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Benzoylhypacoitine

CAS# 63238-66-4

Benzoylhypacoitine

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Quality Control of Benzoylhypacoitine

Number of papers citing our products

Chemical structure

Benzoylhypacoitine

3D structure

Chemical Properties of Benzoylhypacoitine

Cas No. 63238-66-4 SDF Download SDF
PubChem ID 78358526 Appearance Powder
Formula C31H43NO9 M.Wt 573.7
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Benzoylhypacoitine
Solubility >57.3mg/ml in DMSO
Chemical Name [(2R,3R,4R,5R,6S,7S,8R,13S,16S,17R,18R)-5,7,8-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
SMILES CN1CC2(CCC(C34C2C(C(C31)C5(C6C4CC(C6OC(=O)C7=CC=CC=C7)(C(C5O)OC)O)O)OC)OC)COC
Standard InChIKey MDFCJNFOINXVSU-LUOWNJJZSA-N
Standard InChI InChI=1S/C31H43NO9/c1-32-14-28(15-37-2)12-11-18(38-3)30-17-13-29(35)25(41-27(34)16-9-7-6-8-10-16)19(17)31(36,24(33)26(29)40-5)20(23(30)32)21(39-4)22(28)30/h6-10,17-26,33,35-36H,11-15H2,1-5H3/t17-,18+,19-,20?,21+,22-,23?,24+,25-,26+,28+,29-,30?,31-/m1/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 Benzoylhypacoitine

The roots of Aconitum carmichaeli Debx.

Biological Activity of Benzoylhypacoitine

DescriptionBenzoylhypacoitine might be the principal active components which affect mitochondrial growth by Fuzi and its processed products.
TargetsImmunology & Inflammation related
In vitro

The effect of the active parts and components of Mahuangfuzixixin Decoction on RAW 264.7 cells[Reference: WebLink]

《Pharmacology and Clinics of Chinese Materia Medica》 2013-05

To research the effect of the active parts and components of Mahuang-Fuzi-Xixin Decoction on RAW 264. 7 cells which was induced by lipopolysaccharide.
METHODS AND RESULTS:
As the cells was deduced by lipopolysaccharide( 1μg / ml),the non-toxic concentrations of the active parts and components of Mahuang-Fuzi-Xixin Decoction were selected to be done,the change of viability of the cells was observed by MTT method. The total alkaloids of Mahuang( 100μg / L),volatile oil of Xixin( 2. 2μl / L) and ephedrine,methylephedrine, pseudoephedrine,Benzoylhypacoitine,benzoylaconine at the concentration of 10μg / L to 100μg / L could inhibited the proliferation of RAW 264. 7 induced by lipopolysaccharide,compared with controlled group,the differences was siginificant( P 0. 05). The others had no this effect.
CONCLUSIONS:
The effects were different of the active parts and components of Mahuang-Fuzi-Xixin Decoction on RAW 264. 7 cells.

In vivo

Safety of compound formula of fuzi for the treatment of arthralgia with cold-damp obstruction type[Reference: WebLink]

《Beijing Journal of Traditional Chinese Medicine》 2014-05

To explore the safety of compound formula of fuzi for the treatment of arthralgia with cold-damp obstruction type,so as to provide references for its safe clinical application.
METHODS AND RESULTS:
According to different TCM syndrome scores,56 cases were treated with TCM water decoction with different doses of fuzi. At predetermined time points,blood was collected to prepare the blood samples. Pharmacokinetic parameters in each sample were test to perform safety analysis. Only monoester-type Benzoylaconine( BAC),Benzoylmesaconine( BMA),Benzoylhypacoitine( BHA) and diesters-type hypaconitine( HA) were tested positive,which all had lower blood concentration than poison dosage of fuzi. The two compartment model was the best compartment model to fit the pharmacokinetic parameters,which was different from the results of animal experiment.
CONCLUSIONS:
The dosages used in this study are safe in clinic; the differences of each alkaloid metabolism are significant,which may be associated with other unknown factors.

Protocol of Benzoylhypacoitine

Structure Identification
Journal of ethnopharmacology (Impact Factor: 2.94). 03/2014; 153(3).

Spectrum-effect relationships between UPLC fingerprints and bioactivities of crude secondary roots of Aconitum carmichaeli Debeaux (Fuzi) and its three processed products on mitochondrial growth coupled with canonical correlation analysis.[Reference: WebLink]

Ethnopharmacological relevance: The crude secondary roots of Aconitum carmichaelii Debeaux (Fuzi), together with its processed products, including Yanfuzi, Heishunpian and Paofupian, are commonly applied in clinic using for thousands of years, such as collapse, syncope, rheumatic fever, painful joints and various tumors.
METHODS AND RESULTS:
To explore the different effects of Fuzi and its processed products on energy metabolism, with mitochondria as the model with the aim of guiding the clinical use of Fuzi and its products. fingerprints of Fuzi, Yanfuzi, Heishunpian and Paofupian were established by Ultra-high Performance Liquid Chromatography (UPLC) and effects of Fuzi and its processed products on rat's liver׳s mitochondrial metabolism were studied by microcalorimetry. Spectrum-effect relationships between UPLC fingerprints and energy metabolism of mitochondria were investigated using canonical correlation analysis (CCA). Because of their inherent differences in chemical compositions, the main activities of energy metabolism of mitochondria were different among Fuzi and its processed products. The potential bioactivity sequence of the tested products was Fuzi>Heishunpian>Paofupian>Yanfuzi. RESULTS of CCA showed that compounds mesaconitine, benzoylaconitine, and Benzoylhypacoitine might be the principal active components.
CONCLUSIONS:
Altogether, this work provides a general model of combination of UPLC and microcalorimetry to study the spectrum-effect relationships of Fuzi and its processed products which can offer some references for detecting principal components of traditional Chinese medicine on bioactivity to mitochondrial growth.

Benzoylhypacoitine Dilution Calculator

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Benzoylhypacoitine Molarity Calculator

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Preparing Stock Solutions of Benzoylhypacoitine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7431 mL 8.7154 mL 17.4307 mL 34.8614 mL 43.5768 mL
5 mM 0.3486 mL 1.7431 mL 3.4861 mL 6.9723 mL 8.7154 mL
10 mM 0.1743 mL 0.8715 mL 1.7431 mL 3.4861 mL 4.3577 mL
50 mM 0.0349 mL 0.1743 mL 0.3486 mL 0.6972 mL 0.8715 mL
100 mM 0.0174 mL 0.0872 mL 0.1743 mL 0.3486 mL 0.4358 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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Background on Benzoylhypacoitine

Benzoylhypaconine is a natural product.

References:
[1]. Liu X, et al. Comparative pharmacokinetics studies of benzoylhypaconine, benzoylmesaconine, benzoylaconine and hypaconitine in rats by LC-MS method after administration of Radix Aconiti Lateralis Praeparata extract and Dahuang Fuzi Decoction. Biomed Chrom

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References on Benzoylhypacoitine

Pharmacokinetics of monoester-diterpenoid alkaloids in myocardial infarction and normal rats after oral administration of Sini decoction by microdialysis combined with liquid chromatography-tandem mass spectrometry.[Pubmed:30302776]

Biomed Chromatogr. 2019 Jan;33(1):e4406.

Monoester-diterpenoid alkaloids are the main bioactive components of Sini decoction, which is a well-known traditional Chinese medicine formula for the treatment of myocardial infarction (MI) and heart failure in China. In this work, an ultra-high-performance liquid chromatography-mass spectrometry combined with microdialysis method was successfully established and applied for investigating for the first time comparative plasma pharmacokinetics of three monoester-diterpenoid alkaloids (benzoylmesaconitine, benzoylaconitine and Benzoylhypacoitine) in normal and MI rats after oral administration of Sini decoction. The statistical results of pharmacokinetic parameters demonstrated that benzoylmesaconitine, benzoylaconitine and Benzoylhypacoitine showed lower peak concentration, longer half-life, smaller area under the concentration-time curve, slower clearance, time to peak concentration and mean residence time in MI rats than in normal rats (p < 0.05), which indicated that monoester-diterpenoid alkaloids exhibited lower systemic exposure and slower elimination in the MI rats. The results provided the experimental basis for understanding the metabolic fate and therapeutic effects of Sini decoction.

A Validated LC-MS/MS Method for Simultaneous Determination of Six Aconitum Alkaloids and Seven Ginsenosides in Rat Plasma and Application to Pharmacokinetics of Shen-Fu Prescription.[Pubmed:30050589]

Evid Based Complement Alternat Med. 2018 Jun 28;2018:5107083.

A sensitive and reliable LC-MS/MS method has been developed and validated for simultaneous determination of six Aconitum alkaloids (aconitine, hypaconitine, mesaconitine, benzoylaconitine, Benzoylhypacoitine, and benzoylmesaconine) and seven ginsenosides (Rb1, Rb2, Rc, Rd, Re, Rf, and Rg1) in rat plasma after oral administration of Shen-Fu prescription. Psoralen was selected as internal standard (IS). Protein precipitation with methanol was used in sample preparation. The chromatographic separation was achieved on a CORTECS C18 column with 0.1% formic acid aqueous solution and acetonitrile as mobile phase. The flow rate was 0.3 mL/min. The detection was performed on a tandem mass system with an electrospray ionization (ESI) source in the positive ionization and multiple-reaction monitoring (MRM) mode. The calibration curves of six Aconitum alkaloids and seven ginsenosides were linear over the range of 0.1-50 and 1-500 ng/mL, respectively. The extraction recoveries of the analytes in plasma samples ranged from 64.2 to 94.1%. Meanwhile, the intra- and interday precision of the analytes were less than 14.3%, and the accuracy was in the range of -14.2% to 9.8%. The developed method was successfully applied to the pharmacokinetics of six Aconitum alkaloids and seven ginsenosides in rat plasma after oral administration of Shen-Fu prescription.

Sensitive UHPLC-MS/MS quantitation and pharmacokinetic comparisons of multiple alkaloids from Fuzi- Beimu and single herb aqueous extracts following oral delivery in rats.[Pubmed:28528229]

J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Jul 15;1058:24-31.

Aconiti Lateralis Radix Praeparata- Fritillariae Thunbergii bulbus, namely Fuzi- Beimu in Chinese, is a classic herb pair whose combined administration was prohibited according to the rule of "Eighteen antagonisms". However, incompatibility of Fuzi and Beimu has become controversial because of the application supported by many recorded ancient prescriptions and increasing modern researches and clinical practice. The present study aimed to investigate the pharmacokinetic differences of multiple alkaloids from Fuzi- Beimu and the single herb aqueous extracts following oral delivery in rats. Twelve alkaloids including aconitine, mesaconitine, hypaconitine, benzoylaconitine, benzoylmesaconitine, Benzoylhypacoitine, neoline, fuziline, talatisamine, chasmanine, peimine and peimisine in rat plasma were simultaneously quantitated by using sensitive ultra-high performance liquid chromatography- tandem mass spectrometry (UHPLC-MS/MS), with the method developed and fully validated. Plasma concentrations of the twelve alkaloids after administration were determined and pharmacokinetic parameters were compared. Significant differences were observed for all alkaloids except aconitine, mesaconitine and benzoylaconitine for Fuzi- Beimu group in comparison with the single herb group. AUC0-t and T1/2 of hypaconitine were increased significantly. AUC0-t and Cmax were increased and Tmax decreased significantly for benzoylmesaconitine and Benzoylhypacoitine. Fuziline showed significantly increased AUC0-t, Cmax and Tmax. T1/2 of neoline was notably increased. T1/2 and Tmax were significantly elevated for talatisamine while Cmax decreased. Tmax of chasmanine was significantly increased and Cmax decreased. Extremely significant increase of Tmax was found for peimisine, and significant increase of T1/2 for peimine. Results revealed that combined use of Fuzi and Beimu significantly influenced the system exposure and pharmacokinetic behaviors of multiple alkaloids from both herbs, indicating herb- herb interaction between Fuzi and Beimu.

Spectrum-effect relationships between UPLC fingerprints and bioactivities of crude secondary roots of Aconitum carmichaelii Debeaux (Fuzi) and its three processed products on mitochondrial growth coupled with canonical correlation analysis.[Pubmed:24632114]

J Ethnopharmacol. 2014 May 14;153(3):615-23.

ETHNOPHARMACOLOGICAL RELEVANCE: The crude secondary roots of Aconitum carmichaelii Debeaux (Fuzi), together with its processed products, including Yanfuzi, Heishunpian and Paofupian, are commonly applied in clinic using for thousands of years, such as collapse, syncope, rheumatic fever, painful joints and various tumors. AIM OF THE STUDY: To explore the different effects of Fuzi and its processed products on energy metabolism, with mitochondria as the model with the aim of guiding the clinical use of Fuzi and its products. fingerprints of Fuzi, Yanfuzi, Heishunpian and Paofupian were established by Ultra-high Performance Liquid Chromatography (UPLC) and effects of Fuzi and its processed products on rat's livers mitochondrial metabolism were studied by microcalorimetry. Spectrum-effect relationships between UPLC fingerprints and energy metabolism of mitochondria were investigated using canonical correlation analysis (CCA). RESULTS: Because of their inherent differences in chemical compositions, the main activities of energy metabolism of mitochondria were different among Fuzi and its processed products. The potential bioactivity sequence of the tested products was Fuzi>Heishunpian>Paofupian>Yanfuzi. RESULTS of CCA showed that compounds mesaconitine, benzoylaconitine, and Benzoylhypacoitine might be the principal active components. CONCLUSION: Altogether, this work provides a general model of combination of UPLC and microcalorimetry to study the spectrum-effect relationships of Fuzi and its processed products which can offer some references for detecting principal components of traditional Chinese medicine on bioactivity to mitochondrial growth.

Description

Benzoylhypaconine (Benzoylhypacoitine) is a monoester Aconitum alkaloid, is the main pharmacologic and toxic component.

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