Hodgkinsine
(Synonyms: (–)-Hodgkinsine) 目录号 : GC48453
An alkaloid with analgesic activity
Cas No.:18210-71-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Hodgkinsine is a pyrrolidinoindoline alkaloid that has been found in P. colorata and has analgesic activity.1 It increases latency to paw licking in the hot plate test and latency to tail withdrawal in the tail-flick test in mice when administered at a dose of 5 mg/kg.
1.Amador, T.A., Verotta, L., Nunes, D.S., et al.Antinociceptive profile of hodgkinsinePlanta Med.66(8)770-772(2000)
| Cas No. | 18210-71-4 | SDF | |
| 别名 | (–)-Hodgkinsine | ||
| Canonical SMILES | CN1[C@]2([H])[C@@](CC1)([C@]34C5=CC=CC=C5N[C@@]3([H])N(CC4)C)C6=CC=CC([C@@]78C9=CC=CC=C9N[C@]7([H])N(CC8)C)=C6N2 | ||
| 分子式 | C33H38N6 | 分子量 | 518.7 |
| 溶解度 | 储存条件 | -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 | 1.9279 mL | 9.6395 mL | 19.279 mL |
| 5 mM | 0.3856 mL | 1.9279 mL | 3.8558 mL |
| 10 mM | 0.1928 mL | 0.9639 mL | 1.9279 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。
Antinociceptive profile of Hodgkinsine
Planta Med 2000 Dec;66(8):770-2.PMID:11199142DOI:10.1055/s-2000-9604.
To further understand the mechanism of analgesic activity and structural requirements of pyrrolidinoindoline alkaloids identified in Psychotria colorata, we here report the analgesic activity of the trimer Hodgkinsine on thermal and chemical models of analgesia. Results show that Hodgkinsine produces a dose-dependent naloxone reversible analgesic effect in thermal models of nociception, suggesting that activation of opioid receptors participates in Hodgkinsine's mode of action. Hodgkinsine shows a potent dose-dependent analgesic activity against capsaicin-induced pain, indicating the participation of NMDA receptors in hodgkinsine-induced analgesia. Such a dual mechanism of action may be of interest for developing innovative analgesics.
Catalytic enantioselective desymmetrisation as a tool for the synthesis of Hodgkinsine and Hodgkinsine B
Chemistry 2012 Dec 21;18(52):16754-64.PMID:23203932DOI:10.1002/chem.201203150.
Two palladium-catalysed amination protocols are deployed in the desymmetrisation of the complex dimeric alkaloid meso-chimonanthine. The power of these transformations is showcased in an efficient formal and total synthesis of the natural products Hodgkinsine and Hodgkinsine B, respectively.
Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid Hodgkinsine and preliminary assessment of their antinociceptive activity
J Org Chem 2007 Oct 12;72(21):7909-14.PMID:17887704DOI:10.1021/jo7013643.
The previously unknown stereoisomers 3, 4, ent-1, and ent-4 of the tris(pyrrolidinoindoline) alkaloids Hodgkinsine (1) and Hodgkinsine B (2) were prepared by stereocontrolled total synthesis. In each synthesis, a catalyst-controlled intramolecular Heck reaction was the key step in appending a third cis-pyrrolidinoindoline ring to a hexacyclic chimonanthine precursor. Results of the preliminary evaluation of these Hodgkinsine stereoisomers in the tail flick and capsaicin pain models are reported.
Catalyst-controlled oligomerization for the collective synthesis of polypyrroloindoline natural products
Nat Chem 2017 Dec;9(12):1165-1169.PMID:29168485DOI:10.1038/nchem.2825.
In nature, many organisms generate large families of natural product metabolites that have related molecular structures as a means to increase functional diversity and gain an evolutionary advantage against competing systems within the same environment. One pathway commonly employed by living systems to generate these large classes of structurally related families is oligomerization, wherein a series of enzymatically catalysed reactions is employed to generate secondary metabolites by iteratively appending monomers to a growing serial oligomer chain. The polypyrroloindolines are an interesting class of oligomeric natural products that consist of multiple cyclotryptamine subunits. Herein we describe an iterative application of asymmetric copper catalysis towards the synthesis of six distinct oligomeric polypyrroloindoline natural products: Hodgkinsine, Hodgkinsine B, idiospermuline, quadrigemine H and isopsychotridine B and C. Given the customizable nature of the small-molecule catalysts employed, we demonstrate that this strategy is further amenable to the construction of quadrigemine H-type alkaloids not isolated previously from natural sources.
Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids
Bioorg Med Chem 2002 Jul;10(7):2133-42.PMID:11983509DOI:10.1016/s0968-0896(02)00078-0.
Hodgkinsine, a trimeric pyrrolidinoindoline type alkaloid, present as a major constituent of Psychotria spp. (Rubiaceae), has shown to produce dose-dependent, naloxone reversible, analgesic effect in thermal models of nociception and in the capsaicin-induced pain. SAR studies have been initiated by synthesizing the three diastereomeric dimers (chimonanthines) (11-13) which were evaluated in vitro and in vivo along with the synthetic intermediates. Strong binding affinities for mu opioid receptors were found for (-)- and (+)-chimonanthine monourethanes (9 and 10), whereas (-)-, (+)- and (meso)-chimonanthine (11-13) and Hodgkinsine displayed low affinity. In vivo data have shown that only (+)-chimonanthine (12) and calycosidine resemble the analgesic profile found for Hodgkinsine.