However, the efficacy and underlying mechanisms of Hordenine in treating ulcerative colitis (UC) remain unclear. To address this, we examined the therapeutic effects of Hordenine on dextran sodium sulphate (DSS)-induced UC by comparing disease activity index (DAI), colon length, secretion of inflammatory factors, and degree of colonic histological lesions across diseased mice that were and were not treated with Hordenine. We found that Hordenine significantly reduced DAI and levels of pro-inflammatory factors, including interleukin (IL)-6, IL-1β, and tumor necrosis factor alpha (TNF-α), and also alleviated colon tissue oedema, colonic lesions, inflammatory cells infiltration and decreased the number of goblet cells. Moreover, in vitro experiments showed that Hordenine protected intestinal epithelial barrier function by increasing the expression of tight junction proteins including ZO-1 and occludin, while also promoting the healing of intestinal mucosa. Using immunohistochemistry and western blotting, we demonstrated that Hordenine reduced the expression of sphingosine kinase 1 (SPHK1), sphingosine-1-phosphate receptor 1 (S1PR1), and ras-related C3 botulinum toxin substrate 1 (Rac1), and it inhibited the expression of phosphorylated signal transducer and activator of transcription 3 (p-STAT3) in colon tissues. Thus, Hordenine appears to be effective in UC treatment owing to pharmacological mechanisms that favor mucosal healing and the inhibition of SPHK-1/S1PR1/STAT3 signaling.
Hordenine: A Novel Quorum Sensing Inhibitor and Antibiofilm Agent against Pseudomonas aeruginosa
J Agric Food Chem 2018 Feb 21;66(7):1620-1628.PMID:29353476DOI:10.1021/acs.jafc.7b05035.
The quorum sensing (QS) inhibitory activity of Hordenine from sprouting barley against foodborne pathogen Pseudomonas aeruginosa was evaluated for the first time here. At concentrations ranging from 0.5 to 1.0 mg mL-1, Hordenine inhibited the levels of acyl-homoserine lactones. The enhanced susceptibility of Hordenine with netilmicin on P. aeruginosa PAO1 biofilm formation as well as their efficiency in disrupting preformed biofilms was also evaluated using scanning electron microscopy and confocal laser scanning microscopy (CLSM). Hordenine treatment inhibited the production of QS-related extracellular virulence factors of P. aeruginosa PAO1. Additionally, quantitative real-time polymerase chain reaction analysis demonstrated that the expressions of QS-related genes, lasI, lasR, rhlI, and rhlR, were significantly suppressed. Our results indicated that Hordenine can serve as a competitive inhibitor for signaling molecules and act as a novel QS-based agent to defend against foodborne pathogens.
Quantification of Hordenine in a complex plant matrix by direct analysis in real time-high-resolution mass spectrometry: Application to the "plant of concern" Sceletium tortuosum
Drug Test Anal 2022 Apr;14(4):604-612.PMID:34750996DOI:10.1002/dta.3193.
Recently, there has been an increase in the recreational abuse of several psychoactive plants, resulting in the United Nations Office on Drugs and Crime creating a list of "plants of concern." One such material is Sceletium tortuosum and products derived from it. Regulation of these materials is challenging because of their innocuous appearance, the cumbersome sample preparation steps required to render the material into a form amenable to analysis by conventional techniques, the requirement for nuanced sample analysis protocols, and lengthy analysis times. It is demonstrated here that direct analysis in real time-high-resolution mass spectrometry (DART-HRMS) can be used to not only identify S. tortuosum material based on the detection of characteristic biomarkers including Hordenine and several mesembrine alkaloids, but also quantify the amount of Hordenine present. Using hordenine-d6 as an internal standard, a protocol, validated according to US Food and Drug Administration (FDA) Guidelines for the Development and Validation of Bioanalytical Methods, was devised for the quantification of the psychoactive component Hordenine. The method was then applied to the quantification of Hordenine in six commercially available products derived from the foliage and stems of S. tortuosum. By this method, the lower limit of quantification (LLOQ) was found to be 1 μg/ml. Observed Hordenine concentrations ranged from 0.02738 to 1.071 mg of Hordenine per gram of plant material. The developed technique provides an effective and quick means for the detection and quantification of Hordenine in S. tortuosum, which can be extended to analysis of other hordenine-containing products.
Hordenine Protects Against Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting Inflammation
Front Pharmacol 2021 Sep 1;12:712232.PMID:34539399DOI:10.3389/fphar.2021.712232.
Acute lung injury (ALI) is a respiratory disease that leads to death in severe cases. Hordenine (Hor), a barley-derived natural product, has various biological activities, including anti-inflammatory, and anti-oxidation activities. We investigated the effect of Hor on lipopolysaccharide-induced ALI and its potential mechanism. The anti-inflammatory effects of Hor were detected using in vivo and in vitro models by enzyme-linked immunosorbent assay, real-time polymerase chain reaction, western blotting, and molecular docking simulations. Hor inhibited increases in the levels of inflammatory factors both in vivo and in vitro, and its anti-inflammatory effect inhibited activation of protein kinase B, nuclear factor-κB, and mitogen-activated protein kinase signaling. Hor alleviated lipopolysaccharide-induced ALI by inhibiting inflammatory cytokine increases in vivo and in vitro and shows potential for preventing inflammatory disease.