Senkyunolide

CAS# 63038-10-8

Senkyunolide

Catalog No. BCN8154----Order now to get a substantial discount!

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Chemical structure

Senkyunolide

3D structure

Chemical Properties of Senkyunolide

Cas No. 63038-10-8 SDF Download SDF
PubChem ID 3085257 Appearance Oil
Formula C12H16O2 M.Wt 192.3
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S)-3-butyl-4,5-dihydro-3H-2-benzofuran-1-one
SMILES CCCCC1C2=C(C=CCC2)C(=O)O1
Standard InChIKey ZPIKVDODKLJKIN-NSHDSACASA-N
Standard InChI InChI=1S/C12H16O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,11H,2-4,6,8H2,1H3/t11-/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

The roots of Ligusticum chuanxiong hort

Biological Activity of Senkyunolide

In vitro

HPLC determination of equilibrium solubility and apparent oil/water partition coefficient of senkyunolide.[Reference: WebLink]

Chinese Journal of Pharmaceutical Analysis, 2012, 32(9):1644-1647.

To determine the equilibrium solubility of senkyunoide and its partition coefficients for the n-octanol-water/buffer solution systems,so as to provide a basis for new formulations designing.
METHODS AND RESULTS:
A high performance liquid chromatography method was established to detect the concentration of Senkyunolide .The Megres ODS(5 μm,4.6 mm×100 mm)column was adopted,the mobile phase was acetonitrile-water(1:3, v/v)at a flow rate of 1.0 mL·min-1,and the detection wavelength was 278 nm.The concentration of Senkyunolide in different pH solutions and the partition coefficients for the n-octanol-water and n-octanol-buffer solution systems were detected. The equilibrium solubility reached a maximum of 34.31 mg·mL-1in water at 37°C.Senk yunolide was instable in solvent systems pH≥9.0.Partition coefficient of Senkyunolidewas 13.43(lg P app=1.13) in the n-octanol-water system;there was no significant effect of pH to partition coefficient of Senkyunolide .
CONCLUSIONS:
The study showed that Senkyunolide is soluble,the partition coefficient of Senkyunolide is moderate,and the relative molecular mass of Senkyunolide is small.Therefore,we can explain why Senkyunolide can quickly reach into blood and brain.Senkyunolide can be predicted with a good application value.

Senkyunolide Dilution Calculator

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Preparing Stock Solutions of Senkyunolide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.2002 mL 26.001 mL 52.0021 mL 104.0042 mL 130.0052 mL
5 mM 1.04 mL 5.2002 mL 10.4004 mL 20.8008 mL 26.001 mL
10 mM 0.52 mL 2.6001 mL 5.2002 mL 10.4004 mL 13.0005 mL
50 mM 0.104 mL 0.52 mL 1.04 mL 2.0801 mL 2.6001 mL
100 mM 0.052 mL 0.26 mL 0.52 mL 1.04 mL 1.3001 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

Antiadhesive phthalides from Apium graveolens fruits against uropathogenic E. coli.[Pubmed:30904704]

J Ethnopharmacol. 2019 Mar 20;237:300-306.

ETHNOPHARMACOLOGICAL RELEVANCE: Fruits of Apium graveolens (celery) are used traditionally in Persian and European medicine for the treatment of uncomplicated urinary tract infections. AIM OF THE STUDY: The study aimed at identifying potential antiadhesive compounds from celery extracts to provide strategies for improved standardization of the herbal material. MATERIALS AND METHODS: Decoction, hydroalcoholic and acetone extracts were prepared from celery fruits. Bioassay-guided fractionation was performed by Fast Centrifugal Partition Chromatography and preparative HPLC, followed by LC-MS and NMR investigations for structure elucidation. The antiadhesive activity of extracts, fractions and purified compounds was assessed by flow cytometry, evaluating the adhesion of fluorescent-labelled uropathogenic bacteria (UPEC NU14) to T24 bladder cells; mannose served as positive control. Influence of the extract on gene expression of selected adhesins and fitness genes was monitored by qPCR. RESULTS: Concentration-dependent antiadhesive activity was found for the hydroalcoholic and even more for the acetone extract AE (IC50 85mug/mL) from celery fruits. Bioassay-guided fractionation revealed the presence of the phthalides Senkyunolide (1, inactive) and sedanenolide (2, IC50 790muM). 2 is assessed as the main antiadhesive compound, which accounts for 4.0% in the water extract, for 18% in the hydroethanolic extract and for 71% in AE. Additionally a similar phthalide, Z-ligustilide (5), was shown to exert an IC50 of 611muM. Furthermore, AE caused a significant upregulation of fimH and sfaG in free floating, non-attached UPEC and significantly down-regulated these genes in adherent bacteria. CONCLUSIONS: Phthalides were identified as the main active compounds in polar and semi-polar extracts, which exert strong antiadhesive activity against uropathogenic E. coli. The current findings support the traditional use in phytotherapy for urinary tract infections and provide a base for standardization of the herbal material.

The Efficacy and Safety of a Herbal Toothpaste in Reducing Gingivitis: A Double-Blind, Randomized, Placebo-Controlled, Parallel Allocation Clinical Trial.[Pubmed:30854006]

Evid Based Complement Alternat Med. 2019 Feb 3;2019:3764936.

Aim: To examine the efficacy and safety of the toothpaste containing Rhizoma Chuanxiong and Rhizoma Imperatae extracts in reducing gingivitis. Method: A double-blind clinical trial was conducted, in which 120 volunteers were randomly assigned to the test group (N = 60) or the control group (N = 60). Tetramethylpyrazine, Senkyunolide A, ferulic acid, and ligustilide are the main effective components of Rhizoma Chuanxiong and Rhizoma Imperatae contains the main components of cylindrin, carotene, 5-hydroxytryptamine, potassium, and calcium. The control group used placebo toothpaste containing neither Rhizoma Chuanxiong extract nor Rhizoma Imperatae extract. Plaque, gingivitis, and bleeding were assessed at the baseline, prior to the supragingival scaling, and at 4, 8, and 12 weeks. Results: During the trial, both test and control groups showed a decreasing trend compared to the baseline. At the end of 12 weeks, with respect to Gingival Index (GI), Bleeding Index (BI), and Bleeding on Probing percentage (BOP%) scores, there were significant differences between test and control groups (GI, P<0.001, BI, P<0.001, and BOP%, P<0.001, resp.). After 4 weeks of usage, there were no statistically significant differences in all of GI, BI, and BOP% scores between the two groups. However, the decrease became statistically significant at next two intervals (GI, P<0.001, BI, P<0.001, and BOP%, P<0.001, resp.) in the efficiency of GI, BI, and BOP% which was 8.04%, 11.02%, and 37.16%, respectively. There were no treatment-related adverse events reported. Conclusion: The toothpaste containing Rhizoma Chuanxiong and Rhizoma Imperatae extracts was well tolerated and significantly reduced gingivitis and bleeding after usage for 12 weeks. There was better improvement at molars, and the more serious the baseline status was, the better the efficacy was.

A network pharmacology approach to investigate the blood enriching mechanism of Danggui buxue Decoction.[Pubmed:30703496]

J Ethnopharmacol. 2019 May 10;235:227-242.

ETHNOPHARMACOLOGICAL RELEVANCE: Danggui buxue Decoction (DBD) has been frequently used to treat with blood deficiency, which consisted of Danggui (DG) and Huangqi (HQ) at a ratio of 1:5. Accumulating evidence showed that blood deficiency in traditional Chinese medicine (TCM) was similar to anemia in modern medicine. AIM OF THE STUDY: The purpose of this study was to explore its therapeutic mechanism of with network pharmacology approach. MATERIALS AND METHODS: We explored the chemical compounds of DBD and used compound ADME screening to identify the potential compounds. Targets for the therapeutic actions of DBD were obtained from the PharmMapper, Swiss, SEA and STITCH. GO analysis and pathway enrichment analysis was performed using the DAVID webserver. Cytoscape was used to visualize the compound-target-pathway network for DBD. The pharmacodynamics and crucial targets were also validated. RESULTS: Thirty-six potential active components in DBD and 49 targets which the active components acted on were identified. 47 KEGG pathways which DBD acted on were also come to light. And then, according to KEGG pathway annotation analysis, only 16 pathways seemed to be related to the blood nourishing effect of DBD, such as PI3K-AKT pathway, and so on. Only 32 targets participated in these 16 pathways and they were acted on by 29 of the 36 active compounds. Whole pharmacodynamic experiments showed that DBD had significant effects to blood loss rats. Furthermore, DBD could promote the up-regulation of hematopoietic and immune related targets and the down-regulation of inflammatory related targets. Significantly, with the results of effective rate, molecular docking and experimental validation, we predicted astragaloside IV in HQ, Senkyunolide A and Senkyunolide K in DG might be the major contributing compounds to DBD's blood enriching effect. CONCLUSION: In this study, a systematical network pharmacology approach was built. Our results provided a basis for the future study of Senkyunolide A and Senkyunolide K as the blood enriching compounds in DBD. Furthermore, combined network pharmacology with validation experimental results, the nourishing blood effect of DBD might be manifested by the dual mechanism of enhancing immunity and promoting hematopoiesis.

The Effects of Warfarin on the Pharmacokinetics of Senkyunolide I in a Rat Model of Biliary Drainage After Administration of Chuanxiong.[Pubmed:30631279]

Front Pharmacol. 2018 Dec 12;9:1461.

The aim of this study was to elucidate the effects of warfarin on Senkyunolide I in a rat model of biliary drainage after oral administration Chuanxiong extract based on pharmacokinetics. Thirty-two rats were randomly divided into four groups: CN, healthy rats after a single administration of Chuanxiong; CO, rats with biliary drainage after a single administration of Chuanxiong; WCN, healthy rats after the administration of Chuanxiong and warfarin; WCO, rats with biliary drainage after the administration of Chuanxiong and warfarin. A series of blood samples were collected at different time points before and after oral administration. An ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS) method for quantification of the main components of Chuanxiong and methyclothiazide (internal standard) have been established. The validated method was successfully applied to a comparative pharmacokinetics study. After calculated by the DAS 2.1.1 software, the pharmacokinetics parameters of Senkyunolide I showed a significant difference between the CN and CO groups, the AUC0-t, and Cmax of CO group increased by 5.45, 4.02 folds, respectively. There was a significant difference between the WCO and WCN groups, the Tmax of WCO group prolonged 67%; compared to the CN group, the AUC0-t, and Cmax of WCN group raised 4.84, 3.49 folds, respectively; the Tmax and Cmax between the CO and WCO groups also showed a significant difference. The drug warfarin significantly affected the Senkyunolide I disposition, which partly due to its enterohepatic circulation process in rat plasma after oral administration of Chuanxiong. The present study highlights an urgent evidence for drug-herb interactions.

Senkyunolide H protects against MPP(+)-induced apoptosis via the ROS-mediated mitogen-activated protein kinase pathway in PC12 cells.[Pubmed:30579107]

Environ Toxicol Pharmacol. 2019 Jan;65:73-81.

Senkyunolide H (SNH) is a phthalide isolated from the rhizome of Ligusticum chuanxiong Hort. that has been reported to have several pharmacological activities, including anti-atherosclerotic, antiproliferative, and cytoprotective effects. In this study, we investigated the neuroprotective effects and potential mechanisms of SNH against 1-methyl-4-phenylpyridinium (MPP(+))-induced oxidative stress. We demonstrated that SNH pretreatment significantly attenuated MPP(+)-induced neurotoxicity and apoptosis in PC12 cells. In addition, SNH attenuated the effect of MPP(+) on the expression of the pro-apoptotic factors Bax and caspase-3. Meanwhile, SNH prevented oxidative stress by reducing reactive oxygen species generation, mitochondrial membrane potential loss, cytochrome C release, and malondialdehyde levels while increasing antioxidant enzyme activity (e.g., superoxide dismutase, catalase, and glutathione peroxidase). In addition, SNH inhibited nuclear accumulation of nuclear factor-kappaB and c-Jun N-terminal kinase and phosphorylation p38 mitogen-activated protein kinases (MAPKs). Overall, this investigation provides novel evidence that SNH exerts neuroprotective effects via the ROS-mediated MAPK pathway and represents a potential preventive or therapeutic agent for neuronal disorders.

UPLC-MS/MS Method for the Determination of 14 Compounds in Rat Plasma and Its Application in a Pharmacokinetic Study of Orally Administered Xiaoyao Powder.[Pubmed:30274372]

Molecules. 2018 Sep 30;23(10). pii: molecules23102514.

Xiaoyao Powder (XYP), a common Chinese medicine, comprises eight traditional Chinese herbs and has been widely used clinically to treat liver damage and mental disorders. An ultra-performance liquid chromatography(-)tandem mass spectrometry method was developed to investigate the pharmacokinetics of 14 compounds (albiflorin, paeoniflorin, ferulic acid, Senkyunolide I, quercetin, isoliquiritigenin, atractylenolide III, ligustilide, atractylenolide II, liquiritin, liquiritigenin, saikosaponin c, glycyrrhizic acid, and saikosaponin a) in XYP. Naringenin was used as the internal standard. The compounds were separated using an ACQUITY UPLC(TM) BEH C18 column (1.7 mum, 50 x 2.1 mm) with a mobile phase consisting of acetonitrile and 0.1% formic acid in water at a flow rate of 0.3 mL/min. Detection was performed on a triple-quadrupole tandem mass spectrometer using multiple reaction monitoring and an electrospray ionization source in both positive and negative ionization modes. All calibration curves exhibited good linearity (r(2) > 0.9974) over the measured ranges. The intra- and inter-day precisions were within 12%, and the accuracy ranged from 89.93% to 106.64%. Extraction recovery and matrix effect results were satisfactory. The method was successfully applied in a pharmacokinetic study of the 14 compounds in rat plasma after the oral administration of XYP.

Volatile component interaction effects on compatibility of Cyperi Rhizoma and Angelicae Sinensis Radix or Chuanxiong Rhizoma by UPLC-MS/MS and response surface analysis.[Pubmed:30086506]

J Pharm Biomed Anal. 2018 Oct 25;160:135-143.

Cyperi Rhizoma (Xiangfu) combined with either Angelicae Sinensis Radix (Danggui) or Chuanxiong Rhizoma (Chuanxiong) are herb pairs that are commonly used in clinical settings. To illustrate the herb-herb interactions that occur when extracts from these herbs are obtained together, ultra-high-performance liquid chromatography coupled with triple quadrupole electrospray tandem mass spectrometry and response surface analysis were used. Volatile components, alpha-cyperone, nootkatone, ligustilide, Senkyunolide A and Senkyunolide I, were accurately identified with high precision. When Xiangfu was combined with Danggui at a 1:1 ratio, or with Chuanxiong at a 1:1 or 2:1 ratio, the dissolution rates of alpha-cyperone and nootkatone from the herbs were greatly increased, compared to those obtained from Xiangfu extract alone. The dissolution rates of ligustilide, Senkyunolide A and Senkyunolide I from Danggui or Chuanxiong changed proportionally to changes in the ratios of Xiangfu with either Danggui or Chuanxiong. Response surface analysis results presented polynomial regression equations between the dissolution of tested compounds and the corresponding input variables, including compatibility proportions and solvent dosage. Based on the predicted results from response surface analysis, a combination of Xiangfu with Chuanxiong at a ratio of near 1:1, or with Danggui at 1:2, resulted in the maximum dissolution of five volatile components. Our established method could be applied to herb-herb interaction research, and the results may provide a scientific basis for the development of Cyperi Rhizoma-Chuanxiong Rhizoma, or Cyperi Rhizoma-Angelicae Sinensis Radix-based formulas and products.

The neuroprotective effects and probable mechanisms of Ligustilide and its degradative products on intracerebral hemorrhage in mice.[Pubmed:30075428]

Int Immunopharmacol. 2018 Oct;63:43-57.

BACKGROUND: Intracerebral hemorrhage (ICH) is a common neurological emergency with higher mortality and disability rate than cerebral ischemia. Although diverse therapeutic interventions have been explored for potential neuroprotection from ICH, no effective drugs until now are available for improvement of survival rate or the life quality of survivors after ICH. Just like cerebral ischemia, inflammatory mechanism is highly thought to play a vital role in hemorrhagic brain injury. Ligustilide (LIG) has potent anti-inflammatory effects, which were shown to be closely related to its neuroprotective effects against ischemic brain injury. Senkyunolide H (SH) and Senkyunolide I (SI) are natural degradation products of LIG, which contain the mother nucleus structure of LIG as that of phthalide. However, no reports have been retrieved about the neuroprotective effects of the three phthalide compounds on ICH, especially from the perspectives of inflammatory pathways. Accordingly, this study investigated the neuroprotective potentials and mechanisms of LIG, SH and SI on experimental ICH in mice. METHODS: ICH was induced in adult male CD-1 mice by intracerebral injection of autologous blood. LIG, SH and SI, respectively, was administrated after ICH induction. Neurological deficits, brain edema, injury volume, the number of surviving/dying neurons and inflammatory gene expression were evaluated at 3days after ICH. RESULTS: Neurological deficits, brain edema, neuronal injury, microglia and astrocytes activation as well as peripheral immune cells infiltration were all significantly improved by LIG and SH, yet SI not. Moreover, the expression of TLR4, p-NF-kB p65, TNF-alpha and IL-6, was significantly downregulated by LIG and SH treatment. So was Prx1 expression and release. CONCLUSIONS: LIG and SH provide the potent neuroprotective effects against hemorrhagic stroke by inhibiting Prx1/TLR4/NF-kB signaling and the subsequent immune and neuroinflammation lesions.

Z-Ligustilide Exerted Hormetic Effect on Growth and Detoxification Enzymes of Spodoptera litura Larvae.[Pubmed:30057645]

Evid Based Complement Alternat Med. 2018 Jul 2;2018:7104513.

Plants have evolved a variety of phytochemicals to defense insect feeding, whereas insects have also evolved diverse detoxification enzymes, which are adaptively induced as a prosurvival mechanism. Herein, Z-ligustilide in Ligusticum chuanxiong Hort. was found to exhibit a similar trend in the accumulation from December to May as the occurrence of Spodoptera litura (Fabricius) larvae. Importantly, S. litura larvae feeding enhanced Z-ligustilide level in the stem and leaf (p < 0.01). Moreover, Z-ligustilide ranging from 1 to 5 mg.g(-1) exhibited remarkable larvicidal activity, antifeedant activity, and growth inhibition against S. litura larvae. The LC50 values of larvicidal activity for phthalides in L. chuanxiong were compared as follows: Z-ligustilide > levistilide A > Senkyunolide A > 3-butylidenephthalide > Senkyunolide I, implicating the critical role of conjugated structure. Notably, there was a biphasic dose response for glutathione S-transferase (GST), cytochrome P450 (CYP) 450, Acetylcholinesterase (AChE), and Carboxylesterase (CarE) activities and GSTs1, cytochrome P450 (CYP) 4S9, and CYP4M14 mRNA expression. Particularly, low dose (0.1 mg.g(-1)) of Z-ligustilide conferred the resistance of S. litura larvae against chlorpyrifos (p < 0.05). Together, our data suggest that Z-ligustilide may function in a hormetic way in the chemical defense of L. chuanxiong against S. litura larvae.

Senkyunolide A protects neural cells against corticosterone-induced apoptosis by modulating protein phosphatase 2A and alpha-synuclein signaling.[Pubmed:29983543]

Drug Des Devel Ther. 2018 Jun 25;12:1865-1879.

Background: Depression is characterized by a pathological injury to the hippocampal neurons. Senkyunolide A (SenA) is one of the major active components of Dan-zhi-xiao-yao-san, which is widely used in the treatment of depression-related disorders. Materials and methods: In the present study, it was hypothesized that the antidepressant effect of Dan-zhi-xiao-yao-san depended on the function of SenA and the authors attempted to reveal the molecular mechanism associated with the treatment. An in vitro depression model was induced using corticosterone (Cort), and the effect of SenA on the cell viability, apoptosis, and protein phosphatase 2A/alpha-synuclein (PP2A/alpha-syn) signaling was detected. To validate the mechanism driving the therapeutic effect of SenA, activity of PP2A and alpha-syn was modulated and the effect on neural cells was evaluated. Results: The results showed that SenA protects Cort-induced cell apoptosis in PC12 cells. In addition, SenA increased Cort-induced reduction of PP2A activity, while it decreased the expression of p-PP2A, alpha-syn, and p-alpha-syn (Ser129). Further, modulation of PP2A activity with specific inhibitor okadaic acid (OA) increased Cort-induced cell apoptosis, while PP2A activator D-erythro-sphingosine (SPH) exhibited an opposite effect. The neuroprotective effects of SenA on neural cells also depended on inhibition of alpha-syn function, the regulation of which would influence the activity of PP2A in a negative loop. Conclusion: Collectively, the results suggested that the neuroprotective effects of SenA were exerted by modulating activities of PP2A activities and alpha-syn. The findings partially explained the mechanism associated with the neuroprotective effect of SenA.

Simultaneous determination of eight components in Angelica sinensis based on UHPLC-ESI-MS/MS method for quality evaluation.[Pubmed:29956832]

Biomed Chromatogr. 2019 Feb;33(2):e4326.

A method employing ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) for determination of eight components including ferulic acid, Senkyunolide A, butylphthalide, ligustilide, butylidenephalide, Senkyunolide I, Senkyunolide H and levistolide A in Angelica sinensis was established. The separation was carried out using a Waters ACQUITY UHPLC BEH C18 column with gradient elution with 0.1% formic acid aqueous and acetonitrile at a flow rate of 0.4 mL/min. Good linearity was attained with R(2) of 0.9983-0.9998 in wide concentration ranges. The method had limit of detection (LOD) and quantitation (LOQ) in the range of 0.42-6.98 ng/mL and 1.39-23.28 ng/mL, respectively. Intra- and inter-day precisions varied with relative standard deviations (RSDs) from 0.33% to 0.88% and 0.37% to 1.04%, respectively. Moreover, the average recoveries were in a satisfactory range of 92.7%-102.1% with RSDs of less than 3.60%. Finally, the method was successfully applied to analyze 19 batches of A. sinensis samples grown in Min County, Gansu province, China, as well as that collected in other regions. The findings indicated that the established method is reliable and may thus be applied as a powerful tool for qualitative and quantitative analysis of components in A. sinensis, which has its implications in quality control of A. sinensis.

[Chemical constituents from Fukeqianjin formula].[Pubmed:29945383]

Zhongguo Zhong Yao Za Zhi. 2018 Jun;43(11):2300-2312.

Fukeqianjin formula, a traditional Chinese medicine compound, consists of eight Chinese medicinal materials including roots of Moghania macrophylla, roots of Rosa laevigata, aerial parts of Andrographis paniculata, caulis of Mahonia fortunei, roots of Zanthoxylum dissitum, roots of Angelica sinensis, caulis of Spatholobus suberectus, and roots of Codonopsis pilosula. The chemical constituents from Fukeqianjin formula were studied in this paper. The compounds were separated and purified by repeated column chromatographic methods including silica gel, Sephadex LH-20, macroporous adsorptive resin, and reverse phase high performance liquid chromatography. And their chemical structures were determined by spectral data analyses. Thirty-eight compounds were obtained and identified as Z-3-butylidenephthalide (1), Z-ligustilide (2), Senkyunolide I (3), Senkyunolide H (4), vanillin (5), 7-O-methylwogonin (6), wogonin (7), panicolin (8), 19-hydroxy-8(17),13-labdadien-15,16-olide (9), andrograpanin (3,14-dideoxyandrographolide; 10), andrographolide (11), 14-deoxy-11,12-didehydroandrographolide (12), isoandrographolide (13), andrographin (2'-O-methylskullcapflavone, 14), biochanin A (15), 5-hydroxy-7,8,2',5'-tetramethoxyflavone (16), formononetin (17), daidzein (18), genistein (19), benzoic acid (20), vanillic acid (21), trans-ferulic acid (22), salicylic acid (23), daidzin (24), genistein-7-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside (25), apigenin-7-O-beta-D-glucuronide (26), andrographidin C (27), apigenin-7-O-beta-D-(6"-methyl)glucuronide (28), neoandrographolide (29), genistin (30), andrographiside (31), 14-deoxy-11,12-didehydroandrographiside (32), lobetyolin (33), epicatechin (34), catechin (35), palmatine (36), berberine (37), and jatrorrhizine (38), respectively. From the results of an individual medicinal material studies, it can be judged that compounds 17, 19, 24 and 30 as flavonoids came from the roots of M. macrophylla, compounds 36-38 as alkaloids came from the caulis of M. fortunei, compounds 6-8, 14, 16, and 27 as flavonoids as well as 9-13, 29, 31, and 32 as diterpenes came from the aerial parts of A. paniculata, compound 5 as phenols came from the roots of Z. dissitum, compounds 1-4 as phthalides as well as compound 22 as phenylpropanoids came from the roots of A. sinensis, compound 33 as alkynes came from the roots of C. pilosula, compounds 15, 17-19 as flavonoids as well as compound 21 as phenolic acids came from the caulis of S. suberectus. While compounds 34 and 35 as flavanoids could come from both the caulis of S. suberectus and roots of R. laevigata. The chemical composition of traditional Chinese medicine compound can be tracked from the original sources. This work provides a demonstration for the material basis study of traditional Chinese medicine compound. Compounds 25, 26 and 28 have not so far been isolated and identified from the above-mentioned single herb.

Searching for synergistic calcium antagonists and novel therapeutic regimens for coronary heart disease therapy from a Traditional Chinese Medicine, Suxiao Jiuxin Pill.[Pubmed:29908471]

J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Aug 15;1092:220-227.

Coronary heart disease is a vital cause of morbidity and mortality worldwide, and calcium channel blockers (CCBs) are important drugs that can be used to treat cardiovascular diseases. Suxiao Jiuxin Pill (SX), a traditional Chinese medicine, is widely used as an emergency drug for coronary heart disease therapy. However, understanding its potential mechanism in intracellular calcium concentration ([Ca(2+)]i) modulation remains a challenge. To identify the active pharmacological ingredients (APIs) and reveal a novel combination therapy for ameliorating cardiovascular diseases, the ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF MS) combined with a dual-luciferase reporter [Ca(2+)]i assay system was applied. Ligustrazine, ferulic acid, Senkyunolide I, Senkyunolide A and ligustilide were identified as potential calcium antagonists in SX, and the combination of ligustrazine and Senkyunolide A showed synergetic calcium antagonistic activity. Additionally, the synergetic mechanism was further investigated by live-imaging analysis with the Ca(2+) indicator fluo-4/AM by monitoring fluorescence changes. Our results indicated that ligustrazine can block voltage-operated Ca(2+) channels (VDCCs) effectively and Senkyunolide A can exert an inhibition effect mostly on ryanodine receptors (RYRs) and partly on VDCCs. Finally, an arterial ring assay showed that the combination of ligustrazine and Senkyunolide A exerted a better vasodilatation function than using any components alone. In this study, we first revealed that a pair of natural APIs in combination acting on VDCCs and RYRs was more effective on vasodilatation by regulating [Ca(2+)]i.

Preparing the key metabolite of Z-ligustilide in vivo by a specific electrochemical reaction.[Pubmed:29663726]

J Sep Sci. 2018 Jul;41(13):2799-2807.

The key in vivo metabolites of a drug play an important role in its efficacy and toxicity. However, due to the low content and instability of these metabolites, they are hard to obtain through in vivo methods. Electrochemical reactions can be an efficient alternative to biotransformation in vivo for the preparation of metabolites. Accordingly, in this study, the metabolism of Z-ligustilide was investigated in vitro by electrochemistry coupled online to mass spectrometry. This work showed that five oxidation products of the electrochemical reaction were detected and that two of the oxidation products (Senkyunolide I and Senkyunolide H) were identified from liver microsomal incubation as well. Furthermore, after intragastric administration of Z-ligustilide in rats, Senkyunolide I and Senkyunolide H were detected in the rat plasma and liver, while 6,7-epoxyligustilide, a key intermediate metabolite of Z-ligustilide, was difficult to detect in vivo. By contrast, 6,7-epoxyligustilide was obtained from the electrochemical reaction. In addition, for the first time, 6 mg of 6,7-epoxyligustilide was prepared from 120 mg of Z-ligustilide. Therefore, electrochemical reactions represent an efficient laboratory method for preparing key drug metabolites.

Description

Senkyunolide A, isolated from Ligusticum chuanxiong Hort, has cytoprotective and antiproliferative activities. Anti-tumor activity.

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