Lysergol
(Synonyms: 麦角醇) 目录号 : GC38415
Lysergol 从 Ipomoea muricata 种子中分离出的枝状生物碱，用于药物和营养素的生物增强剂，具有抗菌活性。Lysergol 已被用作降血压，精神镇痛药和刺激子宫和肠道的药物。
Cas No.:602-85-7
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
Lysergol, a clavine alkaloid isolated from seeds of Ipomoea muricata, is a bioenhancer for the drugs and nutrients and has antibacterial activity. Lysergol has been used as hypotensive, psychotropic analgesic and uterus- and intestine-stimulating drug[1][2].
[1]. Maurya A, et al. Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid-resistant Escherichia coli. Chem Biol Drug Des. 2013 Apr;81(4):484-90. [2]. Maurya A, et al. Quantitative determination of bioactive alkaloids lysergol and chanoclavine in Ipomoea muricata by reversed-phase high-performance liquid chromatography. Biomed Chromatogr. 2012 Sep;26(9):1096-100.
| Cas No. | 602-85-7 | SDF | |
| 别名 | 麦角醇 | ||
| Canonical SMILES | CN1[C@@](C2)([H])C(C3=CC=CC4=C3C2=CN4)=C[C@@H](CO)C1 | ||
| 分子式 | C16H18N2O | 分子量 | 254.33 |
| 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 | 3.9319 mL | 19.6595 mL | 39.319 mL |
| 5 mM | 0.7864 mL | 3.9319 mL | 7.8638 mL |
| 10 mM | 0.3932 mL | 1.9659 mL | 3.9319 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。
Lysergol monohydrate
Acta Crystallogr Sect E Struct Rep Online 2012 Feb 1;68(Pt 2):o523.PMID:22347120DOI:10.1107/S1600536812002632.
IN THE TITLE COMPOUND [SYSTEMATIC NAME: (7-methyl-4,6,6a,7,8,9-hexa-hydro-indolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate], C(16)H(18)N(2)O·H(2)O, the non-aromatic ring (ring C of the ergoline skeleton) directly fused to the aromatic rings is nearly planar, with a maximum deviation of 0.659 (3) Å, and shows an envelope conformation. In the crystal, hydrogen bonds between the Lysergol and water mol-ecules contribute to the formation of layers parallel to (10[Formula: see text]).
Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity
Org Lett 2017 Feb 3;19(3):624-627.PMID:28106398DOI:10.1021/acs.orglett.6b03779.
An efficient synthesis of ergot alkaloid Lysergol and its analogues is described, providing compounds for functional evaluation at the human 5-HT1A, 5-HT2A, 5-HT2B, or 5-HT2C receptors. Key features of the synthesis include the development of a tandem reaction to construct the multifunctionalized piperidine skeleton and use of a rhodium-catalyzed [3 + 2] annulation in the late-stage indole formation.
Antibacterial and synergy of clavine alkaloid Lysergol and its derivatives against nalidixic acid-resistant Escherichia coli
Chem Biol Drug Des 2013 Apr;81(4):484-90.PMID:23290001DOI:10.1111/cbdd.12103.
Antibacterial activity of Lysergol (1) and its semi-synthetic derivatives (2-14) and their synergy with the conventional antibiotic nalidixic acid (NA) against nalidixic acid-sensitive (NASEC) and nalidixic acid-resistant (NAREC) strains of Escherichia coli were evaluated. Lysergol (1) and derivatives (2-14) did not possess antibacterial activity of their own, but in combination, they significantly reduced the minimum inhibitory concentration (MIC) of NA. All the derivatives showed two- to eightfold reduction in the MIC of NA against NAREC and NASEC. Further, Lysergol (1) and its derivatives 10 and 11 brought down eightfold reductions in the MIC of tetracycline (TET) against multidrug-resistant clinical isolate of E. coli (MDREC). Treatment of these strains with the combinations of antibiotics and Lysergol and its derivatives 10 and 11 (at reduced concentrations) significantly decreased the viability of cells. In an another observation, Lysergol and its derivatives 10 and 11 inhibited ATP-dependent efflux pumps, which was evident by ATPase inhibition and down-regulation of multidrug ABC transporter ATP-binding protein (yojI) gene. These results may be of great help in antibacterial drug development from a very common, inexpensive, and non-toxic natural product.
Simultaneous quantification of berberine and Lysergol by HPLC-UV: evidence that Lysergol enhances the oral bioavailability of berberine in rats
Biomed Chromatogr 2012 Oct;26(10):1170-5.PMID:22213237DOI:10.1002/bmc.2674.
A sensitive and simple HPLC method was developed for the simultaneous quantification of berberine and Lysergol in rat plasma. The chromatographic separation was achieved on a C(18) column using isocratic elution with methanol-acetonitrile-0.1% ortho-phosphoric acid (25:20:55, v/v/v), pH adjusted to 6.5 with triethylamine and detected at a UV wavelength of 230 nm. The extraction of the berberine and Lysergol from the rat plasma with methylene chloride resulted in their high recoveries (82.62 and 90.17%). HPLC calibration curves for both berberine and Lysergol based on the extracts from the rat plasma were linear over a broad concentration range of 50-1000 ng/mL. The limit of quantification was 50 ng/mL. Intra- and inter-day precisions were <15% and accuracy was 87.12-92.55% for berberine and 87.01-92.26% for Lysergol. Stability studies showed that berberine and Lysergol were stable in rat plasma for short- and long-term period for sample preparation and analysis. The described method was successfully applied to study the pharmacokinetics of berberine as well as Lysergol following oral administration in Sprague-Dawley rats. The results of the study inferred that Lysergol improved the oral bioavailability of berberine.
Simple O-acylated derivatives of Lysergol and dihydrolysergol-I: synthesis and interaction with 5-HT2A, 5-HT2C and 5-HT1B receptors, and alpha1 adrenergic receptors
J Pharm Pharmacol 1999 Mar;51(3):319-30.PMID:10344634DOI:10.1211/0022357991772321.
A series of simple O-acylated derivatives of the naturally occurring clavine alkaloids Lysergol and dihydrolysergol-I were synthesized and tested in-vitro for their ability to interact with 5-HT2A receptors in rat tail artery, 5-HT2C receptors in piglet choroid plexus, 5-HT1B receptors in guinea-pig iliac artery and alpha1-adrenergic receptors in rat aorta. In contrast to the classical ergoline 5-HT2A receptor antagonists methysergide and LY53857, the compounds produced competitive antagonism of the 5-HT response in rat tail artery. Affinities of ergolines 3-14 were higher (pA2 values of 7.33-8.40) than those of the parent alcohols Lysergol (1) and dihydrolysergol-I (2), respectively. The introduction of an isopropyl substituent at the N(1) position of the compounds failed to enhance 5-HT2A receptor affinity. Compounds 3-14 exhibited lower affinities for alpha1-adrenergic receptors than for 5-HT2A receptors. In particular, those Lysergol derivatives that had an isopropyl substituent at the N(1) position were highly specific 5-HT2A receptor antagonists (ratio 5-HT2A/alpha1 = 302-3548). Selected derivatives of Lysergol (3-5, 9-11) which were assayed for radioligand binding at 5-HT2C receptors in piglet choroid plexus had affinities that were similar to those found in rat tail artery. Additionally, Lysergol and its N(1)-unsubstituted derivatives were found to be partial agonists (alpha of 0.2-0.4) for 5-HT2C receptor-mediated inositol phosphate accumulation in piglet choroid plexus. On the other hand, analogues with an isopropyl substituent at N(1) showed no measurable agonist activity. The observation that N(1)-unsubstituted derivatives of Lysergol possessed agonist properties at 5-HT2C receptors whereas their agonist activity at 5-HT2A receptors was marginal (alpha of 0.05 for compound 3 at 1 microM) or not measurable, suggests that these compounds have different abilities to cause conformational change at the two receptor types. Selected derivatives of Lysergol (3-5, 9-11) which were examined as ligands for 5-HT1B receptors in guinea-pig iliac artery caused insurmountable blockade of the contractile effect of 5-HT. N(1)-isopropyl derivatives had 30-50-fold lower affinities for 5-HT1B receptors of this tissue than their N(1)-unsubstituted analogues. It is concluded that O-acylated derivatives of the clavine alkaloids Lysergol and dihydrolysergol-I mimic therapeutically relevant ergolines due to the complexity of their pharmacological profile as partial agonists and antagonists at 5-HT2A, 5-HT2C and 5-HT1B receptors, and at alpha1-adrenergic receptors.