Salvigenin

CAS# 19103-54-9

Salvigenin

2D Structure

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Salvigenin

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Chemical Properties of Salvigenin

Cas No. 19103-54-9 SDF Download SDF
PubChem ID 161271 Appearance Yellow powder
Formula C18H16O6 M.Wt 328.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O
Standard InChIKey QCDYOIZVELGOLZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)13-8-12(19)16-14(24-13)9-15(22-2)18(23-3)17(16)20/h4-9,20H,1-3H3
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 Salvigenin

The roots of Salvia japonica

Biological Activity of Salvigenin

DescriptionSalvigenin, a potent hMAO-A [monoamine oxidases (MAOs)]inhibitor, has neuroprotective, antitumor and immunomodulatory effects, it has potential to ameliorate Streptozotocin-induced diabetes mellitus and heart complications in rats. Salvigenin has dose-dependent analgesic effect so that it can be useful in controlling of inflammations, acute and chronic pain.
Targetsgp120/CD4 | IL Receptor | Caspase | Bcl-2/Bax | MAO | Immunology & Inflammation related
In vitro

Increase of autophagy and attenuation of apoptosis by Salvigenin promote survival of SH-SY5Y cells following treatment with H₂O₂.[Pubmed: 22899171]

Mol Cell Biochem. 2012 Dec;371(1-2):9-22.

Oxidative stress is a major component of harmful cascades activated in neurodegenerative disorders.
METHODS AND RESULTS:
Here, we tried to elucidate the possible neuroprotective effect of Salvigenin, a natural polyphenolic compound, on oxidative stress-induced apoptosis and autophagy in human neuroblastoma SH-SY5Y cells. We measured cell viability by MTT test and found that 25 μM is the best protective concentration of Salvigenin. GSH and SOD assays suggested that Salvigenin activates antioxidant factors. At the same time, measurement of ER stress-associated proteins including calpain and caspase-12 showed the ability of Salvigenin to decrease ER stress. We found that Salvigenin could decrease the apoptotic factors. Salvigenin inhibited H(2)O(2)-induced caspase-3 which is a hallmark of apoptosis in addition to reducing Bax\Bcl-2 ratio by 1.45 fold. Additionally, Salvigenin increased the levels of autophagic factors.
CONCLUSIONS:
Our results showed an increase in LC3-II/LC3-I ratio, Atg7, and Atg12 in the presence of 25 μM of Salvigenin by about 1.28, 1.25, and 1.54 folds, respectively, compared to H(2)O(2)-treated cells. So it seems that H(2)O(2) cytotoxicity mainly results from apoptosis. Besides, Salvigenin helps cells to survive by inhibiting apoptosis and enhancing autophagy that opens a new horizon for the future experiments.

In vivo

Antitumor and immunomodulatory effects of salvigenin on tumor bearing mice.[Pubmed: 24270218]

Cell Immunol. 2013 Nov-Dec;286(1-2):16-21.

Development of agents that specifically kill cancer cells and simultaneously elicit antitumor immune response is a step forward in cancer therapy. Immunostimulation can result in eliminating of the cancer cells; immunotherapy is a promising approach in balancing the immune response by Treg.
METHODS AND RESULTS:
In the present study, we investigated whether the administration of Salvigenin contributes to the augmentation of antitumor immunity and the regression of tumor tissues in a mouse model of breast cancer. Salvigenin was purified from Tanacetum canescens, and its effect on the tumor volume was investigated. The splenocyte proliferation, shifting of cytokine profile, and the presence of naturally-occurring CD4+CD25+Foxp3+ Treg cells were assessed to describe the anti-tumor immune response.
CONCLUSIONS:
Our results demonstrated that a significant decrease in the level of IL-4 and increase in the IFN-γ in the animals treated with Salvigenin and significant decreased in the level of splenic CD4+CD25+Foxp3+ T regulatory cells. The cytotoxic and immunomodulatory properties of Salvigenin were acknowledged in vivo.

Anti-inflammatory and Analgesic Properties of Salvigenin, Salvia officinalis Flavonoid Extracted.[Reference: WebLink]

Advaced Herbal Medicine , 2015, 1(3):31-41.

Salvigenin is one of the active flavonoids existing in this plant. The aim of this study was to evaluate the anti-inflammatory and analgesic effect of Salvigenin, Salvia officinalis flavonoid extracted.
METHODS AND RESULTS:
In this laboratory experimental study, plant was extracted and the column chromatography was used to purify prepared extracts. 100 male albino mice and 48 male wistar rats were selected. In the hot plate test and in the writhing test, animals were divided randomly into 5 groups. Group 1 (received 10 mg/kg normal saline), groups 2, 3 and 4 (received Salvigenin 25, 50 and 100 mg/kg intraperitoneally, espectively), group 5 (received 10 mg/kg morphine in hot plate test and 10 mg/kg indomethacin in writhing test). In the inflammatory test, animals were divided into 6 groups. Group 1 was assigned as a control group which received 0.05 ml of carrageenin. Groups 2, 3 and 4 (received Salvigenin, at doses of 25, 50 and 100 mg/kg). Group 5 (received 10 mg/kg indomethacin) and then changes of the volume of all groups were measured. Data were analyzed using ANOVA and Tukey test and P. In writhing test, Salvigenin reduced the number of abdominal contractions at doses of 50 and 100 mg/kg. Increasing dose of Salvigenin, with reduction in abdominal cramps resulted in the increasing of pain inhibition, and the percentage of this inhibition was statistically significant (P<0.001). In hot plate test, also 30, 45 and 60 minutes after injection of Salvigenin and morphine showed significant difference compared to the control group (P<0.001). Also, Salvigenin increased the maximum percentage of analgesic compared to the control group (P<0.001). Salvigenin could reduce inflammation and in the group that received Salvigenin at 100 mg/kg, the inflammation was significantly lower than the control group (P<0.05).
CONCLUSIONS:
Our findings showed that Salvigenin has dose-dependent analgesic effect so that it can be useful in controlling of inflammations, acute and chronic pain.

Protocol of Salvigenin

Kinase Assay

Flavonoids from Sideritis Species: Human Monoamine Oxidase (hMAO) Inhibitory Activities, Molecular Docking Studies and Crystal Structure of Xanthomicrol.[Pubmed: 25915461]

Molecules. 2015 Apr 23;20(5):7454-73.

The inhibitory effects of flavonoids on monoamine oxidases (MAOs) have attracted great interest since alterations in monoaminergic transmission are reported to be related to neurodegenerative diseases such as Parkinson's and Alzheimer's diseases and psychiatric disorders such as depression and anxiety, thus MAOs may be considered as targets for the treatment of these multi-factorial diseases.
METHODS AND RESULTS:
In the present study, four Sideritis flavonoids, xanthomicrol (1), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (2), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (3) and Salvigenin (4) were docked computationally into the active site of the human monoamine oxidase isoforms (hMAO-A and hMAO-B) and were also investigated for their hMAO inhibitory potencies using recombinant hMAO isoenzymes. The flavonoids inhibited hMAO-A selectively and reversibly in a competitive mode. Salvigenin (4) was found to be the most potent hMAO-A inhibitor, while xanthomicrol (1) appeared as the most selective hMAO-A inhibitor. The computationally obtained results were in good agreement with the corresponding experimental values. In addition, the x-ray structure of xanthomicrol (1) has been shown.
CONCLUSIONS:
The current work warrants further preclinical studies to assess the potential of xanthomicrol (1) and Salvigenin (4) as new selective and reversible hMAO-A inhibitors for the treatment of depression and anxiety.

Animal Research

Salvigenin has Potential to Ameliorate Streptozotocin-induced Diabetes Mellitus and Heart Complications in Rats.[Reference: WebLink]

British Journal of Medicine Medical Research., 2016, 15(2):1-12.

Flavonoids are the active ingredients, found in herbal remedies for amelioration the variety of disorders. Salvigenin is a plant flavenoid, which is found in Salvia officinalis. Salvigenin has an antioxidant, anti-inflamatory, anti-tumor and vascular relaxant activities. This study was conducted to evaluate the possible antidiabetic and cardioprotective effects of Salvigenin.
METHODS AND RESULTS:
32 wistar rats were made diabetic using streptozotocin (60 mg/kg, i.p.). Rats were divided into four groups that treated with Salvigenin at doses of 5, 10 or 25 mg/kg. All the treatments were administered orally for 4 weeks. At the end of the experiment, the blood samples were collected for determining the FBS, HbA1C, insulin, triglyceride, cholesterol and HDL. After 72 hrs, animals were anesthetized; hearts were removed quickly and mounted on Langendorff apparatus. The max pressure, heart rate, max dP/dt, contractility index and coronary flow were measured. Administration of Salvigenin exhibited a significant reduction in fasting serum glucose, triglycerides, total cholesterol, HbA1c and increased level of plasma insulin and HDL in diabetic rats (P<0/05). Salvigenin could significantly increased hemodynamic indices such as max pressure, max dP/dt, contractility and coronary flow (P<0/05).
CONCLUSIONS:
Salvigenin improved diabetes through decreasing blood glucose, lipid profile, HbA1c. Increased insulin secretion can be a mechanism for antidiabetic effect of Salvigenin. Regarding the antidiabetic and cardioprotective effects of Salvigenin, it can be concluded that this flavonoid compound can be potentially used to reduce diabetes and it’s cardiovascular complications.

Salvigenin Dilution Calculator

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Preparing Stock Solutions of Salvigenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.046 mL 15.23 mL 30.4599 mL 60.9199 mL 76.1499 mL
5 mM 0.6092 mL 3.046 mL 6.092 mL 12.184 mL 15.23 mL
10 mM 0.3046 mL 1.523 mL 3.046 mL 6.092 mL 7.615 mL
50 mM 0.0609 mL 0.3046 mL 0.6092 mL 1.2184 mL 1.523 mL
100 mM 0.0305 mL 0.1523 mL 0.3046 mL 0.6092 mL 0.7615 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 Salvigenin

Increase of autophagy and attenuation of apoptosis by Salvigenin promote survival of SH-SY5Y cells following treatment with H(2)O(2).[Pubmed:22899171]

Mol Cell Biochem. 2012 Dec;371(1-2):9-22.

Oxidative stress is a major component of harmful cascades activated in neurodegenerative disorders. Here, we tried to elucidate the possible neuroprotective effect of Salvigenin, a natural polyphenolic compound, on oxidative stress-induced apoptosis and autophagy in human neuroblastoma SH-SY5Y cells. We measured cell viability by MTT test and found that 25 muM is the best protective concentration of Salvigenin. GSH and SOD assays suggested that Salvigenin activates antioxidant factors. At the same time, measurement of ER stress-associated proteins including calpain and caspase-12 showed the ability of Salvigenin to decrease ER stress. We found that Salvigenin could decrease the apoptotic factors. Salvigenin inhibited H(2)O(2)-induced caspase-3 which is a hallmark of apoptosis in addition to reducing Bax\Bcl-2 ratio by 1.45 fold. Additionally, Salvigenin increased the levels of autophagic factors. Our results showed an increase in LC3-II/LC3-I ratio, Atg7, and Atg12 in the presence of 25 muM of Salvigenin by about 1.28, 1.25, and 1.54 folds, respectively, compared to H(2)O(2)-treated cells. So it seems that H(2)O(2) cytotoxicity mainly results from apoptosis. Besides, Salvigenin helps cells to survive by inhibiting apoptosis and enhancing autophagy that opens a new horizon for the future experiments.

Flavonoids from Sideritis Species: Human Monoamine Oxidase (hMAO) Inhibitory Activities, Molecular Docking Studies and Crystal Structure of Xanthomicrol.[Pubmed:25915461]

Molecules. 2015 Apr 23;20(5):7454-73.

The inhibitory effects of flavonoids on monoamine oxidases (MAOs) have attracted great interest since alterations in monoaminergic transmission are reported to be related to neurodegenerative diseases such as Parkinson's and Alzheimer's diseases and psychiatric disorders such as depression and anxiety, thus MAOs may be considered as targets for the treatment of these multi-factorial diseases. In the present study, four Sideritis flavonoids, xanthomicrol (1), isoscutellarein 7-O-[6'''-O-acetyl-beta-D-allopyranosyl-(1-->2)]-beta-D-glucopyranoside (2), isoscutellarein 7-O-[6'''-O-acetyl-beta-D-allopyranosyl-(1-->2)]-6''-O-acetyl-beta-D-glucopyranos ide (3) and Salvigenin (4) were docked computationally into the active site of the human monoamine oxidase isoforms (hMAO-A and hMAO-B) and were also investigated for their hMAO inhibitory potencies using recombinant hMAO isoenzymes. The flavonoids inhibited hMAO-A selectively and reversibly in a competitive mode. Salvigenin (4) was found to be the most potent hMAO-A inhibitor, while xanthomicrol (1) appeared as the most selective hMAO-A inhibitor. The computationally obtained results were in good agreement with the corresponding experimental values. In addition, the x-ray structure of xanthomicrol (1) has been shown. The current work warrants further preclinical studies to assess the potential of xanthomicrol (1) and Salvigenin (4) as new selective and reversible hMAO-A inhibitors for the treatment of depression and anxiety.

Antitumor and immunomodulatory effects of salvigenin on tumor bearing mice.[Pubmed:24270218]

Cell Immunol. 2013 Nov-Dec;286(1-2):16-21.

Development of agents that specifically kill cancer cells and simultaneously elicit antitumor immune response is a step forward in cancer therapy. Immunostimulation can result in eliminating of the cancer cells; immunotherapy is a promising approach in balancing the immune response by Treg. In the present study, we investigated whether the administration of Salvigenin contributes to the augmentation of antitumor immunity and the regression of tumor tissues in a mouse model of breast cancer. Salvigenin was purified from Tanacetum canescens, and its effect on the tumor volume was investigated. The splenocyte proliferation, shifting of cytokine profile, and the presence of naturally-occurring CD4+CD25+Foxp3+ Treg cells were assessed to describe the anti-tumor immune response. Our results demonstrated that a significant decrease in the level of IL-4 and increase in the IFN-gamma in the animals treated with Salvigenin and significant decreased in the level of splenic CD4+CD25+Foxp3+ T regulatory cells. The cytotoxic and immunomodulatory properties of Salvigenin were acknowledged in vivo.

Description

Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties.

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