Typhaneoside

CAS# 104472-68-6

Typhaneoside

2D Structure

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Typhaneoside

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Chemical Properties of Typhaneoside

Cas No. 104472-68-6 SDF Download SDF
PubChem ID 5489389 Appearance Light yellow powder
Formula C34H42O20 M.Wt 770.69
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Isorhamnetin 3-(2''-rhamnosylrutinoside); 3,4',5,7-Tetrahydroxy 3'-methoxyflavone 3-(2''-rhamnosylrutinoside)
Solubility Soluble in ethanol, methanol and pyridine
Chemical Name 3-[(3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)OC6C(C(C(C(O6)C)O)O)O)O)O)O)O)O
Standard InChIKey POMAQDQEVHXLGT-QQVXUORWSA-N
Standard InChI InChI=1S/C34H42O20/c1-10-20(38)24(42)27(45)32(49-10)48-9-18-22(40)26(44)31(54-33-28(46)25(43)21(39)11(2)50-33)34(52-18)53-30-23(41)19-15(37)7-13(35)8-17(19)51-29(30)12-4-5-14(36)16(6-12)47-3/h4-8,10-11,18,20-22,24-28,31-40,42-46H,9H2,1-3H3/t10-,11-,18+,20-,21-,22+,24+,25+,26-,27+,28+,31+,32+,33-,34?/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 Typhaneoside

1 Ginkgo sp. 2 Typha sp.

Biological Activity of Typhaneoside

DescriptionTyphaneoside is possibly the main active component in the bioactive fraction of Shaofu Zhuyu decoction, Shaofu Zhuyu decoction may have direct inhibitory effects on the contractility of the mice uterus. It has an inhibitory effect on the proliferation of human umbilical arterial smooth muscle cells(HUASMC) with a wide range of effective dose but the effect is started slowly.
In vitro

Influence of typhaneoside on proliferation of human umbilical arterial smooth muscle cells.[Reference: WebLink]

Journal of Beijing University of Traditional Chinese Medicine, 2006, 29(5):307-10.

To study the influence of Typhaneoside on the proliferation of human umbilical arterial smooth muscle cells(HUASMC).
METHODS AND RESULTS:
① HUASMC were primary cultured with tissue-sticking method and determined by α-actin detection.The third to fourth generations of cells were put into the experiment.② The highest concentration of Typhaneoside was 1.00×10-5 mol/L and then diluted in multiple proportions into 11 concentration groups,and a blank control group was established.After the stimulations were given to different groups for 24,48 and 72 hours,the toxicity of Typhaneoside were detected with MTT assay.③ The highest concentration of Typhaneoside was 1.00×10-6 mol/L and then diluted in 1/4 isobaric proportion into 6 concentration groups,and a blank control group was established. After the stimulations were given to different groups for 24,48 and 72 hours,the influence of Typhaneoside on the proliferation of HUASMC was observed with MTT assay. ① The cellular staining was positive under the microscope.② Typhaneoside was not toxic to HUASMC in the concentration ranges from 9.77×10-9 mol/L to 1.00×10-5 mol/L after 24,48 and 72 hours.③ Typhaneoside did not inhibit the proliferation of HUASMC in the concentration ranges of 9.77×10-10 mol/L to 1.00×10-6 mol/L after 24 or 48 hours,but inhibited significantly the proliferation of HUASMC after 72 hours in the concentration ranges of 1.56×10-8 mol/L to 2.5×10-7 mol/L.The effect was increased along with the dose increase but there was no significant difference.The inhibitory rate reached 9.91% to 14.99%.
CONCLUSIONS:
Typhaneoside has an inhibitory effect on the proliferation of HUASMC with a wide range of effective dose but the effect is started slowly.

In vivo

Inhibitory effects of active fraction and its main components of Shaofu Zhuyu decoction on uterus contraction.[Pubmed: 20626062]

Am J Chin Med. 2010;38(4):777-87.

Shaofu Zhuyu decoction is a famous formula for treating primary dysmenorrhea in China since the Qing dynasty. In this paper, the inhibitory effects of active-guided fraction and its main bioactive components of Shaofu Zhuyu decoction on a model of non-pregnant mice uterine contraction induced by oxytocin in vitro were investigated.
METHODS AND RESULTS:
Qualitative and quantitative chemical analyses were used to correlate the chemical composition of active fraction with the spasmolytic effects. Seven ingredients in the active fraction were identified and quantified by HPLC-DAD. Three ingredients, ferulic acid, vanillic acid, and Typhaneoside, were evaluated for their effects on mice isolated uterine contraction induced by oxytocin in vitro. The ED(50) of them were 63.0 microg/ml, 57.6 microg/ml, 109.7 microg/ml, respectively. Furthermore, the inhibitory activity of the combination of these three compounds was prior to the fraction and seven compounds group. The ED(50) was 65.5 microg/ml.
CONCLUSIONS:
The data stated that ferulic acid, vanillic acid, and Typhaneoside were possibly the main active components in the bioactive fraction of Shaofu Zhuyu decoction. The study also implied that Shaofu Zhuyu decoction may have direct inhibitory effects on the contractility of the mice uterus and justified the traditional use of the prescription for treating the uterine cramping associated dysmenorrhea.

Protocol of Typhaneoside

Structure Identification
J Pharm Biomed Anal. 2012 Nov;70:636-9.

Determination of typhaneoside in rat plasma by liquid chromatography-tandem mass spectrometry.[Pubmed: 22818028]


METHODS AND RESULTS:
A highly sensitive liquid chromatography-tandem mass spectrometry method was developed and validated for the determination of Typhaneoside in rat plasma using rutin as internal standard. The analyte and rutin (internal standard) were extracted with methanol followed by a rapid isocratic elution with 10 mM ammonium acetate buffer/methanol (v:v, 20:80) on an C(18) column (150 mm × 2.1 mm I.D.) and subsequent analysis by mass spectrometry in the multi-reaction-monitoring mode. The precursor to product ion transitions of m/z 769.3 → 314.1 and m/z 609.2 → 300.1 were used to measure the analyte and the internal standard. The assay was linear over the concentration range of 0.01-10 μg/mL for Typhaneoside in rat plasma. The lower limit of quantification was 0.01 μg/mL and the extraction recovery was larger than 90.2% for Typhaneoside.
CONCLUSIONS:
The inter- and intra-day precision of the method at three concentrations was less than 6.8%. The method was firstly applied to pharmacokinetic study of Typhaneoside in rats.

Typhaneoside Dilution Calculator

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Preparing Stock Solutions of Typhaneoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2975 mL 6.4877 mL 12.9754 mL 25.9508 mL 32.4385 mL
5 mM 0.2595 mL 1.2975 mL 2.5951 mL 5.1902 mL 6.4877 mL
10 mM 0.1298 mL 0.6488 mL 1.2975 mL 2.5951 mL 3.2438 mL
50 mM 0.026 mL 0.1298 mL 0.2595 mL 0.519 mL 0.6488 mL
100 mM 0.013 mL 0.0649 mL 0.1298 mL 0.2595 mL 0.3244 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 Typhaneoside

Determination of typhaneoside in rat plasma by liquid chromatography-tandem mass spectrometry.[Pubmed:22818028]

J Pharm Biomed Anal. 2012 Nov;70:636-9.

A highly sensitive liquid chromatography-tandem mass spectrometry method was developed and validated for the determination of Typhaneoside in rat plasma using rutin as internal standard. The analyte and rutin (internal standard) were extracted with methanol followed by a rapid isocratic elution with 10 mM ammonium acetate buffer/methanol (v:v, 20:80) on an C(18) column (150 mm x 2.1 mm I.D.) and subsequent analysis by mass spectrometry in the multi-reaction-monitoring mode. The precursor to product ion transitions of m/z 769.3 --> 314.1 and m/z 609.2 --> 300.1 were used to measure the analyte and the internal standard. The assay was linear over the concentration range of 0.01-10 mug/mL for Typhaneoside in rat plasma. The lower limit of quantification was 0.01 mug/mL and the extraction recovery was larger than 90.2% for Typhaneoside. The inter- and intra-day precision of the method at three concentrations was less than 6.8%. The method was firstly applied to pharmacokinetic study of Typhaneoside in rats.

Inhibitory effects of active fraction and its main components of Shaofu Zhuyu decoction on uterus contraction.[Pubmed:20626062]

Am J Chin Med. 2010;38(4):777-87.

Shaofu Zhuyu decoction is a famous formula for treating primary dysmenorrhea in China since the Qing dynasty. In this paper, the inhibitory effects of active-guided fraction and its main bioactive components of Shaofu Zhuyu decoction on a model of non-pregnant mice uterine contraction induced by oxytocin in vitro were investigated. Qualitative and quantitative chemical analyses were used to correlate the chemical composition of active fraction with the spasmolytic effects. Seven ingredients in the active fraction were identified and quantified by HPLC-DAD. Three ingredients, ferulic acid, vanillic acid, and Typhaneoside, were evaluated for their effects on mice isolated uterine contraction induced by oxytocin in vitro. The ED(50) of them were 63.0 microg/ml, 57.6 microg/ml, 109.7 microg/ml, respectively. Furthermore, the inhibitory activity of the combination of these three compounds was prior to the fraction and seven compounds group. The ED(50) was 65.5 microg/ml. The data stated that ferulic acid, vanillic acid, and Typhaneoside were possibly the main active components in the bioactive fraction of Shaofu Zhuyu decoction. The study also implied that Shaofu Zhuyu decoction may have direct inhibitory effects on the contractility of the mice uterus and justified the traditional use of the prescription for treating the uterine cramping associated dysmenorrhea.

Description

Typhaneoside, extracted from Typha angustifolia L., Typhaneoside can inhibit the excessive autophagy of hypoxia/reoxygenation cells and increase the phosphorylation of Akt and mTOR. Typhaneoside has certain effects on the cardiovascular system, including lowering blood lipid levels, promoting antiatherosclerosis activities, as well as improving immune and coagulation function.

Keywords:

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