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Hirsuteine

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BD-P0817

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 35467-43-7

  • Formula : C22H26N2O3

  • Molecular Weight : 366.45

  • PUBCHEM ID : 3037151

  • Volume : 25mg

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Catalogue Number

BD-P0817

Analysis Method

Specification

98.0%(HPLC&TLC)

Storage

-20℃

Molecular Weight

366.45

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Uncaria rhynchophylla

Structure Type

Category

SMILES

COC=C(C1CC2C3=C(CCN2CC1C=C)C4=CC=CC=C4N3)C(=O)OC

Synonyms

Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-α-(methoxymethylene)-, methyl ester, (αZ,2S,3R,12bS)-/delta18-Hirsutine/(E)-16,17,18,19-Tetradehydro-17-methoxy-17,18-secoyohimban-16-carboxylic AcidMethyl Ester/methyl (3beta,16E)-16-(methoxymethylidene)coryn-18-en-17-oate/Methyl (16Z)-16-(methoxymethylene)coryn-18-en-17-oate/methyl (E)-2-[(2S,3R,12bR)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

IUPAC Name

Applications

Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death. PUMID/DOI:DOI:10.1080 / 10286020.2014.918109 J Asian Nat Prod Res. 2014;16(8):876-83. One new alkaloid, 4-geissoschizine N-oxide methyl ether (1), was isolated from the EtOH extract of the hook-bearing branch of Uncariarhynchophylla, together with 10 known alkaloids, 3-epi-geissoschizine methyl ether (2) isolated from U.rhynchophylla for the first time, geissoschizine methyl ether (3), 4-hirsuteine N-oxide (4), hirsuteine (5), hirsutine (6), 3α-dihydro-cadambine (7), 3β-isodihydro-cadambine (8), cadambine (9), strictosamide (10), and akuammigine (11). The structures were elucidated by spectroscopic methods including UV, ESI-QTOF MS, NMR, and circular dichroism experiments. Neuroprotective effects of 1-9 were investigated against 3 mM glutamate-induced HT22 cell death. The activity assay showed that 2, 3, 5, and 6 exhibited potent neuroprotective effects against glutamate-induced HT22 cell death. However, only weak neuroprotective activities were observed for 1, 4, 7, 8, and 9. Non-competitive antagonism by hirsuteine of nicotinic receptor-mediated dopamine release from rat pheochromocytoma cells. PUMID/DOI:8320880 Jpn J Pharmacol. 1993 Apr;61(4):351-6. Effects of hirsuteine, an indole alkaloid extracted from Uncaria genus, on nicotine- and high K-induced responses were investigated in rat pheochromocytoma PC12 cells. Hirsuteine (300 nM-10 microM) inhibited dopamine release evoked by 100 microM nicotine in a concentration-dependent manner. Hirsuteine did not produce a parallel shift of the concentration-response relationship curve for nicotine, but reduced maximal dopamine release. Dopamine release evoked by 60 and 155 mM KCl was also inhibited by hirsuteine, but the concentration necessary for significant inhibition was higher (more than 10 microM). Under whole cell voltage-clamp, hirsuteine reversibly inhibited inward currents activated by 100 microM nicotine. The current inhibition was slightly accelerated by hyperpolarization. The results suggest that hirsuteine non-competitively antagonizes nicotine-evoked dopamine release by blocking ion permeation through nicotinic receptor channel complexes. The blockade of Ca channels, which are activated during nicotine-evoked depolarization, may not play a major role in the antagonism. Evaluation of the protective effects of alkaloids isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death in cultured cerebellar granule cells from rats. PUMID/DOI:10454049 J Pharm Pharmacol. 1999 Jun;51(6):715-22. We have previously shown that an aqueous extract of the hooks and stems of Uncaria sinensis (Oliv.) Havil., Uncariae Uncus Cum Ramulusis, protects against glutamate-induced neuronal death in cultured cerebellar granule cells by inhibition of Ca2+ influx. Because it is not known which components of Uncaria sinensis are active, in this study we have evaluated, by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) staining, the neuroprotective effects of the oxyindole alkaloids corynoxeine, rhynchophylline, isorhynchophylline and isocorynoxeine, and the indole alkaloids geissoschizine methyl ether, hirsuteine and hirsutine, isolated from the hooks and stems of Uncaria sinensis, on glutamate-induced cell death. We also investigated the inhibitory effects of the compounds on 45Ca2+ influx in cultured rat cerebellar granule cells. Cell viability evaluated by the MTT assay was significantly increased by application of rhynchophylline (10(-3) M), isorhynchophylline (10(-4)-10(-3) M), isocorynoxeine (10(-4)-10(-3) M), hirsuteine (10(-4)-3 x 10(-4) M) or hirsutine (10(-4)-3 x 10(-4) M) compared with exposure to glutamate only, with the effect of isorhynchophylline being the strongest. The increased 45Ca2+ influx into cells induced by glutamate was significantly inhibited by administration of rhynchophylline (10(-3) M), isorhynchophylline (3 x 10(-4)-10(-3) M), isocorynoxeine (3 x 10(-4)-10(-3) M), geissoschizine methyl ether (10(-3) M), hirsuteine (3 x 10(-4)-10(-3) M) or hirsutine (3 x 10(-4)-10(-3) M). These results suggest that oxyindole alkaloids such as isorhynchophylline, isocorynoxeine and rhynchophylline and indole alkaloids such as hirsuteine and hirsutine are the active components of the hooks and stems of Uncaria sinensis which protect against glutamate-induced neuronal death in cultured cerebellar granule cells by inhibition of Ca2+ influx. Vasodilative effects of indole alkaloids obtained from domestic plants, Uncaria rhynchophylla Miq. and Amsonia elliptica Roem. et Schult PUMID/DOI:2328929 Nihon Yakurigaku Zasshi. 1990 Feb;95(2):47-54. Vasodilative effects of hirsutine (HS) and hirsuteine (HST) which were isolated from the domestic plant Uncaria rhynchophylla Miq. and beta-yohimbine (beta-Y) which was isolated from the domestic plant Amsonia elliptica Roem. et Schult. were carried out. In the hind-limb artery of anesthetized dogs, intra-arterial administration of HS, HST and beta-Y caused a vasodilatation. The vasodilative potency of HS was somewhat stronger than that of HST, and the potency of both alkaloids was approximately equal to that of papaverine. The vasodilative effect of beta-Y was similar to that of yohimbine, which is considered to be derived from its alpha-adrenoceptor blocking effect, and the potency of both alkaloids was approximately the same, while the effect of beta-Y was stronger than that of papaverine. In the coronary artery, HS showed a vasodilatation and its potency was weaker than that of papaverine. Also, HS showed the same effect in the cerebral artery, and the potency of HS was approximately the same as that of papaverine. These results suggest that the mode of the vasodilative effect induced by HS may partly differ from that of papaverine.

Density

1.2±0.1 g/cm3

Solubility

Methanol; Acetone

Flash Point

276.3±30.1 °C

Boiling Point

533.2±50.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

TZUGIFAYWNNSAO-AZQGJTAVSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:35467-43-7) 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

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;

PMID

26151135

Abstract

CONTEXT:
Yokukansan (YKS) is a traditional Japanese herbal medicine called kampo medicine in Japan. Its extract comprises seven crude drugs: Atractylodis lanceae rhizoma, Poria, Cnidii rhizoma, Uncariae uncis cum ramulus, Angelicae radix, Bupleuri radix, and Glycyrrhizae radix. YKS is used to treat neurosis, insomnia, as well as behavioral and psychological symptoms of dementia.

OBJECTIVE:
To confirm the exposure and pharmacokinetics of the active components of YKS in healthy volunteers.

DESIGN, SETTING, AND PARTICIPANTS:
A randomized, open-label, 3-arm, 3-period, crossover trial was conducted on 21 healthy Japanese volunteers at the Kochi Medical University between May 2012 and November 2012.

INTERVENTIONS:
Single oral administration of YKS (2.5 g, 5.0 g, or 7.5 g/day) during each period.

MAIN OUTCOME MEASURE:
Plasma concentrations of three active compounds in YKS, namely 18β-glycyrrhetinic acid (GA), geissoschizine methyl ether (GM), and hirsuteine (HTE).

RESULTS:
The mean maximum plasma concentrations (Cmax) of GM and HTE increased dose-dependently (ranges: 0.650-1.98 ng/mL and 0.138-0.450 ng/mL, respectively). The times to maximum plasma concentration after drug administration (tmax) were 0.500 h for GM and 0.975-1.00 h for HTE. The apparent elimination half-lives (t1/2) were 1.72-1.95 h for GM and 2.47-3.03 h for HTE. These data indicate the rapid absorption and elimination of GM and HTE. On the other hand, the Cmax, tmax, and t1/2 of GA were 57.7-108 ng/mL, 8.00-8.01 h, and 9.39-12.3 h, respectively.

CONCLUSION:
We demonstrated that pharmacologically active components of YKS are detected in humans. Further, we determined the pharmacokinetics of GM, HTE, and GA. This information will be useful to elucidate the pharmacological effects of YKS.

TRIAL REGISTRATION:
Japan Pharmaceutical Information Center JAPIC CTI-121811.

Title

Pharmacokinetics of Active Components of Yokukansan, a Traditional Japanese Herbal Medicine after a Single Oral Administration to Healthy Japanese Volunteers: A Cross-Over, Randomized Study.

Author

Kitagawa H1, Munekage M1, Ichikawa K2, Fukudome I1, Munekage E1, Takezaki Y1, Matsumoto T3, Igarashi Y4, Hanyu H5, Hanazaki K1.

Publish date

2015 Jul 7;