Forsythoside A

CAS# 79916-77-1

Forsythoside A

Catalog No. BCN1195----Order now to get a substantial discount!

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Quality Control of Forsythoside A

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Chemical structure

Forsythoside A

3D structure

Chemical Properties of Forsythoside A

Cas No. 79916-77-1 SDF Download SDF
PubChem ID 5281773 Appearance White powder
Formula C29H36O15 M.Wt 624.59
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms Forsythiaside
Solubility DMSO : 125 mg/mL (200.13 mM; Need ultrasonic)
Chemical Name [(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC(=C(C=C3)O)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
Standard InChIKey DTOUWTJYUCZJQD-UJERWXFOSA-N
Standard InChI InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29+/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 Forsythoside A

1 Rehmannia sp.

Biological Activity of Forsythoside A

DescriptionForsythoside A possesses strong antibacterial, antiinflammatory, antioxidant and antiviral effects. it has the potential to prevent IBV infection in vitro, it can promote the expression of IFN-α and Mx1 significantly.Forsythoside A has inductive effects on the activities of CYP1A2 and CYP2C11, without affecting CYP2D1 and CYP3A1/2 activities.
TargetsAntifection | P450 (e.g. CYP17) | P-gp
In vitro

Forsythoside a inhibits the avian infectious bronchitis virus in cell culture.[Pubmed: 20677175]

Phytother Res. 2011 Mar;25(3):338-42.

Forsythoside A is a polyphenolic constituent of the fruits of Forsythia suspensa Vahl. which is widely used as an antiinflammatory agent in traditional Chinese medicine.
METHODS AND RESULTS:
In the present study, the effects of Forsythoside A on cell infection by avian infectious bronchitis virus were assessed. A real-time fluorescence quantitative PCR assay was used to determine mRNA content of IBV N gene. The pretreatment of cells with Forsythoside A, adding Forsythoside A post infection of cells, and treatment of virus with Forsythoside A were analysed. The inhibitory effect of Forsythoside A was confirmed by infecting primary chicken embryo kidney cells. Infected cells were inhibited by Forsythoside A treatment.
CONCLUSIONS:
The data indicated that Forsythoside A has the potential to prevent IBV infection in vitro.

Protocol of Forsythoside A

Kinase Assay

Effects of phillyrin and forsythoside A on rat cytochrome P450 activities in vivo and in vitro.[Pubmed: 27310729 ]

Xenobiotica. 2017 Apr;47(4):297-303.

1. Phillyrin and Forsythoside A are two important active ingredients in Forsythia suspensa. However, the effects of phillyrin and Forsythoside A on the activities of cytochrome P450 (CYP450) remain unclear.
METHODS AND RESULTS:
2. This study aimed to investigate the effects of phillyrin and Forsythoside A on the activities of CYP1A2, CYP2C11, CYP2D1 and CYP3A1/2 by cocktail probe drugs in rats both in vivo and in vitro. 3. Many pharmacokinetic parameters of caffeine and metoprolol in phillyrin pretreatment group, caffeine and tolbutamide in Forsythoside A pretreatment group were affected significantly. In rat liver microsomal incubation system, the concentrations of acetaminophen and dextrophan in the phillyrin pretreatment group are higher than blank control group by 207.69% and 125.00%, however, the concentrations of 4-hydroxytolbutamide and 6β-hydroxytestosterone were not significantly altered. The concentrations of acetaminophen and 4-hydroxytolbutamide in the Forsythoside A pretreatment group are higher than blank control group by 223.07% and 154.16%, whereas the concentrations of dextrophan and 6β-hydroxytestosterone were not significantly altered.
CONCLUSIONS:
4. These results indicated that Phillyrin had potential inductive effects on rat CYP1A2 and CYP2D1 activities, without affecting CYP2C11 and CYP3A1/2 activities. Moreover, Forsythoside A had inductive effects on the activities of CYP1A2 and CYP2C11, without affecting CYP2D1 and CYP3A1/2 activities.

Cell Research

Improvement of intestinal absorption of forsythoside A in weeping forsythia extract by various absorption enhancers based on tight junctions.[Pubmed: 23089157]

Phytomedicine. 2012 Dec 15;20(1):47-58.

Forsythoside A (FTA), one of the main active ingredients in weeping forsythia extract, possesses strong antibacterial, antioxidant and antiviral effects, and its content was about 8% of totally, higher largely than that of other ingredients, but the absolute bioavailability orally was approximately 0.5%, which is significant low influencing clinical efficacies of its oral preparations. In the present study, in vitro Caco-2 cell, in situ single-pass intestinal perfusion and in vivo pharmacokinetics study were performed to investigate the effects of absorption enhancers based on tight junctions: sodium caprate and water-soluble chitosan on the intestinal absorption of FTA, and the eventual mucosal epithelial damage resulted from absorption enhancers was evaluated by MTT test, measurement of total amount of protein and the activity of LDH and morphology observation, respectively. The pharmacological effects such as antioxidant activity improvement by absorption enhancers were verified by PC12 cell damage inhibition rate after H₂O₂ insults. The observations from in vitro Caco-2 cell showed that the absorption of FTA in weeping forsythia extract could be improved by absorption enhancers. Meanwhile, the absorption enhancing effect of water-soluble chitosan may be almost saturable up to 0.0032% (w/v), and sodium caprate at concentrations up to 0.64 mg/ml was safe for the Caco-2 cells, but water-soluble chitosan at different concentrations was all safe for these cells.

Forsythoside A Dilution Calculator

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Forsythoside A Molarity Calculator

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Preparing Stock Solutions of Forsythoside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6011 mL 8.0053 mL 16.0105 mL 32.021 mL 40.0263 mL
5 mM 0.3202 mL 1.6011 mL 3.2021 mL 6.4042 mL 8.0053 mL
10 mM 0.1601 mL 0.8005 mL 1.6011 mL 3.2021 mL 4.0026 mL
50 mM 0.032 mL 0.1601 mL 0.3202 mL 0.6404 mL 0.8005 mL
100 mM 0.016 mL 0.0801 mL 0.1601 mL 0.3202 mL 0.4003 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 Forsythoside A

In vitro metabolism in Sprague-Dawley rat liver microsomes of forsythoside A in different compositions of Shuang-Huang-Lian.[Pubmed:21888954]

Fitoterapia. 2011 Dec;82(8):1222-30.

Shuang-Huang-Lian (SHL), a traditional Chinese formula containing Lonicerae japonicae flos (LJF), Scutellariae radix (SR) and Forsythiae fructus (FF), is commonly used to treat acute upper respiratory tract infection, acute bronchitis and light pneumonia. Forsythoside A is one of the main active ingredients in Forsythiae fructus, a key herb in SHL. In the present study, effects of different compositions in SHL on the in vitro metabolism in Sprague-Dawley rat liver microsomes of Forsythoside A were investigated. The observations from Sprague-Dawley rat liver microsomes in the presence of beta-NADPH or UDPGA that Forsythoside A may be the substrates of CYP3A4, CYP2C9, CYP1A2, UGT1A6, UGT1A3, UGT1A1 and UGT1A9; Chlorogenic acid may be the substrates of CYP3A4, CYP2C9, CYP1A2, CYP2C19, UGT1A6, UGT1A3 and UGT1A1; Baicalin may be the substrates of CYP3A4, CYP2C19, CYP1A2, UGT1A9, UGT1A1 and UGT1A3; Baicalein may be the substrates of CYP3A4, CYP2E1 and UGT1A6. It was also found that the residue of Forsythoside A in SHL, FF+LJF and FF+SR was greatly increased compared with that in FF in Sprague-Dawley rat liver microsomes in the presence of beta-NADPH or UDPGA, which indicated that the metabolism of Forsythoside A in SHL may be influenced by chlorogenic acid in LJF acting on the CYP3A4, CYP2C9, CYP1A2, UGT1A6, UGT1A3 and UGT1A1; baicalin in SR acting on the CYP3A4, CYP1A2, UGT1A9, UGT1A1 and UGT1A3; baicalein acting on the CYP3A4 and UGT1A6 respectively.

Improvement of intestinal absorption of forsythoside A in weeping forsythia extract by various absorption enhancers based on tight junctions.[Pubmed:23089157]

Phytomedicine. 2012 Dec 15;20(1):47-58.

Forsythoside A (FTA), one of the main active ingredients in weeping forsythia extract, possesses strong antibacterial, antioxidant and antiviral effects, and its content was about 8% of totally, higher largely than that of other ingredients, but the absolute bioavailability orally was approximately 0.5%, which is significant low influencing clinical efficacies of its oral preparations. In the present study, in vitro Caco-2 cell, in situ single-pass intestinal perfusion and in vivo pharmacokinetics study were performed to investigate the effects of absorption enhancers based on tight junctions: sodium caprate and water-soluble chitosan on the intestinal absorption of FTA, and the eventual mucosal epithelial damage resulted from absorption enhancers was evaluated by MTT test, measurement of total amount of protein and the activity of LDH and morphology observation, respectively. The pharmacological effects such as antioxidant activity improvement by absorption enhancers were verified by PC12 cell damage inhibition rate after H(2)O(2) insults. The observations from in vitro Caco-2 cell showed that the absorption of FTA in weeping forsythia extract could be improved by absorption enhancers. Meanwhile, the absorption enhancing effect of water-soluble chitosan may be almost saturable up to 0.0032% (w/v), and sodium caprate at concentrations up to 0.64 mg/ml was safe for the Caco-2 cells, but water-soluble chitosan at different concentrations was all safe for these cells. The observations from single-pass intestinal perfusion in situ model showed that duodenum, jejunum, ileum and colon showed significantly concentration-dependent increase in P(eff)-value, and that P(eff)-value in the ileum and colon groups, where sodium caprate was added, was higher than that of duodenum and jejunum groups, but P(eff)-value in the jejunum group was higher than that of duodenum, ileum and colon groups where water-soluble chitosan was added. Intestinal mucosal toxicity studies showed no significant toxicity below 800 mug/ml sodium caprate and water-soluble chitosan at different concentrations. In pharmacokinetics study, water-soluble chitosan at dosage of 50mg/kg improved the bioavailability of FTA in weeping forsythia extract to the greatest extent, and was safe for gastrointestine from morphological observation. Besides, treatment with weeping forsythia extract with water-soluble chitosan at dosage of 50 mg/kg prevented PC12 cell damage upon H(2)O(2) stimulation better than that of control. All findings above suggested that water-soluble chitosan at dosage of 50 mg/kg might be safe and effective absorption enhancer for improving the bioavailability of FTA and the antioxidant activity in vivo in weeping forsythia extract.

Forsythoside a inhibits the avian infectious bronchitis virus in cell culture.[Pubmed:20677175]

Phytother Res. 2011 Mar;25(3):338-42.

Forsythoside A is a polyphenolic constituent of the fruits of Forsythia suspensa Vahl. which is widely used as an antiinflammatory agent in traditional Chinese medicine. In the present study, the effects of Forsythoside A on cell infection by avian infectious bronchitis virus were assessed. A real-time fluorescence quantitative PCR assay was used to determine mRNA content of IBV N gene. The pretreatment of cells with Forsythoside A, adding Forsythoside A post infection of cells, and treatment of virus with Forsythoside A were analysed. The inhibitory effect of Forsythoside A was confirmed by infecting primary chicken embryo kidney cells. Infected cells were inhibited by Forsythoside A treatment. The data indicated that Forsythoside A has the potential to prevent IBV infection in vitro. Copyright (c) 2010 John Wiley & Sons, Ltd.

Effects of phillyrin and forsythoside A on rat cytochrome P450 activities in vivo and in vitro.[Pubmed:27310729]

Xenobiotica. 2017 Apr;47(4):297-303.

1. Phillyrin and Forsythoside A are two important active ingredients in Forsythia suspensa. However, the effects of phillyrin and Forsythoside A on the activities of cytochrome P450 (CYP450) remain unclear. 2. This study aimed to investigate the effects of phillyrin and Forsythoside A on the activities of CYP1A2, CYP2C11, CYP2D1 and CYP3A1/2 by cocktail probe drugs in rats both in vivo and in vitro. 3. Many pharmacokinetic parameters of caffeine and metoprolol in phillyrin pretreatment group, caffeine and tolbutamide in Forsythoside A pretreatment group were affected significantly. In rat liver microsomal incubation system, the concentrations of acetaminophen and dextrophan in the phillyrin pretreatment group are higher than blank control group by 207.69% and 125.00%, however, the concentrations of 4-hydroxytolbutamide and 6beta-hydroxytestosterone were not significantly altered. The concentrations of acetaminophen and 4-hydroxytolbutamide in the Forsythoside A pretreatment group are higher than blank control group by 223.07% and 154.16%, whereas the concentrations of dextrophan and 6beta-hydroxytestosterone were not significantly altered. 4. These results indicated that Phillyrin had potential inductive effects on rat CYP1A2 and CYP2D1 activities, without affecting CYP2C11 and CYP3A1/2 activities. Moreover, Forsythoside A had inductive effects on the activities of CYP1A2 and CYP2C11, without affecting CYP2D1 and CYP3A1/2 activities.

[Intestinal absorption of forsythoside A by rat circulation in situ].[Pubmed:21361037]

Yao Xue Xue Bao. 2010 Nov;45(11):1373-8.

This study is to investigate the effects of concentration, intestinal section, pH, paracellular route, substrate/inhibitor of enzyme (CYP3A) and proteins (P-gp, MRP2, SGL1) on the absorption of Forsythoside A. The absorption of three concentrations (2.6, 5.2, and 10.4 microg x mL(-1)) of Forsythoside A in different intestinal segments was studied with phenol red as the marker by rat circulation in situ. The results showed that the residue of Forsythoside A with different concentrations had little significant difference from that obtained after perfusing via duodenum, jejunum, ileum and colon, which indicated that the absorption of Forsythoside A was passive diffusion and had no difference in different segments of rat intestine. The residue of Forsythoside A increased to 466.160 and 463.429 microg respectively when cyclosporine (4 microg x mL(-1)) or midazolam (50 micromol x L(-1)) was added to the circulation fluid, which showed significant difference compared to the control group (P < 0.05). Moreover, the residue of Forsythoside A showed a tendency of increase with the increase of cyclosporine or midazolam. When digoxin (50 micromol x L(-1)) or EDTA (10 microg x mL(-1)) was added to the circulation fluid, the residue of Forsythoside A decreased to 325.110 and 369.888 microg respectively, which showed significant difference as compared to the control group (P < 0.05). Besides, the residue of Forsythoside A showed a tendency of reduction with the increase of digoxin or EDTA. However, there is no significant change in the absorption of Forsythoside A when the different concentrations of mannitol were added to the circulation fluid. The results above indicated that the absorption of Forsythoside A was mainly passive diffusion and involved paracellular route at the same time. In addition, the substrates of P-gp or CYP3A had dose-dependent effect on the absorption of Forsythoside A.

Description

Forsythiaside A, a phenylethanoside product isolated from air-dried fruits of Forsythia suspense, has anti-inflammatory and antioxidant effects.

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