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Pectolinarigenin

CAS# 520-12-7

Pectolinarigenin

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Chemical structure

Pectolinarigenin

3D structure

Chemical Properties of Pectolinarigenin

Cas No. 520-12-7 SDF Download SDF
PubChem ID 5320438 Appearance Yellow powder
Formula C17H14O6 M.Wt 314.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 5,7-Dihydroxy 4',6-dimethoxyflavone; 4',6-Dimethoxyscutellarein; Hortensin; 6-Methoxyacacetin; 6-Methoxyapigenin 4'-methyl ether; 6-Methoxykaempferide; 6-Methoxy 4'-methylapigenin; 4'-Methylcapillarisin; Pectolarigenin; Scutellarein 4',6-dimethyl ether
Solubility Sparingly soluble in ethanol and methan
Chemical Name 5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)O)OC)O
Standard InChIKey GPQLHGCIAUEJQK-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)13-7-11(18)15-14(23-13)8-12(19)17(22-2)16(15)20/h3-8,19-20H,1-2H3
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 Pectolinarigenin

1 Eupatorium sp. 2 Linaria sp. 3 Trifolium sp.

Biological Activity of Pectolinarigenin

DescriptionPectolinarigenin possesses anti-inflammatory, antiallergic and hepatoprotective activities.It is a dual inhibitor of COX-2/5-LOX,and the IC50 >1 microM; it also can increase activity levels of GSH, GR, GCS, and GST, as well as SOD.
TargetsCOX | LOX | SOD
In vitro

Anti-inflammatory activity of pectolinarigenin and pectolinarin isolated from Cirsium chanroenicum.[Pubmed: 18981574]

Biol Pharm Bull. 2008 Nov;31(11):2063-7.


CONCLUSIONS:
In order to identify the active anti-inflammatory ingredient(s) in Cirsium chanroenicum (Compositae), its methanol extract and several solvent fractions were prepared; the methanol extract and the ethylacetate fraction inhibited cyclooxygenase-2 (COX-2)-mediated prostaglandin E2 (PGE2) and 5-lipoxygenase (5-LOX)-mediated leukotriene (LT) production in lipopolysaccharide-treated RAW 264.7 cells and A23187-treated rat basophilic leukemia (RBL-1) cells, respectively. Further bioactivity-guided fractionation of the ethylacetate fraction using column chromatography led to the isolation of Pectolinarigenin (5,7-dihydroxy-4',6-dimethoxyflavone), along with pectolinarin [Pectolinarigenin 7-rhamnosyl-(1-->6)-glucoside]. Pectolinarigenin strongly inhibited COX-2-mediated PGE2 and 5-LOX-mediated LT production at >1 microM, indicating that it is a dual inhibitor of COX-2/5-LOX. However, Pectolinarigenin did not affect COX-2 expression or nuclear transcription factor (NF-kappaB) activation. In addition, in vivo studies demonstrated that oral administration of these two compounds at 20-100 mg/kg resulted in similar inhibitory activities against several animal models of inflammation/allergy: arachidonic acid-induced mouse ear edema, carrageenan-induced mouse paw edema and passive cutaneous anaphylaxis.
CONCLUSIONS:
All of these results suggest that Pectolinarigenin and pectolinarin possess anti-inflammatory activity and that they may inhibit eicosanoid formation in inflammatory lesions. These activities certainly contribute to the anti-inflammatory mechanism of C. chanroenicum.

In vivo

Inhibitory Effect on β -Hexosaminidase Release from RBL-2H3 Cells of Extracts and Some Pure Constituents of Benchalokawichian, a Thai Herbal Remedy, Used for Allergic Disorders.[Pubmed: 25580152]

Evid Based Complement Alternat Med. 2014;2014:828760.

Benchalokawichian (BCW), a Thai traditional herbal formulation, has long been used as antipyretic and to treat skin disorders. It comprises roots from five herbs: Ficus racemosa, Capparis micracantha, Clerodendrum petasites, Harrisonia perforata, and Tiliacora triandra. This polyherbal remedy has recently been included in the Thailand National List of Essential Medicines (Herbal Products list).
METHODS AND RESULTS:
A Bioassay-guided fractionation technique was used to evaluate antiallergy activities of crude extracts, and those obtained by the multistep column chromatography isolation of pure compounds. Inhibitory effect on the release of β-hexosaminidase from RBL-2H3 cells was used to determine antiallergic activity. Two pure compounds from BCW formulation showed higher antiallergic activity than crude or semipure extracts. Pectolinarigenin showed the highest antiallergic activity, followed by O-methylalloptaeroxylin, with IC50 values of 6.3 μg/mL and 14.16 μg/mL, respectively. Moreover, the highest activities of pure compounds were significantly higher than chlorpheniramine (16.2 μg/mL).
CONCLUSIONS:
This study provides some support for the use of BCW in reducing itching and treatment of other skin allergic disorders. The two isolated constituents exhibited high antiallergic activity and it is necessary to determine their mechanism of action. Further phytochemical and safety studies of pure compounds are required before development of these as antiallergy commercial remedies.

Protocol of Pectolinarigenin

Animal Research

Pectolinarin and Pectolinarigenin of Cirsium setidens Prevent the Hepatic Injury in Rats Caused by D-Galactosamine via an Antioxidant Mechanism.[Pubmed: 18379079]

Biol Pharm Bull. 2008 Apr;31(4):760-4.

To identify the hepatoprotective component from the leaves of Cirsium setidens (Compositae), the methanolic extract was divided into two fractions, chloroform and butanol fractions, and their hepatoprotective efficacy was evaluated in a rat model of hepatic injury caused by D-galactosamine (GalN).
METHODS AND RESULTS:
Hepatoprotective activity was measured by the activity of serum aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase (ALP), and lactate dehydrogenase (LDH). Glutathione metabolism was measured via biochemical parameters such as glutathione (GSH), glutathione reductase (GR), gamma-glutamylcysteine synthetase (GCS), glutathione S-transferase (GST), and superoxide dismutase (SOD) levels. We subjected the butanol fraction, which had higher activity, to column chromatography to yield pectolinarin, which was further hydrolyzed to yield Pectolinarigenin. Administration (10, 20 mg/kg, p.o.) of the main flavonoid glycoside component, pectolinarin, and its aglycone, Pectolinarigenin, for 2 weeks significantly decreased the activity levels of AST, ALT, ALP and LDH, indicating that the two compounds have hepatoprotective activity. Pectolinarin and Pectolinarigenin also increased activity levels of GSH, GR, GCS, and GST, as well as SOD. The significant effect was only seen in SOD activity.
CONCLUSIONS:
This suggests that the two components exhibit hepatoprotective activity mainly via SOD antioxidant mechanism.

Pectolinarigenin Dilution Calculator

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Preparing Stock Solutions of Pectolinarigenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1817 mL 15.9084 mL 31.8167 mL 63.6335 mL 79.5418 mL
5 mM 0.6363 mL 3.1817 mL 6.3633 mL 12.7267 mL 15.9084 mL
10 mM 0.3182 mL 1.5908 mL 3.1817 mL 6.3633 mL 7.9542 mL
50 mM 0.0636 mL 0.3182 mL 0.6363 mL 1.2727 mL 1.5908 mL
100 mM 0.0318 mL 0.1591 mL 0.3182 mL 0.6363 mL 0.7954 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 Pectolinarigenin

Inhibitory Effect on beta -Hexosaminidase Release from RBL-2H3 Cells of Extracts and Some Pure Constituents of Benchalokawichian, a Thai Herbal Remedy, Used for Allergic Disorders.[Pubmed:25580152]

Evid Based Complement Alternat Med. 2014;2014:828760.

Introduction. Benchalokawichian (BCW), a Thai traditional herbal formulation, has long been used as antipyretic and to treat skin disorders. It comprises roots from five herbs: Ficus racemosa, Capparis micracantha, Clerodendrum petasites, Harrisonia perforata, and Tiliacora triandra. This polyherbal remedy has recently been included in the Thailand National List of Essential Medicines (Herbal Products list). Methodology. A Bioassay-guided fractionation technique was used to evaluate antiallergy activities of crude extracts, and those obtained by the multistep column chromatography isolation of pure compounds. Inhibitory effect on the release of beta-hexosaminidase from RBL-2H3 cells was used to determine antiallergic activity. Results. Two pure compounds from BCW formulation showed higher antiallergic activity than crude or semipure extracts. Pectolinarigenin showed the highest antiallergic activity, followed by O-methylalloptaeroxylin, with IC50 values of 6.3 mug/mL and 14.16 mug/mL, respectively. Moreover, the highest activities of pure compounds were significantly higher than chlorpheniramine (16.2 mug/mL). Conclusions. This study provides some support for the use of BCW in reducing itching and treatment of other skin allergic disorders. The two isolated constituents exhibited high antiallergic activity and it is necessary to determine their mechanism of action. Further phytochemical and safety studies of pure compounds are required before development of these as antiallergy commercial remedies.

Pectolinarin and Pectolinarigenin of Cirsium setidens Prevent the Hepatic Injury in Rats Caused by D-Galactosamine via an Antioxidant Mechanism.[Pubmed:18379079]

Biol Pharm Bull. 2008 Apr;31(4):760-4.

To identify the hepatoprotective component from the leaves of Cirsium setidens (Compositae), the methanolic extract was divided into two fractions, chloroform and butanol fractions, and their hepatoprotective efficacy was evaluated in a rat model of hepatic injury caused by D-galactosamine (GalN). Hepatoprotective activity was measured by the activity of serum aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase (ALP), and lactate dehydrogenase (LDH). Glutathione metabolism was measured via biochemical parameters such as glutathione (GSH), glutathione reductase (GR), gamma-glutamylcysteine synthetase (GCS), glutathione S-transferase (GST), and superoxide dismutase (SOD) levels. We subjected the butanol fraction, which had higher activity, to column chromatography to yield pectolinarin, which was further hydrolyzed to yield Pectolinarigenin. Administration (10, 20 mg/kg, p.o.) of the main flavonoid glycoside component, pectolinarin, and its aglycone, Pectolinarigenin, for 2 weeks significantly decreased the activity levels of AST, ALT, ALP and LDH, indicating that the two compounds have hepatoprotective activity. Pectolinarin and Pectolinarigenin also increased activity levels of GSH, GR, GCS, and GST, as well as SOD. The significant effect was only seen in SOD activity. This suggests that the two components exhibit hepatoprotective activity mainly via SOD antioxidant mechanism.

Anti-inflammatory activity of pectolinarigenin and pectolinarin isolated from Cirsium chanroenicum.[Pubmed:18981574]

Biol Pharm Bull. 2008 Nov;31(11):2063-7.

In order to identify the active anti-inflammatory ingredient(s) in Cirsium chanroenicum (Compositae), its methanol extract and several solvent fractions were prepared; the methanol extract and the ethylacetate fraction inhibited cyclooxygenase-2 (COX-2)-mediated prostaglandin E2 (PGE2) and 5-lipoxygenase (5-LOX)-mediated leukotriene (LT) production in lipopolysaccharide-treated RAW 264.7 cells and A23187-treated rat basophilic leukemia (RBL-1) cells, respectively. Further bioactivity-guided fractionation of the ethylacetate fraction using column chromatography led to the isolation of Pectolinarigenin (5,7-dihydroxy-4',6-dimethoxyflavone), along with pectolinarin [Pectolinarigenin 7-rhamnosyl-(1-->6)-glucoside]. Pectolinarigenin strongly inhibited COX-2-mediated PGE2 and 5-LOX-mediated LT production at >1 microM, indicating that it is a dual inhibitor of COX-2/5-LOX. However, Pectolinarigenin did not affect COX-2 expression or nuclear transcription factor (NF-kappaB) activation. In addition, in vivo studies demonstrated that oral administration of these two compounds at 20-100 mg/kg resulted in similar inhibitory activities against several animal models of inflammation/allergy: arachidonic acid-induced mouse ear edema, carrageenan-induced mouse paw edema and passive cutaneous anaphylaxis. All of these results suggest that Pectolinarigenin and pectolinarin possess anti-inflammatory activity and that they may inhibit eicosanoid formation in inflammatory lesions. These activities certainly contribute to the anti-inflammatory mechanism of C. chanroenicum.

Description

Pectolinarigenin, isolated from Cirsium chanroenicum, is a dual inhibitor of COX-2/5-LOX. Anti-inflammatory activity. Pectolinarigenin has potent inhibitory activities on melanogenesis.

Keywords:

Pectolinarigenin,520-12-7,5,7-Dihydroxy 4',6-dimethoxyflavone; 4',6-Dimethoxyscutellarein; Hortensin; 6-Methoxyacacetin; 6-Methoxyapigenin 4'-methyl ether; 6-Methoxykaempferide; 6-Methoxy 4'-methylapigenin; 4'-Methylcapillarisin; Pectolarigenin; Scutellarein 4',6-dimethyl ether,Natural Products, buy Pectolinarigenin , Pectolinarigenin supplier , purchase Pectolinarigenin , Pectolinarigenin cost , Pectolinarigenin manufacturer , order Pectolinarigenin , high purity Pectolinarigenin

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