Scopoletin (Gelseminic acid) (Synonyms: Esculetin 6-methyl ether, 7-Hydroxy-6-methoxycoumarin, 6-Methoxy-7-hydroxycoumarin, NSC 405647) |
Catalog No.GC31699
One-Click Copy Product Info
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Scopoletin (Gelseminic acid) is an inhibitor of acetylcholinesterase (AChE).
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 92-61-5
Sample solution is provided at 25 µL, 10mM.
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Scopoletin (Gelseminic acid) is a naturally occurring phenolic coumarin and an acetylcholinesterase (AChE) inhibitor with IC50 of 168.6μM[1]. Scopoletin inhibits AChE and regulates nuclear factor-kappa B (NF-κB), mitogen-activated protein kinase (MAPK), and cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) signaling, thereby altering cholinergic neurotransmission, inflammatory activation, angiogenesis, and melanogenesis[1-4]. Scopoletin is used in research on cholinergic signaling, pigmentation, angiogenesis, autoimmune neuroinflammation, arthritis, urate crystal-induced inflammation, and inflammation-associated anxiety[1-7].
In vitro, Scopoletin (40μg/mL; 72h) increased intracellular melanin, tyrosinase activity, tyrosinase-related protein 1 (TRP-1), microphthalmia-associated transcription factor (MITF), cAMP production, and p38 MAPK phosphorylation in B16F10 melanoma cells[2]. Scopoletin (10μM, 30μM, and 100μM; 24h; 10ng/mL fibroblast growth factor 2) reduced human umbilical vein endothelial cell proliferation, migration, and tubule formation and decreased vascular endothelial growth factor expression, inhibitor of nuclear factor kappa-B kinase alpha phosphorylation, and inhibitor of NF-κB degradation[3]. Scopoletin (100μM; 18h; 100ng/mL lipopolysaccharide) reduced major histocompatibility complex class II, cluster of differentiation 80, cluster of differentiation 86, NF-κB phosphorylation, interleukin-1 beta, and tumor necrosis factor-alpha in mouse bone marrow-derived dendritic cells[4].
In vivo, Scopoletin (50mg/kg; intraperitoneal injection once daily from day 0 to day 20 after immunization) reduced disease scores, spinal-cord inflammatory infiltration, demyelination, dendritic-cell activation, and pathogenic T helper 1/T helper 17 responses in C57BL/6 mice with experimental autoimmune encephalomyelitis[4]. Scopoletin (50mg/kg and 100mg/kg; intraperitoneal injection once daily for 23 days) reduced joint inflammation, cartilage and bone destruction, synovial microvessel density, and angiogenic mediator expression in Sprague-Dawley rats with adjuvant-induced arthritis[5]. Scopoletin (50mg/kg, 100mg/kg, and 200mg/kg; single intraperitoneal injection; 6h) reduced leukocyte infiltration and inflammatory mediator production in the air pouches of ICR mice challenged with monosodium urate crystals[6]. Scopoletin (2mg/kg, 10mg/kg, and 50mg/kg; intraperitoneal injection once daily for 14 days) reduced microglial activation, interleukin-1 beta, interleukin-6, tumor necrosis factor-alpha, NF-κB/MAPK activation, and anxiety-like behavior in male C57BL/6 mice with complete Freund's adjuvant-induced chronic inflammation[7].
References：[1] Rollinger JM, Hornick A, Langer T, Stuppner H, Prast H. Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem. 2004;47(25):6248-6254. doi:10.1021/jm049655r.
[2] Kim DS, Cha SB, Park MC, Park SA, Kim HS, Woo WH, Mun YJ. Scopoletin stimulates melanogenesis via cAMP/PKA pathway and partially p38 activation. Biol Pharm Bull. 2017;40(12):2068-2074. doi:10.1248/bpb.b16-00690.
[3] Pan R, Gao XH, Lu D, Xu XX, Xia YF, Dai Y. Prevention of FGF-2-induced angiogenesis by scopoletin, a coumarin compound isolated from Erycibe obtusifolia Benth, and its mechanism of action. Int Immunopharmacol. 2011;11(12):2007-2016. doi:10.1016/j.intimp.2011.08.012.
[4] Zhang F, Zhang Y, Yang T, Ye ZQ, Tian J, Fang HR, et al. Scopoletin suppresses activation of dendritic cells and pathogenesis of experimental autoimmune encephalomyelitis by inhibiting NF-kappaB signaling. Front Pharmacol. 2019;10:863. doi:10.3389/fphar.2019.00863.
[5] Pan R, Gao XH, Li Y, Xia YF, Dai Y. Anti-arthritic effect of scopoletin, a coumarin compound occurring in Erycibe obtusifolia Benth stems, is associated with decreased angiogenesis in synovium. Fundam Clin Pharmacol. 2010;24(4):477-490. doi:10.1111/j.1472-8206.2009.00784.x.
[6] Yao X, Ding Z, Xia Y, Wei Z, Luo Y, Feleder C, et al. Inhibition of monosodium urate crystal-induced inflammation by scopoletin and underlying mechanisms. Int Immunopharmacol. 2012;14(4):454-462. doi:10.1016/j.intimp.2012.07.024.
[7] Luo L, Sun T, Yang L, Liu A, Liu QQ, Tian QQ, et al. Scopoletin ameliorates anxiety-like behaviors in complete Freund's adjuvant-induced mouse model. Mol Brain. 2020;13(1):15. doi:10.1186/s13041-020-0560-2.
| Cell experiment [1]: | |
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Cell lines |
Mouse bone marrow-derived dendritic cell |
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Preparation Method |
Mouse bone marrow-derived dendritic cells were cultured with Scopoletin and lipopolysaccharide. Major histocompatibility complex class II, cluster of differentiation 80, cluster of differentiation 86, inflammatory cytokines, and NF-κB phosphorylation were evaluated. |
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Reaction Conditions |
100μM; 18h |
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Applications |
Scopoletin reduced major histocompatibility complex class II, cluster of differentiation 80, and cluster of differentiation 86 expression, inhibited NF-κB phosphorylation, and decreased interleukin-1 beta and tumor necrosis factor-alpha levels. |
| Animal experiment [2]: | |
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Animal models |
Male C57BL/6 mouse model of complete Freund's adjuvant-induced chronic inflammation and anxiety |
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Preparation Method |
Male C57BL/6 mice aged 6-8 weeks received an intraplantar injection of complete Freund's adjuvant to establish chronic inflammation and anxiety and received intraperitoneal Scopoletin. Open-field and elevated-plus-maze behavior, microglial activation, inflammatory cytokines, and NF-κB/MAPK signaling were evaluated. |
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Dosage form |
2mg/kg, 10mg/kg, and 50mg/kg; intraperitoneal injection; 14 days |
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Applications |
Scopoletin dose-dependently reduced anxiety-like behavior, microglial activation, and peripheral and central interleukin-1 beta, interleukin-6, and tumor necrosis factor-alpha levels and inhibited NF-κB/MAPK signaling. |
| References： [1] Zhang F, Zhang Y, Yang T, Ye ZQ, Tian J, Fang HR, et al. Scopoletin suppresses activation of dendritic cells and pathogenesis of experimental autoimmune encephalomyelitis by inhibiting NF-kappaB signaling. Front Pharmacol. 2019;10:863. doi:10.3389/fphar.2019.00863. [2] Luo L, Sun T, Yang L, Liu A, Liu QQ, Tian QQ, et al. Scopoletin ameliorates anxiety-like behaviors in complete Freund's adjuvant-induced mouse model. Mol Brain. 2020;13(1):15. doi:10.1186/s13041-020-0560-2. | |
| Cas No. | 92-61-5 | SDF | |
| Synonyms | Esculetin 6-methyl ether, 7-Hydroxy-6-methoxycoumarin, 6-Methoxy-7-hydroxycoumarin, NSC 405647 | ||
| Canonical SMILES | O=C1C=CC2=CC(OC)=C(O)C=C2O1 | ||
| Formula | C10H8O4 | M.Wt | 192.17 |
| Solubility | DMSO : ≥ 32 mg/mL (166.52 mM) | Storage | Store at -20°C, protect from light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.2037 mL | 26.0186 mL | 52.0373 mL |
| 5 mM | 1.0407 mL | 5.2037 mL | 10.4075 mL |
| 10 mM | 520.4 μL | 2.6019 mL | 5.2037 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 11 reference(s) in Google Scholar.)