Hypaphorine
(Synonyms: 刺桐碱) 目录号 : GC38797
An indole alkaloid with plant growth regulatory and anti-inflammatory activities
Cas No.:487-58-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Hypaphorine is an indole alkaloid that has been found in P. tinctorius and has plant growth regulatory and anti-inflammatory activities.1,2 It reverses inhibition of E. globulus seedling root growth induced by indole-3-acetic acid .1 Hypaphorine (12.5-50 ?M) inhibits LPS-induced apoptosis in BEAS-2B bronchial epithelial cells.2 It decreases the severity of lung injury and bronchoalveolar fluid (BALF) neutrophil infiltration in a rat model of LPS-induced acute lung injury when administered at a dose of 10 mg/kg.
1.Ditengou, F.A., and Lapeyrie, F.Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlingsMol. Plant Microbe Interact.13(2)151-158(2000) 2.Ding, Y.-H., Miao, R.-X., and Zhang, Q.Hypaphorine exerts anti-inflammatory effects in sepsis induced acute lung injury via modulating DUSP1/p38/JNK pathwayKaohsiung J. Med. Sci.37(10)883-893(2021)
| Cas No. | 487-58-1 | SDF | |
| 别名 | 刺桐碱 | ||
| Canonical SMILES | C[N+](C)(C(C([O-])=O)CC1=CNC2=C1C=CC=C2)C | ||
| 分子式 | C14H18N2O2 | 分子量 | 246.3 |
| 溶解度 | H2O : 100 mg/mL (406.01 mM; Need ultrasonic); DMSO : < 1 mg/mL (insoluble or slightly soluble) | 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 | 4.0601 mL | 20.3004 mL | 40.6009 mL |
| 5 mM | 0.812 mL | 4.0601 mL | 8.1202 mL |
| 10 mM | 0.406 mL | 2.03 mL | 4.0601 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。
Hypaphorine exerts anti-inflammatory effects in sepsis induced acute lung injury via modulating DUSP1/p38/JNK pathway
Kaohsiung J Med Sci 2021 Oct;37(10):883-893.PMID:34250720DOI:10.1002/kjm2.12418.
Sepsis is a systemic inflammatory response syndrome attributed to infection, while sepsis-induced acute lung injury (ALI) has high morbidity and mortality. Here, we aimed to explore the specific mechanism of Hypaphorine's anti-inflammatory effects in ALI. Lipopolysaccharide (LPS) was adopted to construct ALI model both in vivo and in vitro. BEAS-2B cell viability and apoptosis was testified by the MTT assay and flow cytometry. Reverse transcription-polymerase chain reaction (RT-PCR) and enzyme-linked immunosorbent assay (ELISA) were performed to examine the expression of proinflammatory cytokines (IL-1β, IL-6, TNF-α, and IL-18), and Western blot was adopted to examine the expression of the apoptosis-related proteins (Bax, Bcl2, and Caspase3) and the DUSP1/p38/JNK signaling pathway. At the same time, lung injury score, lactate dehydrogenase (LDH) and myeloperoxidase (MPO) activity were monitored. The dry/wet weight method was used to examine lung edema, and the total protein content in BALF was determined to test pulmonary vascular permeability. As the data suggested, Hypaphorine inhibited the LPS-mediated apoptosis of alveolar epithelial cells. What is more, Hypaphorine attenuated the expression of inflammatory factors (IL-1β, IL-6, TNF-α, and IL-18) and inactivated the p38/JNK signaling pathway through upregulating DUSP1 in a dose-dependent manner. Meanwhile, DUSP1 knockdown weakened the anti-inflammatory effect of Hypaphorine on LPS-mediated lung injury. Furthermore, Hypaphorine also relieved LPS induced ALI in rats with anti-inflammatory effects. Taken together, Hypaphorine prevented LPS-mediated ALI and proinflammatory response via inactivating the p38/JNK signaling pathway by upregulating DUSP1.
Hypaphorine is present in human milk in association with consumption of legumes
J Agric Food Chem 2013 Aug 7;61(31):7654-60.PMID:23855762DOI:10.1021/jf401758f.
In metabolomic analysis of human milk amines, we found a previously unidentified compound. This was tentatively identified as Hypaphorine, an indole alkaloid composed of tryptophan and three methyls, and with neurological and glucose-lowering effects in rodents. Hypaphorine identity was confirmed by Hypaphorine synthesis, and then a fluorometric method was developed to quantify Hypaphorine in milk and foods. Using dietary records, we identified peanut products as probable sources of Hypaphorine. Milk from 24 lactating women showed widely varying Hypaphorine, with a mean ± SD 0.34 ± 0.33 μM, and the highest concentration of 1.24 μM. Peanuts showed high Hypaphorine of 70 μg/g compared to 60 and 100 μg/g in dried chickpeas and lentils. Dietary challenge in lactating women with hypaphorine-rich foods demonstrated transfer of Hypaphorine into milk with Hypaphorine appearance peaking 5-18 h after consumption and prolonged disappearance indicative of slow excretion or metabolism. The potential functional roles of Hypaphorine in human nutrition remain to be addressed.
Pharmacokinetic Study of Hypaphorine, a Potential Agent for Treating Osteoclast-based Bone Loss, on Rats Using LC-MS/MS
Comb Chem High Throughput Screen 2022;25(11):1889-1896.PMID:34610780DOI:10.2174/1386207325666211005144429.
Aims and objectives: A high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for determining Hypaphorine, a potential agent for treating osteoclast- based bone loss, was developed and validated in rat plasma. Materials and methods: Plasma samples were pretreated by the protein precipitation. Chromatographic separation was performed using an Inertsil ODS-3 column (50 mm × 4.6 mm, 5 μm). The mobile phase consisted of water (containing 0.1% formic acid) and acetonitrile in a gradient mode at a flow rate of 0.5 mL/min. The transitions from protonated precursor ion [M + H]+ to the particular daughter ion were acquired using selected reaction monitoring (SRM). The mass transitions of Hypaphorine and IS were found to be 247 → 188 and m/z 219 → 188, respectively. The method was validated in terms of selectivity, linearity, accuracy and precision, extraction recovery and matrix effect, stability, and carryover. Results: It showed good linearity over the range of 1-2000 ng/mL (R2 = 0.9978). The intra-batch accuracy was within 93.95-105.81%, and the precision was within 4.92-11.53%. The inter-batch accuracy was within 96.18-100.39% with a precision of 6.22-11.23%. The extraction recovery and matrix factors were acceptable. Conclusion: The simple and rapid method was successfully applied to the pharmacokinetic study in rats following oral administration of Hypaphorine at the doses of 0.5, 1.5, and 4.5 mg/kg.
Vaccaria Hypaphorine alleviates lipopolysaccharide-induced inflammation via inactivation of NFκB and ERK pathways in Raw 264.7 cells
BMC Complement Altern Med 2017 Feb 20;17(1):120.PMID:28219355DOI:10.1186/s12906-017-1635-1.
Background: Activation of macrophage is involved in many inflammation diseases. Lipopolysaccharide (LPS) is a powerful inflammatory signal contributing to monocytes/macrophages activation associated with increased proinflammatory cytokines expressions. We recently identified that vaccarin was expected to protect endothelial cells from injury. Hypaphorine was abundantly found in vaccaria semen. However, the potential roles and underlying mechanisms of vaccaria Hypaphorine on macrophage inflammation have been poorly defined. Methods: This study was designed to determine the effects of vaccaria Hypaphorine on LPS-mediated inflammation in RAW 264.7 cells. Results: In this study, we demonstrated that vaccaria Hypaphorine dramatically ameliorated LPS-induced nitric oxide (NO) release and productions of proinflammatory cytokines including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, IL-10, monocyte chemoattractant protein 1 (MCP-1) and prostaglandin E2 (PGE2) in RAW 264.7 cells. LPS-stimulated expressions of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were down-regulated by vaccaria Hypaphorine. Furthermore, vaccaria Hypaphorine retarded LPS-induced phosphorylation of ERK, nuclear factor kappa beta (NFκB), NFκB inhibitor IκBα, and IKKβ. Immunofluorescence staining revealed that vaccaria Hypaphorine eliminated the nuclear translocation of NFκB in LPS-treated RAW 264.7 cells. Conclusion: It was seen that vaccaria Hypaphorine counteracted inflammation via inhibition of ERK or/and NFκB signaling pathways. Collectively, we concluded that vaccaria Hypaphorine can be served as an anti-inflammatory candidate.
Hypaphorine, an Indole Alkaloid Isolated from Caragana korshinskii Kom., Inhibites 3T3-L1 Adipocyte Differentiation and Improves Insulin Sensitivity in Vitro
Chem Biodivers 2017 Jul;14(7).PMID:28398659DOI:10.1002/cbdv.201700038.
Obesity, a major health problem worldwide, is a complex multifactorial chronic disease that increases the risk for insulin resistance, type 2 diabetes, coronary heart disease, and hypertension. In this study, we assessed methods to isolate Hypaphorine, a potent drug candidate for obesity and insulin resistance. Semi-preparative reversed-phase liquid chromatography (semi-preparative RPLC) was established as a method to separate three compounds, adenosine, l-tryptophan, and Hypaphorine, from the crude extracts of Caragana korshinskii Kom. Due to its specific chemical structure, the effect of Hypaphorine on differentiation and dexamethasone (DXM) induced insulin resistance of 3T3-L1 cells was investigated. The structures of the three compounds were confirmed by UV, 1 H-NMR, and 13 C-NMR analysis and compared with published data. The activity results indicated that Hypaphorine prevented the differentiation of 3T3-L1 preadipocytes into adipocytes by down-regulating hormone-stimulated protein expression of peroxisome proliferator activated receptor γ (PPARγ) and CCAAT/enhancer binding protein (C/EBPα), and their downstream targets, sterol regulatory element binding protein 1 c (SREBP1c) and fatty acid synthase (FAS). Hypaphorine also alleviated DXM-induced insulin resistance in differentiated 3T3-L1 adipocytes via increasing the phosphorylation level of Akt2, a key protein in the insulin signaling pathway. Taken together, we suggest that the method can be applied to large-scale extraction and large-quantity preparation of Hypaphorine for treatment of obesity and insulin resistance.