Structure of Scopoletin
CAS No.: 92-61-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Scopoletin has important anti-inflammatory activity by inhibiting the phosphorylation of NF-κB and p38 MAPK.
Synonyms: Gelseminic acid; Chrysatropic acid; NSC 405647
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CAS No. : | 92-61-5 |
Formula : | C10H8O4 |
M.W : | 192.17 |
SMILES Code : | COC1=C(O)C=C2OC(=O)C=CC2=C1 |
Synonyms : |
Gelseminic acid; Chrysatropic acid; NSC 405647
|
MDL No. : | MFCD00006872 |
InChI Key : | RODXRVNMMDRFIK-UHFFFAOYSA-N |
Pubchem ID : | 5280460 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
CCRF-CEM | 26.1 µM (IC50) | 72 hours | Evaluate the cytotoxicity of Scopoletin on CCRF-CEM cells | Molecules. 2016 Apr 15;21(4):496 |
SCN second-stage juveniles (J2) | 81.00 µg/mL, 40.50 µg/mL, 20.25 µg/mL, 4.05 µg/mL, 0.81 µg/mL | 12, 24, 48, 72, and 96 hours | Evaluate the nematicidal activity of Scopoletin against SCN J2. High concentrations of Scopoletin (T1 and T2) showed significant effects on J2 poisoning, while lower concentrations (T4 and T5) had negligible effects. | Life (Basel). 2021 Oct 26;11(11):1143 |
HeLa cells | 250 µM | 15 minutes | To test the antioxidant capacity of Sp under oxidative stress conditions, results showed that Sp significantly reduced 3-AT-induced oxidative radicals and improved cell viability. | Cell Death Dis. 2020 Sep 10;11(9):739 |
Horseradish peroxidase (HRP) | 1 µM | 150 msec to 5 sec | Scopoletin rapidly reacts with HRP to form a stable, spectroscopically distinguishable form of the enzyme, inhibiting HRP's reactions with molecular oxygen and indole-3-acetic acid (IAA). | Plant Physiol. 1972 Jun;49(6):1012-8 |
Phakopsora pachyrhizi uredospores | 500 µM | 16 hours | Scopoletin inhibited the germination of Pp spores, and this inhibition was reversible. | Plant J. 2019 Aug;99(3):397-413 |
Bone marrow-derived dendritic cells (BM-DCs) | 100 µM | 18 hours | Scopoletin significantly inhibited the activation of BM-DCs, reducing the expression of MHC II, CD80, and CD86. | Front Pharmacol. 2019 Aug 2;10:863 |
Rheumatoid arthritis fibroblast-like synoviocytes (HFLS-RA) | 20 µM | 24 and 48 hours | To evaluate the inhibitory effect of Scopoletin on HFLS-RA cell migration. Results showed that Scopoletin significantly reduced single-cell migration but only slightly inhibited collective migration. | Front Pharmacol. 2022 Jul 25;13:946210 |
Rheumatoid arthritis fibroblast-like synoviocytes (HFLS-RA) | 20 µM | 24 and 48 hours | To evaluate the inhibitory effect of Scopoletin on HFLS-RA cell proliferation. Results showed that Scopoletin significantly inhibited HFLS-RA proliferation at 30 μM and onwards. | Front Pharmacol. 2022 Jul 25;13:946210 |
Rat insulinoma 5f (RIN5f) cells | 100 µM | 24 hours | To evaluate the protective effect of SPL on palmitate-induced ER stress. SPL reduced the phosphorylation levels of IRE1α, PERK, and ATF6α induced by palmitate, indicating that SPL effectively inhibited ER stress in RIN5f cells. | Cell Stress Chaperones. 2018 Sep;23(5):857-869 |
SHSY-5Y cells | 250 µM | 24 hours | To evaluate the protective effects of Sp against MPP+-induced mitochondrial dysfunction and oxidative stress, results showed that Sp restored mitochondrial function and reduced oxidative stress. | Cell Death Dis. 2020 Sep 10;11(9):739 |
HEK 293 cells | 2 mM | 24 hours | Luciferase reporter assay confirmed Scopoletin activates HIV-1 LTR via NF-κB pathway | Int J Mol Sci. 2023 Aug 10;24(16):12649 |
Spodoptera frugiperda Sf9 cells | 0, 10, 50, 90 µM | 24 hours | To investigate the effect of scopoletin on intracellular free calcium [Ca2+]i levels in Sf9 cells. Results showed that scopoletin significantly elevated the [Ca2+]i levels in a concentration-dependent manner. | Front Physiol. 2019 Mar 6;10:164 |
Rheumatoid arthritis fibroblast-like synoviocytes (HFLS-RA) | 20 µM | 24 hours | To evaluate the inhibitory effect of Scopoletin on HFLS-RA cell invasion. Results showed that Scopoletin reduced the number of invasive cells, but the inhibitory rate was approximately half that of umbelliferone. | Front Pharmacol. 2022 Jul 25;13:946210 |
FL83B hepatocytes | 5 µM–25 µM (IC50) | 24 hours | To investigate the effects of scopoletin on MG-induced insulin resistance, results showed that scopoletin promoted Akt phosphorylation, restored PPARγ expression, suppressed PTP1B expression, and promoted GLUT2 plasma translocation. | Molecules. 2015 Feb 9;20(2):2786-801 |
SH-SY5Y cells | 5 µM | 3 hours pretreatment followed by 24 hours exposure to H2O2 | To evaluate the neuroprotective effects of scopoletin against H2O2-induced neuronal cell death. Results showed that scopoletin pretreatment significantly increased cell viability (95.1±4.7%), reduced apoptotic cell count (13.3±1.2%) and ROS levels (100.0±1.4%), and maintained the expression levels of SIRT1, FoxO3a, ADAM10, BCL-2, and antioxidant enzymes (catalase and SOD2). | RSC Adv. 2020 Apr 27;10(28):16593-16606 |
Candida tropicalis ATCC 28707 | 50 mg/mL | 48 hours | To evaluate the antifungal activity of scopoletin against a multidrug-resistant Candida tropicalis strain. Results showed scopoletin has a fungistatic effect, significantly reducing fungal growth curves and cell density (91.7% reduction). | Front Microbiol. 2020 Jul 7;11:1525 |
Raw 264.7 cells | 1–20 µM | 5 days | Scopoletin promoted the formation of TRAP-positive multinucleated osteoclasts and bone resorption, reversing the impairment of osteoclast differentiation by high glucose | Biomedicines. 2021 Jun 7;9(6):648 |
Alternaria alternata | 48, 96, 240, 480 μg ml–1 | 6 days | To test the inhibitory effect of Scopoletin on the growth of Alternaria alternata. Results showed that Scopoletin significantly inhibited fungal growth, with higher concentrations showing stronger inhibition. | J Exp Bot. 2014 Aug;65(15):4305-15 |
MC3T3-E1 cells | 1–20 µM | 7 days | Scopoletin enhanced ALP activity and mineralized bone nodule deposition, ameliorating the impairment of osteoblast differentiation by high glucose | Biomedicines. 2021 Jun 7;9(6):648 |
Jurkat T cells (C11 cell line) | 0.25-2.0 mM | 72 hours | Scopoletin reactivated latent HIV-1 transcription in a time-dependent manner, with GFP+ cells increasing from 8.02% to 42.65% | Int J Mol Sci. 2023 Aug 10;24(16):12649 |
Jurkat T cells (A10.6 cell line) | 0.2-1.6 mM | 72 hours | Scopoletin reactivated latent HIV-1 transcription in a dose-dependent manner, with GFP+ cells increasing from 10.72% to 28.87% | Int J Mol Sci. 2023 Aug 10;24(16):12649 |
CEM/ADR5000 | 37.5 µM (IC50) | 72 hours | Evaluate the cytotoxicity of Scopoletin on CEM/ADR5000 cells | Molecules. 2016 Apr 15;21(4):496 |
CEM/ADR5000 | 37.5 ± 2.9 µM (IC50) | 72 hours | Evaluate the cytotoxicity of Scopoletin on CEM/ADR5000 cells | Molecules. 2016 Apr 15;21(4):496 |
CCRF-CEM | 26.1 ± 1.6 µM (IC50) | 72 hours | Evaluate the cytotoxicity of Scopoletin on CCRF-CEM cells | Molecules. 2016 Apr 15;21(4):496 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Tetranychus cinnabarinus (carmine spider mite) | Adult female mites | Dip method | 0.938 mg/mL (LC50) | 48 hours | To evaluate the acaricidal toxicity of scopoletin against T. cinnabarinus. Results showed that scopoletin exhibited significant acaricidal activity with an LC50 value of 0.938 mg/mL. | Front Physiol. 2019 Mar 6;10:164 |
Male mice | DSS-induced colitis model | Oral | 1 mg/kg, 1.5 mg/kg, 2 mg/kg | Once daily, starting 14 days prior to and during DSS treatment | Scopoletin significantly improved DSS-induced colitis symptoms, including reduced weight loss and colonic shortening, decreased levels of TNF-α, IL-1β, and IL-12 cytokines, attenuated NLRP3 inflammasome activation, and modulated the immune response by elevating PPARγ expression and suppressing NF-κB pathway activation. Additionally, scopoletin altered gut microbiota composition by increasing beneficial Lactobacillus and Bifidobacteria and reducing E. coli, and enhanced tight junction proteins, indicating improved intestinal barrier integrity. | Inflammation. 2025 Apr;48(2):575-589 |
Sprague Dawley rats | High-fat, high-fructose diet (HFFD)-fed rats | Oral | 1 mg/kg/day | Once daily for 45 days | To evaluate the effect of SPL on HFFD-induced pancreatic ER stress. SPL reduced the phosphorylation levels of IRE1α, PERK, and ATF6α induced by HFFD and inhibited the phosphorylation of JNK, indicating that SPL effectively alleviated pancreatic ER stress. | Cell Stress Chaperones. 2018 Sep;23(5):857-869 |
Db/db mice | Type 2 diabetes model | Oral | 10 mg/kg | Once daily for 10 weeks | Scopoletin inhibited bone loss by enhancing the induction of bone turnover markers, increasing bone mineral density and content | Biomedicines. 2021 Jun 7;9(6):648 |
Wistar rats | MG-induced diabetic model | Oral administration | 10 mg/kg | Once daily for 12 weeks | To investigate the protective effects of scopoletin against MG-induced hyperglycemia and insulin resistance, results showed that scopoletin improved OGTT results, reduced fasting blood glucose, restored C-peptide levels, ameliorated dyslipidemia, and promoted MG metabolism into D-lactic acid by activating Nrf2, thereby inhibiting AGEs generation. | Molecules. 2015 Feb 9;20(2):2786-801 |
Sprague-Dawley rats | Healthy rats | Oral | 100 mg/kg | Single dose | Evaluate pharmacokinetics and biodistribution of Sco-Ms | Acta Pharmacol Sin. 2017 Mar;38(3):424-433 |
Zebrafish embryos | Zebrafish embryo developmental toxicity model | Aqueous solution exposure | 18.5 µg/mL | Exposure solution changed daily until 120 hpf | Evaluated the metabolic effects of Scopoletin on zebrafish embryos, revealing significant metabolic disturbances | Metabolites. 2022 Oct 1;12(10):934 |
C57BL/6 mice | Complete Freund’s adjuvant (CFA)-induced chronic inflammation anxiety model | Intraperitoneal injection | 2.0, 10.0, 50.0 mg/kg | Once daily for 14 consecutive days | SP dose-dependently ameliorated CFA-induced anxiety-like behaviors, inhibited microglia activation, decreased peripheral and central IL-1β, IL-6, and TNF-α levels, and modulated the imbalance of excitatory/inhibitory receptors and neurotransmitters | Mol Brain. 2020 Feb 4;13(1):15 |
Drosophila melanogaster | Park13 mutant flies | Oral administration | 2.5 mM | Continuous treatment starting from 10 days AEL | To assess the neuroprotective effects of Sp in a Parkinson's disease model, results showed that Sp improved the survivability of dopaminergic neurons, reduced oxidative stress, and restored motor abilities. | Cell Death Dis. 2020 Sep 10;11(9):739 |
BALB/c nude mice | HepG2 xenograft model | Intraperitoneal injection | 2.5, 5, 10 mg/kg | Once daily for 14 days | SC-III3 significantly inhibited tumor growth with inhibition rates of 31.2%, 38.6%, and 52.4% | BMC Cancer. 2014 Dec 19;14:987 |
Korean native chickens | High stocking density stress model | Dietary supplementation | 20 mg/kg diet | Once daily for 35 days | To investigate the effects of Scopoletin on growth performance, antioxidant activity, and meat quality of chickens under high stocking density stress. Results showed that Scopoletin supplementation decreased MDA concentration in serum and leg muscle, increased catalase, superoxide dismutase, and total antioxidant capacity, and improved meat quality and growth performance. | Foods. 2021 Jun 29;10(7):1505 |
C57BL/6 mice | Experimental autoimmune encephalomyelitis (EAE) model | Intraperitoneal injection | 50 mg/kg | Once daily for 20 days | Scopoletin significantly ameliorated the severity of EAE, reduced inflammation and demyelination in the CNS, and inhibited DC activation and Th1/Th17 cell polarization. | Front Pharmacol. 2019 Aug 2;10:863 |
Soybean (Glycine max) | Asian soybean rust model | Foliar spray | 500 μM | Single treatment | Scopoletin protected soybean from SBR by directly inhibiting Pp development rather than activating the plant defense system. | Plant J. 2019 Aug;99(3):397-413 |
Soybean (Glycine max) | Soybean cyst nematode (Heterodera glycines) infection model | Seed coating | 70:1 (w:v) seed coating | Field experiments in 2017 and 2018 | Evaluate the biocontrol effect of Scopoletin against soybean cyst nematode. Scopoletin treatment significantly reduced nematode numbers in roots and soil, and promoted soybean growth and yield. | Life (Basel). 2021 Oct 26;11(11):1143 |
Rats | Healthy rats | Intravenous and oral | Intravenous 5 mg/kg; oral 5, 10, and 20 mg/kg | Single dose | To study the pharmacokinetics and oral bioavailability of Scopoletin in rats. The results showed that the oral bioavailability was 6.62% ± 1.72% for 5 mg/kg, 5.59% ± 1.16% for 10 mg/kg, and 5.65% ± 0.75% for 20 mg/kg. | Molecules. 2015 Oct 19;20(10):18988-9001 |
Tags: Scopoletin | Gelseminic acid | Chrysatropic acid | Cholinesterase (ChE) | Apoptosis | inhibitor | 92-61-5 |
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