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Prim-O-glucosylcimifugin

CAS# 80681-45-4

Prim-O-glucosylcimifugin

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Chemical structure

Prim-O-glucosylcimifugin

3D structure

Chemical Properties of Prim-O-glucosylcimifugin

Cas No. 80681-45-4 SDF Download SDF
PubChem ID 14034912 Appearance White powder
Formula C22H28O11 M.Wt 468.45
Type of Compound Polyphenols Storage Desiccate at -20°C
Synonyms Cimifugin 7-glucoside; Prim-O-glucosyl cimifugin;prime-O-glucosylcimifugin
Solubility DMSO : ≥ 150 mg/mL (320.20 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one
SMILES CC(C)(C1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)COC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey XIUVHOSBSDYXRG-UVTAEQIVSA-N
Standard InChI InChI=1S/C22H28O11/c1-22(2,28)15-5-10-12(32-15)6-13-16(20(10)29-3)11(24)4-9(31-13)8-30-21-19(27)18(26)17(25)14(7-23)33-21/h4,6,14-15,17-19,21,23,25-28H,5,7-8H2,1-3H3/t14-,15+,17-,18+,19-,21-/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 Prim-O-glucosylcimifugin

1 Saposhnikovia sp.

Biological Activity of Prim-O-glucosylcimifugin

DescriptionPrim-O-glucosylcimifugin is main medicinal component of the traditional Chinese drug Saposhnikovia divaricata, has inhibition on NO production and DPPH free radical, it can inhibit the proliferation of smooth muscle cell stimulated by TNF-α and increase the proportion of G0/G1 phase.
TargetsTNF-α | NO
In vitro

Effect of prim-o-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con on proliferation of smooth muscle cell stimulated by TNF-alpha.[Pubmed: 19066065]

Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2157-60.

To investigate the effect of Prim-O-glucosylcimifugin and 4'-O-p-D-glucosyl-5-O-methylvisa-mminol con on the proliferation of smooth muscle cell stimulated by TNF-alpha.
METHODS AND RESULTS:
The primary cell culture method of smooth muscle cell (SMC) was established by attachment-block. The SMC was identificated by immunochemistry method, and the growth curve was drawn by cytometry. The third generation of SMC was adopted in the experiment. The effect of prim-O-glucosylcimif-ugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con on the proliferation and cell cycle of SMC was investigated by MTT and flow cytometry respectively. TNF-alpha of 5 micro g x L(-1) can stimulate the proliferation of SMC and increase the proportion of G2 phase and S phase in cell cycle which has great significant difference (P < 0.01) compared with control. The three dose groups of Prim-O-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisammin-ol con can inhibit the proliferation of SMC and increase the proportion of G0/G1 phase, which has great significant difference (P < 0.01) compared with model group.
CONCLUSIONS:
Prim-O-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con can inhibit the proliferation of SMC stimulated by TNF-alpha.

In vivo

Studies on effects of calycosin-7-O-β-D-glucoside on prim-O-glucosylcimifugin and cimifugin in vivo pharmacokinetics.[Pubmed: 25911821]

Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(23):4669-74.

Study on the effects of Astragali Radix main active flavone calycosin-7-O-β-D-glucoside on Saposhnikoviae Radix main active ingredients Prim-O-glucosylcimifugin and cimifugin, a UPLC-MS/MS method for simultaneous determination of Prim-O-glucosylcimifugin and cimifugin in rat plasma was established, and the comparative pharmacokinetics of Prim-O-glucosylcimifugin and cimifugin after oral administration of Prim-O-glucosylcimifugin and calycosin-7-O-β-D-glucoside-Prim-O-glucosylcimifugin to rats were carried out, which might be conductive in exploring the rationality of Astragali Radix - Saposhnikoviae Radix herb couple. Twelve male SD rats were divided into two groups. Prim-O-glucosylcimifugin and cimifugin in rat plasma of different time points after oral administration of Prim-O-glucosylcimifugin and calycosin-7-O-β-D-glucoside - Prim-O-glucosylcimifugin to rats were determinated. And the main pharmacokinetic parameters were investigated using DAS 3. 2. 4. The established method was rapid, accurate and sensitive for simultaneous determination of Prim-O-glucosylcimifugin and cimifugin in rat plasma. The analysis was performed on a Waters Acquity BEH C18 column (2.1 mm x 100 mm, 1.7 μm) with the mixture of acetonitrile and 0.1% formic acid/water as mobile phase, and the gradient elution at a flow rate of 0.3 mL x min(-1). The analytes were detected by tandem mass spectrometry with the electrospray ionization (ESI) source and in the multiple reaction monitoring (MRM) mode. Compared with Prim-O-glucosylcimifugin group, the AUC(0-t)., and AUC(0-∞) of p-O-glucosylcimifugin as well as the C(max) of cimifugin significantly increased (P < 0.05) in calycosin-7-O-β-D-glucoside-Prim-O-glucosylcimifugin group. Calycosin-7-O-β-D-glucoside could enhance the absorption of Prim-O-glucosylcimifugin and cimifugin and improve the bioavailability, explaining preliminarily the rationality of Astragali Radix-Saposhnikoviae Radix herb couple.

Protocol of Prim-O-glucosylcimifugin

Animal Research

Pharmacokinetic Interaction of astragaloside IV with atractylenolide I and prim-O-glucosylcimifugin in male Sprague Dawley rats.[Pubmed: 24452462]

Planta Med. 2014 Feb;80(2-3):187-92.

Astragaloside IV, atractylenolide I, and Prim-O-glucosylcimifugin are main medicinal components of the traditional Chinese medicine prescription Yu-ping-feng which is composed of three herbs: Astragalus membranaceus, Atractylodes macrocephala, and Saposhnikovia divaricata. This study is aimed to assess the influence of atractylenolide I and Prim-O-glucosylcimifugin on the pharmacokinetic profile of astragaloside IV so as to investigate the pharmacokinetic mechanisms of the Yu-ping-feng prescription.
METHODS AND RESULTS:
Fifteen Sprague Dawley rats were randomized to three groups; astragaloside IV, astragaloside IV plus atractylenolide I, and a combination of astragaloside IV, atractylenolide I, and Prim-O-glucosylcimifugin were respectively administered to rats of these three groups via intragastric gavage. Serum samples were collected at different times after drug administration, and serum concentrations of astragaloside IV and atractylenolide I were simultaneously detected using HPLC-electrospray ionization-MS. Compared with administration of astragaloside IV alone, concentrations of astragaloside IV in the serum were significantly increased when it was given in combination with atractylenolide I or atractylenolide I+Prim-O-glucosylcimifugin, with higher values for Cmax (p = 0.019 and p = 0.033 compared with astragaloside IV + atractylenolide I and astragaloside IV + atractylenolide I + Prim-O-glucosylcimifugin groups, respectively) and AUC (p = 0.0052 and p = 0.0047 compared with astragaloside IV + atractylenolide I and astragaloside IV + atractylenolide I + Prim-O-glucosylcimifugin groups, respectively).
CONCLUSIONS:
Improvement in mean oral Cmax and mean systemic serum exposure because of the pharmacokinetic interaction between astragaloside IV and atractylenolide I might explain the rationale for the use of multiple herbs in Yu-ping-feng and of combinations of A.membranaceus and A. macrocephala.

Structure Identification
J Asian Nat Prod Res. 2012;14(9):886-96.

Biotransformation of prim-O-glucosylcimifugin by human intestinal flora and its inhibition on NO production and DPPH free radical.[Pubmed: 22917273]

Prim-O-glucosylcimifugin (PGCN), a highest content chromone in the roots of Saposhnikovia divaricata, was incubated with human intestinal flora (HIF), and two biotransformation products were obtained from the incubated solution by chromatographic methods.
METHODS AND RESULTS:
The chemical structures of the two biotransformation products were elucidated as cimifugin (CN) and 5-O-methylvisamminol (MVL), respectively, on the basis of NMR and MS data. The biotransformation product CN was formed through a deglucosylation of Prim-O-glucosylcimifugin by β-glucosidase secreted from the HIF, and then the hydroxymethyl group of CN was reduced to lead to occurrence of MVL. All of these compounds were evaluated for their effect on the inhibition of nitric oxide production induced by lipopolysaccharide in macrophage cell line RAW 264.7 and for 1,1-diphenyl-2-picrylhydrazyl free-radical scavenging activity in cell-free bioassay system.

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Preparing Stock Solutions of Prim-O-glucosylcimifugin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1347 mL 10.6735 mL 21.347 mL 42.694 mL 53.3675 mL
5 mM 0.4269 mL 2.1347 mL 4.2694 mL 8.5388 mL 10.6735 mL
10 mM 0.2135 mL 1.0673 mL 2.1347 mL 4.2694 mL 5.3367 mL
50 mM 0.0427 mL 0.2135 mL 0.4269 mL 0.8539 mL 1.0673 mL
100 mM 0.0213 mL 0.1067 mL 0.2135 mL 0.4269 mL 0.5337 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 Prim-O-glucosylcimifugin

Prim-O-glucosylcimifugin exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by through regulating JAK2/STAT3 signaling.

In Vitro:Prim-O-glucosylcimifugin (POG) is the highest content chromone and one of the major active constituents in Radix Saposhnikoviae (RS). Prim-O-glucosylcimifugin exerts anti-inflammatory effects in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 expression by inhibiting JAK2/STAT3 signaling. The cytotoxicity of Prim-O-glucosylcimifugin is measured to LPS-activated Raw 264.7 macrophages. Raw 264.7 macrophages are treated with LPS (1 μg/mL) and increasing concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h and cell viability is evaluated by CCK-8 assay. Cell viability is not significantly affected after 24 h and exposure to 15-100 μg/mL Prim-O-glucosylcimifugin as compared with DMSO-treated cells (control). To investigate the anti-inflammatory effect of Prim-O-glucosylcimifugin, whether Prim-O-glucosylcimifugin can affect NO synthesis is examined in LPS-activated RAW 264.7 cells. Macrophages are treated with LPS (1 μg/mL) and various concentrations of Prim-O-glucosylcimifugin (15, 50, and 100 μg/mL) for 24 h. No concentrations are measured in the culture supernatants by Griess reaction. The concentrations of NO in the culture supernatants are markedly increased in response to LPS exposure, and Prim-O-glucosylcimifugin significantly inhibits LPS-induced NO production in a concentration-dependent manner[1].

In Vivo:Bronchoalveolar lavage fluid (BALF) is collected at 7 h after lipopolysaccharide (LPS) administration and the cytokine levels in BALF are measured by ELISA. The levels of TNF-α, IL-1β and IL-6 in BALF are increased dramatically compared with control group. However, pretreatment with Prime-O-glucosylcimifugin (2.5, 5 or 10 mg/kg) significantly down-regulates the levels of TNF-α, IL-1β and IL-6 in a dose-dependent manner (P<0.05, P<0.01)[1].

References:
[1]. Zhou J, et al. Prim-O-glucosylcimifugin Attenuates Lipopolysaccharideinduced Inflammatory Response in RAW 264.7 Macrophages. Pharmacogn Mag. 2017 Jul-Sep;13(51):378-384. [2]. Chen N, et al. Prime-O-glucosylcimifugin attenuates lipopolysaccharide-induced acute lung injury in mice. Int Immunopharmacol. 2013 Jun;16(2):139-47.

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References on Prim-O-glucosylcimifugin

[Effect of prim-o-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con on proliferation of smooth muscle cell stimulated by TNF-alpha].[Pubmed:19066065]

Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2157-60.

OBJECTIVE: To investigate the effect of Prim-O-glucosylcimifugin and 4'-O-p-D-glucosyl-5-O-methylvisa-mminol con on the proliferation of smooth muscle cell stimulated by TNF-alpha. METHOD: The primary cell culture method of smooth muscle cell (SMC) was established by attachment-block. The SMC was identificated by immunochemistry method, and the growth curve was drawn by cytometry. The third generation of SMC was adopted in the experiment. The effect of prim-O-glucosylcimif-ugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con on the proliferation and cell cycle of SMC was investigated by MTT and flow cytometry respectively. RESULT: TNF-alpha of 5 micro g x L(-1) can stimulate the proliferation of SMC and increase the proportion of G2 phase and S phase in cell cycle which has great significant difference (P < 0.01) compared with control. The three dose groups of Prim-O-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisammin-ol con can inhibit the proliferation of SMC and increase the proportion of G0/G1 phase, which has great significant difference (P < 0.01) compared with model group. CONCLUSION: Prim-O-glucosylcimifugin and 4'-O-beta-D-glucosyl-5-O-methylvisamminol con can inhibit the proliferation of SMC stimulated by TNF-alpha.

[Studies on effects of calycosin-7-O-beta-D-glucoside on prim-O-glucosylcimifugin and cimifugin in vivo pharmacokinetics].[Pubmed:25911821]

Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(23):4669-74.

Study on the effects of Astragali Radix main active flavone calycosin-7-O-beta-D-glucoside on Saposhnikoviae Radix main active ingredients Prim-O-glucosylcimifugin and cimifugin, a UPLC-MS/MS method for simultaneous determination of Prim-O-glucosylcimifugin and cimifugin in rat plasma was established, and the comparative pharmacokinetics of Prim-O-glucosylcimifugin and cimifugin after oral administration of Prim-O-glucosylcimifugin and calycosin-7-O-beta-D-glucoside-Prim-O-glucosylcimifugin to rats were carried out, which might be conductive in exploring the rationality of Astragali Radix - Saposhnikoviae Radix herb couple. Twelve male SD rats were divided into two groups. Prim-O-glucosylcimifugin and cimifugin in rat plasma of different time points after oral administration of Prim-O-glucosylcimifugin and calycosin-7-O-beta-D-glucoside - Prim-O-glucosylcimifugin to rats were determinated. And the main pharmacokinetic parameters were investigated using DAS 3. 2. 4. The established method was rapid, accurate and sensitive for simultaneous determination of Prim-O-glucosylcimifugin and cimifugin in rat plasma. The analysis was performed on a Waters Acquity BEH C18 column (2.1 mm x 100 mm, 1.7 mum) with the mixture of acetonitrile and 0.1% formic acid/water as mobile phase, and the gradient elution at a flow rate of 0.3 mL x min(-1). The analytes were detected by tandem mass spectrometry with the electrospray ionization (ESI) source and in the multiple reaction monitoring (MRM) mode. Compared with Prim-O-glucosylcimifugin group, the AUC(0-t)., and AUC(0-infinity) of p-O-glucosylcimifugin as well as the C(max) of cimifugin significantly increased (P < 0.05) in calycosin-7-O-beta-D-glucoside-Prim-O-glucosylcimifugin group. Calycosin-7-O-beta-D-glucoside could enhance the absorption of Prim-O-glucosylcimifugin and cimifugin and improve the bioavailability, explaining preliminarily the rationality of Astragali Radix-Saposhnikoviae Radix herb couple.

Pharmacokinetic Interaction of astragaloside IV with atractylenolide I and prim-O-glucosylcimifugin in male Sprague Dawley rats.[Pubmed:24452462]

Planta Med. 2014 Feb;80(2-3):187-92.

Astragaloside IV, atractylenolide I, and Prim-O-glucosylcimifugin are main medicinal components of the traditional Chinese medicine prescription Yu-ping-feng which is composed of three herbs: Astragalus membranaceus, Atractylodes macrocephala, and Saposhnikovia divaricata. This study is aimed to assess the influence of atractylenolide I and Prim-O-glucosylcimifugin on the pharmacokinetic profile of astragaloside IV so as to investigate the pharmacokinetic mechanisms of the Yu-ping-feng prescription. Fifteen Sprague Dawley rats were randomized to three groups; astragaloside IV, astragaloside IV plus atractylenolide I, and a combination of astragaloside IV, atractylenolide I, and Prim-O-glucosylcimifugin were respectively administered to rats of these three groups via intragastric gavage. Serum samples were collected at different times after drug administration, and serum concentrations of astragaloside IV and atractylenolide I were simultaneously detected using HPLC-electrospray ionization-MS. Compared with administration of astragaloside IV alone, concentrations of astragaloside IV in the serum were significantly increased when it was given in combination with atractylenolide I or atractylenolide I+Prim-O-glucosylcimifugin, with higher values for Cmax (p = 0.019 and p = 0.033 compared with astragaloside IV + atractylenolide I and astragaloside IV + atractylenolide I + Prim-O-glucosylcimifugin groups, respectively) and AUC (p = 0.0052 and p = 0.0047 compared with astragaloside IV + atractylenolide I and astragaloside IV + atractylenolide I + Prim-O-glucosylcimifugin groups, respectively). Improvement in mean oral Cmax and mean systemic serum exposure because of the pharmacokinetic interaction between astragaloside IV and atractylenolide I might explain the rationale for the use of multiple herbs in Yu-ping-feng and of combinations of A.membranaceus and A. macrocephala.

Biotransformation of prim-O-glucosylcimifugin by human intestinal flora and its inhibition on NO production and DPPH free radical.[Pubmed:22917273]

J Asian Nat Prod Res. 2012;14(9):886-96.

Prim-O-glucosylcimifugin (PGCN), a highest content chromone in the roots of Saposhnikovia divaricata, was incubated with human intestinal flora (HIF), and two biotransformation products were obtained from the incubated solution by chromatographic methods. The chemical structures of the two biotransformation products were elucidated as cimifugin (CN) and 5-O-methylvisamminol (MVL), respectively, on the basis of NMR and MS data. The biotransformation product CN was formed through a deglucosylation of PGCN by beta-glucosidase secreted from the HIF, and then the hydroxymethyl group of CN was reduced to lead to occurrence of MVL. All of these compounds were evaluated for their effect on the inhibition of nitric oxide production induced by lipopolysaccharide in macrophage cell line RAW 264.7 and for 1,1-diphenyl-2-picrylhydrazyl free-radical scavenging activity in cell-free bioassay system.

Description

Prim-O-glucosylcimifugin exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by through regulating JAK2/STAT3 signaling.

Keywords:

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