Senkyunolide I

CAS# 94596-28-8

Senkyunolide I

2D Structure

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3D structure

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Senkyunolide I

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Chemical Properties of Senkyunolide I

Cas No. 94596-28-8 SDF Download SDF
PubChem ID 11521428 Appearance Powder
Formula C12H16O4 M.Wt 224.3
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3Z,6S,7S)-3-butylidene-6,7-dihydroxy-4,5,6,7-tetrahydro-2-benzofuran-1-one
SMILES CCCC=C1C2=C(C(C(CC2)O)O)C(=O)O1
Standard InChIKey DQNGMIQSXNGHOA-JXQVETIVSA-N
Standard InChI InChI=1S/C12H16O4/c1-2-3-4-9-7-5-6-8(13)11(14)10(7)12(15)16-9/h4,8,11,13-14H,2-3,5-6H2,1H3/b9-4-/t8-,11+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Senkyunolide I

The roots of Ligusticum chuanxiong hort

Biological Activity of Senkyunolide I

DescriptionSenkyunolide I may be an active component of L. chuanxiong, traditionally used to treat migraine, it can protect rat brain against focal cerebral ischemia-reperfusion injury by up-regulating p-Erk1/2, Nrf2/HO-1 and inhibiting caspase 3, the neuroprotective mechanisms of itI are associated with its anti-oxidation and anti-apoptosis properties. Senkyunolide I can reduce the metamorphose damage of the RBC caused by ConA, the aggregation of the RBC can be alleviated by it.
TargetsERK | Nrf2 | HO-1 | Bcl-2/Bax | Caspase | 5-HT Receptor | NO
In vitro

Effects of Ferulic Acid,Senkyunolide H and Senkyunolide I on Erythrocytes[Reference: WebLink]

Lishizhen Medicine & Materia Medica Research, 2003, 14(12):738-9.

To study the effects of Ferulic acid、Senkyunolide H and Senkyunolide I on erythrocytes deformability and aggregation.
METHODS AND RESULTS:
Deformability and aggregation of the dog RBC were evaluated through erythrocytes deformability experiment. Ferulic acid、Senkyunolide H and Senkyunolide I can reduce the metamorphose damage of the RBC caused by ConA.
CONCLUSIONS:
The aggregation experiment also has indicated that aggregation of the RBC can be alleviated by them.

In vivo

Senkyunolide I protects rat brain against focal cerebral ischemia-reperfusion injury by up-regulating p-Erk1/2, Nrf2/HO-1 and inhibiting caspase 3.[Pubmed: 25698615]

Brain Res. 2015 Apr 24;1605:39-48.

Oxidative damage and apoptosis are critical factors contributing to neuronal death during a stroke. The aim of the present study was to evaluate the neuroprotective effects of Senkyunolide I (SEI) on focal cerebral ischemia-reperfusion (I/R) injury in rats, and investigate the underlying mechanisms.
METHODS AND RESULTS:
Male Sprague-Dawley rats were subjected to transient middle cerebral artery occlusion (tMCAO) for 2h, followed by 24h reperfusion, and then randomly assigned into four groups: Sham (sham-operated), Vehicle (tMCAO +normal saline), Senkyunolide I-L (tMCAO +SEI 36 mg/kg) and Senkyunolide I-H (tMCAO +SEI 72 mg/kg) groups. Senkyunolide I was administered intravenously, 15 min after occlusion. Neurological deficit, brain edema and infarct volume were detected after 24h of reperfusion. Histological structures of cortices and hippocampus were observed by hematoxylin and eosin staining. Biochemical indexes in the cortex were assayed by colorimetry. The impact of Senkyunolide I on the Nrf2-ARE-interaction was assayed using a luciferase reporter gene. Western blotting was performed to analysis the expressions of proteins related to anti-oxidation and apoptosis. Senkyunolide I administration significantly ameliorated the neurological deficit, reduced the infarct volume and brain edema, reversed the cerebral morphologic damage, decreased the levels of MDA and increased the activities of superoxide dismutase. Furthermore, the high dose Senkyunolide I could significantly activate the Nrf2/ARE pathway by up-regulating the phosphorylation of Erk1/2 and inducing Nrf2 nuclear translocation with enhanced HO-1 and NQO1 expressions. Additionally, treatment with Senkyunolide I remarkably promoted the ratio of Bcl-2/Bax and inhibited the expressions of cleaved caspase 3 and caspase 9.
CONCLUSIONS:
These results suggest that the neuroprotective mechanisms of Senkyunolide I are associated with its anti-oxidation and anti-apoptosis properties.

Identification of senkyunolide I metabolites in rats using ultra performance liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry.[Pubmed: 23666254]

J Pharm Biomed Anal. 2013 Jul-Aug;81-82:178-86.

Ligusticum chuanxiong Hort. (Umbelliferae) has been widely prescribed to treat cardiovascular disease in China for centuries. Senkyunolide I is one of the major bioactive components in L. chuanxiong, which shows pharmacological activities against migraines and oxidative damage.
METHODS AND RESULTS:
In this paper, ultra performance liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS) was applied for the rapid analysis of Senkyunolide I metabolites in rats after its intravenous administration. The non-metabolized parent compound and eighteen metabolites from drug-treated samples in rat plasma, urine and bile were identified. Our analysis indicated that methylation, hydration, epoxidation, glucuronidation and glutathione conjugation were the major pathways of Senkyunolide I metabolism in vivo.
CONCLUSIONS:
This study provides important information regarding the metabolism of Senkyunolide I, which will be helpful for understanding its mechanism of action. Furthermore, this work demonstrates the potential of using UPLC/Q-TOF-MS for the rapid and reliable characterization of the metabolites of natural products.

Protocol of Senkyunolide I

Animal Research

Effect and mechanism of senkyunolide I as an anti-migraine compound from Ligusticum chuanxiong.[Pubmed: 21235591 ]

J Pharm Pharmacol. 2011 Feb;63(2):261-6.

To evaluate the analgesic and anti-migraine activities of Senkyunolide I from Ligusticum chuanxiong.
METHODS AND RESULTS:
Mice were orally administered various doses of Senkyunolide I, and their pain levels were assessed in a hot-plate test and by application of acetic acid. The levels of 5-hydroxytryptamine (5-HT), 5-hydroxytryptophan (5-HTP), 5-hydroxyindoleacetic acid (5-HIAA), norepinephrine (NE) and dopamine (DA) in plasma and brain were assessed, and the monoamine turnover rates (5-HT/5-HTP, 5-HIAA/5-HT and NE/DA) were also calculated. Mice given Senkyunolide I at 16 and 32 mg/kg had significantly elevated pain thresholds in the hot-plate test, and a dose of 32 mg/kg also reduced the number of abdominal writhing responses caused by acetic acid. Significant improvements were observed in the neurotransmitter levels of the drug-treated rats compared with the saline-administered controls. Compared to the rats with nitroglycerin-induced migraines, the levels of nitric oxide in the plasma and whole brain of rats given Senkyunolide I were lower.
CONCLUSIONS:
The present study suggests that Senkyunolide I may be an active component of L. chuanxiong, traditionally used to treat migraine. The mechanism of pain relief in migraine model rats may be through adjusting the levels of monoamine neurotransmitters and their turnover rates, as well as decreasing nitric oxide levels in the blood and brain. Therefore, Senkyunolide I may be developed as a potential treatment for migraine pain.

Senkyunolide I Dilution Calculator

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Senkyunolide I Molarity Calculator

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Preparing Stock Solutions of Senkyunolide I

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.4583 mL 22.2916 mL 44.5831 mL 89.1663 mL 111.4579 mL
5 mM 0.8917 mL 4.4583 mL 8.9166 mL 17.8333 mL 22.2916 mL
10 mM 0.4458 mL 2.2292 mL 4.4583 mL 8.9166 mL 11.1458 mL
50 mM 0.0892 mL 0.4458 mL 0.8917 mL 1.7833 mL 2.2292 mL
100 mM 0.0446 mL 0.2229 mL 0.4458 mL 0.8917 mL 1.1146 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Senkyunolide I

Identification of senkyunolide I metabolites in rats using ultra performance liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry.[Pubmed:23666254]

J Pharm Biomed Anal. 2013 Jul-Aug;81-82:178-86.

Ligusticum chuanxiong Hort. (Umbelliferae) has been widely prescribed to treat cardiovascular disease in China for centuries. Senkyunolide I is one of the major bioactive components in L. chuanxiong, which shows pharmacological activities against migraines and oxidative damage. In this paper, ultra performance liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS) was applied for the rapid analysis of Senkyunolide I metabolites in rats after its intravenous administration. The non-metabolized parent compound and eighteen metabolites from drug-treated samples in rat plasma, urine and bile were identified. Our analysis indicated that methylation, hydration, epoxidation, glucuronidation and glutathione conjugation were the major pathways of Senkyunolide I metabolism in vivo. This study provides important information regarding the metabolism of Senkyunolide I, which will be helpful for understanding its mechanism of action. Furthermore, this work demonstrates the potential of using UPLC/Q-TOF-MS for the rapid and reliable characterization of the metabolites of natural products.

Senkyunolide I protects rat brain against focal cerebral ischemia-reperfusion injury by up-regulating p-Erk1/2, Nrf2/HO-1 and inhibiting caspase 3.[Pubmed:25698615]

Brain Res. 2015 Apr 24;1605:39-48.

Oxidative damage and apoptosis are critical factors contributing to neuronal death during a stroke. The aim of the present study was to evaluate the neuroprotective effects of Senkyunolide I (SEI) on focal cerebral ischemia-reperfusion (I/R) injury in rats, and investigate the underlying mechanisms. Male Sprague-Dawley rats were subjected to transient middle cerebral artery occlusion (tMCAO) for 2h, followed by 24h reperfusion, and then randomly assigned into four groups: Sham (sham-operated), Vehicle (tMCAO +normal saline), SEI-L (tMCAO +SEI 36 mg/kg) and SEI-H (tMCAO +SEI 72 mg/kg) groups. SEI was administered intravenously, 15 min after occlusion. Neurological deficit, brain edema and infarct volume were detected after 24h of reperfusion. Histological structures of cortices and hippocampus were observed by hematoxylin and eosin staining. Biochemical indexes in the cortex were assayed by colorimetry. The impact of SEI on the Nrf2-ARE-interaction was assayed using a luciferase reporter gene. Western blotting was performed to analysis the expressions of proteins related to anti-oxidation and apoptosis. SEI administration significantly ameliorated the neurological deficit, reduced the infarct volume and brain edema, reversed the cerebral morphologic damage, decreased the levels of MDA and increased the activities of superoxide dismutase. Furthermore, the high dose SEI could significantly activate the Nrf2/ARE pathway by up-regulating the phosphorylation of Erk1/2 and inducing Nrf2 nuclear translocation with enhanced HO-1 and NQO1 expressions. Additionally, treatment with SEI remarkably promoted the ratio of Bcl-2/Bax and inhibited the expressions of cleaved caspase 3 and caspase 9. These results suggest that the neuroprotective mechanisms of SEI are associated with its anti-oxidation and anti-apoptosis properties.

Effect and mechanism of senkyunolide I as an anti-migraine compound from Ligusticum chuanxiong.[Pubmed:21235591]

J Pharm Pharmacol. 2011 Feb;63(2):261-6.

OBJECTIVE: To evaluate the analgesic and anti-migraine activities of Senkyunolide I from Ligusticum chuanxiong. METHODS: Mice were orally administered various doses of Senkyunolide I, and their pain levels were assessed in a hot-plate test and by application of acetic acid. The levels of 5-hydroxytryptamine (5-HT), 5-hydroxytryptophan (5-HTP), 5-hydroxyindoleacetic acid (5-HIAA), norepinephrine (NE) and dopamine (DA) in plasma and brain were assessed, and the monoamine turnover rates (5-HT/5-HTP, 5-HIAA/5-HT and NE/DA) were also calculated. RESULTS: Mice given Senkyunolide I at 16 and 32 mg/kg had significantly elevated pain thresholds in the hot-plate test, and a dose of 32 mg/kg also reduced the number of abdominal writhing responses caused by acetic acid. Significant improvements were observed in the neurotransmitter levels of the drug-treated rats compared with the saline-administered controls. Compared to the rats with nitroglycerin-induced migraines, the levels of nitric oxide in the plasma and whole brain of rats given Senkyunolide I were lower. CONCLUSIONS: The present study suggests that Senkyunolide I may be an active component of L. chuanxiong, traditionally used to treat migraine. The mechanism of pain relief in migraine model rats may be through adjusting the levels of monoamine neurotransmitters and their turnover rates, as well as decreasing nitric oxide levels in the blood and brain. Therefore, Senkyunolide I may be developed as a potential treatment for migraine pain.

Description

Senkyunolide I, isolated from Ligusticum chuanxiong Hort, is an anti-migraine compound. Senkyunolide I protects rat brain against focal cerebral ischemia-reperfusion injury by up-regulating p-Erk1/2, Nrf2/HO-1 and inhibiting caspase 3.

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