Isopteropodine
(Synonyms: 钩藤碱 E) 目录号 : GC39076
Isopteropodine 是从 Uncaria tomentosa 分离得到的一种异育亨宾型辛吲哚生物碱，是 M1 型毒蕈碱乙酰胆碱 (muscarinic M1) 受体及 5-HT2 受体的正向调节剂。
Cas No.:5171-37-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isopteropodine is heteroyohimbine-type oxindole alkaloid components of Uncaria tomentosa (Willd.) DC. Isopteropodine acts as positive modulators of muscarinic M1 and 5-HT2 receptors[1].
[1]. Tai-Hyun Kang,etc. Pteropodine and isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte. European Journal of Pharmacology, Volume 444, Issues 1-2, 2002, Pages 39-45, ISSN 0014-2999,
| Cas No. | 5171-37-9 | SDF | |
| 别名 | 钩藤碱 E | ||
| Canonical SMILES | O=C(C1=CO[C@@H](C)[C@]([C@]1([H])C[C@]23[H])([H])CN2CC[C@]43C(NC5=C4C=CC=C5)=O)OC | ||
| 分子式 | C21H24N2O4 | 分子量 | 368.43 |
| 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 | 2.7142 mL | 13.5711 mL | 27.1422 mL |
| 5 mM | 0.5428 mL | 2.7142 mL | 5.4284 mL |
| 10 mM | 0.2714 mL | 1.3571 mL | 2.7142 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。
Antimicrobial activity of Isopteropodine
Z Naturforsch C J Biosci 2005 May-Jun;60(5-6):385-8.PMID:16042336DOI:10.1515/znc-2005-5-603.
Bioassay-directed fractionation for the determination of antimicrobial activity of Uncaria tomentosa, has led to the isolation of Isopteropodine (0.3%), a known Uncaria pentacyclic oxindol alkaloid that exhibited antibacterial activity against Gram positive bacteria.
Pteropodine and Isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte
Eur J Pharmacol 2002 May 24;444(1-2):39-45.PMID:12191580DOI:10.1016/s0014-2999(02)01608-4.
Pteropodine and Isopteropodine are heteroyohimbine-type oxindole alkaloid components of Uncaria tomentosa (Willd.) DC, a Peruvian medicinal plant known as cat's claw. In this study, the effects of these alkaloids on the function of Ca(2+)-activated Cl(-) currents evoked by stimulation of G protein-coupled muscarinic M(1) acetylcholine and 5-HT(2) receptors were studied in Xenopus oocytes in which rat cortex total RNA was translated. Pteropodine and Isopteropodine (1-30 microM) failed to induce membrane current by themselves. However, these alkaloids markedly enhanced the current responses evoked by both acetylcholine and 5-hydroxyhyptamine (5-HT) in a concentration-dependent and reversible manner with the maximal effects at 30 microM. Pteropodine and Isopteropodine produced 2.7- and 3.3-fold increases in the acetylcholine response with EC(50) values of 9.52 and 9.92 microM, respectively, and 2.4- and 2.5-fold increases in the 5-HT response with EC(50) values of 13.5 and 14.5 microM, respectively. In contrast, in oocytes injected with total RNA from the rat cerebellum or spinal cord, neither alkaloid had an effect on the metabotropic current responses mediated by glutamate receptor(1 and 5) (mGlu(1/5)) receptors or ionotropic responses mediated by N-methyl-D-aspartate, kainic acid or glycine. Pteropodine and Isopteropodine (10 microM) significantly reduced the EC(50) values of acetylcholine and 5-HT that elicited current responses, but had no effect on the maximal current responses elicited by acetylcholine and 5-HT. On the other hand, mitraphylline, a stereoisomer of pteropodine, failed to modulate acetylcholine- and 5-HT-induced responses. These results suggest that pteropodine and Isopteropodine act as positive modulators of muscarinic M(1) and 5-HT(2) receptors.
Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells
Br J Haematol 2006 Mar;132(5):615-22.PMID:16445836DOI:10.1111/j.1365-2141.2005.05907.x.
Natural products are still an untapped source of promising lead compounds for the generation of antineoplastic drugs. Here, we investigated for the first time the antiproliferative and apoptotic effects of highly purified oxindole alkaloids, namely Isopteropodine (A1), pteropodine (A2), isomitraphylline (A3), uncarine F (A4) and mitraphylline (A5) obtained from Uncaria tomentosa, a South American Rubiaceae, on human lymphoblastic leukaemia T cells (CCRF-CEM-C7H2). Four of the five tested alkaloids inhibited proliferation of acute lymphoblastic leukaemia cells. Furthermore, the antiproliferative effect of the most potent alkaloids pteropodine (A2) and uncarine F (A4) correlated with induction of apoptosis. After 48 h, 100 micromol/l A2 or A4 increased apoptotic cells by 57%. CEM-C7H2 sublines with tetracycline-regulated expression of bcl-2, p16ink4A or constitutively expressing the cowpox virus protein crm-A were used for further studies of the apoptosis-inducing properties of these alkaloids. Neither overexpression of bcl-2 or crm-A nor cell-cycle arrest in G0/G1 phase by tetracycline-regulated expression of p16INK4A could prevent alkaloid-induced apoptosis. Our results show the strong apoptotic effects of pteropodine and uncarine F on acute leukaemic lymphoblasts and recommend the alkaloids for further studies in xenograft models.
Long-term response on growth, antioxidant enzymes, and secondary metabolites in salicylic acid pre-treated Uncaria tomentosa microplants
Biotechnol Lett 2015 Dec;37(12):2489-96.PMID:26272395DOI:10.1007/s10529-015-1931-0.
Objective: To obtain micro propagated Uncaria tomentosa plantlets with enhanced secondary metabolites production, long-term responses to salicylic acid (SA) pre-treatments at 1 and 100 µM were evaluated after propagation of the plantlets in a SA-free medium. Results: SA pre-treatments of single node cuttings OF U. tomentosa produced long-term responses in microplants grown for 75 days in a SA-free medium. Reduction in survival rate, root formation, and stem elongation were observed only with 100 µM SA pre-treatments with respect to the control (0 + DMSO).Both pre-treatments enhanced H2O2 and inhibited superoxide dismutase and catalase activities, while guaiacol peroxidase was increased only with 1 µM SA. Also, both pre-treatments increased total monoterpenoid oxindole alkaloids by ca. 55 % (16.5 mg g(-1) DW), including Isopteropodine, speciophylline, mitraphylline, isomitraphylline, rhynchopylline, and isorhynchopylline; and flavonoids by ca. 21 % (914 μg g(-1) DW), whereas phenolic compounds were increased 80 % (599 μg g(-1) DW) at 1 µM and 8.2 % (359 μg g(-1) DW) at 100 µM SA. Conclusion: Pre-treatment with 1 µM SA of U.tomentosa microplants preserved the survival rate and increased oxindole alkaloids, flavonoids, and phenolic compounds in correlation with H2O2 and peroxidase activity enhancements, offering biotechnological advantages over non-treated microplants.
Identification of PXR activators from Uncaria rhynchophylla (Gou Teng) and Uncaria tomentosa (Cat's Claw)
Drug Metab Dispos 2023 Feb 16;DMD-AR-2022-001234.PMID:36797057DOI:10.1124/dmd.122.001234.
Uncaria rhynchophylla (Gou Teng) and Uncaria tomentosa (Cat's Claw) are frequently used herbal supplements in Asia and America, respectively. Despite their common usage, information is limited regarding potential herb-drug interactions associated with Gou Teng and Cat's Claw. The pregnane X receptor (PXR) is a ligand-dependent transcription factor that regulates Cytochrome P450 3A4 (CYP3A4) expression and contributes to some known herb-drug interactions. A recent study found that Gou Teng induces CYP3A4 expression, but its mechanism is unknown. Cat's Claw has been determined as a PXR-activating herb, but the PXR activators in Cat's Claw have not been identified. Using a genetically engineered PXR cell line, we found that the extracts of Gou Teng and Cat's Claw can dose-dependently activate PXR and induce CYP3A4 expression. We next used a metabolomic approach to profile the chemical components in the extracts of Gou Teng and Cat's Claw followed by screening for PXR activators. Four compounds, isocorynoxeine, rhynchophylline, isorhynchophylline, and corynoxeine, were identified as PXR activators from both Gou Teng and Cat's Claw extracts. In addition, three more PXR activators were identified from the extracts of Cat's Claw including Isopteropodine, pteropodine, and mitraphylline. All these seven compounds showed the half maximal effective concentration < 10 µM for PXR activation. In summary, our work determined Gou Teng as a PXR-activating herb and discovered novel PXR activators from Gou Teng as well as Cat's Claw. Significance Statement Our data can be used to guide the safe use of Gou Teng and Cat's Claw by avoiding PXR-mediated herb-drug interactions.