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Qingyangshengenin

CAS# 84745-94-8

Qingyangshengenin

2D Structure

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3D structure

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Qingyangshengenin

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Chemical Properties of Qingyangshengenin

Cas No. 84745-94-8 SDF Download SDF
PubChem ID 90476678 Appearance Cryst.
Formula C28H36O8 M.Wt 500.6
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms Cynanchagenin
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] 4-hydroxybenzoate
SMILES CC(=O)C1(CCC2(C1(C(CC3C2(CC=C4C3(CCC(C4)O)C)O)OC(=O)C5=CC=C(C=C5)O)C)O)O
Standard InChIKey IMRGSWAJVVVYOW-ZCARJHNXSA-N
Standard InChI InChI=1S/C28H36O8/c1-16(29)26(33)12-13-28(35)25(26,3)22(36-23(32)17-4-6-19(30)7-5-17)15-21-24(2)10-9-20(31)14-18(24)8-11-27(21,28)34/h4-8,20-22,30-31,33-35H,9-15H2,1-3H3/t20-,21+,22+,24-,25+,26+,27-,28+/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 Qingyangshengenin

The roots of Cynanchum otophyllum

Biological Activity of Qingyangshengenin

DescriptionQingyangshengenin is a a glycoside from the roots of Cynanchum otophyllum.
In vitro

Chemical constituents of Arisaema franchetianum tubers.[Pubmed: 23106482]

J Asian Nat Prod Res. 2013;15(1):71-7.

A novel pyrrolidine alkaloid, (2R*,3S*,5S*)-N,2-dimethyl-3-hydroxy-5-(10-phenyldecyl)pyrrolidine (1), and 17 known compounds were isolated from Arisaema franchetianum Engl. (Araceae) tubers. The 17 compounds were bergenin (2), emodin (3), caffeic acid (4), nobiletin (5), 3-O-β-d-galactopyranosyl-hederagenin 28-O-β-d-xylopyranosyl(1 → 6)-β-d-galactopyranosyl ester (6), coniferin (7), Qingyangshengenin (8), methylconiferin (9), syringaresinol 4'-O-β-d-glucopyranoside (10), gagaminine (11), perlolyrine (12), (S)-1-(1'-hydroxyethyl)-β-carboline (13), 1-(β-carboline-1-yl)-3,4,5-trihydroxy-1-pentanone (14), 1-methoxycarbonyl-β-carboline (15), indolo[2,3-α]carbazole (16), 4-hydroxycinnamic acid methyl ester (17), and methyl 4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl] ferulate (18).
METHODS AND RESULTS:
The inhibitory activities of compound 1 and its N-methyl derivative (1a) against porcine respiratory and reproductive syndrome virus (PRRSV), human leukemic K562 cells, and human breast cancer MCF-7 cells were evaluated. Compounds 1 [50% inhibited concentration (IC(50)) = 12.5 ± 0.6 μM] and 1a (IC(50) = 15.7 ± 0.9 μM) were cytotoxic against K562 cells. Compound 1a also had a weak effect on PRRSV with an IC(50) value of 31.9 ± 6.0 μM [selectivity index (SI) = 18.7].

Protocol of Qingyangshengenin

Structure Identification
Steroids. 2011 Sep-Oct;76(10-11):1003-9.

Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum.[Pubmed: 21513722]


METHODS AND RESULTS:
HPLC analysis of the roots of Cynanchum otophyllum Scheind (Asclepiadaceae) led to the isolation of six new pregnane glycosides, specifically otophyllosides N-P (2-4) and otophyllosides Q-S (7-9), in addition to the identification of three known C-21 steroidal glycosides, otophylloside A (1), otophylloside B (5) and caudatin 3-O-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (6). The structure of each glycoside was determined by detailed spectroscopic analysis and chemical methods.
CONCLUSIONS:
All compounds contain Qingyangshengenin or caudatin aglycones and a straight sugar chain consisting of 4-7 hexosyl moieties with the mode of 1→4 linkage. The optically isomeric monosaccharides, D- and L-cymarose, coexisted in both otophyllosides R (8) and S (9).

Qingyangshengenin Dilution Calculator

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Preparing Stock Solutions of Qingyangshengenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9976 mL 9.988 mL 19.976 mL 39.9521 mL 49.9401 mL
5 mM 0.3995 mL 1.9976 mL 3.9952 mL 7.9904 mL 9.988 mL
10 mM 0.1998 mL 0.9988 mL 1.9976 mL 3.9952 mL 4.994 mL
50 mM 0.04 mL 0.1998 mL 0.3995 mL 0.799 mL 0.9988 mL
100 mM 0.02 mL 0.0999 mL 0.1998 mL 0.3995 mL 0.4994 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 Qingyangshengenin

Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum.[Pubmed:21513722]

Steroids. 2011 Sep-Oct;76(10-11):1003-9.

HPLC analysis of the roots of Cynanchum otophyllum Scheind (Asclepiadaceae) led to the isolation of six new pregnane glycosides, specifically otophyllosides N-P (2-4) and otophyllosides Q-S (7-9), in addition to the identification of three known C-21 steroidal glycosides, otophylloside A (1), otophylloside B (5) and caudatin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-cymarop yranosyl-(1-->4)-beta-D-cymaropyranoside (6). The structure of each glycoside was determined by detailed spectroscopic analysis and chemical methods. All compounds contain Qingyangshengenin or caudatin aglycones and a straight sugar chain consisting of 4-7 hexosyl moieties with the mode of 1-->4 linkage. The optically isomeric monosaccharides, D- and L-cymarose, coexisted in both otophyllosides R (8) and S (9).

Chemical constituents of Arisaema franchetianum tubers.[Pubmed:23106482]

J Asian Nat Prod Res. 2013;15(1):71-7.

A novel pyrrolidine alkaloid, (2R*,3S*,5S*)-N,2-dimethyl-3-hydroxy-5-(10-phenyldecyl)pyrrolidine (1), and 17 known compounds were isolated from Arisaema franchetianum Engl. (Araceae) tubers. The 17 compounds were bergenin (2), emodin (3), caffeic acid (4), nobiletin (5), 3-O-beta-d-galactopyranosyl-hederagenin 28-O-beta-d-xylopyranosyl(1 --> 6)-beta-d-galactopyranosyl ester (6), coniferin (7), Qingyangshengenin (8), methylconiferin (9), syringaresinol 4'-O-beta-d-glucopyranoside (10), gagaminine (11), perlolyrine (12), (S)-1-(1'-hydroxyethyl)-beta-carboline (13), 1-(beta-carboline-1-yl)-3,4,5-trihydroxy-1-pentanone (14), 1-methoxycarbonyl-beta-carboline (15), indolo[2,3-alpha]carbazole (16), 4-hydroxycinnamic acid methyl ester (17), and methyl 4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl] ferulate (18). The inhibitory activities of compound 1 and its N-methyl derivative (1a) against porcine respiratory and reproductive syndrome virus (PRRSV), human leukemic K562 cells, and human breast cancer MCF-7 cells were evaluated. Compounds 1 [50% inhibited concentration (IC(50)) = 12.5 +/- 0.6 muM] and 1a (IC(50) = 15.7 +/- 0.9 muM) were cytotoxic against K562 cells. Compound 1a also had a weak effect on PRRSV with an IC(50) value of 31.9 +/- 6.0 muM [selectivity index (SI) = 18.7].

Description

Qingyanshengenin (NSC 379666; compound 2), a pregnane glycoside, is a C21 steroidal aglycone isolated from the root of Cynanchumot ophyllum (Asclepiadaceae). Qingyanshengenin has anti-cancer activity.

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