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Hirsutine

$1,255

  • Brand : BIOFRON

  • Catalogue Number : BD-P0810

  • Specification : 99.0%(HPLC)

  • CAS number : 7729-23-9

  • Formula : C22H28N2O3

  • Molecular Weight : 368.47

  • PUBCHEM ID : 3037884

  • Volume : 25mg

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Catalogue Number

BD-P0810

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC)

Storage

2-8°C

Molecular Weight

368.47

Appearance

Powder

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=CC=CC=C34

Synonyms

Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(methoxymethylene)-, methyl ester, (αE,2S,3R,12bR)-/Methyl (3β,16E)-16-(methoxymethylene)corynan-17-oate/Hirsutine/Methyl (3β,16E)-17-methoxycoryn-16-en-16-carboxylate/methyl (3β,16E)-16-(methoxymethylidene)corynan-17-oate

IUPAC Name

methyl (E)-2-[(2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Applications

Hirsutine, an indole alkaloid of Uncaria rhynchophylla, exhibits anti-cancer activity. Hirsutine induces apoptosis and is a potent Dengue virus inhibitor exhibiting low cytotoxicity[1][2][3].

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethanol; Acetone

Flash Point

275.4±30.1 °C

Boiling Point

531.7±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20+/m0/s1

InChl Key

NMLUOJBSAYAYEM-AZQGJTAVSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:7729-23-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31328320

Abstract

INTRODUCTION:
Hirsutine and hirsuteine are the main pharmacological activity ingredients of Uncaria rhynchophylla (UR), playing an important role in treating mental and cardiovascular diseases, such as Alzheimer’s disease, hypertension, Parkinson’s disease, potential anti-cancer activities and so on.

OBJECTIVE:
To develop a cyclodextrin-modified micellar electrokinetic capillary chromatography (CD-MEKC) method for the simultaneous separation and determination of hirsutine and hirsuteine from UR and its formulations.

METHODOLOGY:
The optimal method was developed by investigating influences of significant factors on the separation, and this method was successfully applied for the determination of hirsutine and hirsuteine in UR and its formulations.

RESULTS:
The optimal background electrolyte (BGE) consisted of 40 mM sodium dihydrogen phosphate (pH 7.0), 150 mM 2,6-dimethyl-β-cyclodextrin (DM-β-CD), 3 mM mono-(6-ethylenediamine-6-deoxy)-β-cyclodextrin (ED-β-CD), and 30 mM sodium cholate (SC). Under these conditions, hirsutine and hirsuteine were successfully separated within 13 min at the separation voltage of 15 kV, temperature of 25°C and the detection wavelength of 224 nm. For the analytes, linear calibration curves were performed within the range 5.0-160.0 μg/mL. The limit of detection (LOD, S/N = 3) and the limit of quantitation (LOQ, S/N = 10) were 0.41, 1.42 μg/mL for hirsutine and 0.60, 2.17 μg/mL for hirsuteine, respectively. The recoveries of three samples were from 97.9% to 102.3%.

CONCLUSION:
The method was successfully applied to the determination of hirsutine and hirsuteine in UR and its formulations. Meanwhile, it provides an effective reference of the quality control of UR and its formulations.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

cyclodextrin-modified micellar electrokinetic capillary chromatography; hirsuteine; hirsutine; simultaneous determination

Title

Simultaneous separation and determination of hirsutine and hirsuteine by cyclodextrin-modified micellar electrokinetic capillary chromatography.

Author

Wang M1, Guo J1, Wang Z1, Zhang G1, Yu H2, Chang R1, Chen A1.

Publish date

2020 Jan

PMID

29789524

Abstract

Hirsutine extracted from Uncaria rhynchophylla has been shown to exhibit anti-cancer activity. However, the molecular mechanism by which hirsutine exhibits anti-lung cancer activity remains unclear. In the present study, we showed that hirsutine induces apoptosis in human lung cancer cells via loss of mitochondrial membrane potential (∆ψm), adenosine triphosphate (ATP) depletion, ROS production, as well as cytochrome c release. Dephosphorylation of GSK3β is involved in hirsutine-mediated mitochondrial permeability transition pore (mPTP) opening through ANT1/CypD interaction. Mechanistic study revealed that interruption of ROCK1/PTEN/PI3K/Akt signaling pathway plays a critical role in hirsutine-mediated GSK3β dephosphorylation and mitochondrial apoptosis. Our in vivo study also showed that hirsutine effectively inhibits tumor growth in a A549 xenograft mouse model through ROCK1/PTEN/PI3K/Akt signaling-mediated GSK3β dephosphorylation and apoptosis. Collectively, these findings suggest a hierarchical model in which induction of apoptosis by hirsutine stems primarily from activation of ROCK1 and PTEN, inactivation of PI3K/Akt, leading in turn to GSK3β dephosphorylation and mPTP opening, and culminating in caspase-3 activation and apoptosis. These findings could provide a novel mechanistic basis for the application of hirsutine in the treatment of human lung cancer.

Title

Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells.

Author

Zhang R1, Li G1, Zhang Q1, Tang Q1, Huang J1, Hu C1, Liu Y1, Wang Q1, Liu W1, Gao N2, Zhou S3.

Publish date

2018 May 22

PMID

29747744

Abstract

BACKGROUND:
We recently focused on alkaloids in Uncaria hook (a constituent of the Kampo medicine, yokukansan) and identified the pharmacological action of geissoschizine methyl ether on several G protein-coupled receptors. However, the functions of other identified alkaloids in Uncaria hook, including hirsutine, hirsuteine, rhynchophylline, isorhynchophylline, corynoxeine, isocorynoxeine, are not clear.

PURPOSE:
To evaluate the effect of seven alkaloids in Uncaria hook (hirsutine, hirsuteine, rhynchophylline, isorhynchophylline, corynoxeine, isocorynoxeine and geissoschizine methyl ether) on the hydroxytryptamine type-3 (5-HT3) receptor ion channel.

STUDY DESIGN:
We examined the effect of these alkaloids on the current of human 5-HT3 receptors expressed in Xenopus laevis oocytes.

METHODS:
The human 5-HT3A subunit alone for the 5-HT3A receptor, or 5-HT3A and 5-HT3B subunits for the 5-HT3AB receptor, were expressed in Xenopus laevis oocytes. The 5-HT current was measured with or without alkaloid application using a two-electrode voltage clamp.

RESULTS:
Each alkaloid, except for geissoschizine methyl ether, weakly inhibited the 5-HT-mediated 5-HT3A and/or 5-HT3AB receptor current, but co-application of these seven alkaloids inhibited the current strongly.

CONCLUSION:
Each alkaloid contributes to antagonism of the 5-HT3 receptor.

Copyright © 2018 Elsevier GmbH. All rights reserved.

KEYWORDS

5-HT(3); Antagonist; Ion channel; Serotonin receptor; Yi-Gan San; Yokukansan

Title

Yokukansan contains compounds that antagonize the 5-HT3 receptor.

Author

Nakamura Y1, Ishida Y2, Kondo M2, Shimada S2.

Publish date

2018 Apr 1